diff --git a/.github/ISSUE_TEMPLATE/config.yml b/.github/ISSUE_TEMPLATE/config.yml
index cbf380bac01..fc86c229c81 100644
--- a/.github/ISSUE_TEMPLATE/config.yml
+++ b/.github/ISSUE_TEMPLATE/config.yml
@@ -1,4 +1,4 @@
-blank_issues_enabled: true
+blank_issues_enabled: false
 contact_links:
   - name: Schedule Demo
     url: https://enterprise.litellm.ai/demo
diff --git a/.github/workflows/test-linting.yml b/.github/workflows/test-linting.yml
index 9f1283da19e..06d369eabcd 100644
--- a/.github/workflows/test-linting.yml
+++ b/.github/workflows/test-linting.yml
@@ -113,7 +113,7 @@ jobs:
       - name: Check ruff format
         if: steps.changes.outputs.decision != 'skip'
         run: |
-          git diff --name-only --diff-filter=ACMR "$GATE_BASE_SHA" HEAD -- 'litellm/**/*.py' | grep -v '^litellm/enterprise/' > "$RUNNER_TEMP/ruff_format_files.txt" || true
+          git diff --name-only --diff-filter=ACMR "$GATE_BASE_SHA" HEAD -- ':(glob)litellm/**/*.py' | grep -v '^litellm/enterprise/' > "$RUNNER_TEMP/ruff_format_files.txt" || true
           if [ ! -s "$RUNNER_TEMP/ruff_format_files.txt" ]; then
             echo "No changed litellm Python files to check with ruff format."
             exit 0
@@ -172,7 +172,7 @@ jobs:
       - name: Check tests/e2e basedpyright (zero errors)
         if: steps.changes.outputs.decision != 'skip'
         run: |
-          if git diff --name-only --diff-filter=ACMRD "$GATE_BASE_SHA" HEAD -- 'tests/e2e/**/*.py' | grep -q .; then
+          if git diff --name-only --diff-filter=ACMRD "$GATE_BASE_SHA" HEAD -- ':(glob)tests/e2e/**/*.py' | grep -q .; then
             uv run --no-sync basedpyright tests/e2e
           else
             echo "No changed tests/e2e Python files; skipping."
diff --git a/.github/workflows/test-rust.yml b/.github/workflows/test-rust.yml
index c6901411167..17b6481a2bf 100644
--- a/.github/workflows/test-rust.yml
+++ b/.github/workflows/test-rust.yml
@@ -4,8 +4,22 @@ on:
   push:
     paths:
       - "litellm-rust/**"
+      - "litellm/rust_bridge/**"
+      - "tests/test_litellm_rust/**"
+      - "litellm/integrations/custom_logger.py"
+      - "litellm/litellm_core_utils/litellm_logging.py"
+      - "litellm/litellm_core_utils/logging_worker.py"
+      - "litellm/proxy/guardrails/**"
+      - "litellm/utils.py"
+      - "litellm/ocr/**"
+      - "litellm/llms/base_llm/ocr/**"
+      - "litellm/llms/custom_httpx/llm_http_handler.py"
+      - "tests/test_litellm/ocr/**"
+      - "tests/test_litellm/conftest.py"
+      - "Makefile"
       - ".cargo/**"
       - "pyproject.toml"
+      - "uv.lock"
       - "rust-toolchain.toml"
       - ".github/actions/setup-uv-with-retries/**"
       - ".github/scripts/smoke_test_native_wheel.py"
@@ -20,8 +34,22 @@ on:
       - "litellm_**"
     paths:
       - "litellm-rust/**"
+      - "litellm/rust_bridge/**"
+      - "tests/test_litellm_rust/**"
+      - "litellm/integrations/custom_logger.py"
+      - "litellm/litellm_core_utils/litellm_logging.py"
+      - "litellm/litellm_core_utils/logging_worker.py"
+      - "litellm/proxy/guardrails/**"
+      - "litellm/utils.py"
+      - "litellm/ocr/**"
+      - "litellm/llms/base_llm/ocr/**"
+      - "litellm/llms/custom_httpx/llm_http_handler.py"
+      - "tests/test_litellm/ocr/**"
+      - "tests/test_litellm/conftest.py"
+      - "Makefile"
       - ".cargo/**"
       - "pyproject.toml"
+      - "uv.lock"
       - "rust-toolchain.toml"
       - ".github/actions/setup-uv-with-retries/**"
       - ".github/scripts/smoke_test_native_wheel.py"
diff --git a/.github/workflows/test-terraform-modules.yml b/.github/workflows/test-terraform-modules.yml
index 52006d9b578..e6896604b7f 100644
--- a/.github/workflows/test-terraform-modules.yml
+++ b/.github/workflows/test-terraform-modules.yml
@@ -25,13 +25,17 @@ concurrency:
   cancel-in-progress: true
 
 jobs:
-  aws-module:
-    name: fmt, validate, test (aws)
+  module:
+    name: fmt, validate, test (${{ matrix.module }})
     runs-on: ubuntu-latest
     timeout-minutes: 15
+    strategy:
+      fail-fast: false
+      matrix:
+        module: [aws, gcp]
     defaults:
       run:
-        working-directory: terraform/litellm/aws
+        working-directory: terraform/litellm/${{ matrix.module }}
     steps:
       - uses: actions/checkout@08eba0b27e820071cde6df949e0beb9ba4906955 # v4.3.0
         with:
@@ -51,35 +55,7 @@ jobs:
       - name: validate
         run: terraform validate
 
-      # Plan-only, mock_provider-backed: no AWS credentials, no API calls.
+      # Plan-only, mock_provider-backed: no cloud credentials, no API calls.
       - name: test
         run: terraform test
 
-  gcp-module:
-    name: fmt, validate, test (gcp)
-    runs-on: ubuntu-latest
-    timeout-minutes: 15
-    defaults:
-      run:
-        working-directory: terraform/litellm/gcp
-    steps:
-      - uses: actions/checkout@08eba0b27e820071cde6df949e0beb9ba4906955 # v4.3.0
-        with:
-          persist-credentials: false
-
-      - uses: hashicorp/setup-terraform@b9cd54a3c349d3f38e8881555d616ced269862dd # v3.1.2
-        with:
-          terraform_version: 1.13.3
-          terraform_wrapper: false
-
-      - name: fmt
-        run: terraform fmt -recursive -check -diff
-
-      - name: init
-        run: terraform init -backend=false -input=false
-
-      - name: validate
-        run: terraform validate
-
-      - name: test
-        run: terraform test
diff --git a/.github/workflows/test-unit.yml b/.github/workflows/test-unit.yml
index cc606339a20..f55c87c2ae5 100644
--- a/.github/workflows/test-unit.yml
+++ b/.github/workflows/test-unit.yml
@@ -200,6 +200,7 @@ jobs:
               tests/test_litellm/proxy/types_utils
               tests/test_litellm/proxy/logging_endpoints
               tests/test_litellm/proxy/test_*.py
+              tests/test_gateway
             workers: 4
             reruns: 2
             timeout-minutes: 20
diff --git a/AGENTS.md b/AGENTS.md
index 41921fdff4d..a1e8f6f618d 100644
--- a/AGENTS.md
+++ b/AGENTS.md
@@ -1 +1,3 @@
 Read @CLAUDE.md for coding guidelines
+
+Before requesting maintainer review, verify the current PR tip passes required CI and code coverage, meets Greptile confidence of at least 4/5, and has acceptable Veria and Bugbot reviews. Inspect warnings and findings, fix actionable issues, and rerun the affected checks and reviewers after changes. Record evidence for any false positive or unavailable review; never treat a pending or missing bot result as a pass. Do not lower coverage thresholds or lint budgets to satisfy a check
diff --git a/Dockerfile b/Dockerfile
index 0a92aa9a68c..759dac76795 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -8,9 +8,25 @@ ARG LITELLM_RUNTIME_IMAGE=cgr.dev/chainguard/wolfi-base@sha256:e624c5d5e42382ce7
 ARG UV_IMAGE=ghcr.io/astral-sh/uv:0.11.7@sha256:240fb85ab0f263ef12f492d8476aa3a2e4e1e333f7d67fbdd923d00a506a516a
 # Pinned by digest like the other base images; bump explicitly on Node upgrades.
 ARG UI_BUILD_IMAGE=node:24.19-alpine3.24@sha256:d32cdf619f63fe0471182d08996dd516c6275bb5fd31ae06e55a570bd9e1ad43
+# Checksum from https://www.pgbouncer.org/downloads/ (the Wolfi repo only carries 1.24.x)
+ARG PGBOUNCER_VERSION=1.25.2
+ARG PGBOUNCER_SHA256=924ad35113fd0a71c8e2dbe85b5d03445532e2b7b37a9f8a48983beea238b332
 
 FROM $UV_IMAGE AS uvbin
 
+FROM $LITELLM_BUILD_IMAGE AS pgbouncer-builder
+ARG PGBOUNCER_VERSION
+ARG PGBOUNCER_SHA256
+USER root
+RUN apk add --no-cache build-base pkgconf libevent-dev openssl-dev curl
+WORKDIR /build
+RUN curl -fsSL -o pgbouncer.tar.gz "https://www.pgbouncer.org/downloads/files/${PGBOUNCER_VERSION}/pgbouncer-${PGBOUNCER_VERSION}.tar.gz" && \
+    echo "${PGBOUNCER_SHA256}  pgbouncer.tar.gz" | sha256sum -c - && \
+    tar xzf pgbouncer.tar.gz --strip-components=1 && \
+    ./configure --prefix=/usr/local --with-openssl=/usr && \
+    make -j"$(nproc)" pgbouncer && \
+    install -m 0755 pgbouncer /usr/local/bin/pgbouncer
+
 # Admin UI builder. Pinned to the build platform so the architecture-independent
 # Next.js static export compiles once natively even in a multi-arch build,
 # instead of once per target arch under QEMU.
@@ -110,7 +126,8 @@ USER root
 RUN echo "https://packages.wolfi.dev/os" >> /etc/apk/repositories
 
 # node (without npm) is required by the prisma CLI at runtime
-RUN apk add --no-cache bash openssl tzdata nodejs python-3.13 libsndfile
+RUN apk add --no-cache bash openssl tzdata nodejs python-3.13 libsndfile libevent
+COPY --from=pgbouncer-builder /usr/local/bin/pgbouncer /usr/local/bin/pgbouncer
 
 WORKDIR /app
 ENV PATH="/app/.venv/bin:${PATH}" \
diff --git a/Makefile b/Makefile
index 91835e19e3c..d360074ea4e 100644
--- a/Makefile
+++ b/Makefile
@@ -150,8 +150,8 @@ lint-install:
 # Diff-scoped format check, mirroring test-linting.yml's "Check ruff format" step:
 # only the litellm Python files changed vs the base are checked, so a pre-existing
 # format issue elsewhere doesn't block an unrelated commit. Git pathspecs match
-# recursively, so 'litellm/*.py' covers nested modules and the top-level files that
-# CI's 'litellm/**/*.py' skips, which makes this target a superset of the CI step.
+# recursively, so 'litellm/*.py' covers top-level files and nested modules alike,
+# the same set CI's ':(glob)litellm/**/*.py' selects.
 lint-format-check-changed: $(LINT_DEP_INSTALL) $(LINT_DEP_BASE)
 	@base_ref=$$($(RESOLVE_BASE)) && \
 	changed=$$(git diff --name-only --diff-filter=ACMR "$$base_ref...HEAD" -- 'litellm/*.py') && \
diff --git a/basedpyright-code-budget.json b/basedpyright-code-budget.json
index 57ca267e504..26e4e06a796 100644
--- a/basedpyright-code-budget.json
+++ b/basedpyright-code-budget.json
@@ -105,7 +105,7 @@
     "limit": 109
   },
   "reportUnknownMemberType": {
-    "limit": 38271
+    "limit": 38269
   },
   "reportUnknownParameterType": {
     "limit": 19584
diff --git a/docker/Dockerfile.database b/docker/Dockerfile.database
index e9ad2849bb2..b0bf935c616 100644
--- a/docker/Dockerfile.database
+++ b/docker/Dockerfile.database
@@ -8,9 +8,25 @@ ARG LITELLM_RUNTIME_IMAGE=cgr.dev/chainguard/wolfi-base@sha256:e624c5d5e42382ce7
 ARG UV_IMAGE=ghcr.io/astral-sh/uv:0.11.7@sha256:240fb85ab0f263ef12f492d8476aa3a2e4e1e333f7d67fbdd923d00a506a516a
 # Pinned by digest like the other base images; bump explicitly on Node upgrades.
 ARG UI_BUILD_IMAGE=node:24.19-alpine3.24@sha256:d32cdf619f63fe0471182d08996dd516c6275bb5fd31ae06e55a570bd9e1ad43
+# Checksum from https://www.pgbouncer.org/downloads/ (the Wolfi repo only carries 1.24.x)
+ARG PGBOUNCER_VERSION=1.25.2
+ARG PGBOUNCER_SHA256=924ad35113fd0a71c8e2dbe85b5d03445532e2b7b37a9f8a48983beea238b332
 
 FROM $UV_IMAGE AS uvbin
 
+FROM $LITELLM_BUILD_IMAGE AS pgbouncer-builder
+ARG PGBOUNCER_VERSION
+ARG PGBOUNCER_SHA256
+USER root
+RUN apk add --no-cache build-base pkgconf libevent-dev openssl-dev curl
+WORKDIR /build
+RUN curl -fsSL -o pgbouncer.tar.gz "https://www.pgbouncer.org/downloads/files/${PGBOUNCER_VERSION}/pgbouncer-${PGBOUNCER_VERSION}.tar.gz" && \
+    echo "${PGBOUNCER_SHA256}  pgbouncer.tar.gz" | sha256sum -c - && \
+    tar xzf pgbouncer.tar.gz --strip-components=1 && \
+    ./configure --prefix=/usr/local --with-openssl=/usr && \
+    make -j"$(nproc)" pgbouncer && \
+    install -m 0755 pgbouncer /usr/local/bin/pgbouncer
+
 # Admin UI builder. Pinned to the build platform so the architecture-independent
 # Next.js static export compiles once natively even in a multi-arch build,
 # instead of once per target arch under QEMU.
@@ -101,7 +117,8 @@ FROM $LITELLM_RUNTIME_IMAGE AS runtime
 USER root
 
 # node (without npm) is required by the prisma CLI at runtime
-RUN apk add --no-cache bash openssl tzdata nodejs python-3.13 libsndfile
+RUN apk add --no-cache bash openssl tzdata nodejs python-3.13 libsndfile libevent
+COPY --from=pgbouncer-builder /usr/local/bin/pgbouncer /usr/local/bin/pgbouncer
 
 WORKDIR /app
 ENV PATH="/app/.venv/bin:${PATH}" \
diff --git a/docker/Dockerfile.non_root b/docker/Dockerfile.non_root
index edf20e8bbff..5d729046678 100644
--- a/docker/Dockerfile.non_root
+++ b/docker/Dockerfile.non_root
@@ -7,9 +7,25 @@ ARG PROXY_EXTRAS_SOURCE=published
 ARG UV_IMAGE=ghcr.io/astral-sh/uv:0.11.7@sha256:240fb85ab0f263ef12f492d8476aa3a2e4e1e333f7d67fbdd923d00a506a516a
 # Pinned by digest like the other base images; bump explicitly on Node upgrades.
 ARG UI_BUILD_IMAGE=node:24.19-alpine3.24@sha256:d32cdf619f63fe0471182d08996dd516c6275bb5fd31ae06e55a570bd9e1ad43
+# Checksum from https://www.pgbouncer.org/downloads/ (the Wolfi repo only carries 1.24.x)
+ARG PGBOUNCER_VERSION=1.25.2
+ARG PGBOUNCER_SHA256=924ad35113fd0a71c8e2dbe85b5d03445532e2b7b37a9f8a48983beea238b332
 
 FROM $UV_IMAGE AS uvbin
 
+FROM $LITELLM_BUILD_IMAGE AS pgbouncer-builder
+ARG PGBOUNCER_VERSION
+ARG PGBOUNCER_SHA256
+USER root
+RUN apk add --no-cache build-base pkgconf libevent-dev openssl-dev curl
+WORKDIR /build
+RUN curl -fsSL -o pgbouncer.tar.gz "https://www.pgbouncer.org/downloads/files/${PGBOUNCER_VERSION}/pgbouncer-${PGBOUNCER_VERSION}.tar.gz" && \
+    echo "${PGBOUNCER_SHA256}  pgbouncer.tar.gz" | sha256sum -c - && \
+    tar xzf pgbouncer.tar.gz --strip-components=1 && \
+    ./configure --prefix=/usr/local --with-openssl=/usr && \
+    make -j"$(nproc)" pgbouncer && \
+    install -m 0755 pgbouncer /usr/local/bin/pgbouncer
+
 # Admin UI builder. Pinned to the build platform so the architecture-independent
 # Next.js static export compiles once natively even in a multi-arch build,
 # instead of once per target arch under QEMU.
@@ -128,8 +144,9 @@ RUN for i in 1 2 3; do \
       apk upgrade --no-cache && break || sleep 5; \
     done && \
     for i in 1 2 3; do \
-      apk add --no-cache python-3.13 bash openssl tzdata libsndfile nodejs && break || sleep 5; \
+      apk add --no-cache python-3.13 bash openssl tzdata libsndfile nodejs libevent && break || sleep 5; \
     done
+COPY --from=pgbouncer-builder /usr/local/bin/pgbouncer /usr/local/bin/pgbouncer
 
 # Copy only what runtime needs. The application is installed inside the venv;
 # the rest of the builder's /app is source and build metadata that must not
diff --git a/enterprise/litellm_enterprise/proxy/hooks/managed_files.py b/enterprise/litellm_enterprise/proxy/hooks/managed_files.py
index 486904d0abe..c7e1b94a2ef 100644
--- a/enterprise/litellm_enterprise/proxy/hooks/managed_files.py
+++ b/enterprise/litellm_enterprise/proxy/hooks/managed_files.py
@@ -1801,7 +1801,16 @@ class _PROXY_LiteLLMManagedFiles(CustomLogger, BaseFileEndpoints):
             # Remove conflicting keys from data to avoid duplicate keyword arguments
             filtered_data = {k: v for k, v in data.items() if k not in ("model", "file_id")}
             for model_id, model_file_id in specific_model_file_id_mapping.items():
-                delete_response = await llm_router.afile_delete(model=model_id, file_id=model_file_id, **filtered_data)  # type: ignore
+                credentials = llm_router.get_deployment_credentials_with_provider(model_id=model_id)
+                delete_data = {
+                    **{k: v for k, v in filtered_data.items() if k != "_litellm_internal_model_credentials"},
+                    **(
+                        {"_litellm_internal_model_credentials": MappingProxyType(dict(credentials))}
+                        if credentials is not None
+                        else {}
+                    ),
+                }
+                delete_response = await llm_router.afile_delete(model=model_id, file_id=model_file_id, **delete_data)
 
         stored_file_object = await self.delete_unified_file_id(file_id, litellm_parent_otel_span)
 
@@ -1812,7 +1821,7 @@ class _PROXY_LiteLLMManagedFiles(CustomLogger, BaseFileEndpoints):
                 prom_logger.record_managed_file_deleted(result="success")
 
         if stored_file_object:
-            return stored_file_object
+            return OpenAIFileObject.model_validate(stored_file_object).model_copy(update={"id": file_id})
         elif delete_response:
             delete_response.id = file_id
             return delete_response
diff --git a/gateway/Dockerfile b/gateway/Dockerfile
index 308d70a6b26..33d3791dbba 100644
--- a/gateway/Dockerfile
+++ b/gateway/Dockerfile
@@ -1,9 +1,25 @@
 ARG LITELLM_BUILD_IMAGE=cgr.dev/chainguard/wolfi-base@sha256:e624c5d5e42382ce7165ddafcbbf8e6769a24cbd02ea6114b880b05ae5ba2a8d
 ARG LITELLM_RUNTIME_IMAGE=cgr.dev/chainguard/wolfi-base@sha256:e624c5d5e42382ce7165ddafcbbf8e6769a24cbd02ea6114b880b05ae5ba2a8d
 ARG UV_IMAGE=ghcr.io/astral-sh/uv:0.11.7@sha256:240fb85ab0f263ef12f492d8476aa3a2e4e1e333f7d67fbdd923d00a506a516a
+# Checksum from https://www.pgbouncer.org/downloads/ (the Wolfi repo only carries 1.24.x)
+ARG PGBOUNCER_VERSION=1.25.2
+ARG PGBOUNCER_SHA256=924ad35113fd0a71c8e2dbe85b5d03445532e2b7b37a9f8a48983beea238b332
 
 FROM $UV_IMAGE AS uvbin
 
+FROM $LITELLM_BUILD_IMAGE AS pgbouncer-builder
+ARG PGBOUNCER_VERSION
+ARG PGBOUNCER_SHA256
+USER root
+RUN apk add --no-cache build-base pkgconf libevent-dev openssl-dev curl
+WORKDIR /build
+RUN curl -fsSL -o pgbouncer.tar.gz "https://www.pgbouncer.org/downloads/files/${PGBOUNCER_VERSION}/pgbouncer-${PGBOUNCER_VERSION}.tar.gz" && \
+    echo "${PGBOUNCER_SHA256}  pgbouncer.tar.gz" | sha256sum -c - && \
+    tar xzf pgbouncer.tar.gz --strip-components=1 && \
+    ./configure --prefix=/usr/local --with-openssl=/usr && \
+    make -j"$(nproc)" pgbouncer && \
+    install -m 0755 pgbouncer /usr/local/bin/pgbouncer
+
 # ---------- Builder ----------
 FROM $LITELLM_BUILD_IMAGE AS builder
 
@@ -61,6 +77,10 @@ RUN --mount=type=cache,target=/root/.cache/uv \
         --extra bedrock-realtime \
         --python python3.13
 
+# PYTHONPATH=/app makes the source tree shadow the installed package, so the
+# compiled Rust extension must live next to the source or it is never imported.
+RUN cp "$(python -c 'import sysconfig; print(sysconfig.get_paths()["purelib"])')"/litellm/rust_bridge/_native*.so litellm/rust_bridge/
+
 RUN HOME=/opt/prisma XDG_CACHE_HOME=/opt/prisma/.cache PRISMA_BINARY_CACHE_DIR=/opt/prisma/binaries \
     npm_config_cache=/root/.npm \
     prisma generate --schema=./schema.prisma
@@ -73,7 +93,7 @@ FROM $LITELLM_RUNTIME_IMAGE AS runtime
 USER root
 
 RUN for i in 1 2 3; do \
-      apk add --no-cache bash openssl tzdata python-3.13 libsndfile libatomic && break; \
+      apk add --no-cache bash openssl tzdata python-3.13 libsndfile libatomic libevent && break; \
       [ $i = 3 ] && { echo "apk add failed after 3 retries" >&2; exit 1; }; \
       sleep 5; \
     done
@@ -90,15 +110,17 @@ ENV HOME=/home/nonroot \
 
 COPY --from=builder --chown=nonroot:nonroot /app /app
 COPY --from=builder /opt/prisma /opt/prisma
+COPY --from=pgbouncer-builder /usr/local/bin/pgbouncer /usr/local/bin/pgbouncer
 
 RUN find /app/.venv -type f -path "*/tornado/test/*" -delete && \
     find /app/.venv -type d -path "*/tornado/test" -delete && \
     chmod -R a+rX /opt/prisma && \
-    python -c "from prisma.client import BINARY_PATHS; paths = list(BINARY_PATHS.query_engine.values()); assert paths and all(p.startswith('/opt/prisma/') for p in paths), paths"
+    python -c "from prisma.client import BINARY_PATHS; paths = list(BINARY_PATHS.query_engine.values()); assert paths and all(p.startswith('/opt/prisma/') for p in paths), paths" && \
+    python -c "import litellm; from litellm.rust_bridge.loader import native_bridge_available; assert litellm.__file__ == '/app/litellm/__init__.py', litellm.__file__; assert native_bridge_available()"
 
 USER nonroot
 
 EXPOSE 4000/tcp
 
-ENTRYPOINT ["sh", "-c", "exec /app/docker/component_entrypoint.sh uvicorn gateway.main:app --workers \"${NUM_WORKERS:-1}\" \"$@\"", "--"]
+ENTRYPOINT ["sh", "-c", "exec /app/docker/component_entrypoint.sh python -m gateway.launch --workers \"${NUM_WORKERS:-1}\" \"$@\"", "--"]
 CMD ["--host", "0.0.0.0", "--port", "4000"]
diff --git a/gateway/launch.py b/gateway/launch.py
new file mode 100644
index 00000000000..d67432caee1
--- /dev/null
+++ b/gateway/launch.py
@@ -0,0 +1,77 @@
+"""Gateway supervisor: assemble DATABASE_URL, start the in-container PgBouncer, then run uvicorn.
+
+``gateway/main.py`` assembles ``DATABASE_URL`` inside every uvicorn worker, which
+is fine for a plain Postgres URL but not for the pooler: PgBouncer must be
+started exactly once per pod, before the workers fork, and the workers must be
+handed the loopback URL it listens on. A pre-existing ``DATABASE_URL`` wins in
+``DatabaseURLSettings.apply_to_env`` under password auth, and one marked pooled
+wins under token auth too, so exporting it here is enough for every worker to
+pick the pooled URL up unchanged.
+
+Run with:
+    python -m gateway.launch --workers 4 --host 0.0.0.0 --port 4000
+"""
+
+import os
+import sys
+from collections.abc import Callable, Mapping, Sequence
+from typing import Final
+
+from uvicorn.main import main as uvicorn_main
+
+from litellm.proxy.db.db_url_settings import DatabaseURLSettings
+from litellm.proxy.db.pgbouncer import (
+    PgBouncerError,
+    PgBouncerSettings,
+    export_pooled_database_url,
+    start_in_container_pgbouncer,
+)
+
+GATEWAY_APP: Final = "gateway.main:app"
+KEEPALIVE_FLAG: Final = "--timeout-keep-alive"
+
+
+def uvicorn_argv(argv: Sequence[str], environ: Mapping[str, str]) -> tuple[str, ...]:
+    """Honor ``KEEPALIVE_TIMEOUT`` like ``proxy_cli.py`` does, unless the flag was passed explicitly."""
+    keepalive: Final = environ.get("KEEPALIVE_TIMEOUT")
+    if keepalive is None or any(arg == KEEPALIVE_FLAG or arg.startswith(f"{KEEPALIVE_FLAG}=") for arg in argv):
+        return (GATEWAY_APP, *argv)
+    return (GATEWAY_APP, *argv, KEEPALIVE_FLAG, keepalive)
+
+
+def pool_database_url(
+    settings: DatabaseURLSettings,
+    pgbouncer: PgBouncerSettings,
+    environ: Mapping[str, str],
+) -> str | PgBouncerError | None:
+    """Start the in-container PgBouncer and return its loopback URL, or None when ``pgbouncer.enabled`` is off.
+
+    The upstream URL is whatever ``apply_to_env`` assembled from the discrete
+    ``DATABASE_*`` vars (or an operator-pinned ``DATABASE_URL``). Under token
+    auth the pooler mints and renews the upstream token itself.
+    """
+    if not pgbouncer.enabled:
+        return None
+    upstream_url: Final = environ.get("DATABASE_URL")
+    if upstream_url is None:
+        return PgBouncerError("LITELLM_PGBOUNCER_ENABLED is set but no DATABASE_URL could be assembled")
+    return start_in_container_pgbouncer(pgbouncer, upstream_url, token_auth=settings.token_auth())
+
+
+def _serve(argv: Sequence[str]) -> None:
+    uvicorn_main(tuple(argv), prog_name="uvicorn")
+
+
+def main(argv: Sequence[str], serve: Callable[[Sequence[str]], None] = _serve) -> None:
+    settings: Final = DatabaseURLSettings.from_env()
+    settings.apply_to_env()
+    pooled_url: Final = pool_database_url(settings, PgBouncerSettings(), os.environ)
+    if isinstance(pooled_url, PgBouncerError):
+        sys.exit(f"LiteLLM gateway: in-container pgbouncer could not start: {pooled_url.reason}")
+    if pooled_url is not None:
+        export_pooled_database_url(pooled_url)
+    serve(uvicorn_argv(argv, os.environ))
+
+
+if __name__ == "__main__":
+    main(sys.argv[1:])
diff --git a/helm/litellm-helm/templates/_helpers.tpl b/helm/litellm-helm/templates/_helpers.tpl
index 8f2acb20fce..9630633912e 100644
--- a/helm/litellm-helm/templates/_helpers.tpl
+++ b/helm/litellm-helm/templates/_helpers.tpl
@@ -161,3 +161,163 @@ taken before the change, which by that point no longer exists.
 {{- fail (printf "postgresql.image.tag must be pinned to an explicit version when db.deployStandalone is true (got %q). An unpinned tag can start a different PostgreSQL major against the existing data directory, which makes the database unreadable and is not recoverable in place. Crossing a major version requires a dump and restore." $tag) -}}
 {{- end -}}
 {{- end -}}
+
+{{/*
+Environment shared by the proxy container and the opt-in collector sidecar:
+database, pgbouncer, master key, redis, user envVars. Both containers must see
+the same DATABASE_URL and REDIS_* so the sidecar reaches the pod's pgbouncer
+and the same spend transaction buffer.
+*/}}
+{{- define "litellm.proxyEnv" -}}
+- name: HOST
+  value: "{{ .Values.listen | default "0.0.0.0" }}"
+- name: PORT
+  value: {{ .Values.service.port | quote}}
+{{- if .Values.db.deployStandalone }}
+- name: DATABASE_USERNAME
+  valueFrom:
+    secretKeyRef:
+      name: {{ include "litellm.fullname" . }}-dbcredentials
+      key: username
+- name: DATABASE_PASSWORD
+  valueFrom:
+    secretKeyRef:
+      name: {{ include "litellm.fullname" . }}-dbcredentials
+      key: password
+- name: DATABASE_HOST
+  value: {{ .Release.Name }}-postgresql
+- name: DATABASE_NAME
+  value: litellm
+{{- else if .Values.db.useExisting }}
+- name: DATABASE_USERNAME
+  valueFrom:
+    secretKeyRef:
+      name: {{ .Values.db.secret.name }}
+      key: {{ .Values.db.secret.usernameKey }}
+- name: DATABASE_PASSWORD
+  valueFrom:
+    secretKeyRef:
+      name: {{ .Values.db.secret.name }}
+      key: {{ .Values.db.secret.passwordKey }}
+- name: DATABASE_HOST
+  {{- if .Values.db.secret.endpointKey }}
+  valueFrom:
+    secretKeyRef:
+      name: {{ .Values.db.secret.name }}
+      key: {{ .Values.db.secret.endpointKey }}
+  {{- else }}
+  value: {{ .Values.db.endpoint }}
+  {{- end }}
+- name: DATABASE_NAME
+  value: {{ .Values.db.database }}
+- name: DATABASE_URL
+  value: {{ .Values.db.url | quote }}
+{{- end }}
+{{- if and .Values.db.useExisting .Values.db.readReplicaUrl .Values.db.secret.readReplicaEndpointKey (not .Values.db.secret.readReplicaUrlKey) }}
+- name: DATABASE_READER_HOST
+  valueFrom:
+    secretKeyRef:
+      name: {{ .Values.db.secret.name }}
+      key: {{ .Values.db.secret.readReplicaEndpointKey }}
+{{- end }}
+{{- if and .Values.db.useExisting .Values.db.secret.readReplicaUrlKey }}
+- name: DATABASE_URL_READ_REPLICA
+  valueFrom:
+    secretKeyRef:
+      name: {{ .Values.db.secret.name }}
+      key: {{ .Values.db.secret.readReplicaUrlKey }}
+{{- else if .Values.db.readReplicaUrl }}
+- name: DATABASE_URL_READ_REPLICA
+  value: {{ .Values.db.readReplicaUrl | quote }}
+{{- end }}
+{{- if .Values.db.connectionPool.enabled }}
+- name: LITELLM_PGBOUNCER_ENABLED
+  value: "true"
+- name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+  value: {{ .Values.db.connectionPool.maxDbConnections | quote }}
+- name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+  value: {{ .Values.db.connectionPool.maxClientConn | quote }}
+{{- end }}
+- name: PROXY_MASTER_KEY
+  valueFrom:
+    secretKeyRef:
+      name: {{ .Values.masterkeySecretName | default (printf "%s-masterkey" (include "litellm.fullname" .)) }}
+      key: {{ .Values.masterkeySecretKey | default "masterkey" }}
+{{- if .Values.redis.enabled }}
+- name: REDIS_HOST
+  value: {{ include "litellm.redis.serviceName" . }}
+- name: REDIS_PORT
+  value: {{ include "litellm.redis.port" . | quote }}
+- name: REDIS_PASSWORD
+  valueFrom:
+    secretKeyRef:
+      name: {{ include "redis.secretName" .Subcharts.redis }}
+      key: {{include "redis.secretPasswordKey" .Subcharts.redis }}
+{{- end }}
+{{- /*
+  Inject LITELLM_LOG only when envVars does not already define it.
+*/}}
+{{- if and .Values.logLevel (not (hasKey (default dict .Values.envVars) "LITELLM_LOG")) }}
+- name: LITELLM_LOG
+  value: {{ .Values.logLevel | quote }}
+{{- end }}
+{{- if .Values.envVars }}
+{{- range $key, $val := .Values.envVars }}
+- name: {{ $key }}
+  value: {{ $val | quote }}
+{{- end }}
+{{- end }}
+{{- with .Values.extraEnvVars }}
+{{ toYaml . }}
+{{- end }}
+{{- if .Values.migrationJob.enabled }}
+# Schema updates are owned by the dedicated migrations Job; skip
+# the proxy's startup `prisma db push` so N replicas don't race
+# one DB on every rollout. Placed last (after envVars and
+# extraEnvVars) so this override can't be silently shadowed by a
+# user-supplied DISABLE_SCHEMA_UPDATE under last-wins duplicate-env
+# semantics — same pattern the migrations Job uses.
+- name: DISABLE_SCHEMA_UPDATE
+  value: "true"
+{{- end }}
+{{- end -}}
+
+{{/*
+Proxy-only metering and metrics env. The collector sidecar serves no HTTP
+traffic, so it gets neither.
+*/}}
+{{- define "litellm.proxyMetricsEnv" -}}
+{{- if .Values.billingMetrics.enabled }}
+{{ include "litellm.billingMetricsEnv" . }}
+{{- end }}
+{{- if .Values.metricsServer.enabled }}
+{{- if eq (int .Values.metricsServer.port) (int .Values.service.port) }}
+{{- fail "metricsServer.port must differ from service.port" }}
+{{- end }}
+- name: PROMETHEUS_METRICS_PORT
+  value: {{ .Values.metricsServer.port | quote }}
+{{- end }}
+{{- end -}}
+
+{{/*
+Directory of the collector's unix socket, shared between the two containers
+through an emptyDir. Empty when the sidecar is off or uses 127.0.0.1 TCP.
+*/}}
+{{- define "litellm.collector.socketDir" -}}
+{{- if and .Values.collector.enabled (hasPrefix "unix://" .Values.collector.address) -}}
+{{- dir (trimPrefix "unix://" .Values.collector.address) -}}
+{{- end -}}
+{{- end -}}
+
+{{- define "litellm.collectorEnv" -}}
+- name: LITELLM_COLLECTOR_ENABLED
+  value: "true"
+- name: LITELLM_COLLECTOR_ADDRESS
+  value: {{ .Values.collector.address | quote }}
+- name: LITELLM_COLLECTOR_BUFFER_SIZE
+  value: {{ .Values.collector.bufferSize | quote }}
+- name: LITELLM_COLLECTOR_ON_UNAVAILABLE
+  value: {{ .Values.collector.onUnavailable | quote }}
+- name: LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS
+  value: {{ .Values.collector.drainTimeoutSeconds | quote }}
+{{- end -}}
diff --git a/helm/litellm-helm/templates/deployment.yaml b/helm/litellm-helm/templates/deployment.yaml
index f7c918a6827..cf7b3f8a38d 100644
--- a/helm/litellm-helm/templates/deployment.yaml
+++ b/helm/litellm-helm/templates/deployment.yaml
@@ -56,118 +56,10 @@ spec:
           image: "{{ .Values.image.repository }}:{{ .Values.image.tag | default .Chart.AppVersion }}"
           imagePullPolicy: {{ .Values.image.pullPolicy }}
           env:
-            - name: HOST
-              value: "{{ .Values.listen | default "0.0.0.0" }}"
-            - name: PORT
-              value: {{ .Values.service.port | quote}}
-            {{- if .Values.db.deployStandalone }}
-            - name: DATABASE_USERNAME
-              valueFrom:
-                secretKeyRef:
-                  name: {{ include "litellm.fullname" . }}-dbcredentials
-                  key: username
-            - name: DATABASE_PASSWORD
-              valueFrom:
-                secretKeyRef:
-                  name: {{ include "litellm.fullname" . }}-dbcredentials
-                  key: password
-            - name: DATABASE_HOST
-              value: {{ .Release.Name }}-postgresql
-            - name: DATABASE_NAME
-              value: litellm
-            {{- else if .Values.db.useExisting }}
-            - name: DATABASE_USERNAME
-              valueFrom:
-                secretKeyRef:
-                  name: {{ .Values.db.secret.name }}
-                  key: {{ .Values.db.secret.usernameKey }}
-            - name: DATABASE_PASSWORD
-              valueFrom:
-                secretKeyRef:
-                  name: {{ .Values.db.secret.name }}
-                  key: {{ .Values.db.secret.passwordKey }}
-            - name: DATABASE_HOST
-              {{- if .Values.db.secret.endpointKey }}
-              valueFrom:
-                secretKeyRef:
-                  name: {{ .Values.db.secret.name }}
-                  key: {{ .Values.db.secret.endpointKey }}
-              {{- else }}
-              value: {{ .Values.db.endpoint }}
-              {{- end }}
-            - name: DATABASE_NAME
-              value: {{ .Values.db.database }}
-            - name: DATABASE_URL
-              value: {{ .Values.db.url | quote }}
-            {{- end }}
-            {{- if and .Values.db.useExisting .Values.db.readReplicaUrl .Values.db.secret.readReplicaEndpointKey (not .Values.db.secret.readReplicaUrlKey) }}
-            - name: DATABASE_READER_HOST
-              valueFrom:
-                secretKeyRef:
-                  name: {{ .Values.db.secret.name }}
-                  key: {{ .Values.db.secret.readReplicaEndpointKey }}
-            {{- end }}
-            {{- if and .Values.db.useExisting .Values.db.secret.readReplicaUrlKey }}
-            - name: DATABASE_URL_READ_REPLICA
-              valueFrom:
-                secretKeyRef:
-                  name: {{ .Values.db.secret.name }}
-                  key: {{ .Values.db.secret.readReplicaUrlKey }}
-            {{- else if .Values.db.readReplicaUrl }}
-            - name: DATABASE_URL_READ_REPLICA
-              value: {{ .Values.db.readReplicaUrl | quote }}
-            {{- end }}
-            - name: PROXY_MASTER_KEY
-              valueFrom:
-                secretKeyRef:
-                  name: {{ .Values.masterkeySecretName | default (printf "%s-masterkey" (include "litellm.fullname" .)) }}
-                  key: {{ .Values.masterkeySecretKey | default "masterkey" }}
-            {{- if .Values.redis.enabled }}
-            - name: REDIS_HOST
-              value: {{ include "litellm.redis.serviceName" . }}
-            - name: REDIS_PORT
-              value: {{ include "litellm.redis.port" . | quote }}
-            - name: REDIS_PASSWORD
-              valueFrom:
-                secretKeyRef:
-                  name: {{ include "redis.secretName" .Subcharts.redis }}
-                  key: {{include "redis.secretPasswordKey" .Subcharts.redis }}
-            {{- end }}
-            {{- /*
-              Inject LITELLM_LOG only when envVars does not already define it.
-            */}}
-            {{- if and .Values.logLevel (not (hasKey (default dict .Values.envVars) "LITELLM_LOG")) }}
-            - name: LITELLM_LOG
-              value: {{ .Values.logLevel | quote }}
-            {{- end }}
-            {{- if .Values.envVars }}
-            {{- range $key, $val := .Values.envVars }}
-            - name: {{ $key }}
-              value: {{ $val | quote }}
-            {{- end }}
-            {{- end }}
-            {{- with .Values.extraEnvVars }}
-              {{- toYaml . | nindent 12 }}
-            {{- end }}
-            {{- if .Values.billingMetrics.enabled }}
-            {{- include "litellm.billingMetricsEnv" . | nindent 12 }}
-            {{- end }}
-            {{- if .Values.metricsServer.enabled }}
-            {{- if eq (int .Values.metricsServer.port) (int .Values.service.port) }}
-            {{- fail "metricsServer.port must differ from service.port" }}
-            {{- end }}
-            - name: PROMETHEUS_METRICS_PORT
-              value: {{ .Values.metricsServer.port | quote }}
-            {{- end }}
-            {{- if .Values.migrationJob.enabled }}
-            # Schema updates are owned by the dedicated migrations Job; skip
-            # the proxy's startup `prisma db push` so N replicas don't race
-            # one DB on every rollout. Placed last (after envVars and
-            # extraEnvVars) so this override can't be silently shadowed by a
-            # user-supplied DISABLE_SCHEMA_UPDATE under last-wins duplicate-env
-            # semantics — same pattern the migrations Job uses.
-            - name: DISABLE_SCHEMA_UPDATE
-              value: "true"
+            {{- include "litellm.proxyEnv" . | nindent 12 }}
+            {{- include "litellm.proxyMetricsEnv" . | nindent 12 }}
+            {{- if .Values.collector.enabled }}
+            {{- include "litellm.collectorEnv" . | nindent 12 }}
             {{- end }}
           envFrom:
           {{- range .Values.environmentSecrets }}
@@ -245,6 +137,10 @@ spec:
           {{- if .Values.billingMetrics.enabled }}
             {{- include "litellm.billingMetricsVolumeMounts" . | nindent 12 }}
           {{- end }}
+          {{- if include "litellm.collector.socketDir" . }}
+            - name: collector-socket
+              mountPath: {{ include "litellm.collector.socketDir" . }}
+          {{- end }}
           {{- with .Values.volumeMounts }}
             {{- toYaml . | nindent 12 }}
           {{- end }}
@@ -252,6 +148,53 @@ spec:
           lifecycle:
             {{- toYaml . | nindent 12 }}
           {{- end }}
+      {{- if .Values.collector.enabled }}
+        - name: {{ include "litellm.name" . }}-collector
+          securityContext:
+            {{- toYaml .Values.securityContext | nindent 12 }}
+          image: "{{ .Values.image.repository }}:{{ .Values.image.tag | default .Chart.AppVersion }}"
+          imagePullPolicy: {{ .Values.image.pullPolicy }}
+          command: {{ toYaml .Values.collector.command | nindent 12 }}
+          env:
+            {{- include "litellm.proxyEnv" . | nindent 12 }}
+            {{- include "litellm.collectorEnv" . | nindent 12 }}
+            - name: LITELLM_JOB_ROLE
+              value: collector
+            {{- if not (hasKey (default dict .Values.envVars) "CONFIG_FILE_PATH") }}
+            - name: CONFIG_FILE_PATH
+              value: /etc/litellm/config.yaml
+            {{- end }}
+          envFrom:
+          {{- range .Values.environmentSecrets }}
+            - secretRef:
+                name: {{ . }}
+          {{- end }}
+          {{- range .Values.environmentConfigMaps }}
+            - configMapRef:
+                name: {{ . }}
+          {{- end }}
+          resources:
+            {{- toYaml .Values.collector.resources | nindent 12 }}
+          volumeMounts:
+            - name: litellm-config
+              mountPath: /etc/litellm/config.yaml
+              subPath: config.yaml
+          {{- if include "litellm.collector.socketDir" . }}
+            - name: collector-socket
+              mountPath: {{ include "litellm.collector.socketDir" . }}
+          {{- end }}
+          {{ if .Values.securityContext.readOnlyRootFilesystem }}
+            - name: tmp
+              mountPath: /tmp
+            - name: cache
+              mountPath: /.cache
+            - name: npm
+              mountPath: /.npm
+          {{- end }}
+          {{- with .Values.volumeMounts }}
+            {{- toYaml . | nindent 12 }}
+          {{- end }}
+      {{- end }}
       {{- with .Values.extraContainers }}
         {{- tpl (toYaml .) $ | nindent 8 }}
       {{- end }}
@@ -280,6 +223,11 @@ spec:
         {{- if .Values.billingMetrics.enabled }}
         {{- include "litellm.billingMetricsVolumes" . | nindent 8 }}
         {{- end }}
+        {{- if include "litellm.collector.socketDir" . }}
+        - name: collector-socket
+          emptyDir:
+            sizeLimit: 1Mi
+        {{- end }}
       {{- with .Values.volumes }}
         {{- toYaml . | nindent 8 }}
       {{- end }}
diff --git a/helm/litellm-helm/templates/hpa.yaml b/helm/litellm-helm/templates/hpa.yaml
index fec4d1f5c5e..a651f916d21 100644
--- a/helm/litellm-helm/templates/hpa.yaml
+++ b/helm/litellm-helm/templates/hpa.yaml
@@ -18,6 +18,15 @@ spec:
   {{- end }}
   metrics:
     {{- if .Values.autoscaling.targetCPUUtilizationPercentage }}
+    {{- if and .Values.collector.enabled .Values.collector.scaleOnProxyContainerCpu }}
+    - type: ContainerResource
+      containerResource:
+        name: cpu
+        container: {{ include "litellm.name" . }}
+        target:
+          type: Utilization
+          averageUtilization: {{ .Values.autoscaling.targetCPUUtilizationPercentage }}
+    {{- else }}
     - type: Resource
       resource:
         name: cpu
@@ -25,6 +34,7 @@ spec:
           type: Utilization
           averageUtilization: {{ .Values.autoscaling.targetCPUUtilizationPercentage }}
     {{- end }}
+    {{- end }}
     {{- if .Values.autoscaling.targetMemoryUtilizationPercentage }}
     - type: Resource
       resource:
@@ -33,4 +43,22 @@ spec:
           type: Utilization
           averageUtilization: {{ .Values.autoscaling.targetMemoryUtilizationPercentage }}
     {{- end }}
+    {{- with .Values.autoscaling.targetRequestsPerSecond }}
+    - type: Pods
+      pods:
+        metric:
+          name: litellm_requests_per_second
+        target:
+          type: AverageValue
+          averageValue: {{ toJson . | trimAll "\"" | quote }}
+    {{- end }}
+    {{- with .Values.autoscaling.targetTokensPerSecond }}
+    - type: Pods
+      pods:
+        metric:
+          name: litellm_tokens_per_second
+        target:
+          type: AverageValue
+          averageValue: {{ toJson . | trimAll "\"" | quote }}
+    {{- end }}
 {{- end }}
diff --git a/helm/litellm-helm/templates/keda.yaml b/helm/litellm-helm/templates/keda.yaml
index fe5190fffc6..bf585d0d4be 100644
--- a/helm/litellm-helm/templates/keda.yaml
+++ b/helm/litellm-helm/templates/keda.yaml
@@ -23,6 +23,27 @@ spec:
   triggers:
 {{- with .Values.keda.triggers }}
   {{- toYaml . | nindent 2 }}
+{{- end }}
+{{- $prom := .Values.keda.prometheus }}
+{{- if or $prom.requestsPerSecond $prom.tokensPerSecond }}
+{{- if not $prom.serverAddress }}
+{{- fail "keda.prometheus.serverAddress is required when keda.prometheus.requestsPerSecond or tokensPerSecond is set" }}
+{{- end }}
+{{- $selector := printf "namespace=%q,job=%q" .Release.Namespace (printf "%s%s" (include "litellm.fullname" .) (ternary "-metrics" "" .Values.metricsServer.enabled)) }}
+{{- with $prom.requestsPerSecond }}
+  - type: prometheus
+    metadata:
+      serverAddress: {{ $prom.serverAddress | quote }}
+      threshold: {{ toJson . | trimAll "\"" | quote }}
+      query: {{ printf "sum(rate(litellm_proxy_total_requests_metric_total{%s}[1m]))" $selector | quote }}
+{{- end }}
+{{- with $prom.tokensPerSecond }}
+  - type: prometheus
+    metadata:
+      serverAddress: {{ $prom.serverAddress | quote }}
+      threshold: {{ toJson . | trimAll "\"" | quote }}
+      query: {{ printf "sum(rate(litellm_total_tokens_metric_total{%s}[1m]))" $selector | quote }}
+{{- end }}
 {{- end }}
   advanced:
     restoreToOriginalReplicaCount: {{ .Values.keda.restoreToOriginalReplicaCount }}
diff --git a/helm/litellm-helm/tests/collector_tests.yaml b/helm/litellm-helm/tests/collector_tests.yaml
new file mode 100644
index 00000000000..0340b1161b7
--- /dev/null
+++ b/helm/litellm-helm/tests/collector_tests.yaml
@@ -0,0 +1,272 @@
+suite: test collector sidecar
+templates:
+  - deployment.yaml
+  - hpa.yaml
+  - configmap-litellm.yaml
+tests:
+  - it: should run the proxy alone with no collector env by default
+    template: deployment.yaml
+    asserts:
+      - lengthEqual:
+          path: spec.template.spec.containers
+          count: 1
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ENABLED
+            value: "true"
+      - notContains:
+          path: spec.template.spec.volumes
+          content:
+            name: collector-socket
+          any: true
+
+  - it: should add the sidecar on the same image and point both containers at the unix socket
+    template: deployment.yaml
+    set:
+      image.tag: test
+      db.connectionPool.enabled: true
+      collector.enabled: true
+      collector.resources:
+        requests:
+          cpu: 500m
+          memory: 1Gi
+        limits:
+          cpu: "1"
+          memory: 2Gi
+    asserts:
+      - lengthEqual:
+          path: spec.template.spec.containers
+          count: 2
+      - equal:
+          path: spec.template.spec.containers[1].name
+          value: litellm-collector
+      - equal:
+          path: spec.template.spec.containers[1].image
+          value: ghcr.io/berriai/litellm:test
+      - equal:
+          path: spec.template.spec.containers[1].command
+          value: [python, -m, litellm.proxy.collector]
+      - equal:
+          path: spec.template.spec.containers[1].resources.requests.cpu
+          value: 500m
+      - equal:
+          path: spec.template.spec.containers[1].resources.limits.memory
+          value: 2Gi
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ADDRESS
+            value: unix:///var/run/litellm/collector.sock
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_BUFFER_SIZE
+            value: "1000"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ON_UNAVAILABLE
+            value: fallback
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_JOB_ROLE
+            value: collector
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_JOB_ROLE
+            value: collector
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_COLLECTOR_ADDRESS
+            value: unix:///var/run/litellm/collector.sock
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: CONFIG_FILE_PATH
+            value: /etc/litellm/config.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: DATABASE_HOST
+            value: RELEASE-NAME-postgresql
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: DATABASE_PASSWORD
+            valueFrom:
+              secretKeyRef:
+                name: RELEASE-NAME-litellm-dbcredentials
+                key: password
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "20"
+      - contains:
+          path: spec.template.spec.containers[0].volumeMounts
+          content:
+            name: collector-socket
+            mountPath: /var/run/litellm
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: collector-socket
+            mountPath: /var/run/litellm
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: litellm-config
+            mountPath: /etc/litellm/config.yaml
+            subPath: config.yaml
+      - contains:
+          path: spec.template.spec.volumes
+          content:
+            name: collector-socket
+            emptyDir:
+              sizeLimit: 1Mi
+
+  - it: should skip the socket volume and pass the policy through on tcp transport
+    template: deployment.yaml
+    set:
+      collector.enabled: true
+      collector.address: tcp://127.0.0.1:4100
+      collector.onUnavailable: drop
+      collector.bufferSize: 50
+      envVars:
+        CONFIG_FILE_PATH: /custom/config.yaml
+    asserts:
+      - lengthEqual:
+          path: spec.template.spec.containers
+          count: 2
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: CONFIG_FILE_PATH
+            value: /etc/litellm/config.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: CONFIG_FILE_PATH
+            value: /custom/config.yaml
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ADDRESS
+            value: tcp://127.0.0.1:4100
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ON_UNAVAILABLE
+            value: drop
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_BUFFER_SIZE
+            value: "50"
+      - notContains:
+          path: spec.template.spec.volumes
+          content:
+            name: collector-socket
+          any: true
+
+  - it: should keep metrics and billing env on the proxy container only
+    template: deployment.yaml
+    set:
+      collector.enabled: true
+      metricsServer.enabled: true
+      metricsServer.port: 9090
+      billingMetrics.enabled: true
+      billingMetrics.endpoint: https://metering.example.com
+      billingMetrics.secretName: billing-mtls
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: PROMETHEUS_METRICS_PORT
+            value: "9090"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_BILLING_METRICS_ENDPOINT
+            value: https://metering.example.com
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: PROMETHEUS_METRICS_PORT
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_BILLING_METRICS_ENDPOINT
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: billing-metrics-mtls
+          any: true
+
+  - it: should give the sidecar the same scratch mounts as the proxy on a read-only root
+    template: deployment.yaml
+    set:
+      collector.enabled: true
+      securityContext.readOnlyRootFilesystem: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: npm
+            mountPath: /.npm
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: cache
+            mountPath: /.cache
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: tmp
+            mountPath: /tmp
+
+  - it: should keep the pod-wide cpu metric unless asked to scale on the proxy container
+    template: hpa.yaml
+    set:
+      autoscaling.enabled: true
+      collector.enabled: true
+    asserts:
+      - equal: { path: "spec.metrics[0].type", value: Resource }
+      - equal: { path: "spec.metrics[0].resource.name", value: cpu }
+
+  - it: should scale on the proxy container's cpu only when opted in
+    template: hpa.yaml
+    set:
+      autoscaling.enabled: true
+      collector.enabled: true
+      collector.scaleOnProxyContainerCpu: true
+    asserts:
+      - equal: { path: "spec.metrics[0].type", value: ContainerResource }
+      - equal: { path: "spec.metrics[0].containerResource.name", value: cpu }
+      - equal: { path: "spec.metrics[0].containerResource.container", value: litellm }
+      - equal: { path: "spec.metrics[0].containerResource.target.averageUtilization", value: 60 }
+      - isNull: { path: "spec.metrics[0].resource" }
+
+  - it: should not switch to the container metric while the sidecar is off
+    template: hpa.yaml
+    set:
+      autoscaling.enabled: true
+      collector.scaleOnProxyContainerCpu: true
+    asserts:
+      - equal: { path: "spec.metrics[0].type", value: Resource }
diff --git a/helm/litellm-helm/tests/connection_pool_tests.yaml b/helm/litellm-helm/tests/connection_pool_tests.yaml
new file mode 100644
index 00000000000..203082f27ba
--- /dev/null
+++ b/helm/litellm-helm/tests/connection_pool_tests.yaml
@@ -0,0 +1,112 @@
+suite: test in-container connection pool
+templates:
+  - deployment.yaml
+  - configmap-litellm.yaml
+tests:
+  - it: should not emit pgbouncer env vars by default
+    template: deployment.yaml
+    asserts:
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "20"
+
+  - it: should enable the pool with the default sizing when connectionPool.enabled is set
+    template: deployment.yaml
+    set:
+      db.connectionPool.enabled: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "20"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "1000"
+
+  - it: should pass custom sizing through as strings next to the worker count
+    template: deployment.yaml
+    set:
+      numWorkers: 4
+      db.connectionPool.enabled: true
+      db.connectionPool.maxDbConnections: 8
+      db.connectionPool.maxClientConn: 400
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "8"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "400"
+      - contains:
+          path: spec.template.spec.containers[0].args
+          content: "4"
+
+  - it: should give the collector sidecar the same pool env as the proxy container
+    template: deployment.yaml
+    set:
+      collector.enabled: true
+      db.connectionPool.enabled: true
+      db.connectionPool.maxDbConnections: 8
+      db.connectionPool.maxClientConn: 400
+    asserts:
+      - equal:
+          path: spec.template.spec.containers[1].name
+          value: litellm-collector
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "8"
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "400"
+
+  - it: should give the collector sidecar no pool env when the pool is off
+    template: deployment.yaml
+    set:
+      collector.enabled: true
+    asserts:
+      - equal:
+          path: spec.template.spec.containers[1].name
+          value: litellm-collector
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+          any: true
diff --git a/helm/litellm-helm/tests/hpa_tests.yaml b/helm/litellm-helm/tests/hpa_tests.yaml
index cd062dd5971..e446f58c8fe 100644
--- a/helm/litellm-helm/tests/hpa_tests.yaml
+++ b/helm/litellm-helm/tests/hpa_tests.yaml
@@ -61,6 +61,84 @@ tests:
       - equal: { path: "spec.metrics[1].resource.name", value: memory }
       - equal: { path: "spec.metrics[1].resource.target.averageUtilization", value: 80 }
 
+  - it: "renders no workload metrics by default"
+    set:
+      autoscaling.enabled: true
+      autoscaling.targetMemoryUtilizationPercentage: 80
+    asserts:
+      - lengthEqual: { path: spec.metrics, count: 2 }
+      - notContains: { path: spec.metrics, content: { type: Pods }, any: true }
+
+  - it: "adds a requests-per-second Pods metric after the cpu metric"
+    set:
+      autoscaling.enabled: true
+      autoscaling.targetRequestsPerSecond: 90
+    asserts:
+      - lengthEqual: { path: spec.metrics, count: 2 }
+      - equal: { path: "spec.metrics[0].resource.name", value: cpu }
+      - equal:
+          path: "spec.metrics[1]"
+          value:
+            type: Pods
+            pods:
+              metric: { name: litellm_requests_per_second }
+              target: { type: AverageValue, averageValue: "90" }
+
+  - it: "adds a tokens-per-second Pods metric on its own"
+    set:
+      autoscaling.enabled: true
+      autoscaling.targetTokensPerSecond: 6M
+    asserts:
+      - lengthEqual: { path: spec.metrics, count: 2 }
+      - equal:
+          path: "spec.metrics[1]"
+          value:
+            type: Pods
+            pods:
+              metric: { name: litellm_tokens_per_second }
+              target: { type: AverageValue, averageValue: "6M" }
+      - notContains:
+          path: spec.metrics
+          content: { type: Pods, pods: { metric: { name: litellm_requests_per_second } } }
+          any: true
+
+  - it: "renders requests, tokens, cpu and memory metrics together"
+    set:
+      autoscaling.enabled: true
+      autoscaling.targetMemoryUtilizationPercentage: 80
+      autoscaling.targetRequestsPerSecond: 90
+      autoscaling.targetTokensPerSecond: 6000000
+    asserts:
+      - lengthEqual: { path: spec.metrics, count: 4 }
+      - equal: { path: "spec.metrics[0].resource.name", value: cpu }
+      - equal: { path: "spec.metrics[1].resource.name", value: memory }
+      - equal: { path: "spec.metrics[2].pods.metric.name", value: litellm_requests_per_second }
+      - equal: { path: "spec.metrics[2].pods.target.averageValue", value: "90" }
+      - equal: { path: "spec.metrics[3].pods.metric.name", value: litellm_tokens_per_second }
+      - equal: { path: "spec.metrics[3].pods.target.averageValue", value: "6000000" }
+
+  - it: "scales on workload metrics alone when the cpu target is cleared"
+    set:
+      autoscaling.enabled: true
+      autoscaling.targetCPUUtilizationPercentage: null
+      autoscaling.targetRequestsPerSecond: 90
+      autoscaling.targetTokensPerSecond: 6000000
+    asserts:
+      - lengthEqual: { path: spec.metrics, count: 2 }
+      - notContains: { path: spec.metrics, content: { type: Resource }, any: true }
+      - equal: { path: "spec.metrics[0].pods.metric.name", value: litellm_requests_per_second }
+      - equal: { path: "spec.metrics[1].pods.metric.name", value: litellm_tokens_per_second }
+      - notMatchRegexRaw: { pattern: per_minute }
+
+  - it: "ignores the per-minute keys, which the chart never shipped"
+    set:
+      autoscaling.enabled: true
+      autoscaling.targetRequestsPerMinute: 5400
+      autoscaling.targetTokensPerMinute: 360000000
+    asserts:
+      - lengthEqual: { path: spec.metrics, count: 1 }
+      - notContains: { path: spec.metrics, content: { type: Pods }, any: true }
+
   - it: "renders no hpa when autoscaling is disabled"
     asserts:
       - hasDocuments: { count: 0 }
diff --git a/helm/litellm-helm/tests/keda_tests.yaml b/helm/litellm-helm/tests/keda_tests.yaml
new file mode 100644
index 00000000000..c9598646223
--- /dev/null
+++ b/helm/litellm-helm/tests/keda_tests.yaml
@@ -0,0 +1,106 @@
+suite: "keda"
+templates:
+  - keda.yaml
+release:
+  name: rel
+  namespace: llm
+tests:
+  - it: "renders no scaled object by default"
+    asserts:
+      - hasDocuments: { count: 0 }
+
+  - it: "passes user triggers through and adds no prometheus triggers by default"
+    set:
+      keda.enabled: true
+      keda.triggers:
+        - type: cpu
+          metricType: Utilization
+          metadata: { value: "60" }
+    asserts:
+      - isKind: { of: ScaledObject }
+      - equal:
+          path: spec.triggers
+          value:
+            - type: cpu
+              metricType: Utilization
+              metadata: { value: "60" }
+
+  - it: "scales on release-wide requests per second divided by the per-replica target"
+    set:
+      keda.enabled: true
+      keda.prometheus.serverAddress: http://prometheus-operated.monitoring.svc:9090
+      keda.prometheus.requestsPerSecond: 90
+    asserts:
+      - lengthEqual: { path: spec.triggers, count: 1 }
+      - equal:
+          path: "spec.triggers[0]"
+          value:
+            type: prometheus
+            metadata:
+              serverAddress: http://prometheus-operated.monitoring.svc:9090
+              threshold: "90"
+              query: sum(rate(litellm_proxy_total_requests_metric_total{namespace="llm",job="rel-litellm"}[1m]))
+
+  - it: "scales on tokens per second on its own"
+    set:
+      keda.enabled: true
+      keda.prometheus.serverAddress: http://prom:9090
+      keda.prometheus.tokensPerSecond: 6000000
+    asserts:
+      - lengthEqual: { path: spec.triggers, count: 1 }
+      - equal: { path: "spec.triggers[0].type", value: prometheus }
+      - equal: { path: "spec.triggers[0].metadata.threshold", value: "6000000" }
+      - equal:
+          path: "spec.triggers[0].metadata.query"
+          value: sum(rate(litellm_total_tokens_metric_total{namespace="llm",job="rel-litellm"}[1m]))
+
+  - it: "appends requests and tokens triggers after user triggers and selects the metrics service job"
+    set:
+      keda.enabled: true
+      metricsServer.enabled: true
+      keda.triggers:
+        - type: cpu
+          metricType: Utilization
+          metadata: { value: "60" }
+      keda.prometheus.serverAddress: http://prom:9090
+      keda.prometheus.requestsPerSecond: 90
+      keda.prometheus.tokensPerSecond: 6000000
+    asserts:
+      - lengthEqual: { path: spec.triggers, count: 3 }
+      - equal: { path: "spec.triggers[0].type", value: cpu }
+      - equal: { path: "spec.triggers[1].metadata.threshold", value: "90" }
+      - equal:
+          path: "spec.triggers[1].metadata.query"
+          value: sum(rate(litellm_proxy_total_requests_metric_total{namespace="llm",job="rel-litellm-metrics"}[1m]))
+      - equal: { path: "spec.triggers[2].metadata.threshold", value: "6000000" }
+      - equal:
+          path: "spec.triggers[2].metadata.query"
+          value: sum(rate(litellm_total_tokens_metric_total{namespace="llm",job="rel-litellm-metrics"}[1m]))
+      - notMatchRegexRaw: { pattern: "\\* *60|per_minute|PerMinute" }
+
+  - it: "ignores the per-minute keys, which the chart never shipped"
+    set:
+      keda.enabled: true
+      keda.prometheus.serverAddress: http://prom:9090
+      keda.prometheus.requestsPerMinute: 5400
+      keda.prometheus.tokensPerMinute: 360000000
+    asserts:
+      - isKind: { of: ScaledObject }
+      - isNullOrEmpty: { path: spec.triggers }
+
+  - it: "refuses a workload target without a prometheus server address"
+    set:
+      keda.enabled: true
+      keda.prometheus.requestsPerSecond: 90
+    asserts:
+      - failedTemplate:
+          errorMessage: keda.prometheus.serverAddress is required when keda.prometheus.requestsPerSecond or tokensPerSecond is set
+
+  - it: "yields to the hpa when both autoscalers are enabled"
+    set:
+      autoscaling.enabled: true
+      keda.enabled: true
+      keda.prometheus.serverAddress: http://prom:9090
+      keda.prometheus.requestsPerSecond: 90
+    asserts:
+      - hasDocuments: { count: 0 }
diff --git a/helm/litellm-helm/values.yaml b/helm/litellm-helm/values.yaml
index 8dc7b967e11..fcee331a5aa 100644
--- a/helm/litellm-helm/values.yaml
+++ b/helm/litellm-helm/values.yaml
@@ -190,6 +190,48 @@ metricsServer:
   enabled: false
   port: 4001
 
+# Opt-in sidecar that runs the post-response spend pipeline (cost calculation,
+# spend logs, spend counters, budget reservation reconciliation) so the proxy's
+# uvicorn workers only serialise a compact typed event and go back to serving
+# inference. Same image and tag as the proxy, second container in the same pod,
+# fed over loopback (a unix socket on a shared emptyDir, or 127.0.0.1 TCP). It
+# reuses the pod's in-container pgbouncer (db.connectionPool) and the same Redis
+# spend transaction buffer, so the per-pod DB connection budget is unchanged.
+# Delivery is at-most-once inside the pod: events already handed to the sidecar
+# are lost if it crashes before writing them; events the workers could not hand
+# over follow onUnavailable. Both containers drain on SIGTERM within
+# terminationGracePeriodSeconds
+collector:
+  enabled: false
+  # unix:///<dir>/<file>.sock (the <dir> becomes a shared emptyDir) or tcp://127.0.0.1:<port>
+  address: unix:///var/run/litellm/collector.sock
+  # Events each uvicorn worker holds in memory while the sidecar is slow or restarting
+  bufferSize: 1000
+  # fallback: run the pipeline in the worker when the sidecar is unreachable or the
+  # buffer is full (spend stays exact, that request costs proxy CPU again)
+  # drop: count and discard the event instead (spend under-reports)
+  onUnavailable: fallback
+  # How long the workers keep pushing buffered events on shutdown, and how long the
+  # sidecar keeps serving its open connections after SIGTERM
+  drainTimeoutSeconds: 10
+  command:
+    - python
+    - -m
+    - litellm.proxy.collector
+  # Sized independently of the proxy container; the pipeline is CPU bound
+  resources: {}
+  # requests:
+  #   cpu: 500m
+  #   memory: 1Gi
+  # limits:
+  #   cpu: "1"
+  #   memory: 2Gi
+  # When autoscaling.enabled, swap the pod-wide cpu Resource metric for an
+  # autoscaling/v2 ContainerResource metric on the proxy container only, so the
+  # sidecar's CPU never scales inference replicas. Needs Kubernetes 1.30+ (or the
+  # HPAContainerMetrics feature gate on 1.27 to 1.29)
+  scaleOnProxyContainerCpu: false
+
 resources:
   {}
   # Unset by default so the chart installs on small clusters such as Minikube, and so an
@@ -222,6 +264,25 @@ autoscaling:
   # Memory is a floor to provision under 'resources', not a signal to scale on.
   # targetMemoryUtilizationPercentage: 80
   # behavior: {}
+  # Opt-in per-pod workload targets, rendered as autoscaling/v2 `Pods` metrics
+  # named `litellm_requests_per_second` and `litellm_tokens_per_second` with an
+  # AverageValue target, alongside whichever resource targets are set (the HPA
+  # follows the metric asking for the most replicas). A Prometheus Adapter must
+  # serve those two names on custom.metrics.k8s.io from the proxy's counters,
+  # grouped by the scrape target's `pod` label (enable serviceMonitor below so
+  # every pod is scraped on its own):
+  #   litellm_requests_per_second:
+  #     sum(rate(litellm_proxy_total_requests_metric_total{<<.LabelMatchers>>}[1m])) by (<<.GroupBy>>)
+  #   litellm_tokens_per_second:
+  #     sum(rate(litellm_total_tokens_metric_total{<<.LabelMatchers>>}[1m])) by (<<.GroupBy>>)
+  # rate() over [1m] is already per second, so no `* 60`. How fast the HPA
+  # reacts is set by that window, the scrape interval and the HPA sync period
+  # (15s by default), not by the unit: keep serviceMonitor.interval at 15s or
+  # faster so a 1m window holds at least 4 samples. averageValue takes SI
+  # suffixes, so "6M" is six million tokens per second per pod. Tokens are
+  # counted when a response completes, so TPS trails long streams.
+  targetRequestsPerSecond: ""
+  targetTokensPerSecond: ""
 
 # Autoscaling with keda is mutually exclusive with hpa
 keda:
@@ -243,6 +304,23 @@ keda:
   #     metricName: http_requests_total
   #     threshold: '100'
   #     query: sum(rate(http_requests_total{deployment="my-deployment"}[2m]))
+  # First-class Prometheus triggers on the proxy's own request and token
+  # counters, appended to `triggers`. Each target is the per-second load one
+  # replica should carry: KEDA divides the release-wide
+  # `sum(rate(<counter>[1m]))` by it to pick the replica count. Thresholds
+  # are plain numbers (KEDA parses them as floats, no SI suffixes). The
+  # queries select samples by the release namespace and the `job` label the
+  # chart's ServiceMonitor produces (the metrics Service name), so enable
+  # serviceMonitor below together with metricsServer: the http port serves
+  # /metrics/ behind virtual-key auth and answers an unauthenticated scrape
+  # with 401. Reaction time comes from the [1m] window, the scrape interval
+  # and pollingInterval above, so keep both at 15s or faster. Tokens are
+  # counted at completion, so TPS trails long streams. serverAddress is
+  # required once either target is set.
+  prometheus:
+    serverAddress: ""
+    requestsPerSecond: ""
+    tokensPerSecond: ""
   behavior: {}
   # scaleDown:
   #   stabilizationWindowSeconds: 300
@@ -319,6 +397,20 @@ db:
   # only (e.g. when IAM_TOKEN_DB_AUTH supplies the token at runtime).
   readReplicaUrl: ""
 
+  # In-container connection pool (PgBouncer, transaction mode) shared by every
+  # worker in the pod. Without it each --num_workers worker opens its own
+  # connection_limit connections to Postgres, so a pod's footprint against the
+  # database's connection ceiling is workers x connection_limit and grows with
+  # every replica. With it, the pod holds at most maxDbConnections upstream
+  # connections no matter how many workers run; the workers connect to the pool
+  # over loopback, with no extra network hop. Migrations still go straight to
+  # Postgres. Starting profile for numWorkers: 4 is maxDbConnections: 20, so
+  # a database with a 5000-connection ceiling fits roughly 200 replicas.
+  connectionPool:
+    enabled: false
+    maxDbConnections: 20
+    maxClientConn: 1000
+
   # Use the Stackgres Helm chart to deploy an instance of a Stackgres cluster.
   #  The Stackgres Operator must already be installed within the target
   #  Kubernetes cluster.
diff --git a/helm/litellm/templates/_helpers.tpl b/helm/litellm/templates/_helpers.tpl
index c459512c7b9..692a799e783 100644
--- a/helm/litellm/templates/_helpers.tpl
+++ b/helm/litellm/templates/_helpers.tpl
@@ -360,6 +360,20 @@ harmless no-op for the Job and authoritative for the app pods.
 {{- end }}
 {{- end -}}
 
+{{/*
+In-container PgBouncer env for the gateway container. Under IAM or Entra auth the pooler mints and renews the database token itself.
+*/}}
+{{- define "litellm.connectionPoolEnv" -}}
+{{- with .Values.database.connectionPool -}}
+- name: LITELLM_PGBOUNCER_ENABLED
+  value: "true"
+- name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+  value: {{ required "database.connectionPool.maxDbConnections is required when the pool is enabled" .maxDbConnections | quote }}
+- name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+  value: {{ required "database.connectionPool.maxClientConn is required when the pool is enabled" .maxClientConn | quote }}
+{{- end }}
+{{- end -}}
+
 {{/*
 PodDisruptionBudget shared by gateway, backend, and ui.
 
@@ -443,3 +457,34 @@ ImplementationSpecific
 {{- end -}}
 
 {{- define "litellm.gateway.prometheusMultiprocDir" -}}/tmp/litellm_prometheus_multiproc{{- end -}}
+
+{{/*
+Directory of the collector's unix socket, shared by the gateway and
+collector containers through an emptyDir. Empty when the sidecar is off
+or gateway.collector.address is a tcp://127.0.0.1:<port> address.
+*/}}
+{{- define "litellm.gateway.collectorSocketDir" -}}
+{{- if and .Values.gateway.collector.enabled (hasPrefix "unix://" .Values.gateway.collector.address) -}}
+{{- dir (trimPrefix "unix://" .Values.gateway.collector.address) -}}
+{{- end -}}
+{{- end -}}
+
+{{/*
+LITELLM_COLLECTOR_* env shared by the producer (gateway container) and the
+consumer (collector container), so both agree on the transport and the
+shutdown drain window.
+*/}}
+{{- define "litellm.gateway.collectorEnv" -}}
+{{- with .Values.gateway.collector }}
+- name: LITELLM_COLLECTOR_ENABLED
+  value: "true"
+- name: LITELLM_COLLECTOR_ADDRESS
+  value: {{ .address | quote }}
+- name: LITELLM_COLLECTOR_BUFFER_SIZE
+  value: {{ .bufferSize | quote }}
+- name: LITELLM_COLLECTOR_ON_UNAVAILABLE
+  value: {{ .onUnavailable | quote }}
+- name: LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS
+  value: {{ .drainTimeoutSeconds | quote }}
+{{- end }}
+{{- end -}}
diff --git a/helm/litellm/templates/gateway/deployment.yaml b/helm/litellm/templates/gateway/deployment.yaml
index 9cb6b07e77b..c06cc9583a0 100644
--- a/helm/litellm/templates/gateway/deployment.yaml
+++ b/helm/litellm/templates/gateway/deployment.yaml
@@ -61,6 +61,9 @@ spec:
             - name: NUM_WORKERS
               value: {{ .Values.gateway.numWorkers | quote }}
             {{- end }}
+            {{- if .Values.database.connectionPool.enabled }}
+            {{- include "litellm.connectionPoolEnv" $ | nindent 12 }}
+            {{- end }}
             {{- if .Values.billingMetrics.enabled }}
             {{- include "litellm.billingMetricsEnv" . | nindent 12 }}
             {{- end }}
@@ -71,8 +74,11 @@ spec:
             - name: PROMETHEUS_MULTIPROC_DIR
               value: {{ include "litellm.gateway.prometheusMultiprocDir" . }}
             {{- end }}
+            {{- if .Values.gateway.collector.enabled }}
+            {{- include "litellm.gateway.collectorEnv" . | nindent 12 }}
+            {{- end }}
           {{- include "litellm.envFrom" .Values.gateway | nindent 10 }}
-          {{- if or .Values.gateway.config.create .Values.gateway.volumeMounts .Values.billingMetrics.enabled .Values.gateway.metricsServer.enabled }}
+          {{- if or .Values.gateway.config.create .Values.gateway.volumeMounts .Values.billingMetrics.enabled .Values.gateway.metricsServer.enabled (include "litellm.gateway.collectorSocketDir" .) }}
           volumeMounts:
             {{- if .Values.gateway.config.create }}
             - name: gateway-config
@@ -83,6 +89,10 @@ spec:
             - name: prometheus-multiproc
               mountPath: {{ include "litellm.gateway.prometheusMultiprocDir" . }}
             {{- end }}
+            {{- if include "litellm.gateway.collectorSocketDir" . }}
+            - name: collector-socket
+              mountPath: {{ include "litellm.gateway.collectorSocketDir" . }}
+            {{- end }}
             {{- if .Values.billingMetrics.enabled }}
             {{- include "litellm.billingMetricsVolumeMounts" . | nindent 12 }}
             {{- end }}
@@ -142,10 +152,53 @@ spec:
           resources:
             {{- toYaml .Values.gateway.metricsServer.resources | nindent 12 }}
         {{- end }}
+        {{- if .Values.gateway.collector.enabled }}
+        - name: collector
+          image: "{{ .Values.gateway.image.repository }}:{{ .Values.gateway.image.tag | default .Chart.AppVersion }}"
+          imagePullPolicy: {{ .Values.gateway.image.pullPolicy }}
+          {{- with .Values.gateway.securityContext }}
+          securityContext:
+            {{- toYaml . | nindent 12 }}
+          {{- end }}
+          command:
+            - python
+            - -m
+            - litellm.proxy.collector
+          env:
+            {{- include "litellm.serverEnv" (dict "root" $ "component" .Values.gateway) | nindent 12 }}
+            {{- if .Values.gateway.config.create }}
+            - name: CONFIG_FILE_PATH
+              value: /app/config/config.yaml
+            {{- end }}
+            {{- if .Values.database.connectionPool.enabled }}
+            {{- include "litellm.connectionPoolEnv" $ | nindent 12 }}
+            {{- end }}
+            {{- include "litellm.gateway.collectorEnv" . | nindent 12 }}
+            - name: LITELLM_JOB_ROLE
+              value: collector
+          {{- include "litellm.envFrom" .Values.gateway | nindent 10 }}
+          {{- if or .Values.gateway.config.create .Values.gateway.volumeMounts (include "litellm.gateway.collectorSocketDir" .) }}
+          volumeMounts:
+            {{- if .Values.gateway.config.create }}
+            - name: gateway-config
+              mountPath: /app/config/config.yaml
+              subPath: config.yaml
+            {{- end }}
+            {{- if include "litellm.gateway.collectorSocketDir" . }}
+            - name: collector-socket
+              mountPath: {{ include "litellm.gateway.collectorSocketDir" . }}
+            {{- end }}
+            {{- with .Values.gateway.volumeMounts }}
+            {{- toYaml . | nindent 12 }}
+            {{- end }}
+          {{- end }}
+          resources:
+            {{- toYaml .Values.gateway.collector.resources | nindent 12 }}
+        {{- end }}
       {{- with .Values.gateway.extraContainers }}
         {{- tpl (toYaml .) $ | nindent 8 }}
       {{- end }}
-      {{- if or .Values.gateway.config.create .Values.gateway.volumes .Values.billingMetrics.enabled .Values.gateway.metricsServer.enabled }}
+      {{- if or .Values.gateway.config.create .Values.gateway.volumes .Values.billingMetrics.enabled .Values.gateway.metricsServer.enabled (include "litellm.gateway.collectorSocketDir" .) }}
       volumes:
         {{- if .Values.gateway.config.create }}
         - name: gateway-config
@@ -156,6 +209,11 @@ spec:
         - name: prometheus-multiproc
           emptyDir: {}
         {{- end }}
+        {{- if include "litellm.gateway.collectorSocketDir" . }}
+        - name: collector-socket
+          emptyDir:
+            sizeLimit: 1Mi
+        {{- end }}
         {{- if .Values.billingMetrics.enabled }}
         {{- include "litellm.billingMetricsVolumes" . | nindent 8 }}
         {{- end }}
diff --git a/helm/litellm/templates/gateway/hpa.yaml b/helm/litellm/templates/gateway/hpa.yaml
index e97cef95ffb..e7094e96106 100644
--- a/helm/litellm/templates/gateway/hpa.yaml
+++ b/helm/litellm/templates/gateway/hpa.yaml
@@ -15,6 +15,15 @@ spec:
   maxReplicas: {{ .Values.gateway.hpa.maxReplicas }}
   metrics:
     {{- if .Values.gateway.hpa.targetCPUUtilizationPercentage }}
+    {{- if and .Values.gateway.collector.enabled .Values.gateway.collector.scaleOnGatewayContainerCpu }}
+    - type: ContainerResource
+      containerResource:
+        name: cpu
+        container: gateway
+        target:
+          type: Utilization
+          averageUtilization: {{ .Values.gateway.hpa.targetCPUUtilizationPercentage }}
+    {{- else }}
     - type: Resource
       resource:
         name: cpu
@@ -22,6 +31,7 @@ spec:
           type: Utilization
           averageUtilization: {{ .Values.gateway.hpa.targetCPUUtilizationPercentage }}
     {{- end }}
+    {{- end }}
     {{- if .Values.gateway.hpa.targetMemoryUtilizationPercentage }}
     - type: Resource
       resource:
@@ -30,6 +40,24 @@ spec:
           type: Utilization
           averageUtilization: {{ .Values.gateway.hpa.targetMemoryUtilizationPercentage }}
     {{- end }}
+    {{- with .Values.gateway.hpa.targetRequestsPerSecond }}
+    - type: Pods
+      pods:
+        metric:
+          name: litellm_requests_per_second
+        target:
+          type: AverageValue
+          averageValue: {{ toJson . | trimAll "\"" | quote }}
+    {{- end }}
+    {{- with .Values.gateway.hpa.targetTokensPerSecond }}
+    - type: Pods
+      pods:
+        metric:
+          name: litellm_tokens_per_second
+        target:
+          type: AverageValue
+          averageValue: {{ toJson . | trimAll "\"" | quote }}
+    {{- end }}
   {{- with .Values.gateway.hpa.behavior }}
   behavior:
     {{- toYaml . | nindent 4 }}
diff --git a/helm/litellm/templates/gateway/servicemonitor.yaml b/helm/litellm/templates/gateway/servicemonitor.yaml
new file mode 100644
index 00000000000..e1bafa6e388
--- /dev/null
+++ b/helm/litellm/templates/gateway/servicemonitor.yaml
@@ -0,0 +1,28 @@
+{{- if and .Values.gateway.enabled .Values.gateway.serviceMonitor.enabled }}
+{{- if not .Values.gateway.metricsServer.enabled }}
+{{- fail "gateway.serviceMonitor.enabled requires gateway.metricsServer.enabled: the http port serves /metrics/ behind virtual-key auth, so an unauthenticated scrape gets 401" }}
+{{- end }}
+apiVersion: monitoring.coreos.com/v1
+kind: ServiceMonitor
+metadata:
+  name: {{ include "litellm.gateway.fullname" . }}
+  labels:
+    {{- include "litellm.commonLabels" . | nindent 4 }}
+    app.kubernetes.io/component: gateway
+    {{- with .Values.gateway.serviceMonitor.labels }}
+    {{- toYaml . | nindent 4 }}
+    {{- end }}
+spec:
+  selector:
+    matchLabels:
+      {{- include "litellm.gateway.selectorLabels" . | nindent 6 }}
+  namespaceSelector:
+    matchNames:
+      - {{ .Release.Namespace | quote }}
+  endpoints:
+    - port: metrics
+      path: /metrics/
+      interval: {{ .Values.gateway.serviceMonitor.interval }}
+      scrapeTimeout: {{ .Values.gateway.serviceMonitor.scrapeTimeout }}
+      scheme: http
+{{- end }}
diff --git a/helm/litellm/tests/collector_tests.yaml b/helm/litellm/tests/collector_tests.yaml
new file mode 100644
index 00000000000..4ef7e3c8ca4
--- /dev/null
+++ b/helm/litellm/tests/collector_tests.yaml
@@ -0,0 +1,216 @@
+suite: test gateway collector sidecar
+templates:
+  - gateway/configmap.yaml
+  - gateway/deployment.yaml
+  - gateway/hpa.yaml
+values:
+  - ./values/required.yaml
+tests:
+  - it: adds no sidecar, env, volume or container metric when the collector is off
+    asserts:
+      - lengthEqual:
+          path: spec.template.spec.containers
+          count: 1
+        template: gateway/deployment.yaml
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ENABLED
+            value: "true"
+        template: gateway/deployment.yaml
+      - notContains:
+          path: spec.template.spec.volumes
+          content:
+            name: collector-socket
+          any: true
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.metrics[0].type
+          value: Resource
+        template: gateway/hpa.yaml
+
+  - it: runs the collector as a sidecar sharing env, config, the pod pool and a unix socket emptyDir, and scales on the gateway container only
+    set:
+      gateway.collector.enabled: true
+      gateway.collector.bufferSize: 250
+      gateway.collector.onUnavailable: drop
+      gateway.image.tag: v1.102.0
+      gateway.numWorkers: 4
+      database.connectionPool.enabled: true
+      database.connectionPool.maxDbConnections: 8
+      database.connectionPool.maxClientConn: 250
+      gateway.envSecrets:
+        - litellm-license
+      gateway.volumes:
+        - name: redis-ca
+          secret:
+            secretName: redis-ca
+      gateway.volumeMounts:
+        - name: redis-ca
+          mountPath: /etc/litellm/redis-ca
+          readOnly: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ADDRESS
+            value: unix:///var/run/litellm/collector.sock
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_BUFFER_SIZE
+            value: "250"
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_COLLECTOR_ON_UNAVAILABLE
+            value: drop
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[0].volumeMounts
+          content:
+            name: collector-socket
+            mountPath: /var/run/litellm
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.template.spec.containers[1].name
+          value: collector
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.template.spec.containers[1].image
+          value: ghcr.io/berriai/litellm-gateway:v1.102.0
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.template.spec.containers[1].command
+          value:
+            - python
+            - -m
+            - litellm.proxy.collector
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_JOB_ROLE
+            value: collector
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: CONFIG_FILE_PATH
+            value: /app/config/config.yaml
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "8"
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "250"
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: DATABASE_HOST
+            value: postgres.example.com
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_COLLECTOR_ADDRESS
+            value: unix:///var/run/litellm/collector.sock
+        template: gateway/deployment.yaml
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: NUM_WORKERS
+          any: true
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.template.spec.containers[1].envFrom
+          value:
+            - secretRef:
+                name: litellm-license
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: gateway-config
+            mountPath: /app/config/config.yaml
+            subPath: config.yaml
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: collector-socket
+            mountPath: /var/run/litellm
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: redis-ca
+            mountPath: /etc/litellm/redis-ca
+            readOnly: true
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.template.spec.containers[1].resources.limits.cpu
+          value: "1"
+        template: gateway/deployment.yaml
+      - contains:
+          path: spec.template.spec.volumes
+          content:
+            name: collector-socket
+            emptyDir:
+              sizeLimit: 1Mi
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.metrics[0]
+          value:
+            type: ContainerResource
+            containerResource:
+              name: cpu
+              container: gateway
+              target:
+                type: Utilization
+                averageUtilization: 70
+        template: gateway/hpa.yaml
+
+  - it: uses loopback tcp without a socket volume and keeps the pod-wide cpu metric when asked
+    set:
+      gateway.collector.enabled: true
+      gateway.collector.address: tcp://127.0.0.1:4010
+      gateway.collector.scaleOnGatewayContainerCpu: false
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_COLLECTOR_ADDRESS
+            value: tcp://127.0.0.1:4010
+        template: gateway/deployment.yaml
+      - notContains:
+          path: spec.template.spec.volumes
+          content:
+            name: collector-socket
+          any: true
+        template: gateway/deployment.yaml
+      - notContains:
+          path: spec.template.spec.containers[1].volumeMounts
+          content:
+            name: collector-socket
+          any: true
+        template: gateway/deployment.yaml
+      - equal:
+          path: spec.metrics[0].type
+          value: Resource
+        template: gateway/hpa.yaml
diff --git a/helm/litellm/tests/connection_pool_tests.yaml b/helm/litellm/tests/connection_pool_tests.yaml
new file mode 100644
index 00000000000..c39651a52c9
--- /dev/null
+++ b/helm/litellm/tests/connection_pool_tests.yaml
@@ -0,0 +1,204 @@
+suite: test in-container connection pool env vars
+templates:
+  - gateway/deployment.yaml
+  - gateway/configmap.yaml
+  - backend/deployment.yaml
+  - backend/configmap.yaml
+values:
+  - ./values/required.yaml
+tests:
+  - it: renders no pool env by default
+    template: gateway/deployment.yaml
+    asserts:
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+          any: true
+
+  - it: enabled pool renders the three pgbouncer vars with the configured sizes
+    template: gateway/deployment.yaml
+    set:
+      gateway.numWorkers: 4
+      database.connectionPool.enabled: true
+      database.connectionPool.maxDbConnections: 8
+      database.connectionPool.maxClientConn: 250
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "8"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "250"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: NUM_WORKERS
+            value: "4"
+
+  - it: enabled pool uses the chart default sizes
+    template: gateway/deployment.yaml
+    set:
+      database.connectionPool.enabled: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "20"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "1000"
+
+  - it: backend never gets the pool env
+    template: backend/deployment.yaml
+    set:
+      database.connectionPool.enabled: true
+    asserts:
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+          any: true
+
+  - it: collector sidecar gets the same pool env as the gateway container, the metrics sidecar none
+    template: gateway/deployment.yaml
+    set:
+      gateway.collector.enabled: true
+      gateway.metricsServer.enabled: true
+      database.connectionPool.enabled: true
+      database.connectionPool.maxDbConnections: 8
+      database.connectionPool.maxClientConn: 250
+    asserts:
+      - equal:
+          path: spec.template.spec.containers[1].name
+          value: metrics
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+          any: true
+      - equal:
+          path: spec.template.spec.containers[2].name
+          value: collector
+      - contains:
+          path: spec.template.spec.containers[2].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[2].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+            value: "8"
+      - contains:
+          path: spec.template.spec.containers[2].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+            value: "250"
+
+  - it: collector sidecar gets no pool env when the pool is off
+    template: gateway/deployment.yaml
+    set:
+      gateway.collector.enabled: true
+    asserts:
+      - equal:
+          path: spec.template.spec.containers[1].name
+          value: collector
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS
+          any: true
+      - notContains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_MAX_CLIENT_CONN
+          any: true
+
+  - it: pool with IAM auth renders both the pool and the token auth flag
+    template: gateway/deployment.yaml
+    set:
+      gateway.collector.enabled: true
+      database.connectionPool.enabled: true
+      database.writer.useIAMAuth: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: IAM_TOKEN_DB_AUTH
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[1].env
+          content:
+            name: IAM_TOKEN_DB_AUTH
+            value: "true"
+
+  - it: pool with Entra auth renders both the pool and the token auth flag
+    template: gateway/deployment.yaml
+    set:
+      database.connectionPool.enabled: true
+      database.writer.useAzureEntraAuth: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+            value: "true"
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: AZURE_POSTGRESQL_AUTH
+            value: "true"
+
+  - it: IAM auth without the pool still renders
+    template: gateway/deployment.yaml
+    set:
+      database.writer.useIAMAuth: true
+    asserts:
+      - contains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: IAM_TOKEN_DB_AUTH
+            value: "true"
+      - notContains:
+          path: spec.template.spec.containers[0].env
+          content:
+            name: LITELLM_PGBOUNCER_ENABLED
+          any: true
diff --git a/helm/litellm/tests/hpa_workload_metrics_tests.yaml b/helm/litellm/tests/hpa_workload_metrics_tests.yaml
new file mode 100644
index 00000000000..a29c53c5ed9
--- /dev/null
+++ b/helm/litellm/tests/hpa_workload_metrics_tests.yaml
@@ -0,0 +1,213 @@
+suite: test gateway HPA per-pod requests-per-second and tokens-per-second targets
+templates:
+  - gateway/hpa.yaml
+  - gateway/servicemonitor.yaml
+values:
+  - ./values/required.yaml
+tests:
+  - it: scales on CPU and memory only by default
+    template: gateway/hpa.yaml
+    asserts:
+      - equal:
+          path: spec.metrics
+          value:
+            - type: Resource
+              resource:
+                name: cpu
+                target:
+                  type: Utilization
+                  averageUtilization: 70
+            - type: Resource
+              resource:
+                name: memory
+                target:
+                  type: Utilization
+                  averageUtilization: 80
+
+  - it: adds a requests-per-second Pods metric next to the resource metrics
+    template: gateway/hpa.yaml
+    set:
+      gateway.hpa.targetRequestsPerSecond: 90
+    asserts:
+      - lengthEqual:
+          path: spec.metrics
+          count: 3
+      - contains:
+          path: spec.metrics
+          content:
+            type: Resource
+            resource:
+              name: cpu
+              target:
+                type: Utilization
+                averageUtilization: 70
+      - equal:
+          path: spec.metrics[2]
+          value:
+            type: Pods
+            pods:
+              metric:
+                name: litellm_requests_per_second
+              target:
+                type: AverageValue
+                averageValue: "90"
+      - notContains:
+          path: spec.metrics
+          content:
+            type: Pods
+            pods:
+              metric:
+                name: litellm_tokens_per_second
+          any: true
+
+  - it: adds a tokens-per-second Pods metric on its own
+    template: gateway/hpa.yaml
+    set:
+      gateway.hpa.targetTokensPerSecond: 6M
+    asserts:
+      - lengthEqual:
+          path: spec.metrics
+          count: 3
+      - equal:
+          path: spec.metrics[2]
+          value:
+            type: Pods
+            pods:
+              metric:
+                name: litellm_tokens_per_second
+              target:
+                type: AverageValue
+                averageValue: "6M"
+      - notContains:
+          path: spec.metrics
+          content:
+            type: Pods
+            pods:
+              metric:
+                name: litellm_requests_per_second
+          any: true
+
+  - it: renders requests and tokens targets together and keeps CPU and memory
+    template: gateway/hpa.yaml
+    set:
+      gateway.hpa.targetRequestsPerSecond: 90
+      gateway.hpa.targetTokensPerSecond: 6000000
+    asserts:
+      - lengthEqual:
+          path: spec.metrics
+          count: 4
+      - equal:
+          path: spec.metrics[0].resource.name
+          value: cpu
+      - equal:
+          path: spec.metrics[1].resource.name
+          value: memory
+      - equal:
+          path: spec.metrics[2].pods.metric.name
+          value: litellm_requests_per_second
+      - equal:
+          path: spec.metrics[3].pods.metric.name
+          value: litellm_tokens_per_second
+      - equal:
+          path: spec.metrics[3].pods.target.averageValue
+          value: "6000000"
+
+  - it: scales on workload metrics alone when the resource targets are cleared
+    template: gateway/hpa.yaml
+    set:
+      gateway.hpa.targetCPUUtilizationPercentage: null
+      gateway.hpa.targetMemoryUtilizationPercentage: null
+      gateway.hpa.targetRequestsPerSecond: 90
+      gateway.hpa.targetTokensPerSecond: 6000000
+    asserts:
+      - lengthEqual:
+          path: spec.metrics
+          count: 2
+      - notContains:
+          path: spec.metrics
+          content:
+            type: Resource
+          any: true
+      - equal:
+          path: spec.metrics[0].pods.metric.name
+          value: litellm_requests_per_second
+      - equal:
+          path: spec.metrics[1].pods.metric.name
+          value: litellm_tokens_per_second
+      - notMatchRegexRaw:
+          pattern: per_minute
+
+  - it: ignores the per-minute keys, which the chart never shipped
+    template: gateway/hpa.yaml
+    set:
+      gateway.hpa.targetRequestsPerMinute: 5400
+      gateway.hpa.targetTokensPerMinute: 360000000
+    asserts:
+      - lengthEqual:
+          path: spec.metrics
+          count: 2
+      - notContains:
+          path: spec.metrics
+          content:
+            type: Pods
+          any: true
+
+  - it: renders no ServiceMonitor by default
+    template: gateway/servicemonitor.yaml
+    asserts:
+      - hasDocuments:
+          count: 0
+
+  - it: refuses a ServiceMonitor without the metrics server, whose http port needs a bearer token
+    template: gateway/servicemonitor.yaml
+    set:
+      gateway.serviceMonitor.enabled: true
+    asserts:
+      - failedTemplate:
+          errorPattern: gateway.serviceMonitor.enabled requires gateway.metricsServer.enabled
+
+  - it: scrapes each gateway pod through the metrics port
+    template: gateway/servicemonitor.yaml
+    release:
+      name: rel
+      namespace: llm
+    set:
+      gateway.serviceMonitor.enabled: true
+      gateway.metricsServer.enabled: true
+      gateway.serviceMonitor.labels:
+        release: kube-prometheus-stack
+    asserts:
+      - isKind:
+          of: ServiceMonitor
+      - equal:
+          path: metadata.labels.release
+          value: kube-prometheus-stack
+      - equal:
+          path: spec.selector.matchLabels
+          value:
+            app.kubernetes.io/name: litellm
+            app.kubernetes.io/instance: rel
+            app.kubernetes.io/component: gateway
+      - equal:
+          path: spec.namespaceSelector.matchNames
+          value:
+            - llm
+      - equal:
+          path: spec.endpoints
+          value:
+            - port: metrics
+              path: /metrics/
+              interval: 15s
+              scrapeTimeout: 10s
+              scheme: http
+
+  - it: honours a custom scrape interval
+    template: gateway/servicemonitor.yaml
+    set:
+      gateway.serviceMonitor.enabled: true
+      gateway.serviceMonitor.interval: 30s
+      gateway.metricsServer.enabled: true
+    asserts:
+      - equal:
+          path: spec.endpoints[0].interval
+          value: 30s
diff --git a/helm/litellm/values.yaml b/helm/litellm/values.yaml
index b5d535c992d..1873219d1ea 100644
--- a/helm/litellm/values.yaml
+++ b/helm/litellm/values.yaml
@@ -225,6 +225,26 @@ database:
       usernameKey: username
       passwordKey: password
 
+  # In-container connection pool (PgBouncer, transaction mode) shared by every
+  # gateway worker in the pod. Without it each of the `gateway.numWorkers`
+  # workers opens its own Prisma pool straight to Postgres, so a pod's
+  # footprint against the database's connection ceiling is
+  # numWorkers x connection_limit and grows with every replica. With it, the
+  # pod holds at most maxDbConnections upstream connections no matter how many
+  # workers run; the workers connect to the pool over loopback, with no extra
+  # network hop. The chart emits LITELLM_PGBOUNCER_ENABLED /
+  # LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS / LITELLM_PGBOUNCER_MAX_CLIENT_CONN on
+  # the gateway container and its collector sidecar only: the backend runs a
+  # single worker and the migrations Job must keep a direct connection. With
+  # `database.writer.useIAMAuth` or `useAzureEntraAuth` the pool mints and
+  # renews the database token itself, so the workers never see it. Starting profile for
+  # `gateway.numWorkers: 4` is maxDbConnections: 20, so a database with a
+  # 5000-connection ceiling fits roughly 200 gateway replicas.
+  connectionPool:
+    enabled: false
+    maxDbConnections: 20
+    maxClientConn: 1000
+
 # Optional Redis. Leave host empty to disable.
 #
 # This is the proxy's coordination store: cross-pod tpm/rpm rate limits, spend
@@ -284,6 +304,52 @@ gateway:
         memory: 128Mi
       limits:
         memory: 512Mi
+  # Prometheus Operator ServiceMonitor for the gateway pods. Scrapes the
+  # `<gateway>-metrics` Service, so it requires metricsServer above (the http
+  # port serves /metrics/ behind virtual-key auth). Every pod is its own scrape
+  # target, so the samples carry the `pod` label the per-pod autoscaling
+  # queries below group by.
+  serviceMonitor:
+    enabled: false
+    labels: {}
+    interval: 15s
+    scrapeTimeout: 10s
+  # Opt-in `collector` sidecar (same image, `python -m litellm.proxy.collector`)
+  # that runs the post-response spend pipeline (cost calculation, spend logs,
+  # spend counters, budget reservation reconciliation) so the uvicorn workers
+  # only serialise a compact event over loopback and go back to serving
+  # requests. It shares the pod's env, proxy config, in-container pgbouncer and
+  # Redis spend buffer, so the per-pod DB connection budget is unchanged.
+  # Delivery is at-most-once inside the pod: events already handed over are
+  # lost if the sidecar dies before writing them; events the workers cannot
+  # hand over follow `onUnavailable`.
+  collector:
+    enabled: false
+    # unix:///<dir>/<file>.sock (the <dir> becomes a shared emptyDir) or
+    # tcp://127.0.0.1:<port>
+    address: unix:///var/run/litellm/collector.sock
+    # Events each uvicorn worker holds in memory while the sidecar is slow or
+    # restarting.
+    bufferSize: 1000
+    # fallback: run the pipeline in the worker when the sidecar is unreachable
+    # or the buffer is full (spend stays exact, that request costs gateway CPU
+    # again). drop: count and discard the event instead (spend under-reports).
+    onUnavailable: fallback
+    # How long the workers keep pushing buffered events on shutdown, and how
+    # long the sidecar keeps serving open connections after SIGTERM.
+    drainTimeoutSeconds: 10
+    # Sized independently of the gateway container; the pipeline is CPU bound.
+    resources:
+      requests:
+        cpu: 500m
+        memory: 1Gi
+      limits:
+        cpu: "1"
+        memory: 2Gi
+    # With hpa.targetCPUUtilizationPercentage set, scale on an autoscaling/v2
+    # ContainerResource metric of the `gateway` container only, so the
+    # sidecar's CPU never drives inference replicas. Needs Kubernetes 1.30+.
+    scaleOnGatewayContainerCpu: true
   image:
     repository: ghcr.io/berriai/litellm-gateway
     tag: ""              # defaults to .Chart.AppVersion
@@ -340,6 +406,25 @@ gateway:
     #     policies:
     #       - { type: Percent, value: 100, periodSeconds: 30 }
     behavior: {}
+    # Opt-in per-pod workload targets, rendered as autoscaling/v2 `Pods` metrics
+    # named `litellm_requests_per_second` and `litellm_tokens_per_second` with an
+    # AverageValue target. They coexist with the CPU/memory targets above: the
+    # HPA scales on whichever metric asks for the most replicas. Kubernetes has
+    # no idea what a token is, so a Prometheus Adapter must serve those two
+    # names on custom.metrics.k8s.io from the proxy's counters, grouped by the
+    # scrape target's `pod` label (enable serviceMonitor above):
+    #   litellm_requests_per_second:
+    #     sum(rate(litellm_proxy_total_requests_metric_total{<<.LabelMatchers>>}[1m])) by (<<.GroupBy>>)
+    #   litellm_tokens_per_second:
+    #     sum(rate(litellm_total_tokens_metric_total{<<.LabelMatchers>>}[1m])) by (<<.GroupBy>>)
+    # rate() over [1m] is already per second, so no `* 60`. How fast the HPA
+    # reacts is set by that window, the scrape interval and the HPA sync period
+    # (15s by default), not by the unit: keep serviceMonitor.interval at 15s or
+    # faster so a 1m window holds at least 4 samples. averageValue takes SI
+    # suffixes, so "6M" is six million tokens per second per pod. Tokens are
+    # counted when a response completes, so TPS trails long streams.
+    targetRequestsPerSecond: ""
+    targetTokensPerSecond: ""
   # PodDisruptionBudget for the gateway pods. Set exactly one of
   # `minAvailable` / `maxUnavailable` (minAvailable wins if both are set;
   # enabling without either falls back to `maxUnavailable: 1`). Disabled by
diff --git a/litellm-proxy-extras/litellm_proxy_extras/migrations/20260717000000_cascade_delete_jwt_key_mapping_on_token_delete/migration.sql b/litellm-proxy-extras/litellm_proxy_extras/migrations/20260717000000_cascade_delete_jwt_key_mapping_on_token_delete/migration.sql
new file mode 100644
index 00000000000..e5d48abcb52
--- /dev/null
+++ b/litellm-proxy-extras/litellm_proxy_extras/migrations/20260717000000_cascade_delete_jwt_key_mapping_on_token_delete/migration.sql
@@ -0,0 +1,15 @@
+-- DropForeignKey
+DO $$
+BEGIN
+    IF EXISTS (SELECT 1 FROM pg_constraint WHERE conname = 'LiteLLM_JWTKeyMapping_token_fkey') THEN
+        ALTER TABLE "LiteLLM_JWTKeyMapping" DROP CONSTRAINT "LiteLLM_JWTKeyMapping_token_fkey";
+    END IF;
+END $$;
+
+-- AddForeignKey
+DO $$
+BEGIN
+    IF NOT EXISTS (SELECT 1 FROM pg_constraint WHERE conname = 'LiteLLM_JWTKeyMapping_token_fkey') THEN
+        ALTER TABLE "LiteLLM_JWTKeyMapping" ADD CONSTRAINT "LiteLLM_JWTKeyMapping_token_fkey" FOREIGN KEY ("token") REFERENCES "LiteLLM_VerificationToken"("token") ON DELETE CASCADE ON UPDATE CASCADE;
+    END IF;
+END $$;
diff --git a/litellm-proxy-extras/litellm_proxy_extras/migrations/20260910000000_skills_on_object_permission/migration.sql b/litellm-proxy-extras/litellm_proxy_extras/migrations/20260910000000_skills_on_object_permission/migration.sql
new file mode 100644
index 00000000000..c982bc38a69
--- /dev/null
+++ b/litellm-proxy-extras/litellm_proxy_extras/migrations/20260910000000_skills_on_object_permission/migration.sql
@@ -0,0 +1 @@
+ALTER TABLE "LiteLLM_ObjectPermissionTable" ADD COLUMN IF NOT EXISTS "skills" TEXT[] DEFAULT ARRAY[]::TEXT[];
diff --git a/litellm-proxy-extras/litellm_proxy_extras/schema.prisma b/litellm-proxy-extras/litellm_proxy_extras/schema.prisma
index 3d254cd2ea2..817df082d8c 100644
--- a/litellm-proxy-extras/litellm_proxy_extras/schema.prisma
+++ b/litellm-proxy-extras/litellm_proxy_extras/schema.prisma
@@ -282,6 +282,7 @@ model LiteLLM_ObjectPermissionTable {
   mcp_toolsets          String[]       @default([]) // Toolset IDs granted to this key/team/user
   search_tools          String[]       @default([]) // search_tool_name values this key/team/user may call
   mcp_tool_search_enabled Boolean?
+  skills                String[]       @default([]) // Claude Code plugin names granted to this key/team beyond the public (enabled) set
   teams                 LiteLLM_TeamTable[]
   projects              LiteLLM_ProjectTable[]
   verification_tokens   LiteLLM_VerificationToken[]
@@ -492,7 +493,7 @@ model LiteLLM_JWTKeyMapping {
     updated_at        DateTime @default(now()) @updatedAt
     updated_by        String?
 
-    litellm_verification_token LiteLLM_VerificationToken @relation(fields: [token], references: [token])
+    litellm_verification_token LiteLLM_VerificationToken @relation(fields: [token], references: [token], onDelete: Cascade)
 
     @@unique([jwt_claim_name, jwt_claim_value])
     @@index([jwt_claim_name, jwt_claim_value, is_active])
diff --git a/litellm-proxy-extras/pyproject.toml b/litellm-proxy-extras/pyproject.toml
index 91b4e4a7ba1..7d4c78088f1 100644
--- a/litellm-proxy-extras/pyproject.toml
+++ b/litellm-proxy-extras/pyproject.toml
@@ -1,6 +1,6 @@
 [project]
 name = "litellm-proxy-extras"
-version = "0.4.95"
+version = "0.4.96"
 description = "Additional files for the LiteLLM Proxy. Reduces the size of the main litellm package."
 readme = "README.md"
 requires-python = ">=3.9"
@@ -26,7 +26,7 @@ required-version = ">=0.10.9"
 module-root = ""
 
 [tool.commitizen]
-version = "0.4.95"
+version = "0.4.96"
 version_files = [
     "pyproject.toml:^version",
     "../pyproject.toml:litellm-proxy-extras==",
diff --git a/litellm-rust/AGENTS.md b/litellm-rust/AGENTS.md
index b8d1f2db4d7..17856218e60 100644
--- a/litellm-rust/AGENTS.md
+++ b/litellm-rust/AGENTS.md
@@ -1,18 +1,19 @@
 # AGENTS.md
 
-litellm-rust has five crates. A crate is a layer or shared foundation, not a route. Routes (ocr, realtime, chat) and providers (mistral, openai) are modules inside the layers.
+litellm-rust has six crates. A crate is a layer or shared foundation, not a route. Routes (ocr, realtime, chat) and providers (mistral, openai) are modules inside the layers.
 
 ## Crates
 
 | Crate | Role |
 |-------|------|
 | litellm-core | The LiteLLM SDK in Rust. One public entrypoint per top-level call (`messages::messages()`), owning types, transforms, provider resolution, auth, and the provider HTTP call. Call it, get a typed response. |
+| litellm-token-counter | Standalone input token counting shared by host integrations without pulling in the full SDK. |
 | litellm-config | Config-loading boundary. Returns resolved core deployment data and optionally delegates loading to Python. |
 | litellm-ai-gateway | The axum server (behind the `server` feature) plus the WebSocket hosts. Translates HTTP/WS to core entrypoints; owns no provider logic and no handlers. |
 | litellm-python-interop | Domain-neutral PyO3 foundation for GIL handling and typed Python/Serde conversion. |
 | litellm-python-bridge | PyO3 cdylib exposing LiteLLM Rust APIs to the Python SDK. Owns API registration, domain wiring, and Python exception mapping. |
 
-Dependency direction is acyclic: `litellm-config` depends on `litellm-core`, the gateway depends on both, and `litellm-python-bridge` depends on the domain layers and `litellm-python-interop`. The interop foundation depends on no LiteLLM domain crate.
+Dependency direction is acyclic: `litellm-config` depends on `litellm-core`, the gateway depends on both, and `litellm-python-bridge` depends on the domain layers, `litellm-token-counter`, and `litellm-python-interop`. The token counter and interop foundations depend on no LiteLLM domain crate.
 
 ## Where a route lives
 
diff --git a/litellm-rust/Cargo.lock b/litellm-rust/Cargo.lock
index 43b9ec1aac2..0e8e6e09a21 100644
--- a/litellm-rust/Cargo.lock
+++ b/litellm-rust/Cargo.lock
@@ -2,6 +2,20 @@
 # It is not intended for manual editing.
 version = 4
 
+[[package]]
+name = "ahash"
+version = "0.8.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5a15f179cd60c4584b8a8c596927aadc462e27f2ca70c04e0071964a73ba7a75"
+dependencies = [
+ "cfg-if",
+ "getrandom 0.3.4",
+ "once_cell",
+ "serde",
+ "version_check",
+ "zerocopy",
+]
+
 [[package]]
 name = "aho-corasick"
 version = "1.1.5"
@@ -418,7 +432,7 @@ checksum = "edca88bc138befd0323b20752846e6587272d3b03b0343c8ea28a6f819e6e71f"
 dependencies = [
  "async-trait",
  "axum-core",
- "base64",
+ "base64 0.22.1",
  "bytes",
  "futures-util",
  "http 1.4.2",
@@ -468,6 +482,12 @@ dependencies = [
  "tracing",
 ]
 
+[[package]]
+name = "base64"
+version = "0.13.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9e1b586273c5702936fe7b7d6896644d8be71e6314cfe09d3167c95f712589e8"
+
 [[package]]
 name = "base64"
 version = "0.22.1"
@@ -542,6 +562,15 @@ version = "0.3.0"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "37b2a672a2cb129a2e41c10b1224bb368f9f37a2b16b612598138befd7b37eb5"
 
+[[package]]
+name = "castaway"
+version = "0.2.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "dec551ab6e7578819132c713a93c022a05d60159dc86e7a7050223577484c55a"
+dependencies = [
+ "rustversion",
+]
+
 [[package]]
 name = "cc"
 version = "1.3.0"
@@ -644,6 +673,21 @@ version = "0.5.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "0c9ea0ac24bc397ab3c98583a3c9ba74fa56b09a4449bbe172b9b1ddb016027a"
 
+[[package]]
+name = "compact_str"
+version = "0.9.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "9dfdd1c2274d9aa354115b09dc9a901d6c5576818cdf70d14cae2bdb47df00ab"
+dependencies = [
+ "castaway",
+ "cfg-if",
+ "itoa",
+ "rustversion",
+ "ryu",
+ "serde",
+ "static_assertions",
+]
+
 [[package]]
 name = "const-oid"
 version = "0.10.2"
@@ -696,7 +740,7 @@ dependencies = [
  "ciborium",
  "clap",
  "criterion-plot",
- "itertools",
+ "itertools 0.13.0",
  "num-traits",
  "oorandom",
  "page_size",
@@ -716,7 +760,7 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "d8d80a2f4f5b554395e47b5d8305bc3d27813bacb73493eb1001e8f76dae29ea"
 dependencies = [
  "cast",
- "itertools",
+ "itertools 0.13.0",
 ]
 
 [[package]]
@@ -778,6 +822,56 @@ dependencies = [
  "cmov",
 ]
 
+[[package]]
+name = "daachorse"
+version = "3.0.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5614204febbc33cc07a2806aa6440b904ac012b68eecc37f4493ea4a76455a3d"
+
+[[package]]
+name = "darling"
+version = "0.20.11"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fc7f46116c46ff9ab3eb1597a45688b6715c6e628b5c133e288e709a29bcb4ee"
+dependencies = [
+ "darling_core",
+ "darling_macro",
+]
+
+[[package]]
+name = "darling_core"
+version = "0.20.11"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0d00b9596d185e565c2207a0b01f8bd1a135483d02d9b7b0a54b11da8d53412e"
+dependencies = [
+ "fnv",
+ "ident_case",
+ "proc-macro2",
+ "quote",
+ "strsim",
+ "syn 2.0.119",
+]
+
+[[package]]
+name = "darling_macro"
+version = "0.20.11"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fc34b93ccb385b40dc71c6fceac4b2ad23662c7eeb248cf10d529b7e055b6ead"
+dependencies = [
+ "darling_core",
+ "quote",
+ "syn 2.0.119",
+]
+
+[[package]]
+name = "dary_heap"
+version = "0.3.9"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "8b1e3a325bc115f096c8b77bbf027a7c2592230e70be2d985be950d3d5e60ebe"
+dependencies = [
+ "serde",
+]
+
 [[package]]
 name = "data-encoding"
 version = "2.11.0"
@@ -790,6 +884,37 @@ version = "0.5.8"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "7cd812cc2bc1d69d4764bd80df88b4317eaef9e773c75226407d9bc0876b211c"
 
+[[package]]
+name = "derive_builder"
+version = "0.20.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "507dfb09ea8b7fa618fcf76e953f4f5e192547945816d5358edffe39f6f94947"
+dependencies = [
+ "derive_builder_macro",
+]
+
+[[package]]
+name = "derive_builder_core"
+version = "0.20.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2d5bcf7b024d6835cfb3d473887cd966994907effbe9227e8c8219824d06c4e8"
+dependencies = [
+ "darling",
+ "proc-macro2",
+ "quote",
+ "syn 2.0.119",
+]
+
+[[package]]
+name = "derive_builder_macro"
+version = "0.20.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "ab63b0e2bf4d5928aff72e83a7dace85d7bba5fe12dcc3c5a572d78caffd3f3c"
+dependencies = [
+ "derive_builder_core",
+ "syn 2.0.119",
+]
+
 [[package]]
 name = "digest"
 version = "0.10.7"
@@ -841,6 +966,12 @@ version = "1.0.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "877a4ace8713b0bcf2a4e7eec82529c029f1d0619886d18145fea96c3ffe5c0f"
 
+[[package]]
+name = "esaxx-rs"
+version = "0.1.10"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d817e038c30374a4bcb22f94d0a8a0e216958d4c3dcde369b1439fec4bdda6e6"
+
 [[package]]
 name = "fastrand"
 version = "2.5.0"
@@ -964,6 +1095,18 @@ dependencies = [
  "wasm-bindgen",
 ]
 
+[[package]]
+name = "getrandom"
+version = "0.3.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "899def5c37c4fd7b2664648c28120ecec138e4d395b459e5ca34f9cce2dd77fd"
+dependencies = [
+ "cfg-if",
+ "libc",
+ "r-efi 5.3.0",
+ "wasip2",
+]
+
 [[package]]
 name = "getrandom"
 version = "0.4.3"
@@ -973,7 +1116,7 @@ dependencies = [
  "cfg-if",
  "js-sys",
  "libc",
- "r-efi",
+ "r-efi 6.0.0",
  "rand_core 0.10.1",
  "wasm-bindgen",
 ]
@@ -1220,7 +1363,7 @@ version = "0.1.20"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "96547c2556ec9d12fb1578c4eaf448b04993e7fb79cbaad930a656880a6bdfa0"
 dependencies = [
- "base64",
+ "base64 0.22.1",
  "bytes",
  "futures-channel",
  "futures-util",
@@ -1319,6 +1462,12 @@ dependencies = [
  "zerovec",
 ]
 
+[[package]]
+name = "ident_case"
+version = "1.0.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b9e0384b61958566e926dc50660321d12159025e767c18e043daf26b70104c39"
+
 [[package]]
 name = "idna"
 version = "1.1.0"
@@ -1348,6 +1497,8 @@ checksum = "d466e9454f08e4a911e14806c24e16fba1b4c121d1ea474396f396069cf949d9"
 dependencies = [
  "equivalent",
  "hashbrown",
+ "serde",
+ "serde_core",
 ]
 
 [[package]]
@@ -1365,6 +1516,15 @@ dependencies = [
  "either",
 ]
 
+[[package]]
+name = "itertools"
+version = "0.14.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2b192c782037fadd9cfa75548310488aabdbf3d2da73885b31bd0abd03351285"
+dependencies = [
+ "either",
+]
+
 [[package]]
 name = "itoa"
 version = "1.0.18"
@@ -1409,7 +1569,7 @@ name = "litellm-ai-gateway"
 version = "0.1.0"
 dependencies = [
  "axum",
- "base64",
+ "base64 0.22.1",
  "futures-channel",
  "futures-util",
  "litellm-config",
@@ -1447,17 +1607,19 @@ dependencies = [
  "aws-sigv4",
  "aws-smithy-runtime-api",
  "aws-types",
- "base64",
+ "base64 0.22.1",
  "rand 0.8.7",
  "reqwest",
  "rstest",
  "serde",
  "serde_json",
+ "serde_path_to_error",
  "sha2 0.10.9",
  "thiserror 2.0.19",
  "tokio",
  "tracing",
  "tracing-subscriber",
+ "url",
 ]
 
 [[package]]
@@ -1469,6 +1631,7 @@ dependencies = [
  "litellm-ai-gateway",
  "litellm-core",
  "litellm-python-interop",
+ "litellm-token-counter",
  "pyo3",
  "pyo3-async-runtimes",
  "serde",
@@ -1489,6 +1652,22 @@ dependencies = [
  "serde_json",
 ]
 
+[[package]]
+name = "litellm-token-counter"
+version = "0.1.0"
+dependencies = [
+ "criterion",
+ "indexmap",
+ "itoa",
+ "rand 0.8.7",
+ "rstest",
+ "serde",
+ "serde_json",
+ "thiserror 2.0.19",
+ "tokenizers",
+ "unicode-normalization-alignments",
+]
+
 [[package]]
 name = "litemap"
 version = "0.8.2"
@@ -1507,6 +1686,22 @@ version = "0.1.2"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "112b39cec0b298b6c1999fee3e31427f74f676e4cb9879ed1a121b43661a4154"
 
+[[package]]
+name = "macro_rules_attribute"
+version = "0.2.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b3ae8f6d608c795738406608304d30a2dfbdc8e58e44f7ba43236da5208ded3c"
+dependencies = [
+ "macro_rules_attribute-proc_macro",
+ "pastey",
+]
+
+[[package]]
+name = "macro_rules_attribute-proc_macro"
+version = "0.2.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "fc04a4c58212d57930a24bf47d3fa87485264a3a054e9c10e042eb373573ad3c"
+
 [[package]]
 name = "matchit"
 version = "0.7.3"
@@ -1535,6 +1730,12 @@ dependencies = [
  "unicase",
 ]
 
+[[package]]
+name = "minimal-lexical"
+version = "0.2.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "68354c5c6bd36d73ff3feceb05efa59b6acb7626617f4962be322a825e61f79a"
+
 [[package]]
 name = "mio"
 version = "1.2.2"
@@ -1546,6 +1747,38 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "monostate"
+version = "0.1.18"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "3341a273f6c9d5bef1908f17b7267bbab0e95c9bf69a0d4dcf8e9e1b2c76ef67"
+dependencies = [
+ "monostate-impl",
+ "serde",
+ "serde_core",
+]
+
+[[package]]
+name = "monostate-impl"
+version = "0.1.18"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "e4db6d5580af57bf992f59068d4ea26fd518574ff48d7639b255a36f9de6e7e9"
+dependencies = [
+ "proc-macro2",
+ "quote",
+ "syn 2.0.119",
+]
+
+[[package]]
+name = "nom"
+version = "7.1.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d273983c5a657a70a3e8f2a01329822f3b8c8172b73826411a55751e404a0a4a"
+dependencies = [
+ "memchr",
+ "minimal-lexical",
+]
+
 [[package]]
 name = "num-conv"
 version = "0.2.2"
@@ -1576,6 +1809,28 @@ version = "1.21.4"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "9f7c3e4beb33f85d45ae3e3a1792185706c8e16d043238c593331cc7cd313b50"
 
+[[package]]
+name = "onig"
+version = "6.5.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "0cc3cbf698f9438986c11a880c90a6d04b9de27575afd28bbf45b154b6c709e2"
+dependencies = [
+ "bitflags",
+ "libc",
+ "once_cell",
+ "onig_sys",
+]
+
+[[package]]
+name = "onig_sys"
+version = "69.9.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1e68317604e77e53b85896388e1a803c1d21b74c899ec9e5e1112db90735edd7"
+dependencies = [
+ "cc",
+ "pkg-config",
+]
+
 [[package]]
 name = "oorandom"
 version = "11.1.5"
@@ -1604,6 +1859,18 @@ dependencies = [
  "winapi",
 ]
 
+[[package]]
+name = "paste"
+version = "1.0.15"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "57c0d7b74b563b49d38dae00a0c37d4d6de9b432382b2892f0574ddcae73fd0a"
+
+[[package]]
+name = "pastey"
+version = "0.2.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2ee67f1008b1ba2321834326597b8e186293b049a023cdef258527550b9935b4"
+
 [[package]]
 name = "percent-encoding"
 version = "2.3.2"
@@ -1850,6 +2117,12 @@ dependencies = [
  "proc-macro2",
 ]
 
+[[package]]
+name = "r-efi"
+version = "5.3.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "69cdb34c158ceb288df11e18b4bd39de994f6657d83847bdffdbd7f346754b0f"
+
 [[package]]
 name = "r-efi"
 version = "6.0.0"
@@ -1863,10 +2136,20 @@ source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "22f6172bdec972074665ed81ed53b71da00bfc44b65a753cfde883ec4c702a1a"
 dependencies = [
  "libc",
- "rand_chacha",
+ "rand_chacha 0.3.1",
  "rand_core 0.6.4",
 ]
 
+[[package]]
+name = "rand"
+version = "0.9.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b9ef1d0d795eb7d84685bca4f72f3649f064e6641543d3a8c415898726a57b41"
+dependencies = [
+ "rand_chacha 0.9.0",
+ "rand_core 0.9.5",
+]
+
 [[package]]
 name = "rand"
 version = "0.10.2"
@@ -1888,6 +2171,16 @@ dependencies = [
  "rand_core 0.6.4",
 ]
 
+[[package]]
+name = "rand_chacha"
+version = "0.9.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "d3022b5f1df60f26e1ffddd6c66e8aa15de382ae63b3a0c1bfc0e4d3e3f325cb"
+dependencies = [
+ "ppv-lite86",
+ "rand_core 0.9.5",
+]
+
 [[package]]
 name = "rand_core"
 version = "0.6.4"
@@ -1897,6 +2190,15 @@ dependencies = [
  "getrandom 0.2.17",
 ]
 
+[[package]]
+name = "rand_core"
+version = "0.9.5"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "76afc826de14238e6e8c374ddcc1fa19e374fd8dd986b0d2af0d02377261d83c"
+dependencies = [
+ "getrandom 0.3.4",
+]
+
 [[package]]
 name = "rand_core"
 version = "0.10.1"
@@ -1922,6 +2224,17 @@ dependencies = [
  "rayon-core",
 ]
 
+[[package]]
+name = "rayon-cond"
+version = "0.4.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "2964d0cf57a3e7a06e8183d14a8b527195c706b7983549cd5462d5aa3747438f"
+dependencies = [
+ "either",
+ "itertools 0.14.0",
+ "rayon",
+]
+
 [[package]]
 name = "rayon-core"
 version = "1.13.0"
@@ -1979,7 +2292,7 @@ version = "0.12.28"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "eddd3ca559203180a307f12d114c268abf583f59b03cb906fd0b3ff8646c1147"
 dependencies = [
- "base64",
+ "base64 0.22.1",
  "bytes",
  "futures-channel",
  "futures-core",
@@ -2361,12 +2674,36 @@ dependencies = [
  "windows-sys 0.61.2",
 ]
 
+[[package]]
+name = "spm_precompiled"
+version = "0.1.4"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "5851699c4033c63636f7ea4cf7b7c1f1bf06d0cc03cfb42e711de5a5c46cf326"
+dependencies = [
+ "base64 0.13.1",
+ "nom",
+ "serde",
+ "unicode-segmentation",
+]
+
 [[package]]
 name = "stable_deref_trait"
 version = "1.2.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "6ce2be8dc25455e1f91df71bfa12ad37d7af1092ae736f3a6cd0e37bc7810596"
 
+[[package]]
+name = "static_assertions"
+version = "1.1.0"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "a2eb9349b6444b326872e140eb1cf5e7c522154d69e7a0ffb0fb81c06b37543f"
+
+[[package]]
+name = "strsim"
+version = "0.11.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7da8b5736845d9f2fcb837ea5d9e2628564b3b043a70948a3f0b778838c5fb4f"
+
 [[package]]
 name = "subtle"
 version = "2.6.1"
@@ -2535,6 +2872,39 @@ version = "0.1.1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "1f3ccbac311fea05f86f61904b462b55fb3df8837a366dfc601a0161d0532f20"
 
+[[package]]
+name = "tokenizers"
+version = "0.23.2"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "7afbf6e88718afcc138bad01d6ccc3051dbbc3b2ce9793d8b8a3aeb610969cfc"
+dependencies = [
+ "ahash",
+ "compact_str",
+ "daachorse",
+ "dary_heap",
+ "derive_builder",
+ "esaxx-rs",
+ "getrandom 0.3.4",
+ "itertools 0.14.0",
+ "log",
+ "macro_rules_attribute",
+ "monostate",
+ "onig",
+ "paste",
+ "rand 0.9.5",
+ "rayon",
+ "rayon-cond",
+ "regex",
+ "regex-syntax",
+ "serde",
+ "serde_json",
+ "spm_precompiled",
+ "thiserror 2.0.19",
+ "unicode-normalization-alignments",
+ "unicode-segmentation",
+ "unicode_categories",
+]
+
 [[package]]
 name = "tokio"
 version = "1.53.0"
@@ -2773,6 +3143,27 @@ version = "1.0.24"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "e6e4313cd5fcd3dad5cafa179702e2b244f760991f45397d14d4ebf38247da75"
 
+[[package]]
+name = "unicode-normalization-alignments"
+version = "0.1.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "43f613e4fa046e69818dd287fdc4bc78175ff20331479dab6e1b0f98d57062de"
+dependencies = [
+ "smallvec",
+]
+
+[[package]]
+name = "unicode-segmentation"
+version = "1.13.3"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "c6f5d3c3b1bf09027a88a6bc961fc00497d651009560b5463668dc81b0fa87a8"
+
+[[package]]
+name = "unicode_categories"
+version = "0.1.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "39ec24b3121d976906ece63c9daad25b85969647682eee313cb5779fdd69e14e"
+
 [[package]]
 name = "untrusted"
 version = "0.9.0"
@@ -2856,6 +3247,15 @@ version = "0.11.1+wasi-snapshot-preview1"
 source = "registry+https://github.com/rust-lang/crates.io-index"
 checksum = "ccf3ec651a847eb01de73ccad15eb7d99f80485de043efb2f370cd654f4ea44b"
 
+[[package]]
+name = "wasip2"
+version = "1.0.4+wasi-0.2.12"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "b67efb37e106e55ce722a510d6b5f9c17f083e5fc79afc2badeb12cc313d9487"
+dependencies = [
+ "wit-bindgen",
+]
+
 [[package]]
 name = "wasm-bindgen"
 version = "0.2.126"
@@ -3081,6 +3481,12 @@ dependencies = [
  "memchr",
 ]
 
+[[package]]
+name = "wit-bindgen"
+version = "0.57.1"
+source = "registry+https://github.com/rust-lang/crates.io-index"
+checksum = "1ebf944e87a7c253233ad6766e082e3cd714b5d03812acc24c318f549614536e"
+
 [[package]]
 name = "writeable"
 version = "0.6.3"
diff --git a/litellm-rust/Cargo.toml b/litellm-rust/Cargo.toml
index 82de7f40069..f3e54e5b2aa 100644
--- a/litellm-rust/Cargo.toml
+++ b/litellm-rust/Cargo.toml
@@ -1,6 +1,7 @@
 [workspace]
 members = [
     "crates/core",
+    "crates/token-counter",
     "crates/config",
     "crates/ai-gateway",
     "crates/python-interop",
@@ -18,6 +19,7 @@ repository = "https://github.com/BerriAI/litellm"
 tracing = "0.1"
 tracing-subscriber = { version = "0.3", default-features = false, features = ["registry", "std"] }
 litellm-core = { path = "crates/core" }
+litellm-token-counter = { path = "crates/token-counter" }
 litellm-config = { path = "crates/config" }
 litellm-ai-gateway = { path = "crates/ai-gateway", default-features = false }
 litellm-python-interop = { path = "crates/python-interop" }
@@ -39,6 +41,8 @@ tokio = { version = "1", features = ["rt-multi-thread", "macros", "time", "net"]
 tokio-tungstenite = { version = "0.24", default-features = false, features = ["connect", "rustls-tls-native-roots"] }
 futures-util = { version = "0.3", default-features = false, features = ["sink", "std"] }
 base64 = "0.22"
+url = "2.5.8"
+criterion = "0.8.2"
 
 [profile.release]
 opt-level = 3
diff --git a/litellm-rust/crates/ai-gateway/README.md b/litellm-rust/crates/ai-gateway/README.md
index 9fef59a277d..cbcd8119546 100644
--- a/litellm-rust/crates/ai-gateway/README.md
+++ b/litellm-rust/crates/ai-gateway/README.md
@@ -6,17 +6,18 @@ dials OpenAI upstream, and splices the two sockets frame-by-frame.
 
 ## Crates
 
-`litellm-rust` has five crates. A crate is a layer or shared foundation, not a route:
+`litellm-rust` has six crates. A crate is a layer or shared foundation, not a route:
 
 | Crate | Role |
 |-------|------|
 | litellm-core | The LiteLLM SDK in Rust — per-route entrypoints (`messages::messages()`) that resolve the provider, transform, and make the call; plus types, provider transforms, and the router. |
+| litellm-token-counter | Standalone input token counting shared by host integrations without pulling in the full SDK. |
 | litellm-config | Config-loading boundary. Returns resolved deployments and optionally delegates loading to Python. |
 | litellm-ai-gateway | The Axum server (behind the `server` feature) and WebSocket hosts. Translates HTTP/WS to core entrypoints; no provider handlers. |
 | litellm-python-interop | Domain-neutral PyO3 foundation for GIL handling and typed Python/Serde conversion. |
 | litellm-python-bridge | PyO3 cdylib exposing LiteLLM Rust APIs to the Python SDK. |
 
-Dependency direction is acyclic: config depends on core, the gateway depends on config and core, and the Python bridge depends on the domain layers and Python interop.
+Dependency direction is acyclic: config depends on core, the gateway depends on config and core, and the Python bridge depends on the domain layers, token counter, and Python interop.
 
 - **Client endpoint:** `wss://<host>/v1/realtime?model=<model>` (WebSocket)
 - **Auth:** `Authorization: Bearer $LITELLM_MASTER_KEY` (fails closed if unset)
diff --git a/litellm-rust/crates/ai-gateway/src/audio_transcription/hooks.rs b/litellm-rust/crates/ai-gateway/src/audio_transcription/hooks.rs
index dbe2d3a325b..098ce071efc 100644
--- a/litellm-rust/crates/ai-gateway/src/audio_transcription/hooks.rs
+++ b/litellm-rust/crates/ai-gateway/src/audio_transcription/hooks.rs
@@ -269,7 +269,7 @@ fn guardrail_error_to_core_error(error: GuardrailError) -> Error {
 
 fn core_error_kind(error: &Error) -> &'static str {
     match error {
-        Error::Auth(_) => "AuthError",
+        Error::Auth(_) | Error::MissingApiKey { .. } => "AuthError",
         Error::InvalidProvider(_) => "InvalidProvider",
         Error::InvalidRequest(_) => "InvalidRequest",
         Error::InvalidType { .. } => "InvalidType",
diff --git a/litellm-rust/crates/ai-gateway/src/ocr/hooks.rs b/litellm-rust/crates/ai-gateway/src/ocr/hooks.rs
index ed41f1ff9e7..d1dd811f7ab 100644
--- a/litellm-rust/crates/ai-gateway/src/ocr/hooks.rs
+++ b/litellm-rust/crates/ai-gateway/src/ocr/hooks.rs
@@ -386,7 +386,7 @@ fn guardrail_error_to_core_error(error: GuardrailError) -> Error {
 
 fn core_error_kind(error: &Error) -> &'static str {
     match error {
-        Error::Auth(_) => "AuthError",
+        Error::Auth(_) | Error::MissingApiKey { .. } => "AuthError",
         Error::InvalidProvider(_) => "InvalidProvider",
         Error::InvalidRequest(_) => "InvalidRequest",
         Error::InvalidType { .. } => "InvalidType",
diff --git a/litellm-rust/crates/ai-gateway/src/routes/messages/mod.rs b/litellm-rust/crates/ai-gateway/src/routes/messages/mod.rs
index bb9f3851a77..c22d05f5726 100644
--- a/litellm-rust/crates/ai-gateway/src/routes/messages/mod.rs
+++ b/litellm-rust/crates/ai-gateway/src/routes/messages/mod.rs
@@ -114,7 +114,8 @@ impl IntoResponse for MessagesRouteError {
             | Error::Connect(_)
             | Error::InvalidResponse(_)
             | Error::InvalidType { .. }
-            | Error::MissingField(_) => (
+            | Error::MissingField(_)
+            | Error::MissingApiKey { .. } => (
                 StatusCode::BAD_GATEWAY,
                 "messages provider request failed".to_string(),
             ),
diff --git a/litellm-rust/crates/ai-gateway/src/trace_parity.rs b/litellm-rust/crates/ai-gateway/src/trace_parity.rs
index 614852c541d..21123df3f1c 100644
--- a/litellm-rust/crates/ai-gateway/src/trace_parity.rs
+++ b/litellm-rust/crates/ai-gateway/src/trace_parity.rs
@@ -47,10 +47,10 @@ pub async fn messages_request(
         .header(CONTENT_TYPE, "application/json")
         .body(Body::from(body.to_string()))
         .map_err(|error| Error::InvalidRequest(error.to_string()))?;
-    let response = routes::app(state)
-        .oneshot(request)
-        .await
-        .map_err(|error| match error {})?;
+    let response = match routes::app(state).oneshot(request).await {
+        Ok(response) => response,
+        Err(error) => match error {},
+    };
     let status: StatusCode = response.status();
     let bytes = to_bytes(response.into_body(), usize::MAX)
         .await
diff --git a/litellm-rust/crates/core/Cargo.toml b/litellm-rust/crates/core/Cargo.toml
index c0de7ff3977..b4ca88cf16f 100644
--- a/litellm-rust/crates/core/Cargo.toml
+++ b/litellm-rust/crates/core/Cargo.toml
@@ -4,6 +4,11 @@ version = "0.1.0"
 edition.workspace = true
 license.workspace = true
 repository.workspace = true
+autotests = false
+
+[[test]]
+name = "workspace_crate_allowlist"
+path = "tests/workspace_crate_allowlist.rs"
 
 [dependencies]
 base64.workspace = true
@@ -11,10 +16,13 @@ rand.workspace = true
 reqwest.workspace = true
 serde.workspace = true
 serde_json.workspace = true
+serde_path_to_error = "0.1"
+tokio.workspace = true
 thiserror.workspace = true
 tracing.workspace = true
 tracing-subscriber = { workspace = true, optional = true }
 sha2.workspace = true
+url.workspace = true
 aws-config = { version = "1.9.0", default-features = false, features = ["rustls", "rt-tokio"], optional = true }
 aws-credential-types = { version = "1.3.0", features = ["hardcoded-credentials"], optional = true }
 aws-sdk-sts = { version = "1.108.0", default-features = false, features = ["rustls", "rt-tokio"], optional = true }
diff --git a/litellm-rust/crates/core/src/constants.rs b/litellm-rust/crates/core/src/constants.rs
index fc81f4fa029..108d2a48e30 100644
--- a/litellm-rust/crates/core/src/constants.rs
+++ b/litellm-rust/crates/core/src/constants.rs
@@ -43,3 +43,6 @@ pub const EMPTY_TEXT_PLACEHOLDER: &str =
     "[System: Empty message content sanitised to satisfy protocol]";
 
 pub const FUNCTION_TRACE_TARGET: &str = "litellm::function_trace";
+pub(crate) const OCR_HTTP_TIMEOUT_SECS: u64 = 600;
+pub(crate) const OCR_CONNECT_TIMEOUT_SECS: u64 = 10;
+pub(crate) const MISTRAL_OCR_API_BASE: &str = "https://api.mistral.ai/v1";
diff --git a/litellm-rust/crates/core/src/error.rs b/litellm-rust/crates/core/src/error.rs
index db3fa2ec704..0382314057f 100644
--- a/litellm-rust/crates/core/src/error.rs
+++ b/litellm-rust/crates/core/src/error.rs
@@ -17,6 +17,10 @@ pub enum Error {
     InvalidRequest(String),
     #[error("{0}")]
     Auth(String),
+    #[error(
+        "Missing {provider} API Key - A call is being made to {provider} but no key is set either in the environment variables or via params"
+    )]
+    MissingApiKey { provider: &'static str },
     #[error("upstream request failed with status {status}: {body}")]
     Http { status: u16, body: String },
     #[error("upstream network error: {0}")]
@@ -36,6 +40,59 @@ pub enum Error {
     Unsupported(&'static str),
 }
 
+#[derive(Clone, Debug, ThisError, PartialEq, Eq)]
+pub enum TransportError {
+    #[error("upstream request failed with status {status}: {body}")]
+    Http { status: u16, body: String },
+    #[error("upstream network error: {0}")]
+    Network(String),
+    #[error("could not reach the provider: {0}")]
+    Connect(String),
+}
+
+impl TransportError {
+    pub fn from_reqwest_before_dispatch(error: reqwest::Error) -> Self {
+        let before_dispatch = !error.is_timeout() && (error.is_connect() || error.is_builder());
+        let message = error.without_url().to_string();
+        if before_dispatch {
+            Self::Connect(message)
+        } else {
+            Self::Network(message)
+        }
+    }
+}
+
+impl From<reqwest::Error> for TransportError {
+    fn from(error: reqwest::Error) -> Self {
+        Self::Network(error.without_url().to_string())
+    }
+}
+
+impl From<crate::ocr::error::OcrRequestError> for Error {
+    fn from(error: crate::ocr::error::OcrRequestError) -> Self {
+        match error {
+            crate::ocr::error::OcrRequestError::MissingField(field) => Self::MissingField(field),
+            error => Self::InvalidRequest(error.to_string()),
+        }
+    }
+}
+
+impl From<crate::ocr::error::OcrResponseError> for Error {
+    fn from(error: crate::ocr::error::OcrResponseError) -> Self {
+        Self::InvalidResponse(error.to_string())
+    }
+}
+
+impl From<TransportError> for Error {
+    fn from(error: TransportError) -> Self {
+        match error {
+            TransportError::Http { status, body } => Self::Http { status, body },
+            TransportError::Network(message) => Self::Network(message),
+            TransportError::Connect(message) => Self::Connect(message),
+        }
+    }
+}
+
 pub fn json_type_name(value: &serde_json::Value) -> &'static str {
     match value {
         serde_json::Value::Null => "null",
@@ -46,3 +103,53 @@ pub fn json_type_name(value: &serde_json::Value) -> &'static str {
         serde_json::Value::Object(_) => "object",
     }
 }
+
+#[cfg(test)]
+mod transport_tests {
+    use super::*;
+
+    #[tokio::test]
+    async fn transport_errors_remove_urls_and_keep_dispatch_context() {
+        let error = reqwest::Client::builder()
+            .no_proxy()
+            .build()
+            .expect("client")
+            .get("http://localhost:invalid/private?api_key=secret")
+            .send()
+            .await
+            .expect_err("invalid port");
+        let error = TransportError::from_reqwest_before_dispatch(error);
+        assert!(matches!(error, TransportError::Connect(_)));
+        assert!(!error.to_string().contains("secret"));
+        assert!(!error.to_string().contains("private"));
+    }
+
+    #[tokio::test]
+    async fn request_timeout_is_not_safe_to_retry_as_a_connect_failure() {
+        use std::time::Duration;
+        let listener = tokio::net::TcpListener::bind("127.0.0.1:0")
+            .await
+            .expect("bind");
+        let address = listener.local_addr().expect("address");
+        let request = reqwest::Client::builder()
+            .no_proxy()
+            .build()
+            .expect("client")
+            .get(format!("http://{address}"))
+            .timeout(Duration::from_millis(200))
+            .send();
+        let (response, accepted) = tokio::join!(
+            request,
+            tokio::time::timeout(Duration::from_secs(2), listener.accept())
+        );
+        let _connection = accepted
+            .expect("accept deadline")
+            .expect("accepted connection");
+        let error = response.expect_err("server does not respond");
+        assert!(error.is_timeout());
+        assert!(matches!(
+            TransportError::from_reqwest_before_dispatch(error),
+            TransportError::Network(_)
+        ));
+    }
+}
diff --git a/litellm-rust/crates/core/src/http_utils.rs b/litellm-rust/crates/core/src/http_utils.rs
index cb472dd5a57..9299bb77ac8 100644
--- a/litellm-rust/crates/core/src/http_utils.rs
+++ b/litellm-rust/crates/core/src/http_utils.rs
@@ -1,10 +1,43 @@
-//! Header and upstream-body helpers shared by every route module.
-
 use serde_json::{Map, Value};
 
 use crate::constants::UPSTREAM_ERROR_BODY_MAX_CHARS;
 use crate::error::{Error, json_type_name};
 
+#[allow(
+    dead_code,
+    reason = "used by the OCR architecture in the next stacked PR"
+)]
+pub(crate) enum HeaderPolicy<'a> {
+    All,
+    Only(&'a [&'a str]),
+    Except(&'a [&'a str]),
+}
+
+#[allow(
+    dead_code,
+    reason = "used by the OCR architecture in the next stacked PR"
+)]
+pub(crate) fn with_headers(
+    builder: reqwest::RequestBuilder,
+    headers: &[(String, String)],
+    policy: HeaderPolicy<'_>,
+) -> reqwest::RequestBuilder {
+    headers
+        .iter()
+        .filter(|(name, _)| match policy {
+            HeaderPolicy::All => true,
+            HeaderPolicy::Only(names) => names
+                .iter()
+                .any(|allowed| name.eq_ignore_ascii_case(allowed)),
+            HeaderPolicy::Except(names) => !names
+                .iter()
+                .any(|excluded| name.eq_ignore_ascii_case(excluded)),
+        })
+        .fold(builder, |builder, (name, value)| {
+            builder.header(name, value)
+        })
+}
+
 #[tracing::instrument(target = "litellm::function_trace", level = "trace", skip_all)]
 pub async fn http_request(
     request: reqwest::RequestBuilder,
@@ -12,8 +45,6 @@ pub async fn http_request(
     request.send().await
 }
 
-/// Bound an upstream error body before it crosses a host boundary, so provider
-/// bodies stay data-minimized.
 pub fn truncate_error_body(body: &str) -> String {
     if body.chars().count() <= UPSTREAM_ERROR_BODY_MAX_CHARS {
         return body.to_string();
@@ -61,11 +92,77 @@ pub fn has_bearer_auth(headers: &[(String, String)]) -> bool {
     })
 }
 
+#[allow(
+    dead_code,
+    reason = "used by the OCR architecture in the next stacked PR"
+)]
+pub(crate) fn deserialize_optional_param<'de, D, T>(
+    deserializer: D,
+) -> Result<Option<Option<T>>, D::Error>
+where
+    D: serde::Deserializer<'de>,
+    T: serde::Deserialize<'de>,
+{
+    <Option<T> as serde::Deserialize>::deserialize(deserializer).map(Some)
+}
+
 #[cfg(test)]
 mod tests {
     use super::*;
     use serde_json::json;
 
+    #[rstest::rstest]
+    #[case(HeaderPolicy::All, true, true)]
+    #[case(HeaderPolicy::Only(&["authorization"]), true, false)]
+    #[case(HeaderPolicy::Except(&["authorization"]), false, true)]
+    fn forwarding_policy_preserves_matching_headers_and_duplicates(
+        #[case] policy: HeaderPolicy<'_>,
+        #[case] auth: bool,
+        #[case] trace: bool,
+    ) {
+        let request = with_headers(
+            reqwest::Client::new().get("https://example.com"),
+            &[
+                ("AuThOrIzAtIoN".into(), "Bearer token".into()),
+                ("X-Trace".into(), "first".into()),
+                ("x-trace".into(), "second".into()),
+            ],
+            policy,
+        )
+        .build()
+        .unwrap();
+        assert_eq!(request.headers().contains_key("authorization"), auth);
+        let traces: Vec<_> = request.headers().get_all("x-trace").iter().collect();
+        if trace {
+            assert_eq!(traces, ["first", "second"]);
+        } else {
+            assert!(traces.is_empty());
+        }
+    }
+
+    #[test]
+    fn multipart_policy_leaves_content_headers_to_reqwest() {
+        let request = with_headers(
+            reqwest::Client::new()
+                .post("https://example.com")
+                .multipart(reqwest::multipart::Form::new().text("file", "abc")),
+            &[
+                ("Content-Type".into(), "application/json".into()),
+                ("CONTENT-LENGTH".into(), "0".into()),
+            ],
+            HeaderPolicy::Except(&["content-type", "content-length"]),
+        )
+        .build()
+        .unwrap();
+        assert!(
+            request.headers()["content-type"]
+                .to_str()
+                .unwrap()
+                .starts_with("multipart/form-data; boundary=")
+        );
+        assert_ne!(request.headers()["content-length"], "0");
+    }
+
     #[test]
     fn truncate_leaves_short_bodies_untouched() {
         assert_eq!(truncate_error_body("short"), "short");
diff --git a/litellm-rust/crates/core/src/lib.rs b/litellm-rust/crates/core/src/lib.rs
index b93e084f57e..3a0896a4d5a 100644
--- a/litellm-rust/crates/core/src/lib.rs
+++ b/litellm-rust/crates/core/src/lib.rs
@@ -14,5 +14,6 @@ pub mod realtime;
 pub mod responses;
 pub mod router;
 pub mod routing_utils;
+mod url_utils;
 
 pub use error::Error;
diff --git a/litellm-rust/crates/core/src/ocr/adapters/mistral.rs b/litellm-rust/crates/core/src/ocr/adapters/mistral.rs
new file mode 100644
index 00000000000..ea569ffb34f
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/adapters/mistral.rs
@@ -0,0 +1,147 @@
+use super::OcrAdapter;
+use crate::Error;
+use crate::constants::MISTRAL_OCR_API_BASE;
+use crate::ocr::OcrClient;
+use crate::ocr::codecs::mistral::{self, MistralOcrParams, MistralOcrResponse};
+use crate::ocr::error::{OcrError, OcrRequestError, OcrResponseError};
+use crate::ocr::prepare::{
+    _prepare_ocr_request, ParsedProviderParams, credential_env, transform_request_body,
+};
+use crate::ocr::registry::OcrProvider;
+use crate::ocr::types::{LiteLLMOcrRequest, LiteLLMOcrResponse, OcrConnection};
+use crate::url_utils::ApiUrl;
+
+const MISTRAL_API_KEY_ENV: &str = "MISTRAL_API_KEY";
+
+#[derive(Clone, Debug)]
+pub(crate) struct MistralAdapter;
+
+impl OcrAdapter for MistralAdapter {
+    type ProviderResponse = MistralOcrResponse;
+    const PROVIDER: OcrProvider = OcrProvider::Mistral;
+
+    async fn prepare_request(
+        &self,
+        request: &LiteLLMOcrRequest,
+        client: &OcrClient,
+    ) -> Result<reqwest::Request, OcrError> {
+        let ParsedProviderParams {
+            known: params,
+            extra_params: _extra_params,
+        } = _prepare_ocr_request::<MistralOcrParams>(request)?;
+        let headers = validate_environment(&request.connection, &credential_env)?;
+        let url = get_complete_url(request.connection.api_base.as_deref())?;
+        let body =
+            mistral::transform_ocr_request(&request.model, request.document.clone(), &params)?;
+        transform_request_body(client, request, &url, &headers, body, |_| Ok(())).await
+    }
+
+    fn transform_ocr_response(
+        &self,
+        request: &LiteLLMOcrRequest,
+        response: Self::ProviderResponse,
+    ) -> Result<LiteLLMOcrResponse, OcrResponseError> {
+        mistral::transform_ocr_response(&request.model, response)
+    }
+}
+
+pub(crate) fn get_complete_url(api_base: Option<&str>) -> Result<String, OcrError> {
+    let base = api_base
+        .map(str::trim)
+        .filter(|base| !base.is_empty())
+        .unwrap_or(MISTRAL_OCR_API_BASE);
+    ApiUrl::parse(base)
+        .and_then(|url| url.complete_path(&["v1", "ocr"]))
+        .map(|url| url.into_string())
+        .map_err(|_| {
+            OcrRequestError::RequestField {
+                path: "api_base".into(),
+            }
+            .into()
+        })
+}
+
+fn validate_environment(
+    connection: &OcrConnection,
+    env_lookup: &(dyn Fn(&str) -> Option<String> + Sync),
+) -> Result<Vec<(String, String)>, OcrError> {
+    if crate::http_utils::has_header(&connection.extra_headers, "authorization") {
+        return Ok(connection.extra_headers.clone());
+    }
+    let api_key = connection
+        .api_key
+        .as_deref()
+        .map(str::trim)
+        .filter(|key| !key.is_empty())
+        .map(str::to_string)
+        .or_else(|| env_lookup(MISTRAL_API_KEY_ENV).filter(|key| !key.trim().is_empty()))
+        .ok_or(Error::MissingApiKey {
+            provider: "Mistral",
+        })?;
+    Ok(
+        std::iter::once(("Authorization".into(), format!("Bearer {api_key}")))
+            .chain(connection.extra_headers.clone())
+            .collect(),
+    )
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn complete_url_defaults_and_dedupes_v1() {
+        assert_eq!(
+            get_complete_url(None).unwrap(),
+            "https://api.mistral.ai/v1/ocr"
+        );
+        assert_eq!(
+            get_complete_url(Some("https://example.com/v1?tenant=a")).unwrap(),
+            "https://example.com/v1/ocr?tenant=a"
+        );
+        assert_eq!(
+            get_complete_url(Some("https://example.com/v1/ocr?tenant=a")).unwrap(),
+            "https://example.com/v1/ocr?tenant=a"
+        );
+    }
+
+    #[test]
+    fn environment_prefers_explicit_key_then_environment() {
+        let explicit = OcrConnection {
+            api_key: Some("explicit".into()),
+            ..OcrConnection::default()
+        };
+        assert_eq!(
+            validate_environment(&explicit, &|_| Some("environment".into())).unwrap()[0],
+            ("Authorization".into(), "Bearer explicit".into())
+        );
+
+        assert_eq!(
+            validate_environment(&OcrConnection::default(), &|_| Some("environment".into()))
+                .unwrap()[0],
+            ("Authorization".into(), "Bearer environment".into())
+        );
+    }
+
+    #[test]
+    fn environment_preserves_forwarded_authorization() {
+        let connection = OcrConnection {
+            extra_headers: vec![("authorization".into(), "Bearer forwarded".into())],
+            ..OcrConnection::default()
+        };
+        assert_eq!(
+            validate_environment(&connection, &|_| None).unwrap(),
+            connection.extra_headers
+        );
+    }
+
+    #[test]
+    fn environment_rejects_missing_key() {
+        assert!(matches!(
+            validate_environment(&OcrConnection::default(), &|_| None),
+            Err(OcrError::Public(Error::MissingApiKey {
+                provider: "Mistral"
+            }))
+        ));
+    }
+}
diff --git a/litellm-rust/crates/core/src/ocr/adapters/mod.rs b/litellm-rust/crates/core/src/ocr/adapters/mod.rs
new file mode 100644
index 00000000000..7dfb08b4dc2
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/adapters/mod.rs
@@ -0,0 +1,69 @@
+use std::future::Future;
+
+use serde::de::DeserializeOwned;
+
+use super::OcrClient;
+use super::error::{OcrError, OcrResponseError};
+use super::registry::OcrProvider;
+use super::types::{LiteLLMOcrRequest, LiteLLMOcrResponse, OcrResponseFormat};
+use super::wire::DecodedOcrResponse;
+
+mod mistral;
+
+pub(crate) use mistral::MistralAdapter;
+
+/// Converts a complete LiteLLM OCR call to provider HTTP and normalizes its response.
+pub(crate) trait OcrAdapter: Send + Sync + Sized + 'static {
+    /// Provider JSON schema; direct and Vertex Mistral share `MistralOcrResponse`.
+    type ProviderResponse: DeserializeOwned + Send;
+
+    const PROVIDER: OcrProvider;
+
+    /// Prepares the complete provider HTTP request.
+    /// `request` contains the model, document, connection, and unmapped caller options.
+    /// `client` supplies reusable provider and document HTTP clients.
+    /// Returns the complete HTTP request, whereas Python returns body data.
+    fn prepare_request(
+        &self,
+        request: &LiteLLMOcrRequest,
+        client: &OcrClient,
+    ) -> impl Future<Output = Result<reqwest::Request, OcrError>> + Send;
+
+    /// Python: `transform_ocr_response`.
+    /// `request` supplies caller context, including the fallback model.
+    /// `response` is the decoded provider payload; the output is the shared LiteLLM schema.
+    fn transform_ocr_response(
+        &self,
+        request: &LiteLLMOcrRequest,
+        response: Self::ProviderResponse,
+    ) -> Result<LiteLLMOcrResponse, OcrResponseError>;
+
+    /// Decodes provider HTTP; adapters may override this to poll asynchronous operations.
+    /// Python performs that polling inside `async_transform_ocr_response`.
+    /// `client` is reused for polling; `response` is the initial HTTP response.
+    /// `url` and `headers` describe the submitted call; `request` supplies limits and format.
+    fn read_response(
+        &self,
+        _client: &OcrClient,
+        response: reqwest::Response,
+        _url: &str,
+        _headers: &[(String, String)],
+        request: &LiteLLMOcrRequest,
+    ) -> impl Future<Output = Result<DecodedOcrResponse<Self::ProviderResponse>, OcrError>> + Send
+    {
+        let retain_native = request
+            .response_format()
+            .map(|format| format == OcrResponseFormat::Native);
+        async move { super::client::read_json_response(response, retain_native?).await }
+    }
+}
+
+macro_rules! for_each_ocr_adapter {
+    ($callback:ident) => {
+        $callback! {
+            Mistral, $crate::ocr::adapters::MistralAdapter, $crate::ocr::adapters::MistralAdapter, Mistral;
+        }
+    };
+}
+
+pub(crate) use for_each_ocr_adapter;
diff --git a/litellm-rust/crates/core/src/ocr/client.rs b/litellm-rust/crates/core/src/ocr/client.rs
new file mode 100644
index 00000000000..36bfc036bae
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/client.rs
@@ -0,0 +1,75 @@
+use std::sync::OnceLock;
+use std::time::Duration;
+
+use serde::de::DeserializeOwned;
+
+use super::error::OcrError;
+use super::handler::perform_ocr_request;
+use super::types::{LiteLLMOcrRequest, LiteLLMOcrResponse};
+use super::wire::{DecodedOcrResponse, decode_response};
+use crate::Error;
+use crate::constants::OCR_CONNECT_TIMEOUT_SECS;
+use crate::error::TransportError;
+
+#[derive(Clone)]
+pub struct OcrClient {
+    provider_http: reqwest::Client,
+}
+
+impl OcrClient {
+    pub fn new(provider_http: reqwest::Client) -> Result<Self, TransportError> {
+        Ok(Self { provider_http })
+    }
+
+    #[tracing::instrument(
+        name = "ocr",
+        target = "litellm::function_trace",
+        level = "trace",
+        skip_all
+    )]
+    pub async fn perform(&self, request: LiteLLMOcrRequest) -> Result<LiteLLMOcrResponse, Error> {
+        perform_ocr_request(self, request).await
+    }
+
+    pub(crate) fn provider_http(&self) -> &reqwest::Client {
+        &self.provider_http
+    }
+
+    #[cfg(test)]
+    pub(crate) fn for_test(provider_http: reqwest::Client) -> Self {
+        Self { provider_http }
+    }
+}
+
+pub async fn ocr(request: LiteLLMOcrRequest) -> Result<LiteLLMOcrResponse, Error> {
+    static CLIENT: OnceLock<Result<OcrClient, TransportError>> = OnceLock::new();
+    let client = CLIENT
+        .get_or_init(|| {
+            reqwest::Client::builder()
+                .connect_timeout(Duration::from_secs(OCR_CONNECT_TIMEOUT_SECS))
+                .build()
+                .map_err(TransportError::from)
+                .and_then(OcrClient::new)
+        })
+        .clone()?;
+    client.perform(request).await
+}
+
+pub async fn read_json_response<T: DeserializeOwned>(
+    response: reqwest::Response,
+    native: bool,
+) -> Result<DecodedOcrResponse<T>, OcrError> {
+    let status = response.status();
+    let bytes = response
+        .bytes()
+        .await
+        .map_err(crate::error::TransportError::from)?;
+    if !status.is_success() {
+        return Err(crate::error::TransportError::Http {
+            status: status.as_u16(),
+            body: crate::http_utils::truncate_error_body(&String::from_utf8_lossy(&bytes)),
+        }
+        .into());
+    }
+    Ok(decode_response(&bytes, native)?)
+}
diff --git a/litellm-rust/crates/core/src/ocr/codecs/mistral/mod.rs b/litellm-rust/crates/core/src/ocr/codecs/mistral/mod.rs
new file mode 100644
index 00000000000..eea4254779e
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/codecs/mistral/mod.rs
@@ -0,0 +1,5 @@
+mod transformation;
+mod types;
+
+pub(crate) use transformation::{transform_ocr_request, transform_ocr_response};
+pub(crate) use types::{MistralOcrParams, MistralOcrRequest, MistralOcrResponse};
diff --git a/litellm-rust/crates/core/src/ocr/codecs/mistral/transformation.rs b/litellm-rust/crates/core/src/ocr/codecs/mistral/transformation.rs
new file mode 100644
index 00000000000..cd0a1dc6b17
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/codecs/mistral/transformation.rs
@@ -0,0 +1,102 @@
+use super::{MistralOcrParams, MistralOcrRequest, MistralOcrResponse};
+use crate::ocr::error::{OcrRequestError, OcrResponseError};
+use crate::ocr::types::{LiteLLMOcrResponse, OcrDocument};
+
+#[tracing::instrument(target = "litellm::function_trace", level = "trace", skip_all)]
+pub(crate) fn transform_ocr_request(
+    model: &str,
+    document: OcrDocument,
+    params: &MistralOcrParams,
+) -> Result<MistralOcrRequest, OcrRequestError> {
+    Ok(MistralOcrRequest {
+        model: model.to_string(),
+        document,
+        params: params.clone(),
+    })
+}
+
+pub(crate) fn transform_ocr_response(
+    model: &str,
+    response: MistralOcrResponse,
+) -> Result<LiteLLMOcrResponse, OcrResponseError> {
+    Ok(LiteLLMOcrResponse {
+        pages: response.pages,
+        model: response.model.unwrap_or_else(|| model.to_string()),
+        document_annotation: response.document_annotation,
+        usage_info: response.usage_info,
+        object: "ocr".to_string(),
+        extra_fields: response.extra_fields,
+        provider_native_response: None,
+    })
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use rstest::rstest;
+    use serde_json::{Value, json};
+
+    #[rstest]
+    #[case("pages", json!([0, 2]))]
+    #[case("include_image_base64", json!(true))]
+    #[case("image_limit", json!(2))]
+    #[case("image_min_size", json!(100))]
+    #[case("bbox_annotation_format", json!({"type":"json_schema"}))]
+    #[case("document_annotation_format", json!({"type":"json_schema"}))]
+    #[case("document_annotation_prompt", json!("extract"))]
+    #[case("extract_header", json!(true))]
+    #[case("extract_footer", json!(false))]
+    #[case("table_format", json!("html"))]
+    #[case("confidence_scores_granularity", json!("word"))]
+    #[case("include_blocks", json!(true))]
+    #[case("id", json!("req-123"))]
+    fn request_mapping_matches_python(#[case] name: &str, #[case] value: Value) {
+        let params: MistralOcrParams =
+            serde_json::from_value(json!({name: value.clone()})).unwrap();
+        let document: OcrDocument = serde_json::from_value(
+            json!({"type":"document_url","document_url":"https://example.com/a.pdf"}),
+        )
+        .unwrap();
+        let result =
+            serde_json::to_value(transform_ocr_request("model", document, &params).unwrap())
+                .unwrap();
+        assert_eq!(result["model"], "model");
+        assert_eq!(result[name], value);
+    }
+
+    #[test]
+    fn request_mapping_filters_unknown_fields() {
+        let params: MistralOcrParams = serde_json::from_value(json!({"unknown": true})).unwrap();
+        let document: OcrDocument = serde_json::from_value(
+            json!({"type":"document_url","document_url":"https://example.com/a.pdf"}),
+        )
+        .unwrap();
+        let result =
+            serde_json::to_value(transform_ocr_request("model", document, &params).unwrap())
+                .unwrap();
+        assert!(result.get("unknown").is_none());
+    }
+
+    #[test]
+    fn response_preserves_provider_fields() {
+        let response: MistralOcrResponse = serde_json::from_value(json!({
+            "pages":[{"index":0,"markdown":"hello","header":"head","confidence_scores":{"mean":0.99}}],
+            "model":"returned-model",
+            "usage_info":{"pages_processed":1,"future_counter":5},
+            "future_response_field":"kept"
+        }))
+        .unwrap();
+        let result = transform_ocr_response("model", response)
+            .unwrap()
+            .into_json();
+        assert_eq!(result["pages"][0]["header"], "head");
+        assert_eq!(result["usage_info"]["future_counter"], 5);
+        assert_eq!(result["future_response_field"], "kept");
+        assert_eq!(result["model"], "returned-model");
+    }
+
+    #[test]
+    fn response_rejects_null_pages() {
+        assert!(serde_json::from_value::<MistralOcrResponse>(json!({"pages":null})).is_err());
+    }
+}
diff --git a/litellm-rust/crates/core/src/ocr/codecs/mistral/types.rs b/litellm-rust/crates/core/src/ocr/codecs/mistral/types.rs
new file mode 100644
index 00000000000..0e601cd8319
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/codecs/mistral/types.rs
@@ -0,0 +1,53 @@
+use serde::{Deserialize, Serialize};
+use serde_json::{Map, Value};
+
+use crate::ocr::types::OcrDocument;
+
+#[derive(Clone, Debug, Default, PartialEq, Serialize, Deserialize)]
+pub(crate) struct MistralOcrParams {
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub pages: Option<Vec<i64>>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub include_image_base64: Option<bool>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub image_limit: Option<i64>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub image_min_size: Option<i64>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub bbox_annotation_format: Option<Value>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub document_annotation_format: Option<Value>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub document_annotation_prompt: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub extract_header: Option<bool>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub extract_footer: Option<bool>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub table_format: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub confidence_scores_granularity: Option<String>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub include_blocks: Option<bool>,
+    #[serde(skip_serializing_if = "Option::is_none")]
+    pub id: Option<String>,
+}
+
+#[derive(Clone, Debug, Serialize, Deserialize)]
+pub(crate) struct MistralOcrRequest {
+    pub model: String,
+    pub document: OcrDocument,
+    #[serde(flatten)]
+    pub params: MistralOcrParams,
+}
+
+#[derive(Clone, Debug, Default, Deserialize)]
+pub(crate) struct MistralOcrResponse {
+    #[serde(default)]
+    pub pages: Vec<Value>,
+    pub model: Option<String>,
+    pub document_annotation: Option<Value>,
+    pub usage_info: Option<Value>,
+    #[serde(flatten)]
+    pub extra_fields: Map<String, Value>,
+}
diff --git a/litellm-rust/crates/core/src/ocr/codecs/mod.rs b/litellm-rust/crates/core/src/ocr/codecs/mod.rs
new file mode 100644
index 00000000000..170ef5f68a7
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/codecs/mod.rs
@@ -0,0 +1 @@
+pub(crate) mod mistral;
diff --git a/litellm-rust/crates/core/src/ocr/error.rs b/litellm-rust/crates/core/src/ocr/error.rs
new file mode 100644
index 00000000000..50793aad566
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/error.rs
@@ -0,0 +1,42 @@
+use thiserror::Error;
+
+use crate::error::TransportError;
+
+#[derive(Debug, Clone, PartialEq, Eq, Error)]
+pub enum OcrRequestError {
+    #[error("Invalid `req_format`. Expected 'native' or 'litellm'.")]
+    RequestFormat,
+    #[error("invalid OCR request field: {path}")]
+    RequestField { path: String },
+    #[error("missing required field: {0}")]
+    MissingField(&'static str),
+}
+
+#[derive(Debug, Clone, PartialEq, Eq, Error)]
+pub enum OcrResponseError {
+    #[error("invalid OCR response field: {path}")]
+    ResponseField { path: String },
+}
+
+#[derive(Debug, Error)]
+pub enum OcrError {
+    #[error("{0}")]
+    Request(#[from] OcrRequestError),
+    #[error("{0}")]
+    Response(#[from] OcrResponseError),
+    #[error("{0}")]
+    Transport(#[from] TransportError),
+    #[error("{0}")]
+    Public(#[from] crate::Error),
+}
+
+impl From<OcrError> for crate::Error {
+    fn from(error: OcrError) -> Self {
+        match error {
+            OcrError::Request(error) => error.into(),
+            OcrError::Response(error) => error.into(),
+            OcrError::Transport(error) => error.into(),
+            OcrError::Public(error) => error,
+        }
+    }
+}
diff --git a/litellm-rust/crates/core/src/ocr/handler.rs b/litellm-rust/crates/core/src/ocr/handler.rs
new file mode 100644
index 00000000000..0b04319d966
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/handler.rs
@@ -0,0 +1,72 @@
+use super::OcrClient;
+use super::adapters::OcrAdapter;
+use super::hooks::OcrLifecycleHooks;
+use super::registry::OcrAdapterKind;
+use super::types::{LiteLLMOcrRequest, LiteLLMOcrResponse};
+use crate::Error;
+use crate::call_lifecycle::{CallLifecycle, CallLifecycleContext};
+
+pub(crate) async fn perform_ocr_request(
+    client: &OcrClient,
+    request: LiteLLMOcrRequest,
+) -> Result<LiteLLMOcrResponse, Error> {
+    let context = CallLifecycleContext::new(
+        "ocr",
+        request.model.clone(),
+        request.adapter.provider().as_str(),
+        request
+            .litellm_call_id
+            .clone()
+            .unwrap_or_else(|| format!("ocr-{:032x}", rand::random::<u128>())),
+    );
+    let hooks = OcrLifecycleHooks {
+        hooks: request.hooks.clone(),
+        provider_name: context.custom_llm_provider.clone(),
+    };
+    CallLifecycle::default().run(context, request, &hooks, |request| async move {
+        macro_rules! execute_selected_adapter {
+            ($( $variant:ident, $adapter:ty, $instance:expr, $provider:ident; )+) => {
+                match request.adapter {
+                    $( OcrAdapterKind::$variant => execute_ocr_provider_call(client, &$instance, request).await, )+
+                }
+            };
+        }
+        super::adapters::for_each_ocr_adapter!(execute_selected_adapter)
+    }).await
+}
+
+#[tracing::instrument(target = "litellm::function_trace", level = "trace", skip_all)]
+async fn execute_ocr_provider_call<A: OcrAdapter>(
+    client: &OcrClient,
+    adapter: &A,
+    request: LiteLLMOcrRequest,
+) -> Result<LiteLLMOcrResponse, Error> {
+    let provider_request = adapter.prepare_request(&request, client).await?;
+    let url = provider_request.url().to_string();
+    let headers = provider_request
+        .headers()
+        .iter()
+        .map(|(name, value)| {
+            value
+                .to_str()
+                .map(|value| (name.to_string(), value.to_string()))
+                .map_err(|_| super::error::OcrRequestError::RequestField {
+                    path: "headers".into(),
+                })
+        })
+        .collect::<Result<Vec<_>, _>>()?;
+    let response = crate::http_utils::http_request(reqwest::RequestBuilder::from_parts(
+        client.provider_http().clone(),
+        provider_request,
+    ))
+    .await
+    .map_err(crate::error::TransportError::from)?;
+    let decoded = adapter
+        .read_response(client, response, &url, &headers, &request)
+        .await?;
+    let response = adapter.transform_ocr_response(&request, decoded.data)?;
+    Ok(LiteLLMOcrResponse {
+        provider_native_response: decoded.native,
+        ..response
+    })
+}
diff --git a/litellm-rust/crates/core/src/ocr/hooks.rs b/litellm-rust/crates/core/src/ocr/hooks.rs
new file mode 100644
index 00000000000..7dd3c6bf8b2
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/hooks.rs
@@ -0,0 +1,146 @@
+use std::future::Future;
+use std::pin::Pin;
+use std::sync::Arc;
+
+use super::types::{LiteLLMOcrRequest, LiteLLMOcrResponse, OcrDocument};
+use crate::Error;
+use crate::call_lifecycle::{CallLifecycleContext, CallLifecycleHooks, CallLifecycleTiming};
+use serde::Serialize;
+use serde_json::Value;
+
+pub type OcrHookFuture<'a, T> = Pin<Box<dyn Future<Output = Result<T, Error>> + Send + 'a>>;
+pub type OcrLogFuture<'a> = Pin<Box<dyn Future<Output = ()> + Send + 'a>>;
+
+#[derive(Clone, Debug, Serialize)]
+pub struct OcrPreCallRequest {
+    pub model: String,
+    pub custom_llm_provider: String,
+    pub document: OcrDocument,
+    pub optional_params: Value,
+}
+
+#[derive(Clone, Debug, Serialize)]
+pub struct OcrDuringCallRequest {
+    pub model: String,
+    pub custom_llm_provider: String,
+    pub url: String,
+    pub body: Value,
+}
+
+pub trait OcrHooks: Send + Sync {
+    fn has_guardrails(&self) -> bool {
+        false
+    }
+    fn pre_call(&self, request: OcrPreCallRequest) -> OcrHookFuture<'_, OcrPreCallRequest> {
+        Box::pin(async move { Ok(request) })
+    }
+    fn during_call(
+        &self,
+        request: OcrDuringCallRequest,
+    ) -> OcrHookFuture<'_, OcrDuringCallRequest> {
+        Box::pin(async move { Ok(request) })
+    }
+    fn success<'a>(
+        &'a self,
+        _context: &'a CallLifecycleContext,
+        _response: &'a LiteLLMOcrResponse,
+        _timing: &'a CallLifecycleTiming,
+    ) -> OcrLogFuture<'a> {
+        Box::pin(async {})
+    }
+    fn failure<'a>(
+        &'a self,
+        _context: &'a CallLifecycleContext,
+        _error: &'a Error,
+        _timing: &'a CallLifecycleTiming,
+    ) -> OcrLogFuture<'a> {
+        Box::pin(async {})
+    }
+}
+
+pub struct NoopOcrHooks;
+impl OcrHooks for NoopOcrHooks {}
+
+pub(crate) struct OcrLifecycleHooks {
+    pub hooks: Arc<dyn OcrHooks>,
+    pub provider_name: String,
+}
+
+impl CallLifecycleHooks<LiteLLMOcrRequest, LiteLLMOcrRequest, LiteLLMOcrResponse>
+    for OcrLifecycleHooks
+{
+    type PreCallFuture<'a> = OcrHookFuture<'a, LiteLLMOcrRequest>;
+    type DuringCallFuture<'a> = OcrHookFuture<'a, LiteLLMOcrRequest>;
+    type SuccessFuture<'a> = OcrLogFuture<'a>;
+    type FailureFuture<'a> = OcrLogFuture<'a>;
+
+    fn async_pre_call_hook<'a>(
+        &'a self,
+        _context: &'a CallLifecycleContext,
+        request: LiteLLMOcrRequest,
+    ) -> Self::PreCallFuture<'a> {
+        Box::pin(async move {
+            if !self.hooks.has_guardrails() {
+                return Ok(request);
+            }
+            let changed = self
+                .hooks
+                .pre_call(OcrPreCallRequest {
+                    model: request.model.clone(),
+                    custom_llm_provider: self.provider_name.clone(),
+                    document: request.document,
+                    optional_params: Value::Object(request.optional_params),
+                })
+                .await?;
+            let Value::Object(optional_params) = changed.optional_params else {
+                return Err(super::error::OcrRequestError::RequestField {
+                    path: "guardrail.optional_params".into(),
+                }
+                .into());
+            };
+            Ok(LiteLLMOcrRequest {
+                document: changed.document,
+                optional_params,
+                ..request
+            })
+        })
+    }
+
+    fn async_during_call_hook<'a>(
+        &'a self,
+        _context: &'a CallLifecycleContext,
+        request: LiteLLMOcrRequest,
+    ) -> Self::DuringCallFuture<'a> {
+        Box::pin(async move { Ok(request) })
+    }
+
+    #[tracing::instrument(
+        name = "success_callback",
+        target = "litellm::function_trace",
+        level = "trace",
+        skip_all
+    )]
+    fn async_log_success_event<'a>(
+        &'a self,
+        context: &'a CallLifecycleContext,
+        response: &'a LiteLLMOcrResponse,
+        timing: &'a CallLifecycleTiming,
+    ) -> Self::SuccessFuture<'a> {
+        self.hooks.success(context, response, timing)
+    }
+
+    #[tracing::instrument(
+        name = "failure_callback",
+        target = "litellm::function_trace",
+        level = "trace",
+        skip_all
+    )]
+    fn async_log_failure_event<'a>(
+        &'a self,
+        context: &'a CallLifecycleContext,
+        error: &'a Error,
+        timing: &'a CallLifecycleTiming,
+    ) -> Self::FailureFuture<'a> {
+        self.hooks.failure(context, error, timing)
+    }
+}
diff --git a/litellm-rust/crates/core/src/ocr/mod.rs b/litellm-rust/crates/core/src/ocr/mod.rs
index ec2fbb969a6..78c86aeaa0e 100644
--- a/litellm-rust/crates/core/src/ocr/mod.rs
+++ b/litellm-rust/crates/core/src/ocr/mod.rs
@@ -1,2 +1,21 @@
+mod adapters;
+pub mod client;
+mod codecs;
+pub mod error;
+mod handler;
+pub mod hooks;
+mod prepare;
+mod registry;
 pub mod transformation;
 pub mod types;
+pub mod wire;
+
+pub use client::{OcrClient, ocr};
+pub use types::{LiteLLMOcrRequest, LiteLLMOcrResponse, OcrConnection, OcrDocument};
+
+#[cfg(test)]
+#[path = "../../tests/ocr/support.rs"]
+pub(crate) mod test_support;
+#[cfg(test)]
+#[path = "../../tests/ocr.rs"]
+pub(crate) mod tests;
diff --git a/litellm-rust/crates/core/src/ocr/prepare.rs b/litellm-rust/crates/core/src/ocr/prepare.rs
new file mode 100644
index 00000000000..cff40b7de50
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/prepare.rs
@@ -0,0 +1,142 @@
+use serde::{Deserialize, Serialize, de::DeserializeOwned};
+use serde_json::{Map, Value};
+
+use super::OcrClient;
+use super::error::{OcrError, OcrRequestError};
+use super::hooks::OcrDuringCallRequest;
+use super::types::LiteLLMOcrRequest;
+
+#[derive(Debug, Deserialize)]
+pub(crate) struct ParsedProviderParams<T> {
+    #[serde(flatten)]
+    pub known: T,
+    #[serde(default, flatten)]
+    pub extra_params: Map<String, Value>,
+}
+
+#[tracing::instrument(target = "litellm::function_trace", level = "trace", skip_all)]
+pub(crate) fn _prepare_ocr_request<T: DeserializeOwned>(
+    request: &LiteLLMOcrRequest,
+) -> Result<ParsedProviderParams<T>, OcrRequestError> {
+    super::wire::decode_request_value(
+        Value::Object(request.optional_params.clone()),
+        "optional_params",
+    )
+}
+
+pub(crate) async fn transform_request_body<B>(
+    client: &OcrClient,
+    request: &LiteLLMOcrRequest,
+    url: &str,
+    headers: &[(String, String)],
+    body: B,
+    validate: impl FnOnce(&B) -> Result<(), OcrRequestError>,
+) -> Result<reqwest::Request, OcrError>
+where
+    B: Serialize + DeserializeOwned,
+{
+    let body = if request.hooks.has_guardrails() {
+        let changed = request
+            .hooks
+            .during_call(OcrDuringCallRequest {
+                model: request.model.clone(),
+                custom_llm_provider: request.adapter.provider().as_str().into(),
+                url: url.into(),
+                body: serde_json::to_value(body).map_err(|_| OcrRequestError::RequestField {
+                    path: "body".into(),
+                })?,
+            })
+            .await?;
+        let body = OcrWireBody::<B>::decode(changed.body)?;
+        validate(&body.body)?;
+        body
+    } else {
+        OcrWireBody {
+            body,
+            extra: Map::new(),
+        }
+    };
+    build_http_request(client, request, url, headers, &body)
+}
+
+pub(crate) fn build_http_request<B: Serialize>(
+    client: &OcrClient,
+    request: &LiteLLMOcrRequest,
+    url: &str,
+    headers: &[(String, String)],
+    body: &B,
+) -> Result<reqwest::Request, OcrError> {
+    let builder = client
+        .provider_http()
+        .post(url)
+        .json(body)
+        .timeout(request.connection.timeout);
+    crate::http_utils::with_headers(builder, headers, crate::http_utils::HeaderPolicy::All)
+        .build()
+        .map_err(crate::error::TransportError::from)
+        .map_err(OcrError::from)
+}
+
+#[derive(Serialize)]
+struct OcrWireBody<B> {
+    #[serde(flatten)]
+    body: B,
+    #[serde(flatten)]
+    extra: Map<String, Value>,
+}
+
+impl<B: Serialize + DeserializeOwned> OcrWireBody<B> {
+    fn decode(value: Value) -> Result<Self, OcrRequestError> {
+        let body: B = super::wire::decode_request_value(value.clone(), "guardrail.body")?;
+        let Value::Object(fields) = value else {
+            return Err(OcrRequestError::RequestField {
+                path: "guardrail.body".into(),
+            });
+        };
+        let known = serde_json::to_value(&body).map_err(|_| OcrRequestError::RequestField {
+            path: "guardrail.body".into(),
+        })?;
+        let extra = fields
+            .into_iter()
+            .filter(|(key, _)| known.get(key).is_none())
+            .collect();
+        Ok(Self { body, extra })
+    }
+}
+
+pub(crate) fn credential_env(name: &str) -> Option<String> {
+    std::env::var(name).ok()
+}
+
+#[cfg(test)]
+mod tests {
+    use serde_json::json;
+
+    use super::*;
+
+    #[derive(Debug, Deserialize, PartialEq)]
+    struct KnownParams {
+        pages: Option<Vec<i64>>,
+    }
+
+    #[test]
+    fn parsed_provider_params_separates_known_and_extra_params() {
+        let parsed: ParsedProviderParams<KnownParams> = super::super::wire::decode_request_value(
+            json!({
+                "pages": [0, 2],
+                "future_ocr_option": true,
+                "extra_body": {"provider_option": "value"}
+            }),
+            "optional_params",
+        )
+        .unwrap();
+
+        assert_eq!(parsed.known.pages, Some(vec![0, 2]));
+        assert_eq!(parsed.extra_params["future_ocr_option"], true);
+        assert_eq!(
+            parsed.extra_params["extra_body"],
+            json!({"provider_option": "value"})
+        );
+        assert_eq!(parsed.extra_params.len(), 2);
+    }
+}
diff --git a/litellm-rust/crates/core/src/ocr/registry.rs b/litellm-rust/crates/core/src/ocr/registry.rs
new file mode 100644
index 00000000000..9bae8153ee8
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/registry.rs
@@ -0,0 +1,53 @@
+use super::adapters::OcrAdapter;
+use crate::Error;
+use crate::routing_utils::provider::{CustomLlmProvider, get_custom_llm_provider};
+
+macro_rules! define_adapter_types {
+    ($( $variant:ident, $adapter:ty, $instance:expr, $provider:ident; )+) => {
+        #[derive(Clone, Copy, Debug, PartialEq, Eq)]
+        pub(crate) enum OcrAdapterKind {
+            $( $variant, )+
+        }
+
+        impl OcrAdapterKind {
+            pub(crate) const fn provider(self) -> OcrProvider {
+                match self {
+                    $( Self::$variant => <$adapter>::PROVIDER, )+
+                }
+            }
+        }
+    };
+}
+
+super::adapters::for_each_ocr_adapter!(define_adapter_types);
+
+#[derive(Clone, Copy, Debug, PartialEq, Eq)]
+pub(crate) enum OcrProvider {
+    Mistral,
+}
+
+impl OcrProvider {
+    pub(crate) const fn as_str(self) -> &'static str {
+        match self {
+            Self::Mistral => "mistral",
+        }
+    }
+}
+
+pub(crate) fn resolve_wire_adapter(
+    model: &str,
+    custom_llm_provider: Option<&str>,
+) -> Result<(String, OcrAdapterKind), Error> {
+    let provider =
+        get_custom_llm_provider(model, custom_llm_provider).unwrap_or(CustomLlmProvider {
+            model,
+            custom_llm_provider: OcrProvider::Mistral.as_str(),
+        });
+    let typed_provider = match provider.custom_llm_provider {
+        "mistral" => OcrProvider::Mistral,
+        value => return Err(Error::InvalidProvider(value.to_string())),
+    };
+    match typed_provider {
+        OcrProvider::Mistral => Ok((provider.model.to_string(), OcrAdapterKind::Mistral)),
+    }
+}
diff --git a/litellm-rust/crates/core/src/ocr/transformation.rs b/litellm-rust/crates/core/src/ocr/transformation.rs
index 62299faf9ed..ac4f10bf15b 100644
--- a/litellm-rust/crates/core/src/ocr/transformation.rs
+++ b/litellm-rust/crates/core/src/ocr/transformation.rs
@@ -1,7 +1,7 @@
 use crate::Error;
 use serde_json::{Map, Value};
 
-use super::types::{OcrRequestData, OcrResponseData};
+use super::types::{LiteLLMOcrResponse, OcrRequestData};
 
 #[derive(Clone, Copy, Debug, PartialEq, Eq)]
 pub enum OcrAuthStrategy {
@@ -49,14 +49,14 @@ pub trait OcrProviderConfig: Sync {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error>;
+    ) -> Result<LiteLLMOcrResponse, Error>;
 
     fn transform_ocr_response_with_params(
         &self,
         model: &str,
         response_json: Value,
         _optional_params: &Map<String, Value>,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         self.transform_ocr_response(model, response_json)
     }
 
diff --git a/litellm-rust/crates/core/src/ocr/types.rs b/litellm-rust/crates/core/src/ocr/types.rs
index 71cdb232a87..02b5330188c 100644
--- a/litellm-rust/crates/core/src/ocr/types.rs
+++ b/litellm-rust/crates/core/src/ocr/types.rs
@@ -1,6 +1,14 @@
+use std::sync::Arc;
+use std::time::Duration;
+
 use serde::{Deserialize, Serialize};
 use serde_json::{Map, Value};
 
+use super::hooks::{NoopOcrHooks, OcrHooks};
+use super::registry::{OcrAdapterKind, resolve_wire_adapter};
+use crate::Error;
+use crate::constants::OCR_HTTP_TIMEOUT_SECS;
+
 #[derive(Clone, Debug, PartialEq, Serialize, Deserialize)]
 pub struct OcrRequestData {
     pub data: Value,
@@ -8,31 +16,145 @@ pub struct OcrRequestData {
 }
 
 #[derive(Clone, Debug, PartialEq, Serialize, Deserialize)]
-pub struct OcrResponseData {
+#[serde(tag = "type")]
+pub enum OcrDocument {
+    #[serde(rename = "document_url")]
+    DocumentUrl {
+        document_url: String,
+        #[serde(flatten)]
+        extra_fields: Map<String, Value>,
+    },
+    #[serde(rename = "image_url")]
+    ImageUrl {
+        image_url: String,
+        #[serde(flatten)]
+        extra_fields: Map<String, Value>,
+    },
+}
+
+#[derive(Clone, Copy, Debug, Default, PartialEq, Eq, Serialize, Deserialize)]
+#[serde(rename_all = "lowercase")]
+pub enum OcrResponseFormat {
+    #[default]
+    Litellm,
+    Native,
+}
+
+#[derive(Clone)]
+pub struct OcrConnection {
+    pub api_key: Option<String>,
+    pub api_base: Option<String>,
+    pub extra_headers: Vec<(String, String)>,
+    pub timeout: Duration,
+}
+
+impl Default for OcrConnection {
+    fn default() -> Self {
+        Self {
+            api_key: None,
+            api_base: None,
+            extra_headers: Vec::new(),
+            timeout: Duration::from_secs(OCR_HTTP_TIMEOUT_SECS),
+        }
+    }
+}
+
+pub struct LiteLLMOcrRequest {
+    pub model: String,
+    pub document: OcrDocument,
+    pub connection: OcrConnection,
+    pub hooks: Arc<dyn OcrHooks>,
+    pub litellm_call_id: Option<String>,
+    pub optional_params: Map<String, Value>,
+    pub(crate) adapter: OcrAdapterKind,
+}
+
+impl LiteLLMOcrRequest {
+    pub fn new(
+        model: String,
+        document: OcrDocument,
+        custom_llm_provider: Option<&str>,
+        optional_params: Map<String, Value>,
+    ) -> Result<Self, Error> {
+        let (model, adapter_kind) = resolve_wire_adapter(&model, custom_llm_provider)?;
+
+        Ok(Self {
+            model,
+            document,
+            connection: OcrConnection::default(),
+            hooks: Arc::new(NoopOcrHooks),
+            litellm_call_id: None,
+            optional_params,
+            adapter: adapter_kind,
+        })
+    }
+
+    pub(crate) fn response_format(
+        &self,
+    ) -> Result<OcrResponseFormat, super::error::OcrRequestError> {
+        self.optional_params
+            .get("req_format")
+            .map(|value| {
+                serde_json::from_value(value.clone())
+                    .map_err(|_| super::error::OcrRequestError::RequestFormat)
+            })
+            .transpose()
+            .map(|format| format.unwrap_or_default())
+    }
+
+    pub fn with_host_hooks(
+        self,
+        hooks: Arc<dyn OcrHooks>,
+        litellm_call_id: Option<String>,
+    ) -> Self {
+        Self {
+            hooks,
+            litellm_call_id,
+            ..self
+        }
+    }
+}
+
+#[derive(Clone, Debug, PartialEq, Serialize, Deserialize)]
+pub struct LiteLLMOcrResponse {
     pub pages: Vec<Value>,
     pub model: String,
     pub document_annotation: Option<Value>,
     pub usage_info: Option<Value>,
     pub object: String,
+    #[serde(flatten)]
     pub extra_fields: Map<String, Value>,
+    #[serde(skip_serializing_if = "Option::is_none")]
     pub provider_native_response: Option<Value>,
 }
 
-impl OcrResponseData {
+impl LiteLLMOcrResponse {
     pub fn into_json(self) -> Value {
-        let mut response = serde_json::json!({
-            "pages": self.pages,
-            "model": self.model,
-            "document_annotation": self.document_annotation,
-            "usage_info": self.usage_info,
-            "object": self.object,
-        });
-        if let Value::Object(object) = &mut response {
-            object.extend(self.extra_fields);
-            if let Some(native_response) = self.provider_native_response {
-                object.insert("provider_native_response".to_string(), native_response);
-            }
-        }
-        response
+        serde_json::to_value(self).expect("OCR response fields are JSON-compatible")
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+    use serde_json::json;
+
+    #[test]
+    fn response_serialization_flattens_extra_fields_and_omits_absent_native_response() {
+        let response = LiteLLMOcrResponse {
+            pages: vec![],
+            model: "model".into(),
+            document_annotation: None,
+            usage_info: None,
+            object: "ocr".into(),
+            extra_fields: json!({"provider_field":"kept"})
+                .as_object()
+                .unwrap()
+                .clone(),
+            provider_native_response: None,
+        };
+        let serialized = response.into_json();
+        assert_eq!(serialized["provider_field"], "kept");
+        assert!(serialized.get("provider_native_response").is_none());
     }
 }
diff --git a/litellm-rust/crates/core/src/ocr/wire.rs b/litellm-rust/crates/core/src/ocr/wire.rs
new file mode 100644
index 00000000000..f37c06a01ac
--- /dev/null
+++ b/litellm-rust/crates/core/src/ocr/wire.rs
@@ -0,0 +1,154 @@
+use crate::ocr::error::OcrRequestError;
+use crate::ocr::error::OcrResponseError;
+use std::time::Duration;
+
+use super::hooks::{OcrDuringCallRequest, OcrPreCallRequest};
+use super::types::{LiteLLMOcrRequest, OcrConnection, OcrDocument};
+use crate::Error;
+use serde::{
+    Deserialize,
+    de::{DeserializeOwned, IntoDeserializer},
+};
+use serde_json::{Map, Value};
+
+#[derive(Debug)]
+pub struct DecodedOcrResponse<T> {
+    pub data: T,
+    pub native: Option<Value>,
+}
+
+#[derive(Deserialize)]
+#[serde(deny_unknown_fields)]
+pub struct OcrWireRequest {
+    pub model: String,
+    pub document: Value,
+    pub api_key: Option<String>,
+    pub api_base: Option<String>,
+    pub custom_llm_provider: Option<String>,
+    pub extra_headers: Option<Map<String, Value>>,
+    #[serde(default)]
+    pub optional_params: Map<String, Value>,
+    pub timeout_seconds: Option<f64>,
+}
+
+pub fn is_supported_request(model: &str, custom_llm_provider: Option<&str>) -> bool {
+    super::registry::resolve_wire_adapter(model, custom_llm_provider).is_ok()
+}
+
+pub fn decode_request(wire: OcrWireRequest) -> Result<LiteLLMOcrRequest, Error> {
+    let document = decode_request_value(wire.document, "document")?;
+    let headers = wire
+        .extra_headers
+        .unwrap_or_default()
+        .into_iter()
+        .map(|(name, value)| {
+            let value = value
+                .as_str()
+                .ok_or_else(|| OcrRequestError::RequestField {
+                    path: format!("extra_headers.{name}"),
+                })?;
+            Ok((name, value.to_string()))
+        })
+        .collect::<Result<Vec<_>, OcrRequestError>>()?;
+    let timeout = wire
+        .timeout_seconds
+        .map(|seconds| {
+            Duration::try_from_secs_f64(seconds).map_err(|_| OcrRequestError::RequestField {
+                path: "timeout_seconds".into(),
+            })
+        })
+        .transpose()?;
+    let defaults = OcrConnection::default();
+    let request = LiteLLMOcrRequest::new(
+        wire.model,
+        document,
+        wire.custom_llm_provider.as_deref(),
+        wire.optional_params,
+    )?;
+    let connection = OcrConnection {
+        api_key: nonblank(wire.api_key),
+        api_base: nonblank(wire.api_base),
+        extra_headers: headers,
+        timeout: timeout.unwrap_or(defaults.timeout),
+    };
+    Ok(LiteLLMOcrRequest {
+        connection,
+        ..request
+    })
+}
+
+fn nonblank(value: Option<String>) -> Option<String> {
+    value
+        .map(|s| s.trim().to_string())
+        .filter(|s| !s.is_empty())
+}
+pub fn decode_request_value<T: DeserializeOwned>(
+    value: Value,
+    prefix: &str,
+) -> Result<T, OcrRequestError> {
+    serde_path_to_error::deserialize(value.into_deserializer()).map_err(|error| {
+        OcrRequestError::RequestField {
+            path: format!("{prefix}.{}", error.path()),
+        }
+    })
+}
+
+pub fn decode_response<T: DeserializeOwned>(
+    bytes: &[u8],
+    native: bool,
+) -> Result<DecodedOcrResponse<T>, OcrResponseError> {
+    let mut deserializer = serde_json::Deserializer::from_slice(bytes);
+    let data = serde_path_to_error::deserialize(&mut deserializer).map_err(|error| {
+        OcrResponseError::ResponseField {
+            path: error.path().to_string(),
+        }
+    })?;
+    deserializer
+        .end()
+        .map_err(|_| OcrResponseError::ResponseField {
+            path: "response".into(),
+        })?;
+    let native = if native {
+        Some(
+            serde_json::from_slice(bytes).map_err(|_| OcrResponseError::ResponseField {
+                path: "response".into(),
+            })?,
+        )
+    } else {
+        None
+    };
+    Ok(DecodedOcrResponse { data, native })
+}
+
+pub fn decode_pre_call_result(
+    original: OcrPreCallRequest,
+    value: Value,
+) -> Result<OcrPreCallRequest, OcrRequestError> {
+    #[derive(Deserialize)]
+    struct Changed {
+        document: OcrDocument,
+        #[serde(default)]
+        optional_params: Map<String, Value>,
+    }
+    let changed: Changed = decode_request_value(value, "guardrail")?;
+    Ok(OcrPreCallRequest {
+        document: changed.document,
+        optional_params: Value::Object(changed.optional_params),
+        ..original
+    })
+}
+
+pub fn decode_during_call_result(
+    original: OcrDuringCallRequest,
+    value: Value,
+) -> Result<OcrDuringCallRequest, OcrRequestError> {
+    #[derive(Deserialize)]
+    struct Changed {
+        body: Value,
+    }
+    let changed: Changed = decode_request_value(value, "guardrail")?;
+    Ok(OcrDuringCallRequest {
+        body: changed.body,
+        ..original
+    })
+}
diff --git a/litellm-rust/crates/core/src/providers/azure_ai/ocr/transformation.rs b/litellm-rust/crates/core/src/providers/azure_ai/ocr/transformation.rs
index d15c032f0bc..2af25a5639a 100644
--- a/litellm-rust/crates/core/src/providers/azure_ai/ocr/transformation.rs
+++ b/litellm-rust/crates/core/src/providers/azure_ai/ocr/transformation.rs
@@ -2,7 +2,7 @@ use std::collections::BTreeSet;
 
 use crate::error::{Error, json_type_name};
 use crate::ocr::transformation::{OcrAuthStrategy, OcrProviderConfig, OcrResponseHandling};
-use crate::ocr::types::{OcrRequestData, OcrResponseData};
+use crate::ocr::types::{LiteLLMOcrResponse, OcrRequestData};
 use serde_json::{Map, Value, json};
 
 use crate::providers::mistral::ocr::transformation::MISTRAL_OCR_CONFIG;
@@ -440,7 +440,7 @@ fn transform_document_intelligence_response(
     model: &str,
     response_json: Value,
     preserve_native_response: bool,
-) -> Result<OcrResponseData, Error> {
+) -> Result<LiteLLMOcrResponse, Error> {
     let response = response_json
         .as_object()
         .ok_or_else(|| Error::InvalidType {
@@ -488,7 +488,7 @@ fn transform_document_intelligence_response(
         })
         .collect();
 
-    Ok(OcrResponseData {
+    Ok(LiteLLMOcrResponse {
         usage_info: Some(json!({
             "pages_processed": pages.len(),
             "doc_size_bytes": null,
@@ -521,7 +521,7 @@ impl OcrProviderConfig for AzureAiOcrConfig {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         MISTRAL_OCR_CONFIG.transform_ocr_response(model, response_json)
     }
 
@@ -599,7 +599,7 @@ impl OcrProviderConfig for AzureDocumentIntelligenceOcrConfig {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         transform_document_intelligence_response(model, response_json, false)
     }
 
@@ -608,7 +608,7 @@ impl OcrProviderConfig for AzureDocumentIntelligenceOcrConfig {
         model: &str,
         response_json: Value,
         optional_params: &Map<String, Value>,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         transform_document_intelligence_response(
             model,
             response_json,
@@ -718,7 +718,7 @@ mod tests {
         })
     }
 
-    fn assert_native_fields_preserved(response: &OcrResponseData, operation: &Value) {
+    fn assert_native_fields_preserved(response: &LiteLLMOcrResponse, operation: &Value) {
         let analyze_result = &operation["analyzeResult"];
 
         assert_eq!(response.extra_fields["content"], analyze_result["content"]);
diff --git a/litellm-rust/crates/core/src/providers/mistral/ocr/transformation.rs b/litellm-rust/crates/core/src/providers/mistral/ocr/transformation.rs
index 11e8fe7db18..044fc587c22 100644
--- a/litellm-rust/crates/core/src/providers/mistral/ocr/transformation.rs
+++ b/litellm-rust/crates/core/src/providers/mistral/ocr/transformation.rs
@@ -1,6 +1,6 @@
 use crate::error::{Error, json_type_name};
 use crate::ocr::transformation::OcrProviderConfig;
-use crate::ocr::types::{OcrRequestData, OcrResponseData};
+use crate::ocr::types::{LiteLLMOcrResponse, OcrRequestData};
 use serde_json::{Map, Value};
 
 const SUPPORTED_OCR_PARAMS: &[&str] = &[
@@ -107,7 +107,7 @@ impl OcrProviderConfig for MistralOcrConfig {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         let response_object = response_json
             .as_object()
             .ok_or_else(|| Error::InvalidType {
@@ -128,7 +128,7 @@ impl OcrProviderConfig for MistralOcrConfig {
         let document_annotation = response_object.get("document_annotation").cloned();
         let usage_info = response_object.get("usage_info").cloned();
 
-        Ok(OcrResponseData {
+        Ok(LiteLLMOcrResponse {
             pages,
             model,
             document_annotation,
@@ -178,7 +178,10 @@ pub fn transform_ocr_request(
 }
 
 #[tracing::instrument(target = "litellm::function_trace", level = "trace", skip_all)]
-pub fn transform_ocr_response(model: &str, response_json: Value) -> Result<OcrResponseData, Error> {
+pub fn transform_ocr_response(
+    model: &str,
+    response_json: Value,
+) -> Result<LiteLLMOcrResponse, Error> {
     MISTRAL_OCR_CONFIG.transform_ocr_response(model, response_json)
 }
 
diff --git a/litellm-rust/crates/core/src/providers/reducto/ocr/transformation.rs b/litellm-rust/crates/core/src/providers/reducto/ocr/transformation.rs
index b8507541e18..f025887846f 100644
--- a/litellm-rust/crates/core/src/providers/reducto/ocr/transformation.rs
+++ b/litellm-rust/crates/core/src/providers/reducto/ocr/transformation.rs
@@ -6,7 +6,7 @@ use serde_json::{Map, Value, json};
 
 use crate::error::{Error, json_type_name};
 use crate::ocr::transformation::OcrProviderConfig;
-use crate::ocr::types::{OcrRequestData, OcrResponseData};
+use crate::ocr::types::{LiteLLMOcrResponse, OcrRequestData};
 
 pub const REDUCTO_API_BASE: &str = "https://platform.reducto.ai";
 pub const REDUCTO_API_KEY_ENV: &str = "REDUCTO_API_KEY";
@@ -283,7 +283,7 @@ fn build_pages(result: &Map<String, Value>) -> Vec<Value> {
 pub fn transform_reducto_response(
     model: &str,
     response_json: Value,
-) -> Result<OcrResponseData, Error> {
+) -> Result<LiteLLMOcrResponse, Error> {
     let response = response_json
         .as_object()
         .ok_or_else(|| Error::InvalidType {
@@ -311,7 +311,7 @@ pub fn transform_reducto_response(
         "credits": usage.get("credits").cloned().unwrap_or(Value::Null),
     }));
 
-    Ok(OcrResponseData {
+    Ok(LiteLLMOcrResponse {
         pages: build_pages(result),
         model: model.to_string(),
         document_annotation: None,
@@ -341,7 +341,7 @@ impl OcrProviderConfig for ReductoParseV3Config {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         transform_reducto_response(model, response_json)
     }
 
@@ -383,7 +383,7 @@ impl OcrProviderConfig for ReductoParseLegacyConfig {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         transform_reducto_response(model, response_json)
     }
 
diff --git a/litellm-rust/crates/core/src/providers/vertex_ai/ocr/transformation.rs b/litellm-rust/crates/core/src/providers/vertex_ai/ocr/transformation.rs
index c324de8cb45..b0e5a278d0b 100644
--- a/litellm-rust/crates/core/src/providers/vertex_ai/ocr/transformation.rs
+++ b/litellm-rust/crates/core/src/providers/vertex_ai/ocr/transformation.rs
@@ -1,6 +1,6 @@
 use crate::error::{Error, json_type_name};
 use crate::ocr::transformation::OcrProviderConfig;
-use crate::ocr::types::{OcrRequestData, OcrResponseData};
+use crate::ocr::types::{LiteLLMOcrResponse, OcrRequestData};
 use serde_json::{Map, Value, json};
 
 use crate::providers::mistral::ocr::transformation::MISTRAL_OCR_CONFIG;
@@ -226,7 +226,7 @@ impl OcrProviderConfig for VertexAiOcrConfig {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         MISTRAL_OCR_CONFIG.transform_ocr_response(model, response_json)
     }
 
@@ -301,7 +301,7 @@ impl OcrProviderConfig for VertexAiDeepSeekOcrConfig {
         &self,
         model: &str,
         response_json: Value,
-    ) -> Result<OcrResponseData, Error> {
+    ) -> Result<LiteLLMOcrResponse, Error> {
         let response = response_json
             .as_object()
             .ok_or_else(|| Error::InvalidType {
@@ -339,7 +339,7 @@ impl OcrProviderConfig for VertexAiDeepSeekOcrConfig {
             .get("usage_info")
             .cloned()
             .or_else(|| response.get("usage").cloned());
-        Ok(OcrResponseData {
+        Ok(LiteLLMOcrResponse {
             pages,
             model: object
                 .get("model")
diff --git a/litellm-rust/crates/core/src/url_utils.rs b/litellm-rust/crates/core/src/url_utils.rs
new file mode 100644
index 00000000000..982dca0dbe3
--- /dev/null
+++ b/litellm-rust/crates/core/src/url_utils.rs
@@ -0,0 +1,95 @@
+use std::marker::PhantomData;
+
+use thiserror::Error;
+use url::Url;
+
+#[derive(Debug, Error)]
+pub(crate) enum ApiUrlError {
+    #[error("invalid URL: {0}")]
+    Parse(#[from] url::ParseError),
+    #[error("URL cannot be used as a base")]
+    CannotBeBase,
+}
+
+pub(crate) struct Base;
+pub(crate) struct Complete;
+
+pub(crate) struct ApiUrl<State> {
+    url: Url,
+    state: PhantomData<State>,
+}
+
+impl ApiUrl<Base> {
+    pub(crate) fn parse(value: &str) -> Result<Self, ApiUrlError> {
+        Ok(Self {
+            url: Url::parse(value.trim())?,
+            state: PhantomData,
+        })
+    }
+
+    pub(crate) fn complete_path(
+        mut self,
+        target: &[&str],
+    ) -> Result<ApiUrl<Complete>, ApiUrlError> {
+        let existing: Vec<String> = self
+            .url
+            .path_segments()
+            .ok_or(ApiUrlError::CannotBeBase)?
+            .filter(|segment| !segment.is_empty())
+            .map(str::to_string)
+            .collect();
+        let overlap = (0..=existing.len().min(target.len()))
+            .rev()
+            .find(|&length| {
+                existing[existing.len() - length..]
+                    .iter()
+                    .map(String::as_str)
+                    .eq(target[..length].iter().copied())
+            })
+            .unwrap_or(0);
+        self.url
+            .path_segments_mut()
+            .map_err(|()| ApiUrlError::CannotBeBase)?
+            .pop_if_empty()
+            .extend(target[overlap..].iter().copied());
+        Ok(ApiUrl {
+            url: self.url,
+            state: PhantomData,
+        })
+    }
+}
+
+impl ApiUrl<Complete> {
+    pub(crate) fn into_string(self) -> String {
+        self.url.into()
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    #[test]
+    fn completion_appends_only_the_missing_path_suffix() {
+        for (base, expected) in [
+            ("https://example.test", "https://example.test/v1/ocr"),
+            ("https://example.test/v1", "https://example.test/v1/ocr"),
+            ("https://example.test/v1/ocr", "https://example.test/v1/ocr"),
+        ] {
+            let actual = ApiUrl::parse(base)
+                .and_then(|url| url.complete_path(&["v1", "ocr"]))
+                .map(|url| url.into_string())
+                .expect("url builds");
+            assert_eq!(actual, expected);
+        }
+    }
+
+    #[test]
+    fn completion_places_paths_before_queries() {
+        let actual = ApiUrl::parse("https://example.test/v1?tenant=a")
+            .and_then(|url| url.complete_path(&["v1", "ocr"]))
+            .map(|url| url.into_string())
+            .expect("url builds");
+        assert_eq!(actual, "https://example.test/v1/ocr?tenant=a");
+    }
+}
diff --git a/litellm-rust/crates/core/tests/ocr.rs b/litellm-rust/crates/core/tests/ocr.rs
new file mode 100644
index 00000000000..d1828dfb816
--- /dev/null
+++ b/litellm-rust/crates/core/tests/ocr.rs
@@ -0,0 +1,227 @@
+use std::sync::{Arc, Mutex};
+
+use serde_json::{Value, json};
+
+use super::OcrClient;
+use super::hooks::{OcrHookFuture, OcrHooks, OcrLogFuture, OcrPreCallRequest};
+use super::test_support::{MockResponse, mock_server, perform_ocr, wire_request};
+use super::wire::{OcrWireRequest, decode_request};
+use crate::call_lifecycle::{CallLifecycleContext, CallLifecycleTiming};
+
+#[test]
+fn request_boundary_selects_mistral_and_rejects_unknown_providers() {
+    let request = OcrWireRequest {
+        model: "mistral/model".into(),
+        document: json!({"type":"document_url","document_url":"https://example.com/doc.pdf"}),
+        api_key: Some("key".into()),
+        api_base: None,
+        custom_llm_provider: None,
+        extra_headers: None,
+        optional_params: json!({"extract_header":true,"unknown":42})
+            .as_object()
+            .unwrap()
+            .clone(),
+        timeout_seconds: None,
+    };
+    assert!(decode_request(request).is_ok());
+    assert!(
+        decode_request(OcrWireRequest {
+            model: "model".into(),
+            document: json!({"type":"document_url","document_url":"https://example.com/doc.pdf"}),
+            api_key: Some("key".into()),
+            api_base: None,
+            custom_llm_provider: Some("unknown".into()),
+            extra_headers: None,
+            optional_params: serde_json::Map::new(),
+            timeout_seconds: None,
+        })
+        .is_err()
+    );
+}
+
+#[tokio::test]
+async fn facade_executes_direct_mistral_once() {
+    let (base, seen, server) = mock_server(vec![MockResponse::json(json!({
+        "pages":[{"index":0,"markdown":"hello","custom":"preserved"}],
+        "usage_info":{"pages_processed":1}
+    }))])
+    .await;
+    let result = perform_ocr(wire_request(
+        "mistral/model",
+        &base,
+        json!({"extract_header":true,"unknown":"ignored"}),
+    ))
+    .await
+    .unwrap();
+    server.await.unwrap();
+    assert_eq!(result.pages[0]["markdown"], "hello");
+    assert_eq!(result.pages[0]["custom"], "preserved");
+    let requests = seen.lock().unwrap();
+    assert_eq!(requests.len(), 1);
+    assert!(requests[0].starts_with("POST /v1/ocr "));
+    assert!(
+        requests[0]
+            .to_ascii_lowercase()
+            .contains("authorization: bearer test-key\r\n")
+    );
+    let body: Value = serde_json::from_str(requests[0].split_once("\r\n\r\n").unwrap().1).unwrap();
+    assert_eq!(
+        body,
+        json!({
+            "model":"model",
+            "document":{"type":"document_url","document_url":"data:application/pdf;base64,YWJj"},
+            "extract_header":true
+        })
+    );
+}
+
+#[tokio::test]
+async fn facade_retains_native_response_when_requested() {
+    let provider_response = json!({
+        "pages":[{"index":0,"markdown":"hello"}],
+        "usage_info":{"pages_processed":1},
+        "provider_only":"preserved"
+    });
+    let (base, _, server) = mock_server(vec![MockResponse::json(provider_response.clone())]).await;
+    let response = perform_ocr(wire_request(
+        "mistral/model",
+        &base,
+        json!({"req_format":"native"}),
+    ))
+    .await
+    .unwrap();
+
+    server.await.unwrap();
+    assert_eq!(response.provider_native_response, Some(provider_response));
+}
+
+#[tokio::test]
+async fn facade_uses_the_injected_http_client() {
+    let (base, seen, server) = mock_server(vec![MockResponse::json(json!({"pages":[]}))]).await;
+    let mut default_headers = reqwest::header::HeaderMap::new();
+    default_headers.insert(
+        "x-transport-owner",
+        reqwest::header::HeaderValue::from_static("host"),
+    );
+    let provider_http = reqwest::Client::builder()
+        .default_headers(default_headers)
+        .build()
+        .unwrap();
+    OcrClient::new(provider_http)
+        .unwrap()
+        .perform(wire_request("mistral/model", &base, json!({})))
+        .await
+        .unwrap();
+    server.await.unwrap();
+    assert!(seen.lock().unwrap()[0].contains("x-transport-owner: host"));
+}
+
+struct RecordingHooks {
+    events: Arc<Mutex<Vec<&'static str>>>,
+    block: bool,
+}
+
+impl OcrHooks for RecordingHooks {
+    fn has_guardrails(&self) -> bool {
+        true
+    }
+
+    fn pre_call(&self, request: OcrPreCallRequest) -> OcrHookFuture<'_, OcrPreCallRequest> {
+        Box::pin(async move {
+            self.events.lock().unwrap().push("pre");
+            if self.block {
+                return Err(crate::Error::InvalidRequest("blocked".into()));
+            }
+            Ok(request)
+        })
+    }
+
+    fn during_call(
+        &self,
+        request: super::hooks::OcrDuringCallRequest,
+    ) -> OcrHookFuture<'_, super::hooks::OcrDuringCallRequest> {
+        Box::pin(async move {
+            self.events.lock().unwrap().push("during");
+            Ok(request)
+        })
+    }
+
+    fn success<'a>(
+        &'a self,
+        _context: &'a CallLifecycleContext,
+        _response: &'a super::LiteLLMOcrResponse,
+        _timing: &'a CallLifecycleTiming,
+    ) -> OcrLogFuture<'a> {
+        Box::pin(async move {
+            self.events.lock().unwrap().push("success");
+        })
+    }
+
+    fn failure<'a>(
+        &'a self,
+        _context: &'a CallLifecycleContext,
+        _error: &'a crate::Error,
+        _timing: &'a CallLifecycleTiming,
+    ) -> OcrLogFuture<'a> {
+        Box::pin(async move {
+            self.events.lock().unwrap().push("failure");
+        })
+    }
+}
+
+#[tokio::test]
+async fn lifecycle_orders_hooks_and_emits_one_success() {
+    let (base, seen, server) = mock_server(vec![MockResponse::json(json!({"pages":[]}))]).await;
+    let events = Arc::new(Mutex::new(Vec::new()));
+    let request = wire_request("mistral/model", &base, json!({}));
+    let request = super::LiteLLMOcrRequest {
+        hooks: Arc::new(RecordingHooks {
+            events: events.clone(),
+            block: false,
+        }),
+        ..request
+    };
+    perform_ocr(request).await.unwrap();
+    server.await.unwrap();
+    assert_eq!(*events.lock().unwrap(), ["pre", "during", "success"]);
+    assert_eq!(seen.lock().unwrap().len(), 1);
+}
+
+#[tokio::test]
+async fn lifecycle_blocking_prevents_execution_and_emits_one_failure() {
+    let events = Arc::new(Mutex::new(Vec::new()));
+    let request = wire_request("mistral/model", "http://127.0.0.1:1", json!({}));
+    let request = super::LiteLLMOcrRequest {
+        hooks: Arc::new(RecordingHooks {
+            events: events.clone(),
+            block: true,
+        }),
+        ..request
+    };
+    let error = perform_ocr(request).await.unwrap_err();
+    assert!(matches!(error, crate::Error::InvalidRequest(_)));
+    assert_eq!(*events.lock().unwrap(), ["pre", "failure"]);
+}
+
+#[tokio::test]
+async fn upstream_failure_emits_one_terminal_failure() {
+    let (base, seen, server) = mock_server(vec![MockResponse {
+        status: 500,
+        headers: vec![],
+        body: json!({"error":"failed"}),
+    }])
+    .await;
+    let events = Arc::new(Mutex::new(Vec::new()));
+    let request = wire_request("mistral/model", &base, json!({}));
+    let request = super::LiteLLMOcrRequest {
+        hooks: Arc::new(RecordingHooks {
+            events: events.clone(),
+            block: false,
+        }),
+        ..request
+    };
+    assert!(perform_ocr(request).await.is_err());
+    server.await.unwrap();
+    assert_eq!(*events.lock().unwrap(), ["pre", "during", "failure"]);
+    assert_eq!(seen.lock().unwrap().len(), 1);
+}
diff --git a/litellm-rust/crates/core/tests/ocr/support.rs b/litellm-rust/crates/core/tests/ocr/support.rs
new file mode 100644
index 00000000000..d9720019419
--- /dev/null
+++ b/litellm-rust/crates/core/tests/ocr/support.rs
@@ -0,0 +1,106 @@
+use std::sync::{Arc, Mutex};
+
+use serde_json::{Value, json};
+use tokio::io::{AsyncReadExt, AsyncWriteExt};
+use tokio::net::TcpListener;
+
+use crate::ocr::wire::{OcrWireRequest, decode_request};
+use crate::ocr::{LiteLLMOcrRequest, LiteLLMOcrResponse, OcrClient};
+
+pub(crate) fn ocr_client() -> OcrClient {
+    OcrClient::for_test(reqwest::Client::new())
+}
+
+pub(crate) async fn perform_ocr(
+    request: LiteLLMOcrRequest,
+) -> Result<LiteLLMOcrResponse, crate::Error> {
+    ocr_client().perform(request).await
+}
+
+pub(crate) fn wire_request(model: &str, base: &str, options: Value) -> LiteLLMOcrRequest {
+    decode_request(OcrWireRequest {
+        model: model.into(),
+        document: json!({"type":"document_url","document_url":"data:application/pdf;base64,YWJj"}),
+        api_key: Some("test-key".into()),
+        api_base: Some(base.into()),
+        custom_llm_provider: None,
+        extra_headers: None,
+        optional_params: options.as_object().unwrap().clone(),
+        timeout_seconds: Some(2.0),
+    })
+    .unwrap()
+}
+
+pub(crate) struct MockResponse {
+    pub status: u16,
+    pub headers: Vec<(&'static str, String)>,
+    pub body: Value,
+}
+
+impl MockResponse {
+    pub fn json(body: Value) -> Self {
+        Self {
+            status: 200,
+            headers: vec![],
+            body,
+        }
+    }
+}
+
+pub(crate) async fn mock_server(
+    responses: Vec<MockResponse>,
+) -> (String, Arc<Mutex<Vec<String>>>, tokio::task::JoinHandle<()>) {
+    let listener = TcpListener::bind("127.0.0.1:0").await.unwrap();
+    let base = format!("http://{}", listener.local_addr().unwrap());
+    let requests = Arc::new(Mutex::new(Vec::new()));
+    let seen = requests.clone();
+    let server_base = base.clone();
+    let task = tokio::spawn(async move {
+        for response in responses {
+            let (mut socket, _) = listener.accept().await.unwrap();
+            let mut bytes = Vec::new();
+            let mut buffer = [0u8; 4096];
+            let header_end = loop {
+                let n = socket.read(&mut buffer).await.unwrap();
+                assert!(n > 0);
+                bytes.extend_from_slice(&buffer[..n]);
+                if let Some(index) = bytes.windows(4).position(|s| s == b"\r\n\r\n") {
+                    break index + 4;
+                }
+            };
+            let length = String::from_utf8_lossy(&bytes[..header_end])
+                .lines()
+                .find_map(|line| {
+                    let (name, value) = line.split_once(':')?;
+                    name.eq_ignore_ascii_case("content-length")
+                        .then(|| value.trim().parse::<usize>().unwrap())
+                })
+                .unwrap_or(0);
+            while bytes.len() < header_end + length {
+                let n = socket.read(&mut buffer).await.unwrap();
+                assert!(n > 0);
+                bytes.extend_from_slice(&buffer[..n]);
+            }
+            seen.lock()
+                .unwrap()
+                .push(String::from_utf8_lossy(&bytes).into_owned());
+            let body = serde_json::to_vec(&response.body).unwrap();
+            let headers = response
+                .headers
+                .into_iter()
+                .map(|(name, value)| {
+                    format!("{name}: {}\r\n", value.replace("{base}", &server_base))
+                })
+                .collect::<String>();
+            let head = format!(
+                "HTTP/1.1 {} OK\r\nContent-Type: application/json\r\nContent-Length: {}\r\nConnection: close\r\n{}\r\n",
+                response.status,
+                body.len(),
+                headers
+            );
+            socket.write_all(head.as_bytes()).await.unwrap();
+            socket.write_all(&body).await.unwrap();
+        }
+    });
+    (base, requests, task)
+}
diff --git a/litellm-rust/crates/core/tests/workspace_crate_allowlist.rs b/litellm-rust/crates/core/tests/workspace_crate_allowlist.rs
index fc0ab2b62a3..e7739fe7312 100644
--- a/litellm-rust/crates/core/tests/workspace_crate_allowlist.rs
+++ b/litellm-rust/crates/core/tests/workspace_crate_allowlist.rs
@@ -1,6 +1,7 @@
-//! Enforcement: the litellm-rust workspace has exactly five crates.
+//! Enforcement: the litellm-rust workspace has exactly six crates.
 //!
-//! `core` (the Rust SDK), `config` (the config-loading boundary),
+//! `core` (the Rust SDK), `token-counter` (standalone input token counting),
+//! `config` (the config-loading boundary),
 //! `ai-gateway` (the HTTP/WebSocket host),
 //! `python-interop` (domain-neutral PyO3 primitives), and `python-bridge` (the
 //! PyO3 cdylib). Adding or removing a crate must be a
@@ -20,6 +21,7 @@ use std::path::{Path, PathBuf};
 /// workspace legitimately gains or loses a crate.
 const EXPECTED_MEMBERS: &[&str] = &[
     "crates/core",
+    "crates/token-counter",
     "crates/config",
     "crates/ai-gateway",
     "crates/python-interop",
@@ -29,6 +31,7 @@ const EXPECTED_MEMBERS: &[&str] = &[
 /// The crate subdirectory names that must exist under `crates/`.
 const EXPECTED_CRATE_DIRS: &[&str] = &[
     "core",
+    "token-counter",
     "config",
     "ai-gateway",
     "python-interop",
diff --git a/litellm-rust/crates/python-bridge/Cargo.toml b/litellm-rust/crates/python-bridge/Cargo.toml
index bda09a7d840..337a1e8e5ac 100644
--- a/litellm-rust/crates/python-bridge/Cargo.toml
+++ b/litellm-rust/crates/python-bridge/Cargo.toml
@@ -24,16 +24,17 @@ trace-parity = [
 futures-util.workspace = true
 tracing = { workspace = true, optional = true }
 litellm-core = { workspace = true, features = ["bedrock-auth"] }
+litellm-token-counter.workspace = true
 litellm-ai-gateway = { workspace = true, default-features = false }
 litellm-python-interop.workspace = true
 pyo3.workspace = true
 pyo3-async-runtimes.workspace = true
 serde.workspace = true
 serde_json.workspace = true
-tokio.workspace = true
+tokio = { workspace = true, features = ["sync"] }
 
 [dev-dependencies]
-criterion = "0.8.2"
+criterion.workspace = true
 tokio-tungstenite.workspace = true
 tracing.workspace = true
 
diff --git a/litellm-rust/crates/python-bridge/src/constants.rs b/litellm-rust/crates/python-bridge/src/constants.rs
new file mode 100644
index 00000000000..d5cf5749820
--- /dev/null
+++ b/litellm-rust/crates/python-bridge/src/constants.rs
@@ -0,0 +1,2 @@
+/// Concurrent token-count encodes allowed when the core count is unavailable.
+pub(crate) const TOKEN_COUNT_FALLBACK_PARALLELISM: usize = 1;
diff --git a/litellm-rust/crates/python-bridge/src/errors.rs b/litellm-rust/crates/python-bridge/src/errors.rs
index 76c298abf89..407475dedce 100644
--- a/litellm-rust/crates/python-bridge/src/errors.rs
+++ b/litellm-rust/crates/python-bridge/src/errors.rs
@@ -41,6 +41,7 @@ pub(crate) fn chat_completions_error_to_pyerr(err: Error) -> PyErr {
         | Error::InvalidRequest(_)
         | Error::InvalidType { .. }
         | Error::MissingField(_)
+        | Error::MissingApiKey { .. }
         | Error::Routing(_)
         // Nothing reached the provider, so serving it on Python cannot double
         // bill and is the only way the caller gets an answer at all.
diff --git a/litellm-rust/crates/python-bridge/src/execution.rs b/litellm-rust/crates/python-bridge/src/execution.rs
index f3648158cf6..b57197b9ddf 100644
--- a/litellm-rust/crates/python-bridge/src/execution.rs
+++ b/litellm-rust/crates/python-bridge/src/execution.rs
@@ -3,7 +3,6 @@ use std::panic::AssertUnwindSafe;
 use std::time::Duration;
 
 use futures_util::FutureExt;
-use litellm_core::error::Error;
 use litellm_python_interop::{Pythonized, panic_to_pyerr, release_gil};
 use pyo3::exceptions::PyRuntimeError;
 use pyo3::prelude::*;
@@ -11,14 +10,15 @@ use serde::Serialize;
 use tokio::runtime::{Handle, Runtime};
 use tokio::time::{self, MissedTickBehavior};
 
-pub(crate) fn run_sync<T, F>(
+pub(crate) fn run_sync<T, E, F>(
     py: Python<'_>,
     future: F,
-    map_error: fn(Error) -> PyErr,
+    map_error: fn(E) -> PyErr,
 ) -> PyResult<Py<PyAny>>
 where
     T: Serialize + Send + 'static,
-    F: Future<Output = Result<T, Error>> + Send + 'static,
+    E: Send + 'static,
+    F: Future<Output = Result<T, E>> + Send + 'static,
 {
     run_sync_on(
         py,
@@ -28,15 +28,16 @@ where
     )
 }
 
-fn run_sync_on<T, F>(
+fn run_sync_on<T, E, F>(
     py: Python<'_>,
     runtime: &Runtime,
     future: F,
-    map_error: fn(Error) -> PyErr,
+    map_error: fn(E) -> PyErr,
 ) -> PyResult<Py<PyAny>>
 where
     T: Serialize + Send + 'static,
-    F: Future<Output = Result<T, Error>> + Send + 'static,
+    E: Send + 'static,
+    F: Future<Output = Result<T, E>> + Send + 'static,
 {
     if Handle::try_current().is_ok() {
         return Err(PyRuntimeError::new_err(
@@ -49,14 +50,15 @@ where
     Pythonized(result).into_pyobject(py).map(Bound::unbind)
 }
 
-pub(crate) fn run_async<T, F>(
+pub(crate) fn run_async<T, E, F>(
     py: Python<'_>,
     future: F,
-    map_error: fn(Error) -> PyErr,
+    map_error: fn(E) -> PyErr,
 ) -> PyResult<Bound<'_, PyAny>>
 where
     T: Serialize + Send + 'static,
-    F: Future<Output = Result<T, Error>> + Send + 'static,
+    E: Send + 'static,
+    F: Future<Output = Result<T, E>> + Send + 'static,
 {
     pyo3_async_runtimes::tokio::future_into_py(py, async move {
         let result = catch_future_panic(future).await?;
@@ -65,7 +67,7 @@ where
     })
 }
 
-fn map_core_result<T>(result: Result<T, Error>, map_error: fn(Error) -> PyErr) -> PyResult<T> {
+fn map_core_result<T, E>(result: Result<T, E>, map_error: fn(E) -> PyErr) -> PyResult<T> {
     match result {
         Ok(value) => Ok(value),
         Err(error) => Err(
@@ -75,9 +77,9 @@ fn map_core_result<T>(result: Result<T, Error>, map_error: fn(Error) -> PyErr) -
     }
 }
 
-async fn catch_future_panic<T, F>(future: F) -> PyResult<Result<T, Error>>
+async fn catch_future_panic<T, E, F>(future: F) -> PyResult<Result<T, E>>
 where
-    F: Future<Output = Result<T, Error>>,
+    F: Future<Output = Result<T, E>>,
 {
     AssertUnwindSafe(future)
         .catch_unwind()
@@ -85,9 +87,9 @@ where
         .map_err(panic_to_pyerr)
 }
 
-async fn wait_for_sync_result<T, F>(future: F) -> PyResult<Result<T, Error>>
+async fn wait_for_sync_result<T, E, F>(future: F) -> PyResult<Result<T, E>>
 where
-    F: Future<Output = Result<T, Error>>,
+    F: Future<Output = Result<T, E>>,
 {
     let future = catch_future_panic(future);
     tokio::pin!(future);
@@ -114,6 +116,7 @@ mod tests {
     use std::thread;
     use std::time::Instant;
 
+    use litellm_core::error::Error;
     use pyo3::panic::PanicException;
     use pyo3::types::{PyDict, PyModule};
     use serde::Serializer;
@@ -237,7 +240,7 @@ mod tests {
 
         let error = runtime.block_on(async {
             Python::attach(|py| {
-                run_sync::<bool, _>(py, async { Ok(true) }, runtime_error)
+                run_sync::<bool, Error, _>(py, async { Ok(true) }, runtime_error)
                     .expect_err("sync route should reject a nested Tokio runtime")
             })
         });
@@ -273,7 +276,7 @@ mod tests {
     fn sync_runner_maps_a_panicked_future() {
         Python::initialize();
         Python::attach(|py| {
-            let error = run_sync::<bool, _>(
+            let error = run_sync::<bool, Error, _>(
                 py,
                 poll_fn(|_| -> Poll<Result<bool, Error>> { panic!("route future panicked") }),
                 runtime_error,
@@ -289,7 +292,7 @@ mod tests {
     fn sync_runner_maps_a_panicked_error_mapper() {
         Python::initialize();
         Python::attach(|py| {
-            let error = run_sync::<bool, _>(
+            let error = run_sync::<bool, Error, _>(
                 py,
                 async { Err(Error::InvalidRequest("invalid".to_string())) },
                 panicking_error_mapper,
diff --git a/litellm-rust/crates/python-bridge/src/lib.rs b/litellm-rust/crates/python-bridge/src/lib.rs
index 384f0be5a1b..cf0450a1b30 100644
--- a/litellm-rust/crates/python-bridge/src/lib.rs
+++ b/litellm-rust/crates/python-bridge/src/lib.rs
@@ -1,3 +1,4 @@
+mod constants;
 mod diagnostics;
 mod errors;
 mod execution;
@@ -5,6 +6,7 @@ mod execution;
 mod function_trace;
 mod marshal;
 mod routes;
+mod token_counter;
 
 use litellm_ai_gateway::io::responses_ws::ResponsesWebSocketConnection as RustResponsesWebSocketConnection;
 use pyo3::prelude::*;
@@ -71,6 +73,7 @@ mod _native {
         super::errors::register(module)?;
         super::routes::register(module)?;
         module.add_class::<super::ResponsesWebSocketConnection>()?;
+        super::token_counter::register(module)?;
         super::diagnostics::register(module)
     }
 }
@@ -106,6 +109,7 @@ mod tests {
                 "chat_completions",
                 "achat_completions",
                 "ResponsesWebSocketConnection",
+                "TokenCounter",
                 "gil_stats",
             ];
 
diff --git a/litellm-rust/crates/python-bridge/src/token_counter.rs b/litellm-rust/crates/python-bridge/src/token_counter.rs
new file mode 100644
index 00000000000..ee82c170d55
--- /dev/null
+++ b/litellm-rust/crates/python-bridge/src/token_counter.rs
@@ -0,0 +1,87 @@
+use std::num::NonZero;
+use std::sync::Arc;
+use std::thread::available_parallelism;
+
+use litellm_python_interop::release_gil;
+use litellm_token_counter::{
+    CountableRequest, Error, InputTokenCount, TokenCounter as CoreTokenCounter,
+};
+use pyo3::exceptions::{PyRuntimeError, PyValueError};
+use pyo3::prelude::*;
+use pyo3::types::PyAny;
+use tokio::sync::Semaphore;
+
+use crate::constants::TOKEN_COUNT_FALLBACK_PARALLELISM;
+use crate::errors::RustBridgeDeclined;
+use crate::execution::run_async;
+
+/// Counts the input tokens of a raw request body off the Python event loop with
+/// the GIL released. Python owns which requests get here and what to do with
+/// the count. At most one encode per core runs at a time; the rest wait in the
+/// async task, where a cancelled Python awaiter drops them before any blocking
+/// work is scheduled.
+#[pyclass(frozen)]
+struct TokenCounter {
+    inner: Arc<CoreTokenCounter>,
+    encode_slots: Arc<Semaphore>,
+}
+
+#[pymethods]
+impl TokenCounter {
+    #[new]
+    fn new(py: Python<'_>, tokenizer_json: &str) -> PyResult<Self> {
+        let inner = release_gil(py, || CoreTokenCounter::from_json(tokenizer_json))
+            .map_err(token_count_error_to_pyerr)?;
+        Ok(Self {
+            inner: Arc::new(inner),
+            encode_slots: Arc::new(Semaphore::new(encode_parallelism())),
+        })
+    }
+
+    fn acount_request<'py>(&self, py: Python<'py>, body: &[u8]) -> PyResult<Bound<'py, PyAny>> {
+        let counter = Arc::clone(&self.inner);
+        let encode_slots = Arc::clone(&self.encode_slots);
+        let body = body.to_vec();
+        run_async(
+            py,
+            async move {
+                let _slot = encode_slots
+                    .acquire_owned()
+                    .await
+                    .map_err(|error| Error::Task(error.to_string()))?;
+                tokio::task::spawn_blocking(move || count_body(&counter, &body))
+                    .await
+                    .map_err(|error| Error::Task(error.to_string()))?
+            },
+            token_count_error_to_pyerr,
+        )
+    }
+}
+
+fn encode_parallelism() -> usize {
+    available_parallelism().map_or(TOKEN_COUNT_FALLBACK_PARALLELISM, NonZero::get)
+}
+
+fn count_body(counter: &CoreTokenCounter, body: &[u8]) -> Result<InputTokenCount, Error> {
+    let request = CountableRequest::parse(body)?;
+    counter.count_request(&request)
+}
+
+fn token_count_error_to_pyerr(error: Error) -> PyErr {
+    let message = error.to_string();
+    match error {
+        Error::Load(_) => PyValueError::new_err(message),
+        Error::RequestParse(_)
+        | Error::MissingInput
+        | Error::FloatText
+        | Error::ContentBlock
+        | Error::ArrayItems
+        | Error::JsonSerialization(_)
+        | Error::JsonUtf8(_) => RustBridgeDeclined::new_err(message),
+        Error::Encode(_) | Error::Task(_) => PyRuntimeError::new_err(message),
+    }
+}
+
+pub(crate) fn register(module: &Bound<'_, PyModule>) -> PyResult<()> {
+    module.add_class::<TokenCounter>()
+}
diff --git a/litellm-rust/crates/token-counter/Cargo.toml b/litellm-rust/crates/token-counter/Cargo.toml
new file mode 100644
index 00000000000..61c9cf6e991
--- /dev/null
+++ b/litellm-rust/crates/token-counter/Cargo.toml
@@ -0,0 +1,28 @@
+[package]
+name = "litellm-token-counter"
+version = "0.1.0"
+edition.workspace = true
+license.workspace = true
+repository.workspace = true
+
+[dependencies]
+indexmap = { version = "2.14.0", features = ["serde"] }
+itoa = "1.0"
+serde.workspace = true
+serde_json.workspace = true
+thiserror.workspace = true
+tokenizers = { version = "0.23.1", default-features = false, features = ["onig"] }
+unicode-normalization-alignments = "0.1.12"
+
+[dev-dependencies]
+criterion.workspace = true
+rand.workspace = true
+rstest.workspace = true
+
+[[bench]]
+name = "token_counter"
+harness = false
+
+[[bench]]
+name = "allocations"
+harness = false
diff --git a/litellm-rust/crates/token-counter/benches/allocations.rs b/litellm-rust/crates/token-counter/benches/allocations.rs
new file mode 100644
index 00000000000..343f815749d
--- /dev/null
+++ b/litellm-rust/crates/token-counter/benches/allocations.rs
@@ -0,0 +1,128 @@
+use std::alloc::{GlobalAlloc, Layout, System};
+use std::hint::black_box;
+use std::sync::atomic::{AtomicUsize, Ordering};
+
+use litellm_token_counter::{CountableRequest, TokenCounter};
+
+struct CountingAllocator;
+
+static ALLOCATIONS: AtomicUsize = AtomicUsize::new(0);
+static BYTES: AtomicUsize = AtomicUsize::new(0);
+
+unsafe impl GlobalAlloc for CountingAllocator {
+    unsafe fn alloc(&self, layout: Layout) -> *mut u8 {
+        ALLOCATIONS.fetch_add(1, Ordering::Relaxed);
+        BYTES.fetch_add(layout.size(), Ordering::Relaxed);
+        // SAFETY: This allocator delegates the unchanged layout to `System`.
+        unsafe { System.alloc(layout) }
+    }
+
+    unsafe fn dealloc(&self, pointer: *mut u8, layout: Layout) {
+        // SAFETY: The pointer and layout came from the delegated `System` allocation.
+        unsafe { System.dealloc(pointer, layout) }
+    }
+
+    unsafe fn realloc(&self, pointer: *mut u8, layout: Layout, size: usize) -> *mut u8 {
+        ALLOCATIONS.fetch_add(1, Ordering::Relaxed);
+        BYTES.fetch_add(size, Ordering::Relaxed);
+        // SAFETY: The pointer and layout came from `System`; the new size is unchanged.
+        unsafe { System.realloc(pointer, layout, size) }
+    }
+}
+
+#[global_allocator]
+static ALLOCATOR: CountingAllocator = CountingAllocator;
+
+#[derive(Clone, Copy)]
+struct AllocationCount {
+    allocations: usize,
+    bytes: usize,
+}
+
+impl AllocationCount {
+    fn assert_max(self, label: &str, maximum: Self) {
+        eprintln!(
+            "{label}: {} allocations, {} bytes",
+            self.allocations, self.bytes
+        );
+        assert!(
+            self.allocations <= maximum.allocations,
+            "{label} allocation count exceeded {}",
+            maximum.allocations
+        );
+        assert!(
+            self.bytes <= maximum.bytes,
+            "{label} allocated bytes exceeded {}",
+            maximum.bytes
+        );
+    }
+}
+
+const TOKENIZER_JSON: &str = include_str!(concat!(
+    env!("CARGO_MANIFEST_DIR"),
+    "/../../../litellm/litellm_core_utils/tokenizers/anthropic_tokenizer.json"
+));
+const OBJECT_BODY: &[u8] = br#"{"model":"claude-sonnet-4-5","input":{"text":"caf\u00e9","n":3,"ok":true,"list":[1,"a",{"z":[]}]}}"#;
+const INTEGER_BODY: &[u8] = br#"{"input":[-9223372036854775808,0,18446744073709551615]}"#;
+
+fn measure(operation: impl FnOnce()) -> AllocationCount {
+    ALLOCATIONS.store(0, Ordering::Relaxed);
+    BYTES.store(0, Ordering::Relaxed);
+    operation();
+    AllocationCount {
+        allocations: ALLOCATIONS.load(Ordering::Relaxed),
+        bytes: BYTES.load(Ordering::Relaxed),
+    }
+}
+
+fn main() {
+    measure(|| {
+        black_box(CountableRequest::parse(OBJECT_BODY).expect("object request parses"));
+    })
+    .assert_max(
+        "parse object request",
+        AllocationCount {
+            allocations: 16,
+            bytes: 1_900,
+        },
+    );
+
+    let counter = TokenCounter::from_json(TOKENIZER_JSON).expect("tokenizer loads");
+    let object = CountableRequest::parse(OBJECT_BODY).expect("object request parses");
+    counter
+        .count_request(&object)
+        .expect("object warmup succeeds");
+    measure(|| {
+        black_box(
+            counter
+                .count_request(black_box(&object))
+                .expect("object counts"),
+        );
+    })
+    .assert_max(
+        "count object request",
+        AllocationCount {
+            allocations: 74,
+            bytes: 2_200,
+        },
+    );
+
+    let integers = CountableRequest::parse(INTEGER_BODY).expect("integer request parses");
+    counter
+        .count_request(&integers)
+        .expect("integer warmup succeeds");
+    measure(|| {
+        black_box(
+            counter
+                .count_request(black_box(&integers))
+                .expect("integers count"),
+        );
+    })
+    .assert_max(
+        "count integer list",
+        AllocationCount {
+            allocations: 26,
+            bytes: 1_050,
+        },
+    );
+}
diff --git a/litellm-rust/crates/token-counter/benches/token_counter.rs b/litellm-rust/crates/token-counter/benches/token_counter.rs
new file mode 100644
index 00000000000..a7c3177b88a
--- /dev/null
+++ b/litellm-rust/crates/token-counter/benches/token_counter.rs
@@ -0,0 +1,100 @@
+use std::hint::black_box;
+use std::time::Duration;
+
+use criterion::{BenchmarkId, Criterion, Throughput, criterion_group, criterion_main};
+use litellm_token_counter::TokenCounter;
+use tokenizers::Tokenizer;
+
+const TOKENIZER_JSON: &str = include_str!(concat!(
+    env!("CARGO_MANIFEST_DIR"),
+    "/../../../litellm/litellm_core_utils/tokenizers/anthropic_tokenizer.json"
+));
+const FULL_CONTEXT_TOKENS: usize = 1_000_000;
+const LARGE_PROMPT_UNIT: &str = "The quick brown fox jumps over the lazy dog. 0123456789\n";
+
+fn full_context_input(tokenizer: &Tokenizer) -> String {
+    let unit_tokens = tokenizer
+        .encode_fast(LARGE_PROMPT_UNIT, false)
+        .expect("reference tokenizer should encode")
+        .len();
+    let input = LARGE_PROMPT_UNIT.repeat(FULL_CONTEXT_TOKENS.div_ceil(unit_tokens));
+    let actual_tokens = tokenizer
+        .encode_fast(input.as_str(), true)
+        .expect("reference tokenizer should encode")
+        .len();
+    assert!((FULL_CONTEXT_TOKENS..FULL_CONTEXT_TOKENS + unit_tokens).contains(&actual_tokens));
+    input
+}
+
+fn inputs(tokenizer: &Tokenizer) -> Vec<(&'static str, String)> {
+    vec![
+        (
+            "ascii_chat",
+            "User: Summarize the benefits of statistical benchmarking.\nAssistant:".repeat(8),
+        ),
+        (
+            "unicode_nfkc",
+            "Ａ quick café résumé: مرحبا 世界 🙂 fi Ⅳ.\n".repeat(16),
+        ),
+        ("large_prompt", LARGE_PROMPT_UNIT.repeat(256)),
+        ("full_context_1m_tokens", full_context_input(tokenizer)),
+    ]
+}
+
+fn token_counter(c: &mut Criterion) {
+    let counter = TokenCounter::from_json(TOKENIZER_JSON).expect("token counter should load");
+    let tokenizer = TOKENIZER_JSON
+        .parse::<Tokenizer>()
+        .expect("reference tokenizer should load");
+    let mut group = c.benchmark_group("anthropic_token_counter");
+
+    for (name, input) in inputs(&tokenizer) {
+        let expected = tokenizer
+            .encode_fast(input.as_str(), true)
+            .expect("reference tokenizer should encode")
+            .len();
+        let actual = counter
+            .count_text(input.as_str())
+            .expect("benchmark path should count");
+        assert_eq!(
+            actual, expected,
+            "benchmark paths should produce the same count"
+        );
+        group.throughput(Throughput::Bytes(input.len() as u64));
+        group.bench_with_input(
+            BenchmarkId::new("byte_level_fast_path", name),
+            &input,
+            |b, input| {
+                b.iter(|| {
+                    counter
+                        .count_text(black_box(input.as_str()))
+                        .expect("fast path should count")
+                })
+            },
+        );
+        group.bench_with_input(
+            BenchmarkId::new("full_encoder", name),
+            &input,
+            |b, input| {
+                b.iter(|| {
+                    tokenizer
+                        .encode_fast(black_box(input.as_str()), true)
+                        .expect("reference tokenizer should encode")
+                        .len()
+                })
+            },
+        );
+    }
+
+    group.finish();
+}
+
+criterion_group! {
+    name = benches;
+    config = Criterion::default()
+        .sample_size(20)
+        .warm_up_time(Duration::from_secs(1))
+        .measurement_time(Duration::from_secs(4));
+    targets = token_counter
+}
+criterion_main!(benches);
diff --git a/litellm-rust/crates/token-counter/src/byte_level.rs b/litellm-rust/crates/token-counter/src/byte_level.rs
new file mode 100644
index 00000000000..2b435eb39bb
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/byte_level.rs
@@ -0,0 +1,650 @@
+//! Exact token counting for a supported tokenizer configuration: optional
+//! NFKC normalization, `ByteLevel` pre-tokenization with the GPT-2 split regex,
+//! and no post-processing. A scanner reproduces the regex's piece boundaries
+//! and hands each piece to the tokenizer's model. Unsupported configurations
+//! and added-token inputs fall back to the full encoder.
+
+use std::borrow::Cow;
+use std::iter;
+
+use tokenizers::normalizers::NormalizerWrapper;
+use tokenizers::pre_tokenizers::PreTokenizerWrapper;
+use tokenizers::{Model, Tokenizer};
+use unicode_normalization_alignments::{IsNormalized, UnicodeNormalization, is_nfkc_quick};
+
+use super::unicode_classes::UnicodeClasses;
+
+const CONTRACTIONS: [&str; 7] = ["'s", "'t", "'re", "'ve", "'m", "'ll", "'d"];
+
+pub(super) struct ByteLevelCounter {
+    nfkc: bool,
+    normalized_added_tokens: Vec<String>,
+    unicode_classes: &'static UnicodeClasses,
+}
+
+impl ByteLevelCounter {
+    pub(super) fn detect(tokenizer: &Tokenizer) -> Option<Self> {
+        let nfkc = match tokenizer.get_normalizer() {
+            None => false,
+            Some(NormalizerWrapper::NFKC(_)) => true,
+            Some(_) => return None,
+        };
+        let Some(PreTokenizerWrapper::ByteLevel(byte_level)) = tokenizer.get_pre_tokenizer() else {
+            return None;
+        };
+        let plain = !byte_level.add_prefix_space
+            && byte_level.use_regex
+            && tokenizer.get_post_processor().is_none()
+            && tokenizer.get_truncation().is_none()
+            && tokenizer.get_padding().is_none();
+        if !plain {
+            return None;
+        }
+        let vocabulary = tokenizer.get_added_vocabulary();
+        let normalized_added_tokens = vocabulary
+            .get_vocab()
+            .iter()
+            .filter_map(|(original, id)| {
+                vocabulary
+                    .simple_id_to_token(*id)
+                    .filter(|normalized| normalized != original)
+            })
+            .collect();
+        Some(Self {
+            nfkc,
+            normalized_added_tokens,
+            unicode_classes: UnicodeClasses::get()?,
+        })
+    }
+
+    /// `None` when the text contains an added token or the model rejects a
+    /// piece; the caller then runs the full encoder.
+    pub(super) fn count(&self, tokenizer: &Tokenizer, text: &str) -> Option<usize> {
+        let normalized = self.normalize(text);
+        let added_tokens = tokenizer.get_added_vocabulary().get_vocab();
+        if added_tokens
+            .keys()
+            .chain(self.normalized_added_tokens.iter())
+            .any(|token| text.contains(token.as_str()) || normalized.contains(token.as_str()))
+        {
+            return None;
+        }
+        let model = tokenizer.get_model();
+        let mapped: String = normalized.bytes().map(byte_char).collect();
+        pieces(&normalized, self.unicode_classes)
+            .try_fold((0, 0), |(start, total), piece| {
+                let end = start + mapped_len(piece);
+                let tokens = model.tokenize(&mapped[start..end]).ok()?;
+                Some((end, total + tokens.len()))
+            })
+            .map(|(_, total)| total)
+    }
+
+    /// Same crate and Unicode tables as `NormalizedString::nfkc`, so the
+    /// result is what the full encoder would have tokenized.
+    fn normalize<'a>(&self, text: &'a str) -> Cow<'a, str> {
+        if !self.nfkc || text.is_ascii() || is_nfkc_quick(text.chars()) == IsNormalized::Yes {
+            return Cow::Borrowed(text);
+        }
+        Cow::Owned(text.nfkc().map(|(character, _)| character).collect())
+    }
+}
+
+/// GPT-2 `bytes_to_unicode`: printable Latin-1 bytes map to themselves, the
+/// rest to U+0100 onwards in byte order.
+fn byte_char(byte: u8) -> char {
+    let code = match byte {
+        0x21..=0x7E | 0xA1..=0xAC | 0xAE..=0xFF => u32::from(byte),
+        0x00..=0x20 => 0x100 + u32::from(byte),
+        0x7F..=0xA0 => 0x121 + u32::from(byte - 0x7F),
+        0xAD => 0x143,
+    };
+    char::from_u32(code).unwrap_or(char::REPLACEMENT_CHARACTER)
+}
+
+fn mapped_len(piece: &str) -> usize {
+    piece.len()
+        + piece
+            .bytes()
+            .filter(|byte| !byte.is_ascii_graphic())
+            .count()
+}
+
+#[derive(Clone, Copy, Debug, PartialEq, Eq)]
+enum Class {
+    Letter,
+    Number,
+    Space,
+    Other,
+}
+
+fn class(character: char, unicode_classes: &UnicodeClasses) -> Class {
+    match character {
+        'A'..='Z' | 'a'..='z' => Class::Letter,
+        '0'..='9' => Class::Number,
+        '\t'..='\r' | ' ' => Class::Space,
+        _ if character.is_ascii() => Class::Other,
+        _ if unicode_classes.is_letter(character) => Class::Letter,
+        _ if unicode_classes.is_number(character) => Class::Number,
+        _ if unicode_classes.is_space(character) => Class::Space,
+        _ => Class::Other,
+    }
+}
+
+/// The regex matches every character, so the pieces tile the text.
+fn pieces<'a>(
+    text: &'a str,
+    unicode_classes: &'static UnicodeClasses,
+) -> impl Iterator<Item = &'a str> {
+    iter::successors(split_piece(text, unicode_classes), move |(_, rest)| {
+        split_piece(rest, unicode_classes)
+    })
+    .map(|(piece, _)| piece)
+}
+
+fn split_piece<'a>(text: &'a str, unicode_classes: &UnicodeClasses) -> Option<(&'a str, &'a str)> {
+    let first = text.chars().next()?;
+    Some(text.split_at(piece_len(text, first, unicode_classes)))
+}
+
+fn piece_len(text: &str, first: char, unicode_classes: &UnicodeClasses) -> usize {
+    if let Some(contraction) = CONTRACTIONS.iter().find(|word| text.starts_with(**word)) {
+        return contraction.len();
+    }
+    let first_class = class(first, unicode_classes);
+    if first_class != Class::Space {
+        return run_len(text, first_class, unicode_classes);
+    }
+    if first != ' ' {
+        return space_run_len(text, unicode_classes);
+    }
+    let after_space = &text[1..];
+    match after_space
+        .chars()
+        .next()
+        .map(|character| class(character, unicode_classes))
+    {
+        None | Some(Class::Space) => space_run_len(text, unicode_classes),
+        Some(run_class) => 1 + run_len(after_space, run_class, unicode_classes),
+    }
+}
+
+fn run_len(text: &str, run_class: Class, unicode_classes: &UnicodeClasses) -> usize {
+    text.char_indices()
+        .find(|(_, character)| class(*character, unicode_classes) != run_class)
+        .map_or(text.len(), |(index, _)| index)
+}
+
+/// `\s+(?!\S)|\s+`: whitespace followed by a non-space leaves its last
+/// character to start the next piece (` ?` on the following alternatives).
+fn space_run_len(text: &str, unicode_classes: &UnicodeClasses) -> usize {
+    let run = run_len(text, Class::Space, unicode_classes);
+    if run == text.len() {
+        return run;
+    }
+    let last = text[..run].chars().next_back().map_or(0, char::len_utf8);
+    match run - last {
+        0 => run,
+        shorter => shorter,
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use rand::rngs::StdRng;
+    use rand::seq::SliceRandom;
+    use rand::{Rng, SeedableRng};
+    use rstest::{fixture, rstest};
+    use tokenizers::normalizers::NFKC;
+    use tokenizers::pre_tokenizers::byte_level::ByteLevel;
+    use tokenizers::utils::SysRegex;
+    use tokenizers::{
+        NormalizedString, Normalizer, OffsetReferential, OffsetType, PreTokenizedString,
+        PreTokenizer,
+    };
+
+    use super::*;
+
+    #[fixture]
+    fn anthropic_tokenizer() -> Tokenizer {
+        let path = concat!(
+            env!("CARGO_MANIFEST_DIR"),
+            "/../../../litellm/litellm_core_utils/tokenizers/anthropic_tokenizer.json"
+        );
+        std::fs::read_to_string(path)
+            .expect("anthropic tokenizer json is in the repo")
+            .parse()
+            .expect("anthropic tokenizer loads")
+    }
+
+    fn reference_count(tokenizer: &Tokenizer, text: &str) -> usize {
+        tokenizer.encode_fast(text, true).expect("encode").len()
+    }
+
+    fn byte_level_counter(nfkc: bool) -> ByteLevelCounter {
+        ByteLevelCounter {
+            nfkc,
+            normalized_added_tokens: Vec::new(),
+            unicode_classes: UnicodeClasses::get().expect("Oniguruma exposes Unicode classes"),
+        }
+    }
+
+    const ALPHABET: &[&str] = &[
+        "a",
+        "Z",
+        "e",
+        "s",
+        "t",
+        "d",
+        "m",
+        "'",
+        "'s",
+        "'re",
+        "'ll",
+        "'S",
+        "0",
+        "9",
+        " ",
+        "  ",
+        "\t",
+        "\n",
+        "\r\n",
+        "\u{b}",
+        ".",
+        ",",
+        "!",
+        "-",
+        "(",
+        "\"",
+        "\u{a0}",
+        "\u{85}",
+        "\u{2028}",
+        "\u{3000}",
+        "\u{200b}",
+        "\u{200d}",
+        "é",
+        "e\u{301}",
+        "ß",
+        "漢",
+        "字",
+        "ع",
+        "३",
+        "½",
+        "Ⅳ",
+        "🙂",
+        "👍🏽",
+        "Ａ",
+        "fi",
+        "㍿",
+        "㋿",
+        "ꟲ",
+        "𐞁",
+        "a\u{30a}",
+        "\u{1e0b}\u{323}",
+        "<",
+        ">",
+        "EOT",
+        "<EOT>",
+        "<META_START>",
+    ];
+
+    fn random_text(rng: &mut StdRng) -> String {
+        let pieces = rng.gen_range(0..40);
+        (0..pieces)
+            .map(|_| *ALPHABET.choose(rng).expect("alphabet is not empty"))
+            .collect()
+    }
+
+    #[rstest]
+    #[case::plain_text("Hello, how are you today?", true)]
+    #[case::added_token("stop <EOT> here", false)]
+    #[case::normalized_added_token("stop ＜ＥＯＴ＞ here", false)]
+    fn anthropic_tokenizer_takes_the_fast_path(
+        anthropic_tokenizer: Tokenizer,
+        #[case] text: &str,
+        #[case] supported: bool,
+    ) {
+        let fast =
+            ByteLevelCounter::detect(&anthropic_tokenizer).expect("anthropic shape is supported");
+        assert!(fast.nfkc);
+        let count = fast.count(&anthropic_tokenizer, text);
+        if supported {
+            assert_eq!(count, Some(reference_count(&anthropic_tokenizer, text)));
+        } else {
+            assert_eq!(count, None);
+        }
+    }
+
+    #[rstest]
+    fn counts_match_the_full_encoder(anthropic_tokenizer: Tokenizer) {
+        let fast = ByteLevelCounter::detect(&anthropic_tokenizer).expect("supported");
+        let mut rng = StdRng::seed_from_u64(2026);
+        for _ in 0..4000 {
+            let text = random_text(&mut rng).replace('<', "(");
+            let expected = reference_count(&anthropic_tokenizer, &text);
+            assert_eq!(
+                fast.count(&anthropic_tokenizer, &text),
+                Some(expected),
+                "text {text:?}"
+            );
+        }
+    }
+
+    #[rstest]
+    fn nfkc_matches_the_tokenizer_normalizer_for_every_scalar_value() {
+        let fast = byte_level_counter(true);
+        let mut text = String::new();
+        for character in (0..=0x10FFFFu32).filter_map(char::from_u32) {
+            text.clear();
+            text.push(character);
+            let mut expected = NormalizedString::from(text.as_str());
+            NFKC.normalize(&mut expected).expect("nfkc");
+            assert_eq!(
+                fast.normalize(&text),
+                expected.get(),
+                "U+{:04X}",
+                u32::from(character)
+            );
+        }
+    }
+
+    #[rstest]
+    fn nfkc_matches_the_tokenizer_normalizer_on_random_texts() {
+        let fast = byte_level_counter(true);
+        let mut rng = StdRng::seed_from_u64(11);
+        for _ in 0..4000 {
+            let text = random_text(&mut rng);
+            let mut expected = NormalizedString::from(text.as_str());
+            NFKC.normalize(&mut expected).expect("nfkc");
+            assert_eq!(fast.normalize(&text), expected.get(), "text {text:?}");
+        }
+    }
+
+    #[rstest]
+    fn pieces_match_the_byte_level_pre_tokenizer() {
+        let byte_level = ByteLevel::new(false, true, true);
+        let mut rng = StdRng::seed_from_u64(7);
+        for _ in 0..4000 {
+            let text = byte_level_counter(true)
+                .normalize(&random_text(&mut rng))
+                .into_owned();
+            let mut pre_tokenized = PreTokenizedString::from(text.as_str());
+            byte_level
+                .pre_tokenize(&mut pre_tokenized)
+                .expect("pre-tokenize");
+            let expected: Vec<(String, (usize, usize))> = pre_tokenized
+                .get_splits(OffsetReferential::Original, OffsetType::Byte)
+                .into_iter()
+                .map(|(mapped, offsets, _)| (mapped.to_string(), offsets))
+                .collect();
+            let actual: Vec<(String, (usize, usize))> = pieces(
+                &text,
+                UnicodeClasses::get().expect("Oniguruma exposes Unicode classes"),
+            )
+            .map(|piece| {
+                let start = piece.as_ptr() as usize - text.as_ptr() as usize;
+                let mapped: String = piece.bytes().map(byte_char).collect();
+                (mapped, (start, start + piece.len()))
+            })
+            .collect();
+            assert_eq!(actual, expected, "text {text:?}");
+        }
+    }
+
+    #[rstest]
+    fn byte_chars_match_the_byte_level_alphabet() {
+        let byte_level = ByteLevel::new(false, false, false);
+        let characters: Vec<char> = (0..=0x10FFFFu32).filter_map(char::from_u32).collect();
+        for chunk in characters.chunks(1024) {
+            let text: String = chunk.iter().collect();
+            let mut pre_tokenized = PreTokenizedString::from(text.as_str());
+            byte_level
+                .pre_tokenize(&mut pre_tokenized)
+                .expect("pre-tokenize");
+            let expected: String = pre_tokenized
+                .get_splits(OffsetReferential::Original, OffsetType::Byte)
+                .into_iter()
+                .map(|(mapped, _, _)| mapped)
+                .collect();
+            let actual: String = text.bytes().map(byte_char).collect();
+            assert_eq!(actual.len(), mapped_len(&text));
+            assert_eq!(
+                actual,
+                expected,
+                "chunk starting at U+{:04X}",
+                u32::from(chunk[0])
+            );
+        }
+    }
+
+    #[rstest]
+    fn classes_match_oniguruma() {
+        let unicode_classes = UnicodeClasses::get().expect("Oniguruma exposes Unicode classes");
+        let letter = SysRegex::new(r"\p{L}").expect("regex");
+        let number = SysRegex::new(r"\p{N}").expect("regex");
+        let space = SysRegex::new(r"\s").expect("regex");
+        let whole =
+            |regex: &SysRegex, text: &str| regex.find_iter(text).next() == Some((0, text.len()));
+        let mut text = String::new();
+        for character in (0..=0x10FFFFu32).filter_map(char::from_u32) {
+            text.clear();
+            text.push(character);
+            let expected = if whole(&letter, &text) {
+                Class::Letter
+            } else if whole(&number, &text) {
+                Class::Number
+            } else if whole(&space, &text) {
+                Class::Space
+            } else {
+                Class::Other
+            };
+            assert_eq!(
+                class(character, unicode_classes),
+                expected,
+                "U+{:04X}",
+                u32::from(character)
+            );
+        }
+    }
+
+    #[rstest]
+    #[case("prefix")]
+    #[case("regex")]
+    #[case("normalizer")]
+    #[case("no_pre_tokenizer")]
+    #[case("other_pre_tokenizer")]
+    #[case("post_processor")]
+    #[case("truncation")]
+    #[case("padding")]
+    fn other_tokenizer_shapes_are_declined(
+        mut anthropic_tokenizer: Tokenizer,
+        #[case] shape: &str,
+    ) {
+        use tokenizers::{PaddingParams, PaddingStrategy, TruncationParams};
+        match shape {
+            "prefix" => {
+                anthropic_tokenizer.with_pre_tokenizer(Some(ByteLevel::new(true, true, true)));
+            }
+            "regex" => {
+                anthropic_tokenizer.with_pre_tokenizer(Some(ByteLevel::new(false, true, false)));
+            }
+            "normalizer" => {
+                anthropic_tokenizer
+                    .with_normalizer(Some(tokenizers::normalizers::Lowercase))
+                    .expect("normalizer");
+            }
+            "no_pre_tokenizer" => {
+                anthropic_tokenizer.with_pre_tokenizer(None::<PreTokenizerWrapper>);
+            }
+            "other_pre_tokenizer" => {
+                anthropic_tokenizer
+                    .with_pre_tokenizer(Some(tokenizers::pre_tokenizers::whitespace::Whitespace));
+            }
+            "post_processor" => {
+                anthropic_tokenizer.with_post_processor(Some(ByteLevel::default()));
+            }
+            "truncation" => {
+                anthropic_tokenizer
+                    .with_truncation(Some(TruncationParams {
+                        max_length: 2,
+                        ..Default::default()
+                    }))
+                    .expect("truncation");
+            }
+            "padding" => {
+                anthropic_tokenizer.with_padding(Some(PaddingParams {
+                    strategy: PaddingStrategy::Fixed(32),
+                    ..Default::default()
+                }));
+            }
+            _ => unreachable!(),
+        }
+        assert!(ByteLevelCounter::detect(&anthropic_tokenizer).is_none());
+        let counter = crate::TokenCounter::from_json(
+            &anthropic_tokenizer.to_string(false).expect("serialize"),
+        )
+        .expect("load");
+        for text in ["", "Hello WORLD!  ＡＢ fi Ⅳ", "<EOT> stop"] {
+            assert_eq!(
+                counter.count_text(text).expect("count"),
+                reference_count(&anthropic_tokenizer, text)
+            );
+        }
+    }
+
+    #[rstest]
+    #[case(false)]
+    #[case(true)]
+    fn arbitrary_unicode_and_long_inputs_use_fast_path(
+        mut anthropic_tokenizer: Tokenizer,
+        #[case] nfkc: bool,
+    ) {
+        if !nfkc {
+            anthropic_tokenizer
+                .with_normalizer(None::<NormalizerWrapper>)
+                .expect("normalizer");
+        }
+        let fast = ByteLevelCounter::detect(&anthropic_tokenizer).expect("supported");
+        let mut rng = StdRng::seed_from_u64(314159);
+        for _ in 0..1000 {
+            let text: String = (0..64)
+                .filter_map(|_| char::from_u32(rng.gen_range(0..=0x10ffff)))
+                .collect();
+            assert_eq!(
+                fast.count(&anthropic_tokenizer, &text),
+                Some(reference_count(&anthropic_tokenizer, &text)),
+                "text {text:?}"
+            );
+        }
+        for text in [
+            "",
+            "'s't're've'm'll'd'S'RE",
+            "  a \t\r\n b\u{85}\u{a0}c  ",
+            "\0é漢🙂",
+            "a\u{30a}\u{301}",
+            "ＡfiⅣ",
+        ] {
+            let text = text.repeat(2048);
+            assert_eq!(
+                fast.count(&anthropic_tokenizer, &text),
+                Some(reference_count(&anthropic_tokenizer, &text))
+            );
+        }
+    }
+
+    #[rstest]
+    #[case(false, false, false, false)]
+    #[case(true, false, false, false)]
+    #[case(false, true, false, false)]
+    #[case(false, false, true, false)]
+    #[case(false, false, false, true)]
+    fn added_token_options_fall_back(
+        mut anthropic_tokenizer: Tokenizer,
+        #[case] special: bool,
+        #[case] single_word: bool,
+        #[case] lstrip: bool,
+        #[case] rstrip: bool,
+    ) {
+        anthropic_tokenizer
+            .add_tokens([tokenizers::AddedToken::from("custom token", special)
+                .single_word(single_word)
+                .lstrip(lstrip)
+                .rstrip(rstrip)])
+            .expect("add token");
+        let fast = ByteLevelCounter::detect(&anthropic_tokenizer).expect("supported");
+        let counter = crate::TokenCounter::from_json(
+            &anthropic_tokenizer.to_string(false).expect("serialize"),
+        )
+        .expect("load");
+        for text in [
+            "custom token",
+            "a custom token b",
+            "acustom tokenb",
+            "  custom token  ",
+        ] {
+            assert_eq!(fast.count(&anthropic_tokenizer, text), None);
+            assert_eq!(
+                counter.count_text(text).expect("count"),
+                reference_count(&anthropic_tokenizer, text)
+            );
+        }
+    }
+
+    #[test]
+    fn model_errors_reach_public_caller() {
+        let mut tokenizer = Tokenizer::new(tokenizers::models::wordpiece::WordPiece::default());
+        tokenizer.with_pre_tokenizer(Some(ByteLevel::new(false, true, true)));
+        let fast = ByteLevelCounter::detect(&tokenizer).expect("supported");
+        assert_eq!(fast.count(&tokenizer, "hello"), None);
+        assert!(tokenizer.encode_fast("hello", true).is_err());
+        let counter =
+            crate::TokenCounter::from_json(&tokenizer.to_string(false).expect("serialize"))
+                .expect("load");
+        assert!(matches!(
+            counter.count_text("hello"),
+            Err(crate::Error::Encode(_))
+        ));
+    }
+
+    #[rstest]
+    fn shared_counter_matches_encoder_across_threads(anthropic_tokenizer: Tokenizer) {
+        let counter = crate::TokenCounter::from_json(
+            &anthropic_tokenizer.to_string(false).expect("serialize"),
+        )
+        .expect("load");
+        let inputs = [
+            "hello world",
+            "ＡＢ fi\n漢字🙂",
+            " <EOT> stop",
+            "\t  're \r\n",
+        ];
+        let expected = inputs.map(|text| reference_count(&anthropic_tokenizer, text));
+        std::thread::scope(|scope| {
+            for _ in 0..8 {
+                let counter = &counter;
+                scope.spawn(move || {
+                    for _ in 0..100 {
+                        for (text, count) in inputs.iter().zip(expected) {
+                            assert_eq!(counter.count_text(text).expect("count"), count);
+                        }
+                    }
+                });
+            }
+        });
+    }
+
+    #[rstest]
+    fn normalized_added_token_spelling_declines_fast_path(mut anthropic_tokenizer: Tokenizer) {
+        anthropic_tokenizer
+            .add_tokens([tokenizers::AddedToken::from("ＡＢＣＤ　ＥＦＧＨ", false)])
+            .expect("add token");
+        let fast = ByteLevelCounter::detect(&anthropic_tokenizer).expect("supported");
+        assert_eq!(reference_count(&anthropic_tokenizer, "ABCD EFGH"), 1);
+        assert_eq!(fast.count(&anthropic_tokenizer, "ABCD EFGH"), None);
+        let counter = crate::TokenCounter::from_json(
+            &anthropic_tokenizer.to_string(false).expect("serialize"),
+        )
+        .expect("load");
+        assert_eq!(counter.count_text("ABCD EFGH").expect("count"), 1);
+    }
+}
diff --git a/litellm-rust/crates/token-counter/src/counter.rs b/litellm-rust/crates/token-counter/src/counter.rs
new file mode 100644
index 00000000000..a3943515a64
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/counter.rs
@@ -0,0 +1,194 @@
+use serde::Serialize;
+
+use crate::Error;
+use crate::byte_level::ByteLevelCounter;
+use crate::python_json;
+use crate::tools::format_function_definitions;
+use crate::types::{
+    ContentBlock, ContentItem, CountableRequest, Message, MessageContent, TextValue, ToolChoice,
+    ToolDefinition,
+};
+
+const TOKENS_PER_MESSAGE: usize = 3;
+const TOKENS_PER_NAME: usize = 1;
+const REPLY_PRIMING_TOKENS: usize = 3;
+const TOOL_DEFINITIONS_TOKENS: usize = 9;
+const TOOLS_WITH_SYSTEM_MESSAGE_DISCOUNT: usize = 4;
+const TOOL_CHOICE_NONE_TOKENS: usize = 1;
+const NAMED_TOOL_CHOICE_TOKENS: usize = 7;
+
+#[derive(Clone, Debug, PartialEq, Eq, Serialize)]
+pub struct InputTokenCount {
+    pub model: Option<String>,
+    pub input_tokens: usize,
+}
+
+/// A loaded HuggingFace tokenizer plus the message accounting Python applies on
+/// top of it. Encoding is CPU-bound and synchronous; hosts run it off their
+/// event loop.
+pub struct TokenCounter {
+    tokenizer: tokenizers::Tokenizer,
+    byte_level: Option<ByteLevelCounter>,
+}
+
+impl TokenCounter {
+    /// Load a HuggingFace `tokenizer.json` document. The host reads the file.
+    pub fn from_json(tokenizer_json: &str) -> Result<Self, Error> {
+        let tokenizer = tokenizer_json
+            .parse::<tokenizers::Tokenizer>()
+            .map_err(Error::Load)?;
+        let byte_level = ByteLevelCounter::detect(&tokenizer);
+        Ok(Self {
+            tokenizer,
+            byte_level,
+        })
+    }
+
+    pub fn count_text(&self, text: &str) -> Result<usize, Error> {
+        if let Some(count) = self
+            .byte_level
+            .as_ref()
+            .and_then(|counter| counter.count(&self.tokenizer, text))
+        {
+            return Ok(count);
+        }
+        self.tokenizer
+            .encode_fast(text, true)
+            .map(|encoding| encoding.len())
+            .map_err(Error::Encode)
+    }
+
+    /// Mirrors the host's key precedence: `messages`, then `prompt`, then
+    /// `input`, then `query` plus `documents`.
+    pub fn count_request(&self, request: &CountableRequest) -> Result<InputTokenCount, Error> {
+        let input_tokens = if let Some(messages) = &request.messages {
+            self.count_messages(request, messages)?
+        } else if let Some(prompt) = &request.prompt {
+            self.count_text_value(prompt)?
+        } else if let Some(input) = &request.input {
+            self.count_text_value(input)?
+        } else if request.query.is_some() || request.documents.is_some() {
+            self.count_optional_text_value(request.query.as_ref())?
+                + self.count_optional_text_value(request.documents.as_ref())?
+        } else {
+            return Err(Error::MissingInput);
+        };
+        Ok(InputTokenCount {
+            model: request.model.clone(),
+            input_tokens,
+        })
+    }
+
+    fn count_messages(
+        &self,
+        request: &CountableRequest,
+        messages: &[Message],
+    ) -> Result<usize, Error> {
+        let message_tokens = messages
+            .iter()
+            .map(|message| self.count_message(message))
+            .sum::<Result<usize, _>>()?;
+        let includes_system_message = messages
+            .iter()
+            .any(|message| message.role.as_deref() == Some("system"));
+        let extra_tokens = self.count_extra(
+            request.tools.as_deref().unwrap_or_default(),
+            request.tool_choice.as_ref(),
+            includes_system_message,
+        )?;
+        Ok(message_tokens + extra_tokens)
+    }
+
+    fn count_optional_text_value(&self, value: Option<&TextValue>) -> Result<usize, Error> {
+        value.map_or(Ok(0), |value| self.count_text_value(value))
+    }
+
+    /// `str()` for scalars, `json.dumps()` for objects, lists flattened, nulls
+    /// skipped. Floats are declined because Python's `repr` and Rust's float
+    /// formatting disagree on exponents.
+    fn count_text_value(&self, value: &TextValue) -> Result<usize, Error> {
+        match value {
+            TextValue::Null => Ok(0),
+            TextValue::Bool(true) => self.count_text("True"),
+            TextValue::Bool(false) => self.count_text("False"),
+            TextValue::Number(number) => match (number.as_i64(), number.as_u64()) {
+                (Some(number), _) => self.count_text(itoa::Buffer::new().format(number)),
+                (_, Some(number)) => self.count_text(itoa::Buffer::new().format(number)),
+                _ => Err(Error::FloatText),
+            },
+            TextValue::Text(text) => self.count_text(text),
+            TextValue::List(items) => items
+                .iter()
+                .map(|item| self.count_text_value(item))
+                .sum::<Result<usize, _>>(),
+            TextValue::Object(_) => self.count_text(&python_json::dumps(value)?),
+        }
+    }
+
+    fn count_message(&self, message: &Message) -> Result<usize, Error> {
+        let role_tokens = match &message.role {
+            Some(role) => self.count_text(role)?,
+            None => 0,
+        };
+        let name_tokens = match &message.name {
+            Some(name) => self.count_text(name)? + TOKENS_PER_NAME,
+            None => 0,
+        };
+        let content_tokens = match &message.content {
+            Some(MessageContent::Text(text)) => self.count_text(text)?,
+            Some(MessageContent::Blocks(items)) => items
+                .iter()
+                .map(|item| self.count_content_item(item))
+                .sum::<Result<usize, _>>()?,
+            None => 0,
+        };
+        Ok(TOKENS_PER_MESSAGE + role_tokens + name_tokens + content_tokens)
+    }
+
+    fn count_content_item(&self, item: &ContentItem) -> Result<usize, Error> {
+        match item {
+            ContentItem::Text(text) => self.count_text(text),
+            ContentItem::Block(ContentBlock::Text { text }) => self.count_text(text),
+            ContentItem::Block(ContentBlock::Thinking { thinking }) => {
+                if thinking.is_empty() {
+                    return Ok(0);
+                }
+                self.count_text(thinking)
+            }
+            ContentItem::Block(ContentBlock::ToolReference { tool_name }) => {
+                match tool_name.as_deref().filter(|name| !name.is_empty()) {
+                    Some(name) => self.count_text(name),
+                    None => Ok(0),
+                }
+            }
+            ContentItem::Block(ContentBlock::Unsupported) => Err(Error::ContentBlock),
+        }
+    }
+
+    fn count_extra(
+        &self,
+        tools: &[ToolDefinition],
+        tool_choice: Option<&ToolChoice>,
+        includes_system_message: bool,
+    ) -> Result<usize, Error> {
+        let tool_tokens = if tools.is_empty() {
+            0
+        } else {
+            let definitions = self.count_text(&format_function_definitions(tools)?)?;
+            let discount = if includes_system_message {
+                TOOLS_WITH_SYSTEM_MESSAGE_DISCOUNT
+            } else {
+                0
+            };
+            definitions + TOOL_DEFINITIONS_TOKENS - discount
+        };
+        let choice_tokens = match tool_choice {
+            Some(ToolChoice::Mode(mode)) if mode == "none" => TOOL_CHOICE_NONE_TOKENS,
+            Some(ToolChoice::Mode(_)) | None => 0,
+            Some(ToolChoice::Named(named)) => {
+                NAMED_TOOL_CHOICE_TOKENS + self.count_text(&named.function.name)?
+            }
+        };
+        Ok(REPLY_PRIMING_TOKENS + tool_tokens + choice_tokens)
+    }
+}
diff --git a/litellm-rust/crates/token-counter/src/error.rs b/litellm-rust/crates/token-counter/src/error.rs
new file mode 100644
index 00000000000..dc590093f64
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/error.rs
@@ -0,0 +1,31 @@
+use std::string::FromUtf8Error;
+
+use thiserror::Error as ThisError;
+
+#[derive(Debug, ThisError)]
+pub enum Error {
+    #[error("failed to load tokenizer: {0}")]
+    Load(#[source] tokenizers::Error),
+    #[error("unsupported by the rust token counter: request body could not be parsed: {0}")]
+    RequestParse(#[source] serde_json::Error),
+    #[error("unsupported by the rust token counter: request has no countable input")]
+    MissingInput,
+    #[error(
+        "unsupported by the rust token counter: float text values are counted by the python path"
+    )]
+    FloatText,
+    #[error(
+        "unsupported by the rust token counter: content block type is counted by the python path"
+    )]
+    ContentBlock,
+    #[error("unsupported by the rust token counter: array parameter without items")]
+    ArrayItems,
+    #[error("unsupported by the rust token counter: text value could not be serialized: {0}")]
+    JsonSerialization(#[source] serde_json::Error),
+    #[error("unsupported by the rust token counter: serialized text value is not UTF-8: {0}")]
+    JsonUtf8(#[source] FromUtf8Error),
+    #[error("tokenization failed: {0}")]
+    Encode(#[source] tokenizers::Error),
+    #[error("token counting task failed: {0}")]
+    Task(String),
+}
diff --git a/litellm-rust/crates/token-counter/src/lib.rs b/litellm-rust/crates/token-counter/src/lib.rs
new file mode 100644
index 00000000000..eb602b3cade
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/lib.rs
@@ -0,0 +1,17 @@
+//! Input token counting for a request body, mirroring `litellm.token_counter`
+//! for the shapes it can count exactly. Everything else is declined so the host
+//! keeps its own counter as the reference.
+
+#![forbid(unsafe_code)]
+
+mod byte_level;
+mod counter;
+mod error;
+mod python_json;
+mod tools;
+mod types;
+mod unicode_classes;
+
+pub use counter::{InputTokenCount, TokenCounter};
+pub use error::Error;
+pub use types::CountableRequest;
diff --git a/litellm-rust/crates/token-counter/src/python_json.rs b/litellm-rust/crates/token-counter/src/python_json.rs
new file mode 100644
index 00000000000..00a55ad300c
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/python_json.rs
@@ -0,0 +1,155 @@
+//! `json.dumps(value)` with Python's default arguments: `", "` and `": "`
+//! separators, `ensure_ascii=True`, and keys in insertion order.
+
+use std::io::{self, Write};
+
+use serde::Serialize;
+use serde_json::ser::{Formatter, Serializer};
+
+use super::Error;
+use super::types::TextValue;
+
+pub(super) fn dumps(value: &TextValue) -> Result<String, Error> {
+    let mut output = Vec::with_capacity(serialized_len(value)?);
+    value
+        .serialize(&mut Serializer::with_formatter(
+            &mut output,
+            PythonFormatter,
+        ))
+        .map_err(Error::JsonSerialization)?;
+    debug_assert_eq!(output.len(), output.capacity());
+    String::from_utf8(output).map_err(Error::JsonUtf8)
+}
+
+fn serialized_len(value: &TextValue) -> Result<usize, Error> {
+    match value {
+        TextValue::Null => Ok(4),
+        TextValue::Bool(true) => Ok(4),
+        TextValue::Bool(false) => Ok(5),
+        TextValue::Number(number) => match (number.as_i64(), number.as_u64()) {
+            (Some(number), _) => Ok(unsigned_len(number.unsigned_abs()) + usize::from(number < 0)),
+            (_, Some(number)) => Ok(unsigned_len(number)),
+            _ => Err(Error::FloatText),
+        },
+        TextValue::Text(text) => Ok(quoted_len(text)),
+        TextValue::List(items) => items
+            .iter()
+            .try_fold(2 + items.len().saturating_sub(1) * 2, |len, item| {
+                Ok(len + serialized_len(item)?)
+            }),
+        TextValue::Object(entries) => entries.iter().try_fold(
+            2 + entries.len().saturating_sub(1) * 2,
+            |len, (key, value)| Ok(len + quoted_len(key) + 2 + serialized_len(value)?),
+        ),
+    }
+}
+
+fn unsigned_len(number: u64) -> usize {
+    if number == 0 {
+        1
+    } else {
+        number.ilog10() as usize + 1
+    }
+}
+
+fn quoted_len(value: &str) -> usize {
+    value.chars().fold(2, |len, character| {
+        len + match character {
+            '"' | '\\' | '\u{0008}' | '\u{000c}' | '\n' | '\r' | '\t' => 2,
+            '\u{0000}'..='\u{001f}' => 6,
+            ' '..='~' => 1,
+            _ => character.len_utf16() * 6,
+        }
+    })
+}
+
+struct PythonFormatter;
+
+impl Formatter for PythonFormatter {
+    fn begin_array_value<W>(&mut self, writer: &mut W, first: bool) -> io::Result<()>
+    where
+        W: ?Sized + Write,
+    {
+        if !first {
+            writer.write_all(b", ")?;
+        }
+        Ok(())
+    }
+
+    fn begin_object_key<W>(&mut self, writer: &mut W, first: bool) -> io::Result<()>
+    where
+        W: ?Sized + Write,
+    {
+        if !first {
+            writer.write_all(b", ")?;
+        }
+        Ok(())
+    }
+
+    fn begin_object_value<W>(&mut self, writer: &mut W) -> io::Result<()>
+    where
+        W: ?Sized + Write,
+    {
+        writer.write_all(b": ")
+    }
+
+    fn write_string_fragment<W>(&mut self, writer: &mut W, fragment: &str) -> io::Result<()>
+    where
+        W: ?Sized + Write,
+    {
+        for character in fragment.chars() {
+            if (' '..='~').contains(&character) {
+                write!(writer, "{character}")?;
+                continue;
+            }
+            let mut units = [0u16; 2];
+            for unit in character.encode_utf16(&mut units) {
+                write!(writer, "\\u{unit:04x}")?;
+            }
+        }
+        Ok(())
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use rstest::rstest;
+
+    use super::dumps;
+
+    #[rstest]
+    #[case::null("null", "null")]
+    #[case::boolean("true", "true")]
+    #[case::signed_integer("-3", "-3")]
+    #[case::unsigned_integer("18446744073709551615", "18446744073709551615")]
+    #[case::empty_array("[]", "[]")]
+    #[case::empty_object("{}", "{}")]
+    #[case::nested(
+        r#"{"first":1,"second":{"ok":true,"none":null},"third":[false,2]}"#,
+        r#"{"first": 1, "second": {"ok": true, "none": null}, "third": [false, 2]}"#
+    )]
+    #[case::string_escaping(
+        r#""caf\u00e9 \u2014 \ud83d\ude00 \"q\" \\ \n\t\u0001\u007f ~ /""#,
+        r#""caf\u00e9 \u2014 \ud83d\ude00 \"q\" \\ \n\t\u0001\u007f ~ /""#
+    )]
+    #[case::short_control_escapes(r#""\b\f\r""#, r#""\b\f\r""#)]
+    fn matches_python_json_dumps(#[case] input: &str, #[case] expected: &str) {
+        let value = serde_json::from_str(input).expect("fixture parses");
+
+        assert_eq!(dumps(&value).expect("fixture dumps"), expected);
+    }
+
+    #[rstest]
+    #[case::top_level("1.5")]
+    #[case::array("[1,2.5]")]
+    #[case::object(r#"{"nested":{"value":-0.25}}"#)]
+    fn rejects_floats(#[case] input: &str) {
+        let value = serde_json::from_str(input).expect("fixture parses");
+        let error = dumps(&value).expect_err("floats are declined");
+
+        assert_eq!(
+            error.to_string(),
+            "unsupported by the rust token counter: float text values are counted by the python path"
+        );
+    }
+}
diff --git a/litellm-rust/crates/token-counter/src/tools.rs b/litellm-rust/crates/token-counter/src/tools.rs
new file mode 100644
index 00000000000..22150a4e4b1
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/tools.rs
@@ -0,0 +1,304 @@
+//! Renders tool definitions the way `litellm.token_counter` does before
+//! tokenizing them (the TypeScript-like namespace OpenAI appears to use).
+
+use std::fmt::Write;
+
+use super::Error;
+use super::types::{EnumValue, Schema, SchemaType, ToolDefinition};
+
+pub(super) fn format_function_definitions(tools: &[ToolDefinition]) -> Result<String, Error> {
+    ToolFormatter::new(tools.len()).format(tools)
+}
+
+struct ToolFormatter {
+    output: String,
+}
+
+impl ToolFormatter {
+    fn new(tool_count: usize) -> Self {
+        Self {
+            output: String::with_capacity(tool_count.saturating_mul(128).saturating_add(48)),
+        }
+    }
+
+    fn format(mut self, tools: &[ToolDefinition]) -> Result<String, Error> {
+        self.output.push_str("namespace functions {\n\n");
+
+        for tool in tools {
+            self.write_function(tool)?;
+        }
+
+        self.output.push_str("} // namespace functions");
+        Ok(self.output)
+    }
+
+    fn write_function(&mut self, tool: &ToolDefinition) -> Result<(), Error> {
+        let (name, description, parameters) = resolve_function(tool);
+        let Some(name) = name.filter(|name| !name.is_empty()) else {
+            return Ok(());
+        };
+
+        if let Some(description) = description.filter(|description| !description.is_empty()) {
+            self.output.push_str("// ");
+            self.output.push_str(description);
+            self.output.push('\n');
+        }
+
+        match parameters.filter(|parameters| {
+            parameters
+                .properties
+                .as_ref()
+                .is_some_and(|properties| !properties.is_empty())
+        }) {
+            Some(parameters) => {
+                self.output.push_str("type ");
+                self.output.push_str(name);
+                self.output.push_str(" = (_: {\n");
+                self.write_object_parameters(parameters, 0)?;
+                self.output.push_str("\n}) => any;\n\n");
+            }
+            _ => {
+                self.output.push_str("type ");
+                self.output.push_str(name);
+                self.output.push_str(" = () => any;\n\n");
+            }
+        }
+
+        Ok(())
+    }
+
+    fn write_object_parameters(&mut self, parameters: &Schema, indent: usize) -> Result<(), Error> {
+        let Some(properties) = parameters
+            .properties
+            .as_ref()
+            .filter(|properties| !properties.is_empty())
+        else {
+            return Ok(());
+        };
+        let required = parameters.required.as_deref().unwrap_or_default();
+        for (index, (key, props)) in properties.iter().enumerate() {
+            if index > 0 {
+                self.output.push('\n');
+            }
+            if let Some(description) = props
+                .description
+                .as_deref()
+                .filter(|description| !description.is_empty())
+            {
+                self.write_indent(indent);
+                self.output.push_str("// ");
+                self.output.push_str(description);
+                self.output.push('\n');
+            }
+
+            self.write_indent(indent);
+            self.output.push_str(key);
+            if !required.iter().any(|required| required == key) {
+                self.output.push('?');
+            }
+            self.output.push_str(": ");
+            self.write_type(props, indent)?;
+            self.output.push(',');
+        }
+
+        Ok(())
+    }
+
+    fn write_type(&mut self, props: &Schema, indent: usize) -> Result<(), Error> {
+        let Some(SchemaType::Name(schema_type)) = &props.schema_type else {
+            self.output.push_str("any");
+            return Ok(());
+        };
+
+        match schema_type.as_str() {
+            "string" | "integer" | "number" => match &props.enum_values {
+                Some(values) => self.write_enum(values),
+                None if schema_type == "string" => self.output.push_str("string"),
+                None => self.output.push_str("number"),
+            },
+            "array" => {
+                let items = props.items.as_deref().ok_or(Error::ArrayItems)?;
+                self.write_type(items, indent)?;
+                self.output.push_str("[]");
+            }
+            "object" => {
+                self.output.push_str("{\n");
+                self.write_object_parameters(props, indent + 2)?;
+                self.output.push_str("\n}");
+            }
+            "boolean" => self.output.push_str("boolean"),
+            "null" => self.output.push_str("null"),
+            _ => self.output.push_str("any"),
+        }
+
+        Ok(())
+    }
+
+    fn write_enum(&mut self, values: &[EnumValue]) {
+        for (index, value) in values.iter().enumerate() {
+            if index > 0 {
+                self.output.push_str(" | ");
+            }
+            self.output.push('"');
+            match value {
+                EnumValue::Text(text) => self.output.push_str(text),
+                EnumValue::Integer(number) => {
+                    write!(self.output, "{number}").expect("writing to a String cannot fail");
+                }
+            }
+            self.output.push('"');
+        }
+    }
+
+    fn write_indent(&mut self, indent: usize) {
+        for _ in 0..indent {
+            self.output.push(' ');
+        }
+    }
+}
+
+fn resolve_function(tool: &ToolDefinition) -> (Option<&str>, Option<&str>, Option<&Schema>) {
+    match &tool.function {
+        Some(function) => (
+            function.name.as_deref(),
+            function.description.as_deref(),
+            function.parameters.as_ref(),
+        ),
+        None => (
+            tool.name.as_deref(),
+            tool.description.as_deref(),
+            tool.input_schema.as_ref().or(tool.parameters.as_ref()),
+        ),
+    }
+}
+
+#[cfg(test)]
+mod tests {
+    use super::*;
+
+    fn parse_tools(json: &str) -> Vec<ToolDefinition> {
+        serde_json::from_str(json).expect("tool fixture parses")
+    }
+
+    #[test]
+    fn empty_tool_list_renders_an_empty_namespace() {
+        assert_eq!(
+            format_function_definitions(&[]).expect("empty tool list renders"),
+            "namespace functions {\n\n} // namespace functions"
+        );
+    }
+
+    #[test]
+    fn unnamed_tools_are_skipped_and_function_shape_takes_precedence() {
+        let tools = parse_tools(
+            r#"[
+                {},
+                {"name":""},
+                {"name":"ignored","function":{"description":"missing a function name"}},
+                {"name":"ping","description":""}
+            ]"#,
+        );
+
+        assert_eq!(
+            format_function_definitions(&tools).expect("tools render"),
+            "namespace functions {\n\ntype ping = () => any;\n\n} // namespace functions"
+        );
+    }
+
+    #[test]
+    fn empty_or_missing_properties_render_a_no_argument_function() {
+        let tools = parse_tools(
+            r#"[
+                {"name":"missing","input_schema":{"type":"object"}},
+                {"name":"empty","input_schema":{"type":"object","properties":{}}}
+            ]"#,
+        );
+
+        assert_eq!(
+            format_function_definitions(&tools).expect("tools render"),
+            concat!(
+                "namespace functions {\n\n",
+                "type missing = () => any;\n\n",
+                "type empty = () => any;\n\n",
+                "} // namespace functions"
+            )
+        );
+    }
+
+    #[test]
+    fn anthropic_parameters_render_all_supported_types() {
+        let tools = parse_tools(
+            r#"[{
+                "name":"inspect",
+                "description":"Inspect a value",
+                "input_schema":{
+                    "type":"object",
+                    "properties":{
+                        "text":{"type":"string"},
+                        "count":{"type":"integer","description":"Number of attempts"},
+                        "ratio":{"type":"number"},
+                        "enabled":{"type":"boolean"},
+                        "nothing":{"type":"null"},
+                        "unknown":{"type":"custom"},
+                        "union":{"type":["string","null"]},
+                        "labels":{"type":"array","items":{"type":"string"}},
+                        "config":{"type":"object","properties":{"retries":{"type":"integer"}},"required":["retries"]},
+                        "mode":{"type":"string","enum":["fast",2]}
+                    },
+                    "required":["text"]
+                }
+            }]"#,
+        );
+
+        assert_eq!(
+            format_function_definitions(&tools).expect("tool renders"),
+            concat!(
+                "namespace functions {\n\n",
+                "// Inspect a value\n",
+                "type inspect = (_: {\n",
+                "text: string,\n",
+                "// Number of attempts\n",
+                "count?: number,\n",
+                "ratio?: number,\n",
+                "enabled?: boolean,\n",
+                "nothing?: null,\n",
+                "unknown?: any,\n",
+                "union?: any,\n",
+                "labels?: string[],\n",
+                "config?: {\n",
+                "  retries: number,\n",
+                "},\n",
+                "mode?: \"fast\" | \"2\",\n",
+                "}) => any;\n\n",
+                "} // namespace functions"
+            )
+        );
+    }
+
+    #[test]
+    fn input_schema_takes_precedence_over_legacy_parameters() {
+        let tools = parse_tools(
+            r#"[{
+                "name":"choose",
+                "input_schema":{"type":"object","properties":{"current":{"type":"string"}}},
+                "parameters":{"type":"object","properties":{"legacy":{"type":"string"}}}
+            }]"#,
+        );
+
+        let rendered = format_function_definitions(&tools).expect("tool renders");
+        assert!(rendered.contains("current?: string,"));
+        assert!(!rendered.contains("legacy"));
+    }
+
+    #[test]
+    fn array_without_items_returns_an_error() {
+        let tools = parse_tools(
+            r#"[{"name":"broken","parameters":{"type":"object","properties":{"values":{"type":"array"}}}}]"#,
+        );
+
+        assert!(matches!(
+            format_function_definitions(&tools),
+            Err(Error::ArrayItems)
+        ));
+    }
+}
diff --git a/litellm-rust/crates/token-counter/src/types.rs b/litellm-rust/crates/token-counter/src/types.rs
new file mode 100644
index 00000000000..d25554beaac
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/types.rs
@@ -0,0 +1,238 @@
+use std::fmt;
+
+use indexmap::IndexMap;
+use serde::de::{MapAccess, SeqAccess, Visitor};
+use serde::{Deserialize, Deserializer, Serialize};
+use serde_json::Number;
+
+use super::Error;
+
+/// The parts of a request body the host's budget counter reads. Chat and
+/// Anthropic Messages bodies carry `messages`; completions carry `prompt`;
+/// Responses and embeddings carry `input`; rerank carries `query` and
+/// `documents`. The host checks key presence, not nullness, so an explicit
+/// `null` is kept distinct from an absent key. Anything outside this shape is
+/// declined so the host can fall back to its own counter instead of silently
+/// miscounting.
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+pub struct CountableRequest {
+    pub(crate) model: Option<String>,
+    #[serde(default, deserialize_with = "present_messages")]
+    pub(crate) messages: Option<Vec<Message>>,
+    pub(crate) tools: Option<Vec<ToolDefinition>>,
+    pub(crate) tool_choice: Option<ToolChoice>,
+    #[serde(default, deserialize_with = "present_text")]
+    pub(crate) prompt: Option<TextValue>,
+    #[serde(default, deserialize_with = "present_text")]
+    pub(crate) input: Option<TextValue>,
+    #[serde(default, deserialize_with = "present_text")]
+    pub(crate) query: Option<TextValue>,
+    #[serde(default, deserialize_with = "present_text")]
+    pub(crate) documents: Option<TextValue>,
+}
+
+impl CountableRequest {
+    pub fn parse(body: &[u8]) -> Result<Self, Error> {
+        serde_json::from_slice(body).map_err(Error::RequestParse)
+    }
+}
+
+fn present_messages<'de, D: Deserializer<'de>>(
+    deserializer: D,
+) -> Result<Option<Vec<Message>>, D::Error> {
+    Option::<Vec<Message>>::deserialize(deserializer)
+        .map(|messages| Some(messages.unwrap_or_default()))
+}
+
+fn present_text<'de, D: Deserializer<'de>>(deserializer: D) -> Result<Option<TextValue>, D::Error> {
+    TextValue::deserialize(deserializer).map(Some)
+}
+
+/// Free-form JSON the host counts as text: strings and integers via `str()`,
+/// objects via `json.dumps()`, lists flattened. Objects keep document order so
+/// the dumped text matches Python byte for byte.
+#[derive(Clone, Debug, PartialEq, Serialize)]
+#[serde(untagged)]
+pub(crate) enum TextValue {
+    Null,
+    Bool(bool),
+    Number(Number),
+    Text(String),
+    List(Vec<TextValue>),
+    Object(IndexMap<String, TextValue>),
+}
+
+impl<'de> Deserialize<'de> for TextValue {
+    fn deserialize<D: Deserializer<'de>>(deserializer: D) -> Result<Self, D::Error> {
+        deserializer.deserialize_any(TextValueVisitor)
+    }
+}
+
+struct TextValueVisitor;
+
+impl<'de> Visitor<'de> for TextValueVisitor {
+    type Value = TextValue;
+
+    fn expecting(&self, formatter: &mut fmt::Formatter<'_>) -> fmt::Result {
+        formatter.write_str("a JSON value")
+    }
+
+    fn visit_unit<E>(self) -> Result<Self::Value, E> {
+        Ok(TextValue::Null)
+    }
+
+    fn visit_none<E>(self) -> Result<Self::Value, E> {
+        Ok(TextValue::Null)
+    }
+
+    fn visit_bool<E>(self, value: bool) -> Result<Self::Value, E> {
+        Ok(TextValue::Bool(value))
+    }
+
+    fn visit_i64<E>(self, value: i64) -> Result<Self::Value, E> {
+        Ok(TextValue::Number(value.into()))
+    }
+
+    fn visit_u64<E>(self, value: u64) -> Result<Self::Value, E> {
+        Ok(TextValue::Number(value.into()))
+    }
+
+    fn visit_f64<E>(self, value: f64) -> Result<Self::Value, E>
+    where
+        E: serde::de::Error,
+    {
+        Number::from_f64(value)
+            .map(TextValue::Number)
+            .ok_or_else(|| E::custom("non-finite JSON number"))
+    }
+
+    fn visit_str<E>(self, value: &str) -> Result<Self::Value, E> {
+        Ok(TextValue::Text(value.to_owned()))
+    }
+
+    fn visit_string<E>(self, value: String) -> Result<Self::Value, E> {
+        Ok(TextValue::Text(value))
+    }
+
+    fn visit_seq<A>(self, mut sequence: A) -> Result<Self::Value, A::Error>
+    where
+        A: SeqAccess<'de>,
+    {
+        let mut items = Vec::with_capacity(sequence.size_hint().unwrap_or(0));
+        while let Some(item) = sequence.next_element()? {
+            items.push(item);
+        }
+        Ok(TextValue::List(items))
+    }
+
+    fn visit_map<A>(self, mut map: A) -> Result<Self::Value, A::Error>
+    where
+        A: MapAccess<'de>,
+    {
+        let mut entries = IndexMap::with_capacity(map.size_hint().unwrap_or(0));
+        while let Some((key, value)) = map.next_entry()? {
+            entries.insert(key, value);
+        }
+        Ok(TextValue::Object(entries))
+    }
+}
+
+/// Python counts every string-valued key of a message, so any key beyond these
+/// makes the shape unsupported rather than silently uncounted.
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(deny_unknown_fields)]
+pub(crate) struct Message {
+    pub(crate) role: Option<String>,
+    pub(crate) name: Option<String>,
+    pub(crate) content: Option<MessageContent>,
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(untagged)]
+pub(crate) enum MessageContent {
+    Text(String),
+    Blocks(Vec<ContentItem>),
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(untagged)]
+pub(crate) enum ContentItem {
+    Text(String),
+    Block(ContentBlock),
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(tag = "type")]
+pub(crate) enum ContentBlock {
+    #[serde(rename = "text")]
+    Text { text: String },
+    #[serde(rename = "thinking")]
+    Thinking { thinking: String },
+    #[serde(rename = "tool_reference")]
+    ToolReference { tool_name: Option<String> },
+    /// Images, documents, files and tool use/result blocks price through
+    /// Python-only helpers, so they stay on the Python counter.
+    #[serde(other)]
+    Unsupported,
+}
+
+/// Either the OpenAI `{"type": "function", "function": {...}}` shape or the
+/// Anthropic `{"name", "description", "input_schema"}` shape.
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+pub(crate) struct ToolDefinition {
+    pub(crate) function: Option<FunctionDefinition>,
+    pub(crate) name: Option<String>,
+    pub(crate) description: Option<String>,
+    pub(crate) input_schema: Option<Schema>,
+    pub(crate) parameters: Option<Schema>,
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+pub(crate) struct FunctionDefinition {
+    pub(crate) name: Option<String>,
+    pub(crate) description: Option<String>,
+    pub(crate) parameters: Option<Schema>,
+}
+
+#[derive(Clone, Debug, Default, Deserialize, PartialEq)]
+pub(crate) struct Schema {
+    #[serde(rename = "type")]
+    pub(crate) schema_type: Option<SchemaType>,
+    pub(crate) description: Option<String>,
+    #[serde(rename = "enum")]
+    pub(crate) enum_values: Option<Vec<EnumValue>>,
+    pub(crate) items: Option<Box<Schema>>,
+    pub(crate) properties: Option<IndexMap<String, Schema>>,
+    pub(crate) required: Option<Vec<String>>,
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(untagged)]
+pub(crate) enum SchemaType {
+    Name(String),
+    Union(Vec<String>),
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(untagged)]
+pub(crate) enum EnumValue {
+    Text(String),
+    Integer(i64),
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+#[serde(untagged)]
+pub(crate) enum ToolChoice {
+    Mode(String),
+    Named(NamedToolChoice),
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+pub(crate) struct NamedToolChoice {
+    pub(crate) function: NamedFunction,
+}
+
+#[derive(Clone, Debug, Deserialize, PartialEq)]
+pub(crate) struct NamedFunction {
+    pub(crate) name: String,
+}
diff --git a/litellm-rust/crates/token-counter/src/unicode_classes.rs b/litellm-rust/crates/token-counter/src/unicode_classes.rs
new file mode 100644
index 00000000000..405cee34949
--- /dev/null
+++ b/litellm-rust/crates/token-counter/src/unicode_classes.rs
@@ -0,0 +1,73 @@
+use std::cmp::Ordering;
+use std::sync::LazyLock;
+
+use tokenizers::utils::SysRegex;
+
+struct Ranges(Box<[(u32, u32)]>);
+
+pub(super) struct UnicodeClasses {
+    letters: Ranges,
+    numbers: Ranges,
+    spaces: Ranges,
+}
+
+static CLASSES: LazyLock<Option<UnicodeClasses>> = LazyLock::new(|| {
+    let scalars: String = (0..=u32::from(char::MAX))
+        .filter_map(char::from_u32)
+        .collect();
+    Some(UnicodeClasses {
+        letters: Ranges::load(r"\p{L}+", &scalars)?,
+        numbers: Ranges::load(r"\p{N}+", &scalars)?,
+        spaces: Ranges::load(r"\s+", &scalars)?,
+    })
+});
+
+impl Ranges {
+    fn load(pattern: &str, scalars: &str) -> Option<Self> {
+        let regex = SysRegex::new(pattern).ok()?;
+        let ranges = regex
+            .find_iter(scalars)
+            .map(|(start, end)| {
+                let matched = scalars.get(start..end)?;
+                Some((
+                    u32::from(matched.chars().next()?),
+                    u32::from(matched.chars().next_back()?),
+                ))
+            })
+            .collect::<Option<Box<[_]>>>()?;
+        Some(Self(ranges))
+    }
+
+    fn contains(&self, character: char) -> bool {
+        let code = u32::from(character);
+        self.0
+            .binary_search_by(|(low, high)| {
+                if *high < code {
+                    Ordering::Less
+                } else if *low > code {
+                    Ordering::Greater
+                } else {
+                    Ordering::Equal
+                }
+            })
+            .is_ok()
+    }
+}
+
+impl UnicodeClasses {
+    pub(super) fn get() -> Option<&'static Self> {
+        CLASSES.as_ref()
+    }
+
+    pub(super) fn is_letter(&self, character: char) -> bool {
+        self.letters.contains(character)
+    }
+
+    pub(super) fn is_number(&self, character: char) -> bool {
+        self.numbers.contains(character)
+    }
+
+    pub(super) fn is_space(&self, character: char) -> bool {
+        self.spaces.contains(character)
+    }
+}
diff --git a/litellm-rust/crates/token-counter/tests/token_counter.rs b/litellm-rust/crates/token-counter/tests/token_counter.rs
new file mode 100644
index 00000000000..0e71a5c03cf
--- /dev/null
+++ b/litellm-rust/crates/token-counter/tests/token_counter.rs
@@ -0,0 +1,176 @@
+use rstest::rstest;
+
+use litellm_token_counter::{CountableRequest, Error, InputTokenCount, TokenCounter};
+
+/// Expected counts are pinned from `litellm.token_counter(model="claude-sonnet-4-5", ...)`
+/// so this test also guards Python parity.
+fn counter() -> TokenCounter {
+    let path = concat!(
+        env!("CARGO_MANIFEST_DIR"),
+        "/../../../litellm/litellm_core_utils/tokenizers/anthropic_tokenizer.json"
+    );
+    let json = std::fs::read_to_string(path).expect("anthropic tokenizer json is in the repo");
+    TokenCounter::from_json(&json).expect("anthropic tokenizer loads")
+}
+
+const SIMPLE: &str = r#"{"model":"claude-sonnet-4-5","messages":[{"role":"user","content":"Hello, how are you today?"}]}"#;
+
+const BLOCKS_AND_SYSTEM: &str = r#"{"model":"claude-sonnet-4-5","messages":[
+  {"role":"system","content":"You are a terse assistant."},
+  {"role":"user","name":"alice","content":[
+    {"type":"text","text":"Summarise this paragraph about ships and harbours."},
+    "plain string item",
+    {"type":"thinking","thinking":"pondering"},
+    {"type":"tool_reference","tool_name":"get_weather"}]},
+  {"role":"assistant","content":[{"type":"text","text":"Sure.","cache_control":{"type":"ephemeral"}}]}]}"#;
+
+const TOOLS_OPENAI: &str = r#"{"model":"claude-sonnet-4-5","messages":[{"role":"user","content":"weather?"}],
+  "tools":[
+    {"type":"function","function":{"name":"get_weather","description":"Get weather","parameters":{
+      "type":"object",
+      "properties":{
+        "location":{"type":"string","description":"City name"},
+        "unit":{"type":"string","enum":["celsius","fahrenheit"]},
+        "days":{"type":"integer"},
+        "tags":{"type":"array","items":{"type":"string"}},
+        "opts":{"type":"object","properties":{"verbose":{"type":"boolean"},"level":{"type":"integer","enum":[1,2]}},"required":["verbose"]},
+        "anything":{}},
+      "required":["location"]}}},
+    {"type":"function","function":{"name":"noop"}}],
+  "tool_choice":{"type":"function","function":{"name":"get_weather"}}}"#;
+
+const TOOLS_ANTHROPIC_SYSTEM: &str = r#"{"model":"claude-sonnet-4-5",
+  "messages":[{"role":"system","content":"sys"},{"role":"user","content":"weather?"}],
+  "tools":[{"name":"get_weather","description":"Get weather","input_schema":{
+    "type":"object","properties":{"location":{"type":["string","null"]}},"required":["location"]}}],
+  "tool_choice":"none"}"#;
+
+const COMPLETIONS_PROMPT: &str =
+    r#"{"model":"claude-sonnet-4-5","prompt":"Write a haiku about ships."}"#;
+
+const COMPLETIONS_PROMPT_LIST: &str =
+    r#"{"model":"claude-sonnet-4-5","prompt":["first prompt","second prompt"]}"#;
+
+const RESPONSES_INPUT: &str = r#"{"model":"claude-sonnet-4-5","input":[
+  {"role":"user","content":[{"type":"input_text","text":"Summarise caf\u00e9 menus, na\u00efve \u2014 ok? \"quoted\"\n"}]},
+  {"role":"assistant","content":"Sure."}],"instructions":"be terse"}"#;
+
+const EMBEDDINGS_TOKEN_IDS: &str =
+    r#"{"model":"claude-sonnet-4-5","input":[[101,2023,5],[7]],"encoding_format":"float"}"#;
+
+const RERANK: &str = r#"{"model":"claude-sonnet-4-5","query":"best harbour",
+  "documents":["doc one",{"text":"doc two","title":"T","n":3,"ok":true,"none":null,"tags":["a","b"]}]}"#;
+
+/// Expected counts are pinned from
+/// `litellm.proxy.spend_tracking.budget_reservation._count_input_tokens(body, "claude-sonnet-4-5")`.
+#[rstest]
+#[case::text_only(SIMPLE, 14)]
+#[case::content_blocks_name_and_system(BLOCKS_AND_SYSTEM, 45)]
+#[case::openai_tools_named_choice(TOOLS_OPENAI, 123)]
+#[case::anthropic_tools_system_discount_choice_none(TOOLS_ANTHROPIC_SYSTEM, 53)]
+#[case::completions_prompt(COMPLETIONS_PROMPT, 7)]
+#[case::completions_prompt_list(COMPLETIONS_PROMPT_LIST, 4)]
+#[case::responses_input_items(RESPONSES_INPUT, 62)]
+#[case::embeddings_token_ids(EMBEDDINGS_TOKEN_IDS, 5)]
+#[case::rerank_query_and_documents(RERANK, 41)]
+fn count_request_matches_python_token_counter(#[case] body: &str, #[case] expected: usize) {
+    let request = CountableRequest::parse(body.as_bytes()).expect("fixture parses");
+    let count = counter().count_request(&request).expect("fixture counts");
+    assert_eq!(
+        count,
+        InputTokenCount {
+            model: Some("claude-sonnet-4-5".to_string()),
+            input_tokens: expected,
+        }
+    );
+}
+
+#[rstest]
+#[case::null_messages_win_over_prompt(r#"{"model":"m","messages":null,"prompt":"ignored"}"#, 3)]
+#[case::model_from_route(r#"{"prompt":"hi"}"#, 1)]
+#[case::bools_and_ints_use_python_str(r#"{"model":"m","prompt":[true,false,42]}"#, 3)]
+#[case::null_prompt_counts_zero(r#"{"model":"m","prompt":null}"#, 0)]
+fn key_presence_follows_python(#[case] body: &str, #[case] expected: usize) {
+    let request = CountableRequest::parse(body.as_bytes()).expect("fixture parses");
+    let count = counter().count_request(&request).expect("fixture counts");
+    assert_eq!(count.input_tokens, expected);
+}
+
+#[rstest]
+#[case::not_json(b"not json" as &[u8])]
+#[case::messages_not_a_list(br#"{"model":"m","messages":"hi"}"#)]
+#[case::message_with_tool_calls(
+    br#"{"model":"m","messages":[{"role":"assistant","tool_calls":[{"id":"1","type":"function","function":{"name":"f","arguments":"{}"}}]}]}"#
+)]
+#[case::dict_content(
+    br#"{"model":"m","messages":[{"role":"user","content":{"type":"text","text":"x"}}]}"#
+)]
+#[case::float_enum(
+    br#"{"model":"m","messages":[],"tools":[{"name":"f","input_schema":{"type":"object","properties":{"x":{"type":"number","enum":[1.5]}}}}]}"#
+)]
+#[case::anthropic_tool_choice_without_function(
+    br#"{"model":"m","messages":[],"tool_choice":{"type":"auto"}}"#
+)]
+fn shapes_outside_the_mirror_are_declined_at_parse(#[case] body: &[u8]) {
+    assert!(matches!(
+        CountableRequest::parse(body),
+        Err(Error::RequestParse(_))
+    ));
+}
+
+#[rstest]
+#[case::no_countable_input(br#"{"model":"m","instructions":"hi"}"# as &[u8])]
+#[case::float_prompt(br#"{"model":"m","prompt":1.5}"#)]
+#[case::float_inside_document(br#"{"model":"m","documents":[{"score":0.5}]}"#)]
+#[case::image_block(
+    br#"{"model":"m","messages":[{"role":"user","content":[{"type":"image","source":{"type":"base64","media_type":"image/png","data":"AA=="}}]}]}"#
+)]
+#[case::tool_result_block(
+    br#"{"model":"m","messages":[{"role":"user","content":[{"type":"tool_result","tool_use_id":"1","content":"ok"}]}]}"#
+)]
+#[case::array_without_items(
+    br#"{"model":"m","messages":[],"tools":[{"name":"f","input_schema":{"type":"object","properties":{"x":{"type":"array"}}}}]}"#
+)]
+fn shapes_outside_the_mirror_are_declined_at_count(#[case] body: &[u8]) {
+    let request = CountableRequest::parse(body).expect("shape parses");
+    assert!(matches!(
+        counter().count_request(&request),
+        Err(Error::MissingInput | Error::FloatText | Error::ContentBlock | Error::ArrayItems)
+    ));
+}
+
+#[test]
+fn tool_choice_and_system_discount_change_the_count() {
+    let counter = counter();
+    let count = |body: &str| {
+        counter
+            .count_request(&CountableRequest::parse(body.as_bytes()).expect("parses"))
+            .expect("counts")
+            .input_tokens
+    };
+    let base = count(r#"{"model":"m","messages":[{"role":"user","content":"hi"}]}"#);
+    assert_eq!(
+        count(r#"{"model":"m","messages":[{"role":"user","content":"hi"}],"tool_choice":"none"}"#),
+        base + 1
+    );
+    assert_eq!(
+        count(r#"{"model":"m","messages":[{"role":"user","content":"hi"}],"tool_choice":"auto"}"#),
+        base
+    );
+    let with_tools = count(
+        r#"{"model":"m","messages":[{"role":"user","content":"hi"}],"tools":[{"name":"f"}]}"#,
+    );
+    let with_tools_and_system = count(
+        r#"{"model":"m","messages":[{"role":"system","content":"hi"}],"tools":[{"name":"f"}]}"#,
+    );
+    assert_eq!(with_tools - with_tools_and_system, 4);
+    assert_eq!(
+        count(r#"{"model":"m","messages":[{"role":"user","content":"hi"}],"tools":[]}"#),
+        base
+    );
+}
+
+#[test]
+fn loading_a_bad_tokenizer_is_a_load_error() {
+    assert!(matches!(TokenCounter::from_json("{}"), Err(Error::Load(_))));
+}
diff --git a/litellm/__init__.py b/litellm/__init__.py
index ede8a73453d..157aed12a83 100644
--- a/litellm/__init__.py
+++ b/litellm/__init__.py
@@ -45,9 +45,11 @@ from typing import (
     TYPE_CHECKING,
     Union,
 )
+from collections.abc import Mapping
 from litellm.types.integrations.datadog import DatadogInitParams
 from litellm.types.integrations.newrelic import NewRelicInitParams
 from litellm.litellm_core_utils.core_helpers import drop_params_env_flag
+from litellm.types.integrations.pointfive import PointFiveInitParams
 from litellm._logging import (
     set_verbose,
     _turn_on_debug,
@@ -154,6 +156,7 @@ _custom_logger_compatible_callbacks_literal = Literal[
     "smtp_email",
     "deepeval",
     "s3_v2",
+    "pointfive",
     "aws_sqs",
     "vector_store_pre_call_hook",
     "dotprompt",
@@ -439,6 +442,7 @@ s3_audit_callback_params: Optional[Dict] = None
 datadog_llm_observability_params: Optional[Union[DatadogLLMObsInitParams, Dict]] = None
 datadog_params: Optional[Union[DatadogInitParams, Dict]] = None
 newrelic_params: Optional[Union[NewRelicInitParams, Dict]] = None
+pointfive_params: Optional[Union[PointFiveInitParams, Mapping[str, object]]] = None
 aws_sqs_callback_params: Optional[Dict] = None
 generic_logger_headers: Optional[Dict] = None
 default_key_generate_params: Optional[Dict] = None
@@ -475,6 +479,7 @@ prometheus_metrics_config: Optional[List] = None
 prometheus_exclude_metrics: Optional[List[str]] = None
 prometheus_exclude_labels: Optional[List[str]] = None
 prometheus_emit_stream_label: bool = False
+prometheus_emit_input_sequence_length_label: bool = False
 prometheus_deployment_and_latency_caller_identity: Literal[
     "api_key_alias",
     "user_email",
@@ -546,7 +551,7 @@ _key_management_system: Optional["KeyManagementSystem"] = None
 #### PII MASKING ####
 output_parse_pii: bool = False
 #############################################
-from litellm.litellm_core_utils.get_model_cost_map import get_model_cost_map
+from litellm.litellm_core_utils.get_model_cost_map import get_model_cost_map, mark_litellm_import_complete
 
 model_cost = get_model_cost_map(url=model_cost_map_url)
 cost_discount_config: Dict[str, float] = {}  # Provider-specific cost discounts {"vertex_ai": 0.05} = 5% discount
@@ -2405,3 +2410,5 @@ def __getattr__(name: str) -> Any:
 
 
 # ALL_LITELLM_RESPONSE_TYPES is lazy-loaded via __getattr__ to avoid loading utils at import time
+
+mark_litellm_import_complete()
diff --git a/litellm/_internal_context.py b/litellm/_internal_context.py
index f856fe0f2b3..8132008731f 100644
--- a/litellm/_internal_context.py
+++ b/litellm/_internal_context.py
@@ -6,9 +6,33 @@ be settable from user input. Context variables are scoped to the current
 asyncio task and cannot be injected via HTTP request bodies.
 """
 
+from collections.abc import Generator
+from contextlib import contextmanager
 from contextvars import ContextVar
+from datetime import datetime, timezone
 from typing import Final
 
 # When True, suppresses async logging and billing for internal sub-calls
 # (e.g., emulated file-search steps that make nested LLM calls).
 is_internal_call: Final[ContextVar[bool]] = ContextVar("is_internal_call", default=False)
+
+# One request prices its totals, its per-token-type lines and the rates it reports on
+# separate code paths. Each reads the clock for off-peak pricing, so without a pinned
+# moment they can land on either side of a window boundary and disagree with each other.
+_billing_time: Final[ContextVar[datetime | None]] = ContextVar("billing_time", default=None)
+
+
+@contextmanager
+def pinned_billing_time(moment: datetime) -> Generator[None]:
+    """Price every rate lookup inside this block at ``moment`` rather than at each one's own clock read."""
+    token: Final = _billing_time.set(moment)
+    try:
+        yield
+    finally:
+        _billing_time.reset(token)
+
+
+def current_billing_time() -> datetime:
+    """The pinned billing moment, or now in UTC outside a pinned block."""
+    pinned: Final = _billing_time.get()
+    return pinned if pinned is not None else datetime.now(timezone.utc)
diff --git a/litellm/_redis.py b/litellm/_redis.py
index 3e68d50cf16..c5acdcb038b 100644
--- a/litellm/_redis.py
+++ b/litellm/_redis.py
@@ -24,6 +24,7 @@ from redis.credentials import CredentialProvider
 from litellm import get_secret, get_secret_str
 from litellm._redis_credential_provider import (
     AzureADCredentialProvider,
+    ElastiCacheIAMCredentialProvider,
     GCPIAMCredentialProvider,
     _generate_gcp_iam_access_token,
 )
@@ -38,6 +39,14 @@ from ._logging import verbose_logger
 
 AZURE_REDIS_SCOPE: Final = "https://redis.azure.com/.default"
 
+_AWS_IAM_KWARG_NAMES: Final = (
+    "aws_iam_auth",
+    "aws_iam_user_name",
+    "aws_iam_cache_name",
+    "aws_iam_region",
+    "aws_iam_serverless",
+)
+
 
 def _unwrapped_init_args(cls: type) -> frozenset[str]:
     """Every parameter on a single class's own ``__init__``, decorator-unwrapped.
@@ -75,6 +84,7 @@ def _get_redis_kwargs():
         "azure_client_id",
         "azure_tenant_id",
         "azure_client_secret",
+        *_AWS_IAM_KWARG_NAMES,
     }
 
     available_args: Final = {x for x in _unwrapped_init_args(redis.Redis) if x not in exclude_args} | include_args
@@ -270,6 +280,42 @@ def _redis_kwargs_from_environment():
     return return_dict
 
 
+def _coerces_to_true(value: object | None) -> bool:
+    return _str_to_bool(value) if isinstance(value, str) else bool(value)
+
+
+def _uses_tls(redis_kwargs: Mapping[str, object]) -> bool:
+    if redis_kwargs.get("startup_nodes") is not None:
+        return _coerces_to_true(redis_kwargs.get("ssl"))
+    url: Final = redis_kwargs.get("url")
+    if isinstance(url, str):
+        return urlsplit(url).scheme.lower() == "rediss"
+    return _coerces_to_true(redis_kwargs.get("ssl"))
+
+
+def _build_elasticache_iam_provider(redis_kwargs: Mapping[str, object]) -> ElastiCacheIAMCredentialProvider:
+    user_name: Final = redis_kwargs.get("aws_iam_user_name")
+    cache_name: Final = redis_kwargs.get("aws_iam_cache_name")
+    region: Final = (
+        redis_kwargs.get("aws_iam_region") or get_secret_str("AWS_REGION") or get_secret_str("AWS_DEFAULT_REGION")
+    )
+    required_settings: Final = (
+        ("aws_iam_user_name", user_name),
+        ("aws_iam_cache_name", cache_name),
+        ("aws_iam_region", region),
+    )
+    missing_settings: Final = tuple(name for name, value in required_settings if not value)
+    if missing_settings:
+        raise ValueError("AWS ElastiCache IAM Redis authentication requires: " + ", ".join(missing_settings))
+
+    return ElastiCacheIAMCredentialProvider(
+        user_name=str(user_name),
+        cache_name=str(cache_name),
+        region=str(region),
+        is_serverless=_coerces_to_true(redis_kwargs.get("aws_iam_serverless")),
+    )
+
+
 def create_gcp_iam_redis_connect_func(
     service_account: str,
     ssl_ca_certs: str | None = None,
@@ -540,6 +586,7 @@ def _get_redis_client_logic(**env_overrides):
         _azure_redis_ad_token: Final = redis_kwargs.get("azure_redis_ad_token") or get_secret("REDIS_AZURE_AD_TOKEN")
 
         _azure_ad_enabled: Final = _azure_redis_ad_token is not None and str(_azure_redis_ad_token).lower() == "true"
+        _aws_iam_enabled: Final = _coerces_to_true(redis_kwargs.get("aws_iam_auth"))
 
         if _azure_ad_enabled and _gcp_service_account is not None:
             verbose_logger.warning(
@@ -567,6 +614,22 @@ def _get_redis_client_logic(**env_overrides):
             # credentials via inspection or logging.
             redis_kwargs["redis_connect_func"]._azure_redis_ad_token = True
 
+        if _aws_iam_enabled and _gcp_service_account is not None:
+            verbose_logger.warning(
+                "Both GCP IAM (gcp_service_account) and AWS ElastiCache IAM (aws_iam_auth) are configured "
+                "for Redis. Using GCP IAM. Remove one to avoid misconfiguration."
+            )
+        elif _aws_iam_enabled and _azure_ad_enabled:
+            verbose_logger.warning(
+                "Both Azure AD (azure_redis_ad_token) and AWS ElastiCache IAM (aws_iam_auth) are configured "
+                "for Redis. Using Azure AD. Remove one to avoid misconfiguration."
+            )
+        elif _aws_iam_enabled:
+            if not _uses_tls(redis_kwargs):
+                raise ValueError("AWS ElastiCache IAM Redis authentication requires TLS")
+            verbose_logger.debug("Setting up AWS ElastiCache IAM authentication for Redis.")
+            redis_kwargs["credential_provider"] = _build_elasticache_iam_provider(redis_kwargs)
+
     redis_kwargs.pop("gcp_service_account", None)
     redis_kwargs.pop("gcp_ssl_ca_certs", None)
 
@@ -575,6 +638,8 @@ def _get_redis_client_logic(**env_overrides):
     redis_kwargs.pop("azure_client_id", None)
     redis_kwargs.pop("azure_tenant_id", None)
     redis_kwargs.pop("azure_client_secret", None)
+    for aws_iam_key in _AWS_IAM_KWARG_NAMES:
+        redis_kwargs.pop(aws_iam_key, None)
 
     if redis_kwargs.get("credential_provider") is not None:
         redis_kwargs.pop("redis_connect_func", None)
diff --git a/litellm/_redis_credential_provider.py b/litellm/_redis_credential_provider.py
index ba0398789a6..7d90f944657 100644
--- a/litellm/_redis_credential_provider.py
+++ b/litellm/_redis_credential_provider.py
@@ -1,10 +1,17 @@
+from __future__ import annotations
+
 import asyncio
 import threading
 import time
-from typing import Final, Protocol
+from collections.abc import Callable
+from typing import TYPE_CHECKING, Final, Protocol
+from urllib.parse import urlencode
 
 from redis.credentials import CredentialProvider
 
+if TYPE_CHECKING:
+    from botocore.credentials import Credentials
+
 # Azure AD scope for Redis Cache for Azure.
 AZURE_REDIS_SCOPE: Final = "https://redis.azure.com/.default"
 
@@ -117,6 +124,82 @@ class GCPIAMCredentialProvider(CredentialProvider):
         return (token,)
 
 
+_ELASTICACHE_SERVICE_NAME: Final = "elasticache"
+_ELASTICACHE_TOKEN_TTL_SECONDS: Final = 900
+_ELASTICACHE_SERVERLESS_RESOURCE_TYPE: Final = "ServerlessCache"
+
+
+class ElastiCacheIAMCredentialProvider(CredentialProvider):
+    def __init__(
+        self,
+        user_name: str,
+        cache_name: str,
+        region: str,
+        is_serverless: bool = False,
+        credentials_resolver: Callable[[], Credentials | None] | None = None,
+        token_lifetime_seconds: int = _ELASTICACHE_TOKEN_TTL_SECONDS,
+    ) -> None:
+        self._user_name = user_name
+        self._cache_name = cache_name.lower()
+        self._region = region
+        self._is_serverless = is_serverless
+        self._credentials_resolver = credentials_resolver or self._resolve_credentials
+        self._credentials: Credentials | None = None
+        self._token_lifetime_seconds = token_lifetime_seconds
+
+    @staticmethod
+    def _resolve_credentials() -> Credentials | None:
+        try:
+            import botocore.session
+        except ImportError as e:
+            raise ImportError(
+                "botocore is required for ElastiCache IAM Redis authentication. Install it with: pip install boto3"
+            ) from e
+
+        return botocore.session.get_session().get_credentials()
+
+    def _get_credentials(self) -> tuple[str, str]:
+        credentials: Final = self._credentials if self._credentials is not None else self._credentials_resolver()
+        if credentials is None:
+            raise RuntimeError("Unable to resolve AWS credentials for ElastiCache IAM Redis authentication")
+        self._credentials = credentials
+
+        frozen_credentials: Final = credentials.get_frozen_credentials()
+
+        try:
+            from botocore.auth import SigV4QueryAuth
+            from botocore.awsrequest import AWSRequest
+        except ImportError as e:
+            raise ImportError(
+                "botocore is required for ElastiCache IAM Redis authentication. Install it with: pip install boto3"
+            ) from e
+
+        query: Final = urlencode(
+            (
+                ("Action", "connect"),
+                ("User", self._user_name),
+                *((("ResourceType", _ELASTICACHE_SERVERLESS_RESOURCE_TYPE),) if self._is_serverless else ()),
+            )
+        )
+        request: Final = AWSRequest(method="GET", url=f"https://{self._cache_name}/?{query}")
+        SigV4QueryAuth(
+            frozen_credentials,
+            _ELASTICACHE_SERVICE_NAME,
+            self._region,
+            expires=self._token_lifetime_seconds,
+        ).add_auth(request)
+        signed_url: Final = request.url
+        if signed_url is None:
+            raise RuntimeError("Unable to generate AWS ElastiCache IAM credentials")
+        return self._user_name, signed_url.removeprefix("https://")
+
+    def get_credentials(self) -> tuple[str, str]:
+        return self._get_credentials()
+
+    async def get_credentials_async(self) -> tuple[str, str]:
+        return await asyncio.to_thread(self._get_credentials)
+
+
 class AzureADCredentialProvider(CredentialProvider):
     """
     redis.credentials.CredentialProvider implementation that supplies Azure AD
diff --git a/litellm/a2a_protocol/providers/bedrock_agentcore/handler.py b/litellm/a2a_protocol/providers/bedrock_agentcore/handler.py
index a4e6fa50901..306a8871b12 100644
--- a/litellm/a2a_protocol/providers/bedrock_agentcore/handler.py
+++ b/litellm/a2a_protocol/providers/bedrock_agentcore/handler.py
@@ -13,6 +13,7 @@ from litellm._logging import verbose_logger
 from litellm.a2a_protocol.providers.bedrock_agentcore.transformation import (
     BedrockAgentCoreA2ATransformation,
 )
+from litellm.llms.bedrock.base_aws_llm import run_aws_signing
 from litellm.llms.custom_httpx.http_handler import get_async_httpx_client
 from litellm.types.llms.custom_http import httpxSpecialProvider
 
@@ -45,7 +46,8 @@ class BedrockAgentCoreA2AHandler:
         Returns:
             A2A JSON-RPC response dict from the AgentCore agent
         """
-        url, headers, body = BedrockAgentCoreA2ATransformation.get_url_and_signed_request(
+        url, headers, body = await run_aws_signing(
+            BedrockAgentCoreA2ATransformation.get_url_and_signed_request,
             request_id=request_id,
             params=params,
             litellm_params=litellm_params,
@@ -91,7 +93,8 @@ class BedrockAgentCoreA2AHandler:
         Yields:
             A2A streaming response events from the AgentCore agent
         """
-        url, headers, body = BedrockAgentCoreA2ATransformation.get_url_and_signed_request(
+        url, headers, body = await run_aws_signing(
+            BedrockAgentCoreA2ATransformation.get_url_and_signed_request,
             request_id=request_id,
             params=params,
             litellm_params=litellm_params,
diff --git a/litellm/caching/caching.py b/litellm/caching/caching.py
index 884d095793c..d6dd2a073af 100644
--- a/litellm/caching/caching.py
+++ b/litellm/caching/caching.py
@@ -10,6 +10,7 @@
 import ast
 import hashlib
 import json
+import logging
 import time
 import traceback
 from collections.abc import Mapping
@@ -32,7 +33,7 @@ from .dual_cache import DualCache  # noqa: F401
 from .gcs_cache import GCSCache
 from .in_memory_cache import InMemoryCache
 from .qdrant_semantic_cache import QdrantSemanticCache
-from .redis_cache import RedisCache
+from .redis_cache import RedisCache, log_redis_failure
 from .redis_cluster_cache import RedisClusterCache
 from .redis_semantic_cache import RedisSemanticCache
 from .s3_cache import S3Cache
@@ -678,7 +679,7 @@ class Cache:
             cache_key, cached_data, kwargs = self._add_cache_logic(result=result, **kwargs)
             self.cache.set_cache(cache_key, cached_data, **kwargs)
         except Exception as e:
-            verbose_logger.exception("LiteLLM Cache: Excepton add_cache: %s", e)
+            log_redis_failure(verbose_logger, logging.ERROR, "LiteLLM Cache: exception in add_cache", e)
 
     async def async_add_cache(self, result, dynamic_cache_object: BaseCache | None = None, **kwargs):
         """
@@ -697,7 +698,7 @@ class Cache:
                 else:
                     await self.cache.async_set_cache(cache_key, cached_data, **kwargs)
         except Exception as e:
-            verbose_logger.exception("LiteLLM Cache: Excepton add_cache: %s", e)
+            log_redis_failure(verbose_logger, logging.ERROR, "LiteLLM Cache: exception in add_cache", e)
 
     def _convert_to_cached_embedding(
         self,
@@ -876,7 +877,7 @@ class Cache:
             else:
                 await self.cache.async_set_cache_pipeline(cache_list=cache_list, **kwargs)
         except Exception as e:
-            verbose_logger.exception("LiteLLM Cache: Excepton add_cache: %s", e)
+            log_redis_failure(verbose_logger, logging.ERROR, "LiteLLM Cache: exception in add_cache", e)
 
     def should_use_cache(self, **kwargs):
         """
diff --git a/litellm/caching/caching_handler.py b/litellm/caching/caching_handler.py
index 0de88eacaa5..139dcf058d2 100644
--- a/litellm/caching/caching_handler.py
+++ b/litellm/caching/caching_handler.py
@@ -1217,7 +1217,9 @@ class LLMCachingHandler:
         }
 
         if litellm.cache is not None:
-            litellm_params["preset_cache_key"] = litellm.cache._get_preset_cache_key_from_kwargs(**kwargs)
+            litellm_params["preset_cache_key"] = (
+                self.preset_cache_key or litellm.cache._get_preset_cache_key_from_kwargs(**kwargs)
+            )
         else:
             litellm_params["preset_cache_key"] = None
 
diff --git a/litellm/caching/dual_cache.py b/litellm/caching/dual_cache.py
index ec17cc1d809..be761e1258b 100644
--- a/litellm/caching/dual_cache.py
+++ b/litellm/caching/dual_cache.py
@@ -8,8 +8,8 @@ Has 4 primary methods:
     - async_get_cache
 """
 
+import logging
 import time
-import traceback
 from collections.abc import Sequence
 from threading import Lock
 from typing import TYPE_CHECKING, Any, Final
@@ -23,7 +23,7 @@ from litellm.constants import DEFAULT_MAX_REDIS_BATCH_CACHE_SIZE
 
 from .base_cache import BaseCache
 from .in_memory_cache import InMemoryCache
-from .redis_cache import RedisCache
+from .redis_cache import RedisCache, RedisCircuitBreakerOpenError, log_redis_failure
 
 if TYPE_CHECKING:
     from opentelemetry.trace import Span as _Span
@@ -177,8 +177,10 @@ class DualCache(BaseCache):
 
             print_verbose(f"get cache: cache result: {result}")
             return result
-        except Exception:
-            verbose_logger.error(traceback.format_exc())
+        except Exception as e:
+            log_redis_failure(
+                verbose_logger, logging.ERROR, "LiteLLM Cache: exception in get_cache", e, with_traceback=True
+            )
 
     def batch_get_cache(
         self,
@@ -204,9 +206,12 @@ class DualCache(BaseCache):
                 redis_result: Final = self.redis_cache.batch_get_cache(
                     key_list=sublist_keys, parent_otel_span=parent_otel_span
                 )
-            except Exception:
+            except Exception as e:
                 # Do not throttle subsequent callers if the Redis read fails.
                 self._rollback_redis_batch_key_reservations(previous_access_times)
+                if isinstance(e, RedisCircuitBreakerOpenError):
+                    verbose_logger.debug("LiteLLM Cache: batch_get_cache served from memory only: %s", e)
+                    return result
                 raise
 
             if self.in_memory_cache is not None:
@@ -217,8 +222,10 @@ class DualCache(BaseCache):
             return list(  # mutable-ok: public list contract
                 redis_result.get(key) if value is None else value for key, value in zip(keys, result)
             )
-        except Exception:
-            verbose_logger.error(traceback.format_exc())
+        except Exception as e:
+            log_redis_failure(
+                verbose_logger, logging.ERROR, "LiteLLM Cache: exception in batch_get_cache", e, with_traceback=True
+            )
 
     async def async_get_cache(
         self,
@@ -250,8 +257,10 @@ class DualCache(BaseCache):
 
             print_verbose(f"get cache: cache result: {result}")
             return result
-        except Exception:
-            verbose_logger.error(traceback.format_exc())
+        except Exception as e:
+            log_redis_failure(
+                verbose_logger, logging.ERROR, "LiteLLM Cache: exception in async_get_cache", e, with_traceback=True
+            )
 
     def _reserve_redis_batch_keys(
         self,
@@ -319,9 +328,12 @@ class DualCache(BaseCache):
                         redis_result: Final = await self.redis_cache.async_batch_get_cache(
                             sublist_keys, parent_otel_span=parent_otel_span
                         )
-                    except Exception:
+                    except Exception as e:
                         # Do not throttle subsequent callers if the Redis read fails.
                         self._rollback_redis_batch_key_reservations(previous_access_times)
+                        if isinstance(e, RedisCircuitBreakerOpenError):
+                            verbose_logger.debug("LiteLLM Cache: async_batch_get_cache served from memory only: %s", e)
+                            return result
                         raise
 
                     # Short-circuit if redis_result is None or contains only None values
@@ -339,8 +351,14 @@ class DualCache(BaseCache):
                             await self.in_memory_cache.async_set_cache(key, value, **self._backfill_kwargs(kwargs))
 
             return result
-        except Exception:
-            verbose_logger.error(traceback.format_exc())
+        except Exception as e:
+            log_redis_failure(
+                verbose_logger,
+                logging.ERROR,
+                "LiteLLM Cache: exception in async_batch_get_cache",
+                e,
+                with_traceback=True,
+            )
 
     async def async_set_cache(self, key, value, local_only: bool = False, **kwargs):
         print_verbose(f"async set cache: cache key: {key}; local_only: {local_only}; value: {value}")
@@ -353,7 +371,9 @@ class DualCache(BaseCache):
             if self.redis_cache is not None and local_only is False:
                 await self.redis_cache.async_set_cache(key, value, **kwargs)
         except Exception as e:
-            verbose_logger.exception("LiteLLM Cache: Excepton async add_cache: %s", e)
+            log_redis_failure(
+                verbose_logger, logging.ERROR, "LiteLLM Cache: exception in async add_cache", e, with_traceback=True
+            )
 
     # async_batch_set_cache
     async def async_set_cache_pipeline(self, cache_list: list, local_only: bool = False, **kwargs):
@@ -372,7 +392,9 @@ class DualCache(BaseCache):
                     cache_list=cache_list, ttl=kwargs.pop("ttl", None), **kwargs
                 )
         except Exception as e:
-            verbose_logger.exception("LiteLLM Cache: Excepton async add_cache: %s", e)
+            log_redis_failure(
+                verbose_logger, logging.ERROR, "LiteLLM Cache: exception in async add_cache", e, with_traceback=True
+            )
 
     async def async_increment_cache(
         self,
@@ -410,8 +432,10 @@ class DualCache(BaseCache):
 
             return result
         except Exception as e:
-            verbose_logger.warning(
-                "Redis async_increment_cache failed, falling back to in-memory result: %s",
+            log_redis_failure(
+                verbose_logger,
+                logging.WARNING,
+                "Redis async_increment_cache failed, falling back to in-memory result",
                 e,
             )
             return result
@@ -439,8 +463,10 @@ class DualCache(BaseCache):
 
             return result
         except Exception as e:
-            verbose_logger.warning(
-                "Redis async_increment_cache_pipeline failed, falling back to in-memory result: %s",
+            log_redis_failure(
+                verbose_logger,
+                logging.WARNING,
+                "Redis async_increment_cache_pipeline failed, falling back to in-memory result",
                 e,
             )
             return result
diff --git a/litellm/caching/redis_cache.py b/litellm/caching/redis_cache.py
index 106c1580110..2c36995c4f8 100644
--- a/litellm/caching/redis_cache.py
+++ b/litellm/caching/redis_cache.py
@@ -14,9 +14,11 @@ import functools
 import hashlib
 import inspect
 import json
+import logging
 import time
 from collections.abc import Awaitable, Callable, Sequence
 from contextvars import ContextVar
+from dataclasses import dataclass
 from datetime import timedelta
 from typing import TYPE_CHECKING, Any, Final, Protocol, TypeVar, cast
 
@@ -195,8 +197,14 @@ class RedisCircuitBreaker:
         self._timeout_streak_started_at: float | None = None
         self._opened_at: float | None = None
         self._state = self.CLOSED
+        self._generation = 0
         _breaker_metrics().record_state_change(None, self._state)
 
+    @property
+    def generation(self) -> int:
+        """Counts state transitions, so a call can tell whether the breaker moved while it ran."""
+        return self._generation
+
     def is_open(self) -> bool:
         """Returns True if Redis calls should be skipped."""
         if not self.enabled:
@@ -249,7 +257,7 @@ class RedisCircuitBreaker:
             self._set_state(self.OPEN)
 
     def record_success(self) -> None:
-        if not self.enabled:
+        if not self.enabled or self._state == self.OPEN:
             return
         if self._state == self.HALF_OPEN:
             verbose_logger.info("Redis circuit breaker CLOSED — Redis recovered")
@@ -265,6 +273,7 @@ class RedisCircuitBreaker:
         _breaker_metrics().record_transition(state)
         _breaker_metrics().record_state_change(self._state, state)
         self._state = state
+        self._generation += 1
 
 
 _RedisCallResult = TypeVar("_RedisCallResult")
@@ -391,21 +400,46 @@ def _record_swallowed_redis_failure(breaker: RedisCircuitBreaker, exc: BaseExcep
     _swallowed_redis_failures.set(_swallowed_redis_failures.get() + 1)
 
 
-def _enter_circuit_breaker(breaker: RedisCircuitBreaker, name: str) -> int:
-    """Reject the call if the breaker is open, else return the swallowed-failure count to compare against."""
+class RedisCircuitBreakerOpenError(Exception):
+    pass
+
+
+def log_redis_failure(
+    logger: logging.Logger, level: int, message: str, exc: BaseException, with_traceback: bool = False
+) -> None:
+    if isinstance(exc, RedisCircuitBreakerOpenError):
+        logger.debug("%s: %s", message, exc)
+        return
+    logger.log(level, "%s: %s", message, exc, exc_info=exc if with_traceback else None)
+
+
+@dataclass(frozen=True, slots=True)
+class _BreakerAdmission:
+    swallowed_before: int
+    generation: int
+
+
+def _enter_circuit_breaker(breaker: RedisCircuitBreaker, name: str) -> _BreakerAdmission:
+    """Reject the call if the breaker is open, else record what its success may later prove."""
     if breaker.is_open():
-        raise Exception(f"Redis circuit breaker is open — skipping {name}")
-    return _swallowed_redis_failures.get()
+        raise RedisCircuitBreakerOpenError(f"Redis circuit breaker is open — skipping {name}")
+    return _BreakerAdmission(swallowed_before=_swallowed_redis_failures.get(), generation=breaker.generation)
 
 
-def _exit_circuit_breaker(breaker: RedisCircuitBreaker, swallowed_before: int) -> None:
-    """Record success only when nothing failed while the call ran.
+def _exit_circuit_breaker(breaker: RedisCircuitBreaker, admission: _BreakerAdmission) -> None:
+    """Record success only when nothing failed while the call ran and the breaker has not moved since.
 
     Several Redis methods catch their own connection errors and return a default, so a
-    method that returned is not on its own proof of a healthy Redis.
+    method that returned is not on its own proof of a healthy Redis. A success also vouches
+    only for the breaker state that admitted the call: a call admitted before the breaker
+    opened, or a probe admitted before a later failure reopened it, finishes knowing nothing
+    about whether Redis has recovered since, so only the current probe may close the breaker.
     """
-    if _swallowed_redis_failures.get() == swallowed_before:
-        breaker.record_success()
+    if _swallowed_redis_failures.get() != admission.swallowed_before:
+        return
+    if breaker.generation != admission.generation:
+        return
+    breaker.record_success()
 
 
 async def _run_under_circuit_breaker(
@@ -418,14 +452,14 @@ async def _run_under_circuit_breaker(
     Shared by the method decorator and the Lua script executor so both feed the same
     health signal.
     """
-    swallowed_before: Final = _enter_circuit_breaker(breaker, name)
+    admission: Final = _enter_circuit_breaker(breaker, name)
     try:
         result: Final = await call()
     except Exception as e:
         if _is_redis_health_failure(e):
             breaker.record_failure(is_timeout=_is_redis_timeout_failure(e))
         raise
-    _exit_circuit_breaker(breaker, swallowed_before)
+    _exit_circuit_breaker(breaker, admission)
     return result
 
 
@@ -435,14 +469,14 @@ def _run_under_circuit_breaker_sync(
     call: Callable[[], _RedisCallResult],
 ) -> _RedisCallResult:
     """Run one blocking Redis call under a circuit breaker, feeding the same health signal as the async path."""
-    swallowed_before: Final = _enter_circuit_breaker(breaker, name)
+    admission: Final = _enter_circuit_breaker(breaker, name)
     try:
         result: Final = call()
     except Exception as e:
         if _is_redis_health_failure(e):
-            breaker.record_failure()
+            breaker.record_failure(is_timeout=_is_redis_timeout_failure(e))
         raise
-    _exit_circuit_breaker(breaker, swallowed_before)
+    _exit_circuit_breaker(breaker, admission)
     return result
 
 
@@ -1323,6 +1357,7 @@ class RedisCache(BaseCache):
         except Exception:
             return ast.literal_eval(decoded)
 
+    @_redis_circuit_breaker_guard_sync
     def get_cache(self, key, parent_otel_span: Span | None = None, **kwargs):
         try:
             key = self.check_and_fix_namespace(key=key)
@@ -1342,8 +1377,8 @@ class RedisCache(BaseCache):
             print_verbose(f"Got Redis Cache: key: {key}, cached_response {cached_response}")
             return self._get_cache_logic(cached_response=cached_response)
         except Exception as e:
-            # NON blocking - notify users Redis is throwing an exception
-            verbose_logger.error("litellm.caching.caching: get() - Got exception from REDIS: ", e)
+            verbose_logger.error("litellm.caching.caching: get() - Got exception from REDIS: %s", e)
+            _record_swallowed_redis_failure(self._circuit_breaker, e)
 
     def _run_redis_mget_operation(self, keys: list[str]) -> Sequence[bytes | str | None]:
         """
@@ -1380,12 +1415,12 @@ class RedisCache(BaseCache):
         key_value_dict = {}
         _key_list: Final = [key for key in key_list if key is not None]
         start_time: Final = time.time()
+        admission: Final = _enter_circuit_breaker(self._circuit_breaker, "batch_get_cache")
 
         try:
-            swallowed_before: Final = _enter_circuit_breaker(self._circuit_breaker, "batch_get_cache")
             _keys: Final = [self.check_and_fix_namespace(key=cache_key or "") for cache_key in _key_list]
             results: Final = self._run_redis_mget_operation(keys=_keys)
-            _exit_circuit_breaker(self._circuit_breaker, swallowed_before)
+            _exit_circuit_breaker(self._circuit_breaker, admission)
             end_time: Final = time.time()
             _duration: Final = end_time - start_time
             self.service_logger_obj.service_success_hook(
diff --git a/litellm/completion_extras/litellm_responses_transformation/transformation.py b/litellm/completion_extras/litellm_responses_transformation/transformation.py
index 4fe069b0b7d..5a6debc4af5 100644
--- a/litellm/completion_extras/litellm_responses_transformation/transformation.py
+++ b/litellm/completion_extras/litellm_responses_transformation/transformation.py
@@ -25,7 +25,7 @@ import litellm
 from litellm import ModelResponse
 from litellm._logging import verbose_logger
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
-    responses_reasoning_item_from_thinking_blocks,
+    responses_reasoning_items_from_thinking_blocks,
 )
 from litellm.llms.base_llm.base_model_iterator import BaseModelResponseIterator
 from litellm.llms.base_llm.bridges.completion_transformation import (
@@ -129,8 +129,8 @@ def _reasoning_input_items(msg: "AllMessageValues") -> list[dict[str, object]]:
         return stored
     raw_blocks: Final = msg.get("thinking_blocks") or ()
     blocks: Final = cast("Iterable[ChatCompletionThinkingBlock]", raw_blocks)  # cast-ok: untyped client json
-    from_thinking: Final = responses_reasoning_item_from_thinking_blocks(blocks)
-    return [] if from_thinking is None else [dict(from_thinking)]  # mutable-ok: API message payload
+    replayed: Final = responses_reasoning_items_from_thinking_blocks(blocks)
+    return [dict(item) for item in replayed]  # mutable-ok: API message payload
 
 
 def _build_reasoning_item(
@@ -227,7 +227,7 @@ class _ChatToolCallDict(ChatCompletionToolCallChunk, total=False):
     provider_specific_fields: Mapping[str, object]
 
 
-def _tool_call_dict_from_output_item(item: Mapping[str, Any], index: int) -> _ChatToolCallDict:
+def tool_call_dict_from_output_item(item: Mapping[str, Any], index: int) -> _ChatToolCallDict:
     """Convert a ``function_call`` or ``custom_tool_call`` output item dict to a chat
     completions tool_call dict. Custom (grammar/freeform) tool calls carry their raw
     string payload in ``input`` rather than ``arguments``; both map to
@@ -755,7 +755,7 @@ class LiteLLMResponsesTransformationHandler(CompletionTransformationBridge):
                     # Tool calls accumulate into the single trailing tool_calls choice
                     # like the typed branches above; a choice per call would hide every
                     # call after choices[0] from chat clients
-                    accumulated_tool_calls.append(_tool_call_dict_from_output_item(raw_item, tool_call_index))
+                    accumulated_tool_calls.append(tool_call_dict_from_output_item(raw_item, tool_call_index))
                     tool_call_index += 1
                 elif handle_raw_dict_callback is not None:
                     choice, index = handle_raw_dict_callback(item=raw_item, index=index)
@@ -1201,6 +1201,9 @@ class LiteLLMResponsesTransformationHandler(CompletionTransformationBridge):
         # Cast to Any to match the expected union type for tools list items
         tools.append(cast(Any, web_search_tool))
 
+    def transform_response_format_to_text_format(self, response_format: object) -> "ResponseText | None":
+        return self._transform_response_format_to_text_format(response_format)
+
     def _transform_response_format_to_text_format(self, response_format: object) -> "ResponseText | None":
         """
         Transform Chat Completion response_format parameter to Responses API text.format parameter.
@@ -1409,7 +1412,7 @@ class OpenAiResponsesToChatCompletionStreamIterator(BaseModelResponseIterator):
             # New output item added
             output_item = parsed_chunk.get("item", {})
             if output_item.get("type") in ("function_call", "custom_tool_call"):
-                converted: Final = _tool_call_dict_from_output_item(output_item, parsed_chunk.get("output_index", 0))
+                converted: Final = tool_call_dict_from_output_item(output_item, parsed_chunk.get("output_index", 0))
                 provider_specific_fields: Final = converted.get("provider_specific_fields")
 
                 function_chunk: Final = ChatCompletionToolCallFunctionChunk(
@@ -1484,7 +1487,7 @@ class OpenAiResponsesToChatCompletionStreamIterator(BaseModelResponseIterator):
                                 index=0,
                                 delta=Delta(
                                     tool_calls=(
-                                        _tool_call_dict_from_output_item(
+                                        tool_call_dict_from_output_item(
                                             output_item, parsed_chunk.get("output_index", 0)
                                         ),
                                     )
diff --git a/litellm/constants.py b/litellm/constants.py
index b2d90e20dbb..028c08a691e 100644
--- a/litellm/constants.py
+++ b/litellm/constants.py
@@ -143,6 +143,7 @@ DEFAULT_MCP_SEMANTIC_FILTER_SIMILARITY_THRESHOLD: Final = float(
     os.getenv("DEFAULT_MCP_SEMANTIC_FILTER_SIMILARITY_THRESHOLD", 0.3)
 )
 MAX_MCP_SEMANTIC_FILTER_TOOLS_HEADER_LENGTH: Final = int(os.getenv("MAX_MCP_SEMANTIC_FILTER_TOOLS_HEADER_LENGTH", 150))
+MAX_GUARDRAIL_SCAN_METADATA_HEADER_LENGTH: Final = 2048
 
 DEFAULT_AUTO_ROUTER_MAX_INPUT_CHARS: Final = 2000
 
@@ -197,6 +198,7 @@ LITELLM_UI_ALLOW_HEADERS: Final = [
     "x-litellm-adaptive-router-model",
     "x-litellm-applied-guardrails",
     "x-litellm-guardrail-scan-id",
+    "x-litellm-guardrail-scan-metadata",
     "x-litellm-cache-key",
 ]
 
@@ -333,6 +335,7 @@ DEFAULT_SSL_CIPHERS: Final = os.getenv(
 
 ########### v2 Architecture constants for managing writing updates to the database ###########
 REDIS_UPDATE_BUFFER_KEY: Final = "litellm_spend_update_buffer"
+REDIS_GATEWAY_REQUESTS_BUFFER_KEY: Final = "litellm_gateway_requests_buffer"
 REDIS_DAILY_SPEND_UPDATE_BUFFER_KEY: Final = "litellm_daily_spend_update_buffer"
 REDIS_DAILY_TEAM_SPEND_UPDATE_BUFFER_KEY: Final = "litellm_daily_team_spend_update_buffer"
 REDIS_DAILY_ORG_SPEND_UPDATE_BUFFER_KEY: Final = "litellm_daily_org_spend_update_buffer"
@@ -395,6 +398,18 @@ TIKTOKEN_ENCODE_CHUNK_SIZE_CHARS: Final = get_env_int_in_range(
     minimum=1,
     maximum=TIKTOKEN_ENCODE_MAX_CHUNK_SIZE_CHARS,
 )
+TOKEN_COUNTER_MAX_EXACT_CHARS: Final = get_env_int_in_range(
+    "TOKEN_COUNTER_MAX_EXACT_CHARS",
+    default=4_000_000,
+    minimum=1,
+    maximum=1_000_000_000,
+)
+TOKEN_COUNTER_MAX_CONCURRENT_COUNTS: Final = get_env_int_in_range(
+    "TOKEN_COUNTER_MAX_CONCURRENT_COUNTS",
+    default=4,
+    minimum=1,
+    maximum=256,
+)
 MAX_TILE_WIDTH: Final = int(os.getenv("MAX_TILE_WIDTH", 512))
 MAX_TILE_HEIGHT: Final = int(os.getenv("MAX_TILE_HEIGHT", 512))
 OPENAI_FILE_SEARCH_COST_PER_1K_CALLS: Final = float(os.getenv("OPENAI_FILE_SEARCH_COST_PER_1K_CALLS", 2.5 / 1000))
@@ -567,6 +582,7 @@ LOGGING_WORKER_AGGRESSIVE_CLEAR_COOLDOWN_SECONDS: Final = float(
 LOGGING_EXECUTOR_MAX_THREADS: Final = get_env_int("LOGGING_EXECUTOR_MAX_THREADS", 100)
 LOGGING_EXECUTOR_MAX_PENDING_TASKS: Final = get_env_int("LOGGING_EXECUTOR_MAX_PENDING_TASKS", 10_000)
 LOGGING_EXECUTOR_DROPPED_TASK_LOG_INTERVAL_SECONDS: Final = 30.0
+AWS_SIGNING_MAX_THREADS: Final = 16
 DD_TRACER_STREAMING_CHUNK_YIELD_RESOURCE: Final = os.getenv(
     "DD_TRACER_STREAMING_CHUNK_YIELD_RESOURCE", "streaming.chunk.yield"
 )
@@ -1638,6 +1654,7 @@ CLOUDZERO_EXPORT_USAGE_DATA_JOB_NAME: Final = "cloudzero_export_usage_data"
 MAVVRIK_FOCUS_EXPORT_JOB_NAME: Final = "mavvrik_focus_export_usage_data"
 CLOUDZERO_MAX_FETCHED_DATA_RECORDS: Final = int(os.getenv("CLOUDZERO_MAX_FETCHED_DATA_RECORDS", 50000))
 SPEND_LOG_CLEANUP_JOB_NAME: Final = "spend_log_cleanup"
+BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME: Final = "background_health_check_db_save"
 KEY_ROTATION_JOB_NAME: Final = "litellm_key_rotation_job"
 EXPIRED_UI_SESSION_KEY_CLEANUP_JOB_NAME: Final = "litellm_expired_ui_session_key_cleanup_job"
 WEEKLY_SPEND_REPORT_JOB_ID: Final = "weekly_spend_report_job"
@@ -1666,6 +1683,7 @@ SPEND_LOG_QUEUE_POLL_INTERVAL: Final = float(os.getenv("SPEND_LOG_QUEUE_POLL_INT
 RESPONSES_SESSION_LOOKUP_MAX_ATTEMPTS: Final = max(1, int(os.getenv("RESPONSES_SESSION_LOOKUP_MAX_ATTEMPTS", "3")))
 RESPONSES_SESSION_LOOKUP_RETRY_INTERVAL: Final = float(os.getenv("RESPONSES_SESSION_LOOKUP_RETRY_INTERVAL", "0.2"))
 SPEND_COUNTER_RESEED_LOCKS_MAX_SIZE: Final = int(os.getenv("SPEND_COUNTER_RESEED_LOCKS_MAX_SIZE", 10000))
+PROXY_DB_LOOKUP_MAX_CONCURRENCY: Final = max(1, int(os.getenv("PROXY_DB_LOOKUP_MAX_CONCURRENCY", "25")))
 DEFAULT_CRON_JOB_LOCK_TTL_SECONDS: Final = int(os.getenv("DEFAULT_CRON_JOB_LOCK_TTL_SECONDS", 60))  # 1 minute
 PROXY_BUDGET_RESCHEDULER_MIN_TIME: Final = int(os.getenv("PROXY_BUDGET_RESCHEDULER_MIN_TIME", 597))
 RESET_BUDGET_JOB_BATCH_SIZE: Final = max(1, int(os.getenv("RESET_BUDGET_JOB_BATCH_SIZE", "500")))
@@ -1767,6 +1785,10 @@ LITELLM_SETTINGS_SAFE_DB_OVERRIDES: Final = [
 SPECIAL_LITELLM_AUTH_TOKEN: Final = ["ui-token"]
 DEFAULT_MANAGEMENT_OBJECT_IN_MEMORY_CACHE_TTL = int(os.getenv("DEFAULT_MANAGEMENT_OBJECT_IN_MEMORY_CACHE_TTL", 60))
 DEFAULT_ACCESS_GROUP_CACHE_TTL: Final = int(os.getenv("DEFAULT_ACCESS_GROUP_CACHE_TTL", 600))
+SPEND_LOG_KEY_METADATA_CACHE_TTL: Final = 600
+SPEND_LOG_KEY_METADATA_MISS_CACHE_TTL: Final = 30
+SPEND_LOG_KEY_METADATA_CACHE_MAX_ITEMS: Final = 10000
+SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS: Final = 5000
 # Short TTL for negative MCP access-group existence lookups. Keeps unauthenticated
 # callers from forcing a DB query per request for unknown names, while bounding
 # staleness so a transient DB error (which surfaces as an empty list) cannot
@@ -1978,6 +2000,9 @@ NON_INFERENCE_CALL_TYPES: Final[frozenset[str]] = frozenset(
     }
 )
 
+UNKNOWN_MODEL_SPEND_LOG_MODEL: Final[str] = "unknown-model"
+MAX_SPEND_LOG_MODEL_NAME_LENGTH: Final[int] = 256
+
 # PTU reservation rollup writes rows to LiteLLM_DailyTeamSpend with this
 # sentinel api_key so PTU flat cost stays distinguishable from real per-request
 # spend under the table's composite unique constraint.
diff --git a/litellm/cost_calculator.py b/litellm/cost_calculator.py
index c9c7df4d75e..814eaaf76f7 100644
--- a/litellm/cost_calculator.py
+++ b/litellm/cost_calculator.py
@@ -25,6 +25,7 @@ from litellm.litellm_core_utils.llm_cost_calc.usage_object_transformation import
     TranscriptionUsageObjectTransformation,
 )
 from litellm.litellm_core_utils.llm_cost_calc.utils import (
+    BilledTokenRates,
     CostCalculatorUtils,
     _generic_cost_per_character,
     _get_regional_uplift_multiplier,
@@ -45,6 +46,9 @@ from litellm.llms.azure.cost_calculation import (
 from litellm.llms.azure_ai.cost_calculator import (
     cost_per_token as azure_ai_cost_per_token,
 )
+from litellm.llms.azure_ai.cost_calculator import (
+    is_azure_model_router as azure_ai_is_model_router_name,
+)
 from litellm.llms.base_llm.search.transformation import SearchResponse
 from litellm.llms.bedrock.cost_calculation import (
     cost_per_token as bedrock_cost_per_token,
@@ -1122,6 +1126,7 @@ def _store_cost_breakdown_in_logging_obj(
     service_tier: str | None = None,
     data_residency: str | None = None,
     vertex_location: str | None = None,
+    billed_token_rates: BilledTokenRates | None = None,
 ) -> None:
     """
     Helper function to store cost breakdown in the logging object.
@@ -1166,6 +1171,7 @@ def _store_cost_breakdown_in_logging_obj(
             service_tier=service_tier,
             data_residency=data_residency,
             vertex_location=vertex_location,
+            billed_token_rates=billed_token_rates,
         )
 
     except Exception as breakdown_error:
@@ -1659,11 +1665,10 @@ def completion_cost(
                     data_residency=data_residency,
                     vertex_location=vertex_location,
                     response=completion_response,
-                    request_model=request_model_for_cost,
                 )
 
                 # Get additional costs from provider (e.g., routing fees, infrastructure costs)
-                if custom_llm_provider == "azure_ai":
+                if custom_llm_provider == "azure_ai" and not azure_ai_is_model_router_name(model):
                     model_for_additional_costs = request_model_for_cost
                     if completion_response is not None:
                         hidden_params = getattr(completion_response, "_hidden_params", None) or {}
@@ -1735,6 +1740,7 @@ def completion_cost(
                     _reasoning_cost: float | None = None
                     _cache_read_cost: float | None = None
                     _cache_creation_cost: float | None = None
+                    _billed_token_rates: BilledTokenRates | None = None
                     if cost_per_token_usage_object is not None and model:
                         _breakdown_provider: str | None = (
                             custom_llm_provider if isinstance(custom_llm_provider, str) else None
@@ -1746,10 +1752,12 @@ def completion_cost(
                             service_tier=service_tier,
                             data_residency=data_residency,
                             vertex_location=vertex_location,
+                            custom_cost_per_token=custom_cost_per_token,
                         )
                         _reasoning_cost = _token_type_breakdown.reasoning_cost
                         _cache_read_cost = _token_type_breakdown.cache_read_cost
                         _cache_creation_cost = _token_type_breakdown.cache_creation_cost
+                        _billed_token_rates = _token_type_breakdown.rates
                     _store_cost_breakdown_in_logging_obj(
                         litellm_logging_obj=litellm_logging_obj,
                         prompt_tokens_cost_usd_dollar=prompt_tokens_cost_usd_dollar,
@@ -1769,6 +1777,7 @@ def completion_cost(
                         service_tier=service_tier,
                         data_residency=data_residency,
                         vertex_location=vertex_location,
+                        billed_token_rates=_billed_token_rates,
                     )
 
                 return _final_cost
diff --git a/litellm/experimental_mcp_client/client.py b/litellm/experimental_mcp_client/client.py
index 23bcc3b5242..6cecc1e6157 100644
--- a/litellm/experimental_mcp_client/client.py
+++ b/litellm/experimental_mcp_client/client.py
@@ -19,6 +19,7 @@ from mcp import ClientSession, McpError, ReadResourceResult, Resource, StdioServ
 from mcp.client.sse import sse_client
 from mcp.client.stdio import stdio_client
 from mcp.shared.message import SessionMessage
+from mcp.shared.session import RequestResponder
 from typing_extensions import Unpack
 
 _TransportStreams: TypeAlias = tuple[
@@ -54,15 +55,22 @@ def missing_streamable_http_client_error() -> ImportError:
     )
 
 
-from mcp.types import CallToolRequestParams as MCPCallToolRequestParams
-from mcp.types import CallToolResult as MCPCallToolResult
 from mcp.types import (
+    METHOD_NOT_FOUND,
+    ClientResult,
     GetPromptRequestParams,
     GetPromptResult,
+    ListPromptsResult,
+    ListResourcesResult,
+    ListResourceTemplatesResult,
     Prompt,
     ResourceTemplate,
+    ServerNotification,
+    ServerRequest,
     TextContent,
 )
+from mcp.types import CallToolRequestParams as MCPCallToolRequestParams
+from mcp.types import CallToolResult as MCPCallToolResult
 from mcp.types import Tool as MCPTool
 from pydantic import AnyUrl
 
@@ -148,8 +156,8 @@ _SDK_READ_TIMEOUT_CODE: Final = int(httpx.codes.REQUEST_TIMEOUT)
 otherwise carries JSON-RPC error codes."""
 
 
-def _as_read_timeout(exc: BaseException) -> TimeoutError | None:
-    """The session read timeout elapsing, re-expressed as a ``TimeoutError``, or ``None``.
+def as_mcp_read_timeout(exc: BaseException) -> TimeoutError | None:
+    """Normalize an MCP SDK read timeout for client and gateway diagnostics, or return ``None``.
 
     The SDK reports its own elapsed read timeout as ``McpError`` carrying an HTTP status code in a
     field that otherwise holds JSON-RPC error codes, and it relays an upstream's JSON-RPC error
@@ -444,6 +452,18 @@ class MCPClient:
         in_flight_error: BaseException | None = None
         try:
             read_stream, write_stream = transport[0], transport[1]
+            stream_error: Final[asyncio.Future[Exception]] = asyncio.get_running_loop().create_future()
+
+            async def receive_message(
+                message: RequestResponder[ServerRequest, ClientResult] | ServerNotification | Exception,
+            ) -> None:
+                if not isinstance(message, (ValueError, httpx.RequestError, OSError)):
+                    return
+                if not stream_error.done():
+                    stream_error.set_result(message)
+                # The SDK closes pending requests when its message handler raises.
+                raise RuntimeError("MCP response stream failed")
+
             # Build session kwargs with optional callbacks
             session_kwargs: Final[dict[str, Any]] = {}
             if self._sampling_callback is not None:
@@ -458,6 +478,7 @@ class MCPClient:
                 read_stream,
                 write_stream,
                 read_timeout_seconds=timedelta(seconds=self.timeout),
+                message_handler=receive_message,
                 **session_kwargs,
             )
             session: Final = await session_ctx.__aenter__()
@@ -469,6 +490,10 @@ class MCPClient:
                     if isinstance(ins, str) and ins.strip():
                         self._last_initialize_instructions = ins.strip()
                 return await operation(session)
+            except McpError:
+                if stream_error.done():
+                    raise stream_error.result()
+                raise
             finally:
                 try:
                     await session_ctx.__aexit__(None, None, None)
@@ -503,11 +528,10 @@ class MCPClient:
             transport_ctx, http_client = self._create_transport_context()
             return await self._execute_session_operation(transport_ctx, operation)
         except Exception as e:
-            read_timeout: Final = _as_read_timeout(e)
+            read_timeout: Final = as_mcp_read_timeout(e)
             if read_timeout is not None:
                 verbose_logger.warning(
-                    "MCP client timed out after %ss waiting for %s to answer; the server accepted the "
-                    "request and ended its response stream without a JSON-RPC reply",
+                    "MCP client timed out after %ss waiting for a valid MCP response from %s",
                     self.timeout,
                     self.server_url or "stdio",
                 )
@@ -761,8 +785,19 @@ class MCPClient:
         """List available prompts from the server."""
         verbose_logger.debug("MCP client listing tools from %s", self.server_url or "stdio")
 
-        async def _list_prompts_operation(session: ClientSession):
-            return await session.list_prompts()
+        async def _list_prompts_operation(session: ClientSession) -> ListPromptsResult:
+            capabilities: Final = session.get_server_capabilities()
+            if capabilities is not None and capabilities.prompts is None:
+                return ListPromptsResult(prompts=[])
+            try:
+                return await session.list_prompts()
+            except McpError as error:
+                if error.error.code != METHOD_NOT_FOUND:
+                    raise
+                verbose_logger.debug(
+                    "MCP client list_prompts is unsupported by %s: %s", self.server_url or "stdio", error
+                )
+                return ListPromptsResult(prompts=[])
 
         try:
             result: Final = await self.run_with_session(_list_prompts_operation)
@@ -838,8 +873,19 @@ class MCPClient:
         """List available resources from the server."""
         verbose_logger.debug("MCP client listing resources from %s", self.server_url or "stdio")
 
-        async def _list_resources_operation(session: ClientSession):
-            return await session.list_resources()
+        async def _list_resources_operation(session: ClientSession) -> ListResourcesResult:
+            capabilities: Final = session.get_server_capabilities()
+            if capabilities is not None and capabilities.resources is None:
+                return ListResourcesResult(resources=[])
+            try:
+                return await session.list_resources()
+            except McpError as error:
+                if error.error.code != METHOD_NOT_FOUND:
+                    raise
+                verbose_logger.debug(
+                    "MCP client list_resources is unsupported by %s: %s", self.server_url or "stdio", error
+                )
+                return ListResourcesResult(resources=[])
 
         try:
             result: Final = await self.run_with_session(_list_resources_operation)
@@ -874,8 +920,19 @@ class MCPClient:
         """List available resource templates from the server."""
         verbose_logger.debug("MCP client listing resource templates from %s", self.server_url or "stdio")
 
-        async def _list_resource_templates_operation(session: ClientSession):
-            return await session.list_resource_templates()
+        async def _list_resource_templates_operation(session: ClientSession) -> ListResourceTemplatesResult:
+            capabilities: Final = session.get_server_capabilities()
+            if capabilities is not None and capabilities.resources is None:
+                return ListResourceTemplatesResult(resourceTemplates=[])
+            try:
+                return await session.list_resource_templates()
+            except McpError as error:
+                if error.error.code != METHOD_NOT_FOUND:
+                    raise
+                verbose_logger.debug(
+                    "MCP client list_resource_templates is unsupported by %s: %s", self.server_url or "stdio", error
+                )
+                return ListResourceTemplatesResult(resourceTemplates=[])
 
         try:
             result: Final = await self.run_with_session(_list_resource_templates_operation)
diff --git a/litellm/files/main.py b/litellm/files/main.py
index 19da77b7364..218518eb3cd 100644
--- a/litellm/files/main.py
+++ b/litellm/files/main.py
@@ -31,7 +31,7 @@ FileCreateProvider = Literal[
 FileRetrieveProvider = Literal[
     "openai", "azure", "gemini", "vertex_ai", "hosted_vllm", "litellm_proxy", "manus", "anthropic"
 ]
-FileDeleteProvider = Literal["openai", "azure", "gemini", "litellm_proxy", "manus", "anthropic"]
+FileDeleteProvider = Literal["openai", "azure", "gemini", "bedrock", "litellm_proxy", "manus", "anthropic"]
 FileListProvider = Literal["openai", "azure", "litellm_proxy", "manus", "anthropic"]
 import litellm
 from litellm import get_secret_str
diff --git a/litellm/integrations/azure_sentinel/azure_sentinel.py b/litellm/integrations/azure_sentinel/azure_sentinel.py
index eba6c862f7a..db5f790615f 100644
--- a/litellm/integrations/azure_sentinel/azure_sentinel.py
+++ b/litellm/integrations/azure_sentinel/azure_sentinel.py
@@ -21,6 +21,8 @@ from types import MappingProxyType
 from typing import Final, TypeVar
 from urllib.parse import urlparse
 
+import httpx
+
 from litellm._logging import verbose_logger
 from litellm.integrations.batch_utils import (
     BatchSendCancelled,
@@ -418,7 +420,7 @@ class AzureSentinelLogger(CustomBatchLogger):
             "Content-Type": "application/json",
         }
 
-        async def _send_batch(batch: Sequence[_QueuedPayload]):
+        async def _send_batch(batch: Sequence[_QueuedPayload]) -> httpx.Response:
             body: Final = safe_dumps(batch)
             return await self.async_httpx_client.post(
                 url=api_endpoint,
diff --git a/litellm/integrations/callback_configs.json b/litellm/integrations/callback_configs.json
index c40b90cee25..85bfcc6e7ed 100644
--- a/litellm/integrations/callback_configs.json
+++ b/litellm/integrations/callback_configs.json
@@ -378,6 +378,27 @@
     },
     "description": "OpenTelemetry Logging Integration"
   },
+  {
+    "id": "pointfive",
+    "displayName": "PointFive",
+    "logo": "pointfive.png",
+    "supports_key_team_logging": false,
+    "dynamic_params": {
+      "POINTFIVE_API_KEY": {
+        "type": "password",
+        "ui_name": "API Key",
+        "description": "PointFive API key, used to request an upload url for each batch of logs",
+        "required": true
+      },
+      "POINTFIVE_API_URL": {
+        "type": "text",
+        "ui_name": "API URL",
+        "description": "PointFive API endpoint. Leave blank to use https://api.pointfive.co/api/v1/ingestion",
+        "required": false
+      }
+    },
+    "description": "PointFive Logging Integration"
+  },
   {
     "id": "s3",
     "displayName": "S3",
diff --git a/litellm/integrations/custom_guardrail.py b/litellm/integrations/custom_guardrail.py
index 37d6a7e793d..77bf4820a1a 100644
--- a/litellm/integrations/custom_guardrail.py
+++ b/litellm/integrations/custom_guardrail.py
@@ -850,20 +850,24 @@ class CustomGuardrail(CustomLogger):
         if self.should_run_guardrail(data=request_data, event_type=GuardrailEventHooks.post_call) is not True:
             return None
 
-        # CHECK IF GUARDRAIL REJECTS THE REQUEST
         target: Final = self._deployment_hook_target()
-        hook_request_data: Final = {**request_data, "guardrail_to_apply": self} if target is not self else request_data
-        result: Final = await target.async_post_call_success_hook(
-            user_api_key_dict=UserAPIKeyAuth(
-                user_id=request_data.get("user_api_key_user_id"),
-                team_id=request_data.get("user_api_key_team_id"),
-                end_user_id=request_data.get("user_api_key_end_user_id"),
-                api_key=request_data.get("user_api_key_hash"),
-                request_route=request_data.get("user_api_key_request_route"),
-            ),
-            data=hook_request_data,
-            response=response,
-        )
+        try:
+            if target is not self:
+                request_data["guardrail_to_apply"] = self  # rebind-ok: dispatch consumes this key
+            result: Final = await target.async_post_call_success_hook(
+                user_api_key_dict=UserAPIKeyAuth(
+                    user_id=request_data.get("user_api_key_user_id"),
+                    team_id=request_data.get("user_api_key_team_id"),
+                    end_user_id=request_data.get("user_api_key_end_user_id"),
+                    api_key=request_data.get("user_api_key_hash"),
+                    request_route=request_data.get("user_api_key_request_route"),
+                ),
+                data=request_data,
+                response=response,
+            )
+        finally:
+            if target is not self:
+                request_data.pop("guardrail_to_apply", None)
 
         if not self._is_valid_response_type(result):
             return None
diff --git a/litellm/integrations/custom_logger.py b/litellm/integrations/custom_logger.py
index 8f03e08f02d..d445a3adf14 100644
--- a/litellm/integrations/custom_logger.py
+++ b/litellm/integrations/custom_logger.py
@@ -3,12 +3,13 @@
 import re
 import traceback
 from collections.abc import AsyncGenerator, Mapping, Sequence
+from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, ClassVar, Final, Optional
 
 from pydantic import BaseModel
 
 from litellm._logging import verbose_logger
-from litellm.constants import DEFAULT_MAX_RECURSE_DEPTH_SENSITIVE_DATA_MASKER
+from litellm.constants import DEFAULT_MAX_RECURSE_DEPTH_SENSITIVE_DATA_MASKER, EMPTY_MAPPING
 from litellm.types.integrations.argilla import ArgillaItem
 from litellm.types.integrations.custom_logger import AgenticLoopPlan
 from litellm.types.llms.openai import AllMessageValues, ChatCompletionRequest
@@ -897,10 +898,9 @@ class CustomLogger:  # https://docs.litellm.ai/docs/observability/custom_callbac
 
         This is useful for logging payloads that contain sensitive information.
         """
-        from copy import copy
-
         import litellm
         from litellm import Choices, Message, ModelResponse
+        from litellm.litellm_core_utils.classifier_logging import CLASSIFIER_AUDIT_FIELDS, without_classifier_audit
 
         turn_off_message_logging: Final[bool] = getattr(self, "turn_off_message_logging", False)
         excluded_fields: Final[list[str] | None] = getattr(litellm, "standard_logging_payload_excluded_fields", None)
@@ -909,30 +909,25 @@ class CustomLogger:  # https://docs.litellm.ai/docs/observability/custom_callbac
         if turn_off_message_logging is False and not excluded_fields:
             return model_call_details
 
-        # Only make a shallow copy of the top-level dict to avoid deepcopy issues
-        # with complex objects like AuthenticationError that may be present
-        model_call_details_copy: Final = copy(model_call_details)
         standard_logging_object: Final = model_call_details.get("standard_logging_object")
         if standard_logging_object is None:
-            return model_call_details_copy
+            return model_call_details.copy()
 
         # Make a copy of just the standard_logging_object to avoid modifying the original
-        standard_logging_object_copy: Final = copy(standard_logging_object)
-
-        # Handle excluded fields - remove them entirely from the payload
-        if excluded_fields:
-            for field in excluded_fields:
-                if field in standard_logging_object_copy:
-                    del standard_logging_object_copy[field]
+        standard_logging_object_copy: Final = {
+            key: value
+            for key, value in standard_logging_object.items()
+            if key not in (excluded_fields or ()) and not (turn_off_message_logging and key in CLASSIFIER_AUDIT_FIELDS)
+        }
 
         # Handle turn_off_message_logging - redact messages and responses (if not already excluded)
         if turn_off_message_logging:
             redacted_str: Final = "redacted-by-litellm"
 
-            if "messages" not in (excluded_fields or []) and standard_logging_object_copy.get("messages") is not None:
+            if "messages" not in (excluded_fields or ()) and standard_logging_object_copy.get("messages") is not None:
                 standard_logging_object_copy["messages"] = [Message(content=redacted_str).model_dump()]
 
-            if "response" not in (excluded_fields or []) and standard_logging_object_copy.get("response") is not None:
+            if "response" not in (excluded_fields or ()) and standard_logging_object_copy.get("response") is not None:
                 response: Final = standard_logging_object_copy["response"]
                 # Check if this is a ResponsesAPIResponse (has "output" field)
                 if isinstance(response, dict) and "output" in response:
@@ -956,8 +951,18 @@ class CustomLogger:  # https://docs.litellm.ai/docs/observability/custom_callbac
                     model_response_dict: Final = model_response.model_dump()
                     standard_logging_object_copy["response"] = model_response_dict
 
-        model_call_details_copy["standard_logging_object"] = standard_logging_object_copy
-        return model_call_details_copy
+        params: Final = model_call_details.get("litellm_params")
+        request: Final = params.get("proxy_server_request") if isinstance(params, dict) else None
+        redacted_params: Final = (
+            MappingProxyType({"litellm_params": {**params, "proxy_server_request": without_classifier_audit(request)}})
+            if turn_off_message_logging and isinstance(params, dict) and isinstance(request, dict)
+            else EMPTY_MAPPING
+        )
+        return {
+            **model_call_details,
+            **redacted_params,
+            "standard_logging_object": standard_logging_object_copy,
+        }
 
     async def get_proxy_server_request_from_cold_storage_with_object_key(
         self,
diff --git a/litellm/integrations/langfuse/langfuse.py b/litellm/integrations/langfuse/langfuse.py
index 9576eabaa34..b75369965de 100644
--- a/litellm/integrations/langfuse/langfuse.py
+++ b/litellm/integrations/langfuse/langfuse.py
@@ -2,6 +2,7 @@
 #    On success, logs events to Langfuse
 import inspect
 import os
+import re
 import traceback
 from collections.abc import Callable, Iterable, Mapping
 from datetime import datetime
@@ -63,6 +64,44 @@ def _object_mapping(value: object) -> Mapping[str, object] | None:
     return value if isinstance(value, dict) else None
 
 
+def _widened_items(mapping: Mapping[str, object]) -> Iterable[tuple[object, object]]:
+    """Header pairs with the key type widened back to what a caller-supplied dict can actually hold."""
+    return mapping.items()
+
+
+def _is_session_header_trace(trace_id: object, session_id: object, proxy_server_request: object) -> bool:
+    if not isinstance(trace_id, str) or not isinstance(session_id, str):
+        return False
+    request: Final = _object_mapping(proxy_server_request)
+    raw_headers: Final = _object_mapping(request.get("headers")) if request is not None else None
+    if raw_headers is None:
+        return False
+    headers: Final = MappingProxyType(
+        {key.lower(): value for key, value in _widened_items(raw_headers) if isinstance(key, str)}
+    )
+    if headers.get("x-litellm-trace-id"):
+        return False
+    if headers.get("langfuse_trace_id") is not None:
+        return False
+    if trace_id != session_id and headers.get("langfuse_session_id") != session_id:
+        return False
+    if headers.get("x-litellm-session-id") == trace_id:
+        return True
+    if re.fullmatch(r"[a-zA-Z0-9_\-]{8,}", trace_id) is None:
+        return False
+    user_agent: Final = headers.get("user-agent")
+    codex: Final = isinstance(user_agent, str) and re.match(r"^codex[-_ /]", user_agent, re.IGNORECASE) is not None
+    return any(
+        value == trace_id
+        and (
+            key == "x-session-id"
+            or re.fullmatch(r"x-.+-session-id", key) is not None
+            or (codex and key in ("session-id", "session_id", "thread-id", "conversation_id"))
+        )
+        for key, value in headers.items()
+    )
+
+
 class _UsageObject(Protocol):
     """Token-count surface the Langfuse logger reads off a response usage payload."""
 
@@ -609,6 +648,18 @@ class LangFuseLogger:
             # This allows continuing an existing trace while still returning the correct trace_id
             if existing_trace_id is not None:
                 trace_id = existing_trace_id
+            resolved_trace_id: Final = (
+                litellm_call_id or trace_id
+                if existing_trace_id is None
+                and _is_session_header_trace(trace_id, session_id, litellm_params.get("proxy_server_request"))
+                else trace_id
+            )
+            if resolved_trace_id != trace_id:
+                verbose_logger.debug(
+                    "Langfuse: trace_id %s came from a session header; using call id %s so each call gets its own trace",
+                    trace_id,
+                    resolved_trace_id,
+                )
             requested_trace_keys: Final = _as_steering_key_sequence(clean_metadata.pop("update_trace_keys", ()))
             update_trace_keys: Final = (
                 requested_trace_keys if _as_steering_flag(litellm.langfuse_enable_update_trace_keys) else ()
@@ -663,7 +714,7 @@ class LangFuseLogger:
                     trace_params["output"] = masked_output if not mask_output else "redacted-by-litellm"
             else:  # don't overwrite an existing trace
                 trace_params = {
-                    "id": trace_id,
+                    "id": resolved_trace_id,
                     "name": trace_name,
                     "session_id": session_id,
                     "input": masked_input if not mask_input else "redacted-by-litellm",
@@ -845,13 +896,13 @@ class LangFuseLogger:
             # Verify langfuse accepted our trace_id; if it differs, log a warning but still return our intended value
             # to match expected test behavior
             if hasattr(generation_client, "trace_id") and generation_client.trace_id:
-                if generation_client.trace_id != trace_id:
+                if generation_client.trace_id != resolved_trace_id:
                     verbose_logger.warning(
                         "Langfuse trace_id mismatch: set %s, but langfuse returned %s. Using our intended trace_id for consistency.",
-                        trace_id,
+                        resolved_trace_id,
                         generation_client.trace_id,
                     )
-            return trace_id, generation_id
+            return resolved_trace_id, generation_id
         except Exception:
             verbose_logger.error("Langfuse Layer Error - %s", traceback.format_exc())
             return None, None
diff --git a/litellm/integrations/newrelic/newrelic_metrics.py b/litellm/integrations/newrelic/newrelic_metrics.py
index 25dbfc2bdb2..da952b78d3f 100644
--- a/litellm/integrations/newrelic/newrelic_metrics.py
+++ b/litellm/integrations/newrelic/newrelic_metrics.py
@@ -5,8 +5,9 @@ NR Reference API: https://docs.newrelic.com/docs/data-apis/ingest-apis/metric-ap
 
 `async_log_success_event` / `async_log_failure_event` queue one record per request;
 at flush the queue is aggregated by (team, model group, model, provider, status)
-into count/summary metrics. `interval.ms` is the real window between flushes,
-computed at flush time.
+into count/summary metrics, plus one max/remaining budget gauge pair per team
+taken from the team's latest record. `interval.ms` is the real window between
+flushes, computed at flush time.
 
 Team-scoped by construction: the ingest key is injected explicitly and there is
 deliberately no environment-variable fallback, so a team's metrics are never sent
@@ -47,11 +48,14 @@ from litellm.types.integrations.newrelic import (
     NEWRELIC_METRIC_PROMPT_TOKENS,
     NEWRELIC_METRIC_REQUEST_DURATION_MS,
     NEWRELIC_METRIC_REQUESTS,
+    NEWRELIC_METRIC_TEAM_MAX_BUDGET,
+    NEWRELIC_METRIC_TEAM_REMAINING_BUDGET,
     NEWRELIC_METRIC_TOTAL_TOKENS,
     NEWRELIC_METRICS_MAX_BATCH_SIZE,
     NEWRELIC_METRICS_MAX_DRAIN_PASSES,
     NEWRELIC_METRICS_MAX_RETRY_QUEUE_SIZE,
     NewRelicCountMetric,
+    NewRelicGaugeMetric,
     NewRelicMetric,
     NewRelicMetricCommon,
     NewRelicMetricEnvelope,
@@ -98,6 +102,8 @@ def _metric_record_from_payload(standard_logging_object: StandardLoggingPayload)
         completion_tokens=int(standard_logging_object.get("completion_tokens") or 0),
         total_tokens=int(standard_logging_object.get("total_tokens") or 0),
         duration_ms=float(standard_logging_object.get("response_time") or 0.0) * 1000.0,
+        team_max_budget=metadata.get("user_api_key_team_max_budget") if metadata else None,
+        team_spend=metadata.get("user_api_key_team_spend") if metadata else None,
     )
 
 
@@ -140,6 +146,33 @@ def _bucket_metrics(bucket_records: tuple[NewRelicMetricRecord, ...]) -> tuple[N
     return (*count_metrics, summary_metric)
 
 
+def _team_budget_gauges(record: NewRelicMetricRecord) -> tuple[NewRelicMetric, ...]:
+    team_max_budget: Final = record.team_max_budget
+    if team_max_budget is None:
+        return ()
+    attributes: Final[Mapping[str, str]] = {  # mutable-ok: JSON leaf; safe_dumps stringifies MappingProxyType
+        key: value[:NEWRELIC_METRIC_ATTRIBUTE_MAX_LEN]
+        for key, value in (("team_id", record.team_id), ("team_alias", record.team_alias))
+        if value
+    }
+    remaining_budget: Final = team_max_budget - (record.team_spend or 0.0) - record.response_cost
+    return (
+        NewRelicGaugeMetric(
+            name=NEWRELIC_METRIC_TEAM_MAX_BUDGET, type="gauge", value=team_max_budget, attributes=attributes
+        ),
+        NewRelicGaugeMetric(
+            name=NEWRELIC_METRIC_TEAM_REMAINING_BUDGET, type="gauge", value=remaining_budget, attributes=attributes
+        ),
+    )
+
+
+def _team_budget_metrics(records: tuple[NewRelicMetricRecord, ...]) -> tuple[NewRelicMetric, ...]:
+    latest_by_team: Final[Mapping[str, NewRelicMetricRecord]] = MappingProxyType(
+        {record.team_id: record for record in records if record.team_id}
+    )
+    return tuple(gauge for record in latest_by_team.values() for gauge in _team_budget_gauges(record))
+
+
 def build_metric_payload(
     records: tuple[NewRelicMetricRecord, ...],
     *,
@@ -158,7 +191,7 @@ def build_metric_payload(
         "timestamp": int(window_start * 1000),
         "interval.ms": interval_ms,
     }
-    return (NewRelicMetricEnvelope(common=common, metrics=metrics),)
+    return (NewRelicMetricEnvelope(common=common, metrics=(*metrics, *_team_budget_metrics(records))),)
 
 
 class NewRelicMetricsLogger(CustomBatchLogger):
diff --git a/litellm/integrations/pointfive/__init__.py b/litellm/integrations/pointfive/__init__.py
new file mode 100644
index 00000000000..1f3ca3c65c7
--- /dev/null
+++ b/litellm/integrations/pointfive/__init__.py
@@ -0,0 +1,5 @@
+"""PointFive logging integration for LiteLLM."""
+
+from litellm.integrations.pointfive.logger import PointFiveLogger
+
+__all__ = ("PointFiveLogger",)
diff --git a/litellm/integrations/pointfive/logger.py b/litellm/integrations/pointfive/logger.py
new file mode 100644
index 00000000000..c352dac11e7
--- /dev/null
+++ b/litellm/integrations/pointfive/logger.py
@@ -0,0 +1,304 @@
+"""
+PointFive logging integration.
+
+Buffers ``StandardLoggingPayload`` records and ships each flush as one gzipped
+newline-delimited JSON object, rather than one object per request. Uploads go through a
+presigned URL issued by the PointFive API, so the proxy needs no cloud credentials and
+runs unchanged wherever it is hosted.
+"""
+
+import asyncio
+from collections.abc import Mapping
+from datetime import datetime
+from typing import Final
+
+import litellm
+from litellm._logging import verbose_logger
+from litellm.integrations.custom_batch_logger import CustomBatchLogger
+from litellm.integrations.pointfive.payload import chunk_lines, encode_lines, serialize_records
+from litellm.integrations.pointfive.upload_client import PointFiveUploadClient, PointFiveUploadError
+from litellm.litellm_core_utils.redact_messages import (
+    redacted_standard_logging_payload,
+    should_redact_message_logging,
+)
+from litellm.llms.custom_httpx.http_handler import get_async_httpx_client, httpxSpecialProvider
+from litellm.secret_managers.main import get_secret_str
+from litellm.types.integrations.base_health_check import IntegrationHealthCheckStatus
+from litellm.types.integrations.pointfive import DEFAULT_API_URL, PointFiveInitParams, PointFiveUploadFailure
+
+_ENV_REFERENCE_PREFIX: Final = "os.environ/"
+
+
+def _resolved_secret(value: str | None) -> str | None:
+    """
+    Resolve a config value that may name a secret, in any shape the secret manager accepts.
+
+    A reference that resolves to nothing stays unresolved rather than falling back to its own
+    text, so an unset ``os.environ/NAME`` reports a missing key instead of being sent as one.
+    """
+    if value is None:
+        return None
+    resolved: Final = get_secret_str(value)
+    if resolved:
+        return resolved
+    return None if value.startswith(_ENV_REFERENCE_PREFIX) else value
+
+
+def _configured_params() -> PointFiveInitParams:
+    """Read ``litellm.pointfive_params``, validating a raw config dict on the way through."""
+    configured: Final = litellm.pointfive_params
+    if isinstance(configured, PointFiveInitParams):
+        return configured
+    if isinstance(configured, Mapping):
+        return PointFiveInitParams.model_validate(configured)
+    return PointFiveInitParams()
+
+
+def _resolved_api_key(params: PointFiveInitParams) -> str | None:
+    """Prefer the configured key, falling back to the environment the proxy UI writes."""
+    return _resolved_secret(params.api_key) or get_secret_str("POINTFIVE_API_KEY")
+
+
+def _resolved_api_url(params: PointFiveInitParams) -> str:
+    """Prefer the configured url, then the environment, then the public endpoint."""
+    return _resolved_secret(params.api_url) or get_secret_str("POINTFIVE_API_URL") or DEFAULT_API_URL
+
+
+def _upload_client_for(params: PointFiveInitParams) -> PointFiveUploadClient:
+    """
+    Build an upload client for the key and url configured right now.
+
+    Resolved per call rather than kept: the proxy ui writes new values into the
+    environment of a running proxy, and reading them once would need a restart to take
+    effect. ``get_async_httpx_client`` is cached, so this reuses the same connections.
+    """
+    api_key: Final = _resolved_api_key(params)
+    if not api_key:
+        raise ValueError(
+            "pointfive logging requires an api key. Set POINTFIVE_API_KEY, or "
+            "litellm_settings.pointfive_params.api_key in config.yaml"
+        )
+    return PointFiveUploadClient(
+        api_key=api_key,
+        api_url=_resolved_api_url(params),
+        http_client=get_async_httpx_client(llm_provider=httpxSpecialProvider.LoggingCallback),
+        max_retries=params.max_upload_retries,
+    )
+
+
+class PointFiveLogger(CustomBatchLogger):
+    """Batching callback that ships LiteLLM request logs to PointFive."""
+
+    preserve_events_added_during_flush = True
+
+    def __init__(
+        self,
+        params: PointFiveInitParams | None = None,
+        upload_client: PointFiveUploadClient | None = None,
+        start_periodic_flush: bool = True,
+    ) -> None:
+        resolved: Final = params if params is not None else _configured_params()
+        self.max_batch_bytes: Final = resolved.max_batch_bytes
+        self.params: Final = resolved
+        self.given_upload_client: Final = upload_client
+        if upload_client is None:
+            _upload_client_for(resolved)  # refuse to start without a key, rather than at the first flush
+        super().__init__(
+            flush_lock=asyncio.Lock(),
+            batch_size=resolved.batch_size,
+            flush_interval=resolved.flush_interval,
+            turn_off_message_logging=bool(resolved.turn_off_message_logging),
+        )
+        self._flushing: bool = False
+        self._batch_flush_task: asyncio.Task[None] | None = None
+        self._periodic_flush_task: asyncio.Task[None] | None = (
+            self._start_periodic_flush_task() if start_periodic_flush else None
+        )
+
+    @property
+    def upload_client(self) -> PointFiveUploadClient:
+        """The client for the currently configured key and url, so a ui edit needs no restart."""
+        if self.given_upload_client is not None:
+            return self.given_upload_client
+        return _upload_client_for(self.params)
+
+    def _start_periodic_flush_task(self) -> asyncio.Task[None] | None:
+        """Start the periodic flush only once an event loop is actually running."""
+        try:
+            loop: Final = asyncio.get_running_loop()
+        except RuntimeError:
+            return None
+        return loop.create_task(self.periodic_flush())
+
+    def _start_batch_flush_task(self) -> None:
+        """
+        Upload a full batch in the background, so no request waits on PointFive.
+
+        Awaiting it here put the upload, its retries and their backoff on the caller's
+        path, and a hung api held a response open for as long as the attempts took.
+        """
+        if self._batch_flush_task is not None and not self._batch_flush_task.done():
+            return
+        try:
+            loop: Final = asyncio.get_running_loop()
+        except RuntimeError:
+            return
+        self._batch_flush_task = loop.create_task(self.flush_queue(skip_if_flushing=True))
+
+    def _flush_task_is_alive(self) -> bool:
+        """A task whose loop has been closed never runs again, yet never reports itself done."""
+        task: Final = self._periodic_flush_task
+        return task is not None and not task.done() and not task.get_loop().is_closed()
+
+    async def periodic_flush(self) -> None:
+        """
+        Report in straight away, then flush on the interval as usual.
+
+        The inherited loop sleeps first, so a proxy that has just loaded the callback says
+        nothing for a whole interval, five minutes by default. PointFive shows the integration
+        as still waiting for its first call for all that time, which reads as a broken setup
+        rather than an idle one. An empty queue makes this first cycle a ping, so a proxy with
+        no traffic yet announces itself without uploading an object that holds no records.
+        """
+        await self.flush_queue(skip_if_flushing=True)
+        await super().periodic_flush()
+
+    async def async_log_success_event(
+        self,
+        kwargs: Mapping[str, object],
+        response_obj: object,
+        start_time: datetime,
+        end_time: datetime,
+    ) -> None:
+        await self._enqueue(kwargs)
+
+    async def async_log_failure_event(
+        self,
+        kwargs: Mapping[str, object],
+        response_obj: object,
+        start_time: datetime,
+        end_time: datetime,
+    ) -> None:
+        await self._enqueue(kwargs)
+
+    async def _enqueue(self, kwargs: Mapping[str, object]) -> None:
+        """Buffer one record, flushing early once the batch threshold is reached."""
+        try:
+            if not self._flush_task_is_alive():
+                self._periodic_flush_task = self._start_periodic_flush_task()
+
+            record: Final = self._record_for(kwargs)
+            if record is None:
+                verbose_logger.debug("pointfive: event carried no standard_logging_object, skipping")
+                return
+
+            self.log_queue.append(record)
+            self._drop_overflow()
+            if len(self.log_queue) >= self.batch_size:
+                self._start_batch_flush_task()
+        except Exception:  # noqa: BLE001  # logging must never break the request path
+            verbose_logger.exception("pointfive: failed to queue an event")
+
+    def _record_for(self, kwargs: Mapping[str, object]) -> Mapping[str, object] | None:
+        """
+        The record to buffer, redacted the way the framework would have redacted it.
+
+        A success reaches a callback already redacted, an async failure does not, so both
+        the excluded-field list and this callback's own setting are applied here, then the
+        global, per-request and header settings that only the framework's predicate knows.
+        """
+        details: Final = self.redact_standard_logging_payload_from_model_call_details(
+            dict(kwargs)  # mutable-ok: both framework helpers take the call details as a dict
+        )
+        payload: Final = details.get("standard_logging_object")
+        if not isinstance(payload, dict):
+            return None
+        if should_redact_message_logging(details):
+            return redacted_standard_logging_payload(payload)
+        return payload
+
+    def _drop_overflow(self) -> None:
+        """
+        Hold the queue to its cap as records arrive, not only after a flush has failed.
+
+        Never while a flush is running: it holds a snapshot taken by length, and trimming
+        the front underneath it would make the post-flush drain remove records that arrived
+        during the upload and were never sent. The next arrival after the flush trims.
+        """
+        if self._flushing:
+            return
+        overflow: Final = len(self.log_queue) - self.max_queue_size
+        if overflow <= 0:
+            return
+        del self.log_queue[:overflow]
+        verbose_logger.warning("pointfive: queue over %s records, dropped %s oldest", self.max_queue_size, overflow)
+
+    async def flush_queue(self, skip_if_flushing: bool = False) -> None:
+        """
+        Flush as usual, or report liveness when there is nothing to send.
+
+        ``CustomBatchLogger`` skips an empty queue entirely, so without this an idle proxy
+        would look identical to a dead one.
+
+        ``skip_if_flushing`` is what a full batch, and the loop's opening cycle, pass. Uploading one takes seconds, and
+        every event arriving meanwhile crosses the threshold too, so each would queue on the
+        flush lock and then ship the handful of records left behind it. That turns one burst
+        into a stream of tiny objects, which is what batching exists to avoid. The running
+        flush already carries what is queued, and the interval catches whatever it missed.
+        """
+        if not self.log_queue:
+            await self._ping()
+            return
+        if skip_if_flushing and self._flushing:
+            return
+
+        self._flushing = True
+        try:
+            await super().flush_queue()
+        finally:
+            self._flushing = False
+
+    async def async_health_check(self) -> IntegrationHealthCheckStatus:
+        """Answer the proxy ui test button by asking the api whether it accepts this key."""
+        try:
+            failure: Final = await self.upload_client.ping()
+        except ValueError as missing_key:
+            return IntegrationHealthCheckStatus(status="unhealthy", error_message=str(missing_key))
+        if failure is not None:
+            return IntegrationHealthCheckStatus(status="unhealthy", error_message=failure.detail)
+        return IntegrationHealthCheckStatus(status="healthy", error_message=None)
+
+    async def _ping(self) -> None:
+        """Report liveness, never failing the flush over it."""
+        try:
+            failure: Final = await self.upload_client.ping()
+        except ValueError as missing_key:
+            verbose_logger.warning("pointfive: liveness ping skipped, %s", missing_key)
+            return
+        if failure is not None:
+            verbose_logger.warning("pointfive: liveness ping failed, %s", failure.detail)
+
+    async def async_send_batch(self) -> None:
+        """
+        Upload everything queued, split into objects of at most ``max_batch_bytes``.
+
+        A retryable failure propagates so ``CustomBatchLogger`` keeps the rest of the batch
+        for the next flush; the records already shipped or already refused leave the queue
+        first, so a retry re-sends at most the object that failed. A rejection the server
+        will refuse again drops that object, since holding it would block every record
+        queued behind it.
+        """
+        pending: Final = tuple(self.log_queue)
+        if not pending:
+            return
+
+        client: Final = self.upload_client
+        chunks: Final = chunk_lines(serialize_records(pending), self.max_batch_bytes)
+        for index, chunk in enumerate(chunks):
+            outcome = await client.upload(await encode_lines(chunk))
+            if not isinstance(outcome, PointFiveUploadFailure):
+                continue
+            if outcome.retryable:
+                del self.log_queue[: sum(len(shipped) for shipped in chunks[:index])]
+                raise PointFiveUploadError(outcome.detail)
+            verbose_logger.error("pointfive: dropping %s records, %s", len(chunk), outcome.detail)
diff --git a/litellm/integrations/pointfive/payload.py b/litellm/integrations/pointfive/payload.py
new file mode 100644
index 00000000000..e3362eda4ee
--- /dev/null
+++ b/litellm/integrations/pointfive/payload.py
@@ -0,0 +1,53 @@
+"""Turns buffered log records into the gzipped NDJSON objects that get uploaded."""
+
+import gzip
+from collections.abc import Iterator, Mapping, Sequence
+from itertools import accumulate, groupby, islice
+from typing import Final
+
+from litellm.litellm_core_utils.asyncify import asyncify
+from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
+
+_NEWLINE_BYTES: Final = 1
+
+
+def serialize_records(records: Sequence[Mapping[str, object]]) -> tuple[str, ...]:
+    """Serialize each record to one JSON line."""
+    return tuple(safe_dumps(record) for record in records)
+
+
+def _encoded_size(line: str) -> int:
+    return len(line.encode("utf-8")) + _NEWLINE_BYTES
+
+
+def _object_indices(sizes: Sequence[int], max_bytes: int) -> Iterator[int]:
+    """Number each line with the object it belongs to, opening a new one on overflow."""
+
+    def advance(state: tuple[int, int], size: int) -> tuple[int, int]:
+        index, used = state
+        return (index + 1, size) if used and used + size > max_bytes else (index, used + size)
+
+    return (index for index, _ in islice(accumulate(sizes, advance, initial=(0, 0)), 1, None))
+
+
+def chunk_lines(lines: Sequence[str], max_bytes: int) -> tuple[tuple[str, ...], ...]:
+    """
+    Group serialized lines into objects of at most ``max_bytes`` uncompressed.
+
+    A line above the bound on its own still becomes its own object. A record cannot be
+    split, and holding it back would stall every record queued behind it.
+    """
+    sizes: Final = tuple(_encoded_size(line) for line in lines)
+    numbered: Final = zip(_object_indices(sizes, max_bytes), lines, strict=True)
+    return tuple(tuple(line for _, line in group) for _, group in groupby(numbered, lambda pair: pair[0]))
+
+
+async def encode_lines(lines: Sequence[str]) -> bytes:
+    """
+    Join lines as NDJSON and gzip them off the event loop.
+
+    An object can be several megabytes, and compressing that inline would block the
+    proxy for as long as it takes.
+    """
+    compress: Final = asyncify(gzip.compress)
+    return await compress("\n".join(lines).encode("utf-8"))
diff --git a/litellm/integrations/pointfive/upload_client.py b/litellm/integrations/pointfive/upload_client.py
new file mode 100644
index 00000000000..56ba6689017
--- /dev/null
+++ b/litellm/integrations/pointfive/upload_client.py
@@ -0,0 +1,194 @@
+"""
+Uploads one batch to PointFive through a presigned URL.
+
+The proxy holds no cloud credentials. For every batch it asks the PointFive API for a
+single-use presigned URL and PUTs the bytes there, so the same plugin runs unchanged on
+AWS, GCP, Azure or on-prem. The server picks the object key, so the proxy never chooses
+where its data lands.
+"""
+
+import asyncio
+from collections.abc import Awaitable, Callable
+from types import MappingProxyType
+from typing import Final
+
+import httpx
+from pydantic import BaseModel, Field, ValidationError
+
+import litellm
+from litellm._logging import verbose_logger
+from litellm.litellm_core_utils.url_utils import SSRFError, validate_url
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
+from litellm.types.integrations.pointfive import (
+    RETRYABLE_UPLOAD_STATUS_CODES,
+    PointFiveUploadFailure,
+    PointFiveUploadTarget,
+)
+
+UPLOAD_KIND: Final = "LITELLM"
+UPLOAD_URL_PATH: Final = "/upload-url"
+PING_PATH: Final = "/ping"
+PUT_HEADERS: Final = MappingProxyType({"Content-Type": "application/x-ndjson", "Content-Encoding": "gzip"})
+
+
+class _PresignRequest(BaseModel):
+    kind: str = UPLOAD_KIND
+    byte_count: int = Field(serialization_alias="byteCount")
+
+
+class _PingRequest(BaseModel):
+    kind: str = UPLOAD_KIND
+
+
+class _TargetPayload(BaseModel):
+    upload_url: str = Field(alias="uploadUrl")
+    object_key: str = Field(alias="objectKey")
+
+
+class _ErrorPayload(BaseModel):
+    error: str = ""
+
+
+class PointFiveUploadError(Exception):
+    """A batch could not be uploaded and the failure is worth retrying."""
+
+
+def _failure_for(response: httpx.Response, what: str) -> PointFiveUploadFailure:
+    detail: Final = f"{what} returned {response.status_code}"
+    reason: Final = _refusal_reason(response.text)
+    return PointFiveUploadFailure(
+        f"{detail}, {reason}" if reason else detail,
+        retryable=response.status_code in RETRYABLE_UPLOAD_STATUS_CODES,
+    )
+
+
+def _refusal_reason(body: str) -> str:
+    try:
+        return _ErrorPayload.model_validate_json(body).error
+    except ValidationError:
+        return ""
+
+
+def _parse_target(body: str) -> PointFiveUploadTarget | PointFiveUploadFailure:
+    try:
+        target: Final = _TargetPayload.model_validate_json(body)
+    except ValidationError:
+        return PointFiveUploadFailure("pointfive api returned an unreadable body", retryable=False)
+    return PointFiveUploadTarget(upload_url=target.upload_url, object_key=target.object_key)
+
+
+class PointFiveUploadClient:
+    """Presigns and uploads one batch at a time."""
+
+    def __init__(
+        self,
+        api_key: str,
+        api_url: str,
+        http_client: AsyncHTTPHandler,
+        max_retries: int,
+        sleep: Callable[[float], Awaitable[None]] = asyncio.sleep,
+        validate_upload_url: Callable[[str], tuple[str, str]] = validate_url,
+    ) -> None:
+        self.api_key: Final = api_key
+        self.api_url: Final = api_url.rstrip("/")
+        self.http_client: Final = http_client
+        self.max_retries: Final = max_retries
+        self.sleep: Final = sleep
+        self.validate_upload_url: Final = validate_upload_url
+
+    async def upload(self, body: bytes) -> str | PointFiveUploadFailure:
+        """
+        Upload one gzipped batch, returning the object key it landed at.
+
+        Every attempt presigns again, so a retry never reuses a URL that has expired or
+        has already been consumed.
+        """
+        for attempt in range(self.max_retries):
+            match await self._upload_once(body):
+                case PointFiveUploadFailure(retryable=True) as failure:
+                    if attempt + 1 >= self.max_retries:
+                        return PointFiveUploadFailure(
+                            f"{failure.detail}, gave up after {self.max_retries} attempts", retryable=True
+                        )
+                    await self.sleep(float(1 << attempt))
+                case outcome:
+                    return outcome
+        return PointFiveUploadFailure("max_upload_retries must be at least 1", retryable=False)
+
+    async def _upload_once(self, body: bytes) -> str | PointFiveUploadFailure:
+        target: Final = await self._presign(len(body))
+        if isinstance(target, PointFiveUploadFailure):
+            return target
+
+        rejection: Final = await self._put(target, body)
+        if rejection is not None:
+            return rejection
+
+        verbose_logger.debug("pointfive: uploaded %s gzipped bytes to %s", len(body), target.object_key)
+        return target.object_key
+
+    async def ping(self) -> PointFiveUploadFailure | None:
+        """Report that the proxy is alive when it has nothing to upload."""
+        body: Final = await self._post(PING_PATH, _PingRequest())
+        if isinstance(body, PointFiveUploadFailure):
+            return body
+        return None
+
+    async def _presign(self, byte_count: int) -> PointFiveUploadTarget | PointFiveUploadFailure:
+        """Ask the PointFive API for a presigned URL sized to this batch."""
+        body: Final = await self._post(UPLOAD_URL_PATH, _PresignRequest(byte_count=byte_count))
+        if isinstance(body, PointFiveUploadFailure):
+            return body
+        return _parse_target(body)
+
+    async def _post(self, path: str, request: BaseModel) -> str | PointFiveUploadFailure:
+        """POST one JSON request to the PointFive ingestion API and return its raw body."""
+        try:
+            response: Final = await self.http_client.post(
+                self.api_url + path,
+                json=request.model_dump(by_alias=True),
+                headers={  # mutable-ok: AsyncHTTPHandler.post types headers as dict
+                    "Authorization": f"Bearer {self.api_key}",
+                    "Content-Type": "application/json",
+                },
+            )
+        except httpx.HTTPStatusError as e:
+            return _failure_for(e.response, "pointfive api")
+        except Exception as e:  # noqa: BLE001  # a transport fault is worth another attempt
+            return PointFiveUploadFailure(f"pointfive api unreachable: {type(e).__name__}", retryable=True)
+        return response.text
+
+    async def _put(self, target: PointFiveUploadTarget, body: bytes) -> PointFiveUploadFailure | None:
+        """
+        PUT the batch to the presigned URL, which carries its own authorization.
+
+        The server chose that URL, so it is treated like any other externally supplied
+        destination: the host is checked against blocked networks before connecting, and
+        a redirect is refused rather than followed. A presigned URL never legitimately
+        redirects, and following one would let a compromised endpoint point the proxy at
+        an internal service.
+        """
+        destination: Final = self._destination(target.upload_url)
+        if isinstance(destination, PointFiveUploadFailure):
+            return destination
+        url, host = destination
+        headers: Final = dict(PUT_HEADERS, Host=host) if host else dict(PUT_HEADERS)  # mutable-ok: put wants dict
+        try:
+            await self.http_client.put(url, data=body, headers=headers, follow_redirects=False)
+        except httpx.HTTPStatusError as e:
+            if e.response.is_redirect:
+                return PointFiveUploadFailure(
+                    f"presigned upload redirected with {e.response.status_code}, refusing to follow", retryable=False
+                )
+            return _failure_for(e.response, "presigned upload")
+        except Exception as e:  # noqa: BLE001  # a transport fault is worth another attempt
+            return PointFiveUploadFailure(f"presigned upload unreachable: {type(e).__name__}", retryable=True)
+        return None
+
+    def _destination(self, upload_url: str) -> tuple[str, str | None] | PointFiveUploadFailure:
+        if not getattr(litellm, "user_url_validation", True):
+            return upload_url, None
+        try:
+            return self.validate_upload_url(upload_url)
+        except SSRFError as e:
+            return PointFiveUploadFailure(f"presigned upload url refused: {e}", retryable=False)
diff --git a/litellm/integrations/prometheus.py b/litellm/integrations/prometheus.py
index 6766d246894..540ce6738fc 100644
--- a/litellm/integrations/prometheus.py
+++ b/litellm/integrations/prometheus.py
@@ -246,6 +246,7 @@ class PrometheusLogger(CustomLogger):
             # logger so toggling these flags only takes effect after a
             # restart, keeping init-time and runtime label sets in sync.
             self._cached_metric_labels: dict[str, list[str]] = {}
+            self._emit_input_sequence_length_label = litellm.prometheus_emit_input_sequence_length_label is True
 
             _custom_buckets: Final = litellm.prometheus_latency_buckets
             self.latency_buckets = tuple(_custom_buckets) if _custom_buckets is not None else LATENCY_BUCKETS
@@ -1522,6 +1523,11 @@ class PrometheusLogger(CustomLogger):
             # 2. Pyright does not allow us to run isinstance(standard_logging_payload, StandardLoggingPayload) <- this would be ideal
             enum_values=enum_values,
             label_context=label_context,
+            input_sequence_length=(
+                self._get_input_sequence_length(standard_logging_payload, kwargs, response_obj)
+                if self._emit_input_sequence_length_label
+                else None
+            ),
         )
 
         # set x-ratelimit headers
@@ -2192,6 +2198,36 @@ class PrometheusLogger(CustomLogger):
         )
         self.litellm_remaining_api_key_tokens_for_model.labels(**tokens_labels).set(remaining_tokens)
 
+    @staticmethod
+    def _get_input_sequence_length(
+        standard_logging_payload: StandardLoggingPayload,
+        kwargs: Mapping[str, object],
+        response_obj: object,
+    ) -> str:
+        prompt_tokens: Final = standard_logging_payload.get("prompt_tokens")
+        if prompt_tokens:
+            return get_input_sequence_length_bucket(prompt_tokens)
+        combined_usage: Final = kwargs.get("combined_usage_object")
+        if (
+            combined_usage is not None
+            and getattr(kwargs.get("_litellm_upstream_reported_usage"), "total_tokens", None) is not None
+        ):
+            return get_input_sequence_length_bucket(None)
+        reported_usage: Final = (
+            response_obj.get("usage") if isinstance(response_obj, dict) else getattr(response_obj, "usage", None)
+        )
+        if reported_usage is None and combined_usage is None:
+            return get_input_sequence_length_bucket(None)
+        usage_metadata: Final = standard_logging_payload["metadata"].get("usage_object")
+        if isinstance(usage_metadata, Mapping):
+            return get_input_sequence_length_bucket(usage_metadata.get("prompt_tokens"))
+        if combined_usage is None and isinstance(response_obj, dict):
+            from litellm.litellm_core_utils.litellm_logging import StandardLoggingPayloadSetup
+
+            normalized_usage: Final[Mapping[str, object]] = StandardLoggingPayloadSetup.get_usage_as_dict(response_obj)
+            return get_input_sequence_length_bucket(normalized_usage.get("prompt_tokens"))
+        return get_input_sequence_length_bucket(prompt_tokens)
+
     def _set_latency_metrics(
         self,
         kwargs: dict,
@@ -2202,7 +2238,16 @@ class PrometheusLogger(CustomLogger):
         user_api_team_alias: str | None,
         enum_values: UserAPIKeyLabelValues,
         label_context: PrometheusLabelFactoryContext | None = None,
+        input_sequence_length: str | None = None,
     ):
+        latency_enum_values: Final = (
+            replace(enum_values, input_sequence_length=input_sequence_length)
+            if input_sequence_length is not None
+            else enum_values
+        )
+        latency_label_context: Final = (
+            PrometheusLabelFactoryContext(latency_enum_values) if input_sequence_length is not None else label_context
+        )
         # latency metrics
         end_time: Final[datetime] = kwargs.get("end_time") or datetime.now()
         start_time: Final[datetime | None] = kwargs.get("start_time")
@@ -2220,8 +2265,8 @@ class PrometheusLogger(CustomLogger):
                 supported_enum_labels=self.get_labels_for_metric(
                     metric_name="litellm_llm_api_time_to_first_token_metric"
                 ),
-                enum_values=enum_values,
-                label_context=label_context,
+                enum_values=latency_enum_values,
+                label_context=latency_label_context,
             )
             self.litellm_llm_api_time_to_first_token_metric.labels(**_ttft_labels).observe(time_to_first_token_seconds)
             self._track_end_user_metric_series(
@@ -2241,8 +2286,8 @@ class PrometheusLogger(CustomLogger):
         if api_call_total_time_seconds is not None:
             _labels = prometheus_label_factory(
                 supported_enum_labels=self.get_labels_for_metric(metric_name="litellm_llm_api_latency_metric"),
-                enum_values=enum_values,
-                label_context=label_context,
+                enum_values=latency_enum_values,
+                label_context=latency_label_context,
             )
             self.litellm_llm_api_latency_metric.labels(**_labels).observe(api_call_total_time_seconds)
             self._track_end_user_metric_series(
@@ -2272,8 +2317,8 @@ class PrometheusLogger(CustomLogger):
             )
             _labels = prometheus_label_factory(
                 supported_enum_labels=self.get_labels_for_metric(metric_name="litellm_request_total_latency_metric"),
-                enum_values=enum_values,
-                label_context=label_context,
+                enum_values=latency_enum_values,
+                label_context=latency_label_context,
             )
             self.litellm_request_total_latency_metric.labels(**_labels).observe(_observed_total_time_seconds)
             self._track_end_user_metric_series(
diff --git a/litellm/integrations/s3_v2.py b/litellm/integrations/s3_v2.py
index 712ce41d09e..972ac79e306 100644
--- a/litellm/integrations/s3_v2.py
+++ b/litellm/integrations/s3_v2.py
@@ -10,9 +10,11 @@ import asyncio
 import time
 from collections.abc import Mapping
 from datetime import datetime
-from typing import Final, cast
+from typing import TYPE_CHECKING, Final, cast
 from urllib.parse import quote
 
+import httpx
+
 import litellm
 from litellm._logging import print_verbose, verbose_logger
 from litellm.constants import DEFAULT_S3_BATCH_SIZE, DEFAULT_S3_FLUSH_INTERVAL_SECONDS
@@ -24,7 +26,7 @@ from litellm.integrations.s3 import (
 from litellm.litellm_core_utils.aws_partition import get_aws_dns_suffix
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
 from litellm.litellm_core_utils.sensitive_data_masker import SensitiveDataMasker
-from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM
+from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM, run_aws_signing
 from litellm.llms.custom_httpx.http_handler import (
     _get_httpx_client,
     get_async_httpx_client,
@@ -35,6 +37,9 @@ from litellm.types.utils import StandardAuditLogPayload, StandardLoggingPayload
 
 from .custom_batch_logger import CustomBatchLogger
 
+if TYPE_CHECKING:
+    from botocore.credentials import Credentials
+
 
 class S3Logger(CustomBatchLogger, BaseAWSLLM):
     def __init__(
@@ -232,6 +237,26 @@ class S3Logger(CustomBatchLogger, BaseAWSLLM):
             f"{get_aws_dns_suffix(self.s3_region_name)}/{encoded_key}"
         )
 
+    def _sign_put(
+        self, credentials: "Credentials", url: str, json_string: str, headers: Mapping[str, str]
+    ) -> dict[str, str]:  # mutable-ok: [LIT001] AsyncHTTPHandler.put/HTTPHandler.put only accept dict headers
+        """
+        ``RefreshableCredentials`` (IMDS roles) may refresh between the access key, secret and token
+        reads SigV4 performs, producing a mixed-generation signature that S3 rejects with 403.
+        Freezing first makes the three values one atomic snapshot.
+        """
+        from botocore.auth import S3SigV4Auth
+        from botocore.awsrequest import AWSRequest
+        from botocore.credentials import RefreshableCredentials
+
+        frozen: Final = (
+            credentials.get_frozen_credentials() if isinstance(credentials, RefreshableCredentials) else credentials
+        )
+        aws_request: Final = AWSRequest(method="PUT", url=url, data=json_string, headers=dict(headers))
+        aws_region_name: Final = self.get_aws_region_name_for_non_llm_api_calls(aws_region_name=self.s3_region_name)
+        S3SigV4Auth(frozen, "s3", aws_region_name).add_auth(aws_request)
+        return dict(aws_request.headers.items())
+
     def _sse_headers(self) -> Mapping[str, str]:
         candidates: Final = {
             "x-amz-server-side-encryption": self.s3_server_side_encryption,
@@ -317,26 +342,12 @@ class S3Logger(CustomBatchLogger, BaseAWSLLM):
         try:
             import base64
             import hashlib
-
-            from botocore.auth import S3SigV4Auth
-            from botocore.awsrequest import AWSRequest
         except ImportError:
             raise ImportError("Missing boto3 to call bedrock. Run 'pip install boto3'.")
         try:
             from litellm.litellm_core_utils.asyncify import asyncify
 
             asyncified_get_credentials: Final = asyncify(self.get_credentials)
-            credentials: Final = await asyncified_get_credentials(
-                aws_access_key_id=self.s3_aws_access_key_id,
-                aws_secret_access_key=self.s3_aws_secret_access_key,
-                aws_session_token=self.s3_aws_session_token,
-                aws_region_name=self.s3_region_name,
-                aws_session_name=self.s3_aws_session_name,
-                aws_profile_name=self.s3_aws_profile_name,
-                aws_role_name=self.s3_aws_role_name,
-                aws_web_identity_token=self.s3_aws_web_identity_token,
-                aws_sts_endpoint=self.s3_aws_sts_endpoint,
-            )
 
             verbose_logger.debug("s3_v2 logger - uploading data to s3 - %s", batch_logging_element.s3_object_key)
             verbose_logger.debug("s3_v2 logger - s3_verify setting: %s", self.s3_verify)
@@ -363,19 +374,28 @@ class S3Logger(CustomBatchLogger, BaseAWSLLM):
                 **self._sse_headers(),
             }
 
-            # Sign the request
-            aws_request: Final = AWSRequest(method="PUT", url=url, data=json_string, headers=headers)
-            aws_region_name: Final = self.get_aws_region_name_for_non_llm_api_calls(aws_region_name=self.s3_region_name)
-            S3SigV4Auth(credentials, "s3", aws_region_name).add_auth(aws_request)
+            async def signed_put() -> httpx.Response:
+                credentials: Final = await asyncified_get_credentials(
+                    aws_access_key_id=self.s3_aws_access_key_id,
+                    aws_secret_access_key=self.s3_aws_secret_access_key,
+                    aws_session_token=self.s3_aws_session_token,
+                    aws_region_name=self.s3_region_name,
+                    aws_session_name=self.s3_aws_session_name,
+                    aws_profile_name=self.s3_aws_profile_name,
+                    aws_role_name=self.s3_aws_role_name,
+                    aws_web_identity_token=self.s3_aws_web_identity_token,
+                    aws_sts_endpoint=self.s3_aws_sts_endpoint,
+                )
+                signed_headers: Final = await run_aws_signing(self._sign_put, credentials, url, json_string, headers)
+                try:
+                    return await self.async_httpx_client.put(url, data=json_string, headers=signed_headers)
+                except httpx.HTTPStatusError as error:
+                    return error.response
 
-            # Prepare the signed headers
-            signed_headers: Final = dict(aws_request.headers.items())
-
-            # Make the request with retry for transient S3 errors (500/503)
             max_retries: Final = 3
             for attempt in range(max_retries):
-                response = await self.async_httpx_client.put(url, data=json_string, headers=signed_headers)
-                if response.status_code in (500, 503) and attempt < max_retries - 1:
+                response = await signed_put()
+                if response.status_code in (403, 500, 503) and attempt < max_retries - 1:
                     wait_time = 2**attempt  # 1s, 2s
                     verbose_logger.warning(
                         "S3 upload returned %s, retrying in %ss (attempt %s/%s) key=%s",
@@ -479,20 +499,10 @@ class S3Logger(CustomBatchLogger, BaseAWSLLM):
         try:
             import base64
             import hashlib
-
-            from botocore.auth import S3SigV4Auth
-            from botocore.awsrequest import AWSRequest
-            from botocore.credentials import Credentials
         except ImportError:
             raise ImportError("Missing boto3 to call bedrock. Run 'pip install boto3'.")
         try:
             verbose_logger.debug("s3_v2 logger - uploading data to s3 - %s", batch_logging_element.s3_object_key)
-            credentials: Final[Credentials] = self.get_credentials(
-                aws_access_key_id=self.s3_aws_access_key_id,
-                aws_secret_access_key=self.s3_aws_secret_access_key,
-                aws_session_token=self.s3_aws_session_token,
-                aws_region_name=self.s3_region_name,
-            )
 
             url: Final = self._build_object_url(batch_logging_element.s3_object_key)
 
@@ -516,22 +526,24 @@ class S3Logger(CustomBatchLogger, BaseAWSLLM):
                 **self._sse_headers(),
             }
 
-            # Sign the request
-            aws_request: Final = AWSRequest(method="PUT", url=url, data=json_string, headers=headers)
-            aws_region_name: Final = self.get_aws_region_name_for_non_llm_api_calls(aws_region_name=self.s3_region_name)
-            S3SigV4Auth(credentials, "s3", aws_region_name).add_auth(aws_request)
-
-            # Prepare the signed headers
-            signed_headers: Final = dict(aws_request.headers.items())
-
             httpx_client: Final = _get_httpx_client(
                 params=({"ssl_verify": self.s3_verify} if self.s3_verify is not None else None)
             )
-            # Make the request with retry for transient S3 errors (500/503)
+
+            def signed_put() -> httpx.Response:
+                credentials: Final = self.get_credentials(
+                    aws_access_key_id=self.s3_aws_access_key_id,
+                    aws_secret_access_key=self.s3_aws_secret_access_key,
+                    aws_session_token=self.s3_aws_session_token,
+                    aws_region_name=self.s3_region_name,
+                )
+                signed_headers: Final = self._sign_put(credentials, url, json_string, headers)
+                return httpx_client.put(url, data=json_string, headers=signed_headers)
+
             max_retries: Final = 3
             for attempt in range(max_retries):
-                response = httpx_client.put(url, data=json_string, headers=signed_headers)
-                if response.status_code in (500, 503) and attempt < max_retries - 1:
+                response = signed_put()
+                if response.status_code in (403, 500, 503) and attempt < max_retries - 1:
                     wait_time = 2**attempt  # 1s, 2s
                     verbose_logger.warning(
                         "S3 upload returned %s, retrying in %ss (attempt %s/%s) key=%s",
@@ -597,7 +609,7 @@ class S3Logger(CustomBatchLogger, BaseAWSLLM):
 
             # Sign the request
             aws_request: Final = AWSRequest(method="GET", url=url, headers=headers)
-            S3SigV4Auth(credentials, "s3", self.s3_region_name).add_auth(aws_request)
+            await run_aws_signing(S3SigV4Auth(credentials, "s3", self.s3_region_name).add_auth, aws_request)
 
             # Prepare the signed headers
             signed_headers: Final = dict(aws_request.headers.items())
diff --git a/litellm/integrations/sqs.py b/litellm/integrations/sqs.py
index 2b4c8c9928d..d787375ca3c 100644
--- a/litellm/integrations/sqs.py
+++ b/litellm/integrations/sqs.py
@@ -22,7 +22,7 @@ from litellm.constants import (
     SQS_SEND_MESSAGE_ACTION,
 )
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
-from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM
+from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM, run_aws_signing
 from litellm.llms.custom_httpx.http_handler import (
     get_async_httpx_client,
     httpxSpecialProvider,
@@ -295,7 +295,7 @@ class SQSLogger(CustomBatchLogger, BaseAWSLLM):
                 data=prepped.body,
                 headers=prepped.headers,
             )
-            SigV4Auth(credentials, "sqs", self.sqs_region_name).add_auth(aws_request)
+            await run_aws_signing(SigV4Auth(credentials, "sqs", self.sqs_region_name).add_auth, aws_request)
 
             signed_headers: Final = dict(aws_request.headers.items())
 
diff --git a/litellm/litellm_core_utils/classifier_logging.py b/litellm/litellm_core_utils/classifier_logging.py
new file mode 100644
index 00000000000..fdc1cac26c0
--- /dev/null
+++ b/litellm/litellm_core_utils/classifier_logging.py
@@ -0,0 +1,67 @@
+from collections.abc import Mapping
+from types import MappingProxyType
+from typing import Final
+
+from pydantic import JsonValue, TypeAdapter, ValidationError
+
+from litellm.constants import INTERNAL_CALL_ORIGIN_METADATA_KEY
+from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
+from litellm.litellm_core_utils.sensitive_data_masker import redact_credentials_in_payload
+from litellm.types.utils import AUTOROUTER_CLASSIFIER_CALL_ORIGIN, ClassifierAudit
+
+CLASSIFIER_AUDIT_FIELDS: Final = ("classifier_input", "originating_request_masked")
+_JSON_OBJECT: Final = TypeAdapter(dict[str, JsonValue])
+
+
+def classifier_input_snapshot(value: object, *, openai_sdk: bool = False) -> Mapping[str, JsonValue] | None:
+    try:
+        if openai_sdk and isinstance(value, Mapping):
+            body: Final = MappingProxyType(
+                {key: item for key, item in value.items() if key not in ("extra_headers", "extra_query", "extra_body")}
+            )
+            extra_body: Final = value.get("extra_body")
+            return _JSON_OBJECT.validate_python(
+                MappingProxyType({**body, **extra_body}) if isinstance(extra_body, Mapping) else body
+            )
+        return (
+            _JSON_OBJECT.validate_json(value)
+            if isinstance(value, (str, bytes))
+            else _JSON_OBJECT.validate_python(value)
+        )
+    except ValidationError:
+        return None
+
+
+def is_classifier_call(call_type: str, params: Mapping[str, object]) -> bool:
+    return call_type in ("completion", "acompletion", "responses", "aresponses") and any(
+        isinstance(metadata := params.get(key), Mapping)
+        and metadata.get(INTERNAL_CALL_ORIGIN_METADATA_KEY) == AUTOROUTER_CLASSIFIER_CALL_ORIGIN
+        for key in ("metadata", "litellm_metadata")
+    )
+
+
+def masked_originating_request(request_kwargs: Mapping[str, object] | None) -> Mapping[str, JsonValue] | None:
+    request: Final = request_kwargs.get("proxy_server_request") if request_kwargs is not None else None
+    body: Final = request.get("body") if isinstance(request, Mapping) else None
+    if not isinstance(body, Mapping):
+        return None
+    serializable: Final = classifier_input_snapshot(safe_dumps(body))
+    return classifier_input_snapshot(redact_credentials_in_payload(serializable)) if serializable is not None else None
+
+
+def classifier_audit_fields(payload: Mapping[str, object]) -> ClassifierAudit:
+    classifier_input: Final = classifier_input_snapshot(payload.get("classifier_input"))
+    originating_request: Final = classifier_input_snapshot(payload.get("originating_request_masked"))
+    if classifier_input is None:
+        return (
+            ClassifierAudit(originating_request_masked=originating_request)
+            if originating_request is not None
+            else ClassifierAudit()
+        )
+    if originating_request is None:
+        return ClassifierAudit(classifier_input=classifier_input)
+    return ClassifierAudit(classifier_input=classifier_input, originating_request_masked=originating_request)
+
+
+def without_classifier_audit(payload: Mapping[str, object]) -> dict[str, object]:
+    return {key: value for key, value in payload.items() if key not in CLASSIFIER_AUDIT_FIELDS}
diff --git a/litellm/litellm_core_utils/core_helpers.py b/litellm/litellm_core_utils/core_helpers.py
index eacc3e4860a..aa7d6ca1699 100644
--- a/litellm/litellm_core_utils/core_helpers.py
+++ b/litellm/litellm_core_utils/core_helpers.py
@@ -2,6 +2,7 @@
 ## Helper utilities
 import copy
 import logging
+import re
 from collections.abc import Iterable, Mapping
 from typing import TYPE_CHECKING, Any, Final, Literal
 
@@ -21,6 +22,13 @@ else:
     Span = Any
 
 
+_CODEX_CLIENT_PREFIX_RE: Final = re.compile(r"^codex[-_ /]", re.IGNORECASE)
+
+
+def is_codex_user_agent(user_agent: str) -> bool:
+    return bool(_CODEX_CLIENT_PREFIX_RE.match(user_agent))
+
+
 def safe_divide_seconds(seconds: float, denominator: float, default: float | None = None) -> float | None:
     """
     Safely divide seconds by denominator, handling zero division.
diff --git a/litellm/litellm_core_utils/custom_logger_registry.py b/litellm/litellm_core_utils/custom_logger_registry.py
index 6449aa4d46e..6294f3bc577 100644
--- a/litellm/litellm_core_utils/custom_logger_registry.py
+++ b/litellm/litellm_core_utils/custom_logger_registry.py
@@ -43,6 +43,7 @@ from litellm.integrations.newrelic import NewRelicLogger
 from litellm.integrations.openmeter import OpenMeterLogger
 from litellm.integrations.opentelemetry import OpenTelemetry
 from litellm.integrations.opik.opik import OpikLogger
+from litellm.integrations.pointfive import PointFiveLogger
 from litellm.integrations.posthog import PostHogLogger
 from litellm.integrations.prometheus import PrometheusLogger
 from litellm.integrations.s3_v2 import S3Logger
@@ -95,6 +96,7 @@ class CustomLoggerRegistry:
         "agentops": AgentOps,
         "deepeval": DeepEvalLogger,
         "s3_v2": S3Logger,
+        "pointfive": PointFiveLogger,
         "aws_sqs": SQSLogger,
         "dynamic_rate_limiter": _PROXY_DynamicRateLimitHandler,
         "dynamic_rate_limiter_v3": _PROXY_DynamicRateLimitHandlerV3,
diff --git a/litellm/litellm_core_utils/get_litellm_params.py b/litellm/litellm_core_utils/get_litellm_params.py
index 92b32d32dc0..edd2e88f95c 100644
--- a/litellm/litellm_core_utils/get_litellm_params.py
+++ b/litellm/litellm_core_utils/get_litellm_params.py
@@ -17,6 +17,7 @@ AWS_CREDENTIAL_KWARGS_KEYS: Final = frozenset(
         "aws_web_identity_token",
         "aws_sts_endpoint",
         "aws_external_id",
+        "aws_session_tags",
         "aws_bedrock_runtime_endpoint",
         "aws_bedrock_project_id",
     }
diff --git a/litellm/litellm_core_utils/get_model_cost_map.py b/litellm/litellm_core_utils/get_model_cost_map.py
index cdc4810ff04..91a22144805 100644
--- a/litellm/litellm_core_utils/get_model_cost_map.py
+++ b/litellm/litellm_core_utils/get_model_cost_map.py
@@ -2,6 +2,7 @@
 Pulls the cost + context window + provider route for known models from https://github.com/BerriAI/litellm/blob/main/model_prices_and_context_window.json
 
 This can be disabled by setting the LITELLM_LOCAL_MODEL_COST_MAP environment variable to True.
+The ``lite`` and ``litellm-proxy`` CLI entry points also use the bundled map without fetching.
 
 ```
 export LITELLM_LOCAL_MODEL_COST_MAP=True
@@ -13,11 +14,14 @@ import hashlib
 import json
 import os
 import random
+import sys
+import threading
 import time
 from collections.abc import Awaitable, Callable
 from dataclasses import dataclass, replace
 from datetime import datetime, timezone
 from importlib.resources import files
+from pathlib import Path
 from typing import Final, Protocol
 
 import httpx
@@ -33,6 +37,12 @@ from litellm.litellm_core_utils.fallback_generalizations import (
 )
 
 FALLBACK_GENERALIZATIONS_KEY: Final = "fallback_generalizations"
+_CLI_ENTRYPOINT_NAMES: Final = frozenset({"lite", "litellm-proxy"})
+
+
+def _is_cli_process() -> bool:
+    return Path(sys.argv[0]).stem in _CLI_ENTRYPOINT_NAMES
+
 
 # Reserved top-level keys that are not model entries. They must be excluded
 # from the model-count integrity check so a real upstream shrink can't be masked.
@@ -176,6 +186,11 @@ class GetModelCostMap:
 RETRYABLE_FETCH_STATUS_CODES: Final = frozenset({429, 500, 502, 503, 504})
 MODEL_COST_MAP_FETCH_MAX_ATTEMPTS: Final = 3
 MODEL_COST_MAP_FETCH_MAX_WAIT_SECONDS: Final = 30.0
+_litellm_import_complete = threading.Event()
+
+
+def mark_litellm_import_complete() -> None:
+    _litellm_import_complete.set()
 
 
 @dataclass(frozen=True, slots=True)
@@ -314,12 +329,13 @@ async def _fetch_remote_model_cost_map_with_retry(
 def _fetch_remote_model_cost_map_with_retry_sync(
     url: str,
     timeout: int,
-    max_attempts: int,
+    attempts: range,
     sleep: Callable[[float], None],
     rng: random.Random,
     client: _SyncGetClient,
 ) -> ModelCostMapReloadResult:
-    for attempt in range(1, max_attempts + 1):
+    max_attempts: Final = attempts.stop - 1
+    for attempt in attempts:
         outcome = _attempt_fetch_sync(client=client, url=url, timeout=timeout)
         if not isinstance(outcome, _FetchAttemptRetryable):
             return outcome
@@ -520,6 +536,68 @@ def _finalize_loaded_model_cost_map(loaded: ModelCostMapReloaded) -> ModelCostMa
     return replace(loaded, model_cost_map=_finalize_model_cost_map(loaded.model_cost_map))
 
 
+def adopt_model_cost_map(
+    new_model_cost_map: dict,  # mutable-ok: public API preserves the mutable cost-map contract
+) -> int:
+    import litellm
+    from litellm import utils
+
+    litellm.model_cost = new_model_cost_map
+    utils._invalidate_model_cost_lowercase_map()  # pyright: ignore[reportPrivateUsage]  # required cache invalidation
+    litellm.add_known_models(model_cost_map=new_model_cost_map)
+    fetched_model_count: Final = len(new_model_cost_map) if new_model_cost_map else 0
+    utils.reapply_runtime_model_cost_registrations()
+    return fetched_model_count
+
+
+def _retry_remote_fetch_in_background(
+    url: str,
+    timeout: int,
+    max_attempts: int,
+    sleep: Callable[[float], None],
+    rng: random.Random,
+    client: _SyncGetClient,
+    first_outcome: _FetchAttemptRetryable,
+) -> None:
+    try:
+        first_wait: Final = _next_retry_wait(outcome=first_outcome, attempt=1, max_attempts=max_attempts, rng=rng)
+        if isinstance(first_wait, ModelCostMapReloadUnavailable):
+            return
+        sleep(first_wait)
+        result: Final = _fetch_remote_model_cost_map_with_retry_sync(
+            url=url,
+            timeout=timeout,
+            attempts=range(2, max_attempts + 1),
+            sleep=sleep,
+            rng=rng,
+            client=client,
+        )
+        if isinstance(result, ModelCostMapReloadUnavailable):
+            verbose_logger.warning(
+                "LiteLLM: Failed to fetch remote model cost map from %s after %d attempts; keeping local backup",
+                url,
+                max_attempts,
+            )
+            return
+        _litellm_import_complete.wait()
+        if not GetModelCostMap.validate_model_cost_map(
+            fetched_map=result.model_cost_map,
+            backup_model_count=GetModelCostMap._get_backup_model_count(),  # pyright: ignore[reportPrivateUsage]  # integrity cache
+        ):
+            verbose_logger.warning(
+                "LiteLLM: Fetched model cost map failed integrity check. Using local backup instead. url=%s",
+                url,
+            )
+            return
+        finalized: Final = _finalize_loaded_model_cost_map(result).model_cost_map
+        _cost_map_source_info.source = "remote"
+        _cost_map_source_info.fallback_reason = None
+        _cost_map_source_info.loaded_at = datetime.now(timezone.utc)
+        adopt_model_cost_map(finalized)
+    except Exception as e:  # noqa: BLE001  # a failed background retry must not kill the task; the backup stays
+        verbose_logger.warning("LiteLLM: Background model cost map retry failed: %s", e)
+
+
 def get_model_cost_map(
     url: str,
     timeout: int = 5,
@@ -531,10 +609,12 @@ def get_model_cost_map(
     """
     Public entry point — returns the model cost map dict.
 
-    1. If ``LITELLM_LOCAL_MODEL_COST_MAP`` is set, uses the local backup only.
+    1. If ``LITELLM_LOCAL_MODEL_COST_MAP`` is set or this is a ``lite`` /
+       ``litellm-proxy`` CLI process, uses the local backup only.
     2. Otherwise fetches from ``url``, retrying transient HTTP errors
-       (429/5xx/transport) with Retry-After-aware backoff, validates
-       integrity, and falls back to the local backup on any failure.
+       (429/5xx/transport) with Retry-After-aware backoff in a background
+       thread, validates integrity, and falls back to the local backup on any
+       failure.
 
     Only the backup model count is cached (a single int) for validation.
     The full backup dict is only parsed when it must be *returned* as a
@@ -543,7 +623,7 @@ def get_model_cost_map(
     _cost_map_source_info.loaded_at = datetime.now(timezone.utc)
     # Note: can't use get_secret_bool here — this runs during litellm.__init__
     # before litellm._key_management_settings is set.
-    if os.getenv("LITELLM_LOCAL_MODEL_COST_MAP", "").lower() == "true":
+    if os.getenv("LITELLM_LOCAL_MODEL_COST_MAP", "").lower() == "true" or _is_cli_process():
         _cost_map_source_info.source = "local"
         _cost_map_source_info.url = None
         _cost_map_source_info.is_env_forced = True
@@ -553,24 +633,34 @@ def get_model_cost_map(
     _cost_map_source_info.url = url
     _cost_map_source_info.is_env_forced = False
 
-    result: Final = _fetch_remote_model_cost_map_with_retry_sync(
-        url=url,
-        timeout=timeout,
-        max_attempts=max_attempts,
-        sleep=sleep,
-        rng=rng if rng is not None else random.Random(),
-        client=client if client is not None else httpx,
-    )
-    if isinstance(result, ModelCostMapReloadUnavailable):
+    fetch_client: Final = client if client is not None else httpx
+    fetch_rng: Final = rng if rng is not None else random.Random()
+    outcome: Final = _attempt_fetch_sync(client=fetch_client, url=url, timeout=timeout)
+    if isinstance(outcome, _FetchAttemptRetryable) and max_attempts > 1:
+        threading.Thread(
+            target=_retry_remote_fetch_in_background,
+            kwargs={  # mutable-ok: threading requires a mutable keyword-arguments mapping
+                "url": url,
+                "timeout": timeout,
+                "max_attempts": max_attempts,
+                "sleep": sleep,
+                "rng": fetch_rng,
+                "client": fetch_client,
+                "first_outcome": outcome,
+            },
+            name="litellm-model-cost-map-retry",
+            daemon=True,
+        ).start()
+    if not isinstance(outcome, ModelCostMapReloaded):
         verbose_logger.warning(
             "LiteLLM: Failed to fetch remote model cost map from %s: %s. Falling back to local backup.",
             url,
-            result.reason,
+            outcome.reason,
         )
         _cost_map_source_info.source = "local"
-        _cost_map_source_info.fallback_reason = f"Remote fetch failed: {result.reason}"
+        _cost_map_source_info.fallback_reason = f"Remote fetch failed: {outcome.reason}"
         return _finalize_loaded_model_cost_map(GetModelCostMap.load_local_model_cost_map_with_revision()).model_cost_map
-    content: Final = result.model_cost_map
+    content: Final = outcome.model_cost_map
 
     # Validate using cached count (cheap int comparison, no file I/O)
     if not GetModelCostMap.validate_model_cost_map(
@@ -587,4 +677,4 @@ def get_model_cost_map(
 
     _cost_map_source_info.source = "remote"
     _cost_map_source_info.fallback_reason = None
-    return _finalize_loaded_model_cost_map(result).model_cost_map
+    return _finalize_loaded_model_cost_map(outcome).model_cost_map
diff --git a/litellm/litellm_core_utils/litellm_logging.py b/litellm/litellm_core_utils/litellm_logging.py
index b0d6db20b31..6ee68ab21c5 100644
--- a/litellm/litellm_core_utils/litellm_logging.py
+++ b/litellm/litellm_core_utils/litellm_logging.py
@@ -17,7 +17,7 @@ from types import MappingProxyType, TracebackType
 from typing import TYPE_CHECKING, Any, Final, Literal, Optional, Union, cast
 
 from httpx import Response
-from pydantic import BaseModel
+from pydantic import BaseModel, JsonValue
 
 import litellm
 from litellm import (
@@ -42,6 +42,7 @@ from litellm.caching.caching_handler import LLMCachingHandler
 from litellm.constants import (
     DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
     DEFAULT_MOCK_RESPONSE_PROMPT_TOKEN_COUNT,
+    EMPTY_MAPPING,
     PROVIDER_REQUEST_ID_HEADERS,
     SENTRY_DENYLIST,
     SENTRY_PII_DENYLIST,
@@ -64,6 +65,11 @@ from litellm.integrations.custom_logger import CustomLogger
 from litellm.integrations.deepeval.deepeval import DeepEvalLogger
 from litellm.integrations.mlflow import MlflowLogger
 from litellm.integrations.sqs import SQSLogger
+from litellm.litellm_core_utils.classifier_logging import (
+    classifier_audit_fields,
+    classifier_input_snapshot,
+    is_classifier_call,
+)
 from litellm.litellm_core_utils.core_helpers import is_expected_client_error, reconstruct_model_name
 from litellm.litellm_core_utils.get_litellm_params import get_litellm_params
 from litellm.litellm_core_utils.internal_call_metadata import (
@@ -89,6 +95,7 @@ from litellm.litellm_core_utils.redact_messages import (
     redact_message_input_output_from_custom_logger,
     redact_message_input_output_from_logging,
     redact_streaming_responses_for_custom_logger,
+    should_redact_message_logging,
 )
 from litellm.llms.base_llm.ocr.transformation import OCRResponse
 from litellm.llms.base_llm.search.transformation import SearchResponse
@@ -120,7 +127,6 @@ from litellm.types.utils import (
     CachingDetails,
     CallTypes,
     CostBreakdown,
-    CostResponseTypes,
     CustomPricingLiteLLMParams,
     DynamicPromptManagementParamLiteral,
     EmbeddingResponse,
@@ -183,6 +189,7 @@ from ..integrations.lunary import LunaryLogger
 from ..integrations.newrelic import NewRelicLogger
 from ..integrations.openmeter import OpenMeterLogger
 from ..integrations.opik.opik import OpikLogger
+from ..integrations.pointfive import PointFiveLogger
 from ..integrations.posthog import PostHogLogger
 from ..integrations.prompt_layer import PromptLayerLogger
 from ..integrations.s3 import S3Logger
@@ -203,7 +210,8 @@ if TYPE_CHECKING:
 
     from litellm.integrations.otel.logger import OpenTelemetryV2
     from litellm.integrations.otel.model.config import ExporterSpec, OpenTelemetryV2Config
-    from litellm.llms.base_llm.passthrough.transformation import BasePassthroughConfig
+    from litellm.litellm_core_utils.llm_cost_calc.utils import BilledTokenRates
+    from litellm.llms.base_llm.passthrough.transformation import BasePassthroughConfig, LoggedRelayResponse
 try:
     from litellm_enterprise.enterprise_callbacks.callback_controls import (
         EnterpriseCallbackControls,
@@ -287,6 +295,9 @@ def _get_provider_request_id(original_exception: Exception) -> str | None:
 # Cache custom pricing keys as frozenset for O(1) lookups instead of looping through 49 keys
 _CUSTOM_PRICING_KEYS: Final[frozenset[str]] = frozenset(CustomPricingLiteLLMParams.model_fields.keys())
 _MODEL_INFO_CUSTOM_PRICING_KEYS: Final[frozenset[str]] = _CUSTOM_PRICING_KEYS | DEPLOYMENT_SCOPED_PRICING_FIELDS
+_UNSERIALIZABLE_METADATA_KEYS: Final[frozenset[str]] = frozenset(
+    ("user_api_key_auth", "user_api_key_budget_reservation")
+)
 
 sentry_sdk_instance = None
 capture_exception = None
@@ -472,6 +483,7 @@ class Logging(LiteLLMLoggingBaseClass):
     stream_options = None
     litellm_request_debug: bool = False
     streamed_anthropic_message_id: str | None = None
+    classifier_input: Mapping[str, JsonValue] | None = None
 
     def __init__(
         self,
@@ -590,6 +602,7 @@ class Logging(LiteLLMLoggingBaseClass):
 
         # Initialize cost breakdown field
         self.cost_breakdown: CostBreakdown | None = None
+        self.billed_token_rates: BilledTokenRates | None = None
 
         # Init Caching related details
         self.caching_details: CachingDetails | None = None
@@ -1209,6 +1222,14 @@ class Logging(LiteLLMLoggingBaseClass):
         self.model_call_details["api_key"] = api_key
         self.model_call_details["additional_args"] = additional_args
         self.model_call_details["log_event_type"] = "pre_api_call"
+        if is_classifier_call(self.call_type, self.model_call_details.get("litellm_params") or EMPTY_MAPPING):
+            self.classifier_input = (
+                None
+                if should_redact_message_logging(self.model_call_details)
+                else classifier_input_snapshot(
+                    additional_args.get("complete_input_dict"), openai_sdk=additional_args.get("openai_sdk") is True
+                )
+            )
         if model:  # if model name was changes pre-call, overwrite the initial model call name with the new one
             self.model_call_details["model"] = model
         self.model_call_details["litellm_params"]["api_base"] = self._get_masked_api_base(
@@ -1587,6 +1608,7 @@ class Logging(LiteLLMLoggingBaseClass):
         service_tier: str | None = None,
         data_residency: str | None = None,
         vertex_location: str | None = None,
+        billed_token_rates: "BilledTokenRates | None" = None,
     ) -> None:
         """
         Helper method to store cost breakdown in the logging object.
@@ -1606,8 +1628,10 @@ class Logging(LiteLLMLoggingBaseClass):
             service_tier: Tier the costs above were priced on, already resolved
             data_residency: Region uplift the costs above were priced on, already resolved
             vertex_location: Vertex AI location the costs above were priced on, already resolved
+            billed_token_rates: Per-token rates the costs above were billed at, already resolved
         """
 
+        self.billed_token_rates = billed_token_rates
         self.cost_breakdown = CostBreakdown(
             input_cost=input_cost,
             output_cost=output_cost,
@@ -2376,7 +2400,7 @@ class Logging(LiteLLMLoggingBaseClass):
         self,
         raw_bytes: list[bytes],
         provider_config: "BasePassthroughConfig",
-    ) -> Optional["CostResponseTypes"]:
+    ) -> Optional["LoggedRelayResponse"]:
         all_chunks: Final = provider_config._convert_raw_bytes_to_str_lines(raw_bytes)
         complete_streaming_response: Final = provider_config.handle_logging_collected_chunks(
             all_chunks=all_chunks,
@@ -4372,6 +4396,14 @@ def _init_custom_logger_compatible_class(
             _s3_v2_logger: Final = S3V2Logger()
             _in_memory_loggers.append(_s3_v2_logger)
             return _s3_v2_logger
+        elif logging_integration == "pointfive":
+            for callback in _in_memory_loggers:
+                if isinstance(callback, PointFiveLogger):
+                    return callback
+
+            _pointfive_logger: Final = PointFiveLogger()
+            _in_memory_loggers.append(_pointfive_logger)
+            return _pointfive_logger
         elif logging_integration == "aws_sqs":
             for callback in _in_memory_loggers:
                 if isinstance(callback, SQSLogger):
@@ -5060,6 +5092,10 @@ def get_custom_logger_compatible_class(
             for callback in _in_memory_loggers:
                 if isinstance(callback, S3V2Logger):
                     return callback
+        elif logging_integration == "pointfive":
+            for callback in _in_memory_loggers:
+                if isinstance(callback, PointFiveLogger):
+                    return callback
         elif logging_integration == "aws_sqs":
             for callback in _in_memory_loggers:
                 if isinstance(callback, SQSLogger):
@@ -5353,23 +5389,23 @@ class StandardLoggingPayloadSetup:
         Returns:
             dict: Merged metadata with user API key fields taking precedence
         """
-        merged_metadata: Final[dict] = {}
-
-        # Start with metadata (user API key fields) - but skip non-serializable objects
-        if litellm_params.get("metadata") and isinstance(litellm_params.get("metadata"), dict):
-            for key, value in litellm_params["metadata"].items():
-                # Skip non-serializable objects like UserAPIKeyAuth
-                if key in {"user_api_key_auth", "user_api_key_budget_reservation"}:
-                    continue
-                merged_metadata[key] = value
-
-        # Then merge litellm_metadata (model-related fields) - this will NOT overwrite existing keys
-        if litellm_params.get("litellm_metadata") and isinstance(litellm_params.get("litellm_metadata"), dict):
-            for key, value in litellm_params["litellm_metadata"].items():
-                if key not in merged_metadata:  # Don't overwrite existing keys from metadata
-                    merged_metadata[key] = value
-
-        return merged_metadata
+        metadata: Final = litellm_params.get("metadata")
+        litellm_metadata: Final = litellm_params.get("litellm_metadata")
+        user_metadata: Final = MappingProxyType(
+            {
+                key: value
+                for key, value in (metadata.copy().items() if isinstance(metadata, dict) else ())
+                if key not in _UNSERIALIZABLE_METADATA_KEYS
+            }
+        )
+        model_metadata: Final = MappingProxyType(
+            {
+                key: value
+                for key, value in (litellm_metadata.copy().items() if isinstance(litellm_metadata, dict) else ())
+                if key not in user_metadata
+            }
+        )
+        return {**user_metadata, **model_metadata}  # mutable-ok: function contract returns a plain dict
 
     @staticmethod
     def get_standard_logging_metadata(
@@ -5627,7 +5663,7 @@ class StandardLoggingPayloadSetup:
                     additional_logging_headers[key] = additiona_headers[_key]
 
         # Preserve all remaining headers verbatim (e.g. llm_provider-x-request-id)
-        for k, v in additiona_headers.items():
+        for k, v in additiona_headers.copy().items():
             if k.lower() not in typed_keys:
                 additional_logging_headers[k] = v
 
@@ -6276,6 +6312,18 @@ def get_standard_logging_object_payload(
         )
 
         payload: Final[StandardLoggingPayload] = StandardLoggingPayload(
+            **(
+                classifier_audit_fields(
+                    MappingProxyType(
+                        {
+                            "classifier_input": logging_obj.classifier_input,
+                            "originating_request_masked": proxy_server_request.get("originating_request_masked"),
+                        }
+                    )
+                )
+                if is_classifier_call(call_type or "", litellm_params) and not should_redact_message_logging(kwargs)
+                else EMPTY_MAPPING
+            ),
             id=str(id),
             litellm_call_id=kwargs.get("litellm_call_id") or litellm_params.get("litellm_call_id"),
             trace_id=StandardLoggingPayloadSetup.get_standard_logging_payload_trace_id(
diff --git a/litellm/litellm_core_utils/llm_cost_calc/utils.py b/litellm/litellm_core_utils/llm_cost_calc/utils.py
index c05d4c29a5e..e5977ca4156 100644
--- a/litellm/litellm_core_utils/llm_cost_calc/utils.py
+++ b/litellm/litellm_core_utils/llm_cost_calc/utils.py
@@ -10,6 +10,7 @@ from typing import Any, Final, Literal, TypedDict, cast
 from zoneinfo import ZoneInfo, ZoneInfoNotFoundError
 
 import litellm
+from litellm._internal_context import current_billing_time
 from litellm._logging import verbose_logger
 from litellm.litellm_core_utils.llm_cost_calc.tiered_pricing import (
     select_tier_for_input,
@@ -19,6 +20,7 @@ from litellm.types.utils import (
     CacheCreationTokenDetails,
     CallTypes,
     CompletionTokensDetailsWrapper,
+    CostPerToken,
     DataResidency,
     ImageResponse,
     ModelInfo,
@@ -305,7 +307,7 @@ def _is_within_off_peak_window(off_peak_hours_utc: str | Sequence[str], current_
     than being localised, so callers must pass datetime.now(timezone.utc), never datetime.now(),
     or every window shifts by the host's offset.
     """
-    reference: Final = current_time if current_time is not None else datetime.now(timezone.utc)
+    reference: Final = current_time if current_time is not None else current_billing_time()
     now: Final = (reference.astimezone(timezone.utc) if reference.tzinfo is not None else reference).time()
     windows: Final = (off_peak_hours_utc,) if isinstance(off_peak_hours_utc, str) else off_peak_hours_utc
     for window in windows:
@@ -392,7 +394,7 @@ def _is_off_peak(off_peak: Mapping[str, object], current_time: datetime | None =
     rules: the flat hours_utc windows, which apply every day, or any entry in windows, whose
     hours apply only on its weekdays.
     """
-    reference: Final = current_time if current_time is not None else datetime.now(timezone.utc)
+    reference: Final = current_time if current_time is not None else current_billing_time()
     reference_utc: Final = (
         reference.astimezone(timezone.utc) if reference.tzinfo is not None else reference.replace(tzinfo=timezone.utc)
     )
@@ -1195,7 +1197,7 @@ def generic_cost_per_token(
             usage.prompt_tokens - cache_hit - audio_tokens - cache_creation - image_tokens - video_tokens, 0
         )
 
-    billing_time: Final = current_time if current_time is not None else datetime.now(timezone.utc)
+    billing_time: Final = current_time if current_time is not None else current_billing_time()
     (
         prompt_base_cost,
         completion_base_cost,
@@ -1309,42 +1311,90 @@ def _coerce_token_count(value: object) -> int:
     return value if isinstance(value, int) and value > 0 else 0
 
 
+@dataclass(frozen=True, slots=True)
+class BilledTokenRates:
+    """Per-token rates one request's usage bills at, after token tiers, off-peak windows and the
+    regional multipliers the totals apply, so each cost line equals its token count times its rate."""
+
+    input_cost_per_token: float
+    output_cost_per_token: float
+    cache_read_input_token_cost: float
+    cache_creation_input_token_cost: float
+    cache_creation_input_token_cost_above_1hr: float
+    output_cost_per_reasoning_token: float
+
+    def scaled(self, multiplier: float) -> "BilledTokenRates":
+        if multiplier == 1.0:
+            return self
+        return BilledTokenRates(
+            input_cost_per_token=self.input_cost_per_token * multiplier,
+            output_cost_per_token=self.output_cost_per_token * multiplier,
+            cache_read_input_token_cost=self.cache_read_input_token_cost * multiplier,
+            cache_creation_input_token_cost=self.cache_creation_input_token_cost * multiplier,
+            cache_creation_input_token_cost_above_1hr=self.cache_creation_input_token_cost_above_1hr * multiplier,
+            output_cost_per_reasoning_token=self.output_cost_per_reasoning_token * multiplier,
+        )
+
+
 @dataclass(frozen=True, slots=True)
 class TokenTypeCostBreakdown:
     reasoning_cost: float
     cache_read_cost: float
     cache_creation_cost: float
+    rates: BilledTokenRates | None = None
+    """Rates these lines were billed at, so a caller reporting both cannot resolve them a second,
+    differently-argued way. None when the model's pricing could not be resolved."""
 
 
-def get_token_type_cost_breakdown(
-    model: str,
-    custom_llm_provider: str | None,
+def _reasoning_token_count(usage: Usage) -> int:
+    parsed: Final = (
+        parse_completion_tokens_details(usage)["reasoning_tokens"] if usage.completion_tokens_details is not None else 0
+    )
+    return parsed or _coerce_token_count(getattr(usage, "reasoning_tokens", 0))
+
+
+def _cache_token_counts(usage: Usage) -> tuple[int, int, CacheCreationTokenDetails | None]:
+    """(cache read tokens, cache creation tokens, cache creation details): read from prompt_tokens_details
+    first, then the private top-level counters the Usage constructor mirrors cache tokens onto for
+    providers/callers that bypass the details."""
+    parsed: Final = parse_prompt_tokens_details(usage) if usage.prompt_tokens_details is not None else None
+    parsed_read: Final = parsed["cache_hit_tokens"] if parsed is not None else 0
+    parsed_creation: Final = parsed["cache_creation_tokens"] if parsed is not None else 0
+    return (
+        parsed_read or _coerce_token_count(getattr(usage, "_cache_read_input_tokens", 0)),
+        parsed_creation or _coerce_token_count(getattr(usage, "_cache_creation_input_tokens", 0)),
+        parsed["cache_creation_token_details"] if parsed is not None else None,
+    )
+
+
+def _custom_pricing_rates(custom_cost_per_token: CostPerToken) -> BilledTokenRates:
+    """Flat custom pricing has no tiers, uplifts or reasoning rate: cache tokens bill at the configured
+    cache rates (else the input rate) and reasoning at the output rate, as _cost_per_token_custom_pricing_helper does."""
+    input_rate: Final = custom_cost_per_token["input_cost_per_token"]
+    output_rate: Final = custom_cost_per_token["output_cost_per_token"]
+    cache_creation_rate: Final = custom_cost_per_token.get("cache_creation_input_token_cost", input_rate)
+    return BilledTokenRates(
+        input_cost_per_token=input_rate,
+        output_cost_per_token=output_rate,
+        cache_read_input_token_cost=custom_cost_per_token.get("cache_read_input_token_cost", input_rate),
+        cache_creation_input_token_cost=cache_creation_rate,
+        cache_creation_input_token_cost_above_1hr=cache_creation_rate,
+        output_cost_per_reasoning_token=output_rate,
+    )
+
+
+def _cost_map_billed_rates(
+    model_info: ModelInfo,
     usage: Usage,
-    service_tier: str | None = None,
-    data_residency: str | None = None,
-    vertex_location: str | None = None,
-    current_time: datetime | None = None,
-) -> TokenTypeCostBreakdown:
-    """
-    Provider-agnostic cost of reasoning and cache tokens, derived from the usage
-    object and model pricing alone.
-
-    This works for every provider, including Perplexity/Cerebras/Dashscope whose
-    cost calculators bypass ``generic_cost_per_token``, because cache tokens always
-    land on ``prompt_tokens_details`` (via the Usage constructor and provider
-    transformations) and reasoning tokens on ``completion_tokens_details``. It reuses
-    the same rate-resolution primitives as the total-cost path so the breakdown can
-    never drift from the totals. Returns zeros (never raises) when the model or its
-    pricing cannot be resolved.
-    """
-    try:
-        model_info: Final = get_model_info(model=model, custom_llm_provider=custom_llm_provider)
-    except Exception:
-        return TokenTypeCostBreakdown(0.0, 0.0, 0.0)
-
-    billing_time: Final = current_time if current_time is not None else datetime.now(timezone.utc)
+    custom_llm_provider: str | None,
+    service_tier: str | None,
+    data_residency: str | None,
+    vertex_location: str | None,
+    current_time: datetime | None,
+) -> BilledTokenRates:
+    billing_time: Final = current_time if current_time is not None else current_billing_time()
     (
-        _prompt_base_cost,
+        prompt_base_cost,
         completion_base_cost,
         cache_creation_cost_rate,
         cache_creation_cost_above_1hr_rate,
@@ -1356,13 +1406,6 @@ def get_token_type_cost_breakdown(
         current_time=billing_time,
         threshold_is_inclusive=_uses_inclusive_token_thresholds(custom_llm_provider),
     )
-
-    reasoning_tokens = (
-        parse_completion_tokens_details(usage)["reasoning_tokens"] if usage.completion_tokens_details is not None else 0
-    )
-    if not reasoning_tokens:
-        reasoning_tokens = _coerce_token_count(getattr(usage, "reasoning_tokens", 0))
-
     reasoning_rate: Final = _resolve_billed_reasoning_rate(
         model_info=model_info,
         usage=usage,
@@ -1370,57 +1413,103 @@ def get_token_type_cost_breakdown(
         completion_base_cost=completion_base_cost,
         current_time=billing_time,
     )
-    reasoning_cost = float(reasoning_tokens) * reasoning_rate
+    multiplier: Final = (
+        _get_regional_uplift_multiplier(model_info, data_residency)
+        * get_vertex_regional_endpoint_uplift(model_info, vertex_location)
+        * get_provider_specific_geo_multiplier(model_info=model_info, usage=usage)
+    )
+    return BilledTokenRates(
+        input_cost_per_token=prompt_base_cost,
+        output_cost_per_token=completion_base_cost,
+        cache_read_input_token_cost=cache_read_cost_rate,
+        cache_creation_input_token_cost=cache_creation_cost_rate,
+        cache_creation_input_token_cost_above_1hr=cache_creation_cost_above_1hr_rate,
+        output_cost_per_reasoning_token=reasoning_rate,
+    ).scaled(multiplier)
 
-    cache_read_tokens = 0
-    cache_creation_tokens = 0
-    cache_creation_token_details: CacheCreationTokenDetails | None = None
-    if usage.prompt_tokens_details is not None:
-        prompt_tokens_details: Final = parse_prompt_tokens_details(usage)
-        cache_read_tokens = prompt_tokens_details["cache_hit_tokens"]
-        cache_creation_tokens = prompt_tokens_details["cache_creation_tokens"]
-        cache_creation_token_details = prompt_tokens_details["cache_creation_token_details"]
-    # Fall back to the private top-level counters the Usage constructor mirrors cache
-    # tokens onto, so providers/callers that bypass prompt_tokens_details are covered.
-    if not cache_read_tokens:
-        cache_read_tokens = _coerce_token_count(getattr(usage, "_cache_read_input_tokens", 0))
-    if not cache_creation_tokens:
-        cache_creation_tokens = _coerce_token_count(getattr(usage, "_cache_creation_input_tokens", 0))
 
-    cache_read_cost = float(cache_read_tokens) * cache_read_cost_rate
-    cache_creation_cost = calculate_cache_writing_cost(
-        cache_creation_tokens=cache_creation_tokens,
-        cache_creation_token_details=cache_creation_token_details,
-        cache_creation_cost_above_1hr=cache_creation_cost_above_1hr_rate,
-        cache_creation_cost=cache_creation_cost_rate,
+def get_billed_token_rates(
+    model: str,
+    custom_llm_provider: str | None,
+    usage: Usage,
+    service_tier: str | None = None,
+    data_residency: str | None = None,
+    vertex_location: str | None = None,
+    current_time: datetime | None = None,
+    custom_cost_per_token: CostPerToken | None = None,
+) -> BilledTokenRates | None:
+    """Rates the cost calculator bills ``usage`` at, resolved exactly as the totals and the token-type
+    breakdown resolve them. None when the model's pricing cannot be resolved."""
+    if custom_cost_per_token is not None:
+        return _custom_pricing_rates(custom_cost_per_token)
+    try:
+        model_info: Final = get_model_info(model=model, custom_llm_provider=custom_llm_provider)
+    except Exception:  # noqa: BLE001  # get_model_info raises a bare Exception for an unmapped model: no rates
+        return None
+    return _cost_map_billed_rates(
+        model_info=model_info,
+        usage=usage,
+        custom_llm_provider=custom_llm_provider,
+        service_tier=service_tier,
+        data_residency=data_residency,
+        vertex_location=vertex_location,
+        current_time=current_time,
     )
 
-    # Apply the same flat regional-processing uplift the totals get, so per-type
-    # costs stay reconciled with input_cost/output_cost for regionalized OpenAI hosts.
-    uplift: Final = _get_regional_uplift_multiplier(model_info, data_residency)
-    if uplift != 1.0:
-        reasoning_cost *= uplift
-        cache_read_cost *= uplift
-        cache_creation_cost *= uplift
 
-    vertex_uplift: Final = get_vertex_regional_endpoint_uplift(model_info, vertex_location)
-    if vertex_uplift != 1.0:
-        reasoning_cost *= vertex_uplift
-        cache_read_cost *= vertex_uplift
-        cache_creation_cost *= vertex_uplift
+def get_token_type_cost_breakdown(
+    model: str,
+    custom_llm_provider: str | None,
+    usage: Usage,
+    service_tier: str | None = None,
+    data_residency: str | None = None,
+    vertex_location: str | None = None,
+    current_time: datetime | None = None,
+    custom_cost_per_token: CostPerToken | None = None,
+) -> TokenTypeCostBreakdown:
+    """
+    Provider-agnostic cost of reasoning and cache tokens, derived from the usage
+    object and model pricing alone.
 
-    # Mirror the provider-specific geo uplift (e.g. Anthropic us: 1.1) the totals
-    # apply, so cache and reasoning line items stay reconciled with them.
-    geo_multiplier: Final = get_provider_specific_geo_multiplier(model_info=model_info, usage=usage)
-    if geo_multiplier != 1.0:
-        reasoning_cost *= geo_multiplier
-        cache_read_cost *= geo_multiplier
-        cache_creation_cost *= geo_multiplier
+    This works for every provider, including Perplexity/Cerebras/Dashscope whose
+    cost calculators bypass ``generic_cost_per_token``, because cache tokens always
+    land on ``prompt_tokens_details`` (via the Usage constructor and provider
+    transformations) and reasoning tokens on ``completion_tokens_details``. It reuses
+    the same rate resolution as the total-cost path (``get_billed_token_rates``) so the
+    breakdown can never drift from the totals. A deployment billed by
+    ``custom_cost_per_token`` is priced from those flat rates instead of the cost map and,
+    like its totals, bills cache writes flat rather than by their 5m/1h split.
+    Returns zeros (never raises) when the model or its pricing cannot be resolved.
+    """
+    rates: Final = get_billed_token_rates(
+        model=model,
+        custom_llm_provider=custom_llm_provider,
+        usage=usage,
+        service_tier=service_tier,
+        data_residency=data_residency,
+        vertex_location=vertex_location,
+        current_time=current_time,
+        custom_cost_per_token=custom_cost_per_token,
+    )
+    if rates is None:
+        return TokenTypeCostBreakdown(0.0, 0.0, 0.0)
 
+    cache_read_tokens, cache_creation_tokens, cache_creation_token_details = _cache_token_counts(usage)
+    cache_creation_cost: Final = (
+        float(cache_creation_tokens) * rates.cache_creation_input_token_cost
+        if custom_cost_per_token is not None
+        else calculate_cache_writing_cost(
+            cache_creation_tokens=cache_creation_tokens,
+            cache_creation_token_details=cache_creation_token_details,
+            cache_creation_cost_above_1hr=rates.cache_creation_input_token_cost_above_1hr,
+            cache_creation_cost=rates.cache_creation_input_token_cost,
+        )
+    )
     return TokenTypeCostBreakdown(
-        reasoning_cost=reasoning_cost,
-        cache_read_cost=cache_read_cost,
+        reasoning_cost=float(_reasoning_token_count(usage)) * rates.output_cost_per_reasoning_token,
+        cache_read_cost=float(cache_read_tokens) * rates.cache_read_input_token_cost,
         cache_creation_cost=cache_creation_cost,
+        rates=rates,
     )
 
 
diff --git a/litellm/litellm_core_utils/llm_response_utils/convert_dict_to_response.py b/litellm/litellm_core_utils/llm_response_utils/convert_dict_to_response.py
index a6f10e1ede3..87524d86c61 100644
--- a/litellm/litellm_core_utils/llm_response_utils/convert_dict_to_response.py
+++ b/litellm/litellm_core_utils/llm_response_utils/convert_dict_to_response.py
@@ -3,7 +3,7 @@ import json
 import re
 import time
 import traceback
-from collections.abc import Iterable, Sequence
+from collections.abc import Mapping, Sequence
 from typing import Final, Literal, cast
 
 import litellm
@@ -151,6 +151,16 @@ def _clear_later_replay_slice_metadata(choice: StreamingChoices) -> None:
         del choice.enhancements
 
 
+def _invalid_choices_message(response_object: Mapping[str, object]) -> str:
+    raw_keys: Final = list(response_object.keys())
+    if "choices" not in response_object:
+        return f"LiteLLM: provider returned a response with no 'choices'. Raw keys: {raw_keys}"
+    return (
+        f"LiteLLM: provider returned 'choices' that is not a list ({type(response_object['choices']).__name__}). "
+        f"Raw keys: {raw_keys}"
+    )
+
+
 async def convert_to_streaming_response_async(
     response_object: dict | None = None,
 ):
@@ -179,14 +189,12 @@ async def convert_to_streaming_response_async(
 
     choice_list: Final[list[StreamingChoices]] = []
 
-    if not response_object.get("choices"):
+    if not isinstance(response_object.get("choices"), list):
         from litellm.exceptions import APIError
 
         raise APIError(
             status_code=500,
-            message=(
-                f"LiteLLM: provider returned a response with no 'choices'. Raw keys: {list(response_object.keys())}"
-            ),
+            message=_invalid_choices_message(response_object),
             llm_provider="",
             model="",
         )
@@ -287,14 +295,12 @@ def convert_to_streaming_response(
     model_response_object: Final = ModelResponseStream()
     choice_list: Final[list[StreamingChoices]] = []
 
-    if not response_object.get("choices"):
+    if not isinstance(response_object.get("choices"), list):
         from litellm.exceptions import APIError
 
         raise APIError(
             status_code=500,
-            message=(
-                f"LiteLLM: provider returned a response with no 'choices'. Raw keys: {list(response_object.keys())}"
-            ),
+            message=_invalid_choices_message(response_object),
             llm_provider="",
             model="",
         )
@@ -623,15 +629,12 @@ def convert_to_model_response_object(
                 return convert_to_streaming_response(response_object=response_object)
             choice_list: Final[list[Choices]] = []
 
-            if not response_object.get("choices") or not isinstance(response_object["choices"], Iterable):
+            if not isinstance(response_object.get("choices"), list):
                 from litellm.exceptions import APIError
 
                 raise APIError(
                     status_code=500,
-                    message=(
-                        "LiteLLM: provider returned a response with no 'choices'. "
-                        f"Raw keys: {list(response_object.keys())}"
-                    ),
+                    message=_invalid_choices_message(response_object),
                     llm_provider="",
                     model="",
                 )
diff --git a/litellm/litellm_core_utils/logging_callback_manager.py b/litellm/litellm_core_utils/logging_callback_manager.py
index 9b612993a69..31523c9309d 100644
--- a/litellm/litellm_core_utils/logging_callback_manager.py
+++ b/litellm/litellm_core_utils/logging_callback_manager.py
@@ -441,7 +441,15 @@ class LoggingCallbackManager:
 
         return result
 
+    def get_callback_objects(self) -> tuple[tuple[str, CustomLogger | Callable], ...]:
+        return tuple(
+            (self._get_callback_string(callback), callback)
+            for callback in self._get_all_callbacks()
+            if not isinstance(callback, str)
+        )
+
     def _get_callback_string(self, callback: CustomLogger | Callable | str) -> str:
+        from litellm.integrations.opentelemetry import OpenTelemetry
         from litellm.litellm_core_utils.custom_logger_registry import (
             CustomLoggerRegistry,
         )
@@ -449,6 +457,8 @@ class LoggingCallbackManager:
         """Convert a callback to its string representation"""
         if isinstance(callback, str):
             return callback
+        elif isinstance(callback, OpenTelemetry) and callback.callback_name is not None:
+            return callback.callback_name
         elif isinstance(callback, CustomLogger):
             # Try to get the string representation from the registry
             callback_str: Final = CustomLoggerRegistry.get_callback_str_from_class_type(type(callback))
diff --git a/litellm/litellm_core_utils/prompt_templates/common_utils.py b/litellm/litellm_core_utils/prompt_templates/common_utils.py
index 00b80839dde..2485896184e 100644
--- a/litellm/litellm_core_utils/prompt_templates/common_utils.py
+++ b/litellm/litellm_core_utils/prompt_templates/common_utils.py
@@ -6,8 +6,8 @@ import io
 import json
 import mimetypes
 import re
-from collections.abc import Iterable, Mapping, Sequence
-from itertools import groupby
+from collections.abc import Callable, Iterable, Iterator, Mapping, Sequence
+from itertools import groupby, islice
 from os import PathLike
 from pathlib import Path
 from types import MappingProxyType
@@ -1320,17 +1320,128 @@ def flatten_top_level_schema_combinators(schema: Mapping[str, object]) -> Mappin
     return _flatten_schema_against_root(schema, schema, frozenset(), 0, {})  # mutable-ok: fresh per-call $ref memo
 
 
-def tool_with_flattened_parameters(tool: Mapping[str, object]) -> Mapping[str, object]:
+_SUBSCHEMA_KEYWORDS: Final = frozenset(
+    {
+        "additionalItems",
+        "additionalProperties",
+        "contains",
+        "else",
+        "if",
+        "items",
+        "not",
+        "propertyNames",
+        "then",
+        "unevaluatedItems",
+        "unevaluatedProperties",
+    }
+)
+_SUBSCHEMA_LIST_KEYWORDS: Final = frozenset({"allOf", "anyOf", "items", "oneOf", "prefixItems"})
+_SUBSCHEMA_MAP_KEYWORDS: Final = frozenset(
+    {"$defs", "definitions", "dependentSchemas", "patternProperties", "properties"}
+)
+
+_MAX_SCHEMA_NESTING: Final = 1024
+
+
+def drop_non_python_regex_patterns(schema: Mapping[str, object]) -> Mapping[str, object]:
+    """Drop every regex in a schema position that Python's ``re`` cannot compile.
+
+    OpenAI validates tool ``parameters`` against the 2020-12 metaschema with
+    ``jsonschema``'s format checker, which hands each ``pattern`` value and each
+    ``patternProperties`` key to ``re.compile``, so a regex written for an
+    ECMA-262 engine (Unicode property escapes such as ``\\p{Cc}``, as in Claude
+    Code's ``Artifact`` tool) is refused with "'...' is not a 'regex'" by every
+    model family on both the chat and Responses wires. Only schema positions are
+    walked (properties, items, combinators, ``$defs`` and the other applicators),
+    so a ``pattern`` key inside ``default``, ``examples``, ``const`` or vendor
+    extensions is data and stays. Outside strict mode the keyword is only a
+    hint, so dropping it costs the model a constraint and the caller nothing.
+    Compilable regexes and everything else pass through, the input is never
+    mutated, and the same object comes back when nothing was dropped. The walk
+    is level-order rather than recursive, rebuilt deepest level first, and stops
+    at more schema levels than a JSON parser admits, so a cyclic schema built in
+    code cannot spin it.
+    """
+    rebuilt: dict[int, Mapping[str, object]] = {}  # mutable-ok: per-call memo of rewritten nodes, deepest level first
+    for level in reversed(tuple(islice(_schema_levels(schema), _MAX_SCHEMA_NESTING))):
+        rebuilt.update(
+            (id(node), rewritten)
+            for node in level
+            if (rewritten := _node_without_non_python_regex(node, rebuilt)) is not node
+        )
+    return rebuilt.get(id(schema), schema)
+
+
+def _schema_levels(schema: Mapping[str, object]) -> Iterator[tuple[Mapping[str, object], ...]]:
+    frontier: tuple[Mapping[str, object], ...] = (schema,)  # rebind-ok: level-order cursor, one level a round
+    while frontier:
+        yield frontier
+        frontier = tuple(child for node in frontier for child in _subschemas(node))
+
+
+def _subschemas(node: Mapping[str, object]) -> Iterator[Mapping[str, object]]:
+    for key, value in node.items():
+        if key in _SUBSCHEMA_MAP_KEYWORDS and isinstance(value, dict):
+            yield from (sub for sub in value.values() if isinstance(sub, dict))
+        elif key in _SUBSCHEMA_LIST_KEYWORDS and isinstance(value, list):
+            yield from (sub for sub in value if isinstance(sub, dict))
+        elif key in _SUBSCHEMA_KEYWORDS and isinstance(value, dict):
+            yield value
+
+
+def _node_without_non_python_regex(
+    node: Mapping[str, object], rebuilt: Mapping[int, Mapping[str, object]]
+) -> Mapping[str, object]:
+    kept: Final = {  # mutable-ok: tool parameters are JSON dicts
+        key: _keyword_value_rebuilt(key, value, rebuilt)
+        for key, value in node.items()
+        if key != "pattern" or not isinstance(value, str) or _is_python_regex(value)
+    }
+    return node if len(kept) == len(node) and all(kept[key] is node[key] for key in kept) else kept
+
+
+def _keyword_value_rebuilt(key: str, value: object, rebuilt: Mapping[int, Mapping[str, object]]) -> object:
+    if key in _SUBSCHEMA_MAP_KEYWORDS and isinstance(value, dict):
+        kept: Final = {  # mutable-ok: tool parameters are JSON dicts
+            name: rebuilt.get(id(sub), sub)
+            for name, sub in value.items()
+            if key != "patternProperties" or not isinstance(name, str) or _is_python_regex(name)
+        }
+        return value if len(kept) == len(value) and all(kept[name] is value[name] for name in kept) else kept
+    if key in _SUBSCHEMA_LIST_KEYWORDS and isinstance(value, list):
+        items: Final = [rebuilt.get(id(sub), sub) for sub in value]  # mutable-ok: tool parameters are JSON lists
+        return value if all(new is old for new, old in zip(items, value, strict=True)) else items
+    if key in _SUBSCHEMA_KEYWORDS and isinstance(value, dict):
+        return rebuilt.get(id(value), value)
+    return value
+
+
+def _is_python_regex(pattern: str) -> bool:
+    try:
+        re.compile(pattern)
+    except (re.error, RecursionError):
+        return False
+    return True
+
+
+def flatten_combinators_and_drop_non_python_regex_patterns(schema: Mapping[str, object]) -> Mapping[str, object]:
+    return flatten_top_level_schema_combinators(drop_non_python_regex_patterns(schema))
+
+
+def tool_with_sanitized_parameters(
+    tool: Mapping[str, object],
+    sanitize: Callable[[Mapping[str, object]], Mapping[str, object]],
+) -> Mapping[str, object]:
     function: Final = tool.get("function")
     if not isinstance(function, dict):
         return tool
     parameters: Final = function.get("parameters")
     if not isinstance(parameters, dict):
         return tool
-    flattened: Final = flatten_top_level_schema_combinators(parameters)
-    if flattened is parameters:
+    sanitized: Final = sanitize(parameters)
+    if sanitized is parameters:
         return tool
-    return {**tool, "function": {**function, "parameters": flattened}}  # mutable-ok: request tools are JSON dicts
+    return {**tool, "function": {**function, "parameters": sanitized}}  # mutable-ok: request tools are JSON dicts
 
 
 def _get_image_mime_type_from_url(url: str) -> str | None:
@@ -1823,14 +1934,11 @@ def _extract_reasoning_content(message: dict) -> tuple[str | None, str | None]:
     return None, message_content
 
 
-def _readable_thinking_text(
-    block: ChatCompletionThinkingBlock | ChatCompletionRedactedThinkingBlock,
-) -> str:
+def _readable_thinking_text(block: Mapping[str, object]) -> str:
     """The text a chat model can read back, empty for redacted blocks and malformed ones."""
     if block.get("type") != "thinking":
         return ""
-    thinking: Final = cast(ChatCompletionThinkingBlock, block).get("thinking")  # cast-ok: narrowed by the type tag
-    return str(thinking or "")
+    return str(block.get("thinking") or "")
 
 
 def reasoning_content_from_thinking_blocks(
@@ -1843,24 +1951,125 @@ def reasoning_content_from_thinking_blocks(
     return "\n".join(text for block in thinking_blocks if (text := _readable_thinking_text(block)))
 
 
-def responses_reasoning_item_from_thinking_blocks(
-    thinking_blocks: Iterable[ChatCompletionThinkingBlock | ChatCompletionRedactedThinkingBlock],
-) -> ChatCompletionReasoningItem | None:
-    """Build a Responses API `reasoning` input item from Anthropic thinking blocks.
+ENCRYPTED_REASONING_SIGNATURE_PREFIX: Final = "litellm_encrypted_reasoning:"
 
-    The item carries no `id`: the Responses API rejects an empty one and 404s on any id it
-    did not mint itself, while an item without an id is always accepted.
+
+def encrypted_reasoning_signature(encrypted_content: str) -> str:
+    """The opaque value a Responses API reasoning item's `encrypted_content` travels in.
+
+    Anthropic clients echo a thinking block's `signature` and a redacted block's `data`
+    back verbatim, so either field can carry the encrypted reasoning across turns; the
+    prefix tells the two apart from a signature Anthropic minted.
     """
+    return f"{ENCRYPTED_REASONING_SIGNATURE_PREFIX}{encrypted_content}"
+
+
+def _carries_encrypted_reasoning(signature: object) -> bool:
+    return isinstance(signature, str) and signature.startswith(ENCRYPTED_REASONING_SIGNATURE_PREFIX)
+
+
+def encrypted_content_from_signature(signature: object) -> str | None:
+    if not isinstance(signature, str) or not _carries_encrypted_reasoning(signature):
+        return None
+    return signature.removeprefix(ENCRYPTED_REASONING_SIGNATURE_PREFIX) or None
+
+
+def _encrypted_reasoning_field(block: Mapping[str, object]) -> object:
+    match block.get("type"):
+        case "thinking":
+            return block.get("signature")
+        case "redacted_thinking":
+            return block.get("data")
+        case _:
+            return None
+
+
+def encrypted_content_of_block(block: Mapping[str, object]) -> str | None:
+    return encrypted_content_from_signature(_encrypted_reasoning_field(block))
+
+
+def is_encrypted_reasoning_block(block: object) -> bool:
+    """A thinking or redacted_thinking block carrying Responses API encrypted reasoning.
+
+    Only the Responses API that minted the content can read it back, so an Anthropic
+    backend has to drop such a block rather than fail signature verification on it.
+    """
+    if not isinstance(block, Mapping):
+        return False
+    mapping: Final = cast(Mapping[str, object], block)  # cast-ok: narrowed by isinstance
+    return _carries_encrypted_reasoning(_encrypted_reasoning_field(mapping))
+
+
+def strip_encrypted_reasoning_from_messages(messages: object) -> None:
+    """Drop the bridge-tagged reasoning blocks a routed deployment cannot decrypt from
+    Anthropic-shaped history.
+
+    The whole block goes, the way #40280 drops undecryptable Responses ``input`` items: a
+    provider that did not mint the block rejects it signed (a foreign signature) and unsigned
+    (a missing signature) alike, so keeping its text as an unsigned thinking block only moves
+    the 400 from the router to the provider.
+
+    Mutates the content lists in place: the router's fallback snapshot shares these
+    message objects, so a rebound list would replay the stripped blocks on the fallback hop.
+    """
+    if not isinstance(messages, list):
+        return
+    for content in _anthropic_content_lists(cast(list[object], messages)):  # cast-ok: untyped client json
+        _strip_encrypted_reasoning_from_blocks(content)
+
+
+def _anthropic_content_lists(messages: Sequence[object]) -> Iterator[object]:
+    return (
+        cast(list[object], content)  # cast-ok: narrowed by isinstance
+        for message in messages
+        if isinstance(message, Mapping)
+        for content in (cast(Mapping[str, object], message).get("content"),)  # cast-ok: narrowed by isinstance
+        if isinstance(content, list)
+    )
+
+
+def _strip_encrypted_reasoning_from_blocks(content: object) -> None:
+    blocks: Final = cast(list[object], content)  # cast-ok: narrowed by the caller's isinstance
+    kept: Final = tuple(block for block in blocks if not is_encrypted_reasoning_block(block))
+    blocks[:] = kept  # rebind-ok: shared with fallback snapshot
+
+
+def _reasoning_replay_group_key(indexed_block: tuple[int, Mapping[str, object]]) -> str:
+    index, block = indexed_block
+    return f"encrypted:{index}" if is_encrypted_reasoning_block(block) else "summary"
+
+
+def _reasoning_item_from_block_group(group: tuple[Mapping[str, object], ...]) -> ChatCompletionReasoningItem | None:
     summary: Final[list[ChatCompletionReasoningSummaryTextBlock]] = [  # mutable-ok: API message payload
         ChatCompletionReasoningSummaryTextBlock(type="summary_text", text=text)
-        for block in thinking_blocks
+        for block in group
         if (text := _readable_thinking_text(block))
     ]
+    encrypted_content: Final = encrypted_content_of_block(group[0])
+    if encrypted_content is not None:
+        return ChatCompletionReasoningItem(type="reasoning", summary=summary, encrypted_content=encrypted_content)
     if not summary:
         return None
     return ChatCompletionReasoningItem(type="reasoning", summary=summary)
 
 
+def responses_reasoning_items_from_thinking_blocks(
+    thinking_blocks: Iterable[Mapping[str, object]],
+) -> tuple[ChatCompletionReasoningItem, ...]:
+    """Build Responses API `reasoning` input items from Anthropic thinking blocks.
+
+    A block carrying encrypted reasoning replays the item it came from byte for byte;
+    a run of plain thinking blocks collapses into one summary-only item. No item carries
+    an `id`: the Responses API 404s on any id it did not mint itself and rejects an empty
+    one, while an item without an id is always accepted.
+    """
+    return tuple(
+        item
+        for _, group in groupby(enumerate(thinking_blocks), key=_reasoning_replay_group_key)
+        if (item := _reasoning_item_from_block_group(tuple(block for _, block in group))) is not None
+    )
+
+
 def _parse_content_for_reasoning(
     message_text: str | None,
 ) -> tuple[str | None, str | None]:
diff --git a/litellm/litellm_core_utils/prompt_templates/factory.py b/litellm/litellm_core_utils/prompt_templates/factory.py
index 56c1d605700..ece619e3883 100644
--- a/litellm/litellm_core_utils/prompt_templates/factory.py
+++ b/litellm/litellm_core_utils/prompt_templates/factory.py
@@ -46,6 +46,7 @@ from litellm.types.utils import GenericImageParsingChunk
 from .common_utils import (
     convert_content_list_to_str,
     infer_content_type_from_url_and_content,
+    is_encrypted_reasoning_block,
     is_non_content_values_set,
     parse_tool_call_arguments,
 )
@@ -2299,13 +2300,16 @@ def sanitize_messages_for_tool_calling(
 
 
 def _is_unsignable_thinking_block(block: object) -> bool:
-    """A `thinking` block that Anthropic cannot accept on input.
+    """A thinking block that Anthropic cannot accept on input.
 
     Anthropic verifies the thinking signature cryptographically, so a block whose
     signature is null, empty, or missing (e.g. from an open-source reasoning model)
-    is rejected with a 400 and must be dropped rather than blanked or repaired.
-    `redacted_thinking` blocks carry no signature and are always kept.
+    is rejected with a 400 and must be dropped rather than blanked or repaired, and
+    so is a block whose signature or data carries another provider's encrypted
+    reasoning. A `redacted_thinking` block Anthropic minted is always kept.
     """
+    if is_encrypted_reasoning_block(block):
+        return True
     if not isinstance(block, dict) or block.get("type") != "thinking":
         return False
     signature: Final = block.get("signature")
diff --git a/litellm/litellm_core_utils/redact_messages.py b/litellm/litellm_core_utils/redact_messages.py
index 9402d465712..9d22a5ddef5 100644
--- a/litellm/litellm_core_utils/redact_messages.py
+++ b/litellm/litellm_core_utils/redact_messages.py
@@ -16,6 +16,7 @@ from typing import TYPE_CHECKING, Any, Final
 import litellm
 from litellm.constants import REDACTED_BY_LITELLM
 from litellm.integrations.custom_logger import CustomLogger
+from litellm.litellm_core_utils.classifier_logging import without_classifier_audit
 from litellm.litellm_core_utils.core_helpers import (
     get_metadata_variable_name_from_kwargs,
 )
@@ -162,12 +163,19 @@ def _redact_responses_api_output_dict(output_items, redacted_str: str):
             output_item["arguments"] = redacted_str
 
 
-def _redact_standard_logging_object(model_call_details: dict):
-    """Redact messages and response inside standard_logging_object if present."""
-    standard_logging_object: Final = model_call_details.get("standard_logging_object")
-    if standard_logging_object is None:
-        return
+def redacted_standard_logging_payload(payload: Mapping[str, object]) -> Mapping[str, object]:
+    """
+    Return a copy of a ``StandardLoggingPayload`` with its messages and response redacted.
 
+    The success path redacts through ``perform_redaction`` before a callback ever sees the
+    payload, but the failure path does not, so a callback that batches both has to redact
+    the ones it is handed.
+    """
+    return _redact_standard_logging_object(payload)
+
+
+def _redact_standard_logging_object(payload: Mapping[str, object]) -> dict[str, object]:
+    standard_logging_object: Final = copy.deepcopy(without_classifier_audit(payload))
     redacted_str: Final = REDACTED_BY_LITELLM
 
     if standard_logging_object.get("messages") is not None:
@@ -190,6 +198,7 @@ def _redact_standard_logging_object(model_call_details: dict):
         else:
             # For other formats (empty dict, None, etc.), use simple text format
             standard_logging_object["response"] = {"text": redacted_str}
+    return standard_logging_object
 
 
 def _redact_tool_calls_dict(message: Mapping[str, object]) -> None:
@@ -241,10 +250,16 @@ def perform_redaction(model_call_details: dict, result, redact_streaming_respons
     copy via redact_streaming_responses_for_custom_logger instead.
     """
     # Redact model_call_details
+    params: Final = model_call_details.get("litellm_params")
+    request: Final = params.get("proxy_server_request") if isinstance(params, dict) else None
+    if isinstance(params, dict) and isinstance(request, Mapping):
+        model_call_details["litellm_params"] = {**params, "proxy_server_request": without_classifier_audit(request)}
     model_call_details["messages"] = [{"role": "user", "content": REDACTED_BY_LITELLM}]
     model_call_details["prompt"] = ""
     model_call_details["input"] = ""
-    _redact_standard_logging_object(model_call_details)
+    standard_logging_object: Final = model_call_details.get("standard_logging_object")
+    if isinstance(standard_logging_object, Mapping):
+        model_call_details["standard_logging_object"] = _redact_standard_logging_object(standard_logging_object)
     redact_vertex_ai_metadata_from_litellm_params(model_call_details)
 
     # Redact streaming response
diff --git a/litellm/litellm_core_utils/sensitive_data_masker.py b/litellm/litellm_core_utils/sensitive_data_masker.py
index 22dd4170963..b4c1beea33e 100644
--- a/litellm/litellm_core_utils/sensitive_data_masker.py
+++ b/litellm/litellm_core_utils/sensitive_data_masker.py
@@ -15,6 +15,7 @@ _DEFAULT_SENSITIVE_PATTERNS: Final = frozenset(
         "token",
         "auth",
         "authorization",
+        "cookie",
         "credential",
         # Plural form: Vertex uses ``vertex_credentials``; segment-exact
         # matching otherwise misses it because "credential" != "credentials".
diff --git a/litellm/litellm_core_utils/streaming_chunk_builder_utils.py b/litellm/litellm_core_utils/streaming_chunk_builder_utils.py
index 0e01577b20e..90698296142 100644
--- a/litellm/litellm_core_utils/streaming_chunk_builder_utils.py
+++ b/litellm/litellm_core_utils/streaming_chunk_builder_utils.py
@@ -1,6 +1,6 @@
 import base64
 import time
-from collections.abc import Iterator, Mapping, Sequence
+from collections.abc import Callable, Iterator, Mapping, Sequence
 from itertools import groupby
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, TypeAlias, TypedDict, Union, cast
@@ -24,6 +24,7 @@ from litellm.types.utils import (
     Choices,
     CompletionTokensDetails,
     CompletionTokensDetailsWrapper,
+    Delta,
     Function,
     FunctionCall,
     ModelResponse,
@@ -209,7 +210,7 @@ def apply_grounding_request_counts(
 
 
 class ChunkProcessor:
-    def __init__(self, chunks: list, messages: list | None = None):
+    def __init__(self, chunks: list, messages: Sequence | None = None):
         self.chunks = self._sort_chunks(chunks)
         self.messages = messages
         self.first_chunk = chunks[0]
@@ -326,6 +327,18 @@ class ChunkProcessor:
                 return chunk_id
         return ""
 
+    @staticmethod
+    def _get_role_from_chunks(chunks: Sequence["_BaseChunk"]) -> str:
+        return ChunkProcessor._role_of_choice(next((c["choices"][0] for c in chunks if c.get("choices")), None))
+
+    @staticmethod
+    def _role_of_choice(choice: object) -> str:
+        match choice:
+            case StreamingChoices(delta=Delta(role=str() as role)) | {"delta": {"role": str() as role}} if role:
+                return role
+            case _:
+                return "assistant"
+
     @staticmethod
     def _get_model_from_chunks(chunks: Sequence["_BaseChunk"], first_chunk_model: str) -> str:
         """
@@ -353,8 +366,7 @@ class ChunkProcessor:
         model: Final = ChunkProcessor._get_model_from_chunks(chunks, first_chunk_model)
         system_fingerprint: Final = chunk.get("system_fingerprint", None)
 
-        first_chunk_with_choices: Final = next((c for c in chunks if c.get("choices")), chunk)
-        role: Final = first_chunk_with_choices["choices"][0]["delta"]["role"]
+        role: Final = ChunkProcessor._get_role_from_chunks(chunks)
         finish_reason = "stop"
         for chunk in chunks:
             if "choices" in chunk and len(chunk["choices"]) > 0:
@@ -992,8 +1004,9 @@ class ChunkProcessor:
         chunks: Sequence["_UsageBearingChunk | ModelResponse"],
         model: str,
         completion_output: str,
-        messages: list | None = None,
+        messages: Sequence | None = None,
         reasoning_tokens: int | None = None,
+        count_prompt_tokens: Callable[[], int] | None = None,
     ) -> Usage:
         """
         Calculate usage for the given chunks.
@@ -1018,7 +1031,9 @@ class ChunkProcessor:
         cost: Final[float | None] = calculated_usage_per_chunk["cost"]
 
         try:
-            returned_usage.prompt_tokens = prompt_tokens or token_counter(model=model, messages=messages)
+            returned_usage.prompt_tokens = prompt_tokens or (
+                count_prompt_tokens() if count_prompt_tokens else token_counter(model=model, messages=messages)
+            )
         except Exception:  # don't allow this failing to block a complete streaming response from being returned
             print_verbose("token_counter failed, assuming prompt tokens is 0")
             returned_usage.prompt_tokens = 0
diff --git a/litellm/litellm_core_utils/streaming_handler.py b/litellm/litellm_core_utils/streaming_handler.py
index 6ae17bac6ff..6a5a8832cc6 100644
--- a/litellm/litellm_core_utils/streaming_handler.py
+++ b/litellm/litellm_core_utils/streaming_handler.py
@@ -236,9 +236,11 @@ class CustomStreamWrapper:
         stream_options=None,
         make_call: Callable | None = None,
         _response_headers: dict | httpx.Headers | None = None,
+        count_prompt_tokens: Callable[[], int] | None = None,
     ):
         self.model = model
         self.make_call = make_call
+        self.count_prompt_tokens = count_prompt_tokens
         self.custom_llm_provider = custom_llm_provider
         self.logging_obj: LiteLLMLoggingObject = logging_obj
         self.completion_stream = completion_stream
@@ -1473,17 +1475,14 @@ class CustomStreamWrapper:
                 self.received_finish_reason = response_obj["finish_reason"]
         elif self.custom_llm_provider == "cached_response":
             cached_chunk: Final = cast(ModelResponseStream, chunk)
-            chunk_finish_reason: Final = cached_chunk.choices[0].finish_reason
+            cached_choice: Final = cached_chunk.choices[0] if cached_chunk.choices else None
+            chunk_finish_reason: Final = cached_choice.finish_reason if cached_choice is not None else None
             response_obj = {
-                "text": cached_chunk.choices[0].delta.content,
+                "text": cached_choice.delta.content if cached_choice is not None else None,
                 "is_finished": chunk_finish_reason is not None,
                 "finish_reason": chunk_finish_reason,
                 "original_chunk": cached_chunk,
-                "tool_calls": (
-                    cached_chunk.choices[0].delta.tool_calls
-                    if hasattr(cached_chunk.choices[0].delta, "tool_calls")
-                    else None
-                ),
+                "tool_calls": (getattr(cached_choice.delta, "tool_calls", None) if cached_choice is not None else None),
             }
 
             completion_obj["content"] = response_obj["text"]
@@ -1644,7 +1643,7 @@ class CustomStreamWrapper:
                         except Exception:
                             model_response.choices[0].delta = Delta()
                 else:
-                    if self.stream_options is not None and self.stream_options["include_usage"] is True:
+                    if self.send_stream_usage is True:
                         model_response.choices = []
                         return model_response
                     self._record_usage_only_chunk(model_response=model_response)
@@ -1999,6 +1998,7 @@ class CustomStreamWrapper:
                         chunks=self.chunks,
                         messages=self.messages,
                         logging_obj=self.logging_obj,
+                        count_prompt_tokens=self.count_prompt_tokens,
                     )
                 except Exception as e:
                     # stream_chunk_builder can re-raise (as APIError) on large agentic
@@ -2251,6 +2251,7 @@ class CustomStreamWrapper:
                     chunks=self.chunks,
                     messages=self.messages,
                     logging_obj=self.logging_obj,
+                    count_prompt_tokens=self.count_prompt_tokens,
                 )
             except Exception as e:
                 # see sync __next__: a raise from stream_chunk_builder inside this
@@ -2374,6 +2375,7 @@ class CustomStreamWrapper:
                 chunks=self.chunks,
                 messages=self.messages if isinstance(self.messages, list) else None,
                 logging_obj=self.logging_obj,
+                count_prompt_tokens=self.count_prompt_tokens,
             )
             if partial_response is None:
                 return
diff --git a/litellm/litellm_core_utils/token_counter.py b/litellm/litellm_core_utils/token_counter.py
index 3732ffd734c..1de2533d514 100644
--- a/litellm/litellm_core_utils/token_counter.py
+++ b/litellm/litellm_core_utils/token_counter.py
@@ -3,11 +3,15 @@
 import base64
 import io
 import struct
-from collections.abc import Callable, Iterable, Mapping, Sequence
+from collections.abc import Awaitable, Callable, Iterable, Mapping, Sequence
 from typing import Final, Literal, cast
 
+import anyio
+import anyio.lowlevel
 import httpx
 import tiktoken
+from tokenizers import Tokenizer
+from typing_extensions import ParamSpec, TypeVar
 
 import litellm
 from litellm import verbose_logger
@@ -21,7 +25,10 @@ from litellm.constants import (
     MAX_TILE_HEIGHT,
     MAX_TILE_WIDTH,
     TIKTOKEN_ENCODE_CHUNK_SIZE_CHARS,
+    TOKEN_COUNTER_MAX_CONCURRENT_COUNTS,
+    TOKEN_COUNTER_MAX_EXACT_CHARS,
 )
+from litellm.litellm_core_utils.asyncify import asyncify
 from litellm.litellm_core_utils.default_encoding import encoding as default_encoding
 from litellm.litellm_core_utils.url_utils import safe_get
 from litellm.llms.custom_httpx.http_handler import _get_httpx_client
@@ -172,6 +179,13 @@ def calculate_tiles_needed(
     return total_tiles
 
 
+def high_detail_image_token_upper_bound(base_tokens: int = 85) -> int:
+    largest_tile_count: Final = calculate_tiles_needed(
+        MAX_LONG_SIDE_FOR_IMAGE_HIGH_RES, MAX_SHORT_SIDE_FOR_IMAGE_HIGH_RES
+    )
+    return base_tokens + (base_tokens * 2) * largest_tile_count
+
+
 def _unpack_ints(fmt: str, buffer: bytes) -> tuple[int, ...]:
     return struct.unpack(fmt, buffer)
 
@@ -317,6 +331,32 @@ TokenCounterFunction = Callable[[str], int]
 Type for a function that counts tokens in a string.
 """
 
+EXTRAPOLATION_SAMPLES: Final = 16
+T_ParamSpec: Final = ParamSpec("T_ParamSpec")
+T_Retval = TypeVar("T_Retval")
+_COUNT_OFFLOAD_LIMITER: Final = anyio.lowlevel.RunVar[anyio.CapacityLimiter]("litellm_count_offload_limiter")
+
+
+def _count_offload_limiter_for_this_loop() -> anyio.CapacityLimiter:
+    existing: Final = _COUNT_OFFLOAD_LIMITER.get(None)
+    if existing is not None:
+        return existing
+    created: Final = anyio.CapacityLimiter(TOKEN_COUNTER_MAX_CONCURRENT_COUNTS)
+    _COUNT_OFFLOAD_LIMITER.set(created)
+    return created
+
+
+def offload_token_count(
+    function: Callable[T_ParamSpec, T_Retval],
+) -> Callable[T_ParamSpec, Awaitable[T_Retval]]:
+    async def offloaded(
+        *args: T_ParamSpec.args,
+        **kwargs: T_ParamSpec.kwargs,  # kwargs-ok: ParamSpec keeps the wrapped function's own keyword contract
+    ) -> T_Retval:
+        return await asyncify(function, limiter=_count_offload_limiter_for_this_loop())(*args, **kwargs)
+
+    return offloaded
+
 
 def _get_tiktoken_count_function(
     encode_length: Callable[[str], int],
@@ -538,9 +578,40 @@ def _count_extra(
     return num_tokens
 
 
+def _get_extrapolating_count_function(
+    count_exactly: TokenCounterFunction,
+    max_exact_chars: int = TOKEN_COUNTER_MAX_EXACT_CHARS,
+) -> TokenCounterFunction:
+    def count_tokens(text: str) -> int:
+        if len(text) <= max_exact_chars:
+            return count_exactly(text)
+        samples: Final = _evenly_spaced_samples(text, max_exact_chars)
+        sampled_chars: Final = sum(len(sample) for sample in samples)
+        return round(sum(count_exactly(sample) for sample in samples) * len(text) / sampled_chars)
+
+    return count_tokens
+
+
+def _evenly_spaced_samples(text: str, total_chars: int) -> tuple[str, ...]:
+    sample_count: Final = min(EXTRAPOLATION_SAMPLES, total_chars)
+    sample_chars: Final = total_chars // sample_count
+    last_start: Final = len(text) - sample_chars
+    return tuple(
+        text[start : start + sample_chars]
+        for start in (last_start * index // max(sample_count - 1, 1) for index in range(sample_count))
+    )
+
+
 def _get_count_function(
     model: str | None,
     custom_tokenizer: dict | SelectTokenizerResponse | None = None,
+) -> TokenCounterFunction:
+    return _get_extrapolating_count_function(_get_exact_count_function(model, custom_tokenizer))
+
+
+def _get_exact_count_function(
+    model: str | None,
+    custom_tokenizer: dict | SelectTokenizerResponse | None = None,
 ) -> TokenCounterFunction:
     """
     Get the function to count tokens based on the model and custom tokenizer."""
@@ -549,10 +620,10 @@ def _get_count_function(
     if model is not None or custom_tokenizer is not None:
         tokenizer_json: Final = custom_tokenizer or _select_tokenizer(model)
         if tokenizer_json["type"] == "huggingface_tokenizer":
+            tokenizer: Final[Tokenizer] = tokenizer_json["tokenizer"]
 
             def count_tokens(text: str) -> int:
-                enc: Final = tokenizer_json["tokenizer"].encode(text)
-                return len(enc.ids)
+                return len(tokenizer.encode_batch_fast([text])[0])
 
             return count_tokens
         elif tokenizer_json["type"] == "openai_tokenizer":
diff --git a/litellm/llms/anthropic/chat/guardrail_translation/handler.py b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
index e486be12fe2..9d50345d70d 100644
--- a/litellm/llms/anthropic/chat/guardrail_translation/handler.py
+++ b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
@@ -13,10 +13,11 @@ Pattern Overview:
 """
 
 import json
-from collections.abc import Iterator, Mapping, Sequence
+from collections.abc import Mapping, MutableSequence, Sequence
 from copy import deepcopy
 from dataclasses import dataclass
 from itertools import chain, repeat
+from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Protocol, cast, overload, runtime_checkable
 
 from typing_extensions import ReadOnly, TypedDict, assert_never
@@ -41,6 +42,7 @@ from litellm.llms.base_llm.guardrail_translation.utils import (
     merge_guardrailed_scoped_messages,
     merge_returned_tools_into_request_tools,
     scoped_structured_message_indices,
+    stream_item_field,
     stream_item_fingerprint,
 )
 from litellm.proxy.pass_through_endpoints.llm_provider_handlers.anthropic_passthrough_logging_handler import (
@@ -153,6 +155,46 @@ class ExtractedInput:
 EMPTY_EXTRACTED_INPUT: Final = ExtractedInput(scanned=(), images=())
 
 
+@dataclass(frozen=True, slots=True)
+class _ToolCallShape:
+    name: str | None
+    arguments: str
+
+
+@dataclass(frozen=True, slots=True)
+class _SSEFieldRewrite:
+    """One field of one nested section of a buffered SSE event, rewritten."""
+
+    section: str
+    field: str
+    value: object
+
+
+class _SSEEventRewriter(Protocol):
+    def __call__(self, event: Mapping[str, object]) -> _SSEFieldRewrite | None: ...
+
+
+def _rewritten_event(event: Mapping[str, object], rewrite_event: _SSEEventRewriter) -> Mapping[str, object]:
+    rewrite: Final = rewrite_event(event)
+    section: Final = None if rewrite is None else event.get(rewrite.section)
+    if rewrite is None or not isinstance(section, Mapping):
+        return event
+    return {**event, rewrite.section: {**section, rewrite.field: rewrite.value}}  # mutable-ok: json.dumps needs a dict
+
+
+def _tool_call_shapes(tool_calls: Sequence[object]) -> tuple[_ToolCallShape, ...]:
+    """The guardrail-visible shape of each tool call, whether the guardrail handed
+    back the ``ChatCompletionMessageToolCall`` objects it was given or plain dicts."""
+    functions: Final = tuple(stream_item_field(tool_call, "function") for tool_call in tool_calls)
+    return tuple(
+        _ToolCallShape(
+            name=name if isinstance(name := stream_item_field(function, "name"), str) else None,
+            arguments=arguments if isinstance(arguments := stream_item_field(function, "arguments"), str) else "",
+        )
+        for function in functions
+    )
+
+
 class _AnthropicSSEDelta(TypedDict, total=False):
     type: ReadOnly[str]
     text: ReadOnly[str]
@@ -170,12 +212,18 @@ class AnthropicMessagesHandler(BaseTranslation):
     them through guardrail rewrites; downstream provider handling is out of scope.
     """
 
-    delivers_ended_stream_text_rewrites = True
+    delivers_ended_stream_rewrites = True
+    assembles_streamed_response = True
 
     def __init__(self):
         super().__init__()
         self.adapter = LiteLLMAnthropicMessagesAdapter()
 
+    def post_call_hook_response(self, response: object) -> object:
+        if not isinstance(response, ModelResponse):
+            return response
+        return self.adapter.translate_openai_response_to_anthropic(response)
+
     @staticmethod
     def _build_streaming_usage_response(
         responses_so_far: Sequence[object],
@@ -1050,6 +1098,7 @@ class AnthropicMessagesHandler(BaseTranslation):
                     first_choice.message.tool_calls,
                 )
                 string_so_far = first_choice.message.content
+                pre_guardrail_tool_calls: Final = _tool_call_shapes(tool_calls_list or ())
                 guardrail_inputs: Final = GenericGuardrailAPIInputs()
                 if string_so_far:
                     guardrail_inputs["texts"] = [string_so_far]
@@ -1084,6 +1133,19 @@ class AnthropicMessagesHandler(BaseTranslation):
                     and guardrailed_texts[0] != string_so_far
                 ):
                     self._write_ended_stream_text_rewrite(responses_so_far, guardrailed_texts[0])
+                if deliver_ended_stream_rewrites:
+                    returned_tool_calls: Final = _guardrailed_inputs.get("tool_calls")
+                    self._write_ended_stream_tool_call_rewrites(
+                        responses_so_far,
+                        pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+                        post_guardrail_tool_calls=_tool_call_shapes(
+                            returned_tool_calls
+                            if isinstance(returned_tool_calls, list)
+                            and len(returned_tool_calls) == len(pre_guardrail_tool_calls)
+                            else tool_calls_list or ()
+                        ),
+                        guardrail_name=guardrail_to_apply.guardrail_name or "unknown",
+                    )
             else:
                 verbose_proxy_logger.debug("Skipping output guardrail - model response has no choices")
             return responses_so_far
@@ -1206,44 +1268,124 @@ class AnthropicMessagesHandler(BaseTranslation):
 
     @staticmethod
     def _write_ended_stream_text_rewrite(
-        responses_so_far: list[Any],  # mutable-ok: rewrites the caller's buffered chunks in place
+        responses_so_far: MutableSequence[object],  # mutable-ok: rewrites the caller's buffered chunks in place
         rewritten_text: str,
     ) -> None:
         """Deliver an ended-stream guardrail text rewrite by rewriting the
         buffered chunks in place: the first ``text_delta`` carries the full
         rewritten text and every later one is blanked, leaving the surrounding
-        message and content-block framing untouched. Handles both chunk formats
-        this stream carries (parsed event dicts and raw SSE bytes)."""
+        message and content-block framing untouched."""
         replacements: Final = chain((rewritten_text,), repeat(""))
-        for idx, item in enumerate(responses_so_far):
-            if isinstance(item, dict):
-                delta = item.get("delta")
-                if item.get("type") == "content_block_delta" and isinstance(delta, dict):
-                    if delta.get("type") == "text_delta":
-                        delta["text"] = next(replacements)
-            elif isinstance(item, (bytes, bytearray)):
-                responses_so_far[idx] = (  # rebind-ok: delivers the rewrite into the caller's buffer
-                    AnthropicMessagesHandler._rewrite_sse_text_deltas(bytes(item), replacements)
-                )
+
+        def rewrite_text_delta(event: Mapping[str, object]) -> _SSEFieldRewrite | None:
+            delta: Final = event.get("delta")
+            if event.get("type") != "content_block_delta" or not isinstance(delta, Mapping):
+                return None
+            if delta.get("type") != "text_delta":
+                return None
+            return _SSEFieldRewrite("delta", "text", next(replacements))
+
+        AnthropicMessagesHandler._rewrite_ended_stream_events(responses_so_far, rewrite_text_delta)
+
+    @classmethod
+    def _write_ended_stream_tool_call_rewrites(
+        cls,
+        responses_so_far: MutableSequence[object],  # mutable-ok: rewrites the caller's buffered chunks in place
+        *,
+        pre_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+        post_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+        guardrail_name: str,
+    ) -> None:
+        """Deliver ended-stream guardrail tool-call rewrites by rewriting the
+        buffered chunks in place: the rebuilt response lists tool calls in the
+        order of the stream's ``tool_use`` blocks, so the nth rewritten call lands
+        on the nth block, its first ``input_json_delta`` carrying the full rewritten
+        arguments, every later one blanked, and ``content_block_start`` carrying the
+        rewritten name. Blocks that do not line up with the rebuilt tool calls make
+        the rewrite undeliverable, so the pipeline executor discards it and releases
+        the original chunks."""
+        if post_guardrail_tool_calls == pre_guardrail_tool_calls:
+            return
+        block_indices: Final = tuple(
+            index
+            for item in responses_so_far
+            for event in cls._iter_sse_events(item)
+            if event.get("type") == "content_block_start"
+            and isinstance(block := event.get("content_block"), Mapping)
+            and block.get("type") == "tool_use"
+            and isinstance(index := event.get("index"), int)
+        )
+        if len(block_indices) != len(post_guardrail_tool_calls):
+            from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+            raise UndeliverableStreamRewrite(guardrail_name)
+        rewrites_by_block: Final = MappingProxyType(
+            {
+                index: after
+                for index, before, after in zip(block_indices, pre_guardrail_tool_calls, post_guardrail_tool_calls)
+                if after != before
+            }
+        )
+        argument_replacements: Final = MappingProxyType(
+            {index: chain((rewrite.arguments,), repeat("")) for index, rewrite in rewrites_by_block.items()}
+        )
+
+        def rewrite_tool_use(event: Mapping[str, object]) -> _SSEFieldRewrite | None:
+            index: Final = event.get("index")
+            if not isinstance(index, int) or index not in rewrites_by_block:
+                return None
+            match event.get("type"):
+                case "content_block_start":
+                    name: Final = rewrites_by_block[index].name
+                    if name is None:
+                        return None
+                    return _SSEFieldRewrite("content_block", "name", name)
+                case "content_block_delta":
+                    delta: Final = event.get("delta")
+                    if not isinstance(delta, Mapping) or delta.get("type") != "input_json_delta":
+                        return None
+                    return _SSEFieldRewrite("delta", "partial_json", next(argument_replacements[index]))
+                case _:
+                    return None
+
+        cls._rewrite_ended_stream_events(responses_so_far, rewrite_tool_use)
 
     @staticmethod
-    def _rewrite_sse_text_deltas(sse_bytes: bytes, replacements: "Iterator[str]") -> bytes:
-        """Rewrite every ``text_delta`` data line in one SSE chunk with the next
-        replacement text, leaving all other events and framing byte-identical."""
+    def _rewrite_ended_stream_events(
+        responses_so_far: MutableSequence[object],  # mutable-ok: rewrites the caller's buffered chunks in place
+        rewrite_event: _SSEEventRewriter,
+    ) -> None:
+        """Replace every buffered event ``rewrite_event`` returns a rewrite for, in
+        both chunk formats this stream carries (parsed event dicts and raw SSE
+        bytes), leaving every other event and the framing untouched."""
+        rewritten_items: Final = tuple(
+            AnthropicMessagesHandler._rewrite_buffered_item(item, rewrite_event) for item in responses_so_far
+        )
+        responses_so_far[:] = rewritten_items  # rebind-ok: delivers the rewrites into the caller's buffer
+
+    @staticmethod
+    def _rewrite_buffered_item(item: object, rewrite_event: _SSEEventRewriter) -> object:
+        if isinstance(item, dict):
+            return _rewritten_event(_as_str_mapping(item), rewrite_event)
+        if isinstance(item, (bytes, bytearray)):
+            return AnthropicMessagesHandler._rewrite_sse_events(bytes(item), rewrite_event)
+        return item
+
+    @staticmethod
+    def _rewrite_sse_events(sse_bytes: bytes, rewrite_event: _SSEEventRewriter) -> bytes:
+        """Rewrite the data lines of one SSE chunk that ``rewrite_event`` rewrites,
+        leaving all other events and framing byte-identical."""
         try:
             decoded: Final = sse_bytes.decode("utf-8")
         except UnicodeDecodeError:
             return sse_bytes
         return "\n\n".join(
-            AnthropicMessagesHandler._rewrite_sse_block(block, replacements) for block in decoded.split("\n\n")
+            "\n".join(AnthropicMessagesHandler._rewrite_sse_line(line, rewrite_event) for line in block.split("\n"))
+            for block in decoded.split("\n\n")
         ).encode("utf-8")
 
     @staticmethod
-    def _rewrite_sse_block(block: str, replacements: "Iterator[str]") -> str:
-        return "\n".join(AnthropicMessagesHandler._rewrite_sse_line(line, replacements) for line in block.split("\n"))
-
-    @staticmethod
-    def _rewrite_sse_line(line: str, replacements: "Iterator[str]") -> str:
+    def _rewrite_sse_line(line: str, rewrite_event: _SSEEventRewriter) -> str:
         if not line.startswith("data:"):
             return line
         try:
@@ -1252,14 +1394,10 @@ class AnthropicMessagesHandler(BaseTranslation):
             )
         except json.JSONDecodeError:
             return line
-        if not isinstance(data, dict) or data.get("type") != "content_block_delta":
+        if not isinstance(data, dict):
             return line
-        delta: Final = data.get("delta")
-        if not isinstance(delta, dict) or delta.get("type") != "text_delta":
-            return line
-        return "data: " + json.dumps(
-            {**data, "delta": {**delta, "text": next(replacements)}}  # mutable-ok: json.dumps needs plain dicts
-        )
+        rewritten: Final = _rewritten_event(_as_str_mapping(data), rewrite_event)
+        return line if rewritten is data else "data: " + json.dumps(rewritten)
 
     def get_streaming_scan_key(self, responses_so_far: Sequence[object]) -> StreamingScanKey | None:
         stream_ended: Final = self._check_streaming_has_ended(responses_so_far)
diff --git a/litellm/llms/anthropic/common_utils.py b/litellm/llms/anthropic/common_utils.py
index 2b57883cc13..87c4ec8938e 100644
--- a/litellm/llms/anthropic/common_utils.py
+++ b/litellm/llms/anthropic/common_utils.py
@@ -21,6 +21,7 @@ from litellm.constants import (
 )
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     get_file_ids_from_messages,
+    is_encrypted_reasoning_block,
 )
 from litellm.litellm_core_utils.prompt_templates.factory import (
     THOUGHT_SIGNATURE_SEPARATOR,
@@ -72,8 +73,13 @@ _CLAUDE_CODE_OBJECT_MAPPING_ADAPTER: Final = TypeAdapter(dict[object, object])
 _CLAUDE_CODE_OBJECT_LIST_ADAPTER: Final = TypeAdapter(list[object])
 
 
+_CLAUDE_CODE_USER_AGENT_PREFIXES: Final = ("claude-cli/", "claude-code/")
+
+
 def is_claude_code_user_agent(user_agent: str) -> bool:
-    return user_agent.startswith("claude-cli/")
+    """Claude Code sends its API calls through the Anthropic SDK as `claude-cli/<version>` and its own
+    fetches, such as gateway model discovery, as `claude-code/<version>`"""
+    return user_agent.startswith(_CLAUDE_CODE_USER_AGENT_PREFIXES)
 
 
 def _validated_claude_code_mapping(value: object) -> dict[object, object] | None:
@@ -1201,6 +1207,32 @@ def strip_thinking_blocks_from_anthropic_messages(messages: list[Any]) -> list[A
     return out
 
 
+def _without_encrypted_reasoning_blocks(message: dict) -> dict | None:  # mutable-ok: Anthropic message payload shape
+    if not isinstance(message, Mapping):
+        return message
+    content: Final = message.get("content")
+    if not isinstance(content, list):
+        return message
+    kept: Final = [b for b in content if not is_encrypted_reasoning_block(b)]  # mutable-ok: API message payload
+    if len(kept) == len(content):
+        return message
+    if not kept:
+        return None
+    return {**message, "content": kept}  # mutable-ok: API message payload
+
+
+def strip_encrypted_reasoning_blocks_from_anthropic_messages(
+    messages: Sequence[dict],  # mutable-ok: Anthropic message payload shape
+) -> list[dict]:  # mutable-ok: AnthropicMessagesRequest.messages is typed list[dict]
+    """
+    Drop thinking / redacted_thinking blocks that carry another provider's encrypted
+    reasoning (a turn the Responses API bridge served) before the request reaches
+    Anthropic, which cannot verify them. Anthropic's own signed blocks are kept.
+    """
+    stripped: Final = (_without_encrypted_reasoning_blocks(m) for m in messages)
+    return [m for m in stripped if m is not None]  # mutable-ok: API message payload
+
+
 def strip_thinking_blocks_from_anthropic_messages_request_dict(
     data: dict[str, Any],
 ) -> None:
@@ -1629,11 +1661,16 @@ def process_anthropic_headers(headers: httpx.Headers | dict) -> dict:
 
 
 def _anthropic_model_entry(
-    model: ModelInfoResponse, created_at: str, display_names: Mapping[str, str]
+    model: ModelInfoResponse, created_at: str, display_names: Mapping[str, str], listed_ids: Mapping[str, str]
 ) -> Mapping[str, object]:
+    listed_id: Final = listed_ids.get(model["id"])
+    source: Final[Mapping[str, object]] = (
+        MappingProxyType({"source_model": model["id"]}) if listed_id is not None else MappingProxyType({})
+    )
     return {  # mutable-ok: JSON response body, serialized by the route and never mutated
         "type": "model",
-        "id": model["id"],
+        "id": listed_id or model["id"],
+        **source,
         "display_name": display_names.get(model["id"], model["id"]),
         "created_at": created_at,
         "max_input_tokens": model.get("max_input_tokens"),
@@ -1644,6 +1681,7 @@ def _anthropic_model_entry(
 def create_anthropic_model_list_response(
     models: Sequence[ModelInfoResponse],
     display_names: Mapping[str, str] = MappingProxyType({}),
+    listed_ids: Mapping[str, str] = MappingProxyType({}),
 ) -> Mapping[str, object]:
     """Build the Anthropic-native /v1/models envelope.
 
@@ -1653,17 +1691,19 @@ def create_anthropic_model_list_response(
     over from the OpenAI-shaped listing, named as the Messages API names them, and
     are always present because the vendor shape declares them nullable, not optional.
     display_names maps a listed model id to a configured human-readable name; ids
-    without an entry fall back to the id itself, matching the vendor behavior
+    without an entry fall back to the id itself, matching the vendor behavior.
+    listed_ids maps a model id to the id the caller should see it under (the Claude
+    Code view); ids without an entry are listed as they are
     """
     created_at: Final = (
         datetime.fromtimestamp(DEFAULT_MODEL_CREATED_AT_TIME, tz=timezone.utc).isoformat().replace("+00:00", "Z")
     )
     data: Final = [  # mutable-ok: JSON response body, serialized by the route and never mutated
-        _anthropic_model_entry(model, created_at, display_names) for model in models
+        _anthropic_model_entry(model, created_at, display_names, listed_ids) for model in models
     ]
     return {  # mutable-ok: JSON response body, serialized by the route and never mutated
         "data": data,
         "has_more": False,
-        "first_id": models[0]["id"] if models else None,
-        "last_id": models[-1]["id"] if models else None,
+        "first_id": data[0]["id"] if data else None,
+        "last_id": data[-1]["id"] if data else None,
     }
diff --git a/litellm/llms/anthropic/experimental_pass_through/adapters/transformation.py b/litellm/llms/anthropic/experimental_pass_through/adapters/transformation.py
index db890662132..9b3a57cc422 100644
--- a/litellm/llms/anthropic/experimental_pass_through/adapters/transformation.py
+++ b/litellm/llms/anthropic/experimental_pass_through/adapters/transformation.py
@@ -113,6 +113,7 @@ from litellm.litellm_core_utils.reasoning_effort_utils import (
 from litellm.llms.anthropic.common_utils import (
     is_empty_unsigned_thinking_block,
     normalize_anthropic_tool_use_id,
+    strip_encrypted_reasoning_blocks_from_anthropic_messages,
 )
 from litellm.llms.anthropic.experimental_pass_through.context_management import (
     PolyfillResult,
@@ -417,7 +418,8 @@ class LiteLLMAnthropicMessagesAdapter:
         model: str | None = None,
     ) -> list:
         new_messages: Final[list[AllMessageValues]] = []
-        for m in messages:
+        replayable_messages: Final = strip_encrypted_reasoning_blocks_from_anthropic_messages(messages)
+        for m in replayable_messages:
             user_message: ChatCompletionUserMessage | None = None
             tool_message_list: list[ChatCompletionToolMessage] = []
             new_user_content_list: list[ChatCompletionTextObject | ChatCompletionImageObject] = []
@@ -1487,8 +1489,9 @@ class LiteLLMAnthropicMessagesAdapter:
             anthropic_content.insert(0, polyfill_result.compaction_block)
 
         ## extract finish reason
+        openai_finish_reason: Final = response.choices[0].finish_reason if response.choices else "stop"
         translated_finish_reason: Final = self._translate_openai_finish_reason_to_anthropic(
-            openai_finish_reason=response.choices[0].finish_reason
+            openai_finish_reason=openai_finish_reason
         )
         anthropic_finish_reason: Final = (
             "refusal"
diff --git a/litellm/llms/anthropic/experimental_pass_through/messages/transformation.py b/litellm/llms/anthropic/experimental_pass_through/messages/transformation.py
index 8267da157ad..9f9346fad4d 100644
--- a/litellm/llms/anthropic/experimental_pass_through/messages/transformation.py
+++ b/litellm/llms/anthropic/experimental_pass_through/messages/transformation.py
@@ -25,6 +25,7 @@ from ...common_utils import (
     AnthropicModelInfo,
     optionally_handle_anthropic_oauth,
     strip_advisor_blocks_from_messages,
+    strip_encrypted_reasoning_blocks_from_anthropic_messages,
 )
 
 DEFAULT_ANTHROPIC_API_VERSION: Final = "2023-06-01"
@@ -613,7 +614,7 @@ class AnthropicMessagesConfig(BaseAnthropicMessagesConfig):
             messages = strip_advisor_blocks_from_messages(messages)
 
         anthropic_messages_request: Final[AnthropicMessagesRequest] = AnthropicMessagesRequest(
-            messages=messages,
+            messages=strip_encrypted_reasoning_blocks_from_anthropic_messages(messages),
             max_tokens=max_tokens,
             model=model,
             **anthropic_messages_optional_request_params,
diff --git a/litellm/llms/anthropic/experimental_pass_through/responses_adapters/handler.py b/litellm/llms/anthropic/experimental_pass_through/responses_adapters/handler.py
index 0445c23ed8c..7731c883d9f 100644
--- a/litellm/llms/anthropic/experimental_pass_through/responses_adapters/handler.py
+++ b/litellm/llms/anthropic/experimental_pass_through/responses_adapters/handler.py
@@ -19,6 +19,7 @@ from litellm.types.llms.anthropic_messages.anthropic_response import (
     AnthropicMessagesResponse,
 )
 from litellm.types.llms.openai import ResponsesAPIResponse
+from litellm.utils import ProviderConfigManager
 
 from ..utils import litellm_logging_obj_from_kwargs, local_model_name
 from .streaming_iterator import AnthropicResponsesStreamWrapper
@@ -34,6 +35,15 @@ def _forwarded_kwargs(extra_kwargs: Mapping[str, object] | None) -> Mapping[str,
     return extra_kwargs or {}
 
 
+def _provider_returns_encrypted_reasoning(model: str, custom_llm_provider: object) -> bool:
+    provider: Final = (
+        custom_llm_provider if isinstance(custom_llm_provider, str) else litellm.get_llm_provider(model=model)[1]
+    )
+    provider_model: Final = local_model_name(model, provider)
+    responses_config: Final = ProviderConfigManager.get_provider_responses_api_config(provider, provider_model)
+    return responses_config is not None and "include" in responses_config.get_supported_openai_params(provider_model)
+
+
 def _build_responses_kwargs(
     *,
     max_tokens: int,
@@ -85,8 +95,13 @@ def _build_responses_kwargs(
         request_data["output_format"] = output_format
 
     anthropic_request: Final = AnthropicMessagesRequest(**request_data)
-    responses_kwargs: Final = _ADAPTER.translate_request(anthropic_request)
     forwarded_kwargs: Final = _forwarded_kwargs(extra_kwargs)
+    responses_kwargs: Final = _ADAPTER.translate_request(
+        anthropic_request,
+        include_encrypted_reasoning=_provider_returns_encrypted_reasoning(
+            model, forwarded_kwargs.get("custom_llm_provider")
+        ),
+    )
 
     # Normalize reasoning effort based on model capabilities
     # (e.g. "max" → "xhigh"/"high", "minimal" → "low" if unsupported)
@@ -111,7 +126,7 @@ def _build_responses_kwargs(
         responses_kwargs["stream"] = True
 
     # Forward litellm-specific kwargs (api_key, api_base, logging obj, etc.)
-    excluded: Final = {"anthropic_messages"}
+    excluded: Final = frozenset(("anthropic_messages",))
     for key, value in forwarded_kwargs.items():
         if key == "litellm_logging_obj" and value is not None:
             from litellm.litellm_core_utils.litellm_logging import (
@@ -132,6 +147,14 @@ def _build_responses_kwargs(
     if explicit_prompt_cache_key is not None:
         responses_kwargs["prompt_cache_key"] = explicit_prompt_cache_key
 
+    deployment_include: Final = forwarded_kwargs.get("include")
+    bridge_include: Final = responses_kwargs.get("include")
+    if isinstance(deployment_include, list) and isinstance(bridge_include, list):
+        responses_kwargs["include"] = [
+            *bridge_include,
+            *(item for item in deployment_include if item not in bridge_include),
+        ]
+
     return responses_kwargs
 
 
diff --git a/litellm/llms/anthropic/experimental_pass_through/responses_adapters/streaming_iterator.py b/litellm/llms/anthropic/experimental_pass_through/responses_adapters/streaming_iterator.py
index 2e0a6a9df8f..f753e87fee3 100644
--- a/litellm/llms/anthropic/experimental_pass_through/responses_adapters/streaming_iterator.py
+++ b/litellm/llms/anthropic/experimental_pass_through/responses_adapters/streaming_iterator.py
@@ -9,13 +9,19 @@ from typing import TYPE_CHECKING, Any, Final
 
 from litellm import verbose_logger
 from litellm._uuid import uuid
+from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    encrypted_reasoning_signature,
+)
 from litellm.llms.anthropic.experimental_pass_through.messages.utils import (
     refusal_stop_details,
     responses_output_refusal_text,
 )
 from litellm.types.llms.anthropic_messages.anthropic_response import AnthropicUsage
 
-from .transformation import LiteLLMAnthropicToResponsesAPIAdapter
+from .transformation import (
+    REASONING_SUMMARY_PART_SEPARATOR,
+    LiteLLMAnthropicToResponsesAPIAdapter,
+)
 
 if TYPE_CHECKING:
     from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObject
@@ -29,9 +35,10 @@ class AnthropicResponsesStreamWrapper:
       response.created                   -> message_start
       response.output_item.added         -> content_block_start (if message/function_call)
       response.output_text.delta         -> content_block_delta (text_delta)
+      response.reasoning_summary_part.added -> content_block_delta (thinking_delta separator)
       response.reasoning_summary_text.delta -> content_block_delta (thinking_delta)
       response.function_call_arguments.delta -> content_block_delta (input_json_delta)
-      response.output_item.done          -> content_block_stop
+      response.output_item.done          -> content_block_delta (signature_delta) + content_block_stop
       response.completed                 -> message_delta + message_stop
     """
 
@@ -94,6 +101,38 @@ class AnthropicResponsesStreamWrapper:
         )
         return block_idx
 
+    @staticmethod
+    def _field(source: object, name: str) -> object:
+        return source.get(name) if isinstance(source, dict) else getattr(source, name, None)
+
+    def _close_reasoning_item(self, item: object, item_id: str | None) -> None:
+        block_idx: Final = self._item_id_to_block_index.get(item_id, -1) if item_id else self._current_block_index
+        encrypted_content: Final = self._field(item, "encrypted_content")
+        signature: Final = (
+            encrypted_reasoning_signature(encrypted_content)
+            if isinstance(encrypted_content, str) and encrypted_content
+            else None
+        )
+        if block_idx < 0 and signature is None:
+            return
+        if block_idx < 0:
+            redacted_idx: Final = self._open_block(
+                item_id,
+                {"type": "redacted_thinking", "data": signature},  # mutable-ok: API message payload
+            )
+            stop: Final = {"type": "content_block_stop", "index": redacted_idx}  # mutable-ok: API message payload
+            self._chunk_queue.append(stop)
+            return
+        if signature is not None:
+            self._chunk_queue.append(
+                {  # mutable-ok: API message payload
+                    "type": "content_block_delta",
+                    "index": block_idx,
+                    "delta": {"type": "signature_delta", "signature": signature},  # mutable-ok: API message payload
+                }
+            )
+        self._chunk_queue.append({"type": "content_block_stop", "index": block_idx})  # mutable-ok: API message payload
+
     def _process_event(self, event: object) -> None:
         """Convert one Responses API event into zero or more Anthropic chunks queued for emission."""
         event_type = getattr(event, "type", None)
@@ -175,6 +214,26 @@ class AnthropicResponsesStreamWrapper:
             )
             return
 
+        if event_type == "response.reasoning_summary_part.added":
+            part_item_id: Final = self._field(event, "item_id")
+            summary_index: Final = self._field(event, "summary_index")
+            part_block_idx: Final = (
+                self._item_id_to_block_index.get(part_item_id, -1) if isinstance(part_item_id, str) else -1
+            )
+            if part_block_idx < 0 or not isinstance(summary_index, int) or summary_index == 0:
+                return
+            self._chunk_queue.append(
+                {  # mutable-ok: API message payload
+                    "type": "content_block_delta",
+                    "index": part_block_idx,
+                    "delta": {  # mutable-ok: API message payload
+                        "type": "thinking_delta",
+                        "thinking": REASONING_SUMMARY_PART_SEPARATOR,
+                    },
+                }
+            )
+            return
+
         # ---- reasoning summary text delta ----
         if event_type == "response.reasoning_summary_text.delta":
             item_id = getattr(event, "item_id", None) or (event.get("item_id") if isinstance(event, dict) else None)
@@ -220,6 +279,9 @@ class AnthropicResponsesStreamWrapper:
             item_id = (
                 getattr(item, "id", None) or (item.get("id") if isinstance(item, dict) else None) if item else None
             )
+            if self._field(item, "type") == "reasoning":
+                self._close_reasoning_item(item, item_id)
+                return
             block_idx = self._item_id_to_block_index.get(item_id, -1) if item_id else self._current_block_index
             if block_idx < 0:
                 return
diff --git a/litellm/llms/anthropic/experimental_pass_through/responses_adapters/transformation.py b/litellm/llms/anthropic/experimental_pass_through/responses_adapters/transformation.py
index f1daf2be42a..1fdb0318bab 100644
--- a/litellm/llms/anthropic/experimental_pass_through/responses_adapters/transformation.py
+++ b/litellm/llms/anthropic/experimental_pass_through/responses_adapters/transformation.py
@@ -13,7 +13,8 @@ from typing import Any, Final, cast
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     TOOL_RESULT_IMAGE_BOUNDARY,
     TOOL_RESULT_IMAGE_PLACEHOLDER,
-    responses_reasoning_item_from_thinking_blocks,
+    encrypted_reasoning_signature,
+    responses_reasoning_items_from_thinking_blocks,
     with_prompt_cache_breakpoint,
 )
 from litellm.litellm_core_utils.reasoning_effort_utils import (
@@ -33,6 +34,7 @@ from litellm.types.llms.anthropic import (
     AnthropicFinishReason,
     AnthropicMessagesRequest,
     AnthropicMessagesToolChoice,
+    AnthropicResponseContentBlockRedactedThinking,
     AnthropicResponseContentBlockText,
     AnthropicResponseContentBlockThinking,
     AnthropicResponseContentBlockToolUse,
@@ -43,11 +45,13 @@ from litellm.types.llms.anthropic_messages.anthropic_response import (
     AnthropicUsage,
 )
 from litellm.types.llms.openai import (
-    ChatCompletionThinkingBlock,
     ResponseAPIUsage,
     ResponsesAPIResponse,
 )
 
+REASONING_SUMMARY_PART_SEPARATOR: Final = "\n\n"
+RESPONSES_INCLUDE_ENCRYPTED_REASONING: Final = "reasoning.encrypted_content"
+
 
 class LiteLLMAnthropicToResponsesAPIAdapter:
     """
@@ -163,49 +167,55 @@ class LiteLLMAnthropicToResponsesAPIAdapter:
         return str(getattr(part, "text", None) or "")
 
     @classmethod
-    def _thinking_blocks_from_reasoning_item(
+    def _thinking_block_from_reasoning_item(
         cls,
         summary: Iterable[object],
-    ) -> tuple[dict[str, Any], ...]:  # mutable-ok: API message payload
-        """Anthropic thinking blocks for one Responses reasoning item.
+        encrypted_content: object,
+    ) -> dict[str, Any] | None:  # mutable-ok: API message payload
+        """The one Anthropic block for a Responses reasoning item.
 
-        The signature stays empty: only Anthropic can sign a thinking block, and a stand-in
-        value would be replayed as a real one and rejected by every backend that verifies it.
+        The item's encrypted reasoning rides the block's opaque field (`signature`, or
+        `data` when there is no summary text) so the client echoes it back and the next
+        turn replays the very item OpenAI produced; without it the signature stays empty,
+        since only Anthropic can sign a thinking block.
         """
-        return tuple(
-            AnthropicResponseContentBlockThinking(
-                type="thinking",
-                thinking=text,
-                signature=None,
-            ).model_dump()
-            for part in summary
-            if (text := cls._summary_part_text(part))
+        text: Final = REASONING_SUMMARY_PART_SEPARATOR.join(
+            part_text for part in summary if (part_text := cls._summary_part_text(part))
         )
+        if not isinstance(encrypted_content, str) or not encrypted_content:
+            if not text:
+                return None
+            return AnthropicResponseContentBlockThinking(type="thinking", thinking=text, signature=None).model_dump()
+        signature: Final = encrypted_reasoning_signature(encrypted_content)
+        if not text:
+            return AnthropicResponseContentBlockRedactedThinking(type="redacted_thinking", data=signature).model_dump()
+        return AnthropicResponseContentBlockThinking(type="thinking", thinking=text, signature=signature).model_dump()
 
     @staticmethod
     def _assistant_block_group_key(indexed_block: tuple[int, Mapping[str, object]]) -> str:
         """Group a run of consecutive thinking blocks together; keep every other block alone."""
         index, block = indexed_block
-        return "thinking" if block.get("type") == "thinking" else f"block:{index}"
+        return "thinking" if block.get("type") in ("thinking", "redacted_thinking") else f"block:{index}"
 
     @classmethod
-    def _assistant_group_to_input_item(
+    def _assistant_group_to_input_items(
         cls, group: tuple[Mapping[str, object], ...]
-    ) -> dict[str, Any] | None:  # mutable-ok: API message payload
+    ) -> tuple[dict[str, Any], ...]:  # mutable-ok: API message payload
         first: Final = group[0]
         btype: Final = first.get("type")
-        if btype == "thinking":
-            blocks: Final = cast(tuple[ChatCompletionThinkingBlock, ...], group)  # cast-ok: untrusted client payload
-            reasoning_item: Final = responses_reasoning_item_from_thinking_blocks(blocks)
-            return None if reasoning_item is None else dict(reasoning_item)  # mutable-ok: API message payload
+        if btype in ("thinking", "redacted_thinking"):
+            replayed: Final = responses_reasoning_items_from_thinking_blocks(group)
+            return tuple(dict(item) for item in replayed)  # mutable-ok: API message payload
         if btype == "tool_use":
-            return {  # mutable-ok: API message payload
-                "type": "function_call",
-                "call_id": first.get("id", ""),
-                "name": first.get("name", ""),
-                "arguments": json.dumps(first.get("input", {})),  # mutable-ok: API message payload
-            }
-        return None
+            return (
+                {  # mutable-ok: API message payload
+                    "type": "function_call",
+                    "call_id": first.get("id", ""),
+                    "name": first.get("name", ""),
+                    "arguments": json.dumps(first.get("input", {})),  # mutable-ok: API message payload
+                },
+            )
+        return ()
 
     def translate_messages_to_responses_input(
         self,
@@ -362,7 +372,7 @@ class LiteLLMAnthropicToResponsesAPIAdapter:
                     input_items.extend(
                         item
                         for _, group in groupby(enumerate(blocks), key=self._assistant_block_group_key)
-                        if (item := self._assistant_group_to_input_item(tuple(block for _, block in group))) is not None
+                        for item in self._assistant_group_to_input_items(tuple(block for _, block in group))
                     )
                     asst_parts: list[dict[str, Any]] = [  # mutable-ok: API message payload
                         {"type": "output_text", "text": block.get("text", "")}  # mutable-ok: API message payload
@@ -495,10 +505,16 @@ class LiteLLMAnthropicToResponsesAPIAdapter:
     def translate_request(
         self,
         anthropic_request: AnthropicMessagesRequest,
+        include_encrypted_reasoning: bool = True,
     ) -> dict[str, Any]:
         """
         Translate a full Anthropic /v1/messages request dict to
         litellm.responses() / litellm.aresponses() kwargs.
+
+        ``include_encrypted_reasoning`` asks the provider for ``reasoning.encrypted_content``
+        on every call, so a reasoning model's items can be replayed intact next turn even
+        when the client sent no ``thinking`` block; pass False for a provider whose
+        Responses API rejects ``include``.
         """
         model: Final[str] = anthropic_request["model"]
         messages_list: Final = cast(
@@ -528,6 +544,8 @@ class LiteLLMAnthropicToResponsesAPIAdapter:
             "model": model,
             "input": input_items,
         }
+        if include_encrypted_reasoning:
+            responses_kwargs["include"] = [RESPONSES_INCLUDE_ENCRYPTED_REASONING]  # mutable-ok: API request payload
 
         if system and not developer_parts:
             if isinstance(system, str):
@@ -634,7 +652,9 @@ class LiteLLMAnthropicToResponsesAPIAdapter:
 
         for item in response.output:
             if isinstance(item, ResponseReasoningItem):
-                content.extend(self._thinking_blocks_from_reasoning_item(item.summary))
+                reasoning_block = self._thinking_block_from_reasoning_item(item.summary, item.encrypted_content)
+                if reasoning_block is not None:
+                    content.append(reasoning_block)
 
             elif isinstance(item, ResponseOutputMessage):
                 for part in item.content:
@@ -684,11 +704,12 @@ class LiteLLMAnthropicToResponsesAPIAdapter:
                                     ).model_dump()
                                 )
                 elif item_type == "reasoning":
-                    content.extend(
-                        self._thinking_blocks_from_reasoning_item(
-                            cast(Iterable[object], item.get("summary") or ()),  # cast-ok: untyped provider json
-                        )
+                    reasoning_block = self._thinking_block_from_reasoning_item(
+                        cast(Iterable[object], item.get("summary") or ()),  # cast-ok: untyped provider json
+                        item.get("encrypted_content"),
                     )
+                    if reasoning_block is not None:
+                        content.append(reasoning_block)
                 elif item_type == "function_call":
                     try:
                         input_data = json.loads(item.get("arguments", "{}"))
diff --git a/litellm/llms/azure/audio_transcriptions.py b/litellm/llms/azure/audio_transcriptions.py
index 4a5ed2ccb0c..564ec94ba6b 100644
--- a/litellm/llms/azure/audio_transcriptions.py
+++ b/litellm/llms/azure/audio_transcriptions.py
@@ -37,6 +37,7 @@ class AzureAudioTranscription(AzureChatCompletion):
         azure_ad_token: str | None = None,
         atranscription: bool = False,
         litellm_params: dict | None = None,
+        custom_llm_provider: str = "azure",
     ) -> TranscriptionResponse | Coroutine[Any, Any, TranscriptionResponse]:
         data: Final = {"model": model, "file": audio_file, **optional_params}
 
@@ -53,6 +54,7 @@ class AzureAudioTranscription(AzureChatCompletion):
                 logging_obj=logging_obj,
                 model=model,
                 litellm_params=litellm_params,
+                custom_llm_provider=custom_llm_provider,
             )
 
         azure_client: Final = self.get_azure_openai_client(
@@ -99,7 +101,7 @@ class AzureAudioTranscription(AzureChatCompletion):
             additional_args={"complete_input_dict": data},
             original_response=stringified_response,
         )
-        hidden_params: Final = {"model": model, "custom_llm_provider": "azure"}
+        hidden_params: Final = {"model": model, "custom_llm_provider": custom_llm_provider}
         final_response: Final[TranscriptionResponse] = convert_to_model_response_object(
             response_object=stringified_response,
             model_response_object=model_response,
@@ -122,6 +124,7 @@ class AzureAudioTranscription(AzureChatCompletion):
         client=None,
         max_retries=None,
         litellm_params: dict | None = None,
+        custom_llm_provider: str = "azure",
     ) -> TranscriptionResponse:
         response = None
         try:
@@ -178,7 +181,7 @@ class AzureAudioTranscription(AzureChatCompletion):
                 },
                 original_response=stringified_response,
             )
-            hidden_params: Final = {"model": model, "custom_llm_provider": "azure"}
+            hidden_params: Final = {"model": model, "custom_llm_provider": custom_llm_provider}
             response = convert_to_model_response_object(
                 _response_headers=headers,
                 response_object=stringified_response,
diff --git a/litellm/llms/azure/azure.py b/litellm/llms/azure/azure.py
index 46a9dd1a531..587165e6991 100644
--- a/litellm/llms/azure/azure.py
+++ b/litellm/llms/azure/azure.py
@@ -323,6 +323,7 @@ class AzureChatCompletion(BaseAzureLLM, BaseLLM):
                         "api_version": api_version,
                         "api_base": api_base,
                         "complete_input_dict": data,
+                        "openai_sdk": True,
                     },
                 )
                 if not isinstance(max_retries, int):
@@ -429,6 +430,7 @@ class AzureChatCompletion(BaseAzureLLM, BaseLLM):
                     "api_base": api_base,
                     "acompletion": True,
                     "complete_input_dict": data,
+                    "openai_sdk": True,
                 },
             )
 
diff --git a/litellm/llms/azure/chat/gpt_transformation.py b/litellm/llms/azure/chat/gpt_transformation.py
index 880a51eb584..ed16d7f3de0 100644
--- a/litellm/llms/azure/chat/gpt_transformation.py
+++ b/litellm/llms/azure/chat/gpt_transformation.py
@@ -7,8 +7,9 @@ from httpx._models import Headers, Response
 import litellm
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     drop_tool_reference_parts_from_tool_messages,
+    flatten_combinators_and_drop_non_python_regex_patterns,
     hoist_images_from_tool_messages,
-    tool_with_flattened_parameters,
+    tool_with_sanitized_parameters,
 )
 from litellm.litellm_core_utils.prompt_templates.factory import (
     convert_to_azure_openai_messages,
@@ -39,14 +40,17 @@ else:
 _NO_TOOLS_UPDATE: Final[Mapping[str, object]] = MappingProxyType({})
 
 
-def flattened_tools_update(optional_params: Mapping[str, object]) -> Mapping[str, object]:
+def sanitized_tools_update(optional_params: Mapping[str, object]) -> Mapping[str, object]:
     tools: Final = optional_params.get("tools")
     if not isinstance(tools, list):
         return _NO_TOOLS_UPDATE
-    flattened: Final = [  # mutable-ok: request tools are a JSON list
-        tool_with_flattened_parameters(tool) if isinstance(tool, dict) else tool for tool in tools
+    sanitized: Final = [  # mutable-ok: request tools are a JSON list
+        tool_with_sanitized_parameters(tool, flatten_combinators_and_drop_non_python_regex_patterns)
+        if isinstance(tool, dict)
+        else tool
+        for tool in tools
     ]
-    return MappingProxyType({"tools": flattened})
+    return MappingProxyType({"tools": sanitized})
 
 
 class AzureOpenAIConfig(BaseConfig):
@@ -278,7 +282,7 @@ class AzureOpenAIConfig(BaseConfig):
             "model": model,
             "messages": azure_messages,
             **optional_params,
-            **flattened_tools_update(optional_params),
+            **sanitized_tools_update(optional_params),
         }
 
     def transform_response(
diff --git a/litellm/llms/azure/chat/o_series_transformation.py b/litellm/llms/azure/chat/o_series_transformation.py
index 246bf69cb5f..09d8075e857 100644
--- a/litellm/llms/azure/chat/o_series_transformation.py
+++ b/litellm/llms/azure/chat/o_series_transformation.py
@@ -20,7 +20,7 @@ from litellm.types.llms.openai import AllMessageValues
 from litellm.utils import get_model_info, supports_reasoning
 
 from ...openai.chat.o_series_transformation import OpenAIOSeriesConfig
-from .gpt_transformation import flattened_tools_update
+from .gpt_transformation import sanitized_tools_update
 
 
 class AzureOpenAIO1Config(OpenAIOSeriesConfig):
@@ -111,6 +111,6 @@ class AzureOpenAIO1Config(OpenAIOSeriesConfig):
         model = model.replace("o_series/", "")  # handle o_series/my-random-deployment-name
         flattened_params: Final = {  # mutable-ok: transform_request's contract takes a plain JSON params dict
             **optional_params,
-            **flattened_tools_update(optional_params),
+            **sanitized_tools_update(optional_params),
         }
         return super().transform_request(model, messages, flattened_params, litellm_params, headers)
diff --git a/litellm/llms/azure/common_utils.py b/litellm/llms/azure/common_utils.py
index 6cb7d09cec4..e6b3eb1f2bb 100644
--- a/litellm/llms/azure/common_utils.py
+++ b/litellm/llms/azure/common_utils.py
@@ -14,6 +14,7 @@ from typing_extensions import ReadOnly, TypedDict
 import litellm
 from litellm._logging import verbose_logger
 from litellm.caching.caching import DualCache
+from litellm.constants import DEFAULT_MAX_RETRIES
 from litellm.llms.base_llm.chat.transformation import BaseLLMException
 from litellm.llms.openai.common_utils import BaseOpenAILLM
 from litellm.secret_managers.get_azure_ad_token_provider import (
@@ -582,7 +583,8 @@ class BaseAzureLLM(BaseOpenAILLM):
         if scope is None:
             scope = "https://cognitiveservices.azure.com/.default"
 
-        max_retries: Final = litellm_params.get("max_retries")
+        configured_max_retries: Final = litellm_params.get("max_retries")
+        max_retries: Final = DEFAULT_MAX_RETRIES if configured_max_retries is None else configured_max_retries
         timeout: Final = litellm_params.get("timeout")
         if not api_key and azure_ad_token_provider is None and tenant_id and client_id and client_secret:
             verbose_logger.debug("Using Azure AD Token Provider from Entra ID for Azure Auth")
@@ -642,8 +644,7 @@ class BaseAzureLLM(BaseOpenAILLM):
         else:
             azure_client_params["http_client"] = self._get_sync_http_client()
 
-        if max_retries is not None:
-            azure_client_params["max_retries"] = max_retries
+        azure_client_params["max_retries"] = max_retries
         if timeout is not None:
             azure_client_params["timeout"] = timeout
 
diff --git a/litellm/llms/azure/passthrough/transformation.py b/litellm/llms/azure/passthrough/transformation.py
index 898852e645f..1b5a4083ebe 100644
--- a/litellm/llms/azure/passthrough/transformation.py
+++ b/litellm/llms/azure/passthrough/transformation.py
@@ -1,24 +1,102 @@
+import re
+from collections.abc import Callable, Collection, Mapping, Sequence
+from types import MappingProxyType
 from typing import TYPE_CHECKING, Final, Optional
 
 import httpx
 from httpx import Response
+from pydantic import BaseModel, ValidationError
 
 from litellm.litellm_core_utils.litellm_logging import Logging
 from litellm.llms.azure.common_utils import BaseAzureLLM
-from litellm.llms.base_llm.passthrough.transformation import BasePassthroughConfig
+from litellm.llms.base_llm.passthrough.transformation import (
+    BasePassthroughConfig,
+    RelayShape,
+    logged_relay_shape,
+    replace_path_segment,
+    strip_leading_model_segment,
+)
 from litellm.secret_managers.main import get_secret_str
-from litellm.types.llms.openai import AllMessageValues
+from litellm.types.llms.openai import AllMessageValues, ResponsesAPIResponse, ResponsesTerminalEvent
 from litellm.types.router import GenericLiteLLMParams
+from litellm.types.utils import CallTypes, EmbeddingResponse, ImageResponse
 
 if TYPE_CHECKING:
     from httpx import URL
 
-    from litellm.types.utils import CostResponseTypes
+    from litellm.llms.base_llm.passthrough.transformation import LoggedRelayResponse
+
+
+class RelayedChatRequest(BaseModel):
+    messages: Sequence[Mapping[str, object]] | None = None
+
+
+class RelayedCallDetails(BaseModel):
+    request_data: RelayedChatRequest | None = None
+
+
+def _relayed_messages(litellm_logging_obj: Logging) -> Sequence[Mapping[str, object]] | None:
+    try:
+        details: Final = RelayedCallDetails.model_validate(litellm_logging_obj.model_call_details)
+    except ValidationError:
+        return None
+    return details.request_data.messages if details.request_data else None
+
+
+RESPONSES_RELAY_SHAPE: Final = RelayShape("/responses", CallTypes.aresponses, ResponsesAPIResponse.model_validate)
+
+OPENAI_RELAY_SHAPES: Final = (
+    RelayShape("/embeddings", CallTypes.aembedding, EmbeddingResponse.model_validate),
+    RESPONSES_RELAY_SHAPE,
+    RelayShape("/images/generations", CallTypes.aimage_generation, ImageResponse.model_validate),
+)
+
+
+def logged_responses_stream(all_chunks: Sequence[str], logging_obj: Logging) -> ResponsesTerminalEvent | None:
+    """A streaming logging object assembles the logged response from the terminal event, not from its body."""
+    from litellm.llms.openai.responses.transformation import OpenAIResponsesAPIConfig
+
+    terminal_event: Final = OpenAIResponsesAPIConfig.parse_terminal_event_from_stream_chunks(all_chunks=all_chunks)
+    if terminal_event is None:
+        return None
+    logging_obj.call_type = (
+        RESPONSES_RELAY_SHAPE.call_type.value
+    )  # rebind-ok: routes cost calculation to the relayed shape's pricing path
+    return terminal_event
+
+
+AZURE_DEPLOYMENT_SEGMENT: Final = re.compile(r"(?<![^/])openai/deployments/([^/]+)")
+
+
+def azure_router_model_in_endpoint(endpoint: str, router_models: Collection[str]) -> str | None:
+    parts: Final = endpoint.split("/")
+    if len(parts) < 2:
+        return None
+    return next((part for part in parts if part in router_models), None)
+
+
+def foreign_azure_deployment(
+    endpoint: str, model_group: str, served_models: Callable[[], Collection[str]]
+) -> str | None:
+    match: Final = AZURE_DEPLOYMENT_SEGMENT.search(endpoint)
+    if match is None:
+        return None
+    deployment: Final = match.group(1)
+    if deployment == model_group:
+        return None
+    served: Final = frozenset(name.casefold() for name in served_models())
+    return None if deployment.casefold() in served else deployment
+
+
+def without_api_version(api_base: str) -> str:
+    url: Final = httpx.URL(api_base)
+    kept_params: Final = tuple((key, value) for key, value in url.params.multi_items() if key != "api-version")
+    return str(url.copy_with(params=httpx.QueryParams(kept_params)))
 
 
 class AzurePassthroughConfig(BasePassthroughConfig):
     def is_streaming_request(self, endpoint: str, request_data: dict) -> bool:
-        return "stream" in request_data
+        return bool(request_data.get("stream"))
 
     def get_complete_url(
         self,
@@ -36,14 +114,17 @@ class AzurePassthroughConfig(BasePassthroughConfig):
 
         litellm_metadata: Final = litellm_params.get("litellm_metadata") or {}
         model_group: Final = litellm_metadata.get("model_group")
-        if model_group and model_group in endpoint:
-            endpoint = endpoint.replace(model_group, model)
+        routed_endpoint: Final = replace_path_segment(endpoint, model_group, model) if model_group else endpoint
+        native_endpoint: Final = strip_leading_model_segment(routed_endpoint, (model,))
 
+        caller_api_version: Final = request_query_params.get("api-version") if request_query_params else None
+        relay_base: Final = without_api_version(base_target_url) if caller_api_version else base_target_url
         complete_url: Final = BaseAzureLLM._get_base_azure_url(
-            api_base=base_target_url,
-            litellm_params=litellm_params,
-            route=endpoint,
-            default_api_version=litellm_params.get("api_version"),
+            api_base=relay_base,
+            litellm_params=MappingProxyType(
+                {**litellm_params, "api_version": caller_api_version or litellm_params.get("api_version")}
+            ),
+            route=native_endpoint,
         )
         return (
             httpx.URL(complete_url),
@@ -92,13 +173,13 @@ class AzurePassthroughConfig(BasePassthroughConfig):
         request_data: dict,
         logging_obj: Logging,
         endpoint: str,
-    ) -> Optional["CostResponseTypes"]:
+    ) -> Optional["LoggedRelayResponse"]:
         from litellm import encoding
         from litellm.llms.openai.chat.gpt_transformation import OpenAIGPTConfig
         from litellm.types.utils import ModelResponse
 
         if "chat/completions" not in endpoint:
-            return None
+            return logged_relay_shape(OPENAI_RELAY_SHAPES, httpx_response, logging_obj, endpoint)
 
         openai_chat_config: Final = OpenAIGPTConfig()
 
@@ -116,3 +197,27 @@ class AzurePassthroughConfig(BasePassthroughConfig):
         )
 
         return litellm_model_response
+
+    def handle_logging_collected_chunks(
+        self,
+        all_chunks: Sequence[str],
+        litellm_logging_obj: Logging,
+        model: str,
+        custom_llm_provider: str,
+        endpoint: str,
+    ) -> Optional["LoggedRelayResponse"]:
+        from litellm.proxy.pass_through_endpoints.llm_provider_handlers.openai_passthrough_logging_handler import (
+            OpenAIPassthroughLoggingHandler,
+        )
+
+        if f"/{endpoint.strip('/')}".endswith(RESPONSES_RELAY_SHAPE.path_suffix):
+            return logged_responses_stream(all_chunks, litellm_logging_obj)
+        if "chat/completions" not in endpoint:
+            return None
+
+        return OpenAIPassthroughLoggingHandler()._build_complete_streaming_response(  # pyright: ignore[reportPrivateUsage]  # the only OpenAI SSE-to-ModelResponse assembler; reimplementing it would fork the parser
+            all_chunks=all_chunks,
+            litellm_logging_obj=litellm_logging_obj,
+            model=model,
+            messages=_relayed_messages(litellm_logging_obj),
+        )
diff --git a/litellm/llms/azure_ai/chat/transformation.py b/litellm/llms/azure_ai/chat/transformation.py
index 039c462b38a..00e1c1e25ba 100644
--- a/litellm/llms/azure_ai/chat/transformation.py
+++ b/litellm/llms/azure_ai/chat/transformation.py
@@ -2,7 +2,6 @@ import copy
 import enum
 import re
 from typing import TYPE_CHECKING, Final, cast
-from urllib.parse import urlparse
 
 import httpx
 from httpx import Response
@@ -15,7 +14,10 @@ from litellm.litellm_core_utils.prompt_templates.common_utils import (
     filter_value_from_dict,
 )
 from litellm.llms.azure.common_utils import BaseAzureLLM
-from litellm.llms.azure_ai.common_utils import is_foundry_model_inference_base
+from litellm.llms.azure_ai.common_utils import (
+    api_key_header_for_base,
+    is_foundry_model_inference_base,
+)
 from litellm.llms.base_llm.chat.transformation import LiteLLMLoggingObj
 from litellm.llms.openai.chat.gpt_5_transformation import OpenAIGPT5Config
 from litellm.llms.openai.common_utils import drop_params_from_unprocessable_entity_error
@@ -146,11 +148,7 @@ class AzureAIStudioConfig(OpenAIConfig):
         """
         Returns True if the request should use `api-key` header for authentication.
         """
-        parsed_url: Final = urlparse(api_base)
-        host: Final = parsed_url.hostname
-        if host and (host.endswith(".services.ai.azure.com") or host.endswith(".openai.azure.com")):
-            return True
-        return False
+        return api_key_header_for_base(api_base) == "api-key"
 
     def get_complete_url(
         self,
diff --git a/litellm/llms/azure_ai/common_utils.py b/litellm/llms/azure_ai/common_utils.py
index aa34bab5b2e..0665b3f64c5 100644
--- a/litellm/llms/azure_ai/common_utils.py
+++ b/litellm/llms/azure_ai/common_utils.py
@@ -19,6 +19,13 @@ def is_foundry_model_inference_base(api_base: str) -> bool:
     return "/openai/deployments" not in parsed.path
 
 
+def api_key_header_for_base(api_base: str | None) -> AzureAIApiKeyHeader:
+    host: Final = urlparse(api_base).hostname if api_base else None
+    if host and (host.endswith(".services.ai.azure.com") or host.endswith(".openai.azure.com")):
+        return "api-key"
+    return "Authorization"
+
+
 def get_azure_ai_entra_token(litellm_params: Mapping[str, object] | None = None) -> str | None:
     """
     Resolve an Entra ID / OAuth access token for an Azure AI Foundry deployment.
diff --git a/litellm/llms/azure_ai/cost_calculator.py b/litellm/llms/azure_ai/cost_calculator.py
index 95f536296a2..5934525eca3 100644
--- a/litellm/llms/azure_ai/cost_calculator.py
+++ b/litellm/llms/azure_ai/cost_calculator.py
@@ -11,7 +11,7 @@ from litellm.types.utils import Usage
 from litellm.utils import get_model_info
 
 
-def _is_azure_model_router(model: str) -> bool:
+def is_azure_model_router(model: str) -> bool:
     """
     Check if the model is Azure AI Foundry Model Router.
 
@@ -31,6 +31,18 @@ def _is_azure_model_router(model: str) -> bool:
     return "model-router" in model_lower or "model_router" in model_lower or model_lower == "azure-model-router"
 
 
+ROUTER_FEE_ENTRY_NAMES: Final = frozenset({"model-router", "model_router"})
+
+
+def is_router_fee_entry(model: str) -> bool:
+    return model.lower().removeprefix("azure_ai/") in ROUTER_FEE_ENTRY_NAMES
+
+
+def _router_fee_entry_name(model: str) -> str:
+    entry_name: Final = model.lower().removeprefix("azure_ai/")
+    return entry_name if entry_name in ROUTER_FEE_ENTRY_NAMES else "model_router"
+
+
 def calculate_azure_model_router_flat_cost(model: str, prompt_tokens: int) -> float:
     """
     Calculate the flat cost for Azure AI Foundry Model Router.
@@ -42,20 +54,39 @@ def calculate_azure_model_router_flat_cost(model: str, prompt_tokens: int) -> fl
     Returns:
         float: The flat cost in USD, or 0.0 if not applicable
     """
-    if not _is_azure_model_router(model):
+    if not is_azure_model_router(model):
         return 0.0
-
-    # Get the model router pricing from model_prices_and_context_window.json
-    # Use "model_router" as the key (without actual model name suffix)
-    model_info: Final = get_model_info(model="model_router", custom_llm_provider="azure_ai")
+    model_info: Final = get_model_info(model=_router_fee_entry_name(model), custom_llm_provider="azure_ai")
     router_flat_cost_per_token: Final = model_info.get("input_cost_per_token", 0)
-
     if router_flat_cost_per_token and router_flat_cost_per_token > 0:
         return prompt_tokens * router_flat_cost_per_token
-
     return 0.0
 
 
+def _response_model_cost(model: str, usage: Usage, service_tier: str | None) -> tuple[float, float]:
+    try:
+        return generic_cost_per_token(
+            model=model, usage=usage, custom_llm_provider="azure_ai", service_tier=service_tier
+        )
+    except Exception as e:
+        if not is_azure_model_router(model):
+            raise
+        verbose_logger.debug(
+            "Azure AI Model Router: model '%s' not in cost map, only the routing fee applies. Error: %s", model, e
+        )
+        return 0.0, 0.0
+
+
+def _router_fee_name(model: str, request_model: str | None) -> str | None:
+    if is_router_fee_entry(model):
+        return None
+    if is_azure_model_router(model):
+        return model
+    if request_model is not None and is_azure_model_router(request_model):
+        return request_model
+    return None
+
+
 def cost_per_token(
     model: str,
     usage: Usage,
@@ -64,68 +95,31 @@ def cost_per_token(
     service_tier: str | None = None,
 ) -> tuple[float, float]:
     """
-    Calculate the cost per token for Azure AI models.
+    Price the response model's own tokens for Azure AI, plus the Model Router fee exactly once when either the
+    priced name or request_model is a Model Router name.
 
-    For Azure AI Foundry Model Router:
-    - Adds a flat cost of $0.14 per million input tokens (from model_prices_and_context_window.json)
-    - Plus the cost of the actual model used (handled by generic_cost_per_token)
+    A response priced as the router entry itself already carries the fee, so nothing is added on top of it. A
+    router deployment name that is missing from the cost map prices at the fee alone.
+
+    completion_cost passes only the priced name: when that name is a routed model it adds the fee itself through
+    AzureModelRouterConfig.calculate_additional_costs as the "Azure Model Router Flat Cost" line of the cost
+    breakdown, and when the name is router-shaped the fee is already in the prompt cost returned here.
 
     Args:
         model: str, the model name without provider prefix (from response)
         usage: LiteLLM Usage block
         response_time_ms: Optional response time in milliseconds
-        request_model: Optional[str], the original request model name (to detect router usage)
+        request_model: Optional[str], the original request model name; a Model Router name adds the routing fee
+        service_tier: Optional service tier the request was priced on
 
     Returns:
         Tuple[float, float] - prompt_cost_in_usd, completion_cost_in_usd
 
     Raises:
-        ValueError: If the model is not found in the cost map and cost cannot be calculated
-            (except for Model Router models where we return just the routing flat cost)
+        ValueError: If a model that is not a Model Router name is missing from the cost map
     """
-    prompt_cost = 0.0
-    completion_cost = 0.0
-
-    # Determine if this was a model router request
-    # Check both the response model and the request model
-    is_router_request: Final = _is_azure_model_router(model) or (
-        request_model is not None and _is_azure_model_router(request_model)
-    )
-
-    # Calculate base cost using generic cost calculator
-    # This may raise an exception if the model is not in the cost map
-    try:
-        prompt_cost, completion_cost = generic_cost_per_token(
-            model=model,
-            usage=usage,
-            custom_llm_provider="azure_ai",
-            service_tier=service_tier,
-        )
-    except Exception as e:
-        # For Model Router, the model name (e.g., "azure-model-router") may not be in the cost map
-        # because it's a routing service, not an actual model. In this case, we continue
-        # to calculate just the routing flat cost.
-        if not _is_azure_model_router(model):
-            # Re-raise for non-router models - they should have pricing defined
-            raise
-        verbose_logger.debug(
-            "Azure AI Model Router: model '%s' not in cost map, calculating routing flat cost only. Error: %s", model, e
-        )
-
-    # Add flat cost for Azure Model Router
-    # The flat cost is defined in model_prices_and_context_window.json for azure_ai/model_router
-    if is_router_request:
-        # Use the request model for flat cost calculation if available, otherwise use response model
-        router_model_for_calc: Final = request_model if request_model else model
-        router_flat_cost: Final = calculate_azure_model_router_flat_cost(router_model_for_calc, usage.prompt_tokens)
-
-        if router_flat_cost > 0:
-            verbose_logger.debug(
-                f"Azure AI Model Router flat cost: ${router_flat_cost:.6f} "
-                f"({usage.prompt_tokens} tokens × ${router_flat_cost / usage.prompt_tokens:.9f}/token)"
-            )
-
-            # Add flat cost to prompt cost
-            prompt_cost += router_flat_cost
-
-    return prompt_cost, completion_cost
+    prompt_cost, completion_cost = _response_model_cost(model=model, usage=usage, service_tier=service_tier)
+    fee_name: Final = _router_fee_name(model=model, request_model=request_model)
+    if fee_name is None:
+        return prompt_cost, completion_cost
+    return prompt_cost + calculate_azure_model_router_flat_cost(fee_name, usage.prompt_tokens), completion_cost
diff --git a/litellm/llms/azure_ai/image_edit/__init__.py b/litellm/llms/azure_ai/image_edit/__init__.py
index 51a23859058..fda9335a5d6 100644
--- a/litellm/llms/azure_ai/image_edit/__init__.py
+++ b/litellm/llms/azure_ai/image_edit/__init__.py
@@ -23,7 +23,7 @@ def get_azure_ai_image_edit_config(model: str) -> BaseImageEditConfig:
     """
     Get the appropriate image edit config for an Azure AI model.
 
-    - MAI models use /mai/v1/images/edits with multipart form data and size
+    - MAI models use /mai/v1/images/edits with multipart form data
     - FLUX 2 models use JSON with base64 image
     - FLUX 1 models use multipart/form-data
     """
diff --git a/litellm/llms/azure_ai/image_edit/mai_transformation.py b/litellm/llms/azure_ai/image_edit/mai_transformation.py
index e639c20292b..55b179e9591 100644
--- a/litellm/llms/azure_ai/image_edit/mai_transformation.py
+++ b/litellm/llms/azure_ai/image_edit/mai_transformation.py
@@ -1,4 +1,4 @@
-from typing import TYPE_CHECKING, Any, Final, cast
+from typing import TYPE_CHECKING, Any, Final
 
 import httpx
 from httpx._types import RequestFiles
@@ -13,7 +13,6 @@ from litellm.llms.azure_ai.image_generation.mai_transformation import (
 from litellm.llms.openai.common_utils import OpenAIError
 from litellm.llms.openai.image_edit.transformation import OpenAIImageEditConfig
 from litellm.secret_managers.main import get_secret_str
-from litellm.types.images.main import ImageEditOptionalRequestParams
 from litellm.types.llms.openai import FileTypes
 from litellm.types.router import GenericLiteLLMParams
 from litellm.types.utils import ImageResponse
@@ -26,65 +25,8 @@ if TYPE_CHECKING:
 class AzureFoundryMAIImageEditConfig(OpenAIImageEditConfig):
     """Azure AI Foundry MAI image editing (e.g. MAI-Image-2.5)."""
 
-    DEFAULT_SIZE = "1024x1024"
-
     def get_supported_openai_params(self, model: str) -> list:
-        return ["prompt", "image", "model", "n", "size"]
-
-    def map_openai_params(
-        self,
-        image_edit_optional_params: ImageEditOptionalRequestParams,
-        model: str,
-        drop_params: bool,
-    ) -> dict:
-        optional_params: Final[dict[str, Any]] = {}
-        supported_params: Final = self.get_supported_openai_params(model)
-
-        for key, value in dict(image_edit_optional_params).items():
-            if value is None or key in optional_params:
-                continue
-
-            if key in supported_params:
-                if key == "size" and value:
-                    size_param = cast(str, value)
-                    self._validate_size_param(size_param)
-                    optional_params[key] = size_param
-                else:
-                    optional_params[key] = value
-            elif not drop_params:
-                raise ValueError(
-                    f"Parameter {key} is not supported for model {model}. "
-                    f"Supported parameters are {supported_params}. "
-                    f"Set drop_params=True to drop unsupported parameters."
-                )
-
-        if "size" not in optional_params:
-            optional_params["size"] = self.DEFAULT_SIZE
-
-        return optional_params
-
-    def _validate_size_param(self, size: str) -> None:
-        known_sizes: Final = {
-            "1024x1024",
-            "1792x1024",
-            "1024x1792",
-            "512x512",
-            "256x256",
-        }
-
-        if size in known_sizes:
-            return
-
-        if "x" in size:
-            try:
-                tuple(map(int, size.lower().split("x", 1)))
-                return
-            except ValueError:
-                raise ValueError(f"Invalid size format: '{size}'. Expected format 'WIDTHxHEIGHT' (e.g., '1024x1024').")
-
-        raise ValueError(
-            f"Unsupported size value: '{size}'. Use a known size (e.g., '1024x1024') or a custom 'WIDTHxHEIGHT' string."
-        )
+        return ["prompt", "image", "model", "n"]
 
     def validate_environment(
         self,
diff --git a/litellm/llms/azure_ai/image_generation/mai_transformation.py b/litellm/llms/azure_ai/image_generation/mai_transformation.py
index 64f81956ad7..67b1a8bcab3 100644
--- a/litellm/llms/azure_ai/image_generation/mai_transformation.py
+++ b/litellm/llms/azure_ai/image_generation/mai_transformation.py
@@ -2,6 +2,7 @@ from typing import TYPE_CHECKING, Any, Final
 
 import httpx
 
+from litellm.exceptions import UnsupportedParamsError
 from litellm.llms.base_llm.image_generation.transformation import (
     BaseImageGenerationConfig,
 )
@@ -21,6 +22,10 @@ class AzureFoundryMAIImageGenerationConfig(BaseImageGenerationConfig):
     DEFAULT_WIDTH = 1024
     DEFAULT_HEIGHT = 1024
 
+    MAX_IMAGES_PER_REQUEST: Final = 1
+    MIN_DIMENSION_PX: Final = 768
+    MAX_TOTAL_PX: Final = 1_056_768
+
     @staticmethod
     def get_mai_image_generation_url(
         api_base: str | None,
@@ -145,16 +150,27 @@ class AzureFoundryMAIImageGenerationConfig(BaseImageGenerationConfig):
 
             if k in supported_params:
                 if k == "size" and v:
-                    self._map_size_param(v, optional_params)
+                    self._map_size_param(v, optional_params, model)
+                elif k == "n" and v is not None and self._image_count(v, model) != self.MAX_IMAGES_PER_REQUEST:
+                    if not drop_params:
+                        raise self._unsupported(
+                            model,
+                            f"n={v} is not supported for model {model}. The Azure AI MAI image "
+                            f"endpoint returns exactly {self.MAX_IMAGES_PER_REQUEST} image per "
+                            "request and ignores any count, so a larger value would silently "
+                            "return fewer images than requested. Send one request per image, or "
+                            "set drop_params=True to drop n.",
+                        )
                 else:
                     optional_params[k] = v
             elif k in ("width", "height"):
                 optional_params[k] = v
             elif not drop_params:
-                raise ValueError(
+                raise self._unsupported(
+                    model,
                     f"Parameter {k} is not supported for model {model}. "
                     f"Supported parameters are {supported_params} and width/height. "
-                    f"Set drop_params=True to drop unsupported parameters."
+                    f"Set drop_params=True to drop unsupported parameters.",
                 )
 
         if "width" not in optional_params:
@@ -165,7 +181,19 @@ class AzureFoundryMAIImageGenerationConfig(BaseImageGenerationConfig):
         optional_params.pop("size", None)
         return optional_params
 
-    def _map_size_param(self, size: str, optional_params: dict) -> None:
+    @staticmethod
+    def _unsupported(model: str, message: str) -> UnsupportedParamsError:
+        return UnsupportedParamsError(message=message, llm_provider="azure_ai", model=model)
+
+    def _image_count(self, n: object, model: str) -> int:
+        if isinstance(n, int):
+            return n
+        try:
+            return int(str(n))
+        except ValueError:
+            raise self._unsupported(model, f"n={n!r} is not a whole number of images for model {model}.")
+
+    def _map_size_param(self, size: str, optional_params: dict, model: str) -> None:
         size_mapping: Final = {
             "1024x1024": (1024, 1024),
             "1792x1024": (1792, 1024),
@@ -176,19 +204,36 @@ class AzureFoundryMAIImageGenerationConfig(BaseImageGenerationConfig):
 
         if size in size_mapping:
             width, height = size_mapping[size]
-            optional_params["width"] = width
-            optional_params["height"] = height
         elif "x" in size:
             try:
                 width, height = map(int, size.lower().split("x"))
-                optional_params["width"] = width
-                optional_params["height"] = height
             except ValueError:
-                raise ValueError(f"Invalid size format: '{size}'. Expected format 'WIDTHxHEIGHT' (e.g., '1024x1024').")
+                raise self._unsupported(
+                    model, f"Invalid size format: '{size}'. Expected format 'WIDTHxHEIGHT' (e.g., '1024x1024')."
+                )
         else:
-            raise ValueError(
+            raise self._unsupported(
+                model,
                 f"Unsupported size value: '{size}'. "
-                f"Use a known size (e.g., '1024x1024') or a custom 'WIDTHxHEIGHT' string."
+                f"Use a known size (e.g., '1024x1024') or a custom 'WIDTHxHEIGHT' string.",
+            )
+
+        self._validate_dimensions(model=model, size=size, width=width, height=height)
+        optional_params["width"] = width
+        optional_params["height"] = height
+
+    def _validate_dimensions(self, model: str, size: str, width: int, height: int) -> None:
+        if width < self.MIN_DIMENSION_PX or height < self.MIN_DIMENSION_PX:
+            raise self._unsupported(
+                model,
+                f"Unsupported size value: '{size}'. Azure AI MAI image models require width and "
+                f"height of at least {self.MIN_DIMENSION_PX} pixels.",
+            )
+        if width * height > self.MAX_TOTAL_PX:
+            raise self._unsupported(
+                model,
+                f"Unsupported size value: '{size}'. Azure AI MAI image models accept at most "
+                f"{self.MAX_TOTAL_PX} total pixels ({width}x{height} is {width * height}).",
             )
 
     def transform_image_generation_response(
diff --git a/litellm/llms/azure_ai/passthrough/transformation.py b/litellm/llms/azure_ai/passthrough/transformation.py
new file mode 100644
index 00000000000..f2be1d95593
--- /dev/null
+++ b/litellm/llms/azure_ai/passthrough/transformation.py
@@ -0,0 +1,232 @@
+from __future__ import annotations
+
+from collections.abc import Callable, Mapping, Sequence
+from types import MappingProxyType
+from typing import TYPE_CHECKING, Final
+
+import httpx
+from pydantic import BaseModel, ConfigDict, TypeAdapter, ValidationError
+
+from litellm._logging import verbose_logger
+from litellm.llms.azure_ai.common_utils import (
+    AzureFoundryModelInfo,
+    api_key_header_for_base,
+    get_azure_ai_auth_headers,
+)
+from litellm.llms.azure_ai.ocr.common_utils import get_azure_ai_ocr_config
+from litellm.llms.base_llm.passthrough.transformation import (
+    BasePassthroughConfig,
+    RelayShape,
+    logged_relay_shape,
+    strip_leading_model_segment,
+)
+from litellm.types.llms.openai import AllMessageValues
+from litellm.types.rerank import RerankResponse
+from litellm.types.utils import CallTypes, ImageResponse, StandardPassThroughResponseObject
+
+if TYPE_CHECKING:
+    from httpx import URL, Response
+
+    from litellm.litellm_core_utils.litellm_logging import Logging
+    from litellm.llms.base_llm.ocr.transformation import BaseOCRConfig, OCRResponse
+    from litellm.llms.base_llm.passthrough.transformation import LoggedRelayResponse
+
+
+EMPTY_QUERY: Final[Mapping[str, object]] = MappingProxyType({})
+
+
+class PassthroughMetadata(BaseModel):
+    model_config = ConfigDict(extra="ignore")
+
+    model_group: str = ""
+
+
+def model_group_from(litellm_params: Mapping[str, object]) -> str:
+    try:
+        return PassthroughMetadata.model_validate(litellm_params.get("litellm_metadata")).model_group
+    except ValidationError:
+        return ""
+
+
+def api_version_from(litellm_params: Mapping[str, object]) -> str | None:
+    try:
+        return TypeAdapter(str | None).validate_python(litellm_params.get("api_version"))
+    except ValidationError:
+        return None
+
+
+def foundry_root(api_base: str) -> str:
+    url: Final = httpx.URL(api_base)
+    segments: Final = tuple(segment for segment in url.path.split("/") if segment)
+    root_segments: Final = segments[: segments.index("models")] if "models" in segments else segments
+    return str(url.copy_with(path="/" + "/".join(root_segments), query=None)).rstrip("/")
+
+
+def is_repeated_native_prefix(native_segments: tuple[str, ...], overlap: int) -> bool:
+    return overlap == len(native_segments) or native_segments[0] == "openai"
+
+
+def without_repeated_native_prefix(root: str, native_endpoint: str) -> str:
+    url: Final = httpx.URL(root)
+    root_segments: Final = tuple(segment for segment in url.path.split("/") if segment)
+    native_segments: Final = tuple(segment.casefold() for segment in native_endpoint.split("/") if segment)
+    overlap: Final = next(
+        (
+            length
+            for length in range(min(len(root_segments), len(native_segments)), 0, -1)
+            if tuple(segment.casefold() for segment in root_segments[-length:]) == native_segments[:length]
+            and is_repeated_native_prefix(native_segments, length)
+        ),
+        0,
+    )
+    kept_segments: Final = root_segments[: len(root_segments) - overlap]
+    return str(url.copy_with(path="/" + "/".join(kept_segments), query=None)).rstrip("/")
+
+
+def relay_query_params(
+    request_query_params: Mapping[str, object] | None,
+    deployment_api_version: str | None,
+    api_base: str,
+) -> Mapping[str, object] | None:
+    if request_query_params and "api-version" in request_query_params:
+        return request_query_params
+    api_version: Final = deployment_api_version or httpx.URL(api_base).params.get("api-version")
+    if api_version is None:
+        return request_query_params
+    return MappingProxyType({**(request_query_params or EMPTY_QUERY), "api-version": api_version})
+
+
+def relayed_body(httpx_response: Response) -> str | dict:
+    try:
+        body: Final[object] = httpx_response.json()
+    except ValueError:
+        return httpx_response.text
+    return body if isinstance(body, dict) else httpx_response.text
+
+
+FOUNDRY_RELAY_SHAPES: Final = (
+    RelayShape("/rerank", CallTypes.arerank, RerankResponse.model_validate),
+    RelayShape("/providers/blackforestlabs/v1/flux-2-pro", CallTypes.aimage_generation, ImageResponse.model_validate),
+)
+
+
+class AzureAIPassthroughConfig(AzureFoundryModelInfo, BasePassthroughConfig):
+    def __init__(self, ocr_config_for: Callable[[str], BaseOCRConfig | None] = get_azure_ai_ocr_config) -> None:
+        super().__init__()
+        self.ocr_config_for: Final = ocr_config_for
+
+    def is_streaming_request(self, endpoint: str, request_data: Mapping[str, object]) -> bool:
+        return bool(request_data.get("stream"))
+
+    def get_complete_url(
+        self,
+        api_base: str | None,
+        api_key: str | None,
+        model: str,
+        endpoint: str,
+        request_query_params: Mapping[str, object] | None,
+        litellm_params: Mapping[str, object],
+    ) -> tuple[URL, str]:
+        base_target_url: Final = self.get_api_base(api_base)
+        if base_target_url is None:
+            raise ValueError("Azure AI api base not found: set `api_base` on the deployment or AZURE_AI_API_BASE")
+
+        native_endpoint: Final = strip_leading_model_segment(endpoint, (model, model_group_from(litellm_params)))
+        root: Final = without_repeated_native_prefix(foundry_root(base_target_url), native_endpoint)
+        query_params: Final = relay_query_params(
+            request_query_params, api_version_from(litellm_params), base_target_url
+        )
+        return (self.format_url(native_endpoint, root, query_params), root)
+
+    def validate_environment(
+        self,
+        headers: Mapping[str, str],
+        model: str,
+        messages: Sequence[AllMessageValues],
+        optional_params: Mapping[str, object],
+        litellm_params: Mapping[str, object],
+        api_key: str | None = None,
+        api_base: str | None = None,
+    ) -> dict[str, str]:  # mutable-ok: base class contract returns dict for httpx
+        auth_headers: Final = get_azure_ai_auth_headers(
+            api_key=api_key,
+            litellm_params=litellm_params,
+            api_key_header=api_key_header_for_base(api_base),
+        )
+        return {**headers, **auth_headers}  # mutable-ok: base class contract returns dict for httpx
+
+    def logging_non_streaming_response(
+        self,
+        model: str,
+        custom_llm_provider: str,
+        httpx_response: Response,
+        request_data: Mapping[str, object],
+        logging_obj: Logging,
+        endpoint: str,
+    ) -> LoggedRelayResponse | OCRResponse | StandardPassThroughResponseObject | None:
+        from litellm.llms.azure.passthrough.transformation import AzurePassthroughConfig
+
+        chat_result: Final = AzurePassthroughConfig().logging_non_streaming_response(  # pyright: ignore[reportUnknownMemberType]  # the Azure config still types request_data as a bare dict
+            model=model,
+            custom_llm_provider=custom_llm_provider,
+            httpx_response=httpx_response,
+            request_data=dict(request_data),  # mutable-ok: AzurePassthroughConfig wants a dict
+            logging_obj=logging_obj,
+            endpoint=endpoint,
+        )
+        if chat_result is not None:
+            return chat_result
+        ocr_result: Final = self.logged_ocr_response(model, httpx_response, logging_obj, endpoint)
+        if ocr_result is not None:
+            return ocr_result
+        foundry_result: Final = logged_relay_shape(FOUNDRY_RELAY_SHAPES, httpx_response, logging_obj, endpoint)
+        if foundry_result is not None:
+            return foundry_result
+        return StandardPassThroughResponseObject(response=relayed_body(httpx_response))
+
+    def logged_ocr_response(
+        self, model: str, httpx_response: Response, logging_obj: Logging, endpoint: str
+    ) -> OCRResponse | None:
+        ocr_config: Final = self.ocr_config_for(model)
+        if ocr_config is None or httpx_response.status_code != 200:
+            return None
+        relayed_url: Final = httpx_response.request.url
+        relayed_origin: Final = str(relayed_url.copy_with(path="/", query=None, fragment=None)).rstrip("/")
+        ocr_url: Final = httpx.URL(
+            ocr_config.get_complete_url(
+                api_base=relayed_origin,
+                model=model,
+                optional_params={},  # mutable-ok: BaseOCRConfig wants a dict
+            )
+        )
+        known_prefixes: Final = (model, model_group_from(logging_obj.litellm_params))
+        native_endpoint: Final = strip_leading_model_segment(endpoint, known_prefixes)
+        if f"/{native_endpoint.strip('/')}" != ocr_url.path:
+            return None
+        try:
+            ocr_response: Final = ocr_config.transform_ocr_response(
+                model=model, raw_response=httpx_response, logging_obj=logging_obj
+            )
+        except (ValueError, AttributeError) as error:
+            verbose_logger.warning("azure_ai passthrough: OCR body from %s is not costable: %s", ocr_url, error)
+            return None
+        logging_obj.call_type = CallTypes.aocr.value  # rebind-ok: routes cost calculation to the per-page OCR path
+        return ocr_response
+
+    def handle_logging_collected_chunks(
+        self,
+        all_chunks: Sequence[str],
+        litellm_logging_obj: Logging,
+        model: str,
+        custom_llm_provider: str,
+        endpoint: str,
+    ) -> LoggedRelayResponse | None:
+        from litellm.llms.azure.passthrough.transformation import AzurePassthroughConfig
+
+        return AzurePassthroughConfig().handle_logging_collected_chunks(
+            all_chunks=all_chunks,
+            litellm_logging_obj=litellm_logging_obj,
+            model=model,
+            custom_llm_provider=custom_llm_provider,
+            endpoint=endpoint,
+        )
diff --git a/litellm/llms/base_llm/guardrail_translation/base_translation.py b/litellm/llms/base_llm/guardrail_translation/base_translation.py
index afd8e0f67f7..f1143425ced 100644
--- a/litellm/llms/base_llm/guardrail_translation/base_translation.py
+++ b/litellm/llms/base_llm/guardrail_translation/base_translation.py
@@ -52,13 +52,28 @@ class StreamingScanKey:
 
 
 class BaseTranslation(ABC):
-    delivers_ended_stream_text_rewrites: ClassVar[bool] = False
+    delivers_ended_stream_rewrites: ClassVar[bool] = False
     """Whether ``process_output_streaming_response`` accepts
     ``deliver_ended_stream_rewrites=True`` and, on an ended (fully buffered)
-    stream, writes guardrail text rewrites back across ``responses_so_far`` so
-    a buffered pipeline can release rewritten chunks. Tool-call rewrites, and
-    text rewrites on every other translation, are undeliverable: the pipeline
-    executor discards them and releases the original chunks."""
+    stream, writes guardrail text and tool-call rewrites back across
+    ``responses_so_far`` so a buffered pipeline can release rewritten chunks,
+    raising ``UndeliverableStreamRewrite`` for a shape it cannot place. Rewrites
+    on every other translation are undeliverable: the pipeline executor
+    discards them and releases the original chunks."""
+
+    assembles_streamed_response: ClassVar[bool] = False
+    """Whether ``process_output_streaming_response`` stores the assembled response of an
+    ended stream under ``request_data["response"]`` before scanning it, the way the chat,
+    Responses, and Messages translations do. A streaming pipeline runs a guardrail that only
+    has the legacy post-call hook against that response, so on a translation without it such
+    a guardrail keeps running on its own."""
+
+    def post_call_hook_response(self, response: object) -> object:
+        """The ``response`` this endpoint's non-streaming post-call hooks receive, derived from
+        the object the translation stores under ``request_data["response"]`` while scanning an
+        ended stream. Chat and Responses scan that shape already; a translation that scans a
+        different one (Messages scans an OpenAI-shaped ModelResponse) overrides this."""
+        return response
 
     @staticmethod
     def transform_user_api_key_dict_to_metadata(
@@ -175,9 +190,9 @@ class BaseTranslation(ABC):
         transformations (see ``StreamTransformSink``); base handlers ignore it.
         ``deliver_ended_stream_rewrites`` is passed True only when the caller
         holds the whole buffered stream and the subclass declares
-        ``delivers_ended_stream_text_rewrites``: the handler then writes
-        guardrail text rewrites back across ``responses_so_far`` instead of
-        discarding them.
+        ``delivers_ended_stream_rewrites``: the handler then writes
+        guardrail text and tool-call rewrites back across ``responses_so_far``
+        instead of discarding them.
         """
         return responses_so_far
 
diff --git a/litellm/llms/base_llm/passthrough/transformation.py b/litellm/llms/base_llm/passthrough/transformation.py
index adbf2e126fb..20180c5cfa2 100644
--- a/litellm/llms/base_llm/passthrough/transformation.py
+++ b/litellm/llms/base_llm/passthrough/transformation.py
@@ -1,5 +1,14 @@
+from __future__ import annotations
+
+import re
 from abc import abstractmethod
-from typing import TYPE_CHECKING, Final, Optional, Union
+from collections.abc import Callable, Mapping, Sequence
+from dataclasses import dataclass
+from typing import TYPE_CHECKING, Final, TypeAlias
+
+from pydantic import TypeAdapter, ValidationError
+
+from litellm.types.utils import CallTypes
 
 from ..base_utils import BaseLLMModelInfo
 
@@ -7,9 +16,68 @@ if TYPE_CHECKING:
     from httpx import URL, Headers, Response
 
     from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
-    from litellm.types.utils import CostResponseTypes
+    from litellm.types.llms.openai import ResponsesAPIResponse, ResponsesTerminalEvent
+    from litellm.types.rerank import RerankResponse
+    from litellm.types.utils import CostResponseTypes, StandardPassThroughResponseObject
 
     from ..chat.transformation import BaseLLMException
+    from ..ocr.transformation import OCRResponse
+
+    LoggedRelayResponse: TypeAlias = CostResponseTypes | RerankResponse | ResponsesAPIResponse | ResponsesTerminalEvent
+
+
+RELAYED_JSON_OBJECT: Final = TypeAdapter(Mapping[str, object])
+
+
+def strip_leading_model_segment(endpoint: str, model_names: tuple[str, ...]) -> str:
+    path: Final = endpoint.lstrip("/")
+    for model_name in model_names:
+        if not model_name:
+            continue
+        if path == model_name:
+            return ""
+        if path.startswith(f"{model_name}/"):
+            return path[len(model_name) + 1 :]
+    return path
+
+
+def replace_path_segment(endpoint: str, segment: str, replacement: str) -> str:
+    bounded_segment: Final = re.compile(rf"(?<![^/]){re.escape(segment)}(?![^/:])")
+    return bounded_segment.sub(lambda _: replacement, endpoint)
+
+
+def relayed_json_object(httpx_response: Response) -> Mapping[str, object] | None:
+    if httpx_response.status_code != 200:
+        return None
+    try:
+        return RELAYED_JSON_OBJECT.validate_python(httpx_response.json())
+    except (ValueError, ValidationError):
+        return None
+
+
+@dataclass(frozen=True, slots=True)
+class RelayShape:
+    path_suffix: str
+    call_type: CallTypes
+    parse: Callable[[Mapping[str, object]], LoggedRelayResponse]
+
+
+def logged_relay_shape(
+    shapes: Sequence[RelayShape], httpx_response: Response, logging_obj: LiteLLMLoggingObj, endpoint: str
+) -> LoggedRelayResponse | None:
+    relayed_path: Final = f"/{endpoint.strip('/')}"
+    shape: Final = next((candidate for candidate in shapes if relayed_path.endswith(candidate.path_suffix)), None)
+    body: Final = relayed_json_object(httpx_response) if shape else None
+    if shape is None or body is None:
+        return None
+    try:
+        parsed: Final = shape.parse(body)
+    except ValidationError:
+        return None
+    logging_obj.call_type = (
+        shape.call_type.value
+    )  # rebind-ok: routes cost calculation to the relayed shape's pricing path
+    return parsed
 
 
 class BasePassthroughConfig(BaseLLMModelInfo):
@@ -23,8 +91,8 @@ class BasePassthroughConfig(BaseLLMModelInfo):
         self,
         endpoint: str,
         base_target_url: str,
-        request_query_params: dict | None,
-    ) -> "URL":
+        request_query_params: Mapping[str, object] | None,
+    ) -> URL:
         """
         Helper function to add query params to the url
         Args:
@@ -58,7 +126,7 @@ class BasePassthroughConfig(BaseLLMModelInfo):
         endpoint: str,
         request_query_params: dict | None,
         litellm_params: dict,
-    ) -> tuple["URL", str]:
+    ) -> tuple[URL, str]:
         """
         Get the complete url for the request
         Returns:
@@ -88,9 +156,7 @@ class BasePassthroughConfig(BaseLLMModelInfo):
         """
         return headers, None
 
-    def get_error_class(
-        self, error_message: str, status_code: int, headers: Union[dict, "Headers"]
-    ) -> "BaseLLMException":
+    def get_error_class(self, error_message: str, status_code: int, headers: dict | Headers) -> BaseLLMException:
         from litellm.llms.base_llm.chat.transformation import BaseLLMException
 
         return BaseLLMException(status_code=status_code, message=error_message, headers=headers)
@@ -99,21 +165,21 @@ class BasePassthroughConfig(BaseLLMModelInfo):
         self,
         model: str,
         custom_llm_provider: str,
-        httpx_response: "Response",
+        httpx_response: Response,
         request_data: dict,
-        logging_obj: "LiteLLMLoggingObj",
+        logging_obj: LiteLLMLoggingObj,
         endpoint: str,
-    ) -> Optional["CostResponseTypes"]:
+    ) -> LoggedRelayResponse | OCRResponse | StandardPassThroughResponseObject | None:
         pass
 
     def handle_logging_collected_chunks(
         self,
         all_chunks: list[str],
-        litellm_logging_obj: "LiteLLMLoggingObj",
+        litellm_logging_obj: LiteLLMLoggingObj,
         model: str,
         custom_llm_provider: str,
         endpoint: str,
-    ) -> Optional["CostResponseTypes"]:
+    ) -> LoggedRelayResponse | None:
         return None
 
     def _convert_raw_bytes_to_str_lines(self, raw_bytes: list[bytes]) -> list[str]:
diff --git a/litellm/llms/base_llm/responses/transformation.py b/litellm/llms/base_llm/responses/transformation.py
index 1365941fe2a..14f00aaaa21 100644
--- a/litellm/llms/base_llm/responses/transformation.py
+++ b/litellm/llms/base_llm/responses/transformation.py
@@ -62,6 +62,9 @@ class BaseResponsesAPIConfig(ABC):
         """
         return False
 
+    def supports_encrypted_agent_messages(self) -> bool:
+        return False
+
     def sign_request(
         self,
         headers: dict,
diff --git a/litellm/llms/bedrock/base_aws_llm.py b/litellm/llms/bedrock/base_aws_llm.py
index a197702921f..f52c1cec6a8 100644
--- a/litellm/llms/bedrock/base_aws_llm.py
+++ b/litellm/llms/bedrock/base_aws_llm.py
@@ -1,21 +1,27 @@
+import asyncio
 import base64
+import contextvars
 import hashlib
 import json
 import os
 import re
 import urllib.parse
-from collections.abc import Callable, Mapping
+from collections.abc import Callable, Mapping, Sequence
+from concurrent.futures import ThreadPoolExecutor
 from datetime import datetime
+from functools import partial
 from threading import Lock
-from typing import TYPE_CHECKING, Any, ClassVar, Final, Literal, cast, get_args, overload
+from typing import TYPE_CHECKING, Any, ClassVar, Final, Literal, ParamSpec, TypeVar, cast, get_args, overload
 
 import httpx
-from pydantic import BaseModel, ValidationError
+from pydantic import BaseModel, TypeAdapter, ValidationError
+from typing_extensions import NotRequired, ReadOnly, TypedDict
 
 from litellm._logging import verbose_logger
 from litellm.caching.caching import DualCache
 from litellm.caching.in_memory_cache import InMemoryCache
 from litellm.constants import (
+    AWS_SIGNING_MAX_THREADS,
     BEDROCK_EMBEDDING_PROVIDERS_LITERAL,
     BEDROCK_IAM_CACHE_FETCH_LOCK_STRIPES,
     BEDROCK_IAM_CACHE_MAX_ENTRIES,
@@ -26,6 +32,7 @@ from litellm.constants import (
 from litellm.litellm_core_utils.aws_partition import contains_bedrock_arn, get_aws_dns_suffix
 from litellm.litellm_core_utils.dd_tracing import tracer
 from litellm.secret_managers.main import get_secret, get_secret_str
+from litellm.types.llms.bedrock import AwsSessionTag
 
 if TYPE_CHECKING:
     from botocore.awsrequest import AWSPreparedRequest
@@ -47,6 +54,47 @@ _STS_REGION_FROM_ENDPOINT_PATTERN: Final = re.compile(
 
 SIGV4_COMPUTED_HEADERS: Final = frozenset({"authorization", "x-amz-date", "x-amz-security-token", "date"})
 
+_AWS_SESSION_TAGS_ADAPTER: Final[TypeAdapter[tuple[AwsSessionTag, ...]]] = TypeAdapter(tuple[AwsSessionTag, ...])
+
+
+def _canonical_aws_session_tags(raw_tags: object) -> tuple[AwsSessionTag, ...] | None:
+    if raw_tags is None:
+        return None
+    try:
+        validated: Final = _AWS_SESSION_TAGS_ADAPTER.validate_python(raw_tags)
+    except ValidationError as e:
+        raise ValueError(
+            "Invalid 'aws_session_tags' value. Expected a list of {'Key': <str>, 'Value': <str>} dicts, "
+            f"e.g. [{{'Key': 'team', 'Value': 'genai'}}]. Got: {raw_tags!r}"
+        ) from e
+    return tuple(sorted(validated, key=lambda tag: tag["Key"]))
+
+
+class _AssumeRoleParams(TypedDict):
+    RoleArn: ReadOnly[str]
+    RoleSessionName: ReadOnly[str]
+    ExternalId: ReadOnly[NotRequired[str]]
+    Tags: ReadOnly[NotRequired[tuple[AwsSessionTag, ...]]]
+
+
+def _assume_role_params(
+    aws_role_name: str,
+    aws_session_name: str,
+    aws_external_id: str | None,
+    aws_session_tags: Sequence[AwsSessionTag] | None,
+) -> _AssumeRoleParams:
+    match (aws_external_id, tuple(aws_session_tags or ())):
+        case (None, ()):
+            return _AssumeRoleParams(RoleArn=aws_role_name, RoleSessionName=aws_session_name)
+        case (None, tags):
+            return _AssumeRoleParams(RoleArn=aws_role_name, RoleSessionName=aws_session_name, Tags=tags)
+        case (external_id, ()):
+            return _AssumeRoleParams(RoleArn=aws_role_name, RoleSessionName=aws_session_name, ExternalId=external_id)
+        case (external_id, tags):
+            return _AssumeRoleParams(
+                RoleArn=aws_role_name, RoleSessionName=aws_session_name, ExternalId=external_id, Tags=tags
+            )
+
 
 class BedrockRequestTarget(BaseModel):
     aws_region_name: str
@@ -80,7 +128,11 @@ class AwsAuthError(Exception):
         super().__init__(self.message)  # Call the base class constructor with the parameters it needs
 
 
-class BaseAWSLLM:
+class SignsRequestsWithAWS:
+    pass
+
+
+class BaseAWSLLM(SignsRequestsWithAWS):
     # Process-wide IAM credential cache (shared across instances — Bedrock passthrough is per-request).
     # Storage is in-process memory only: no Redis backend unless attached elsewhere. Entry TTL: static
     # access-key + secret + region use ``_get_default_ttl_for_boto3_credentials`` (~59 minutes); ambient
@@ -120,6 +172,7 @@ class BaseAWSLLM:
             "aws_sts_endpoint",
             "aws_bedrock_runtime_endpoint",
             "aws_external_id",
+            "aws_session_tags",
         ]
 
     def _get_ssl_verify(self, ssl_verify: bool | str | None = None):
@@ -137,7 +190,7 @@ class BaseAWSLLM:
 
         return get_ssl_verify(ssl_verify=ssl_verify)
 
-    def get_cache_key(self, credential_args: Mapping[str, str | bool | None]) -> str:
+    def get_cache_key(self, credential_args: Mapping[str, str | bool | tuple[AwsSessionTag, ...] | None]) -> str:
         """
         Generate a unique cache key based on the credential arguments.
         """
@@ -147,7 +200,7 @@ class BaseAWSLLM:
 
     def _get_or_set_cached_credentials(
         self,
-        credential_args: Mapping[str, str | bool | None],
+        credential_args: Mapping[str, str | bool | tuple[AwsSessionTag, ...] | None],
         credential_fetcher: Callable[[], tuple[Credentials, int | None]],
     ) -> Any:
         """
@@ -222,6 +275,7 @@ class BaseAWSLLM:
         aws_web_identity_token: str | None = None,
         aws_sts_endpoint: str | None = None,
         aws_external_id: str | None = None,
+        aws_session_tags: Sequence[AwsSessionTag] | None = None,
         ssl_verify: bool | str | None = None,
     ):
         """
@@ -258,6 +312,7 @@ class BaseAWSLLM:
                 (aws_external_id, "AWS_EXTERNAL_ID"),
             )
         )
+        session_tags: Final = _canonical_aws_session_tags(aws_session_tags)
 
         verbose_logger.debug(
             "in get credentials\n"
@@ -270,7 +325,8 @@ class BaseAWSLLM:
             "aws_role_name=%s\n"
             "aws_web_identity_token=[set=%s]\n"
             "aws_sts_endpoint=%s\n"
-            "aws_external_id=%s",
+            "aws_external_id=%s\n"
+            "aws_session_tags=%s",
             aws_access_key_id is not None,
             aws_secret_access_key is not None,
             aws_session_token is not None,
@@ -281,6 +337,7 @@ class BaseAWSLLM:
             aws_web_identity_token is not None,
             aws_sts_endpoint,
             aws_external_id,
+            session_tags,
         )
 
         args: Final = {
@@ -294,6 +351,7 @@ class BaseAWSLLM:
             "aws_web_identity_token": aws_web_identity_token,
             "aws_sts_endpoint": aws_sts_endpoint,
             "aws_external_id": aws_external_id,
+            "aws_session_tags": session_tags,
             "ssl_verify": ssl_verify,
         }
 
@@ -336,6 +394,7 @@ class BaseAWSLLM:
                     aws_region_name=aws_region_name,
                     aws_sts_endpoint=aws_sts_endpoint,
                     aws_external_id=aws_external_id,
+                    aws_session_tags=session_tags,
                     ssl_verify=ssl_verify,
                 ),
             )
@@ -980,6 +1039,7 @@ class BaseAWSLLM:
         aws_sts_endpoint: str | None = None,
         ssl_verify: bool | str | None = None,
         aws_region_name: str | None = None,
+        aws_session_tags: Sequence[AwsSessionTag] | None = None,
     ) -> dict:
         """Handle cross-account role assumption for IRSA."""
         import boto3
@@ -1032,16 +1092,9 @@ class BaseAWSLLM:
 
         # Now assume the target role
         verbose_logger.debug("Attempting to assume target role: %s with session: %s", aws_role_name, aws_session_name)
-        assume_role_params: Final = {
-            "RoleArn": aws_role_name,
-            "RoleSessionName": aws_session_name,
-        }
-
-        # Add ExternalId parameter if provided
-        if aws_external_id is not None:
-            assume_role_params["ExternalId"] = aws_external_id
-
-        return sts_client_with_creds.assume_role(**assume_role_params)
+        return sts_client_with_creds.assume_role(
+            **_assume_role_params(aws_role_name, aws_session_name, aws_external_id, aws_session_tags)
+        )
 
     def _handle_irsa_same_account(
         self,
@@ -1051,6 +1104,7 @@ class BaseAWSLLM:
         aws_sts_endpoint: str | None = None,
         ssl_verify: bool | str | None = None,
         aws_region_name: str | None = None,
+        aws_session_tags: Sequence[AwsSessionTag] | None = None,
     ) -> dict:
         """Handle same-account role assumption for IRSA."""
         import boto3
@@ -1074,16 +1128,9 @@ class BaseAWSLLM:
 
         # Assume the role
         verbose_logger.debug("Attempting to assume role: %s with session: %s", aws_role_name, aws_session_name)
-        assume_role_params: Final = {
-            "RoleArn": aws_role_name,
-            "RoleSessionName": aws_session_name,
-        }
-
-        # Add ExternalId parameter if provided
-        if aws_external_id is not None:
-            assume_role_params["ExternalId"] = aws_external_id
-
-        return sts_client.assume_role(**assume_role_params)
+        return sts_client.assume_role(
+            **_assume_role_params(aws_role_name, aws_session_name, aws_external_id, aws_session_tags)
+        )
 
     def _extract_credentials_and_ttl(self, sts_response: dict) -> tuple[Credentials, int | None]:
         """Extract credentials and TTL from STS response.
@@ -1118,6 +1165,7 @@ class BaseAWSLLM:
         aws_region_name: str | None,
         aws_sts_endpoint: str | None,
         aws_external_id: str | None,
+        aws_session_tags: tuple[AwsSessionTag, ...] | None,
         ssl_verify: bool | str | None,
     ) -> tuple[Credentials, int | None]:
         """
@@ -1144,6 +1192,7 @@ class BaseAWSLLM:
             aws_region_name=aws_region_name,
             aws_sts_endpoint=aws_sts_endpoint,
             aws_external_id=aws_external_id,
+            aws_session_tags=aws_session_tags,
             ssl_verify=ssl_verify,
         )
 
@@ -1159,6 +1208,7 @@ class BaseAWSLLM:
         aws_sts_endpoint: str | None = None,
         aws_external_id: str | None = None,
         ssl_verify: bool | str | None = None,
+        aws_session_tags: Sequence[AwsSessionTag] | None = None,
     ) -> tuple[Credentials, int | None]:
         """
         Authenticate with AWS Role
@@ -1189,6 +1239,7 @@ class BaseAWSLLM:
                         aws_sts_endpoint=aws_sts_endpoint,
                         ssl_verify=ssl_verify,
                         aws_region_name=aws_region_name,
+                        aws_session_tags=aws_session_tags,
                     )
                 else:
                     sts_response = self._handle_irsa_same_account(
@@ -1198,6 +1249,7 @@ class BaseAWSLLM:
                         aws_sts_endpoint=aws_sts_endpoint,
                         ssl_verify=ssl_verify,
                         aws_region_name=aws_region_name,
+                        aws_session_tags=aws_session_tags,
                     )
 
                 return self._extract_credentials_and_ttl(sts_response)
@@ -1234,14 +1286,9 @@ class BaseAWSLLM:
                     **sts_client_kwargs,
                 )
 
-        assume_role_params: Final = {
-            "RoleArn": aws_role_name,
-            "RoleSessionName": aws_session_name,
-        }
-
-        # Add ExternalId parameter if provided
-        if aws_external_id is not None:
-            assume_role_params["ExternalId"] = aws_external_id
+        assume_role_params: Final = _assume_role_params(
+            aws_role_name, aws_session_name, aws_external_id, aws_session_tags
+        )
 
         try:
             sts_response = sts_client.assume_role(**assume_role_params)
@@ -1460,6 +1507,7 @@ class BaseAWSLLM:
             "aws_bedrock_runtime_endpoint", None
         )  # https://bedrock-runtime.{region_name}.amazonaws.com
         aws_external_id: Final = optional_params.pop("aws_external_id", None)
+        aws_session_tags: Final = optional_params.pop("aws_session_tags", None)
 
         if bearer_token is not None:
             return BearerRequestTarget(
@@ -1478,6 +1526,7 @@ class BaseAWSLLM:
             aws_web_identity_token=aws_web_identity_token,
             aws_sts_endpoint=aws_sts_endpoint,
             aws_external_id=aws_external_id,
+            aws_session_tags=aws_session_tags,
         )
         return Boto3CredentialsInfo(
             credentials=credentials,
@@ -1623,6 +1672,7 @@ class BaseAWSLLM:
         aws_web_identity_token: Final = optional_params.get("aws_web_identity_token", None)
         aws_sts_endpoint: Final = optional_params.get("aws_sts_endpoint", None)
         aws_external_id: Final = optional_params.get("aws_external_id", None)
+        aws_session_tags: Final = optional_params.get("aws_session_tags", None)
         aws_region_name: Final = self._get_aws_region_name(optional_params=optional_params, model=model)
 
         credentials: Final[Credentials] = self.get_credentials(
@@ -1636,6 +1686,7 @@ class BaseAWSLLM:
             aws_web_identity_token=aws_web_identity_token,
             aws_sts_endpoint=aws_sts_endpoint,
             aws_external_id=aws_external_id,
+            aws_session_tags=aws_session_tags,
         )
 
         sigv4: Final = SigV4Auth(credentials, service_name, aws_region_name)
@@ -1668,3 +1719,52 @@ class BaseAWSLLM:
             request_headers_dict["Authorization"] = incoming_authorization
 
         return request_headers_dict, request.body
+
+
+def sign_aws_json_post(
+    get_credentials: Callable[[], Credentials],
+    service_name: str,
+    aws_region_name: str | None,
+    url: str,
+    body: str,
+    headers: Mapping[str, str],
+) -> AWSPreparedRequest:
+    try:
+        from botocore.auth import SigV4Auth
+        from botocore.awsrequest import AWSRequest
+    except ImportError:
+        raise ImportError(f"Missing boto3 to call {service_name}. Run 'pip install boto3'.")
+
+    aws_request: Final = AWSRequest(method="POST", url=url, data=body, headers=headers)
+    SigV4Auth(get_credentials(), service_name, aws_region_name).add_auth(aws_request)
+    return aws_request.prepare()
+
+
+_SignParams = ParamSpec("_SignParams")
+_SignedRequest = TypeVar("_SignedRequest")
+
+AWS_SIGNING_EXECUTOR: Final = ThreadPoolExecutor(max_workers=AWS_SIGNING_MAX_THREADS, thread_name_prefix="aws-signing")
+
+
+async def run_aws_signing(
+    sign: Callable[_SignParams, _SignedRequest],
+    /,
+    *args: _SignParams.args,
+    **kwargs: _SignParams.kwargs,  # kwargs-ok: ParamSpec forwarding keeps the wrapped signing signature
+) -> _SignedRequest:
+    context: Final = contextvars.copy_context()
+    return await asyncio.get_running_loop().run_in_executor(
+        AWS_SIGNING_EXECUTOR, partial(context.run, sign, *args, **kwargs)
+    )
+
+
+async def sign_request_off_loop_if_aws(
+    provider_config: object,
+    sign_request: Callable[_SignParams, _SignedRequest],
+    /,
+    *args: _SignParams.args,
+    **kwargs: _SignParams.kwargs,  # kwargs-ok: ParamSpec forwarding keeps the wrapped sign_request signature
+) -> _SignedRequest:
+    if isinstance(provider_config, SignsRequestsWithAWS):
+        return await run_aws_signing(sign_request, *args, **kwargs)
+    return sign_request(*args, **kwargs)
diff --git a/litellm/llms/bedrock/batches/handler.py b/litellm/llms/bedrock/batches/handler.py
index 4b500897642..b408d2f620c 100644
--- a/litellm/llms/bedrock/batches/handler.py
+++ b/litellm/llms/bedrock/batches/handler.py
@@ -1,4 +1,4 @@
-from collections.abc import Mapping
+from collections.abc import Mapping, Sequence
 from datetime import datetime
 from typing import TYPE_CHECKING, Any, Final, cast
 
@@ -6,6 +6,7 @@ from openai.types.batch import BatchRequestCounts
 from openai.types.batch import Metadata as OpenAIBatchMetadata
 
 from litellm.litellm_core_utils.aws_partition import get_aws_dns_suffix
+from litellm.types.llms.bedrock import AwsSessionTag
 from litellm.types.utils import LiteLLMBatch
 
 if TYPE_CHECKING:
@@ -116,6 +117,7 @@ class BedrockBatchesHandler:
         aws_web_identity_token: str | None = None,
         aws_sts_endpoint: str | None = None,
         aws_external_id: str | None = None,
+        aws_session_tags: Sequence[AwsSessionTag] | None = None,
         **kwargs: object,  # kwargs-ok: litellm.cancel_batch forwards arbitrary user kwargs verbatim
     ) -> "LiteLLMBatch":
         try:
@@ -139,6 +141,7 @@ class BedrockBatchesHandler:
             aws_web_identity_token=aws_web_identity_token,
             aws_sts_endpoint=aws_sts_endpoint,
             aws_external_id=aws_external_id,
+            aws_session_tags=aws_session_tags,
         )
 
         client: Final = boto3.client(
@@ -163,6 +166,7 @@ class BedrockBatchesHandler:
                 aws_web_identity_token=aws_web_identity_token,
                 aws_sts_endpoint=aws_sts_endpoint,
                 aws_external_id=aws_external_id,
+                aws_session_tags=aws_session_tags,
             )
 
         try:
@@ -283,7 +287,7 @@ class BedrockBatchesHandler:
                 ``aws_session_token``, ``aws_profile_name``,
                 ``aws_role_name``, ``aws_session_name``,
                 ``aws_web_identity_token``, ``aws_sts_endpoint``,
-                ``aws_external_id``). Unknown keys are ignored.
+                ``aws_external_id``, ``aws_session_tags``). Unknown keys are ignored.
 
         Returns:
             ``LiteLLMBatch`` shaped like an OpenAI Batch resource.
@@ -317,6 +321,7 @@ class BedrockBatchesHandler:
             aws_web_identity_token=kwargs.get("aws_web_identity_token"),
             aws_sts_endpoint=kwargs.get("aws_sts_endpoint"),
             aws_external_id=kwargs.get("aws_external_id"),
+            aws_session_tags=kwargs.get("aws_session_tags"),
         )
 
         client: Final = boto3.client(
diff --git a/litellm/llms/bedrock/chat/converse_handler.py b/litellm/llms/bedrock/chat/converse_handler.py
index 984ba371898..d397420cb17 100644
--- a/litellm/llms/bedrock/chat/converse_handler.py
+++ b/litellm/llms/bedrock/chat/converse_handler.py
@@ -21,7 +21,7 @@ from litellm.rust_bridge.chat_completions import rust_chat_completions_accepts
 from litellm.types.utils import ModelResponse
 from litellm.utils import CustomStreamWrapper
 
-from ..base_aws_llm import BaseAWSLLM, Credentials, bedrock_bearer_token
+from ..base_aws_llm import BaseAWSLLM, Credentials, bedrock_bearer_token, run_aws_signing
 from ..common_utils import BedrockError, _get_all_bedrock_regions, error_response_text
 from .invoke_handler import AWSEventStreamDecoder, MockResponseIterator, make_call
 
@@ -136,7 +136,8 @@ class BedrockConverseLLM(BaseAWSLLM):
         )
         data: Final = json.dumps(request_data)
 
-        prepped: Final = self.get_request_headers(
+        prepped: Final = await run_aws_signing(
+            self.get_request_headers,
             credentials=credentials,
             aws_region_name=litellm_params.get("aws_region_name") or "us-west-2",
             extra_headers=headers,
@@ -206,7 +207,8 @@ class BedrockConverseLLM(BaseAWSLLM):
         )
         data: Final = json.dumps(request_data)
 
-        prepped: Final = self.get_request_headers(
+        prepped: Final = await run_aws_signing(
+            self.get_request_headers,
             credentials=credentials,
             aws_region_name=litellm_params.get("aws_region_name") or "us-west-2",
             extra_headers=headers,
@@ -355,6 +357,7 @@ class BedrockConverseLLM(BaseAWSLLM):
         aws_web_identity_token: Final = optional_params.pop("aws_web_identity_token", None)
         aws_sts_endpoint: Final = optional_params.pop("aws_sts_endpoint", None)
         aws_external_id: Final = optional_params.pop("aws_external_id", None)
+        aws_session_tags: Final = optional_params.pop("aws_session_tags", None)
         optional_params.pop("aws_region_name", None)
 
         litellm_params["aws_region_name"] = aws_region_name  # [DO NOT DELETE] important for async calls
@@ -373,6 +376,7 @@ class BedrockConverseLLM(BaseAWSLLM):
                 aws_web_identity_token=aws_web_identity_token,
                 aws_sts_endpoint=aws_sts_endpoint,
                 aws_external_id=aws_external_id,
+                aws_session_tags=aws_session_tags,
             )
         )
 
diff --git a/litellm/llms/bedrock/chat/converse_transformation.py b/litellm/llms/bedrock/chat/converse_transformation.py
index fa24f8be893..fa18361e44c 100644
--- a/litellm/llms/bedrock/chat/converse_transformation.py
+++ b/litellm/llms/bedrock/chat/converse_transformation.py
@@ -4,6 +4,7 @@ Translating between OpenAI's `/chat/completion` format and Amazon's `/converse`
 
 import copy
 import json
+import re
 import time
 import types
 from collections.abc import Mapping
@@ -293,6 +294,10 @@ class AmazonConverseConfig(BaseConfig):
                     llm_provider="bedrock",
                 )
 
+    @staticmethod
+    def _is_openai_gpt_reasoning_model(model: str) -> bool:
+        return re.search(r"openai\.gpt-\d", model) is not None
+
     def _is_nova_2_model(self, model: str) -> bool:
         """
         Check if the model is a Nova 2 model that supports reasoningConfig.
@@ -422,15 +427,15 @@ class AmazonConverseConfig(BaseConfig):
         """
         Handle the reasoning_effort parameter based on the model type.
 
-        - GPT-OSS models: passed through unchanged via additionalModelRequestFields.
-        - OpenAI GPT-5.x models: mapped to ``reasoning.effort`` via additionalModelRequestFields.
+        - GPT-OSS and DeepSeek V3 models: passed through unchanged via additionalModelRequestFields.
+        - OpenAI GPT-5.x and GPT-6 models: mapped to ``reasoning.effort`` via additionalModelRequestFields.
         - Nova 2 models: transformed to reasoningConfig.
         - Anthropic models: mapped to ``thinking`` (and ``output_config.effort`` on
           adaptive Claude 4.6 / 4.7).
         """
-        if "gpt-oss" in model:
+        if "gpt-oss" in model or "deepseek" in model:
             optional_params["reasoning_effort"] = reasoning_effort
-        elif "openai.gpt-5" in model:
+        elif self._is_openai_gpt_reasoning_model(model):
             reasoning: Final[BedrockConverseGptReasoningEffortBlock] = {"effort": reasoning_effort}
             optional_params["reasoning"] = reasoning
         elif self._is_nova_2_model(model):
@@ -509,6 +514,36 @@ class AmazonConverseConfig(BaseConfig):
                 )
                 thinking["budget_tokens"] = BEDROCK_MIN_THINKING_BUDGET_TOKENS
 
+    def _is_deepseek_model(self, model: str, base_model: str) -> bool:
+        return "deepseek" in model or "deepseek" in base_model
+
+    def _is_deepseek_r1_model(self, model: str, base_model: str) -> bool:
+        return "deepseek.r1" in model or "deepseek.r1" in base_model
+
+    def _model_accepts_anthropic_thinking_param(self, model: str, base_model: str) -> bool:
+        """Whether the model accepts the Anthropic-shaped ``thinking`` request field.
+
+        Only Claude reasoning models accept it. DeepSeek advertises ``supports_reasoning`` but reasons
+        natively: R1 returns a 400 when the field is sent and V3 silently ignores it.
+        """
+        if self._is_deepseek_model(model=model, base_model=base_model):
+            return False
+        return (
+            "claude-3-7" in model
+            or "claude-sonnet-4" in model
+            or "claude-opus-4" in model
+            or supports_reasoning(model=model, custom_llm_provider=self.custom_llm_provider)
+            or supports_reasoning(model=base_model, custom_llm_provider=self.custom_llm_provider)
+        )
+
+    def _model_rejects_reasoning_effort_param(self, model: str, base_model: str) -> bool:
+        """Whether the model returns a 400 for every ``reasoning_effort`` shape on Converse.
+
+        DeepSeek R1 always reasons and rejects any reasoning request field. DeepSeek V3 accepts a raw
+        ``reasoning_effort`` like gpt-oss does, and every other model maps it to a shape it accepts.
+        """
+        return self._is_deepseek_r1_model(model=model, base_model=base_model)
+
     def get_supported_openai_params(self, model: str) -> list[str]:
         from litellm.utils import supports_function_calling
 
@@ -564,23 +599,20 @@ class AmazonConverseConfig(BaseConfig):
             # only anthropic and mistral support tool choice config. otherwise (E.g. cohere) will fail the call - https://docs.aws.amazon.com/bedrock/latest/APIReference/API_runtime_ToolChoice.html
             supported_params.append("tool_choice")
 
-        if "gpt-oss" in model or "openai.gpt-5" in model or "openai.gpt-5" in base_model:
+        if (
+            "gpt-oss" in model
+            or self._is_openai_gpt_reasoning_model(model)
+            or self._is_openai_gpt_reasoning_model(base_model)
+        ):
             supported_params.append("reasoning_effort")
+        elif self._is_deepseek_model(model=model, base_model=base_model):
+            if not self._is_deepseek_r1_model(model=model, base_model=base_model):
+                supported_params.append("reasoning_effort")
         elif self._is_nova_2_model(model):
             # Nova 2 models support reasoning_effort (transformed to reasoningConfig)
             # These models use a different reasoning structure than Anthropic's thinking parameter
             supported_params.append("reasoning_effort")
-        elif (
-            "claude-3-7" in model
-            or "claude-sonnet-4" in model
-            or "claude-opus-4" in model
-            or "deepseek.r1" in model
-            or supports_reasoning(
-                model=model,
-                custom_llm_provider=self.custom_llm_provider,
-            )
-            or supports_reasoning(model=base_model, custom_llm_provider=self.custom_llm_provider)
-        ):
+        elif self._model_accepts_anthropic_thinking_param(model=model, base_model=base_model):
             supported_params.append("thinking")
             supported_params.append("reasoning_effort")
             supported_params.append("output_config")
@@ -872,6 +904,11 @@ class AmazonConverseConfig(BaseConfig):
         drop_params: bool,
     ) -> dict:
         is_thinking_enabled: Final = self.is_thinking_enabled(non_default_params)
+        base_model: Final = BedrockModelInfo.get_base_model(model)
+        drop_thinking_param: Final = self._is_deepseek_model(model=model, base_model=base_model)
+        drop_reasoning_effort_param: Final = self._model_rejects_reasoning_effort_param(
+            model=model, base_model=base_model
+        )
 
         for param, value in non_default_params.items():
             if param == "response_format" and isinstance(value, dict):
@@ -920,7 +957,12 @@ class AmazonConverseConfig(BaseConfig):
                 optional_params["_parallel_tool_use_config"] = {
                     "tool_choice": {"type": "auto", "disable_parallel_tool_use": not value}
                 }
-            if param == "thinking" and "openai.gpt-5" not in model:
+            if param == "thinking" and drop_thinking_param:
+                verbose_logger.debug(
+                    "Dropping unsupported `thinking` param for Bedrock model=%s; it reasons natively.",
+                    model,
+                )
+            elif param == "thinking" and not self._is_openai_gpt_reasoning_model(model):
                 if (
                     isinstance(value, dict)
                     and value.get("type") == "adaptive"
@@ -946,6 +988,11 @@ class AmazonConverseConfig(BaseConfig):
                     AnthropicModelInfo.translate_legacy_thinking_for_adaptive_model(
                         model=model, optional_params=optional_params, custom_llm_provider="bedrock"
                     )
+            elif param == "reasoning_effort" and isinstance(value, str) and drop_reasoning_effort_param:
+                verbose_logger.debug(
+                    "Dropping unsupported `reasoning_effort` param for Bedrock model=%s; it always reasons and rejects it.",
+                    model,
+                )
             elif param == "reasoning_effort" and isinstance(value, str):
                 self._handle_reasoning_effort_parameter(
                     model=model, reasoning_effort=value, optional_params=optional_params
@@ -1805,6 +1852,7 @@ class AmazonConverseConfig(BaseConfig):
             data=request_data,
             messages=messages,
             encoding=encoding,
+            json_mode=json_mode,
         )
 
     def _transform_reasoning_content(self, reasoning_content_blocks: list[BedrockConverseReasoningContentBlock]) -> str:
@@ -2237,6 +2285,7 @@ class AmazonConverseConfig(BaseConfig):
         data: dict | str,
         messages: list,
         encoding,
+        json_mode: bool | None = None,
     ) -> ModelResponse:
         ## LOGGING
         if logging_obj is not None:
@@ -2247,7 +2296,9 @@ class AmazonConverseConfig(BaseConfig):
                 additional_args={"complete_input_dict": data},
             )
 
-        json_mode: Final[bool | None] = optional_params.get("json_mode", None)
+        resolved_json_mode: Final[bool | None] = (
+            json_mode if json_mode is not None else optional_params.get("json_mode", None)
+        )
         ## RESPONSE OBJECT
         try:
             completion_response: Final = ConverseResponseBlock(**response.json())
@@ -2339,7 +2390,7 @@ class AmazonConverseConfig(BaseConfig):
             chat_completion_message["thinking_blocks"] = self._transform_thinking_blocks(reasoningContentBlocks)
         chat_completion_message["content"] = content_str
         filtered_tools: Final = self._filter_json_mode_tools(
-            json_mode=json_mode,
+            json_mode=resolved_json_mode,
             tools=tools,
             chat_completion_message=chat_completion_message,
         )
@@ -2363,7 +2414,7 @@ class AmazonConverseConfig(BaseConfig):
         # When json_mode filtered out all synthetic tool calls the response
         # is plain content, not a pending tool invocation. Fix finish_reason
         # so callers (e.g. OpenAI SDK) don't misinterpret it.
-        if json_mode and not filtered_tools and tools:
+        if resolved_json_mode and not filtered_tools and tools:
             initial_finish_reason = "stop"
 
         (
diff --git a/litellm/llms/bedrock/chat/invoke_transformations/base_invoke_transformation.py b/litellm/llms/bedrock/chat/invoke_transformations/base_invoke_transformation.py
index a0e32c8aa22..90a2692f68a 100644
--- a/litellm/llms/bedrock/chat/invoke_transformations/base_invoke_transformation.py
+++ b/litellm/llms/bedrock/chat/invoke_transformations/base_invoke_transformation.py
@@ -340,6 +340,7 @@ class AmazonInvokeConfig(BaseConfig, BaseAWSLLM):
                     optional_params=optional_params,
                     litellm_params=litellm_params,
                     encoding=encoding,
+                    json_mode=json_mode,
                 )
             elif provider == "twelvelabs":
                 return litellm.AmazonTwelveLabsPegasusConfig().transform_response(
diff --git a/litellm/llms/bedrock/common_utils.py b/litellm/llms/bedrock/common_utils.py
index be4f0f32689..cb2c70e74c8 100644
--- a/litellm/llms/bedrock/common_utils.py
+++ b/litellm/llms/bedrock/common_utils.py
@@ -93,6 +93,7 @@ _BEDROCK_AWS_AUTH_PARAMETER_KEYS: Final[tuple[str, ...]] = (
     "aws_web_identity_token",
     "aws_sts_endpoint",
     "aws_external_id",
+    "aws_session_tags",
 )
 
 
@@ -1663,6 +1664,7 @@ class CommonBatchFilesUtils:
             aws_web_identity_token=optional_params.get("aws_web_identity_token"),
             aws_sts_endpoint=optional_params.get("aws_sts_endpoint"),
             aws_external_id=optional_params.get("aws_external_id"),
+            aws_session_tags=optional_params.get("aws_session_tags"),
         )
 
         # Prepare the request data
diff --git a/litellm/llms/bedrock/count_tokens/handler.py b/litellm/llms/bedrock/count_tokens/handler.py
index 1fb53f6ff0a..d7fb510f057 100644
--- a/litellm/llms/bedrock/count_tokens/handler.py
+++ b/litellm/llms/bedrock/count_tokens/handler.py
@@ -10,9 +10,10 @@ import httpx
 
 import litellm
 from litellm._logging import verbose_logger
+from litellm.llms.bedrock.base_aws_llm import run_aws_signing
 from litellm.llms.bedrock.common_utils import BedrockError
 from litellm.llms.bedrock.count_tokens.transformation import BedrockCountTokensConfig
-from litellm.llms.custom_httpx.http_handler import get_async_httpx_client
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, get_async_httpx_client
 
 
 class BedrockCountTokensHandler(BedrockCountTokensConfig):
@@ -27,6 +28,7 @@ class BedrockCountTokensHandler(BedrockCountTokensConfig):
         request_data: dict[str, Any],
         litellm_params: dict[str, Any],
         resolved_model: str,
+        client: AsyncHTTPHandler | None = None,
     ) -> dict[str, Any]:
         """
         Handle a CountTokens request using existing LiteLLM patterns.
@@ -75,7 +77,8 @@ class BedrockCountTokensHandler(BedrockCountTokensConfig):
             # Extract api_key for bearer token auth if provided
             api_key: Final = litellm_params.get("api_key", None)
             headers: Final = {"Content-Type": "application/json"}
-            signed_headers, signed_body = self._sign_request(
+            signed_headers, signed_body = await run_aws_signing(
+                self._sign_request,
                 service_name="bedrock",
                 headers=headers,
                 optional_params=litellm_params,
@@ -85,7 +88,7 @@ class BedrockCountTokensHandler(BedrockCountTokensConfig):
                 api_key=api_key,
             )
 
-            async_client: Final = get_async_httpx_client(llm_provider=litellm.LlmProviders.BEDROCK)
+            async_client: Final = client or get_async_httpx_client(llm_provider=litellm.LlmProviders.BEDROCK)
 
             response: Final = await async_client.post(
                 endpoint_url,
diff --git a/litellm/llms/bedrock/embed/embedding.py b/litellm/llms/bedrock/embed/embedding.py
index e249feb9ff3..7efdfd3cebb 100644
--- a/litellm/llms/bedrock/embed/embedding.py
+++ b/litellm/llms/bedrock/embed/embedding.py
@@ -5,7 +5,7 @@ Handles embedding calls to Bedrock's `/invoke` endpoint
 import copy
 import json
 import urllib.parse
-from collections.abc import Callable
+from collections.abc import Callable, Mapping
 from typing import TYPE_CHECKING, Final, get_args, overload
 
 import httpx
@@ -26,7 +26,7 @@ from litellm.types.llms.bedrock import (
 )
 from litellm.types.utils import EmbeddingResponse, LlmProviders
 
-from ..base_aws_llm import BaseAWSLLM, Credentials, bedrock_bearer_token
+from ..base_aws_llm import AWSPreparedRequest, BaseAWSLLM, Credentials, bedrock_bearer_token, run_aws_signing
 from ..common_utils import BedrockError
 from .amazon_nova_transformation import AmazonNovaEmbeddingConfig
 from .amazon_titan_g1_transformation import AmazonTitanG1Config
@@ -41,6 +41,20 @@ if TYPE_CHECKING:
     from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
 
 
+def _sign_get_request(
+    credentials: Credentials, url: str, headers: Mapping[str, str], aws_region_name: str
+) -> AWSPreparedRequest:
+    try:
+        from botocore.auth import SigV4Auth
+        from botocore.awsrequest import AWSRequest
+    except ImportError:
+        raise ImportError("Missing boto3 to call bedrock. Run 'pip install boto3'.")
+
+    request: Final = AWSRequest(method="GET", url=url, data=None, headers=headers)
+    SigV4Auth(credentials, "bedrock", aws_region_name).add_auth(request)
+    return request.prepare()
+
+
 class BedrockEmbedding(BaseAWSLLM):
     @overload
     def _load_credentials(
@@ -73,6 +87,7 @@ class BedrockEmbedding(BaseAWSLLM):
         aws_web_identity_token: Final = optional_params.pop("aws_web_identity_token", None)
         aws_sts_endpoint: Final = optional_params.pop("aws_sts_endpoint", None)
         aws_external_id: Final = optional_params.pop("aws_external_id", None)
+        aws_session_tags: Final = optional_params.pop("aws_session_tags", None)
 
         ### SET REGION NAME ###
         if aws_region_name is None:
@@ -103,6 +118,7 @@ class BedrockEmbedding(BaseAWSLLM):
                 aws_web_identity_token=aws_web_identity_token,
                 aws_sts_endpoint=aws_sts_endpoint,
                 aws_external_id=aws_external_id,
+                aws_session_tags=aws_session_tags,
             )
         )
         return credentials, aws_region_name
@@ -342,7 +358,8 @@ class BedrockEmbedding(BaseAWSLLM):
             if extra_headers is not None:
                 headers = {"Content-Type": "application/json", **extra_headers}
 
-            prepped = self.get_request_headers(
+            prepped = await run_aws_signing(
+                self.get_request_headers,
                 credentials=credentials,
                 aws_region_name=aws_region_name,
                 extra_headers=extra_headers,
@@ -600,9 +617,6 @@ class BedrockEmbedding(BaseAWSLLM):
             dict: Status response from AWS Bedrock
         """
 
-        # Get AWS credentials using the same method as other Bedrock methods
-        credentials, _ = self._load_credentials(kwargs)
-
         # Get the runtime endpoint
         endpoint_url, _ = self.get_runtime_endpoint(
             api_base=None,
@@ -619,27 +633,13 @@ class BedrockEmbedding(BaseAWSLLM):
         # Prepare headers for GET request
         headers: Final = {"Content-Type": "application/json"}
 
-        # Use AWSRequest directly for GET requests (get_request_headers hardcodes POST)
-        try:
-            from botocore.auth import SigV4Auth
-            from botocore.awsrequest import AWSRequest
-        except ImportError:
-            raise ImportError("Missing boto3 to call bedrock. Run 'pip install boto3'.")
+        def sign_status_request() -> AWSPreparedRequest:
+            credentials, _ = self._load_credentials(kwargs)
+            return _sign_get_request(
+                credentials=credentials, url=status_url, headers=headers, aws_region_name=aws_region_name
+            )
 
-        # Create AWSRequest with GET method and encoded URL
-        request: Final = AWSRequest(
-            method="GET",
-            url=status_url,
-            data=None,  # GET request, no body
-            headers=headers,
-        )
-
-        # Sign the request - SigV4Auth will create canonical string from request URL
-        sigv4: Final = SigV4Auth(credentials, "bedrock", aws_region_name)
-        sigv4.add_auth(request)
-
-        # Prepare the request
-        prepped: Final = request.prepare()
+        prepped: Final = await run_aws_signing(sign_status_request)
 
         # LOGGING
         if logging_obj is not None:
diff --git a/litellm/llms/bedrock/files/transformation.py b/litellm/llms/bedrock/files/transformation.py
index 33b27943ad8..9875ac2b9c3 100644
--- a/litellm/llms/bedrock/files/transformation.py
+++ b/litellm/llms/bedrock/files/transformation.py
@@ -7,13 +7,13 @@ from contextlib import suppress
 from functools import cache
 from itertools import chain
 from types import MappingProxyType
-from typing import Any, Final, TypeAlias, TypedDict
+from typing import Any, Final, Literal, TypeAlias, TypedDict
 from urllib.parse import unquote
 
 import httpx
 from httpx import Headers, Response
 from openai.types.file_deleted import FileDeleted
-from pydantic import BaseModel, ConfigDict, TypeAdapter
+from pydantic import BaseModel, ConfigDict, Field, TypeAdapter
 from typing_extensions import ReadOnly
 
 from litellm._logging import verbose_logger
@@ -60,11 +60,12 @@ from litellm.utils import get_llm_provider
 from ..base_aws_llm import BaseAWSLLM
 from ..common_utils import BedrockError, merge_bedrock_aws_request_params, resolve_s3_encryption_key_id
 
-# litellm_params key used to hand the SigV4-signed GET headers from
-# `transform_file_content_request` to `validate_environment` (the only hook
-# the shared file-content HTTP handler exposes for setting request headers).
-# Same pattern as the `upload_url` handoff in `transform_create_file_request`.
-S3_SIGNED_GET_HEADERS_PARAM: Final = "_s3_signed_get_headers"
+S3_SIGNED_REQUEST_HEADERS_PARAM: Final = "_s3_signed_request_headers"
+
+
+class _S3DeleteContext(BaseModel):
+    file_id: str = Field(min_length=1)
+
 
 # litellm_params key carrying the size of the body uploaded to S3, handed from
 # `transform_create_file_request` to `transform_create_file_response`.
@@ -291,7 +292,7 @@ class BedrockFilesConfig(BaseAWSLLM, BaseFilesConfig):
     ) -> dict:
         result: Final[dict[str, object]] = {}
         result.update(headers)
-        signed_headers: Final = litellm_params.pop(S3_SIGNED_GET_HEADERS_PARAM, None)
+        signed_headers: Final = litellm_params.pop(S3_SIGNED_REQUEST_HEADERS_PARAM, None)
         if isinstance(signed_headers, Mapping):
             result.update(signed_headers)  # any-ok: untyped handoff headers
         # otherwise no extra headers - AWS credentials are handled by BaseAWSLLM
@@ -1187,18 +1188,27 @@ class BedrockFilesConfig(BaseAWSLLM, BaseFilesConfig):
     def transform_delete_file_request(
         self,
         file_id: str,
-        optional_params: dict,
-        litellm_params: dict,
-    ) -> tuple[str, dict]:
-        raise NotImplementedError("BedrockFilesConfig does not support file deletion")
+        optional_params: Mapping[str, object],
+        litellm_params: MutableMapping[str, object],
+    ) -> tuple[str, dict[str, str]]:
+        return self._transform_s3_file_request(
+            file_id=file_id, method="DELETE", optional_params=optional_params, litellm_params=litellm_params
+        )
 
     def transform_delete_file_response(
         self,
         raw_response: httpx.Response,
         logging_obj: LiteLLMLoggingObj,
-        litellm_params: dict,
+        litellm_params: Mapping[str, object],
     ) -> FileDeleted:
-        raise NotImplementedError("BedrockFilesConfig does not support file deletion")
+        if raw_response.status_code != 204:
+            raise BedrockError(
+                status_code=raw_response.status_code if raw_response.status_code >= 400 else 502,
+                message=raw_response.text or f"S3 file deletion returned HTTP {raw_response.status_code}",
+                headers=raw_response.headers,
+            )
+        context: Final = _S3DeleteContext.model_validate(logging_obj.model_call_details.get("additional_args"))
+        return FileDeleted(id=context.file_id, deleted=True, object="file")
 
     def transform_list_files_request(
         self,
@@ -1233,6 +1243,18 @@ class BedrockFilesConfig(BaseAWSLLM, BaseFilesConfig):
         if not file_id:
             raise ValueError("file_id is required for Bedrock file content retrieval")
 
+        return self._transform_s3_file_request(
+            file_id=file_id, method="GET", optional_params=optional_params, litellm_params=litellm_params
+        )
+
+    def _transform_s3_file_request(
+        self,
+        *,
+        file_id: str,
+        method: Literal["GET", "DELETE"],
+        optional_params: Mapping[str, object],
+        litellm_params: MutableMapping[str, object],
+    ) -> tuple[str, dict[str, str]]:
         s3_uri: Final = extract_s3_uri_from_file_id(file_id)
         bucket_name, object_key = _validate_file_id_against_configured_buckets(
             s3_uri=s3_uri,
@@ -1240,40 +1262,32 @@ class BedrockFilesConfig(BaseAWSLLM, BaseFilesConfig):
             allow_legacy_cloud_file_ids=should_allow_legacy_cloud_file_ids(litellm_params),
         )
 
-        # The shared file-content handler passes optional_params={}, so AWS
-        # credentials/region arrive via litellm_params here (unlike the upload
-        # path). s3_region_name wins over aws_region_name, same priority as
-        # get_complete_file_url above.
-        merged_params: Final[dict[str, object]] = {}
-        merged_params.update(litellm_params)
-        merged_params.update(optional_params)
-        request_params: Final = _BedrockS3RequestParams.model_validate(merged_params)
+        request_params: Final = _BedrockS3RequestParams.model_validate({**litellm_params, **optional_params})
 
         region_preference: Final = request_params.s3_region_name or request_params.aws_region_name
         region_params: Final[dict[str, str | None]] = {"aws_region_name": region_preference}
         aws_region_name: Final = self._get_aws_region_name(optional_params=region_params, model="")
 
-        s3_endpoint_url = (
+        s3_endpoint_url: Final = (
             request_params.s3_endpoint_url or f"https://s3.{aws_region_name}.{get_aws_dns_suffix(aws_region_name)}"
         ).rstrip("/")
         url: Final = f"{s3_endpoint_url}/{bucket_name}/{encode_s3_object_key_for_url(object_key)}"
 
-        litellm_params[S3_SIGNED_GET_HEADERS_PARAM] = self._sign_s3_get_request(
+        litellm_params[S3_SIGNED_REQUEST_HEADERS_PARAM] = self._sign_s3_request_without_body(
             api_base=url,
             aws_region_name=aws_region_name,
             request_params=request_params,
+            method=method,
         )
         return url, {}
 
-    def _sign_s3_get_request(
+    def _sign_s3_request_without_body(
         self,
         api_base: str,
         aws_region_name: str,
         request_params: _BedrockS3RequestParams,
+        method: Literal["GET", "DELETE"] = "GET",
     ) -> dict[str, str]:
-        """
-        SigV4-sign an S3 GetObject request, mirroring `_sign_s3_request` (PUT).
-        """
         try:
             import hashlib
 
@@ -1297,7 +1311,7 @@ class BedrockFilesConfig(BaseAWSLLM, BaseFilesConfig):
 
         empty_body_hash: Final = hashlib.sha256(b"").hexdigest()
         aws_request: Final = AWSRequest(  # any-ok: botocore AWSRequest is untyped
-            method="GET",
+            method=method,
             url=api_base,
             headers={"x-amz-content-sha256": empty_body_hash},
         )
diff --git a/litellm/llms/bedrock/realtime/handler.py b/litellm/llms/bedrock/realtime/handler.py
index 42fe8941443..ca2370303f2 100644
--- a/litellm/llms/bedrock/realtime/handler.py
+++ b/litellm/llms/bedrock/realtime/handler.py
@@ -21,7 +21,7 @@ from litellm.litellm_core_utils.realtime_streaming import DefaultLoggedRealTimeE
 from litellm.types.llms.openai import OpenAIRealtimeEvents
 from litellm.types.realtime import RealtimeResponseTransformInput
 
-from ..base_aws_llm import BaseAWSLLM
+from ..base_aws_llm import BaseAWSLLM, run_aws_signing
 from ..common_utils import BedrockError
 from .transformation import BedrockRealtimeConfig
 
@@ -149,7 +149,8 @@ class BedrockRealtime(BaseAWSLLM):
 
         verbose_proxy_logger.debug("Bedrock Realtime: Connecting to %s with model %s", endpoint_uri, model)
 
-        credentials: Final = self.get_credentials(
+        credentials: Final = await run_aws_signing(
+            self.get_credentials,
             aws_access_key_id=aws_access_key_id,
             aws_secret_access_key=aws_secret_access_key,
             aws_session_token=aws_session_token,
@@ -169,7 +170,7 @@ class BedrockRealtime(BaseAWSLLM):
                     "or configure credentials in the environment"
                 ),
             )
-        frozen_credentials: Final = credentials.get_frozen_credentials()
+        frozen_credentials: Final = await run_aws_signing(credentials.get_frozen_credentials)
 
         # Initialize Bedrock client with aws_sdk_bedrock_runtime
         config: Final = Config(
diff --git a/litellm/llms/bedrock_mantle/common_utils.py b/litellm/llms/bedrock_mantle/common_utils.py
index 850738bc320..ac94d9cb922 100644
--- a/litellm/llms/bedrock_mantle/common_utils.py
+++ b/litellm/llms/bedrock_mantle/common_utils.py
@@ -23,7 +23,7 @@ from botocore.exceptions import (
     ProfileNotFound,
 )
 
-from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM
+from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM, SignsRequestsWithAWS
 from litellm.secret_managers.main import get_secret_str
 
 BEDROCK_MANTLE_DEFAULT_REGION: Final = "us-east-1"
@@ -55,7 +55,7 @@ def resolve_mantle_region(params: Mapping[str, object]) -> str:
     )
 
 
-class BedrockMantleAuthMixin:
+class BedrockMantleAuthMixin(SignsRequestsWithAWS):
     _aws_signer: BaseAWSLLM
 
     @staticmethod
diff --git a/litellm/llms/custom_httpx/http_handler.py b/litellm/llms/custom_httpx/http_handler.py
index e1f0fc9e7d3..f4883b57fbc 100644
--- a/litellm/llms/custom_httpx/http_handler.py
+++ b/litellm/llms/custom_httpx/http_handler.py
@@ -9,6 +9,7 @@ import threading
 import time
 from collections.abc import AsyncIterable, Callable, Iterable, Mapping
 from http.cookiejar import CookieJar, DefaultCookiePolicy
+from io import BytesIO
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, ClassVar, Final, NoReturn, Optional, TypeAlias, TypedDict, TypeVar
 
@@ -505,6 +506,10 @@ async def _raise_masked_async_error(e: httpx.HTTPStatusError, stream: bool) -> N
     raise MaskedHTTPStatusError(e, message=_text, text=_text) from None
 
 
+class HTTPResponseLimitError(ValueError):
+    pass
+
+
 class MaskedHTTPStatusError(httpx.HTTPStatusError):
     def __init__(self, original_error, message: str | None = None, text: str | None = None):
         # Create a new error with the masked URL
@@ -654,6 +659,7 @@ class AsyncHTTPHandler:
         headers: dict | None = None,
         follow_redirects: bool | None = None,
         timeout: float | httpx.Timeout | None = None,
+        max_response_bytes: int | None = None,
     ):
         # Set follow_redirects to UseClientDefault if None
         _follow_redirects: Final = follow_redirects if follow_redirects is not None else USE_CLIENT_DEFAULT
@@ -661,6 +667,16 @@ class AsyncHTTPHandler:
         params = params or {}
         params.update(HTTPHandler.extract_query_params(url))
 
+        if max_response_bytes is not None:
+            return await self._get_with_response_limit(
+                url,
+                params=httpx.QueryParams(params),
+                headers=httpx.Headers(headers),
+                max_bytes=max_response_bytes,
+                follow_redirects=self.client.follow_redirects if follow_redirects is None else follow_redirects,
+                timeout=self.client.timeout if timeout is None else httpx.Timeout(timeout),
+            )
+
         response: Final = await self.client.get(
             url,
             params=params,
@@ -670,6 +686,57 @@ class AsyncHTTPHandler:
         )
         return response
 
+    async def _get_with_response_limit(
+        self,
+        url: str,
+        *,
+        params: httpx.QueryParams,
+        headers: httpx.Headers,
+        timeout: httpx.Timeout,
+        max_bytes: int,
+        follow_redirects: bool,
+    ) -> httpx.Response:
+        request: Final = self.client.build_request(
+            "GET",
+            url,
+            headers=MappingProxyType({**headers, "accept-encoding": "identity"}),
+            params=params,
+            timeout=timeout,
+        )
+        response: Final = await self.client.send(request, stream=True, follow_redirects=False)
+        return await self._read_with_response_limit(response, max_bytes=max_bytes, follow_redirects=follow_redirects)
+
+    async def _read_with_response_limit(
+        self, response: httpx.Response, *, max_bytes: int, follow_redirects: bool, redirects_remaining: int = 10
+    ) -> httpx.Response:
+        try:
+            if response.next_request is not None and follow_redirects:
+                if redirects_remaining == 0:
+                    raise ValueError("Too many redirects")
+                await response.aclose()
+                following: Final = await self.client.send(
+                    response.next_request, auth=None, stream=True, follow_redirects=False
+                )
+                return await self._read_with_response_limit(
+                    following, max_bytes=max_bytes, follow_redirects=True, redirects_remaining=redirects_remaining - 1
+                )
+            if response.is_redirect or response.is_error:
+                return httpx.Response(response.status_code, headers=response.headers, request=response.request)
+            if response.headers.get("content-encoding", "identity").lower() != "identity":
+                raise HTTPResponseLimitError("Response size limits require an uncompressed response")
+            if int(response.headers.get("content-length", "0")) > max_bytes:
+                raise HTTPResponseLimitError("Response exceeds the configured size limit")
+            with BytesIO() as body:
+                async for chunk in response.aiter_bytes(chunk_size=65536):
+                    if body.tell() + len(chunk) > max_bytes:
+                        raise HTTPResponseLimitError("Response exceeds the configured size limit")
+                    body.write(chunk)
+                return httpx.Response(
+                    response.status_code, headers=response.headers, content=body.getvalue(), request=response.request
+                )
+        finally:
+            await response.aclose()
+
     @track_llm_api_timing()
     async def post(
         self,
@@ -751,7 +818,9 @@ class AsyncHTTPHandler:
         timeout: float | httpx.Timeout | None = None,
         stream: bool = False,
         content: _RequestContent | None = None,
+        follow_redirects: bool | None = None,
     ):
+        _follow_redirects: Final = follow_redirects if follow_redirects is not None else USE_CLIENT_DEFAULT
         try:
             if timeout is None:
                 timeout = self.timeout
@@ -769,22 +838,30 @@ class AsyncHTTPHandler:
                 timeout=timeout,
                 content=request_content,
             )
-            response: Final = await self.client.send(req)
+            response: Final = await self.client.send(req, follow_redirects=_follow_redirects)
             response.raise_for_status()
             return response
         except (httpx.RemoteProtocolError, httpx.ConnectError):
             # Retry the request with a new session if there is a connection error
             new_client: Final = self.create_client(timeout=timeout, event_hooks=self.event_hooks)
             try:
-                return await self.single_connection_post_request(
-                    url=url,
-                    client=new_client,
-                    data=data,
+                retry_data, retry_content = _prepare_request_data_and_content(data, content)
+                retry: Final = new_client.build_request(
+                    "PUT",
+                    url,
+                    data=retry_data,
                     json=json,
                     params=params,
                     headers=headers,
-                    stream=stream,
+                    timeout=timeout,
+                    content=retry_content,
                 )
+                retried: Final = await new_client.send(retry, stream=stream, follow_redirects=_follow_redirects)
+                try:
+                    retried.raise_for_status()
+                except httpx.HTTPStatusError as retried_error:
+                    await _raise_masked_async_error(retried_error, stream)
+                return retried
             finally:
                 await new_client.aclose()
         except httpx.TimeoutException as e:
diff --git a/litellm/llms/custom_httpx/llm_http_handler.py b/litellm/llms/custom_httpx/llm_http_handler.py
index 7587b963a38..e720428847d 100644
--- a/litellm/llms/custom_httpx/llm_http_handler.py
+++ b/litellm/llms/custom_httpx/llm_http_handler.py
@@ -77,6 +77,7 @@ from litellm.llms.base_llm.vector_store_files.transformation import (
     BaseVectorStoreFilesConfig,
 )
 from litellm.llms.base_llm.videos.transformation import BaseVideoConfig
+from litellm.llms.bedrock.base_aws_llm import SignsRequestsWithAWS, run_aws_signing, sign_request_off_loop_if_aws
 from litellm.llms.custom_httpx.container_handler import raise_for_error_status
 from litellm.llms.custom_httpx.http_handler import (
     AsyncHTTPHandler,
@@ -579,7 +580,7 @@ class BaseLLMHTTPHandler:
             data: dict[str, object],  # mutable-ok: async_completion takes dict
             signed_headers: dict[str, object],  # mutable-ok: async_completion takes dict
             signed_json_body: bytes | None,
-        ):
+        ) -> Coroutine[object, object, ModelResponse | CustomStreamWrapper]:
             async_client: Final = client if isinstance(client, AsyncHTTPHandler) else None
             if stream is True:
                 return self.acompletion_stream_function(
@@ -626,7 +627,7 @@ class BaseLLMHTTPHandler:
 
         if acompletion is True and provider_config.uses_async_transform_request:
 
-            async def transform_then_dispatch():
+            async def transform_then_dispatch() -> ModelResponse | CustomStreamWrapper:
                 transformed: Final = cast(  # cast-ok: async_transform_request is declared as a bare dict
                     "dict[str, object]",
                     await provider_config.async_transform_request(
@@ -637,7 +638,12 @@ class BaseLLMHTTPHandler:
                         headers=request_headers,
                     ),
                 )
-                return await dispatch_async(*await asyncio.to_thread(sign_and_log, transformed))
+                signed_request: Final = await (
+                    run_aws_signing(sign_and_log, transformed)
+                    if isinstance(provider_config, SignsRequestsWithAWS)
+                    else asyncio.to_thread(sign_and_log, transformed)
+                )
+                return await dispatch_async(*signed_request)
 
             return transform_then_dispatch()
 
@@ -1973,7 +1979,9 @@ class BaseLLMHTTPHandler:
             api_key=api_key,
         )
 
-        signed_headers, signed_json_body = provider_config.sign_request(
+        signed_headers, signed_json_body = await sign_request_off_loop_if_aws(
+            provider_config,
+            provider_config.sign_request,
             headers=headers,
             optional_params=optional_params,
             request_data=data,
@@ -2074,7 +2082,9 @@ class BaseLLMHTTPHandler:
                         max_attempts,
                     )
                     provider_config.transform_anthropic_messages_request_on_http_error(e=e, request_data=request_body)
-                    headers, signed_json_body = provider_config.sign_request(
+                    headers, signed_json_body = await sign_request_off_loop_if_aws(
+                        provider_config,
+                        provider_config.sign_request,
                         headers=headers,
                         optional_params=optional_params_dict,
                         request_data=request_body,
@@ -2234,7 +2244,9 @@ class BaseLLMHTTPHandler:
             stream=stream,
         )
 
-        headers, signed_json_body = anthropic_messages_provider_config.sign_request(
+        headers, signed_json_body = await sign_request_off_loop_if_aws(
+            anthropic_messages_provider_config,
+            anthropic_messages_provider_config.sign_request,
             headers=headers,
             optional_params=dict(litellm_params),  # dynamic aws_* params are passed under litellm_params
             request_data=request_body,
@@ -2910,7 +2922,9 @@ class BaseLLMHTTPHandler:
                 fake_stream=fake_stream,
             )
 
-        headers, signed_body = responses_api_provider_config.sign_request(
+        headers, signed_body = await sign_request_off_loop_if_aws(
+            responses_api_provider_config,
+            responses_api_provider_config.sign_request,
             headers=headers,
             optional_params=dict(litellm_params),
             request_data=data,
@@ -4618,7 +4632,9 @@ class BaseLLMHTTPHandler:
         )
         data = BaseResponsesAPIConfig.normalize_responses_api_request_dict(data)
 
-        headers, signed_body = responses_api_provider_config.sign_request(
+        headers, signed_body = await sign_request_off_loop_if_aws(
+            responses_api_provider_config,
+            responses_api_provider_config.sign_request,
             headers=headers,
             optional_params=dict(litellm_params),
             request_data=data,
@@ -9845,7 +9861,9 @@ class BaseLLMHTTPHandler:
             )
         all_optional_params: Final[dict[str, object]] = dict(litellm_params)
         all_optional_params.update(vector_store_search_optional_params or {})
-        headers, signed_json_body = vector_store_provider_config.sign_request(
+        headers, signed_json_body = await sign_request_off_loop_if_aws(
+            vector_store_provider_config,
+            vector_store_provider_config.sign_request,
             headers=headers,
             optional_params=all_optional_params,
             request_data=request_body,
diff --git a/litellm/llms/dashscope/common_utils.py b/litellm/llms/dashscope/common_utils.py
index b7c97893a15..9ed9c276e43 100644
--- a/litellm/llms/dashscope/common_utils.py
+++ b/litellm/llms/dashscope/common_utils.py
@@ -2,7 +2,8 @@
 Common utilities for the DashScope LLM provider.
 """
 
-from typing import TYPE_CHECKING
+from typing import TYPE_CHECKING, Final
+from urllib.parse import urlparse
 
 import httpx
 
@@ -16,6 +17,27 @@ if TYPE_CHECKING:
     )
     from litellm.llms.base_llm.rerank.transformation import BaseRerankConfig
 
+DASHSCOPE_CHAT_COMPATIBLE_PATH: Final = "/compatible-mode/v1"
+DASHSCOPE_RERANK_PATH: Final = "/compatible-api/v1/reranks"
+
+
+def _rerank_base_for_chat_shaped_base(api_base: str | None) -> str | None:
+    if api_base is None:
+        return None
+    parsed: Final = urlparse(api_base)
+    host: Final = parsed.hostname or ""
+    on_aliyun_host: Final = host == "aliyuncs.com" or host.endswith(".aliyuncs.com")
+    if not on_aliyun_host or parsed.path.rstrip("/") != DASHSCOPE_CHAT_COMPATIBLE_PATH:
+        return None
+    return f"{parsed.scheme}://{parsed.netloc}{DASHSCOPE_RERANK_PATH}"
+
+
+def resolve_dashscope_family_rerank_api_base(api_base: str | None, env_var: str, default_rerank_base: str) -> str:
+    remapped: Final = _rerank_base_for_chat_shaped_base(api_base)
+    if api_base is not None and remapped is None:
+        return api_base
+    return get_secret_str(env_var) or remapped or default_rerank_base
+
 
 def get_dashscope_family_embedding_config(custom_llm_provider: str) -> "BaseEmbeddingConfig":
     if custom_llm_provider == "qwencloud":
diff --git a/litellm/llms/dashscope/qwen_ai_platform.py b/litellm/llms/dashscope/qwen_ai_platform.py
index 9a44eaf574a..6998a57e2b7 100644
--- a/litellm/llms/dashscope/qwen_ai_platform.py
+++ b/litellm/llms/dashscope/qwen_ai_platform.py
@@ -3,6 +3,7 @@ from typing import Final
 from litellm.secret_managers.main import get_secret_str
 
 from .chat.transformation import DashScopeChatConfig
+from .common_utils import resolve_dashscope_family_rerank_api_base
 from .embed.transformation import DashScopeEmbeddingConfig
 from .image_generation.transformation import DashScopeImageGenerationConfig
 from .rerank.transformation import DashScopeRerankConfig
@@ -51,7 +52,9 @@ class QwenAIPlatformRerankConfig(DashScopeRerankConfig):
         return _require_qwen_ai_platform_api_key(api_key)
 
     def _resolve_rerank_api_base(self, api_base: str | None) -> str:
-        return api_base or get_secret_str("QWEN_AI_PLATFORM_API_BASE_RERANK") or QWEN_AI_PLATFORM_RERANK_API_BASE
+        return resolve_dashscope_family_rerank_api_base(
+            api_base, "QWEN_AI_PLATFORM_API_BASE_RERANK", QWEN_AI_PLATFORM_RERANK_API_BASE
+        )
 
 
 class QwenAIPlatformImageGenerationConfig(DashScopeImageGenerationConfig):
diff --git a/litellm/llms/dashscope/qwencloud.py b/litellm/llms/dashscope/qwencloud.py
index d8d53e340ef..ac21a48dd3e 100644
--- a/litellm/llms/dashscope/qwencloud.py
+++ b/litellm/llms/dashscope/qwencloud.py
@@ -3,6 +3,7 @@ from typing import Final
 from litellm.secret_managers.main import get_secret_str
 
 from .chat.transformation import DashScopeChatConfig
+from .common_utils import resolve_dashscope_family_rerank_api_base
 from .embed.transformation import DashScopeEmbeddingConfig
 from .image_generation.transformation import DashScopeImageGenerationConfig
 from .rerank.transformation import DashScopeRerankConfig
@@ -51,7 +52,9 @@ class QwenCloudRerankConfig(DashScopeRerankConfig):
         return _require_qwencloud_api_key(api_key)
 
     def _resolve_rerank_api_base(self, api_base: str | None) -> str:
-        return api_base or get_secret_str("QWENCLOUD_API_BASE_RERANK") or QWENCLOUD_RERANK_API_BASE
+        return resolve_dashscope_family_rerank_api_base(
+            api_base, "QWENCLOUD_API_BASE_RERANK", QWENCLOUD_RERANK_API_BASE
+        )
 
 
 class QwenCloudImageGenerationConfig(DashScopeImageGenerationConfig):
diff --git a/litellm/llms/dashscope/rerank/transformation.py b/litellm/llms/dashscope/rerank/transformation.py
index 490757a0948..14ad756ec9c 100644
--- a/litellm/llms/dashscope/rerank/transformation.py
+++ b/litellm/llms/dashscope/rerank/transformation.py
@@ -12,8 +12,12 @@ Endpoint
 - https://dashscope.aliyuncs.com/compatible-api/v1/reranks
 
 Note: chat/embed live under `/compatible-mode/v1/`, but DashScope's rerank
-route is exposed under `/compatible-api/v1/reranks` per the docs. Override
-with `DASHSCOPE_API_BASE_RERANK` to point at a different host or path.
+route is exposed under `/compatible-api/v1/reranks` per the docs. A chat-shaped
+`.aliyuncs.com/compatible-mode/v1` base reaching this config (the chat default
+from `get_llm_provider`, or a `DASHSCOPE_API_BASE` env var) is redirected to
+the same host's rerank route, since `/compatible-mode/v1/reranks` is a dead
+route on every DashScope host. Override with `DASHSCOPE_API_BASE_RERANK` to
+point at a different host or path.
 
 Empirically, qwen3-rerank accepts `return_documents=true` and echoes
 `results[].document.text` back, even though the public docs list the flag
@@ -40,7 +44,7 @@ from litellm.types.rerank import (
     RerankTokens,
 )
 
-from ..common_utils import DashScopeError
+from ..common_utils import DashScopeError, resolve_dashscope_family_rerank_api_base
 
 DEFAULT_RERANK_URL: Final = "https://dashscope.aliyuncs.com/compatible-api/v1/reranks"
 
@@ -67,9 +71,7 @@ class DashScopeRerankConfig(BaseRerankConfig):
         return resolved_api_key
 
     def _resolve_rerank_api_base(self, api_base: str | None) -> str:
-        if api_base is not None:
-            return api_base
-        return get_secret_str("DASHSCOPE_API_BASE_RERANK") or DEFAULT_RERANK_URL
+        return resolve_dashscope_family_rerank_api_base(api_base, "DASHSCOPE_API_BASE_RERANK", DEFAULT_RERANK_URL)
 
     def get_complete_url(
         self,
diff --git a/litellm/llms/databricks/chat/transformation.py b/litellm/llms/databricks/chat/transformation.py
index e2e2ea5b553..09aaf970dc5 100644
--- a/litellm/llms/databricks/chat/transformation.py
+++ b/litellm/llms/databricks/chat/transformation.py
@@ -15,6 +15,7 @@ from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response impo
     _should_convert_tool_call_to_json_mode,
 )
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    _extract_reasoning_content,  # pyright: ignore[reportPrivateUsage]  # same import as the OpenAI transformation
     strip_litellm_internal_message_fields,
     strip_name_from_message,
 )
@@ -23,7 +24,9 @@ from litellm.types.llms.anthropic import AllAnthropicToolsValues
 from litellm.types.llms.databricks import (
     AllDatabricksContentValues,
     DatabricksChoice,
+    DatabricksDelta,
     DatabricksFunction,
+    DatabricksMessage,
     DatabricksResponse,
     DatabricksTool,
 )
@@ -247,8 +250,10 @@ class DatabricksConfig(DatabricksBase, OpenAILikeChatConfig, AnthropicConfig):
         litellm_params: dict,
         stream: bool | None = None,
     ) -> str:
-        api_base = self._get_api_base(api_base)
-        complete_url: Final = f"{api_base}/chat/completions"
+        use_ai_gateway: Final = model.removeprefix("databricks/").count(".") >= 2
+        api_base = self._get_api_base(api_base, use_ai_gateway=use_ai_gateway)
+        url_base: Final = api_base.rstrip("/") if use_ai_gateway else api_base
+        complete_url: Final = f"{url_base}/chat/completions"
         return complete_url
 
     def get_supported_openai_params(self, model: str | None = None) -> list:
@@ -534,6 +539,19 @@ class DatabricksConfig(DatabricksBase, OpenAILikeChatConfig, AnthropicConfig):
                             thinking_blocks.append(thinking_block)
         return reasoning_content, thinking_blocks
 
+    @staticmethod
+    def extract_top_level_reasoning_content(delta: DatabricksDelta) -> str | None:
+        return delta.get("reasoning_content")
+
+    @staticmethod
+    def resolve_reasoning_and_content(
+        message: DatabricksMessage, block_reasoning_content: str | None
+    ) -> tuple[str | None, str | None]:
+        content_str: Final = DatabricksConfig.extract_content_str(message["content"])
+        if block_reasoning_content is not None:
+            return block_reasoning_content, content_str
+        return _extract_reasoning_content({**message, "content": content_str})
+
     @staticmethod
     def extract_citations(
         content: AllDatabricksContentValues | None,
@@ -577,14 +595,13 @@ class DatabricksConfig(DatabricksBase, OpenAILikeChatConfig, AnthropicConfig):
                     finish_reason = "stop"
 
             if translated_message is None:
-                ## get the content str
-                content_str = DatabricksConfig.extract_content_str(choice["message"]["content"])
-
-                ## get the reasoning content
                 (
-                    reasoning_content,
+                    block_reasoning_content,
                     thinking_blocks,
                 ) = DatabricksConfig.extract_reasoning_content(choice["message"].get("content"))
+                reasoning_content, content_str = DatabricksConfig.resolve_reasoning_and_content(
+                    choice["message"], block_reasoning_content
+                )
 
                 citations = DatabricksConfig.extract_citations(choice["message"].get("content"))
 
@@ -738,12 +755,16 @@ class DatabricksChatResponseIterator(BaseModelResponseIterator):
 
                 # extract the reasoning content
                 (
-                    reasoning_content,
+                    block_reasoning_content,
                     thinking_blocks,
                 ) = DatabricksConfig.extract_reasoning_content(choice["delta"].get("content"))
 
                 choice["delta"]["content"] = content_str
-                choice["delta"]["reasoning_content"] = reasoning_content
+                choice["delta"]["reasoning_content"] = (
+                    block_reasoning_content
+                    if block_reasoning_content is not None
+                    else DatabricksConfig.extract_top_level_reasoning_content(choice["delta"])
+                )
                 choice["delta"]["thinking_blocks"] = thinking_blocks
                 translated_choices.append(choice)
             return ModelResponseStream(
diff --git a/litellm/llms/databricks/common_utils.py b/litellm/llms/databricks/common_utils.py
index 7695b1cb35e..a4ec2c5378b 100644
--- a/litellm/llms/databricks/common_utils.py
+++ b/litellm/llms/databricks/common_utils.py
@@ -177,19 +177,13 @@ class DatabricksBase:
         # Default: just litellm
         return f"litellm/{version}"
 
-    def _get_api_base(self, api_base: str | None) -> str:
-        """
-        Get the Databricks API base URL.
-
-        If not provided, attempts to get it from the Databricks SDK.
-        """
+    def _get_api_base(self, api_base: str | None, use_ai_gateway: bool = False) -> str:
         if api_base is None:
             try:
                 from databricks.sdk import WorkspaceClient
 
                 databricks_client: Final = WorkspaceClient()
                 api_base = f"{databricks_client.config.host}/serving-endpoints"
-                return api_base
             except ImportError:
                 raise DatabricksException(
                     status_code=400,
@@ -198,6 +192,18 @@ class DatabricksBase:
                         "or install the databricks-sdk Python library."
                     ),
                 )
+
+        if not use_ai_gateway:
+            return api_base
+
+        normalized_api_base: Final = api_base.rstrip("/")
+        if normalized_api_base.endswith("/ai-gateway/mlflow/v1"):
+            return normalized_api_base
+        if normalized_api_base.endswith("/serving-endpoints"):
+            return f"{normalized_api_base.removesuffix('/serving-endpoints')}/ai-gateway/mlflow/v1"
+        api_base_parts: Final = urlsplit(normalized_api_base)
+        if api_base_parts.path in ("", "/"):
+            return f"{normalized_api_base}/ai-gateway/mlflow/v1"
         return api_base
 
     def _get_oauth_m2m_token(
diff --git a/litellm/llms/hosted_vllm/image_edit/__init__.py b/litellm/llms/hosted_vllm/image_edit/__init__.py
new file mode 100644
index 00000000000..27e005e8a0d
--- /dev/null
+++ b/litellm/llms/hosted_vllm/image_edit/__init__.py
@@ -0,0 +1,9 @@
+from litellm.llms.base_llm.image_edit.transformation import BaseImageEditConfig
+
+from .transformation import HostedVLLMImageEditConfig
+
+__all__ = ("HostedVLLMImageEditConfig",)
+
+
+def get_hosted_vllm_image_edit_config(model: str) -> BaseImageEditConfig:
+    return HostedVLLMImageEditConfig()
diff --git a/litellm/llms/hosted_vllm/image_edit/transformation.py b/litellm/llms/hosted_vllm/image_edit/transformation.py
new file mode 100644
index 00000000000..3b8cc437168
--- /dev/null
+++ b/litellm/llms/hosted_vllm/image_edit/transformation.py
@@ -0,0 +1,43 @@
+from typing import Final
+
+from litellm.llms.openai.image_edit.transformation import OpenAIImageEditConfig
+from litellm.secret_managers.main import get_secret_str
+
+PARAMS_VLLM_OMNI_DOES_NOT_ACCEPT: Final = frozenset({"mask", "quality", "input_fidelity"})
+
+
+class HostedVLLMImageEditConfig(OpenAIImageEditConfig):
+    def get_supported_openai_params(self, model: str) -> list:  # mutable-ok: BaseImageEditConfig contract
+        return [  # mutable-ok: BaseImageEditConfig returns list
+            param
+            for param in super().get_supported_openai_params(model)
+            if param not in PARAMS_VLLM_OMNI_DOES_NOT_ACCEPT
+        ]
+
+    def validate_environment(
+        self,
+        headers: dict,  # mutable-ok: BaseImageEditConfig contract
+        model: str,
+        api_key: str | None = None,
+        litellm_params: dict | None = None,  # mutable-ok: BaseImageEditConfig contract
+        api_base: str | None = None,
+    ) -> dict:  # mutable-ok: BaseImageEditConfig contract
+        resolved_key: Final = api_key or get_secret_str("HOSTED_VLLM_API_KEY") or "fake-api-key"
+        return {**headers, "Authorization": f"Bearer {resolved_key}"}  # mutable-ok: httpx headers are a dict
+
+    def get_complete_url(
+        self,
+        model: str,
+        api_base: str | None,
+        litellm_params: dict,  # mutable-ok: BaseImageEditConfig contract
+    ) -> str:
+        resolved_api_base: Final = api_base or get_secret_str("HOSTED_VLLM_API_BASE")
+        if resolved_api_base is None:
+            raise ValueError(
+                "api_base not set for Hosted VLLM images edits API. "
+                "Set via api_base parameter or HOSTED_VLLM_API_BASE environment variable"
+            )
+        trimmed: Final = resolved_api_base.rstrip("/")
+        if trimmed.endswith("/v1"):
+            return f"{trimmed}/images/edits"
+        return f"{trimmed}/v1/images/edits"
diff --git a/litellm/llms/jina_ai/rerank/transformation.py b/litellm/llms/jina_ai/rerank/transformation.py
index a8f3388d092..2a81c38fe34 100644
--- a/litellm/llms/jina_ai/rerank/transformation.py
+++ b/litellm/llms/jina_ai/rerank/transformation.py
@@ -157,9 +157,6 @@ class JinaAIRerankConfig(BaseRerankConfig):
         billed_units: RerankBilledUnits | None = None,
         model_info: ModelInfo | None = None,
     ) -> tuple[float, float]:
-        """
-        Jina AI reranker is priced at $0.000000018 per token.
-        """
         if (
             model_info is None
             or "input_cost_per_token" not in model_info
diff --git a/litellm/llms/openai/chat/gpt_transformation.py b/litellm/llms/openai/chat/gpt_transformation.py
index 9afc6331d96..9b410cf073e 100644
--- a/litellm/llms/openai/chat/gpt_transformation.py
+++ b/litellm/llms/openai/chat/gpt_transformation.py
@@ -19,10 +19,12 @@ from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response impo
     _should_convert_tool_call_to_json_mode,
 )
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    drop_non_python_regex_patterns,
     drop_tool_reference_parts_from_tool_messages,
+    flatten_combinators_and_drop_non_python_regex_patterns,
     get_tool_call_names,
     hoist_images_from_tool_messages,
-    tool_with_flattened_parameters,
+    tool_with_sanitized_parameters,
 )
 from litellm.litellm_core_utils.prompt_templates.image_handling import (
     async_convert_url_to_base64,
@@ -432,7 +434,7 @@ class OpenAIGPTConfig(BaseLLMModelInfo, BaseConfig):
             custom_llm_provider, api_base
         )
 
-    def _flattened_tools_update_for_openai(
+    def _sanitized_tools_update_for_openai(
         self,
         optional_params: Mapping[str, object],
         litellm_params: Mapping[str, object],
@@ -440,22 +442,26 @@ class OpenAIGPTConfig(BaseLLMModelInfo, BaseConfig):
         """
         OpenAI's chat completions validator rejects tool `parameters` carrying
         'oneOf'/'anyOf'/'allOf'/'enum'/'const'/'not' at the top level for every
-        model family, unlike the Responses API, where GPT-5+ accepts them.
+        model family, unlike the Responses API, where GPT-5+ accepts them, and
+        a `pattern` Python's `re` cannot compile for every model family on both.
+        A custom api_base on the `openai` provider is usually a proxy in front of
+        the same validator, so regexes are dropped there too, while the lossier
+        combinator flattening stays limited to api.openai.com hosts.
         """
         tools: Final = optional_params.get("tools")
-        if not isinstance(tools, list):
-            return _NO_TOOLS_UPDATE
         provider: Final = litellm_params.get("custom_llm_provider")
-        raw_api_base: Final = litellm_params.get("api_base")
-        if not self._targets_openai_hosted_endpoint(
-            provider if isinstance(provider, str) else None,
-            raw_api_base if isinstance(raw_api_base, str) else None,
-        ):
+        if not isinstance(tools, list) or provider != "openai":
             return _NO_TOOLS_UPDATE
-        flattened: Final = [  # mutable-ok: request tools are a JSON list
-            tool_with_flattened_parameters(tool) if isinstance(tool, dict) else tool for tool in tools
+        raw_api_base: Final = litellm_params.get("api_base")
+        sanitize: Final = (
+            flatten_combinators_and_drop_non_python_regex_patterns
+            if self._targets_openai_hosted_endpoint(provider, raw_api_base if isinstance(raw_api_base, str) else None)
+            else drop_non_python_regex_patterns
+        )
+        sanitized: Final = [  # mutable-ok: request tools are a JSON list
+            tool_with_sanitized_parameters(tool, sanitize) if isinstance(tool, dict) else tool for tool in tools
         ]
-        return MappingProxyType({"tools": flattened})
+        return MappingProxyType({"tools": sanitized})
 
     def transform_request(
         self,
@@ -489,7 +495,7 @@ class OpenAIGPTConfig(BaseLLMModelInfo, BaseConfig):
             "model": model,
             "messages": messages,
             **optional_params,
-            **self._flattened_tools_update_for_openai(optional_params, litellm_params),
+            **self._sanitized_tools_update_for_openai(optional_params, litellm_params),
         }
 
     async def async_transform_request(
@@ -521,7 +527,7 @@ class OpenAIGPTConfig(BaseLLMModelInfo, BaseConfig):
                 "model": model,
                 "messages": transformed_messages,
                 **optional_params,
-                **self._flattened_tools_update_for_openai(optional_params, litellm_params),
+                **self._sanitized_tools_update_for_openai(optional_params, litellm_params),
             }
         else:
             ## allow for any object specific behaviour to be handled
diff --git a/litellm/llms/openai/chat/guardrail_translation/handler.py b/litellm/llms/openai/chat/guardrail_translation/handler.py
index 80292aef2cf..58ff03e6a0d 100644
--- a/litellm/llms/openai/chat/guardrail_translation/handler.py
+++ b/litellm/llms/openai/chat/guardrail_translation/handler.py
@@ -49,6 +49,8 @@ from litellm.types.proxy.guardrails.guardrail_hooks.generic_guardrail_api import
     coerce_stream_holdback_value,
 )
 from litellm.types.utils import (
+    ChatCompletionDeltaToolCall,
+    ChatCompletionMessageToolCall,
     Choices,
     GenericGuardrailAPIInputs,
     ModelResponse,
@@ -78,7 +80,8 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
     Methods can be overridden to customize behavior for different message formats.
     """
 
-    delivers_ended_stream_text_rewrites = True
+    delivers_ended_stream_rewrites = True
+    assembles_streamed_response = True
 
     def get_structured_messages(self, data: dict) -> list[AllMessageValues] | None:
         """
@@ -610,13 +613,14 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
         deliver_ended_stream_rewrites: bool,
     ) -> None:
         """Ended-stream path: rebuild the full response, run the non-streaming
-        output guardrail against it, and (when opted in) write any text rewrite
-        back across the buffered chunks."""
+        output guardrail against it, and (when opted in) write any text or
+        tool-call rewrite back across the buffered chunks."""
         model_response: Final = cast(
             ModelResponse,
             stream_chunk_builder(chunks=responses_so_far, logging_obj=litellm_logging_obj),
         )
         pre_guardrail_texts: Final = self._string_choice_contents(model_response)
+        pre_guardrail_tool_calls: Final = self._function_tool_call_shapes(model_response)
         await self.process_output_response(
             response=model_response,
             guardrail_to_apply=guardrail_to_apply,
@@ -624,13 +628,21 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
             user_api_key_dict=user_api_key_dict,
             request_data=request_data,
         )
-        if deliver_ended_stream_rewrites:
-            await self._write_ended_stream_text_rewrites(
-                responses_so_far=responses_so_far,
-                guardrailed_response=model_response,
-                pre_guardrail_texts=pre_guardrail_texts,
-                guardrail_name=guardrail_to_apply.guardrail_name or "unknown",
-            )
+        if not deliver_ended_stream_rewrites:
+            return
+        guardrail_name: Final = guardrail_to_apply.guardrail_name or "unknown"
+        await self._write_ended_stream_text_rewrites(
+            responses_so_far=responses_so_far,
+            guardrailed_response=model_response,
+            pre_guardrail_texts=pre_guardrail_texts,
+            guardrail_name=guardrail_name,
+        )
+        self._write_ended_stream_tool_call_rewrites(
+            responses_so_far=responses_so_far,
+            guardrailed_response=model_response,
+            pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+            guardrail_name=guardrail_name,
+        )
 
     def build_stream_error_items(
         self,
@@ -1043,6 +1055,71 @@ class OpenAIChatCompletionsHandler(BaseTranslation):
             task_mappings=[(target_choice_index, None) for _ in changed],  # mutable-ok: callee takes lists
         )
 
+    @staticmethod
+    def _function_tool_call_shapes(response: "ModelResponse") -> tuple[tuple[str | None, str], ...]:
+        return tuple(
+            (tool_call.function.name, tool_call.function.arguments)
+            for choice in response.choices
+            for tool_call in choice.message.tool_calls or ()
+            if isinstance(tool_call, ChatCompletionMessageToolCall)
+        )
+
+    @staticmethod
+    def _function_tool_call_fragments(
+        responses_so_far: Sequence["ModelResponseStream"],
+    ) -> tuple[tuple[ChatCompletionDeltaToolCall, ...], ...]:
+        """Group the stream's function tool-call fragments by their tool-call index, in
+        the index order ``stream_chunk_builder`` lists the rebuilt tool calls, keeping
+        only the indices the builder keeps (an id and a name somewhere in the stream)."""
+        fragments: Final = tuple(
+            tool_call
+            for response in responses_so_far
+            for choice in response.choices
+            for tool_call in choice.delta.tool_calls or ()
+            if isinstance(tool_call, ChatCompletionDeltaToolCall)
+        )
+        identified: Final = frozenset(fragment.index for fragment in fragments if fragment.id)
+        named: Final = frozenset(fragment.index for fragment in fragments if fragment.function.name)
+        return tuple(
+            tuple(fragment for fragment in fragments if fragment.index == index) for index in sorted(identified & named)
+        )
+
+    def _write_ended_stream_tool_call_rewrites(
+        self,
+        responses_so_far: list["ModelResponseStream"],  # mutable-ok: rewrites the caller's buffered chunks in place
+        guardrailed_response: "ModelResponse",
+        pre_guardrail_tool_calls: tuple[tuple[str | None, str], ...],
+        guardrail_name: str,
+    ) -> None:
+        """Write ended-stream guardrail tool-call rewrites back across the buffered
+        chunks: the rewritten name and full arguments land in the tool call's first
+        fragment and the arguments of its later fragments are blanked, mirroring the
+        text write-back. A rewrite on a stream carrying more than one distinct choice
+        index, or whose fragments do not line up with the rebuilt tool calls, is
+        reported as undeliverable, so the pipeline executor discards it and releases
+        the original chunks."""
+        post_guardrail_tool_calls: Final = self._function_tool_call_shapes(guardrailed_response)
+        if post_guardrail_tool_calls == pre_guardrail_tool_calls:
+            return
+        stream_choice_indices: Final = frozenset(
+            choice.index for response in responses_so_far for choice in response.choices
+        )
+        fragments_by_tool_call: Final = self._function_tool_call_fragments(responses_so_far)
+        if len(stream_choice_indices) != 1 or len(fragments_by_tool_call) != len(post_guardrail_tool_calls):
+            from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+            raise UndeliverableStreamRewrite(guardrail_name)
+        for before, (name, arguments), fragments in zip(
+            pre_guardrail_tool_calls, post_guardrail_tool_calls, fragments_by_tool_call
+        ):
+            if (name, arguments) == before:
+                continue
+            head, *tail = fragments
+            head.function.name = name
+            head.function.arguments = arguments
+            for fragment in tail:
+                fragment.function.arguments = ""
+
     async def _apply_guardrail_responses_to_output_streaming(
         self,
         responses: list["ModelResponseStream"],
diff --git a/litellm/llms/openai/openai.py b/litellm/llms/openai/openai.py
index edc8d64d9c2..5f04ebe0c01 100644
--- a/litellm/llms/openai/openai.py
+++ b/litellm/llms/openai/openai.py
@@ -797,6 +797,7 @@ class OpenAIChatCompletion(BaseLLM, BaseOpenAILLM):
                                 "api_base": openai_client._base_url._uri_reference,
                                 "acompletion": acompletion,
                                 "complete_input_dict": data,
+                                "openai_sdk": True,
                             },
                         )
 
@@ -938,6 +939,7 @@ class OpenAIChatCompletion(BaseLLM, BaseOpenAILLM):
                         "api_base": openai_aclient._base_url._uri_reference,
                         "acompletion": True,
                         "complete_input_dict": data,
+                        "openai_sdk": True,
                     },
                 )
 
diff --git a/litellm/llms/openai/responses/guardrail_translation/handler.py b/litellm/llms/openai/responses/guardrail_translation/handler.py
index b0f79552bc5..33e0a0a923f 100644
--- a/litellm/llms/openai/responses/guardrail_translation/handler.py
+++ b/litellm/llms/openai/responses/guardrail_translation/handler.py
@@ -37,14 +37,14 @@ from itertools import accumulate, chain, repeat
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, NamedTuple, Union, cast
 
-from openai.types.responses.response_function_tool_call import ResponseFunctionToolCall
-from pydantic import BaseModel, TypeAdapter
+from pydantic import BaseModel, ConfigDict, TypeAdapter, ValidationError
 from typing_extensions import ReadOnly, TypedDict
 
 from litellm._logging import verbose_proxy_logger
 from litellm.completion_extras.litellm_responses_transformation.transformation import (
     LiteLLMResponsesTransformationHandler,
     OpenAiResponsesToChatCompletionStreamIterator,
+    tool_call_dict_from_output_item,
 )
 from litellm.llms.base_llm.guardrail_translation.base_translation import (
     BaseTranslation,
@@ -84,7 +84,6 @@ from litellm.types.llms.openai import (
 )
 from litellm.types.responses.main import (
     GenericResponseOutputItem,
-    OutputFunctionToolCall,
     OutputText,
 )
 from litellm.types.utils import GenericGuardrailAPIInputs
@@ -101,6 +100,72 @@ if TYPE_CHECKING:
     from litellm.types.llms.openai import ResponseInputParam
 
 
+class _ToolCallShape(NamedTuple):
+    name: str | None
+    arguments: str
+
+
+class _ToolCallFunctionFields(BaseModel):
+    model_config = ConfigDict(frozen=True)
+
+    name: str | None = None
+    arguments: str = ""
+
+
+class _ToolCallFields(BaseModel):
+    model_config = ConfigDict(frozen=True)
+
+    function: _ToolCallFunctionFields
+
+
+def _tool_call_shapes(tool_calls: Sequence[ChatCompletionToolCallChunk]) -> tuple[_ToolCallShape, ...]:
+    return tuple(
+        _ToolCallShape(name=tool_call["function"].get("name"), arguments=tool_call["function"].get("arguments", ""))
+        for tool_call in tool_calls
+    )
+
+
+def _returned_tool_call_shape(tool_call: object) -> _ToolCallShape | None:
+    payload: Final = tool_call.model_dump() if isinstance(tool_call, BaseModel) else tool_call
+    try:
+        fields: Final = _ToolCallFields.model_validate(payload)
+    except ValidationError:
+        return None
+    return _ToolCallShape(name=fields.function.name, arguments=fields.function.arguments)
+
+
+def _post_guardrail_tool_call_shapes(
+    returned_tool_calls: Sequence[object] | None,
+    pre_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+    guardrail_name: str | None,
+) -> tuple[_ToolCallShape, ...]:
+    if not pre_guardrail_tool_calls:
+        return pre_guardrail_tool_calls
+    if returned_tool_calls is None or len(returned_tool_calls) != len(pre_guardrail_tool_calls):
+        verbose_proxy_logger.warning(
+            "OpenAI Responses API: guardrail %s returned %s tool calls for the %d scanned, "
+            "leaving the tool call output items unchanged",
+            guardrail_name,
+            "no" if returned_tool_calls is None else len(returned_tool_calls),
+            len(pre_guardrail_tool_calls),
+        )
+        return pre_guardrail_tool_calls
+    returned_shapes: Final = tuple(_returned_tool_call_shape(tool_call) for tool_call in returned_tool_calls)
+    validated_shapes: Final = tuple(shape for shape in returned_shapes if shape is not None)
+    if len(validated_shapes) != len(returned_shapes):
+        verbose_proxy_logger.warning(
+            "OpenAI Responses API: guardrail %s returned tool calls without a function name and arguments, "
+            "leaving the tool call output items unchanged",
+            guardrail_name,
+        )
+        return pre_guardrail_tool_calls
+    return validated_shapes
+
+
+def _tool_call_rewrite(before: _ToolCallShape, after: _ToolCallShape) -> _ToolCallShape:
+    return _ToolCallShape(name=after.name if after.name != before.name else None, arguments=after.arguments)
+
+
 class ResponseOutputEnvelope(TypedDict, total=False):
     """Dict form of a Responses API response, as far as guardrail write-back reads it."""
 
@@ -128,6 +193,20 @@ _TERMINAL_ENVELOPE_EVENT_TYPES: Final = frozenset(
 )
 
 
+_TOOL_CALL_ITEM_TYPES: Final = frozenset({"function_call", "custom_tool_call"})
+_TOOL_CALL_PAYLOAD_FIELDS: Final[Mapping[str, str]] = MappingProxyType(
+    {"function_call": "arguments", "custom_tool_call": "input"}
+)
+_TOOL_CALL_PAYLOAD_DELTA_EVENT_TYPES: Final = frozenset(
+    {"response.function_call_arguments.delta", "response.custom_tool_call_input.delta"}
+)
+_TOOL_CALL_PAYLOAD_DONE_EVENT_FIELDS: Final[Mapping[str, str]] = MappingProxyType(
+    {"response.function_call_arguments.done": "arguments", "response.custom_tool_call_input.done": "input"}
+)
+_TOOL_CALL_PAYLOAD_EVENT_TYPES: Final = _TOOL_CALL_PAYLOAD_DELTA_EVENT_TYPES | frozenset(
+    _TOOL_CALL_PAYLOAD_DONE_EVENT_FIELDS
+)
+_OUTPUT_ITEM_EVENT_TYPES: Final = frozenset({"response.output_item.added", "response.output_item.done"})
 _PATCHABLE_ITEM_FIELDS: Final[Mapping[str, str]] = MappingProxyType(
     {"function_call_output": "output", "message": "content"}
 )
@@ -164,8 +243,20 @@ def _rewritten_input_item(item: Mapping[str, object], rewritten: object) -> Mapp
     return {**item, field: converted_value}  # mutable-ok: request input items must stay JSON-plain dicts
 
 
-def _is_function_call_item(item: object) -> bool:
-    return isinstance(item, Mapping) and item.get("type") in ("function_call", "custom_tool_call")
+def _is_tool_call_item(item: object) -> bool:
+    return isinstance(item, Mapping) and item.get("type") in _TOOL_CALL_ITEM_TYPES
+
+
+def _tool_call_output_item_mapping(item: object) -> Mapping[str, object] | None:
+    if stream_item_field(item, "type") not in _TOOL_CALL_ITEM_TYPES:
+        return None
+    if isinstance(item, Mapping):
+        return cast("Mapping[str, object]", item)  # cast-ok: output items are str-keyed JSON objects
+    return item.model_dump() if isinstance(item, BaseModel) else None
+
+
+def _is_tool_call_output_item(item: object) -> bool:
+    return _tool_call_output_item_mapping(item) is not None
 
 
 def _last_message_role(messages: Sequence[object]) -> str | None:
@@ -189,7 +280,7 @@ def _provenance_unit_bounds(
     start_indexes: Final = tuple(
         index
         for index in range(len(raw_input))
-        if index == 0 or not (_is_function_call_item(raw_input[index]) and trailing_roles[index - 1] == "assistant")
+        if index == 0 or not (_is_tool_call_item(raw_input[index]) and trailing_roles[index - 1] == "assistant")
     )
     return tuple(zip(start_indexes, (*start_indexes[1:], len(raw_input))))
 
@@ -340,7 +431,8 @@ class OpenAIResponsesHandler(BaseTranslation):
     Methods can be overridden to customize behavior for different message formats.
     """
 
-    delivers_ended_stream_text_rewrites = True
+    delivers_ended_stream_rewrites = True
+    assembles_streamed_response = True
 
     def get_structured_messages(self, data: dict) -> list[AllMessageValues] | None:
         """
@@ -587,7 +679,7 @@ class OpenAIResponsesHandler(BaseTranslation):
             - response.output is a list of output items
             - Each output item can be:
               * GenericResponseOutputItem with a content list of OutputText objects
-              * ResponseFunctionToolCall with tool call data
+              * ResponseFunctionToolCall or CustomToolCallOutputItem with tool call data
             - Each OutputText object has a text field
         """
 
@@ -652,6 +744,7 @@ class OpenAIResponsesHandler(BaseTranslation):
             if response_model:
                 inputs["model"] = response_model
 
+            pre_guardrail_tool_calls: Final = _tool_call_shapes(tool_calls_to_check)
             guardrailed_inputs: Final = await guardrail_to_apply.apply_guardrail(
                 inputs=inputs,
                 request_data=request_data,
@@ -660,6 +753,11 @@ class OpenAIResponsesHandler(BaseTranslation):
             )
 
             guardrailed_texts: Final = guardrailed_inputs.get("texts", [])
+            post_guardrail_tool_calls: Final = _post_guardrail_tool_call_shapes(
+                returned_tool_calls=guardrailed_inputs.get("tool_calls"),
+                pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+                guardrail_name=guardrail_to_apply.guardrail_name,
+            )
 
             # Step 3: Map guardrail responses back to original response structure
             await self._apply_guardrail_responses_to_output(
@@ -667,6 +765,11 @@ class OpenAIResponsesHandler(BaseTranslation):
                 responses=guardrailed_texts,
                 task_mappings=task_mappings,
             )
+            self._write_tool_call_rewrites_to_output(
+                tool_call_items=tuple(item for item in response_output if _is_tool_call_output_item(item)),
+                pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+                post_guardrail_tool_calls=post_guardrail_tool_calls,
+            )
 
         verbose_proxy_logger.debug("OpenAI Responses API: Processed output response: %s", response)
 
@@ -754,6 +857,7 @@ class OpenAIResponsesHandler(BaseTranslation):
                 if response_model:
                     inputs["model"] = response_model
 
+                pre_guardrail_tool_calls: Final = _tool_call_shapes(tool_calls_to_check)
                 guardrailed_inputs: Final = await guardrail_to_apply.apply_guardrail(
                     inputs=inputs,
                     request_data=request_data,
@@ -762,6 +866,11 @@ class OpenAIResponsesHandler(BaseTranslation):
                 )
 
                 guardrailed_texts: Final = guardrailed_inputs.get("texts", [])
+                post_guardrail_tool_calls: Final = _post_guardrail_tool_call_shapes(
+                    returned_tool_calls=guardrailed_inputs.get("tool_calls"),
+                    pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+                    guardrail_name=guardrail_to_apply.guardrail_name,
+                )
 
                 # Write guardrailed texts back into the output items in-place.
                 # final_chunk is a reference into responses_so_far so this
@@ -784,6 +893,13 @@ class OpenAIResponsesHandler(BaseTranslation):
                             stream_events=responses_so_far[:-1],
                             rewrites_by_position=rewrites_by_position,
                         )
+                    self._deliver_ended_stream_tool_call_rewrites(
+                        responses_so_far=responses_so_far,
+                        outputs=outputs,
+                        pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+                        post_guardrail_tool_calls=post_guardrail_tool_calls,
+                        guardrail_name=guardrail_to_apply.guardrail_name or "unknown",
+                    )
                 return responses_so_far
 
         # ------------------------------------------------------------------ #
@@ -894,6 +1010,148 @@ class OpenAIResponsesHandler(BaseTranslation):
                 continue
             OpenAIResponsesHandler._write_event_field(content[content_idx], "text", rewritten)
 
+    def _deliver_ended_stream_tool_call_rewrites(
+        self,
+        responses_so_far: Sequence[object],
+        outputs: Sequence[object],
+        pre_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+        post_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+        guardrail_name: str,
+    ) -> None:
+        """Write ended-stream guardrail tool-call rewrites into the completed
+        envelope's ``function_call`` and ``custom_tool_call`` items and sync the
+        earlier stream events, keyed by ``call_id``. The guardrail sees the
+        envelope's tool calls in output order, which is how a rewritten call
+        finds its ``call_id``; the stream events find their call through the
+        ``call_id`` on ``output_item`` events and the ``item_id`` on argument
+        and custom-input events, since an
+        event's ``output_index`` need not match the envelope's (the chat bridge
+        numbers tool calls from 1 while the envelope lists them after the
+        message). A rewrite whose calls do not line up with the envelope, or
+        whose events cannot be found, is reported as undeliverable, so the
+        pipeline executor discards it and releases the original events."""
+        if post_guardrail_tool_calls == pre_guardrail_tool_calls:
+            return
+        tool_call_items: Final = tuple(output_item for output_item in outputs if _is_tool_call_output_item(output_item))
+        call_ids: Final = tuple(
+            call_id
+            for output_item in tool_call_items
+            if isinstance(call_id := stream_item_field(output_item, "call_id"), str) and call_id
+        )
+        stream_events: Final = responses_so_far[:-1]
+        call_id_by_item_id: Final = self._tool_call_ids_by_item_id(stream_events)
+        event_call_ids: Final = tuple(
+            self._tool_call_event_call_id(event, call_id_by_item_id) for event in stream_events
+        )
+        rewrites_by_call_id: Final = MappingProxyType(
+            {
+                call_id: _tool_call_rewrite(before, after)
+                for call_id, before, after in zip(call_ids, pre_guardrail_tool_calls, post_guardrail_tool_calls)
+                if after != before
+            }
+        )
+        unresolved_argument_event: Final = any(
+            call_id is None and stream_item_field(event, "type") in _TOOL_CALL_PAYLOAD_EVENT_TYPES
+            for event, call_id in zip(stream_events, event_call_ids)
+        )
+        if (
+            len(call_ids) != len(tool_call_items)
+            or len(frozenset(call_ids)) != len(call_ids)
+            or len(call_ids) != len(post_guardrail_tool_calls)
+            or unresolved_argument_event
+            or not rewrites_by_call_id.keys() <= frozenset(event_call_ids)
+        ):
+            from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+            raise UndeliverableStreamRewrite(guardrail_name)
+        for output_item, rewrite in (
+            (output_item, rewrites_by_call_id[call_id])
+            for output_item, call_id in zip(tool_call_items, call_ids)
+            if call_id in rewrites_by_call_id
+        ):
+            self._write_tool_call_item(output_item, rewrite.name, rewrite.arguments)
+        delta_replacements: Final = MappingProxyType(
+            {call_id: chain((rewrite.arguments,), repeat("")) for call_id, rewrite in rewrites_by_call_id.items()}
+        )
+        for event, call_id in zip(stream_events, event_call_ids):
+            if call_id not in rewrites_by_call_id:
+                continue
+            match stream_item_field(event, "type"):
+                case str() as event_type if event_type in _TOOL_CALL_PAYLOAD_DELTA_EVENT_TYPES:
+                    self._write_event_field(event, "delta", next(delta_replacements[call_id]))
+                case str() as event_type if event_type in _TOOL_CALL_PAYLOAD_DONE_EVENT_FIELDS:
+                    self._write_event_field(
+                        event, _TOOL_CALL_PAYLOAD_DONE_EVENT_FIELDS[event_type], rewrites_by_call_id[call_id].arguments
+                    )
+                case "response.output_item.added":
+                    self._write_tool_call_item(
+                        stream_item_field(event, "item"), rewrites_by_call_id[call_id].name, None
+                    )
+                case "response.output_item.done":
+                    self._write_tool_call_item(
+                        stream_item_field(event, "item"),
+                        rewrites_by_call_id[call_id].name,
+                        rewrites_by_call_id[call_id].arguments,
+                    )
+                case _:
+                    pass
+
+    def _write_tool_call_rewrites_to_output(
+        self,
+        tool_call_items: Sequence[object],
+        pre_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+        post_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+    ) -> None:
+        if len(tool_call_items) != len(post_guardrail_tool_calls):
+            return
+        for output_item, rewrite in (
+            (output_item, _tool_call_rewrite(before, after))
+            for output_item, before, after in zip(tool_call_items, pre_guardrail_tool_calls, post_guardrail_tool_calls)
+            if after != before
+        ):
+            self._write_tool_call_item(output_item, rewrite.name, rewrite.arguments)
+
+    @staticmethod
+    def _tool_call_ids_by_item_id(stream_events: Sequence[object]) -> Mapping[str, str]:
+        items: Final = tuple(
+            stream_item_field(event, "item")
+            for event in stream_events
+            if stream_item_field(event, "type") in _OUTPUT_ITEM_EVENT_TYPES
+        )
+        return MappingProxyType(
+            {
+                item_id: call_id
+                for item in items
+                if stream_item_field(item, "type") in _TOOL_CALL_ITEM_TYPES
+                and isinstance(item_id := stream_item_field(item, "id"), str)
+                and isinstance(call_id := stream_item_field(item, "call_id"), str)
+            }
+        )
+
+    @staticmethod
+    def _tool_call_event_call_id(event: object, call_id_by_item_id: Mapping[str, str]) -> str | None:
+        event_type: Final = stream_item_field(event, "type")
+        if event_type in _TOOL_CALL_PAYLOAD_EVENT_TYPES:
+            item_id: Final = stream_item_field(event, "item_id")
+            return call_id_by_item_id.get(item_id) if isinstance(item_id, str) else None
+        if event_type not in _OUTPUT_ITEM_EVENT_TYPES:
+            return None
+        item: Final = stream_item_field(event, "item")
+        call_id: Final = stream_item_field(item, "call_id")
+        return (
+            call_id if stream_item_field(item, "type") in _TOOL_CALL_ITEM_TYPES and isinstance(call_id, str) else None
+        )
+
+    @staticmethod
+    def _write_tool_call_item(item: object, name: str | None, payload: str | None) -> None:
+        if item is None:
+            return
+        if name is not None:
+            OpenAIResponsesHandler._write_event_field(item, "name", name)
+        item_type: Final = stream_item_field(item, "type")
+        if payload is not None and isinstance(item_type, str) and item_type in _TOOL_CALL_PAYLOAD_FIELDS:
+            OpenAIResponsesHandler._write_event_field(item, _TOOL_CALL_PAYLOAD_FIELDS[item_type], payload)
+
     def _check_streaming_has_ended(self, responses_so_far: Sequence[object]) -> bool:
         """
         Check if the streaming has ended.
@@ -920,7 +1178,7 @@ class OpenAIResponsesHandler(BaseTranslation):
     def _completed_response_scan_key(response: object) -> StreamingScanKey:
         output_items: Final = stream_item_items(response, "output")
         message_items: Final = tuple(
-            item for item in output_items if stream_item_field(item, "type") != "function_call"
+            item for item in output_items if stream_item_field(item, "type") not in _TOOL_CALL_ITEM_TYPES
         )
         return StreamingScanKey(
             texts=tuple(
@@ -932,7 +1190,7 @@ class OpenAIResponsesHandler(BaseTranslation):
             tool_calls=tuple(
                 stream_item_fingerprint(item)
                 for item in output_items
-                if stream_item_field(item, "type") == "function_call"
+                if stream_item_field(item, "type") in _TOOL_CALL_ITEM_TYPES
             ),
             stream_ended=True,
         )
@@ -1043,34 +1301,10 @@ class OpenAIResponsesHandler(BaseTranslation):
         Override this method to customize text/image/tool extraction logic.
         """
 
-        # Check if this is a tool call (OutputFunctionToolCall)
-        if isinstance(output_item, OutputFunctionToolCall) or (
-            isinstance(output_item, BaseModel)
-            and hasattr(output_item, "type")
-            and getattr(output_item, "type") == "function_call"
-        ):
+        tool_call_item: Final = _tool_call_output_item_mapping(output_item)
+        if tool_call_item is not None:
             if tool_calls_to_check is not None:
-                tool_call_dict = (
-                    LiteLLMCompletionResponsesConfig.convert_response_function_tool_call_to_chat_completion_tool_call(
-                        tool_call_item=output_item,
-                        index=output_idx,
-                    )
-                )
-                tool_calls_to_check.append(cast(ChatCompletionToolCallChunk, tool_call_dict))
-            return
-        elif isinstance(output_item, dict) and output_item.get("type") == "function_call":
-            # Handle dict representation of tool call
-            if tool_calls_to_check is not None:
-                # Convert dict to ResponseFunctionToolCall for processing
-                try:
-                    tool_call_obj: Final = ResponseFunctionToolCall(**output_item)
-                    tool_call_dict = LiteLLMCompletionResponsesConfig.convert_response_function_tool_call_to_chat_completion_tool_call(
-                        tool_call_item=tool_call_obj,
-                        index=output_idx,
-                    )
-                    tool_calls_to_check.append(cast(ChatCompletionToolCallChunk, tool_call_dict))
-                except Exception:
-                    pass
+                tool_calls_to_check.append(tool_call_dict_from_output_item(tool_call_item, output_idx))
             return
 
         # Handle both GenericResponseOutputItem and dict
diff --git a/litellm/llms/openai/responses/transformation.py b/litellm/llms/openai/responses/transformation.py
index 926de3e8854..833ae206024 100644
--- a/litellm/llms/openai/responses/transformation.py
+++ b/litellm/llms/openai/responses/transformation.py
@@ -1,4 +1,4 @@
-from collections.abc import Mapping, Sequence
+from collections.abc import Callable, Mapping, Sequence
 from functools import lru_cache
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Protocol, cast, get_type_hints
@@ -15,6 +15,10 @@ from litellm.litellm_core_utils.get_model_cost_map import GetModelCostMap
 from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response import (
     _safe_convert_created_field,
 )
+from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    drop_non_python_regex_patterns,
+    flatten_combinators_and_drop_non_python_regex_patterns,
+)
 from litellm.litellm_core_utils.safe_json_loads import safe_json_loads
 from litellm.litellm_core_utils.url_utils import encode_url_path_segment
 from litellm.llms.base_llm.responses.transformation import BaseResponsesAPIConfig
@@ -40,7 +44,7 @@ else:
 
 _NO_TOOL_UPDATE: Final[Mapping[str, object]] = MappingProxyType({})
 _MODEL_FAMILIES_REJECTING_TOP_LEVEL_SCHEMA_COMBINATORS: Final = ("gpt-4", "gpt-3.5", "chatgpt-4o", "o1", "o3", "o4")
-_PROVIDERS_WITH_COMBINATOR_REJECTING_VALIDATOR: Final = frozenset({LlmProviders.AZURE, LlmProviders.OPENAI})
+_PROVIDERS_WITH_OPENAI_SCHEMA_VALIDATOR: Final = frozenset({LlmProviders.AZURE, LlmProviders.OPENAI})
 _PROVIDERS_VALIDATING_TOOL_CALL_ITEM_IDS: Final = frozenset({LlmProviders.AZURE, LlmProviders.OPENAI})
 
 
@@ -106,6 +110,9 @@ class OpenAIResponsesAPIConfig(BaseResponsesAPIConfig):
     def supports_native_file_search(self) -> bool:
         return True
 
+    def supports_encrypted_agent_messages(self) -> bool:
+        return self.custom_llm_provider in (LlmProviders.OPENAI, LlmProviders.AZURE)
+
     @staticmethod
     def _is_gpt_5_model(model: str) -> bool:
         """Return True only for actual OpenAI GPT-5 models.
@@ -293,7 +300,7 @@ class OpenAIResponsesAPIConfig(BaseResponsesAPIConfig):
             model=model, input=validated_input, tools=tools
         )
         object_schema_tools: Final = self._tools_with_object_parameters(model=model, tools=stripped_tools)
-        sanitized_tools: Final = self._flatten_tool_schema_combinators_for_openai(
+        sanitized_tools: Final = self._sanitized_tool_schemas_for_openai(
             model=model, tools=object_schema_tools, litellm_params=litellm_params
         )
         return self._drop_foreign_tool_call_item_ids(stripped_input), sanitized_tools
@@ -378,35 +385,35 @@ class OpenAIResponsesAPIConfig(BaseResponsesAPIConfig):
             return item
         return {key: value for key, value in item.items() if key != "id"}  # mutable-ok: outgoing JSON request item
 
-    def _flatten_tool_schema_combinators_for_openai(
+    def _sanitized_tool_schemas_for_openai(
         self,
         model: str,
         tools: Sequence[ALL_RESPONSES_API_TOOL_PARAMS] | None,
         litellm_params: GenericLiteLLMParams,
     ) -> Sequence[ALL_RESPONSES_API_TOOL_PARAMS] | None:
-        """Flatten top-level schema combinators only where OpenAI's validator rejects them.
+        """Rewrite tool schemas only where OpenAI's validator rejects them.
 
-        OpenAI-compatible backends reusing this config (and the ChatGPT backend
-        Codex talks to natively) accept them, and so do GPT-5 and later models,
-        which also call tools better with the union intact. Codex wraps MCP tools
-        inside namespace entries, so nested ``tools`` arrays are walked too.
-        Azure OpenAI shares the validator but names deployments arbitrarily, so
-        the router's declared ``model_info.base_model`` wins over the deployment
-        name and an unrecognized name without one is left untouched.
+        Every model family refuses a ``pattern`` Python's ``re`` cannot compile,
+        while top-level schema combinators are flattened only for the families
+        whose validator rejects them: OpenAI-compatible backends reusing this
+        config (and the ChatGPT backend Codex talks to natively) accept them,
+        and so do GPT-5 and later models, which also call tools better with the
+        union intact. Codex wraps MCP tools inside namespace entries, so nested
+        ``tools`` arrays are walked too. Azure OpenAI shares the validator but
+        names deployments arbitrarily, so the router's declared
+        ``model_info.base_model`` wins over the deployment name and an
+        unrecognized name without one keeps its combinators.
         """
-        if tools is None or self.custom_llm_provider not in _PROVIDERS_WITH_COMBINATOR_REJECTING_VALIDATOR:
+        if tools is None or self.custom_llm_provider not in _PROVIDERS_WITH_OPENAI_SCHEMA_VALIDATOR:
             return tools
         gate_model: Final = self._combinator_gate_model(model=model, litellm_params=litellm_params)
-        if not self._rejects_top_level_schema_combinators(gate_model):
-            return tools
-        flattened: Final = [  # mutable-ok: request tools are a JSON list
-            self._flattened_tool_or_passthrough(tool) for tool in tools
-        ]
-        return cast("Sequence[ALL_RESPONSES_API_TOOL_PARAMS]", flattened)  # cast-ok: spread keeps each tool's shape
-
-    @staticmethod
-    def _flattened_tool_or_passthrough(tool: object) -> object:
-        return OpenAIResponsesAPIConfig._flattened_tool_entry(tool) if isinstance(tool, dict) else tool
+        sanitize: Final = (
+            flatten_combinators_and_drop_non_python_regex_patterns
+            if self._rejects_top_level_schema_combinators(gate_model)
+            else drop_non_python_regex_patterns
+        )
+        sanitized: Final = self._sanitized_tools(tools, sanitize)
+        return cast("Sequence[ALL_RESPONSES_API_TOOL_PARAMS]", sanitized)  # cast-ok: spread keeps each tool's shape
 
     @staticmethod
     def _rejects_top_level_schema_combinators(model: str) -> bool:
@@ -421,35 +428,42 @@ class OpenAIResponsesAPIConfig(BaseResponsesAPIConfig):
         return base_model if isinstance(base_model, str) and base_model else model
 
     @staticmethod
-    def _flattened_tool_entry(
+    def _sanitized_tool_entry(
         entry: Mapping[str, object],
-    ) -> dict[str, object]:  # mutable-ok: request tools are JSON dicts
-        from litellm.litellm_core_utils.prompt_templates.common_utils import (
-            flatten_top_level_schema_combinators,
-        )
-
+        sanitize: Callable[[Mapping[str, object]], Mapping[str, object]],
+    ) -> Mapping[str, object]:
         parameters: Final = entry.get("parameters")
         nested_tools: Final = entry.get("tools")
+        sanitized_parameters: Final = sanitize(parameters) if isinstance(parameters, dict) else parameters
+        sanitized_nested_tools: Final = (
+            OpenAIResponsesAPIConfig._sanitized_tools(nested_tools, sanitize)
+            if isinstance(nested_tools, list)
+            else nested_tools
+        )
         parameters_update: Final = (
-            MappingProxyType({"parameters": flatten_top_level_schema_combinators(parameters)})
-            if isinstance(parameters, dict)
+            MappingProxyType({"parameters": sanitized_parameters})
+            if sanitized_parameters is not parameters
             else _NO_TOOL_UPDATE
         )
         tools_update: Final = (
-            MappingProxyType({"tools": OpenAIResponsesAPIConfig._flattened_nested_tools(nested_tools)})
-            if isinstance(nested_tools, list)
+            MappingProxyType({"tools": sanitized_nested_tools})
+            if sanitized_nested_tools is not nested_tools
             else _NO_TOOL_UPDATE
         )
+        if not parameters_update and not tools_update:
+            return entry
         return {**entry, **parameters_update, **tools_update}  # mutable-ok: request tools are JSON dicts
 
     @staticmethod
-    def _flattened_nested_tools(
-        nested_tools: Sequence[object],
-    ) -> list[object]:  # mutable-ok: namespace tools are a JSON list
-        return [  # mutable-ok: namespace tools are a JSON list
-            OpenAIResponsesAPIConfig._flattened_tool_entry(item) if isinstance(item, dict) else item
-            for item in nested_tools
+    def _sanitized_tools(
+        tools: Sequence[object],
+        sanitize: Callable[[Mapping[str, object]], Mapping[str, object]],
+    ) -> Sequence[object]:
+        sanitized: Final = [  # mutable-ok: request tools are a JSON list
+            OpenAIResponsesAPIConfig._sanitized_tool_entry(item, sanitize) if isinstance(item, dict) else item
+            for item in tools
         ]
+        return tools if all(new is old for new, old in zip(sanitized, tools, strict=True)) else sanitized
 
     def _validate_input_param(self, input: str | ResponseInputParam) -> str | ResponseInputParam:
         """
@@ -620,15 +634,20 @@ class OpenAIResponsesAPIConfig(BaseResponsesAPIConfig):
             return event_pydantic_model.model_construct(**parsed_chunk)
 
     @staticmethod
-    def parse_terminal_response_from_stream_chunks(all_chunks: list[str]) -> ResponsesAPIResponse | None:
+    def parse_terminal_event_from_stream_chunks(all_chunks: Sequence[str]) -> ResponsesTerminalEvent | None:
         for chunk_str in reversed(all_chunks):
             for event_model in (ResponseCompletedEvent, ResponseIncompleteEvent, ResponseFailedEvent):
                 try:
-                    return event_model.model_validate_json(chunk_str.removeprefix("data: ")).response
+                    return event_model.model_validate_json(chunk_str.removeprefix("data: "))
                 except ValueError:
                     continue
         return None
 
+    @staticmethod
+    def parse_terminal_response_from_stream_chunks(all_chunks: list[str]) -> ResponsesAPIResponse | None:
+        terminal_event: Final = OpenAIResponsesAPIConfig.parse_terminal_event_from_stream_chunks(all_chunks)
+        return None if terminal_event is None else terminal_event.response
+
     @staticmethod
     def get_event_model_class(event_type: str) -> type[BaseLiteLLMOpenAIResponseObject]:
         """
diff --git a/litellm/llms/sagemaker/chat/handler.py b/litellm/llms/sagemaker/chat/handler.py
index 3f62b7276df..38978300c52 100644
--- a/litellm/llms/sagemaker/chat/handler.py
+++ b/litellm/llms/sagemaker/chat/handler.py
@@ -36,6 +36,7 @@ class SagemakerChatHandler(BaseAWSLLM):
         aws_web_identity_token: Final = optional_params.pop("aws_web_identity_token", None)
         aws_sts_endpoint: Final = optional_params.pop("aws_sts_endpoint", None)
         aws_external_id: Final = optional_params.pop("aws_external_id", None)
+        aws_session_tags: Final = optional_params.pop("aws_session_tags", None)
 
         ### SET REGION NAME ###
         if aws_region_name is None:
@@ -63,6 +64,7 @@ class SagemakerChatHandler(BaseAWSLLM):
             aws_web_identity_token=aws_web_identity_token,
             aws_sts_endpoint=aws_sts_endpoint,
             aws_external_id=aws_external_id,
+            aws_session_tags=aws_session_tags,
         )
         return credentials, aws_region_name
 
diff --git a/litellm/llms/sagemaker/completion/handler.py b/litellm/llms/sagemaker/completion/handler.py
index fb8074d3682..fad0a460647 100644
--- a/litellm/llms/sagemaker/completion/handler.py
+++ b/litellm/llms/sagemaker/completion/handler.py
@@ -59,6 +59,7 @@ class SagemakerLLM(BaseAWSLLM):
         aws_web_identity_token: Final = optional_params.pop("aws_web_identity_token", None)
         aws_sts_endpoint: Final = optional_params.pop("aws_sts_endpoint", None)
         aws_external_id: Final = optional_params.pop("aws_external_id", None)
+        aws_session_tags: Final = optional_params.pop("aws_session_tags", None)
 
         ### SET REGION NAME ###
         if aws_region_name is None:
@@ -86,6 +87,7 @@ class SagemakerLLM(BaseAWSLLM):
             aws_web_identity_token=aws_web_identity_token,
             aws_sts_endpoint=aws_sts_endpoint,
             aws_external_id=aws_external_id,
+            aws_session_tags=aws_session_tags,
         )
         return credentials, aws_region_name
 
diff --git a/litellm/llms/voyage/embedding/transformation_contextual.py b/litellm/llms/voyage/embedding/transformation_contextual.py
index ec77ce91d33..870de8756bb 100644
--- a/litellm/llms/voyage/embedding/transformation_contextual.py
+++ b/litellm/llms/voyage/embedding/transformation_contextual.py
@@ -3,6 +3,7 @@ This module is used to transform the request and response for the Voyage context
 This would be used for all the contextualized embeddings models in Voyage.
 """
 
+from collections.abc import Mapping
 from typing import Final
 
 import httpx
@@ -24,7 +25,10 @@ class VoyageError(BaseLLMException):
     ):
         self.status_code = status_code
         self.message = message
-        self.request = httpx.Request(method="POST", url="https://api.voyageai.com/v1/contextualizedembeddings")
+        self.request = httpx.Request(
+            method="POST",
+            url="https://api.voyageai.com/v1/contextualizedembeddings",
+        )
         self.response = httpx.Response(status_code=status_code, request=self.request)
         super().__init__(
             status_code=status_code,
@@ -56,16 +60,16 @@ class VoyageContextualEmbeddingConfig(BaseEmbeddingConfig):
             return api_base
         return "https://api.voyageai.com/v1/contextualizedembeddings"
 
-    def get_supported_openai_params(self, model: str) -> list:
+    def get_supported_openai_params(self, model: str) -> list:  # mutable-ok: base class signature
         return ["encoding_format", "dimensions"]
 
     def map_openai_params(
         self,
-        non_default_params: dict,
-        optional_params: dict,
+        non_default_params: dict,  # mutable-ok: base class signature
+        optional_params: dict,  # mutable-ok: base class signature
         model: str,
         drop_params: bool,
-    ) -> dict:
+    ) -> dict:  # mutable-ok: base class signature
         """
         Map OpenAI params to Voyage params
 
@@ -79,7 +83,7 @@ class VoyageContextualEmbeddingConfig(BaseEmbeddingConfig):
 
     def validate_environment(
         self,
-        headers: dict,
+        headers: dict,  # mutable-ok: base class signature
         model: str,
         messages: list[AllMessageValues],
         optional_params: dict,
@@ -97,6 +101,8 @@ class VoyageContextualEmbeddingConfig(BaseEmbeddingConfig):
             "Authorization": f"Bearer {api_key}",
         }
 
+    AUTO_CHUNK_SIZE: Final = 32000
+
     def transform_embedding_request(
         self,
         model: str,
@@ -105,11 +111,27 @@ class VoyageContextualEmbeddingConfig(BaseEmbeddingConfig):
         headers: dict,
     ) -> dict:
         return {
-            "inputs": input,
+            "inputs": [input] if isinstance(input, str) else input,
             "model": model,
+            **self._auto_chunk_params(input, optional_params),
             **optional_params,
         }
 
+    @classmethod
+    def _auto_chunk_params(
+        cls,
+        input: AllEmbeddingInputValues | list[list[str]],
+        optional_params: Mapping[str, object],
+    ) -> Mapping[str, object]:
+        is_flat: Final = isinstance(input, str) or all(isinstance(item, str) for item in input)
+        if not is_flat or optional_params.get("input_type") == "query":
+            return {}
+        return {
+            "enable_auto_chunking": True,
+            "chunk_size": cls.AUTO_CHUNK_SIZE,
+            "input_type": "document",
+        }
+
     def transform_embedding_response(
         self,
         model: str,
@@ -124,9 +146,11 @@ class VoyageContextualEmbeddingConfig(BaseEmbeddingConfig):
         try:
             raw_response_json: Final = raw_response.json()
         except Exception:
-            raise VoyageError(message=raw_response.text, status_code=raw_response.status_code)
+            raise VoyageError(
+                message=raw_response.text,
+                status_code=raw_response.status_code,
+            )
 
-        # model_response.usage
         model_response.model = raw_response_json.get("model")
         model_response.data = raw_response_json.get("data")
         model_response.object = raw_response_json.get("object")
diff --git a/litellm/llms/wandb/chat/transformation.py b/litellm/llms/wandb/chat/transformation.py
index a477c00f643..fdd6644f03d 100644
--- a/litellm/llms/wandb/chat/transformation.py
+++ b/litellm/llms/wandb/chat/transformation.py
@@ -6,10 +6,17 @@ This is OpenAI compatible - no translation needed / occurs
 
 from typing import Final
 
+import litellm
 from litellm.llms.openai.chat.gpt_transformation import OpenAIGPTConfig
 
 
 class WandbConfig(OpenAIGPTConfig):
+    def get_supported_openai_params(self, model: str) -> list[str]:  # mutable-ok: inherited contract
+        supported_params: Final = super().get_supported_openai_params(model)
+        if litellm.supports_reasoning(model=model, custom_llm_provider="wandb"):
+            return supported_params + ["reasoning_effort"]  # mutable-ok: inherited contract
+        return supported_params
+
     def map_openai_params(
         self,
         non_default_params: dict,
diff --git a/litellm/main.py b/litellm/main.py
index 56f9cb2c0d0..17edafcdfca 100644
--- a/litellm/main.py
+++ b/litellm/main.py
@@ -19,7 +19,7 @@ import random
 import sys
 import time
 import traceback
-from collections.abc import AsyncIterator, Coroutine, Iterable, Mapping, Sequence
+from collections.abc import AsyncIterator, Callable, Coroutine, Iterable, Mapping, Sequence
 from concurrent import futures
 from concurrent.futures import FIRST_COMPLETED, ThreadPoolExecutor, wait
 from copy import deepcopy
@@ -827,6 +827,35 @@ async def _sleep_for_timeout_async(timeout: float | str | httpx.Timeout):
         await asyncio.sleep(timeout.connect)
 
 
+class _AdmissionReservation(BaseModel):
+    input_tokens: int | None = None
+
+
+class _AdmissionMetadata(BaseModel):
+    user_api_key_budget_reservation: _AdmissionReservation | None = None
+
+
+def admission_input_tokens(kwargs: Mapping[str, object]) -> int | None:
+    reservations: Final = (
+        _AdmissionMetadata.model_validate(kwargs.get(key) or {}).user_api_key_budget_reservation
+        for key in ("litellm_metadata", "metadata")
+    )
+    return next(
+        (
+            reservation.input_tokens
+            for reservation in reservations
+            if reservation and reservation.input_tokens is not None
+        ),
+        None,
+    )
+
+
+def admitted_prompt_token_counter(prompt_tokens: int | None) -> Callable[[], int] | None:
+    if prompt_tokens is None:
+        return None
+    return lambda: prompt_tokens
+
+
 def mock_completion(
     model: str,
     messages: list,
@@ -838,6 +867,7 @@ def mock_completion(
     logging=None,
     custom_llm_provider=None,
     timeout: float | str | httpx.Timeout | None = None,
+    prompt_tokens: int | None = None,
     **kwargs,
 ):
     """
@@ -911,23 +941,26 @@ def mock_completion(
 
         if stream is True:
             model_response = ModelResponseStream()
+            count_prompt_tokens: Final = admitted_prompt_token_counter(prompt_tokens)
             # don't try to access stream object,
             if kwargs.get("acompletion", False) is True:
                 return CustomStreamWrapper(
                     completion_stream=async_mock_completion_streaming_obj(
-                        model_response, mock_response=mock_response, model=model, n=n
+                        model_response, mock_response=mock_response, model=model, n=n, prompt_tokens=prompt_tokens
                     ),
                     model=model,
                     custom_llm_provider="openai",
                     logging_obj=logging,
+                    count_prompt_tokens=count_prompt_tokens,
                 )
             return CustomStreamWrapper(
                 completion_stream=mock_completion_streaming_obj(
-                    model_response, mock_response=mock_response, model=model, n=n
+                    model_response, mock_response=mock_response, model=model, n=n, prompt_tokens=prompt_tokens
                 ),
                 model=model,
                 custom_llm_provider="openai",
                 logging_obj=logging,
+                count_prompt_tokens=count_prompt_tokens,
             )
         if isinstance(mock_response, litellm.MockException):
             raise mock_response
@@ -953,13 +986,16 @@ def mock_completion(
                 ChatCompletionMessageToolCall(**tool_call) for tool_call in mock_tool_calls
             ]
 
+        usage_prompt_tokens: Final = (
+            prompt_tokens if prompt_tokens is not None else DEFAULT_MOCK_RESPONSE_PROMPT_TOKEN_COUNT
+        )
         setattr(
             model_response,
             "usage",
             Usage(
-                prompt_tokens=DEFAULT_MOCK_RESPONSE_PROMPT_TOKEN_COUNT,
+                prompt_tokens=usage_prompt_tokens,
                 completion_tokens=DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
-                total_tokens=DEFAULT_MOCK_RESPONSE_PROMPT_TOKEN_COUNT + DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
+                total_tokens=usage_prompt_tokens + DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
             ),
         )
 
@@ -5398,6 +5434,14 @@ def completion(
         if dynamic_api_key is not None:
             api_key = dynamic_api_key
         # check if user passed in any of the OpenAI optional params
+        bridges_to_responses_api: Final = (
+            responses_api_model_info.get("mode") == "responses" and not skip_responses_api_bridge
+        )
+        allowed_openai_params: Final[list[str] | None] = (
+            [*(kwargs.get("allowed_openai_params") or []), "reasoning_effort"]
+            if bridges_to_responses_api
+            else kwargs.get("allowed_openai_params")
+        )
         optional_param_args: Final = {
             "functions": functions,
             "function_call": function_call,
@@ -5442,7 +5486,7 @@ def completion(
             "service_tier": service_tier,
             "store": store,
             "prompt_cache_key": prompt_cache_key,
-            "allowed_openai_params": kwargs.get("allowed_openai_params"),
+            "allowed_openai_params": allowed_openai_params,
             "base_model": base_model,
         }
         optional_params = get_optional_params(**optional_param_args, **non_default_params)
@@ -5542,6 +5586,9 @@ def completion(
                 custom_llm_provider=custom_llm_provider,
                 mock_timeout=mock_timeout,
                 timeout=timeout,
+                prompt_tokens=admission_input_tokens(
+                    cast(Mapping[str, object], kwargs)  # cast-ok: completion's **kwargs is untyped
+                ),
             )
 
         ## RESPONSES API BRIDGE LOGIC ## - check if model has 'mode: responses' in litellm.model_cost map
@@ -7805,6 +7852,7 @@ def transcription(
             azure_ad_token=azure_ad_token,
             max_retries=max_retries,
             litellm_params=litellm_params_dict,
+            custom_llm_provider=custom_llm_provider,
         )
     elif custom_llm_provider == "openai" or (custom_llm_provider in litellm.openai_compatible_providers):
         api_base = (
@@ -8586,7 +8634,7 @@ def config_completion(**kwargs):
         )
 
 
-def stream_chunk_builder_text_completion(chunks: list, messages: list | None = None) -> TextCompletionResponse:
+def stream_chunk_builder_text_completion(chunks: list, messages: Sequence | None = None) -> TextCompletionResponse:
     id: Final = chunks[0]["id"]
     object: Final = chunks[0]["object"]
     created: Final = chunks[0]["created"]
@@ -8703,10 +8751,11 @@ def _stamp_streaming_usage_cost(usage: Usage, response: ModelResponse, logging_o
 
 def stream_chunk_builder(
     chunks: list,
-    messages: list | None = None,
+    messages: Sequence | None = None,
     start_time=None,
     end_time=None,
     logging_obj: Optional["Logging"] = None,
+    count_prompt_tokens: Callable[[], int] | None = None,
 ) -> ModelResponse | TextCompletionResponse | None:
     try:
         if chunks is None:
@@ -8780,6 +8829,7 @@ def stream_chunk_builder(
                 completion_output=completion_output,
                 messages=messages,
                 reasoning_tokens=0,
+                count_prompt_tokens=count_prompt_tokens,
             )
             setattr(response, "usage", usage)
 
@@ -8957,6 +9007,7 @@ def stream_chunk_builder(
             completion_output=completion_output,
             messages=messages,
             reasoning_tokens=reasoning_tokens,
+            count_prompt_tokens=count_prompt_tokens,
         )
 
         setattr(response, "usage", usage)
diff --git a/litellm/model_prices_and_context_window_backup.json b/litellm/model_prices_and_context_window_backup.json
index 7784ed2a6ac..b7726290f0e 100644
--- a/litellm/model_prices_and_context_window_backup.json
+++ b/litellm/model_prices_and_context_window_backup.json
@@ -364,7 +364,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "amazon.nova-2-lite-v1:0": {
         "cache_read_input_token_cost": 7.5e-08,
@@ -380,6 +381,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -399,6 +401,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -416,6 +419,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -435,6 +439,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -452,6 +457,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -471,6 +477,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -488,6 +495,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -507,6 +515,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -537,7 +546,8 @@
         "output_cost_per_token": 1.4e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "amazon.nova-pro-v1:0": {
         "input_cost_per_token": 8e-07,
@@ -551,7 +561,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "amazon.nova-sonic-v1:0": {
         "deprecation_date": "2026-09-14",
@@ -756,6 +767,14 @@
         "mode": "chat",
         "supports_video_input": true
     },
+    "global.twelvelabs.pegasus-1-2-v1:0": {
+        "input_cost_per_video_per_second": 0.00049,
+        "output_cost_per_token": 7.5e-06,
+        "litellm_provider": "bedrock",
+        "mode": "chat",
+        "supports_video_input": true,
+        "source": "https://aws.amazon.com/bedrock/pricing/"
+    },
     "amazon.titan-text-express-v1": {
         "input_cost_per_token": 1.3e-06,
         "litellm_provider": "bedrock",
@@ -2876,7 +2895,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "apac.amazon.nova-micro-v1:0": {
         "input_cost_per_token": 3.7e-08,
@@ -2888,7 +2908,8 @@
         "output_cost_per_token": 1.48e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "apac.amazon.nova-pro-v1:0": {
         "input_cost_per_token": 8.4e-07,
@@ -2902,7 +2923,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "apac.anthropic.claude-3-5-sonnet-20240620-v1:0": {
         "deprecation_date": "2026-07-30",
@@ -3626,6 +3648,79 @@
         "supports_xhigh_reasoning_effort": true,
         "supports_minimal_reasoning_effort": false
     },
+    "azure_ai/gpt-chat-latest": {
+        "cache_read_input_token_cost": 5e-07,
+        "deprecation_date": "2026-12-02",
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 272000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "output_cost_per_token": 3e-05,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/cognitive-services/openai-service/",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_native_streaming": true,
+        "supports_parallel_function_calling": true,
+        "supports_pdf_input": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_system_messages": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "supports_web_search": true
+    },
+    "azure_ai/codex-mini": {
+        "cache_read_input_token_cost": 3.75e-07,
+        "deprecation_date": "2026-11-15",
+        "input_cost_per_token": 1.5e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 100000,
+        "max_tokens": 100000,
+        "mode": "responses",
+        "output_cost_per_token": 6e-06,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/cognitive-services/openai-service/",
+        "supported_endpoints": [
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_pdf_input": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_system_messages": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
+    "azure_ai/whisper": {
+        "deprecation_date": "2026-12-15",
+        "input_cost_per_second": 0.0001,
+        "litellm_provider": "azure_ai",
+        "mode": "audio_transcription",
+        "output_cost_per_second": 0.0001,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/cognitive-services/openai-service/"
+    },
     "azure_ai/gpt-5.5-2026-04-23": {
         "cache_read_input_token_cost": 5e-07,
         "cache_read_input_token_cost_above_272k_tokens": 1e-06,
@@ -4029,13 +4124,29 @@
         "supports_minimal_reasoning_effort": false
     },
     "azure_ai/model_router": {
+        "deprecation_date": "2027-05-20",
         "input_cost_per_token": 1.4e-07,
         "output_cost_per_token": 0,
         "litellm_provider": "azure_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
         "mode": "chat",
         "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/aoai/",
         "comment": "Flat cost of $0.14 per M input tokens for Azure AI Foundry Model Router infrastructure. Use pattern: azure_ai/model_router/<deployment-name> where deployment-name is your Azure deployment (e.g., azure-model-router)"
     },
+    "azure_ai/model-router": {
+        "deprecation_date": "2027-05-20",
+        "input_cost_per_token": 1.4e-07,
+        "output_cost_per_token": 0,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
+        "mode": "chat",
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/aoai/",
+        "comment": "Catalog-name twin of azure_ai/model_router: the flat $0.14 per M input tokens is the router's own fee, the routed model is priced on top of it"
+    },
     "azure/eu/gpt-4o-2024-08-06": {
         "deprecation_date": "2027-04-14",
         "cache_read_input_token_cost": 1.375e-06,
@@ -7975,7 +8086,8 @@
         "supports_system_messages": true,
         "supports_tool_choice": true,
         "supports_vision": true,
-        "supports_web_search": true
+        "supports_web_search": true,
+        "deprecation_date": "2027-10-26"
     },
     "azure/us/gpt-5.5-2026-04-23": {
         "cache_read_input_token_cost": 5.5e-07,
@@ -8019,7 +8131,8 @@
         "supports_system_messages": true,
         "supports_tool_choice": true,
         "supports_vision": true,
-        "supports_web_search": true
+        "supports_web_search": true,
+        "deprecation_date": "2027-10-26"
     },
     "azure/eu/gpt-5.5-2026-04-23": {
         "cache_read_input_token_cost": 5.5e-07,
@@ -8063,7 +8176,8 @@
         "supports_system_messages": true,
         "supports_tool_choice": true,
         "supports_vision": true,
-        "supports_web_search": true
+        "supports_web_search": true,
+        "deprecation_date": "2027-10-26"
     },
     "azure/gpt-5.5-pro": {
         "cache_read_input_token_cost": 3e-06,
@@ -10347,6 +10461,18 @@
             "/v1/ocr"
         ]
     },
+    "azure_ai/cohere-command-a": {
+        "input_cost_per_token": 2.5e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 131072,
+        "max_output_tokens": 8182,
+        "max_tokens": 8182,
+        "mode": "chat",
+        "output_cost_per_token": 1e-05,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/cohere/",
+        "supports_function_calling": true,
+        "supports_tool_choice": true
+    },
     "azure_ai/doc-intelligence/prebuilt-read": {
         "litellm_provider": "azure_ai",
         "ocr_cost_per_page": 0.0015,
@@ -10698,6 +10824,41 @@
         "supports_vision": true,
         "supports_web_search": true
     },
+    "azure_ai/grok-4-20-reasoning": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "deprecation_date": "2027-04-06",
+        "input_cost_per_token": 1.25e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 262000,
+        "max_output_tokens": 8192,
+        "max_tokens": 8192,
+        "mode": "chat",
+        "output_cost_per_token": 2.5e-06,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/grok/",
+        "supports_function_calling": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "supports_web_search": true,
+        "supports_reasoning": true
+    },
+    "azure_ai/grok-4-20-non-reasoning": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "deprecation_date": "2027-04-06",
+        "input_cost_per_token": 1.25e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 262000,
+        "max_output_tokens": 8192,
+        "max_tokens": 8192,
+        "mode": "chat",
+        "output_cost_per_token": 2.5e-06,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/grok/",
+        "supports_function_calling": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "supports_web_search": true
+    },
     "azure_ai/grok-4-fast-non-reasoning": {
         "deprecation_date": "2026-05-01",
         "input_cost_per_token": 2e-07,
@@ -12181,7 +12342,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-east-1/amazon.titan-embed-text-v1": {
         "input_cost_per_token": 1e-07,
@@ -12360,7 +12522,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-west-1/amazon.nova-micro-v1:0": {
         "input_cost_per_token": 4.2e-08,
@@ -12372,7 +12535,8 @@
         "output_cost_per_token": 1.68e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-west-1/amazon.nova-pro-v1:0": {
         "input_cost_per_token": 9.6e-07,
@@ -12386,7 +12550,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-west-1/amazon.titan-embed-text-v1": {
         "input_cost_per_token": 1e-07,
@@ -13837,7 +14002,8 @@
         "max_output_tokens": 3072,
         "max_tokens": 3072,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-2-7b-chat-int8": {
         "input_cost_per_token": 1.923e-06,
@@ -13846,7 +14012,8 @@
         "max_output_tokens": 2048,
         "max_tokens": 2048,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/mistral/mistral-7b-instruct-v0.1": {
         "input_cost_per_token": 1.923e-06,
@@ -13855,7 +14022,8 @@
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@hf/thebloke/codellama-7b-instruct-awq": {
         "input_cost_per_token": 1.923e-06,
@@ -13864,7 +14032,8 @@
         "max_output_tokens": 4096,
         "max_tokens": 4096,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/openai/gpt-oss-120b": {
         "input_cost_per_token": 3.5e-07,
@@ -13874,6 +14043,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 7.5e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13884,7 +14054,8 @@
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-3.2-3b-instruct": {
         "input_cost_per_token": 5.09e-08,
@@ -13893,7 +14064,8 @@
         "max_output_tokens": 80000,
         "max_tokens": 80000,
         "mode": "chat",
-        "output_cost_per_token": 3.35e-07
+        "output_cost_per_token": 3.35e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-guard-3-8b": {
         "input_cost_per_token": 4.84e-07,
@@ -13902,7 +14074,8 @@
         "max_output_tokens": 131072,
         "max_tokens": 131072,
         "mode": "chat",
-        "output_cost_per_token": 3e-08
+        "output_cost_per_token": 3e-08,
+        "rpm": 300
     },
     "cloudflare/@cf/mistral/mistral-7b-instruct-v0.2-lora": {
         "input_cost_per_token": 0.0,
@@ -13911,7 +14084,8 @@
         "max_output_tokens": 15000,
         "max_tokens": 15000,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/moonshotai/kimi-k2.7-code": {
         "cache_read_input_token_cost": 1.9e-07,
@@ -13922,6 +14096,7 @@
         "max_tokens": 262144,
         "mode": "chat",
         "output_cost_per_token": 4e-06,
+        "rpm": 20,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13933,6 +14108,7 @@
         "max_tokens": 80000,
         "mode": "chat",
         "output_cost_per_token": 4.881e-06,
+        "rpm": 300,
         "supports_reasoning": true
     },
     "cloudflare/@cf/meta/llama-3.1-8b-instruct-fp8": {
@@ -13942,7 +14118,8 @@
         "max_output_tokens": 32000,
         "max_tokens": 32000,
         "mode": "chat",
-        "output_cost_per_token": 2.87e-07
+        "output_cost_per_token": 2.87e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-3.2-1b-instruct": {
         "input_cost_per_token": 2.7e-08,
@@ -13951,7 +14128,8 @@
         "max_output_tokens": 60000,
         "max_tokens": 60000,
         "mode": "chat",
-        "output_cost_per_token": 2.01e-07
+        "output_cost_per_token": 2.01e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/moonshotai/kimi-k2.6": {
         "cache_read_input_token_cost": 1.6e-07,
@@ -13962,6 +14140,7 @@
         "max_tokens": 262144,
         "mode": "chat",
         "output_cost_per_token": 4e-06,
+        "rpm": 20,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13973,6 +14152,7 @@
         "max_tokens": 131072,
         "mode": "chat",
         "output_cost_per_token": 4e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13983,7 +14163,8 @@
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-3.3-70b-instruct-fp8-fast": {
         "input_cost_per_token": 2.93e-07,
@@ -13993,6 +14174,7 @@
         "max_tokens": 24000,
         "mode": "chat",
         "output_cost_per_token": 2.253e-06,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/ibm-granite/granite-4.0-h-micro": {
@@ -14003,6 +14185,7 @@
         "max_tokens": 131000,
         "mode": "chat",
         "output_cost_per_token": 1.12e-07,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/qwen/qwen2.5-coder-32b-instruct": {
@@ -14012,7 +14195,8 @@
         "max_output_tokens": 32768,
         "max_tokens": 32768,
         "mode": "chat",
-        "output_cost_per_token": 1e-06
+        "output_cost_per_token": 1e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/zai-org/glm-5.2": {
         "cache_read_input_token_cost": 2.6e-07,
@@ -14023,6 +14207,7 @@
         "max_tokens": 262144,
         "mode": "chat",
         "output_cost_per_token": 4.4e-06,
+        "rpm": 20,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14034,6 +14219,7 @@
         "max_tokens": 256000,
         "mode": "chat",
         "output_cost_per_token": 1.5e-06,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14044,7 +14230,8 @@
         "max_output_tokens": 128000,
         "max_tokens": 128000,
         "mode": "chat",
-        "output_cost_per_token": 5.55e-07
+        "output_cost_per_token": 5.55e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/qwen/qwen3-30b-a3b-fp8": {
         "input_cost_per_token": 5.09e-08,
@@ -14054,6 +14241,7 @@
         "max_tokens": 32768,
         "mode": "chat",
         "output_cost_per_token": 3.35e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14064,7 +14252,8 @@
         "max_output_tokens": 3500,
         "max_tokens": 3500,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/google/gemma-4-26b-a4b-it": {
         "input_cost_per_token": 1e-07,
@@ -14074,6 +14263,7 @@
         "max_tokens": 256000,
         "mode": "chat",
         "output_cost_per_token": 3e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14085,6 +14275,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 5.55e-07,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/meta/llama-3.2-11b-vision-instruct": {
@@ -14095,6 +14286,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 6.76e-07,
+        "rpm": 300,
         "supports_vision": true
     },
     "cloudflare/@cf/openai/gpt-oss-20b": {
@@ -14105,6 +14297,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 3e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14116,6 +14309,7 @@
         "max_tokens": 131000,
         "mode": "chat",
         "output_cost_per_token": 8.5e-07,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/qwen/qwq-32b": {
@@ -14126,6 +14320,7 @@
         "max_tokens": 24000,
         "mode": "chat",
         "output_cost_per_token": 1e-06,
+        "rpm": 300,
         "supports_reasoning": true
     },
     "codestral/codestral-2405": {
@@ -14252,6 +14447,28 @@
         "output_vector_size": 1536,
         "supports_embedding_image_input": true
     },
+    "us.cohere.embed-v4:0": {
+        "input_cost_per_token": 1.2e-07,
+        "litellm_provider": "bedrock",
+        "max_input_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "embedding",
+        "output_cost_per_token": 0.0,
+        "output_vector_size": 1536,
+        "supports_embedding_image_input": true,
+        "source": "https://aws.amazon.com/bedrock/pricing/"
+    },
+    "global.cohere.embed-v4:0": {
+        "input_cost_per_token": 1.2e-07,
+        "litellm_provider": "bedrock",
+        "max_input_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "embedding",
+        "output_cost_per_token": 0.0,
+        "output_vector_size": 1536,
+        "supports_embedding_image_input": true,
+        "source": "https://aws.amazon.com/bedrock/pricing/"
+    },
     "cohere/embed-v4.0": {
         "input_cost_per_token": 1.2e-07,
         "litellm_provider": "cohere",
@@ -20823,7 +21040,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "eu.amazon.nova-micro-v1:0": {
         "input_cost_per_token": 4.6e-08,
@@ -20835,7 +21053,8 @@
         "output_cost_per_token": 1.84e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "eu.amazon.nova-pro-v1:0": {
         "input_cost_per_token": 1.05e-06,
@@ -20850,24 +21069,25 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "eu.anthropic.claude-3-5-haiku-20241022-v1:0": {
-        "input_cost_per_token": 2.5e-07,
+        "input_cost_per_token": 8e-07,
         "litellm_provider": "bedrock",
         "max_input_tokens": 200000,
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 1.25e-06,
+        "output_cost_per_token": 4e-06,
         "supports_assistant_prefill": true,
         "supports_function_calling": true,
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
         "supports_tool_choice": true,
-        "cache_read_input_token_cost": 2.5e-08,
-        "cache_creation_input_token_cost": 3.125e-07,
+        "cache_read_input_token_cost": 8e-08,
+        "cache_creation_input_token_cost": 1e-06,
         "prompt_cache_min_tokens": 2048
     },
     "eu.anthropic.claude-haiku-4-5-20251001-v1:0": {
@@ -23874,9 +24094,9 @@
         "input_cost_per_audio_token": 3e-06,
         "input_cost_per_token": 5e-07,
         "litellm_provider": "vertex_ai-language-models",
-        "max_input_tokens": 1048576,
-        "max_output_tokens": 65535,
-        "max_tokens": 65535,
+        "max_input_tokens": 131072,
+        "max_output_tokens": 65536,
+        "max_tokens": 65536,
         "mode": "realtime",
         "output_cost_per_audio_token": 1.2e-05,
         "output_cost_per_token": 2e-06,
@@ -23899,12 +24119,12 @@
         "supports_audio_output": true,
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
-        "supports_pdf_input": true,
-        "supports_prompt_caching": true,
-        "supports_response_schema": true,
+        "supports_pdf_input": false,
+        "supports_prompt_caching": false,
+        "supports_response_schema": false,
         "supports_system_messages": true,
         "supports_tool_choice": true,
-        "supports_url_context": true,
+        "supports_url_context": false,
         "supports_vision": true,
         "supports_web_search": true,
         "search_context_cost_per_query": {
@@ -27696,6 +27916,70 @@
         "max_tokens": 8191,
         "mode": "embedding"
     },
+    "chatgpt/gpt-5.5": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.5",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
+    "chatgpt/gpt-5.6-luna": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.6-luna",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
+    "chatgpt/gpt-5.6-sol": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.6-sol",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
+    "chatgpt/gpt-5.6-terra": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.6-terra",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
     "chatgpt/gpt-5.4": {
         "litellm_provider": "chatgpt",
         "max_input_tokens": 1050000,
@@ -28302,6 +28586,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -29126,7 +29411,12 @@
         "supports_response_schema": true,
         "supports_system_messages": true,
         "supports_tool_choice": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "search_context_cost_per_query": {
+            "search_context_size_high": 0.025,
+            "search_context_size_low": 0.025,
+            "search_context_size_medium": 0.025
+        }
     },
     "gpt-4o-mini-2024-07-18": {
         "cache_read_input_token_cost": 7.5e-08,
@@ -29143,9 +29433,9 @@
         "output_cost_per_token_priority": 1e-06,
         "output_cost_per_token_batches": 3e-07,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.03,
+            "search_context_size_high": 0.025,
             "search_context_size_low": 0.025,
-            "search_context_size_medium": 0.0275
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29244,9 +29534,9 @@
         "output_cost_per_token": 6e-07,
         "output_cost_per_token_batches": 3e-07,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.03,
+            "search_context_size_high": 0.025,
             "search_context_size_low": 0.025,
-            "search_context_size_medium": 0.0275
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29271,9 +29561,9 @@
         "output_cost_per_token": 6e-07,
         "output_cost_per_token_batches": 3e-07,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.03,
+            "search_context_size_high": 0.025,
             "search_context_size_low": 0.025,
-            "search_context_size_medium": 0.0275
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29384,9 +29674,9 @@
         "output_cost_per_token": 1e-05,
         "output_cost_per_token_batches": 5e-06,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.05,
-            "search_context_size_low": 0.03,
-            "search_context_size_medium": 0.035
+            "search_context_size_high": 0.025,
+            "search_context_size_low": 0.025,
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29411,9 +29701,9 @@
         "output_cost_per_token": 1e-05,
         "output_cost_per_token_batches": 5e-06,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.05,
-            "search_context_size_low": 0.03,
-            "search_context_size_medium": 0.035
+            "search_context_size_high": 0.025,
+            "search_context_size_low": 0.025,
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29495,6 +29785,66 @@
         "supports_vision": true,
         "supports_pdf_input": true
     },
+    "gpt-image-2.5-flare": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
+    "gpt-image-2.5-flare-2026-09-08": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
+    "gpt-image-2.5-sunburst": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
+    "gpt-image-2.5-sunburst-2026-09-08": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
     "low/1024-x-1024/gpt-image-1.5": {
         "deprecation_date": "2026-12-01",
         "input_cost_per_image": 0.009,
@@ -29945,7 +30295,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": false,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.1-2025-11-13": {
         "cache_read_input_token_cost": 1.25e-07,
@@ -29990,7 +30340,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": false,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.1-chat-latest": {
         "cache_read_input_token_cost": 1.25e-07,
@@ -30082,7 +30432,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.2-2025-12-11": {
         "cache_read_input_token_cost": 1.75e-07,
@@ -30128,7 +30478,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.2-chat-latest": {
         "cache_read_input_token_cost": 1.75e-07,
@@ -31124,7 +31474,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 2.5e-06,
         "output_cost_per_token_above_272k_tokens_flex": 1.125e-05,
         "cache_read_input_token_cost_above_272k_tokens_flex": 2.5e-07
@@ -31176,7 +31526,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 2.5e-06,
         "output_cost_per_token_above_272k_tokens_flex": 1.125e-05,
         "cache_read_input_token_cost_above_272k_tokens_flex": 2.5e-07
@@ -31228,7 +31578,7 @@
         "supports_web_search": true,
         "supports_none_reasoning_effort": false,
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 3e-05,
         "output_cost_per_token_above_272k_tokens_flex": 0.000135
     },
@@ -31279,7 +31629,7 @@
         "supports_web_search": true,
         "supports_none_reasoning_effort": false,
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 3e-05,
         "output_cost_per_token_above_272k_tokens_flex": 0.000135
     },
@@ -33359,13 +33709,14 @@
         "supports_tool_choice": true
     },
     "jina-reranker-v2-base-multilingual": {
-        "input_cost_per_token": 1.8e-08,
+        "input_cost_per_token": 5e-08,
         "litellm_provider": "jina_ai",
         "max_input_tokens": 1024,
         "max_output_tokens": 1024,
         "max_tokens": 1024,
         "mode": "rerank",
-        "output_cost_per_token": 1.8e-08
+        "output_cost_per_token": 0.0,
+        "source": "https://api.jina.ai/v1/models"
     },
     "jp.anthropic.claude-sonnet-4-5-20250929-v1:0": {
         "cache_creation_input_token_cost": 4.125e-06,
@@ -39619,6 +39970,45 @@
         "supports_tool_choice": true,
         "supports_vision": true
     },
+    "openrouter/openai/gpt-5.6-sol": {
+        "cache_creation_input_token_cost": 2.5e-06,
+        "cache_creation_input_token_cost_above_272k_tokens": 5e-06,
+        "cache_read_input_token_cost": 2e-07,
+        "cache_read_input_token_cost_above_272k_tokens": 4e-07,
+        "default_reasoning_effort": "medium",
+        "input_cost_per_token": 2e-06,
+        "input_cost_per_token_above_272k_tokens": 4e-06,
+        "litellm_provider": "openrouter",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "output_cost_per_token": 1e-05,
+        "output_cost_per_token_above_272k_tokens": 1.5e-05,
+        "reasoning_effort_levels": [
+            "none",
+            "low",
+            "medium",
+            "high",
+            "xhigh",
+            "max"
+        ],
+        "source": "https://openrouter.ai/openai/gpt-5.6-sol",
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_pdf_input": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
     "openrouter/openai/gpt-oss-120b": {
         "input_cost_per_token": 3.7e-08,
         "litellm_provider": "openrouter",
@@ -41575,6 +41965,28 @@
         "mode": "rerank",
         "output_cost_per_token": 0.0
     },
+    "rerank-v4.0-fast": {
+        "input_cost_per_query": 0.002,
+        "input_cost_per_token": 0.0,
+        "litellm_provider": "cohere",
+        "max_input_tokens": 32768,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
+        "mode": "rerank",
+        "output_cost_per_token": 0.0,
+        "source": "https://cohere.com/pricing"
+    },
+    "rerank-v4.0-pro": {
+        "input_cost_per_query": 0.0025,
+        "input_cost_per_token": 0.0,
+        "litellm_provider": "cohere",
+        "max_input_tokens": 32768,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
+        "mode": "rerank",
+        "output_cost_per_token": 0.0,
+        "source": "https://cohere.com/pricing"
+    },
     "nvidia_nim/nvidia/nv-rerankqa-mistral-4b-v3": {
         "input_cost_per_query": 0.0,
         "input_cost_per_token": 0.0,
@@ -43535,7 +43947,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "us.amazon.nova-micro-v1:0": {
         "input_cost_per_token": 3.5e-08,
@@ -43547,7 +43960,8 @@
         "output_cost_per_token": 1.4e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "us.amazon.nova-premier-v1:0": {
         "deprecation_date": "2026-09-14",
@@ -43576,7 +43990,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "us.anthropic.claude-3-5-haiku-20241022-v1:0": {
         "cache_creation_input_token_cost": 1e-06,
@@ -45755,8 +46170,8 @@
         "input_cost_per_token": 1e-06,
         "litellm_provider": "vertex_ai-anthropic_models",
         "max_input_tokens": 200000,
-        "max_output_tokens": 8192,
-        "max_tokens": 8192,
+        "max_output_tokens": 64000,
+        "max_tokens": 64000,
         "mode": "chat",
         "output_cost_per_token": 5e-06,
         "regional_endpoint_uplift_multiplier": 1.1,
@@ -45780,8 +46195,8 @@
         "input_cost_per_token": 1e-06,
         "litellm_provider": "vertex_ai-anthropic_models",
         "max_input_tokens": 200000,
-        "max_output_tokens": 8192,
-        "max_tokens": 8192,
+        "max_output_tokens": 64000,
+        "max_tokens": 64000,
         "mode": "chat",
         "output_cost_per_token": 5e-06,
         "regional_endpoint_uplift_multiplier": 1.1,
@@ -47761,9 +48176,9 @@
         "cache_read_input_token_cost": 5e-08,
         "input_cost_per_token": 2e-07,
         "litellm_provider": "vertex_ai",
-        "max_input_tokens": 2000000,
-        "max_output_tokens": 2000000,
-        "max_tokens": 2000000,
+        "max_input_tokens": 128000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 5e-07,
         "source": "https://docs.x.ai/developers/models",
@@ -47777,9 +48192,9 @@
         "cache_read_input_token_cost": 5e-08,
         "input_cost_per_token": 2e-07,
         "litellm_provider": "vertex_ai",
-        "max_input_tokens": 2000000,
-        "max_output_tokens": 2000000,
-        "max_tokens": 2000000,
+        "max_input_tokens": 128000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 5e-07,
         "source": "https://docs.x.ai/developers/models",
@@ -47792,14 +48207,17 @@
     },
     "vertex_ai/xai/grok-4.20-non-reasoning": {
         "cache_read_input_token_cost": 2e-07,
-        "input_cost_per_token": 2e-06,
+        "cache_read_input_token_cost_above_200k_tokens": 4e-07,
+        "input_cost_per_token": 1.25e-06,
+        "input_cost_per_token_above_200k_tokens": 2.5e-06,
         "litellm_provider": "vertex_ai",
         "max_input_tokens": 2000000,
         "max_output_tokens": 2000000,
         "max_tokens": 2000000,
         "mode": "chat",
-        "output_cost_per_token": 6e-06,
-        "source": "https://docs.x.ai/developers/models",
+        "output_cost_per_token": 2.5e-06,
+        "output_cost_per_token_above_200k_tokens": 5e-06,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
         "supports_function_calling": true,
         "supports_response_schema": true,
         "supports_tool_choice": true,
@@ -47808,14 +48226,17 @@
     },
     "vertex_ai/xai/grok-4.20-reasoning": {
         "cache_read_input_token_cost": 2e-07,
-        "input_cost_per_token": 2e-06,
+        "cache_read_input_token_cost_above_200k_tokens": 4e-07,
+        "input_cost_per_token": 1.25e-06,
+        "input_cost_per_token_above_200k_tokens": 2.5e-06,
         "litellm_provider": "vertex_ai",
         "max_input_tokens": 2000000,
         "max_output_tokens": 2000000,
         "max_tokens": 2000000,
         "mode": "chat",
-        "output_cost_per_token": 6e-06,
-        "source": "https://docs.x.ai/developers/models",
+        "output_cost_per_token": 2.5e-06,
+        "output_cost_per_token_above_200k_tokens": 5e-06,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
         "supports_function_calling": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
@@ -47823,6 +48244,44 @@
         "supports_vision": true,
         "supports_web_search": true
     },
+    "vertex_ai/xai/grok-4.3": {
+        "cache_read_input_token_cost": 2e-07,
+        "cache_read_input_token_cost_above_200k_tokens": 4e-07,
+        "input_cost_per_token": 1.25e-06,
+        "input_cost_per_token_above_200k_tokens": 2.5e-06,
+        "litellm_provider": "vertex_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 200000,
+        "max_tokens": 200000,
+        "mode": "chat",
+        "output_cost_per_token": 2.5e-06,
+        "output_cost_per_token_above_200k_tokens": 5e-06,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
+        "supports_function_calling": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
+    "vertex_ai/xai/grok-4.6": {
+        "cache_read_input_token_cost": 5e-07,
+        "cache_read_input_token_cost_above_200k_tokens": 1e-06,
+        "input_cost_per_token": 2e-06,
+        "input_cost_per_token_above_200k_tokens": 4e-06,
+        "litellm_provider": "vertex_ai",
+        "max_input_tokens": 524288,
+        "max_output_tokens": 524288,
+        "max_tokens": 524288,
+        "mode": "chat",
+        "output_cost_per_token": 6e-06,
+        "output_cost_per_token_above_200k_tokens": 1.2e-05,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
+        "supports_function_calling": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
     "vertex_ai/qwen/qwen3-235b-a22b-instruct-2507-maas": {
         "input_cost_per_token": 2.2e-07,
         "litellm_provider": "vertex_ai-qwen_models",
@@ -48081,6 +48540,16 @@
         "mode": "embedding",
         "output_cost_per_token": 0.0
     },
+    "voyage/voyage-multilingual-2": {
+        "input_cost_per_token": 1.2e-07,
+        "litellm_provider": "voyage",
+        "max_input_tokens": 32000,
+        "max_tokens": 32000,
+        "mode": "embedding",
+        "output_cost_per_token": 0.0,
+        "output_vector_size": 1024,
+        "source": "https://docs.voyageai.com/docs/pricing"
+    },
     "voyage/voyage-3-large": {
         "input_cost_per_token": 1.8e-07,
         "litellm_provider": "voyage",
@@ -48186,6 +48655,7 @@
         "output_cost_per_token": 0.0
     },
     "wandb/openai/gpt-oss-120b": {
+        "supports_reasoning": true,
         "max_tokens": 131072,
         "max_input_tokens": 131072,
         "max_output_tokens": 131072,
@@ -48196,6 +48666,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/openai/gpt-oss-20b": {
+        "supports_reasoning": true,
         "max_tokens": 131072,
         "max_input_tokens": 131072,
         "max_output_tokens": 131072,
@@ -48206,6 +48677,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/zai-org/GLM-4.5": {
+        "supports_reasoning": true,
         "max_tokens": 131072,
         "max_input_tokens": 131072,
         "max_output_tokens": 131072,
@@ -48234,6 +48706,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3-235B-A22B-Thinking-2507": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "max_output_tokens": 262144,
@@ -48290,6 +48763,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-V3.1": {
+        "supports_reasoning": true,
         "max_tokens": 128000,
         "max_input_tokens": 161000,
         "max_output_tokens": 128000,
@@ -48300,6 +48774,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-R1-0528": {
+        "supports_reasoning": true,
         "max_tokens": 161000,
         "max_input_tokens": 161000,
         "max_output_tokens": 161000,
@@ -52154,7 +52629,8 @@
         "max_tokens": 32768,
         "mode": "chat",
         "output_cost_per_token": 8e-07,
-        "supports_function_calling": true
+        "supports_function_calling": true,
+        "deprecation_date": "2026-10-01"
     },
     "scaleway/openai/gpt-oss-120b": {
         "input_cost_per_token": 1.5e-07,
@@ -52193,7 +52669,8 @@
         "mode": "chat",
         "output_cost_per_token": 5e-07,
         "supports_function_calling": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "deprecation_date": "2026-08-01"
     },
     "scaleway/hcompany/holo2-30b-a3b": {
         "input_cost_per_token": 3e-07,
@@ -52204,7 +52681,8 @@
         "mode": "chat",
         "output_cost_per_token": 7e-07,
         "supports_reasoning": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "deprecation_date": "2026-08-09"
     },
     "scaleway/mistralai/mistral-medium-3.5-128b": {
         "input_cost_per_token": 1.5e-06,
@@ -52227,7 +52705,8 @@
         "max_tokens": 16384,
         "mode": "chat",
         "output_cost_per_token": 2e-06,
-        "supports_function_calling": true
+        "supports_function_calling": true,
+        "deprecation_date": "2026-08-01"
     },
     "scaleway/mistralai/voxtral-small-24b-2507": {
         "input_cost_per_audio_token": 1.5e-07,
@@ -52238,7 +52717,8 @@
         "max_tokens": 16384,
         "mode": "chat",
         "output_cost_per_token": 3.5e-07,
-        "supports_audio_input": true
+        "supports_audio_input": true,
+        "deprecation_date": "2026-08-01"
     },
     "scaleway/mistralai/mistral-small-3.2-24b-instruct-2506": {
         "input_cost_per_token": 1.5e-07,
@@ -52260,7 +52740,8 @@
         "mode": "chat",
         "output_cost_per_token": 2e-07,
         "supports_vision": true,
-        "supports_function_calling": true
+        "supports_function_calling": true,
+        "deprecation_date": "2026-10-01"
     },
     "scaleway/BAAI/bge-multilingual-gemma2": {
         "input_cost_per_token": 1e-07,
@@ -54710,7 +55191,7 @@
         "supports_tool_choice": true
     },
     "bedrock_mantle/openai.gpt-oss-20b": {
-        "input_cost_per_token": 7.5e-08,
+        "input_cost_per_token": 7e-08,
         "output_cost_per_token": 3e-07,
         "litellm_provider": "bedrock_mantle",
         "max_input_tokens": 131072,
@@ -54744,8 +55225,8 @@
         "supports_tool_choice": true
     },
     "bedrock_mantle/openai.gpt-oss-safeguard-20b": {
-        "input_cost_per_token": 7.5e-08,
-        "output_cost_per_token": 3e-07,
+        "input_cost_per_token": 7e-08,
+        "output_cost_per_token": 2e-07,
         "litellm_provider": "bedrock_mantle",
         "max_input_tokens": 131072,
         "max_output_tokens": 65536,
@@ -54865,6 +55346,39 @@
         "supports_tool_choice": true,
         "supports_vision": true
     },
+    "bedrock_mantle/openai.gpt-daybreak-blue-5.6-sol": {
+        "input_cost_per_token": 5.5e-06,
+        "input_cost_per_token_above_272k_tokens": 1.1e-05,
+        "cache_creation_input_token_cost": 6.875e-06,
+        "cache_creation_input_token_cost_above_272k_tokens": 1.375e-05,
+        "cache_read_input_token_cost": 5.5e-07,
+        "cache_read_input_token_cost_above_272k_tokens": 1.1e-06,
+        "output_cost_per_token": 3.3e-05,
+        "output_cost_per_token_above_272k_tokens": 4.95e-05,
+        "litellm_provider": "bedrock_mantle",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "use_openai_responses_path": true,
+        "supported_endpoints": [
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-daybreak-blue-56-sol.html"
+    },
     "bedrock_mantle/openai.gpt-5.6-luna": {
         "input_cost_per_token": 2.2e-07,
         "input_cost_per_token_above_272k_tokens": 4.4e-07,
@@ -55060,6 +55574,96 @@
         "supports_reasoning": true,
         "supports_vision": true
     },
+    "bedrock_mantle/openai.gpt-6-astra": {
+        "input_cost_per_token": 1.1e-05,
+        "input_cost_per_token_above_272k_tokens": 2.2e-05,
+        "cache_creation_input_token_cost": 1.375e-05,
+        "cache_creation_input_token_cost_above_272k_tokens": 2.75e-05,
+        "cache_read_input_token_cost": 1.1e-06,
+        "cache_read_input_token_cost_above_272k_tokens": 2.2e-06,
+        "output_cost_per_token": 5.5e-05,
+        "output_cost_per_token_above_272k_tokens": 8.25e-05,
+        "litellm_provider": "bedrock_mantle",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "use_openai_responses_path": true,
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-6-astra.html"
+    },
+    "us.openai.gpt-6-astra": {
+        "input_cost_per_token": 1.1e-05,
+        "input_cost_per_token_above_272k_tokens": 2.2e-05,
+        "cache_creation_input_token_cost": 1.375e-05,
+        "cache_creation_input_token_cost_above_272k_tokens": 2.75e-05,
+        "cache_read_input_token_cost": 1.1e-06,
+        "cache_read_input_token_cost_above_272k_tokens": 2.2e-06,
+        "output_cost_per_token": 5.5e-05,
+        "output_cost_per_token_above_272k_tokens": 8.25e-05,
+        "litellm_provider": "bedrock_converse",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_tool_choice": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-6-astra.html"
+    },
+    "global.openai.gpt-6-astra": {
+        "input_cost_per_token": 1e-05,
+        "input_cost_per_token_above_272k_tokens": 2e-05,
+        "cache_creation_input_token_cost": 1.25e-05,
+        "cache_creation_input_token_cost_above_272k_tokens": 2.5e-05,
+        "cache_read_input_token_cost": 1e-06,
+        "cache_read_input_token_cost_above_272k_tokens": 2e-06,
+        "output_cost_per_token": 5e-05,
+        "output_cost_per_token_above_272k_tokens": 7.5e-05,
+        "litellm_provider": "bedrock_converse",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_tool_choice": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-6-astra.html"
+    },
     "bedrock_mantle/openai.gpt-5.5": {
         "input_cost_per_token": 5.5e-06,
         "input_cost_per_token_above_272k_tokens": 1.1e-05,
@@ -56654,6 +57258,14 @@
                 "model_info": {
                     "supports_mid_conversation_system": true
                 }
+            },
+            {
+                "name": "wandb-reasoning-baseline",
+                "pattern": "^wandb/",
+                "description": "Any Weights & Biases Inference model id, anchored to the wandb/ namespace so only that provider's ids match. W&B's serverless catalog is reasoning-first and grows faster than this registry names it, so an id the map has not described yet is treated as reasoning-capable and keeps the caller's reasoning_effort instead of dropping it or raising UnsupportedParamsError. Rules lose to exact entries, so a mapped non-reasoning model such as wandb/meta-llama/Llama-3.1-8B-Instruct is unaffected. Carries no mode and no pricing, so cost stays on the standard unpriced behavior and the deployment does not read as catalog-mapped to the router's reasoning-effort resolver.",
+                "model_info": {
+                    "supports_reasoning": true
+                }
             }
         ]
     },
@@ -56725,8 +57337,8 @@
         "rpm": 10
     },
     "vertex_ai/gemini-3.5-transcribe-preview": {
-        "input_cost_per_audio_token": 2.5e-06,
-        "input_cost_per_token": 2.5e-06,
+        "input_cost_per_audio_token": 2e-06,
+        "input_cost_per_token": 2e-06,
         "litellm_provider": "vertex_ai",
         "mode": "audio_transcription",
         "output_cost_per_token": 1.2e-05,
@@ -56761,6 +57373,27 @@
         ],
         "supports_audio_input": true
     },
+    "vertex_ai/gemini-3.5-live-translate-preview": {
+        "input_cost_per_audio_token": 3.5e-06,
+        "input_cost_per_token": 3.5e-06,
+        "litellm_provider": "vertex_ai",
+        "mode": "realtime",
+        "output_cost_per_audio_token": 2.1e-05,
+        "output_cost_per_token": 2.1e-05,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
+        "supported_endpoints": [
+            "/v1/realtime"
+        ],
+        "supported_modalities": [
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "audio",
+            "text"
+        ],
+        "supports_audio_input": true,
+        "supports_audio_output": true
+    },
     "perplexity/pplx-embed-context-v1-0.6b": {
         "input_cost_per_token": 8e-09,
         "litellm_provider": "perplexity",
@@ -58011,6 +58644,7 @@
         "supports_vision": false
     },
     "wandb/deepseek-ai/DeepSeek-V4-Flash": {
+        "supports_reasoning": true,
         "max_tokens": 1048576,
         "max_input_tokens": 1048576,
         "input_cost_per_token": 1.4e-07,
@@ -58023,6 +58657,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-V4-Flash-0731": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 1.3e-07,
@@ -58035,6 +58670,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-V4-Pro": {
+        "supports_reasoning": true,
         "max_tokens": 1048576,
         "max_input_tokens": 1048576,
         "input_cost_per_token": 1.15e-06,
@@ -58047,6 +58683,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/google/gemma-4-31B-it": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 1e-07,
@@ -58087,6 +58724,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/MiniMaxAI/MiniMax-M3": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 2.3e-07,
@@ -58099,6 +58737,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/moonshotai/Kimi-K2.7-Code": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 7.1e-07,
@@ -58111,6 +58750,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/moonshotai/Kimi-K2.6": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 6.5e-07,
@@ -58123,6 +58763,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/nvidia/NVIDIA-Nemotron-3.5-Lightning-30B-A3B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 1e-07,
@@ -58135,6 +58776,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/nvidia/NVIDIA-Nemotron-3-Ultra-550B-A55B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 7.5e-07,
@@ -58157,6 +58799,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.8-27B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 4e-07,
@@ -58169,6 +58812,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.6-35B-A3B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 2.5e-07,
@@ -58179,6 +58823,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.6-27B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 6e-07,
@@ -58191,6 +58836,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.5-35B-A3B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 2.5e-07,
@@ -58210,7 +58856,28 @@
         "supports_vision": false,
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
+    "wandb/deepseek-ai/DeepSeek-V4-Pro-0813": {
+        "litellm_provider": "wandb",
+        "mode": "chat",
+        "supports_reasoning": true,
+        "input_cost_per_token": 0.00000131,
+        "output_cost_per_token": 0.00000396,
+        "cache_read_input_token_cost": 0.000000044,
+        "supports_prompt_caching": true,
+        "source": "https://wandb.ai/site/pricing/tokens/"
+    },
+    "wandb/ibm-granite/granite-4.2-8b": {
+        "litellm_provider": "wandb",
+        "mode": "chat",
+        "supports_reasoning": true,
+        "input_cost_per_token": 0.0000001,
+        "output_cost_per_token": 0.00000015,
+        "cache_read_input_token_cost": 0.00000005,
+        "supports_prompt_caching": true,
+        "source": "https://wandb.ai/site/pricing/tokens/"
+    },
     "wandb/zai-org/GLM-5.2": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 7.6e-07,
@@ -59452,6 +60119,77 @@
             "image"
         ]
     },
+    "xai/grok-imagine-video": {
+        "input_cost_per_image": 0.002,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.05,
+        "output_cost_per_second_480p": 0.05,
+        "output_cost_per_second_720p": 0.07,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video",
+        "supported_modalities": [
+            "text",
+            "image",
+            "video"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
+    "xai/grok-imagine-video-1.5": {
+        "input_cost_per_image": 0.01,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.08,
+        "output_cost_per_second_1080p": 0.25,
+        "output_cost_per_second_480p": 0.08,
+        "output_cost_per_second_720p": 0.14,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video-1.5",
+        "supported_modalities": [
+            "text",
+            "image",
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
+    "xai/grok-imagine-video-1.5-2026-05-30": {
+        "input_cost_per_image": 0.01,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.08,
+        "output_cost_per_second_1080p": 0.25,
+        "output_cost_per_second_480p": 0.08,
+        "output_cost_per_second_720p": 0.14,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video-1.5",
+        "supported_modalities": [
+            "text",
+            "image",
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
+    "xai/grok-imagine-video-1.5-preview": {
+        "input_cost_per_image": 0.01,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.08,
+        "output_cost_per_second_1080p": 0.25,
+        "output_cost_per_second_480p": 0.08,
+        "output_cost_per_second_720p": 0.14,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video-1.5",
+        "supported_modalities": [
+            "text",
+            "image",
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
     "low/1024-x-1024/grok-imagine-image-2.0": {
         "input_cost_per_image": 0.04,
         "litellm_provider": "xai",
@@ -60719,6 +61457,7 @@
         "litellm_provider": "cloudflare",
         "mode": "audio_transcription",
         "output_cost_per_second": 0.0,
+        "rpm": 720,
         "source": "https://developers.cloudflare.com/workers-ai/models/whisper/",
         "supported_endpoints": [
             "/v1/audio/transcriptions"
@@ -60729,6 +61468,7 @@
         "litellm_provider": "cloudflare",
         "mode": "audio_transcription",
         "output_cost_per_second": 0.0,
+        "rpm": 720,
         "source": "https://developers.cloudflare.com/workers-ai/models/whisper-large-v3-turbo/",
         "supported_endpoints": [
             "/v1/audio/transcriptions"
@@ -60784,6 +61524,31 @@
         "supports_web_search": false,
         "output_cost_per_image": 0.08
     },
+    "gemini/lyria-3.5": {
+        "input_cost_per_token": 0,
+        "litellm_provider": "gemini",
+        "max_input_tokens": 1048576,
+        "max_output_tokens": 65536,
+        "max_tokens": 65536,
+        "mode": "chat",
+        "output_cost_per_token": 0,
+        "source": "https://ai.google.dev/gemini-api/docs/pricing",
+        "supported_modalities": [
+            "text"
+        ],
+        "supported_output_modalities": [
+            "audio"
+        ],
+        "supports_audio_input": false,
+        "supports_audio_output": true,
+        "supports_function_calling": false,
+        "supports_prompt_caching": false,
+        "supports_response_schema": false,
+        "supports_system_messages": false,
+        "supports_vision": false,
+        "supports_web_search": false,
+        "output_cost_per_image": 0.08
+    },
     "perplexity/anthropic/claude-fable-5": {
         "litellm_provider": "perplexity",
         "mode": "responses",
diff --git a/litellm/models/object_permission.py b/litellm/models/object_permission.py
index a09d50ddc33..f178c5ad47f 100644
--- a/litellm/models/object_permission.py
+++ b/litellm/models/object_permission.py
@@ -23,3 +23,4 @@ class LiteLLM_ObjectPermissionTable(LiteLLMPydanticObjectBase):
     blocked_tools: list[str] | None = []
     search_tools: list[str] | None = []
     mcp_tool_search_enabled: bool | None = None
+    skills: list[str] | None = None
diff --git a/litellm/proxy/_experimental/mcp_server/auth/user_api_key_auth_mcp.py b/litellm/proxy/_experimental/mcp_server/auth/user_api_key_auth_mcp.py
index 4bac65125b4..7e6de474b0b 100644
--- a/litellm/proxy/_experimental/mcp_server/auth/user_api_key_auth_mcp.py
+++ b/litellm/proxy/_experimental/mcp_server/auth/user_api_key_auth_mcp.py
@@ -179,16 +179,7 @@ def _gateway_dcr_challenge_target(
     mcp_servers: list[str] | None,
     client_ip: str | None,
 ) -> str | None:
-    """The single path-named server this request targets, iff it resolves to a
-    gateway-managed oauth2 server — the one per-server shape the gateway's own keyless
-    DCR flow serves end to end, so the 401 challenge may advertise the per-server
-    protected-resource metadata (whose ``authorization_servers`` names the gateway).
-
-    Multi-server CSV paths, header/path mismatches, unknown names, and every
-    client-forwarded or delegated mode return ``None``: those cells keep their existing
-    challenge (or absence of one), and a challenge is never emitted for a name the
-    public discovery routes would 404, so this reveals exactly the server set the
-    per-server protected-resource metadata already reveals."""
+    """Resolve a single path target whose sign-in metadata advertises the gateway."""
     from litellm.proxy._experimental.mcp_server.mcp_server_manager import (
         global_mcp_server_manager,
     )
@@ -217,7 +208,7 @@ def _is_gateway_dcr_challenge_scope(
     the caller is not a cold-start DCR client), on the scopes the gateway's keyless
     flow serves: the aggregate ``/mcp`` endpoint, an ``x-mcp-servers``-scoped request
     (the resource the client configured is still ``/mcp``), or a per-server path whose
-    single target is a gateway-managed oauth2 server. Every other named target keeps
+    single target advertises gateway-owned sign-in. Every other named target keeps
     its existing behavior, failing closed to the original admission error."""
     if not _is_litellm_auth_admission_error(exc):
         return False
@@ -236,7 +227,7 @@ def _gateway_dcr_challenge(
 ) -> HTTPException:
     """The RFC 9728 challenge pointing the client at the protected-resource metadata
     matching the scope it requested: the per-server document (same URL spelling the
-    request arrived on) when the single target is a gateway-managed oauth2 server,
+    request arrived on) when the single target advertises gateway-owned sign-in,
     else the gateway's aggregate document. Either way the client discovers the gateway
     as its authorization server and starts the same sign-in flow.
 
diff --git a/litellm/proxy/_experimental/mcp_server/db.py b/litellm/proxy/_experimental/mcp_server/db.py
index 7379126983a..789b2ffaef4 100644
--- a/litellm/proxy/_experimental/mcp_server/db.py
+++ b/litellm/proxy/_experimental/mcp_server/db.py
@@ -6,10 +6,18 @@ from collections.abc import Awaitable, Callable, Iterable, Mapping, Sequence
 from datetime import datetime, timedelta, timezone
 from typing import TYPE_CHECKING, Any, Final, Literal, Protocol, TypedDict, cast
 
+from fastapi import HTTPException
+from typing_extensions import ReadOnly
+
 from litellm._logging import verbose_proxy_logger
 from litellm._uuid import uuid
 from litellm.constants import MCP_PER_USER_TOKEN_EXPIRY_BUFFER_SECONDS
 from litellm.llms.custom_httpx.http_handler import get_async_httpx_client
+from litellm.proxy._experimental.mcp_server.oauth_identity_binding import (
+    RefreshTokenPresented,
+    credential_binding_matches,
+    enforce_oauth_identity_binding,
+)
 from litellm.proxy._experimental.mcp_server.oauth_utils import build_upstream_oauth2_token_request
 from litellm.proxy._types import (
     LiteLLM_MCPServerTable,
@@ -117,6 +125,7 @@ class _OAuthCredentialAccessToken(TypedDict):
 
 
 class OAuthCredentialPayload(_OAuthCredentialAccessToken, total=False):
+    identity_binding_proof: ReadOnly[str]
     type: str
     refresh_token: str
     expires_at: str
@@ -1393,6 +1402,7 @@ async def store_user_oauth_credential(
     expires_in: int | None = None,
     scopes: list[str] | None = None,
     skip_byok_guard: bool = False,
+    identity_binding_proof: str | None = None,
 ) -> None:
     """Persist an OAuth2 access token for a user+server pair.
 
@@ -1409,6 +1419,7 @@ async def store_user_oauth_credential(
         "type": "oauth2",
         "access_token": access_token,
         "connected_at": datetime.now(timezone.utc).isoformat(),
+        **({"identity_binding_proof": identity_binding_proof} if identity_binding_proof else {}),
     }
     if refresh_token:
         payload["refresh_token"] = refresh_token
@@ -1628,6 +1639,11 @@ async def refresh_user_oauth_token(
     warning and returns ``None`` — the caller is responsible for clearing the
     stale credential and triggering re-authentication.
     """
+    binding: Final = server.oauth_identity_binding
+    if binding is not None and binding.mode == "enforce":
+        if not await credential_binding_matches(binding, user_id, server.server_id, cred):
+            return None
+
     refresh_token: Final[str | None] = cred.get("refresh_token")
     token_url: Final[str | None] = getattr(server, "effective_token_url", None) or getattr(server, "token_url", None)
     server_id: Final[str] = getattr(server, "server_id", "")
@@ -1677,6 +1693,19 @@ async def refresh_user_oauth_token(
         )
         return None
 
+    try:
+        binding_proof: Final = await enforce_oauth_identity_binding(
+            server=server,
+            token_response=body,
+            litellm_user_id=user_id,
+            grant_type="refresh_token",
+            refresh_ownership=RefreshTokenPresented(refresh_token),
+        )
+    except HTTPException as exc:
+        if exc.status_code != 403:
+            raise
+        return None
+
     access_token: Final[str | None] = body.get("access_token")
     if not access_token:
         verbose_proxy_logger.warning(
@@ -1709,6 +1738,7 @@ async def refresh_user_oauth_token(
         refresh_token=new_refresh_token,
         expires_in=expires_in,
         scopes=scopes,
+        identity_binding_proof=binding_proof,
         skip_byok_guard=True,  # Row is already OAuth2; skip the extra find_unique check
     )
 
@@ -1742,6 +1772,10 @@ async def resolve_valid_user_oauth_token(
     grant: Final = oauth_grant_state(cred)
     if cred is None or grant == "absent":
         return None
+    binding: Final = server.oauth_identity_binding
+    if binding is not None and binding.mode == "enforce":
+        if not await credential_binding_matches(binding, user_id, server.server_id, cred):
+            return None
     if grant == "valid":
         return cred
     if prisma_client is None:
@@ -1782,7 +1816,17 @@ async def resolve_user_oauth_access_token(
             mcp_per_user_token_cache,
         )
 
-        if prefetched_creds is None:
+        binding: Final = server.oauth_identity_binding
+        enforce_binding: Final = binding is not None and binding.mode == "enforce"
+        if prefetched_creds is None and enforce_binding and binding is not None:
+            bound_token: Final = await mcp_per_user_token_cache.get_token(user_id, server_id)
+            if bound_token is not None:
+                if await credential_binding_matches(
+                    binding, user_id, server_id, {"identity_binding_proof": bound_token.identity_binding_proof}
+                ):
+                    return bound_token.access_token
+                await mcp_per_user_token_cache.delete(user_id, server_id)
+        if prefetched_creds is None and not enforce_binding:
             cached_token: Final = await mcp_per_user_token_cache.get(user_id, server_id)
             if cached_token is not None:
                 return cached_token
@@ -1816,7 +1860,9 @@ async def resolve_user_oauth_access_token(
         access_token: Final[str] = cred["access_token"]
         if prefetched_creds is None:
             ttl: Final = _compute_per_user_token_ttl(server, _remaining_token_seconds(cred.get("expires_at")))
-            await mcp_per_user_token_cache.set(user_id, server_id, access_token, ttl)
+            await mcp_per_user_token_cache.set(
+                user_id, server_id, access_token, ttl, identity_binding_proof=cred.get("identity_binding_proof")
+            )
         return access_token
     except Exception as e:
         verbose_proxy_logger.warning(
diff --git a/litellm/proxy/_experimental/mcp_server/discoverable_endpoints.py b/litellm/proxy/_experimental/mcp_server/discoverable_endpoints.py
index cab4b6c161a..42fbe82531c 100644
--- a/litellm/proxy/_experimental/mcp_server/discoverable_endpoints.py
+++ b/litellm/proxy/_experimental/mcp_server/discoverable_endpoints.py
@@ -57,6 +57,11 @@ from litellm.proxy._experimental.mcp_server.gateway_dcr_flow import (
     relative_request_url,
     revoke_refresh_token,
 )
+from litellm.proxy._experimental.mcp_server.oauth_identity_binding import (
+    RefreshOwnershipProven,
+    RefreshTokenPresented,
+    enforce_oauth_identity_binding,
+)
 from litellm.proxy._experimental.mcp_server.oauth_utils import (
     TOKEN_NO_CACHE_HEADERS,
     build_upstream_oauth2_token_request,
@@ -139,6 +144,7 @@ def encode_state_with_base_url(
     dcr_client_id: str | None = None,
     dcr_client_secret: str | None = None,
     dcr_token_endpoint_auth_method: MCPTokenEndpointAuthMethod | None = None,
+    oauth_nonce: str | None = None,
 ) -> str:
     """
     Encode the base_url, original state, and PKCE parameters using encryption.
@@ -149,9 +155,8 @@ def encode_state_with_base_url(
         code_challenge: PKCE code challenge from client
         code_challenge_method: PKCE code challenge method from client
         client_redirect_uri: Original redirect_uri from client
-        litellm_user_id: The SSO-authenticated litellm user captured at the bridge authorize
-            (interactive dcr_bridge oauth_delegate only); the callback seals it into the gateway
-            authorization code so the token mint can bind the envelope to this user
+        litellm_user_id: The authenticated user captured for bridge or identity-bound per-user OAuth;
+            the callback seals this credential owner into the authorization code
         mcp_server_id: The server the flow targets, sealed alongside litellm_user_id (bridge) or
             dcr_client_id (ephemeral mint) so the gateway code cannot be replayed against another
             server
@@ -169,6 +174,7 @@ def encode_state_with_base_url(
         An encrypted string that encodes all values
     """
     state_data: Final = {
+        "oauth_nonce": oauth_nonce,
         "base_url": base_url,
         "original_state": original_state,
         "code_challenge": code_challenge,
@@ -210,10 +216,10 @@ _BRIDGE_AUTH_CODE_PREFIX: Final = "llm_bcode_"
 
 
 class _BridgeAuthorizationCode(BaseModel):
-    """The identity and upstream code the gateway seals into the authorization code it hands a DCR
-    client for an interactive dcr_bridge oauth_delegate sign-in, recovered at the token endpoint."""
+    """Authenticated caller and upstream code sealed for bridge or identity-bound per-user OAuth."""
 
     model_config = ConfigDict(frozen=True)
+    oauth_nonce: str | None = None
     upstream_code: str = Field(min_length=1)
     litellm_user_id: str = Field(min_length=1)
     mcp_server_id: str = Field(min_length=1)
@@ -225,7 +231,12 @@ def is_bridge_authorization_code(code: str) -> bool:
     return code.startswith(_BRIDGE_AUTH_CODE_PREFIX)
 
 
-def seal_bridge_authorization_code(upstream_code: str, litellm_user_id: str, mcp_server_id: str) -> str:
+def seal_bridge_authorization_code(
+    upstream_code: str,
+    litellm_user_id: str,
+    mcp_server_id: str,
+    oauth_nonce: str | None = None,
+) -> str:
     """Seal the upstream authorization code and the SSO-captured litellm user into a gateway
     authorization code. The DCR client only echoes this opaque value back at the token endpoint; the
     gateway decrypts it there to recover the user (to bind the envelope) and the upstream code (to
@@ -234,7 +245,12 @@ def seal_bridge_authorization_code(upstream_code: str, litellm_user_id: str, mcp
     authenticated symmetric helper (the same family the OAuth state uses), so the client can neither
     read nor forge it."""
     payload: Final = json.dumps(
-        {"upstream_code": upstream_code, "litellm_user_id": litellm_user_id, "mcp_server_id": mcp_server_id},
+        {
+            "upstream_code": upstream_code,
+            "litellm_user_id": litellm_user_id,
+            "mcp_server_id": mcp_server_id,
+            "oauth_nonce": oauth_nonce,
+        },
         sort_keys=True,
     )
     return _BRIDGE_AUTH_CODE_PREFIX + encrypt_value_helper(payload)
@@ -547,6 +563,7 @@ async def _store_per_user_token_server_side(
     server: MCPServer,
     user_id: str,
     token_response: dict[str, Any],
+    identity_binding_proof: str | None = None,
 ) -> None:
     """Persist the OAuth token server-side and warm the Redis cache.
 
@@ -588,6 +605,7 @@ async def _store_per_user_token_server_side(
             refresh_token=refresh_token,
             expires_in=expires_in,
             scopes=scopes,
+            identity_binding_proof=identity_binding_proof,
         )
         verbose_logger.info(
             "_store_per_user_token_server_side: stored token for user=%s server=%s",
@@ -616,6 +634,7 @@ async def _store_per_user_token_server_side(
         server_id=server.server_id,
         access_token=access_token,
         ttl=ttl,
+        identity_binding_proof=identity_binding_proof,
     )
 
 
@@ -854,6 +873,11 @@ async def authorize_with_server(
             ),
         )
 
+    binding: Final = resolved_server.oauth_identity_binding
+    enforce_binding: Final = binding is not None and binding.mode == "enforce"
+    if enforce_binding:
+        _require_s256_pkce(code_challenge, code_challenge_method)
+
     if resolved_server.is_dcr_bridge:
         # Enforce S256 PKCE on both bridge arms. The relay arm forwards the validated,
         # now-non-optional pair to the upstream authorize; the short-circuit arm keeps
@@ -884,19 +908,16 @@ async def authorize_with_server(
     base_url: Final = urlunparse(parsed._replace(query=""))
     request_base_url: Final = get_request_base_url(request)
 
-    # Interactive dcr_bridge oauth_delegate sign-in: this arm runs the gateway /callback and /token in
-    # the loop, so the gateway can capture the litellm user here (from the browser's UI session) and
-    # carry it to the back-channel token mint. Seal the SSO user and the target server into the state;
-    # the callback reads them back to mint the gateway authorization code. A DCR client cannot present a
-    # litellm key, so the browser session is the only identity source; without one there is nothing to
-    # bind, so send the user through login first. Every other oauth2 server keeps the identity-less state.
+    # Seal the authenticated caller into state so the token exchange cannot select another credential owner.
     litellm_user_id: str | None = None
-    if resolved_server.is_dcr_bridge and resolved_server.is_oauth_delegate:
+    if enforce_binding or (resolved_server.is_dcr_bridge and resolved_server.is_oauth_delegate):
         from litellm.proxy._experimental.mcp_server.byok_oauth_endpoints import (  # noqa: PLC0415  # inline import avoids a module-load circular import
             _user_id_from_session_cookie,
         )
 
-        litellm_user_id = _user_id_from_session_cookie(request)
+        litellm_user_id = (
+            await _extract_user_id_from_request(request) if enforce_binding else None
+        ) or _user_id_from_session_cookie(request)
         if litellm_user_id is None:
             return _redirect_to_litellm_login(request)
         denial: Final = await _bridge_authorize_access_denial(
@@ -908,9 +929,11 @@ async def authorize_with_server(
         if denial is not None:
             return denial
 
+    oauth_nonce: Final = secrets.token_urlsafe(32) if enforce_binding else None
     encoded_state: Final = encode_state_with_base_url(
         base_url=base_url,
         original_state=state,
+        oauth_nonce=oauth_nonce,
         code_challenge=code_challenge,
         code_challenge_method=code_challenge_method,
         client_redirect_uri=redirect_uri,
@@ -930,11 +953,16 @@ async def authorize_with_server(
         "state": relay_state,
         "response_type": response_type or "code",
     }
+    if oauth_nonce:
+        params["nonce"] = oauth_nonce
     if scope:
         params["scope"] = scope
     elif resolved_server.scopes:
         params["scope"] = " ".join(resolved_server.scopes)
 
+    if enforce_binding and "openid" not in params.get("scope", "").split():
+        params["scope"] = f"openid {params.get('scope', '')}".strip()
+
     if code_challenge:
         params["code_challenge"] = code_challenge
     if code_challenge_method:
@@ -1015,6 +1043,12 @@ async def exchange_token_with_server(
     except TokenEndpointAuthConfigError as exc:
         raise HTTPException(status_code=400, detail=str(exc)) from exc
 
+    request_user_id: Final = (
+        await _extract_user_id_from_request(request)
+        if resolved_server.needs_user_oauth_token or resolved_server.oauth_identity_binding is not None
+        else None
+    )
+
     bridge_identity: _BridgeAuthorizationCode | None = None
     bridge_mint_ready: _BridgeMintReady | None = None
     bridge_upstream_refresh: SecretStr | None = None
@@ -1051,7 +1085,13 @@ async def exchange_token_with_server(
         refresh_request_scope = scope or bridge_upstream_scope
         if refresh_request_scope:
             token_data["scope"] = refresh_request_scope
+        refresh_ownership = (  # rebind-ok: grant-specific branches assign one ownership value
+            RefreshOwnershipProven()
+            if bridge_upstream_refresh is not None
+            else RefreshTokenPresented(upstream_refresh_token)
+        )
     else:
+        refresh_ownership = None  # rebind-ok: grant-specific branches assign one ownership value
         if not code:
             raise HTTPException(
                 status_code=400,
@@ -1070,6 +1110,14 @@ async def exchange_token_with_server(
                     detail="Authorization code was issued for a different MCP server",
                 )
             code = bridge_identity.upstream_code
+        binding: Final = resolved_server.oauth_identity_binding
+        if binding is not None and binding.mode == "enforce":
+            if bridge_identity is None or not bridge_identity.oauth_nonce:
+                raise HTTPException(status_code=403, detail={"error": "oauth_identity_binding_failed"})
+            if request_user_id is not None and request_user_id != bridge_identity.litellm_user_id:
+                raise HTTPException(status_code=403, detail={"error": "oauth_principal_mismatch"})
+            if not code_verifier:
+                raise HTTPException(status_code=403, detail={"error": "oauth_identity_binding_failed"})
         bridge_token_relay: Final = _dcr_bridge_relays_client_registration(resolved_server)
         if bridge_token_relay and not redirect_uri:
             raise HTTPException(
@@ -1097,6 +1145,16 @@ async def exchange_token_with_server(
                 return _bridge_mint_error_response(prepared)
             bridge_mint_ready = prepared
 
+    refresh_binding: Final = resolved_server.oauth_identity_binding
+    if grant_type == "refresh_token" and refresh_binding is not None and refresh_binding.mode == "enforce":
+        await enforce_oauth_identity_binding(
+            server=resolved_server,
+            token_response={},
+            litellm_user_id=request_user_id,
+            grant_type=grant_type,
+            refresh_ownership=refresh_ownership,
+        )
+
     async_client: Final = get_async_httpx_client(llm_provider=httpxSpecialProvider.Oauth2Check)
     try:
         response: Final = await async_client.post(
@@ -1137,17 +1195,34 @@ async def exchange_token_with_server(
             server_id=resolved_server.server_id,
         )
 
+    # Bind the exchanged token to the LiteLLM caller BEFORE it is returned, stored, or cached, so a
+    # token minted for a different upstream principal never becomes usable under the caller's user_id.
+    resolved_user_id: Final = bridge_identity.litellm_user_id if bridge_identity else request_user_id
+    binding_proof: Final = (
+        await enforce_oauth_identity_binding(
+            server=resolved_server,
+            token_response=token_response,
+            litellm_user_id=resolved_user_id,
+            grant_type=grant_type,
+            refresh_ownership=refresh_ownership,
+            expected_nonce=bridge_identity.oauth_nonce if bridge_identity else None,
+        )
+        if isinstance(token_response, dict)
+        else None
+    )
+
     # Store server-side when the server is configured for per-user OAuth and
     # the calling client has provided a valid LiteLLM identity.
     # Errors are non-fatal: the token is still returned to the client.
     if resolved_server.needs_user_oauth_token:
-        user_id: Final = await _extract_user_id_from_request(request)
+        user_id: Final = resolved_user_id
         if user_id:
             try:
                 await _store_per_user_token_server_side(
                     server=resolved_server,
                     user_id=user_id,
                     token_response=token_response,
+                    identity_binding_proof=binding_proof,
                 )
             except Exception as exc:
                 verbose_logger.warning(
@@ -2134,7 +2209,10 @@ async def callback(
         forwarded_code = code
         if isinstance(litellm_user_id, str) and litellm_user_id and isinstance(mcp_server_id, str) and mcp_server_id:
             forwarded_code = seal_bridge_authorization_code(
-                upstream_code=code, litellm_user_id=litellm_user_id, mcp_server_id=mcp_server_id
+                upstream_code=code,
+                litellm_user_id=litellm_user_id,
+                mcp_server_id=mcp_server_id,
+                oauth_nonce=state_data.get("oauth_nonce"),
             )
         elif isinstance(dcr_client_id, str) and dcr_client_id and isinstance(mcp_server_id, str) and mcp_server_id:
             forwarded_code = seal_passthrough_authorization_code(
@@ -2310,8 +2388,7 @@ async def _build_oauth_protected_resource_response(
     it. Only the legacy ``is_oauth_passthrough`` opt-in rewrites ``resource`` to
     the gateway's own URL so clients present the bearer token back to the gateway.
 
-    An explicitly named gateway-managed oauth2 server (interactive with
-    gateway-vaulted per-user tokens, or M2M) advertises the gateway's own
+    An explicitly named server with gateway-owned sign-in advertises the gateway's own
     authorization server (``{base}/mcp``): a keyless DCR client that configured the
     per-server URL completes the same sign-in flow the aggregate ``/mcp`` endpoint
     supports and is admitted with a gateway session bearer. The per-server relay
@@ -2401,11 +2478,6 @@ async def _build_oauth_protected_resource_response(
     if obo_response is not None:
         return obo_response
 
-    # An OBO server with no configured issuer falls through to the gateway default so discovery still
-    # returns metadata; every other non-oauth2 named server 404s to avoid enumeration.
-    if mcp_server is None or mcp_server.auth_type != MCPAuth.oauth2_token_exchange:
-        _raise_unless_oauth2_discovery_server(mcp_server, mcp_server_name, "not an OAuth-protected resource")
-
     if explicitly_named and mcp_server is not None and mcp_server.advertises_gateway_authorization_server:
         return {
             "authorization_servers": [f"{request_base_url}/mcp"],
@@ -2413,6 +2485,9 @@ async def _build_oauth_protected_resource_response(
             "scopes_supported": (mcp_server.scopes if mcp_server.scopes else []),
         }
 
+    if mcp_server is None or mcp_server.auth_type != MCPAuth.oauth2_token_exchange:
+        _raise_unless_oauth2_discovery_server(mcp_server, mcp_server_name, "not an OAuth-protected resource")
+
     return {
         "authorization_servers": [
             (f"{request_base_url}/{mcp_server_name}" if mcp_server_name else f"{request_base_url}")
diff --git a/litellm/proxy/_experimental/mcp_server/gateway_dcr_flow.py b/litellm/proxy/_experimental/mcp_server/gateway_dcr_flow.py
index 3d94fa345d0..f3fdd54b39d 100644
--- a/litellm/proxy/_experimental/mcp_server/gateway_dcr_flow.py
+++ b/litellm/proxy/_experimental/mcp_server/gateway_dcr_flow.py
@@ -122,13 +122,13 @@ _USED_CODE_CACHE_PREFIX: Final = "mcp_gateway_dcr_code_used:"
 _USED_FLOW_CACHE_PREFIX: Final = "mcp_gateway_dcr_flow_used:"
 _USED_REFRESH_CACHE_PREFIX: Final = "mcp_gateway_dcr_refresh_used:"
 
-MAX_REDIRECT_URIS: Final = 3
+MAX_REDIRECT_URIS: Final = 4
 MAX_REDIRECT_URI_LENGTH: Final = 256
 MAX_CLIENT_ID_LENGTH: Final = 2048
 """Registration bounds. They exist to bound the sealed client_id, which rides inside
-every session-token claim set: 3 URIs of 256 bytes seal to roughly 1.2KB, comfortably
-under this cap and under the session token's own 4KB ceiling. Claude Desktop and MCP
-Inspector register one or two redirect URIs."""
+every session-token claim set. Four 256-character ASCII URIs seal to roughly 1.5KB;
+the encoded client_id is checked against its own cap before registration succeeds.
+VS Code registers four callbacks for its web and desktop environments."""
 
 MAX_STATE_LENGTH: Final = 1024
 """Bound on the client ``state`` sealed into the flow cookie and echoed on the auth-code
@@ -411,7 +411,7 @@ def relative_request_url(request: Request) -> str:
 
 
 def resolve_scoped_resource_server(request: Request, resource: str | None) -> MCPServer | None:
-    """Resolve an RFC 8707 ``resource`` value to the single gateway-managed oauth2 server it
+    """Resolve an RFC 8707 ``resource`` value to the single gateway-owned server it
     names, or ``None`` for every other shape: absent, the aggregate resource, a foreign
     host, an unparseable value, a multi-server path, an unknown name, or any server mode the
     keyless gateway flow does not serve (whose protected-resource metadata never directs a
@@ -443,7 +443,7 @@ def resolve_scoped_resource_server(request: Request, resource: str | None) -> MC
     if len(names) != 1:
         return None
     server: Final = global_mcp_server_manager.get_mcp_server_by_name(names[0])
-    if server is None or not server.is_gateway_managed_oauth2:
+    if server is None or not (server.is_gateway_managed_oauth2 or server.advertises_gateway_authorization_server):
         return None
     return server
 
@@ -729,11 +729,15 @@ async def _flow_target(
     server: Final = global_mcp_server_manager.get_mcp_server_by_id(flow.resource_server_id)
     if (
         server is None
-        or not server.is_gateway_managed_oauth2
+        or not (server.is_gateway_managed_oauth2 or server.advertises_gateway_authorization_server)
         or not await lookup_server_reachability(flow.user_id, server.server_id)
     ):
         return "stale", None
-    state: Final = "m2m" if MCPServerManager.effective_oauth2_flow(server) == "client_credentials" else "interactive"
+    state: Final = (
+        "interactive"
+        if server.is_gateway_managed_oauth2 and MCPServerManager.effective_oauth2_flow(server) != "client_credentials"
+        else "m2m"
+    )
     return state, server
 
 
diff --git a/litellm/proxy/_experimental/mcp_server/mcp_debug.py b/litellm/proxy/_experimental/mcp_server/mcp_debug.py
index c608e0a73f0..07e77856894 100644
--- a/litellm/proxy/_experimental/mcp_server/mcp_debug.py
+++ b/litellm/proxy/_experimental/mcp_server/mcp_debug.py
@@ -22,7 +22,16 @@ Response headers returned (all values are masked for safety):
     x-mcp-debug-auth-resolution
         Which auth priority was used for the outbound MCP call:
         ``per-request-header``, ``m2m-client-credentials``, ``static-token``,
-        ``oauth2-passthrough``, or ``no-auth``.
+        ``oauth2-passthrough``, ``stored-user-token``, ``token-exchange``,
+        ``id-jag``, ``aws-sigv4``, ``extra-headers``, or ``no-auth``.
+        ``unresolved`` means no outcome was available before the first response
+        frame; ``multiple`` means several servers resolved credentials;
+        ``not-applicable`` covers stdio; ``resolution-failed`` is a resolver error.
+
+    x-mcp-debug-auth-resolutions
+        For multiple servers, a JSON map of server IDs to resolution labels.
+        At most 32 entries are included; x-mcp-debug-auth-resolutions-truncated
+        is true when additional servers were omitted. No credentials are included.
 
     x-mcp-debug-outbound-url
         The upstream MCP server URL that will receive the request.
@@ -58,10 +67,16 @@ header is free for OAuth2 discovery::
 Symptom: ``x-mcp-debug-oauth2-token`` shows ``(none)`` and
 ``x-mcp-debug-auth-resolution`` shows ``no-auth``.
 
-This means the client didn't go through the OAuth2 flow. Check that:
-1. The ``Authorization`` header is NOT set as a static header in the client config.
-2. The ``.well-known/oauth-protected-resource`` endpoint returns valid metadata.
-3. The MCP server in LiteLLM config has ``auth_type: oauth2``.
+``no-auth`` means the resolved upstream client carries no authentication.
+An absent inbound OAuth2 token does not imply the user skipped OAuth: the gateway
+can retrieve a stored per-user token, reported as ``stored-user-token``.
+``unresolved`` is used when a stream starts before credential resolution, or a
+request (such as initialization or a cached tool listing) resolves no credential.
+Debug reporting does not fetch credentials or delay a streaming frame to resolve them.
+``extra-headers`` identifies supplied headers that won over the resolver or were
+the only headers supplied; their values are never inspected to guess a scheme.
+``per-request-header`` denotes a legacy credential override, including a BYOK
+credential supplied by the gateway; it does not imply a caller-supplied token.
 
 **Common issue: M2M token used instead of user token**
 
@@ -69,8 +84,8 @@ Symptom: ``x-mcp-debug-auth-resolution`` shows ``m2m-client-credentials``.
 
 This means the server has ``client_id``/``client_secret``/``token_url``
 configured and LiteLLM is fetching a machine-to-machine token instead of
-using the per-user OAuth2 token. If you want per-user tokens, remove the
-client credentials from the server config.
+using the per-user OAuth2 token. For gateway-stored per-user tokens,
+configure ``oauth2_flow: authorization_code``.
 
 Usage from Claude Code::
 
@@ -87,21 +102,21 @@ Usage with curl::
 
 import asyncio
 import json
-from collections.abc import AsyncIterator
+from collections.abc import AsyncIterator, Callable, Mapping
 from itertools import islice
-from typing import TYPE_CHECKING, Final
+from types import MappingProxyType
+from typing import Final
 from urllib.parse import parse_qsl, urlencode
 
 import httpx
 from pydantic import JsonValue, TypeAdapter, ValidationError
+from starlette.requests import HTTPConnection
 from starlette.types import Message, Send
 
 from litellm.litellm_core_utils.secret_redaction import REDACTED, redact_string
 from litellm.litellm_core_utils.sensitive_data_masker import SensitiveDataMasker
 from litellm.proxy._experimental.mcp_server.faults.traversal import iter_exception_tree
-
-if TYPE_CHECKING:
-    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+from litellm.proxy._experimental.mcp_server.outbound_credentials.types import AuthResolution
 
 # Header the client sends to opt into debug mode
 MCP_DEBUG_REQUEST_HEADER: Final = "x-litellm-mcp-debug"
@@ -110,6 +125,83 @@ MCP_DEBUG_REQUEST_HEADER: Final = "x-litellm-mcp-debug"
 _RESPONSE_HEADER_PREFIX: Final = "x-mcp-debug"
 
 
+MCP_AUTH_DIAGNOSTICS_SCOPE_KEY: Final = "litellm.mcp.auth_diagnostics"
+
+
+def record_auth_resolution(server_id: str, source: AuthResolution) -> None:
+    from mcp.server.lowlevel.server import request_ctx
+
+    context: Final[object] = request_ctx.get(None)
+    request: Final[object] = getattr(context, "request", None)
+    if isinstance(request, HTTPConnection):
+        diagnostics: Final[object] = request.scope.get(MCP_AUTH_DIAGNOSTICS_SCOPE_KEY)
+        if isinstance(diagnostics, MCPAuthDiagnostics):
+            diagnostics.record(server_id, source)
+
+
+class MCPAuthDiagnostics:
+    def __init__(self) -> None:
+        self._outcomes: tuple[tuple[str, AuthResolution], ...] = ()
+
+    def record(self, server_id: str, resolution: AuthResolution) -> None:
+        self._outcomes = tuple(item for item in self._outcomes if item[0] != server_id) + ((server_id, resolution),)
+
+    def resolution(self) -> str:
+        match self._outcomes:
+            case ():
+                return AuthResolution.unresolved.value
+            case ((_, source),):
+                return source.value
+            case _:
+                return AuthResolution.multiple.value
+
+    def headers(self) -> Mapping[str, str]:
+        if len(self._outcomes) <= 1:
+            return MappingProxyType({"x-mcp-debug-auth-resolution": self.resolution()})
+        return MappingProxyType(
+            {
+                "x-mcp-debug-auth-resolution": AuthResolution.multiple.value,
+                "x-mcp-debug-auth-resolutions": json.dumps(
+                    {
+                        server_id: source.value for server_id, source in self._outcomes[:32]
+                    },  # mutable-ok: JSON encoder requires a concrete dict
+                    separators=(",", ":"),
+                    ensure_ascii=True,
+                ),
+                **(
+                    MappingProxyType({"x-mcp-debug-auth-resolutions-truncated": "true"})
+                    if len(self._outcomes) > 32
+                    else MappingProxyType({})
+                ),
+            }
+        )
+
+
+class _DiagnosticSend:
+    def __init__(self, send: Send, headers: Mapping[str, str], resolution: Callable[[], Mapping[str, str]]) -> None:
+        self._send = send
+        self._headers = headers
+        self._resolution = resolution
+        self._start: Message | None = None
+
+    async def __call__(self, message: Message) -> None:
+        if message["type"] == "http.response.start":
+            self._start = message
+            return
+        if self._start is not None:
+            start: Final = self._start
+            self._start = None
+            headers: Final = MappingProxyType({**self._headers, **self._resolution()})
+            await self._send(
+                {  # mutable-ok: ASGI send consumes a mutable message mapping
+                    **start,
+                    "headers": tuple(start.get("headers", ()))
+                    + tuple((key.encode(), value.encode()) for key, value in headers.items()),
+                }
+            )
+        await self._send(message)
+
+
 class MCPDebug:
     """
     Static helper class for MCP OAuth2 debug headers.
@@ -157,37 +249,6 @@ class MCPDebug:
                 return val.strip().lower() in ("true", "1", "yes")
         return False
 
-    @staticmethod
-    def resolve_auth_resolution(
-        server: "MCPServer",
-        mcp_auth_header: str | None,
-        mcp_server_auth_headers: dict[str, dict[str, str]] | None,
-        oauth2_headers: dict[str, str] | None,
-    ) -> str:
-        """
-        Determine which auth priority will be used for the outbound MCP call.
-
-        Returns one of: ``per-request-header``, ``m2m-client-credentials``,
-        ``static-token``, ``oauth2-passthrough``, or ``no-auth``.
-        """
-        from litellm.types.mcp import MCPAuth
-
-        has_server_specific: Final = bool(
-            mcp_server_auth_headers
-            and (
-                mcp_server_auth_headers.get(server.alias or "") or mcp_server_auth_headers.get(server.server_name or "")
-            )
-        )
-        if has_server_specific or mcp_auth_header:
-            return "per-request-header"
-        if server.has_client_credentials:
-            return "m2m-client-credentials"
-        if server.authentication_token:
-            return "static-token"
-        if oauth2_headers and server.auth_type == MCPAuth.oauth2:
-            return "oauth2-passthrough"
-        return "no-auth"
-
     @staticmethod
     def build_debug_headers(
         *,
@@ -257,12 +318,21 @@ class MCPDebug:
         return debug
 
     @staticmethod
-    def wrap_send_with_debug_headers(send: Send, debug_headers: dict[str, str]) -> Send:
+    def wrap_send_with_debug_headers(
+        send: Send,
+        debug_headers: Mapping[str, str],
+        resolution: Callable[[], Mapping[str, str]] | None = None,
+        *,
+        request_method: str | None = None,
+    ) -> Send:
         """
         Return a new ASGI ``send`` callable that injects *debug_headers*
         into the ``http.response.start`` message.
         """
 
+        if resolution is not None and request_method == "POST":
+            return _DiagnosticSend(send, debug_headers, resolution)
+
         async def _send_with_debug(message: Message) -> None:
             if message["type"] == "http.response.start":
                 headers: Final = list(message.get("headers", []))
@@ -279,8 +349,6 @@ class MCPDebug:
         raw_headers: dict[str, str] | None,
         scope: dict,
         mcp_servers: list[str] | None,
-        mcp_auth_header: str | None,
-        mcp_server_auth_headers: dict[str, dict[str, str]] | None,
         oauth2_headers: dict[str, str] | None,
         client_ip: str | None,
     ) -> dict[str, str]:
@@ -301,16 +369,13 @@ class MCPDebug:
 
         server_url: str | None = None
         server_auth_type: str | None = None
-        auth_resolution = "no-auth"
+        auth_resolution: Final = AuthResolution.unresolved.value
 
         for server_name in mcp_servers or []:
             server = global_mcp_server_manager.get_mcp_server_by_name(server_name, client_ip=client_ip)
             if server:
                 server_url = server.url
                 server_auth_type = server.auth_type
-                auth_resolution = MCPDebug.resolve_auth_resolution(
-                    server, mcp_auth_header, mcp_server_auth_headers, oauth2_headers
-                )
                 break
 
         scope_headers: Final = MCPRequestHandler._safe_get_headers_from_scope(scope)
diff --git a/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py b/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py
index b6712d68f72..b6e6e6adde5 100644
--- a/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py
+++ b/litellm/proxy/_experimental/mcp_server/mcp_server_manager.py
@@ -25,6 +25,7 @@ from collections.abc import (
 )
 from contextlib import asynccontextmanager
 from dataclasses import dataclass, replace
+from functools import lru_cache
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Literal, TypeAlias, TypedDict, cast
 from urllib.parse import ParseResult, urlparse
@@ -80,7 +81,7 @@ from litellm.proxy._experimental.mcp_server.faults.list_outcomes import (
     raise_classified_list_failure,
     upstream_auth_challenge,
 )
-from litellm.proxy._experimental.mcp_server.mcp_debug import describe_upstream_http_failure
+from litellm.proxy._experimental.mcp_server.mcp_debug import describe_upstream_http_failure, record_auth_resolution
 from litellm.proxy._experimental.mcp_server.oauth2_token_cache import (
     MCPPerUserTokenCache,
     mcp_per_user_token_cache,
@@ -109,12 +110,14 @@ from litellm.proxy._experimental.mcp_server.outbound_credentials.oauth_token_sto
 from litellm.proxy._experimental.mcp_server.outbound_credentials.per_user_oauth_store import (
     LazyPerUserOAuthTokenStore,
 )
+from litellm.proxy._experimental.mcp_server.outbound_credentials.resolver import resolve_credentials_with_source
 from litellm.proxy._experimental.mcp_server.outbound_credentials.token_exchange_provider import (
     build_token_exchanger,
 )
 from litellm.proxy._experimental.mcp_server.outbound_credentials.types import (
     DEFAULT_CREDENTIAL_HEADER,
     AuthorizationCodeConfig,
+    AuthResolution,
     ClientCredentialsConfig,
     CredError,
     IdJagConfig,
@@ -881,6 +884,53 @@ def _sanitized_error_text(exc: Exception) -> str:
     return re.sub(r"https?://\S+", "<url>", str(exc))[:200]
 
 
+async def _openapi_spec_health(
+    spec_path: str, *, timeout: float
+) -> tuple[Literal["healthy", "unhealthy", "unknown"], str | None]:
+    """Check specification availability, not upstream operations or user credentials."""
+    from litellm.llms.custom_httpx.http_handler import HTTPResponseLimitError
+    from litellm.proxy._experimental.mcp_server.openapi_to_mcp_generator import load_openapi_spec_async
+
+    if not spec_path.startswith(("http://", "https://")):
+        return "unknown", "OpenAPI servers have no protocol-level health probe"
+    try:
+        await asyncio.wait_for(load_openapi_spec_async(spec_path, max_bytes=10 * 1024 * 1024), timeout=timeout)
+    except asyncio.TimeoutError:
+        return "unhealthy", f"OpenAPI specification check timed out after {timeout} seconds"
+    except HTTPStatusError as exc:
+        return "unhealthy", f"OpenAPI specification request failed (HTTP {exc.response.status_code})"
+    except HTTPResponseLimitError as exc:
+        return "unknown", f"OpenAPI specification probe refused: {exc}"
+    except (httpx.RequestError, ValueError, OSError) as exc:
+        return "unhealthy", f"OpenAPI specification could not be loaded ({type(exc).__name__})"
+    return "healthy", None
+
+
+class _OpenAPIHealthProbe:
+    def __init__(self, spec_path: str, clock: Callable[[], float] = time.monotonic) -> None:
+        self.spec_path = spec_path
+        self.clock = clock
+        self.lock = asyncio.Lock()
+        self.checked_at = float("-inf")
+        self.result: tuple[Literal["healthy", "unhealthy", "unknown"], str | None, datetime.datetime] | None = None
+
+    async def check(self) -> tuple[Literal["healthy", "unhealthy", "unknown"], str | None, datetime.datetime]:
+        async with self.lock:
+            if self.result is not None and self.clock() - self.checked_at < 30.0:
+                return self.result
+            try:
+                status, error = await _openapi_spec_health(self.spec_path, timeout=MCP_HEALTH_CHECK_TIMEOUT)
+            except asyncio.CancelledError:
+                return (
+                    "unknown",
+                    "OpenAPI specification check was cancelled",
+                    datetime.datetime.now(datetime.timezone.utc),
+                )
+            self.result = (status, error, datetime.datetime.now(datetime.timezone.utc))
+            self.checked_at = self.clock()
+            return self.result
+
+
 def _discovery_failure_leaves_needs_unresolved(
     *,
     needs_authorization_url: bool,
@@ -1752,6 +1802,7 @@ class MCPServerManager:
             token_exchanger=build_token_exchanger(),
         )
         self.registry: dict[str, MCPServer] = {}
+        self._openapi_health_probes: Callable[[str], _OpenAPIHealthProbe] = lru_cache(maxsize=128)(_OpenAPIHealthProbe)
         self.config_mcp_servers: dict[str, MCPServer] = {}
         """
         eg.
@@ -2447,6 +2498,8 @@ class MCPServerManager:
                 allow_elicitation=bool(server_config.get("allow_elicitation", False)),
                 timeout=server_config.get("timeout", None),
                 max_concurrent_requests=server_config.get("max_concurrent_requests", None),
+                token_validation=server_config.get("token_validation", None),
+                oauth_identity_binding=server_config.get("oauth_identity_binding", None),
             )
             self._assign_unique_short_prefix(new_server)
             _warn_internal_delegate_pkce_if_applicable(new_server, source="config")
@@ -3838,13 +3891,21 @@ class MCPServerManager:
         (authorization_code's browser-OAuth 401, token_exchange's RFC 9728 challenge) or maps any
         other ``CredError`` onto its public HTTP status; it never returns an error as a value.
         """
-        match await provider.resolve_credentials(to_subject(user_api_key_auth, subject_token), spec):
-            case Ok(auth):
+        match await resolve_credentials_with_source(provider, to_subject(user_api_key_auth, subject_token), spec):
+            case Ok(credential):
+                auth: Final = credential.auth
                 # NoOpAuth has no header_name and so never conflicts.
                 header_name: Final[str | None] = getattr(auth, "header_name", None)
                 if header_name is None or not extra_headers:
+                    source: Final = (
+                        AuthResolution.extra_headers
+                        if credential.source == AuthResolution.no_auth and extra_headers
+                        else credential.source
+                    )
+                    record_auth_resolution(server.server_id, source)
                     return auth, extra_headers
                 if not has_header(extra_headers, header_name):
+                    record_auth_resolution(server.server_id, credential.source)
                     return auth, extra_headers
                 if isinstance(
                     spec.config,
@@ -3859,11 +3920,14 @@ class MCPServerManager:
                     # one-shot 401 refetch is lost with it). Drop only the header the resolved
                     # credential is about to occupy, so a static credential the operator aimed at a
                     # DIFFERENT header still reaches upstream.
+                    record_auth_resolution(server.server_id, credential.source)
                     return auth, without_header(extra_headers, header_name)
                 # Other modes: an Authorization already supplied via extra_headers (a forwarded caller
                 # header or static_headers) is intentional and wins; v1 applies those last.
+                record_auth_resolution(server.server_id, AuthResolution.extra_headers)
                 return None, extra_headers
             case Error(err):
+                record_auth_resolution(server.server_id, AuthResolution.failed)
                 if err.tag == "unauthorized" and isinstance(spec.config, AuthorizationCodeConfig):
                     # authorization_code's missing per-user token -> the per-server browser-OAuth
                     # challenge, built here where the full MCPServer is in hand.
@@ -3966,6 +4030,7 @@ class MCPServerManager:
         Returns:
             Configured MCP client instance.
         """
+        record_auth_resolution(server.server_id, AuthResolution.unresolved)
         resolved_server: Final = await self.ensure_oauth_metadata_discovered(server)
         transport: Final = resolved_server.transport or MCPTransport.sse
         spec = None if transport == MCPTransport.stdio else _to_server_spec_fail_closed(resolved_server)
@@ -4038,6 +4103,7 @@ class MCPServerManager:
                     env=resolved_env,
                 )
 
+            record_auth_resolution(server.server_id, AuthResolution.not_applicable)
             return MCPClient(
                 server_url="",  # Not used for stdio
                 transport_type=transport,
@@ -4092,6 +4158,20 @@ class MCPServerManager:
                     aws_session_name=resolved_server.aws_session_name,
                 )
 
+            legacy_source: Final = (
+                AuthResolution.aws_sigv4
+                if aws_auth is not None
+                else AuthResolution.extra_headers
+                if extra_headers and has_header(extra_headers, auth_header_name or "Authorization")
+                else AuthResolution.per_request_header
+                if mcp_auth_header
+                else AuthResolution.static_token
+                if auth_value
+                else AuthResolution.extra_headers
+                if extra_headers
+                else AuthResolution.no_auth
+            )
+            record_auth_resolution(server.server_id, legacy_source)
             return MCPClient(
                 server_url=server_url,
                 transport_type=transport,
@@ -6657,6 +6737,18 @@ class MCPServerManager:
                 last_health_check=datetime.now(),
             )
 
+        if server.spec_path:
+            spec_status, spec_error, spec_checked_at = await self._openapi_health_probes(server.spec_path).check()
+            return self._build_mcp_server_table(server).model_copy(
+                update=MappingProxyType(
+                    {
+                        "status": spec_status,
+                        "health_check_error": spec_error,
+                        "last_health_check": spec_checked_at,
+                    }
+                )
+            )
+
         status: Literal["healthy", "unhealthy", "unknown"] = "unknown"
         health_check_error = None
 
diff --git a/litellm/proxy/_experimental/mcp_server/oauth2_token_cache.py b/litellm/proxy/_experimental/mcp_server/oauth2_token_cache.py
index a4ef970b87a..42edc2999ab 100644
--- a/litellm/proxy/_experimental/mcp_server/oauth2_token_cache.py
+++ b/litellm/proxy/_experimental/mcp_server/oauth2_token_cache.py
@@ -28,6 +28,8 @@ from litellm.proxy._experimental.mcp_server.oauth_utils import (
     build_upstream_oauth2_token_request,
     resolve_upstream_resource,
 )
+from litellm.proxy._experimental.mcp_server.outbound_credentials.oauth_token_store import OAuthToken
+from litellm.proxy._experimental.mcp_server.outbound_credentials.token_cache_codec import OAuthTokenCacheCodec
 from litellm.proxy.common_utils.encrypt_decrypt_utils import (
     decrypt_value_helper,
     encrypt_value_helper,
@@ -233,8 +235,17 @@ class MCPPerUserTokenCache:
     def _cache_key(self, user_id: str, server_id: str) -> str:
         return f"{MCP_PER_USER_TOKEN_REDIS_KEY_PREFIX}:{user_id}:{server_id}"
 
+    def _codec(self) -> OAuthTokenCacheCodec:
+        return OAuthTokenCacheCodec(
+            encrypt_value_helper,
+            lambda blob: decrypt_value_helper(blob, key="mcp_per_user_token", exception_type="debug"),
+        )
+
     async def get(self, user_id: str, server_id: str) -> str | None:
-        """Return the plaintext access_token, or None on miss/error."""
+        token: Final = await self.get_token(user_id, server_id)
+        return token.access_token if token is not None else None
+
+    async def get_token(self, user_id: str, server_id: str) -> OAuthToken | None:
         try:
             from litellm.proxy.proxy_server import user_api_key_cache  # noqa: PLC0415
 
@@ -242,12 +253,7 @@ class MCPPerUserTokenCache:
             encrypted: Final = await user_api_key_cache.async_get_cache(key)
             if encrypted is None:
                 return None
-            plaintext: Final = decrypt_value_helper(
-                encrypted,
-                key="mcp_per_user_token",
-                exception_type="debug",
-            )
-            return plaintext or None
+            return self._codec().decode(encrypted)
         except Exception as exc:
             verbose_logger.debug(
                 "MCPPerUserTokenCache.get failed for user=%s server=%s: %s",
@@ -263,13 +269,16 @@ class MCPPerUserTokenCache:
         server_id: str,
         access_token: str,
         ttl: int,
+        identity_binding_proof: str | None = None,
     ) -> None:
         """Store NaCl-encrypted access_token in Redis with the given TTL."""
         try:
             from litellm.proxy.proxy_server import user_api_key_cache  # noqa: PLC0415
 
             key: Final = self._cache_key(user_id, server_id)
-            encrypted: Final = encrypt_value_helper(access_token)
+            encrypted: Final = self._codec().encode(
+                OAuthToken(access_token=access_token, identity_binding_proof=identity_binding_proof)
+            )
             await user_api_key_cache.async_set_cache(key, encrypted, ttl=ttl)
             verbose_logger.debug(
                 "MCPPerUserTokenCache.set: cached token for user=%s server=%s ttl=%ds",
diff --git a/litellm/proxy/_experimental/mcp_server/oauth_identity_binding.py b/litellm/proxy/_experimental/mcp_server/oauth_identity_binding.py
new file mode 100644
index 00000000000..f02e6c85d9b
--- /dev/null
+++ b/litellm/proxy/_experimental/mcp_server/oauth_identity_binding.py
@@ -0,0 +1,423 @@
+"""Per-user OAuth identity binding: verify the upstream OIDC principal matches the LiteLLM caller.
+
+Closes the confused-deputy gap where a browser authenticated upstream as one principal produces a
+token that the relay stores under a different, LiteLLM-authenticated principal: before the token
+endpoint returns, stores, or caches an exchanged token for an identity-bound server, the id_token
+is validated (signature via the pinned issuer's JWKS, issuer, audience, expiry) and its principal
+claim is compared to the caller's trusted LiteLLM identity. Mismatches fail closed in enforce mode
+and are logged in audit mode.
+"""
+
+import hashlib
+import hmac
+import json
+from collections.abc import Awaitable, Callable, Mapping, Sequence
+from dataclasses import dataclass
+from typing import Final, Literal, Protocol, TypeAlias
+
+import jwt
+from fastapi import HTTPException
+from jwt.types import Options
+from typing_extensions import assert_never
+
+from litellm._logging import verbose_logger
+from litellm.caching.in_memory_cache import InMemoryCache
+from litellm.llms.custom_httpx.http_handler import get_async_httpx_client
+from litellm.types.llms.custom_http import httpxSpecialProvider
+from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+_ALLOWED_ID_TOKEN_ALGORITHMS: Final = (
+    "RS256",
+    "RS384",
+    "RS512",
+    "ES256",
+    "ES384",
+    "ES512",
+    "PS256",
+    "PS384",
+    "PS512",
+)
+_JWKS_CACHE_TTL_SECONDS: Final = 3600
+_jwks_cache: Final = InMemoryCache(default_ttl=_JWKS_CACHE_TTL_SECONDS)
+
+JwksFetcher: TypeAlias = Callable[
+    [MCPOAuthIdentityBinding],  # mutable-ok: Callable parameter syntax requires a list
+    Awaitable[Sequence[Mapping[str, object]]],
+]
+CallerPrincipalLoader: TypeAlias = Callable[
+    [str, MCPOAuthIdentityBinding],  # mutable-ok: Callable parameter syntax requires a list
+    Awaitable[str | None],
+]
+
+
+@dataclass(frozen=True, slots=True)
+class VerifiedRefreshToken:
+    refresh_token: str
+    binding_proof: str
+
+
+StoredRefreshTokenLoader: TypeAlias = Callable[
+    [str, str, MCPOAuthIdentityBinding],  # mutable-ok: Callable parameter syntax requires a list
+    Awaitable[VerifiedRefreshToken | None],
+]
+
+_RejectionCode: TypeAlias = Literal["oauth_principal_mismatch", "oauth_identity_binding_failed"]
+
+
+@dataclass(frozen=True, slots=True)
+class _BindingRejection:
+    code: _RejectionCode
+    description: str
+
+
+@dataclass(frozen=True, slots=True)
+class RefreshOwnershipProven:
+    """The gateway itself unwrapped the upstream refresh token from a sealed per-user envelope."""
+
+
+@dataclass(frozen=True, slots=True)
+class RefreshTokenPresented:
+    refresh_token: str
+
+
+RefreshOwnership: TypeAlias = RefreshOwnershipProven | RefreshTokenPresented | None
+
+
+class BindingValidator(Protocol):
+    async def __call__(
+        self,
+        *,
+        server: MCPServer,
+        token_response: Mapping[str, object],
+        litellm_user_id: str | None,
+        grant_type: str,
+        refresh_ownership: RefreshOwnership,
+    ) -> str | None: ...
+
+
+async def _fetch_issuer_jwks(binding: MCPOAuthIdentityBinding) -> Sequence[Mapping[str, object]]:
+    jwks_url: Final[str] = binding.jwks_url or await _discover_jwks_url(binding.issuer)
+    cached: Final = await _jwks_cache.async_get_cache(jwks_url)
+    if isinstance(cached, list):
+        return cached
+    client: Final = get_async_httpx_client(llm_provider=httpxSpecialProvider.Oauth2Check)
+    response: Final = await client.get(jwks_url)
+    response.raise_for_status()
+    document: Final = response.json()
+    keys: Final = document.get("keys") if isinstance(document, dict) else None
+    if not isinstance(keys, list):
+        raise TypeError(f"JWKS document at {jwks_url} has no 'keys' array")
+    await _jwks_cache.async_set_cache(jwks_url, keys, ttl=_JWKS_CACHE_TTL_SECONDS)
+    return keys
+
+
+async def _discover_jwks_url(issuer: str) -> str:
+    discovery_url: Final = f"{issuer.rstrip('/')}/.well-known/openid-configuration"
+    client: Final = get_async_httpx_client(llm_provider=httpxSpecialProvider.Oauth2Check)
+    response: Final = await client.get(discovery_url)
+    response.raise_for_status()
+    metadata: Final = response.json()
+    jwks_uri: Final = metadata.get("jwks_uri") if isinstance(metadata, dict) else None
+    if not isinstance(jwks_uri, str) or not jwks_uri:
+        raise ValueError(f"OIDC discovery at {discovery_url} returned no jwks_uri")
+    return jwks_uri
+
+
+def _select_signing_key(id_token: str, keys: Sequence[Mapping[str, object]]) -> "jwt.PyJWK | _BindingRejection":
+    header: Final = jwt.get_unverified_header(id_token)
+    kid: Final = header.get("kid")
+    for key in keys:
+        if kid is None or key.get("kid") == kid:
+            return jwt.PyJWK(dict(key))  # mutable-ok: PyJWT requires a concrete JWK dictionary
+    return _BindingRejection(
+        code="oauth_identity_binding_failed",
+        description=f"id_token signing key (kid={kid!r}) not found in the issuer's JWKS",
+    )
+
+
+def _decode_id_token(
+    id_token: str,
+    binding: MCPOAuthIdentityBinding,
+    signing_key: "jwt.PyJWK",
+) -> "Mapping[str, object] | _BindingRejection":
+    try:
+        decode_options: Final[Options] = {"require": ("iss", "exp", "aud", "sub", "iat")}
+        return jwt.decode(
+            id_token,
+            signing_key.key,
+            algorithms=_ALLOWED_ID_TOKEN_ALGORITHMS,
+            issuer=binding.issuer,
+            audience=binding.audiences,
+            options=decode_options,
+        )
+    except jwt.InvalidTokenError as exc:
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description=f"id_token validation failed: {exc}",
+        )
+
+
+def _upstream_principal(
+    claims: Mapping[str, object],
+    binding: MCPOAuthIdentityBinding,
+) -> "str | _BindingRejection":
+    principal: Final = claims.get(binding.principal_claim)
+    if not isinstance(principal, str) or not principal:
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description=f"id_token has no usable '{binding.principal_claim}' claim",
+        )
+    if (
+        binding.principal_claim == "email"
+        and binding.require_email_verified
+        and claims.get("email_verified") is not True
+    ):
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description="id_token email is not verified (email_verified is not true)",
+        )
+    return principal
+
+
+async def _load_caller_principal(litellm_user_id: str, binding: MCPOAuthIdentityBinding) -> str | None:
+    if binding.caller_field == "user_id":
+        return litellm_user_id
+    from litellm.proxy._experimental.mcp_server.bridge_token_flow import (  # noqa: PLC0415  # inline import avoids a module-load circular import
+        load_active_user_by_id,
+    )
+
+    loaded: Final = await load_active_user_by_id(litellm_user_id)
+    if isinstance(loaded, str):
+        return None
+    return loaded.user_email
+
+
+async def _load_stored_refresh_token(
+    litellm_user_id: str, server_id: str, binding: MCPOAuthIdentityBinding
+) -> VerifiedRefreshToken | None:
+    try:
+        from litellm.proxy._experimental.mcp_server.db import (  # noqa: PLC0415  # keep database imports lazy
+            get_user_oauth_credential,
+        )
+        from litellm.proxy.utils import get_prisma_client_or_throw  # noqa: PLC0415  # keep database imports lazy
+
+        prisma_client: Final = get_prisma_client_or_throw(
+            "Database not connected. Cannot verify OAuth refresh token ownership."
+        )
+        cred: Final = await get_user_oauth_credential(
+            prisma_client=prisma_client,
+            user_id=litellm_user_id,
+            server_id=server_id,
+        )
+        if not cred or not await credential_binding_matches(binding, litellm_user_id, server_id, cred):
+            return None
+        refresh_token: Final = cred.get("refresh_token")
+        proof: Final = cred.get("identity_binding_proof")
+        return VerifiedRefreshToken(refresh_token, proof) if refresh_token and proof else None
+    except Exception:  # noqa: BLE001  # a credential lookup failure must fail closed
+        return None
+
+
+async def current_binding_proof(
+    binding: MCPOAuthIdentityBinding,
+    user_id: str,
+    server_id: str,
+    caller_principal_loader: CallerPrincipalLoader = _load_caller_principal,
+) -> str | None:
+    principal: Final = await caller_principal_loader(user_id, binding)
+    if not principal:
+        return None
+    return _binding_proof(binding, user_id, server_id, principal)
+
+
+def _binding_proof(binding: MCPOAuthIdentityBinding, user_id: str, server_id: str, principal: str) -> str:
+    payload: Final = json.dumps(
+        ("oidc-nonce-v1", server_id, user_id, principal, binding.model_dump(mode="json")),
+        sort_keys=True,
+    )
+    return hashlib.sha256(payload.encode()).hexdigest()
+
+
+async def credential_binding_matches(
+    binding: MCPOAuthIdentityBinding,
+    user_id: str,
+    server_id: str,
+    credential: Mapping[str, object],
+    caller_principal_loader: CallerPrincipalLoader = _load_caller_principal,
+) -> bool:
+    stored: Final = credential.get("identity_binding_proof")
+    if not isinstance(stored, str) or not stored:
+        return False
+    expected: Final = await current_binding_proof(binding, user_id, server_id, caller_principal_loader)
+    return expected is not None and hmac.compare_digest(stored, expected)
+
+
+def _principals_match(upstream: str, caller: str, binding: MCPOAuthIdentityBinding) -> bool:
+    if binding.principal_claim == "email" or binding.caller_field == "user_email":
+        return upstream.strip().casefold() == caller.strip().casefold()
+    return upstream == caller
+
+
+async def _evaluate_refresh_ownership(
+    binding: MCPOAuthIdentityBinding,
+    litellm_user_id: str | None,
+    server_id: str,
+    refresh_ownership: RefreshOwnership,
+    stored_refresh_token_loader: StoredRefreshTokenLoader,
+) -> _BindingRejection | str:
+    match refresh_ownership:
+        case RefreshOwnershipProven():
+            return _BindingRejection(
+                code="oauth_identity_binding_failed",
+                description="an identity envelope alone does not prove upstream principal binding",
+            )
+        case None:
+            return _BindingRejection(
+                code="oauth_identity_binding_failed",
+                description="refresh_token grant without an id_token carries no refresh token to prove ownership of",
+            )
+        case RefreshTokenPresented(refresh_token):
+            if not litellm_user_id:
+                return _BindingRejection(
+                    code="oauth_identity_binding_failed",
+                    description="the request carries no resolvable LiteLLM user identity to bind the credential to",
+                )
+            stored: Final = await stored_refresh_token_loader(litellm_user_id, server_id, binding)
+            if stored is None or not hmac.compare_digest(stored.refresh_token, refresh_token):
+                return _BindingRejection(
+                    code="oauth_identity_binding_failed",
+                    description="the presented refresh_token is not the caller's stored credential for this server",
+                )
+            return stored.binding_proof
+    assert_never(refresh_ownership)  # pragma: no cover
+
+
+async def _evaluate_binding(
+    binding: MCPOAuthIdentityBinding,
+    token_response: Mapping[str, object],
+    litellm_user_id: str | None,
+    grant_type: str,
+    server_id: str,
+    refresh_ownership: RefreshOwnership,
+    jwks_fetcher: JwksFetcher,
+    caller_principal_loader: CallerPrincipalLoader,
+    stored_refresh_token_loader: StoredRefreshTokenLoader,
+    expected_nonce: str | None,
+) -> _BindingRejection | str:
+    id_token: Final = token_response.get("id_token")
+    if not isinstance(id_token, str) or not id_token:
+        if grant_type != "refresh_token":
+            return _BindingRejection(
+                code="oauth_identity_binding_failed",
+                description="the upstream token response carries no id_token to bind the credential to a principal",
+            )
+        return await _evaluate_refresh_ownership(
+            binding,
+            litellm_user_id,
+            server_id,
+            refresh_ownership,
+            stored_refresh_token_loader,
+        )
+    if not litellm_user_id:
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description="the request carries no resolvable LiteLLM user identity to bind the credential to",
+        )
+    try:
+        keys: Final = await jwks_fetcher(binding)
+    except Exception as exc:  # noqa: BLE001  # a JWKS fetch failure must fail closed, not surface as a 500
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description=f"could not fetch the issuer's JWKS: {exc}",
+        )
+    try:
+        signing_key: Final = _select_signing_key(id_token, keys)
+    except (jwt.PyJWTError, ValueError, TypeError):
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description="invalid id_token header or issuer signing key",
+        )
+    if isinstance(signing_key, _BindingRejection):
+        return signing_key
+    claims: Final = _decode_id_token(id_token, binding, signing_key)
+    if isinstance(claims, _BindingRejection):
+        return claims
+    if grant_type == "authorization_code" and (binding.mode == "enforce" or expected_nonce is not None):
+        nonce: Final = claims.get("nonce")
+        if not expected_nonce or not isinstance(nonce, str) or not hmac.compare_digest(nonce, expected_nonce):
+            return _BindingRejection(
+                code="oauth_identity_binding_failed",
+                description="id_token nonce does not match the authenticated authorization transaction",
+            )
+    upstream: Final = _upstream_principal(claims, binding)
+    if isinstance(upstream, _BindingRejection):
+        return upstream
+    caller: Final = await caller_principal_loader(litellm_user_id, binding)
+    if not caller:
+        return _BindingRejection(
+            code="oauth_identity_binding_failed",
+            description=f"the LiteLLM user has no '{binding.caller_field}' to compare the upstream principal against",
+        )
+    if not _principals_match(upstream, caller, binding):
+        return _BindingRejection(
+            code="oauth_principal_mismatch",
+            description="The browser account does not match the selected credential owner.",
+        )
+    return _binding_proof(binding, litellm_user_id, server_id, caller)
+
+
+async def enforce_oauth_identity_binding(
+    server: MCPServer,
+    token_response: Mapping[str, object],
+    litellm_user_id: str | None,
+    grant_type: str,
+    refresh_ownership: RefreshOwnership,
+    jwks_fetcher: JwksFetcher = _fetch_issuer_jwks,
+    caller_principal_loader: CallerPrincipalLoader = _load_caller_principal,
+    stored_refresh_token_loader: StoredRefreshTokenLoader = _load_stored_refresh_token,
+    expected_nonce: str | None = None,
+) -> str | None:
+    """Validate the exchanged token's upstream principal against the LiteLLM caller.
+
+    No-op when the server has no binding or it is disabled. In enforce mode a failure raises 403
+    before the caller returns, stores, or caches the token; in audit mode failures are logged only.
+    A refresh_token grant without an id_token is allowed only when the presented refresh token matches
+    the caller's stored credential and that credential was previously identity-validated.
+    """
+    binding: Final = server.oauth_identity_binding
+    if binding is None or binding.mode not in ("audit", "enforce"):
+        return
+    rejection: Final = await _evaluate_binding(
+        binding=binding,
+        token_response=token_response,
+        litellm_user_id=litellm_user_id,
+        grant_type=grant_type,
+        server_id=server.server_id,
+        refresh_ownership=refresh_ownership,
+        jwks_fetcher=jwks_fetcher,
+        caller_principal_loader=caller_principal_loader,
+        stored_refresh_token_loader=stored_refresh_token_loader,
+        expected_nonce=expected_nonce,
+    )
+    if isinstance(rejection, str):
+        return rejection if binding.mode == "enforce" else None
+    if binding.mode == "audit":
+        verbose_logger.warning(
+            "oauth_identity_binding audit: server=%s user=%s grant=%s rejected=%s (%s)",
+            server.server_id,
+            litellm_user_id,
+            grant_type,
+            rejection.code,
+            rejection.description,
+        )
+        return
+    raise HTTPException(
+        status_code=403,
+        detail={
+            "error": rejection.code,
+            "error_description": rejection.description,
+            "server_id": server.server_id,
+            "credential_owner": "caller",
+            "credential_stored": False,
+        },
+    )
diff --git a/litellm/proxy/_experimental/mcp_server/openapi_to_mcp_generator.py b/litellm/proxy/_experimental/mcp_server/openapi_to_mcp_generator.py
index 16f58ef5b76..d115eb8b3c1 100644
--- a/litellm/proxy/_experimental/mcp_server/openapi_to_mcp_generator.py
+++ b/litellm/proxy/_experimental/mcp_server/openapi_to_mcp_generator.py
@@ -163,10 +163,14 @@ def load_openapi_spec(filepath: str) -> dict[str, Any]:
     return asyncio.run(load_openapi_spec_async(filepath))
 
 
-async def load_openapi_spec_async(filepath: str) -> dict[str, Any]:
+async def load_openapi_spec_async(filepath: str, *, max_bytes: int | None = None) -> dict[str, Any]:
     if filepath.startswith("http://") or filepath.startswith("https://"):
         client: Final = get_async_httpx_client(llm_provider=httpxSpecialProvider.MCP)
-        r: Final[httpx.Response] = await async_safe_get(client, filepath)
+        r: Final[httpx.Response] = (
+            await async_safe_get(client, filepath)
+            if max_bytes is None
+            else await async_safe_get(client, filepath, max_response_bytes=max_bytes)
+        )
         r.raise_for_status()
         return r.json()
 
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/authz_code_refresher.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/authz_code_refresher.py
index 92bd30694af..af1e82eab82 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/authz_code_refresher.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/authz_code_refresher.py
@@ -14,10 +14,17 @@ import time
 from collections.abc import Awaitable, Callable
 from typing import TYPE_CHECKING, Final, Protocol
 
+from fastapi import HTTPException
+
 from litellm._logging import verbose_logger
 from litellm.proxy._experimental.mcp_server.auth.token_endpoint_auth import (
     TokenEndpointAuthConfigError,
 )
+from litellm.proxy._experimental.mcp_server.oauth_identity_binding import (
+    BindingValidator,
+    RefreshTokenPresented,
+    enforce_oauth_identity_binding,
+)
 from litellm.proxy._experimental.mcp_server.oauth_utils import build_upstream_oauth2_token_request
 from litellm.proxy._experimental.mcp_server.outbound_credentials.oauth_token_store import (
     OAuthToken,
@@ -39,6 +46,7 @@ class CredentialPersist(Protocol):
         refresh_token: str | None,
         expires_in: int | None,
         scopes: tuple[str, ...] | None,
+        identity_binding_proof: str | None = None,
     ) -> None: ...
 
 
@@ -78,13 +86,23 @@ class AuthorizationCodeRefresher:
         persist: CredentialPersist,
         *,
         clock: Callable[[], float] = time.time,
+        identity_validator: BindingValidator = enforce_oauth_identity_binding,
     ) -> None:
         self._server_lookup = server_lookup
         self._token_endpoint = token_endpoint
         self._persist = persist
         self._clock = clock
+        self._identity_validator = identity_validator
 
     async def refresh(self, user_id: str, server_id: str, token: OAuthToken) -> OAuthToken | None:
+        try:
+            return await self._refresh(user_id, server_id, token)
+        except HTTPException as exc:
+            if exc.status_code != 403:
+                raise
+            return None
+
+    async def _refresh(self, user_id: str, server_id: str, token: OAuthToken) -> OAuthToken | None:
         if token.refresh_token is None:
             return None
         server: Final = self._server_lookup(server_id)
@@ -104,6 +122,15 @@ class AuthorizationCodeRefresher:
         except TokenEndpointAuthConfigError as exc:
             verbose_logger.warning("MCP OAuth refresh misconfigured for server %s: %s", server_id, exc)
             return None
+        binding: Final = server.oauth_identity_binding
+        if binding is not None and binding.mode == "enforce":
+            await self._identity_validator(
+                server=server,
+                token_response={},
+                litellm_user_id=user_id,
+                grant_type="refresh_token",
+                refresh_ownership=RefreshTokenPresented(token.refresh_token),
+            )
         form: Final = {
             "grant_type": "refresh_token",
             "refresh_token": token.refresh_token,
@@ -116,15 +143,34 @@ class AuthorizationCodeRefresher:
         if not isinstance(access_token, str) or not access_token:
             return None
 
+        binding_proof: Final = await self._identity_validator(
+            server=server,
+            token_response=body,
+            litellm_user_id=user_id,
+            grant_type="refresh_token",
+            refresh_ownership=RefreshTokenPresented(token.refresh_token),
+        )
         rotated: Final = body.get("refresh_token")
         new_refresh: Final = rotated if isinstance(rotated, str) and rotated else token.refresh_token
         expires_in: Final = _parse_expires_in(body.get("expires_in"))
         scopes: Final = _parse_scopes(body.get("scope")) or token.scopes
 
-        await self._persist(user_id, server_id, access_token, new_refresh, expires_in, scopes or None)
+        if binding_proof is not None:
+            await self._persist(
+                user_id,
+                server_id,
+                access_token,
+                new_refresh,
+                expires_in,
+                scopes or None,
+                identity_binding_proof=binding_proof,
+            )
+        else:
+            await self._persist(user_id, server_id, access_token, new_refresh, expires_in, scopes or None)
         return OAuthToken(
             access_token=access_token,
             expires_at=self._clock() + expires_in if expires_in is not None else None,
             refresh_token=new_refresh,
             scopes=scopes,
+            identity_binding_proof=binding_proof,
         )
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/oauth_token_store.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/oauth_token_store.py
index e0cd9e8e5ed..0ac4296f498 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/oauth_token_store.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/oauth_token_store.py
@@ -41,6 +41,7 @@ class OAuthToken:
     expires_at: float | None = None
     refresh_token: str | None = None
     scopes: tuple[str, ...] = ()
+    identity_binding_proof: str | None = None
 
     def __repr__(self) -> str:
         has_refresh: Final = self.refresh_token is not None
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/per_user_oauth_store.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/per_user_oauth_store.py
index 5e28396dcfb..2897c3e8e4a 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/per_user_oauth_store.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/per_user_oauth_store.py
@@ -12,9 +12,11 @@ from __future__ import annotations
 
 import asyncio
 from collections.abc import Callable, Mapping
+from functools import partial
 from typing import TYPE_CHECKING, Final
 
 from litellm._logging import verbose_logger
+from litellm.proxy._experimental.mcp_server.oauth_identity_binding import credential_binding_matches
 from litellm.proxy._experimental.mcp_server.outbound_credentials.authz_code_refresher import (
     AuthorizationCodeRefresher,
 )
@@ -69,6 +71,7 @@ async def _persist_credential(
     refresh_token: str | None,
     expires_in: int | None,
     scopes: tuple[str, ...] | None,
+    identity_binding_proof: str | None = None,
 ) -> None:
     from litellm.proxy._experimental.mcp_server.db import (  # noqa: PLC0415
         store_user_oauth_credential,
@@ -86,6 +89,7 @@ async def _persist_credential(
         expires_in=expires_in,
         scopes=list(scopes) if scopes else None,
         skip_byok_guard=True,
+        identity_binding_proof=identity_binding_proof,
     )
 
 
@@ -142,12 +146,26 @@ def _runtime_backend_and_coordinator() -> tuple[TokenCacheBackend | None, Refres
     return backend, coordinator, True
 
 
+async def _read_bound_credential(
+    server_lookup: ServerLookup, user_id: str, server_id: str
+) -> Mapping[str, object] | None:
+    credential: Final = await _read_credential(user_id, server_id)
+    server: Final = server_lookup(server_id)
+    binding: Final = server.oauth_identity_binding if server else None
+    if credential is not None and binding is not None and binding.mode == "enforce":
+        if not await credential_binding_matches(binding, user_id, server_id, credential):
+            return None
+    return credential
+
+
 def _build_per_user_oauth_token_store(
     server_lookup: ServerLookup,
 ) -> tuple[CachedOAuthTokenStore, bool]:
     backend, coordinator, uses_redis = _runtime_backend_and_coordinator()
     refresher: Final = AuthorizationCodeRefresher(server_lookup, _post_token_endpoint, _persist_credential)
-    refreshing: Final = RefreshingTokenStore(V2PerUserTokenStore(_read_credential), refresher, coordinator=coordinator)
+    refreshing: Final = RefreshingTokenStore(
+        V2PerUserTokenStore(partial(_read_bound_credential, server_lookup)), refresher, coordinator=coordinator
+    )
     return CachedOAuthTokenStore(refreshing, default_ttl_seconds=_DEFAULT_TTL_SECONDS, backend=backend), uses_redis
 
 
@@ -182,6 +200,18 @@ class LazyPerUserOAuthTokenStore:
         self._local_fetches = 0
 
     async def fetch(self, user_id: str, server_id: str) -> OAuthToken | None:
+        token: Final = await self._fetch_token(user_id, server_id)
+        server: Final = self._server_lookup(server_id)
+        binding: Final = server.oauth_identity_binding if server else None
+        if token is not None and binding is not None and binding.mode == "enforce":
+            if not await credential_binding_matches(
+                binding, user_id, server_id, {"identity_binding_proof": token.identity_binding_proof}
+            ):
+                await self.invalidate(user_id, server_id)
+                return None
+        return token
+
+    async def _fetch_token(self, user_id: str, server_id: str) -> OAuthToken | None:
         if self._uses_redis:
             store = self._store
             if store is not None:
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/resolver.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/resolver.py
index 8328aae01ab..85c7f68719d 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/resolver.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/resolver.py
@@ -65,6 +65,7 @@ from litellm.proxy._experimental.mcp_server.outbound_credentials.token_exchanger
 from litellm.proxy._experimental.mcp_server.outbound_credentials.types import (
     ApiKeyConfig,
     AuthorizationCodeConfig,
+    AuthResolution,
     AuthSpecKind,
     AwsSigV4Config,
     Byok,
@@ -76,6 +77,7 @@ from litellm.proxy._experimental.mcp_server.outbound_credentials.types import (
     NoneConfig,
     PassthroughConfig,
     PrivateKeyJwtAuth,
+    ResolvedCredential,
     ServerSpec,
     SharedKey,
     Subject,
@@ -448,3 +450,32 @@ def _client_auth_fingerprint(client_auth: ClientAuth) -> str:
 
 def _not_implemented(kind: AuthSpecKind) -> Result[httpx.Auth, CredError]:
     return Error(CredError.of_not_implemented(f"{kind.value}: resolver arm not implemented yet"))
+
+
+async def resolve_credentials_with_source(
+    provider: UpstreamCredentialProvider, subject: Subject, server: ServerSpec
+) -> Result[ResolvedCredential, CredError]:
+    match await provider.resolve_credentials(subject, server):
+        case Error(err):
+            return Error(err)
+        case Ok(auth):
+            if isinstance(auth, NoOpAuth):
+                return Ok(ResolvedCredential(auth, AuthResolution.no_auth))
+            match server.config:
+                case NoneConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.no_auth))
+                case ApiKeyConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.static_token))
+                case PassthroughConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.oauth2_passthrough))
+                case ClientCredentialsConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.client_credentials))
+                case TokenExchangeConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.token_exchange))
+                case IdJagConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.id_jag))
+                case AuthorizationCodeConfig():
+                    return Ok(ResolvedCredential(auth, AuthResolution.stored_user_token))
+                case AwsSigV4Config():
+                    return Ok(ResolvedCredential(auth, AuthResolution.aws_sigv4))
+            assert_never(server.config)
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/token_cache_codec.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/token_cache_codec.py
index 14cc309b685..56dc3f19cdd 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/token_cache_codec.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/token_cache_codec.py
@@ -1,24 +1,26 @@
 """Serialize + encrypt boundary for caching an OAuth token in a shared (Redis) cache.
 
-A cross-replica cache must serialize the token, and a plaintext bearer in Redis is a leak, so this
-encrypts the value (NaCl in production via the injected ``encrypt``, identity in tests). It caches
-**only** the ``access_token``: the hot path needs just the bearer, expiry is carried by the cache
-entry's TTL (set from the token's ``expires_at`` by the cache), and the long-lived refresh_token stays
-in the DB - the refresh path is always a cache miss that re-reads it - so it never reaches Redis. A
-decoded token therefore carries only the bearer (``expires_at`` and ``refresh_token`` both None); the
-TTL, not the value, bounds its life. An empty/undecryptable blob (e.g. master-key rotation) is a miss.
+Shared cache values contain an encrypted access token and optional identity-binding proof.
+Refresh tokens remain in the database; cache TTL bounds the access token's lifetime.
+Legacy bearer-only entries decode without proof and cannot satisfy identity enforcement.
 """
 
 from __future__ import annotations
 
+import json
 from collections.abc import Callable
 from dataclasses import dataclass
 from typing import Final
 
+from pydantic import TypeAdapter, ValidationError
+
 from litellm.proxy._experimental.mcp_server.outbound_credentials.oauth_token_store import (
     OAuthToken,
 )
 
+_BOUND_PREFIX: Final = "litellm-bound-oauth-v1:"
+_BOUND_PAYLOAD: Final = TypeAdapter(dict[str, str])
+
 
 @dataclass(frozen=True, slots=True)
 class OAuthTokenCacheCodec:
@@ -26,10 +28,30 @@ class OAuthTokenCacheCodec:
     decrypt: Callable[[str], str | None]
 
     def encode(self, token: OAuthToken) -> str:
+        if token.identity_binding_proof is not None:
+            return self.encrypt(
+                _BOUND_PREFIX
+                + json.dumps(
+                    {
+                        "access_token": token.access_token,
+                        "identity_binding_proof": token.identity_binding_proof,
+                    }
+                )
+            )
         return self.encrypt(token.access_token)
 
     def decode(self, blob: str) -> OAuthToken | None:
         access_token: Final = self.decrypt(blob)
         if not access_token:
             return None
+        if access_token.startswith(_BOUND_PREFIX):
+            try:
+                payload: Final = _BOUND_PAYLOAD.validate_json(access_token[len(_BOUND_PREFIX) :])
+            except ValidationError:
+                return None
+            bearer: Final = payload.get("access_token")
+            proof: Final = payload.get("identity_binding_proof")
+            if not bearer or not proof:
+                return None
+            return OAuthToken(access_token=bearer, identity_binding_proof=proof)
         return OAuthToken(access_token=access_token, refresh_token=None)
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/types.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/types.py
index 632dc57dcf6..d186724fd9f 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/types.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/types.py
@@ -26,10 +26,11 @@ union (see `result.py`), not `expression.Result`.
 from __future__ import annotations
 
 from collections.abc import Mapping
-from dataclasses import dataclass
+from dataclasses import dataclass, field
 from enum import Enum
 from typing import Annotated, Final, Literal
 
+import httpx
 from expression import case, tag, tagged_union
 from pydantic import BaseModel, ConfigDict, Field, SecretStr, field_validator
 from typing_extensions import assert_never
@@ -46,6 +47,29 @@ from litellm.types.mcp import (
 )
 
 
+class AuthResolution(str, Enum):
+    no_auth = "no-auth"
+    stored_user_token = "stored-user-token"
+    static_token = "static-token"
+    per_request_header = "per-request-header"
+    oauth2_passthrough = "oauth2-passthrough"
+    client_credentials = "m2m-client-credentials"
+    token_exchange = "token-exchange"
+    id_jag = "id-jag"
+    aws_sigv4 = "aws-sigv4"
+    extra_headers = "extra-headers"
+    not_applicable = "not-applicable"
+    unresolved = "unresolved"
+    failed = "resolution-failed"
+    multiple = "multiple"
+
+
+@dataclass(frozen=True, slots=True)
+class ResolvedCredential:
+    auth: httpx.Auth = field(repr=False)
+    source: AuthResolution
+
+
 class AuthSpecKind(str, Enum):
     """The server's statically-declared upstream-auth mode — derived from its `config`.
 
diff --git a/litellm/proxy/_experimental/mcp_server/outbound_credentials/v2_token_store.py b/litellm/proxy/_experimental/mcp_server/outbound_credentials/v2_token_store.py
index 4d88ec8b025..0f18931d118 100644
--- a/litellm/proxy/_experimental/mcp_server/outbound_credentials/v2_token_store.py
+++ b/litellm/proxy/_experimental/mcp_server/outbound_credentials/v2_token_store.py
@@ -46,11 +46,13 @@ def _to_oauth_token(payload: Mapping[str, object]) -> OAuthToken | None:
         return None
     refresh_token: Final = payload.get("refresh_token")
     expires_at: Final = payload.get("expires_at")
+    binding_proof: Final = payload.get("identity_binding_proof")
     return OAuthToken(
         access_token=access_token,
         expires_at=_iso_to_epoch(expires_at) if isinstance(expires_at, str) else None,
         refresh_token=refresh_token if isinstance(refresh_token, str) else None,
         scopes=_to_scopes(payload.get("scopes")),
+        identity_binding_proof=binding_proof if isinstance(binding_proof, str) else None,
     )
 
 
diff --git a/litellm/proxy/_experimental/mcp_server/rest_endpoints.py b/litellm/proxy/_experimental/mcp_server/rest_endpoints.py
index 384a1858545..8ddfd63bcb6 100644
--- a/litellm/proxy/_experimental/mcp_server/rest_endpoints.py
+++ b/litellm/proxy/_experimental/mcp_server/rest_endpoints.py
@@ -3,12 +3,15 @@ import importlib
 from collections.abc import Awaitable, Callable, Mapping, Sequence
 from dataclasses import dataclass
 from datetime import datetime
+from traceback import walk_tb
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Literal
+from uuid import uuid4
 
 import anyio
 import httpx
 from fastapi import APIRouter, Depends, HTTPException, Query, Request, status
+from pydantic import ValidationError
 from starlette.datastructures import Headers
 
 from litellm._logging import verbose_logger
@@ -30,6 +33,8 @@ from litellm.proxy._experimental.mcp_server.faults.list_outcomes import (
     list_fault_http_status,
     outcome_wire_value,
 )
+from litellm.proxy._experimental.mcp_server.faults.traversal import iter_exception_tree
+from litellm.proxy._experimental.mcp_server.oauth_utils import _redact_mcp_resource_url
 from litellm.proxy._experimental.mcp_server.ui_session_utils import (
     acting_user_auth,
     build_effective_auth_contexts,
@@ -78,11 +83,39 @@ _MCP_GUARDRAIL_REJECTIONS: Final = (
 
 
 def _connection_error_message(exc: BaseException, url: str | None, timeout_seconds: float) -> str:
+    reference: Final = uuid4().hex
+    verbose_logger.error(
+        "MCP connection test failed (reference=%s): %s",
+        reference,
+        tuple(
+            (
+                type(cause).__name__,
+                tuple(
+                    (frame.f_code.co_filename, lineno, frame.f_code.co_name)
+                    for frame, lineno in walk_tb(cause.__traceback__)
+                ),
+            )
+            for cause in iter_exception_tree(exc)
+        ),
+    )
+    return next(
+        (
+            message
+            for cause in iter_exception_tree(exc)
+            if (message := _known_connection_error_message(cause, url, timeout_seconds)) is not None
+        ),
+        "An unexpected error occurred while testing the MCP connection. "
+        f"Retry; if it persists, share reference {reference} with your gateway administrator.",
+    )
+
+
+def _known_connection_error_message(exc: BaseException, url: str | None, timeout_seconds: float) -> str | None:
     if isinstance(exc, MCPServerURLCredentialsError):
         return str(exc.detail)
     if isinstance(exc, TimeoutError):
         return (
-            f"Failed to connect to MCP server: no response from {url or 'the server'} "
+            "Failed to connect to MCP server: no valid MCP response received from "
+            f"{_redact_mcp_resource_url(url) or 'the server'} "
             f"within {timeout_seconds:.0f}s. Check that the LiteLLM proxy can reach this URL "
             "from its network (DNS, egress rules, firewalls) and that the server answers MCP requests."
         )
@@ -99,13 +132,45 @@ def _connection_error_message(exc: BaseException, url: str | None, timeout_secon
         return "Failed to connect to MCP server: the connection timed out."
     if isinstance(exc, httpx.HTTPStatusError):
         return f"Failed to connect to MCP server: it returned HTTP {exc.response.status_code}."
-    return "Failed to connect to MCP server. Check proxy logs for details."
+    if isinstance(exc, (httpx.NetworkError, httpx.RemoteProtocolError, ConnectionError)):
+        return (
+            "Failed to connect to MCP server: the connection was interrupted. "
+            "Check the server and network connection, then retry."
+        )
+    if isinstance(exc, ValueError) and str(exc).startswith("Unexpected content type:"):
+        return (
+            "Failed to connect to MCP server: the endpoint returned an unsupported content type. "
+            "Check that the URL is an MCP endpoint, not a web page, and matches the selected transport."
+        )
+    if isinstance(exc, ValidationError) and exc.title in ("JSONRPCMessage", "InitializeResult", "ListToolsResult"):
+        return (
+            "Failed to connect to MCP server: the endpoint returned invalid JSON or an invalid MCP response. "
+            "Check the MCP endpoint URL and the server's protocol implementation."
+        )
+    if MCP_AVAILABLE and isinstance(exc, McpError):
+        if exc.error.code == -32000 and exc.error.message == "Connection closed":
+            return (
+                "Failed to connect to MCP server: the connection was closed before the request completed. "
+                "Check that the server stays running and returns a complete MCP response, then retry."
+            )
+        if exc.error.code == 32600 and exc.error.message == "Session terminated":
+            return (
+                "Failed to connect to MCP server: the MCP session was terminated. "
+                "Check that the URL points to an MCP endpoint and matches the selected transport, "
+                "then retry to start a new session."
+            )
+        return (
+            f"Failed to connect to MCP server: the MCP request failed (JSON-RPC code {exc.error.code}). "
+            "Check that the endpoint supports MCP initialization and tool listing, and check the upstream server logs."
+        )
+    return None
 
 
 if MCP_AVAILABLE:
+    from mcp.shared.exceptions import McpError
     from mcp.types import Tool as MCPTool
 
-    from litellm.experimental_mcp_client.client import MCPClient
+    from litellm.experimental_mcp_client.client import MCPClient, as_mcp_read_timeout
     from litellm.llms.litellm_proxy.skills.skill_search import (
         DEFAULT_SKILL_SEARCH_TOP_K,
     )
@@ -1171,7 +1236,7 @@ if MCP_AVAILABLE:
         return client_id, client_secret, scopes
 
     _STAGED_AUTH_VALUE_AUTH_TYPES: Final = frozenset(
-        (MCPAuth.api_key, MCPAuth.bearer_token, MCPAuth.basic, MCPAuth.authorization)
+        (MCPAuth.api_key, MCPAuth.bearer_token, MCPAuth.basic, MCPAuth.authorization, MCPAuth.token)
     )
 
     @dataclass(frozen=True, slots=True)
@@ -1180,6 +1245,17 @@ if MCP_AVAILABLE:
         mcp_auth_header: str | None
         oauth2_headers: dict[str, str] | None
 
+    def _preview_origin(url: str | None) -> tuple[str, str, int | None] | None:
+        if not url:
+            return None
+        try:
+            parsed: Final = httpx.URL(url)
+        except httpx.InvalidURL:
+            return None
+        if parsed.scheme not in ("http", "https") or not parsed.host:
+            return None
+        return parsed.scheme, parsed.host, parsed.port
+
     def _stage_server_test(new_mcp_server_request: NewMCPServerRequest, headers: Headers) -> _StagedServerTest:
         """
         Resolve the credentials a not-yet-saved server config carries for a preview call.
@@ -1192,7 +1268,19 @@ if MCP_AVAILABLE:
             MCPRequestHandler,
         )
 
-        request: Final = _inherit_credentials_from_existing_server(new_mcp_server_request)
+        saved_server: Final = (
+            global_mcp_server_manager.get_mcp_server_by_id(new_mcp_server_request.server_id)
+            if new_mcp_server_request.server_id
+            else None
+        )
+        saved_origin: Final = _preview_origin(saved_server.url) if saved_server else None
+        preview_origin: Final = _preview_origin(new_mcp_server_request.url)
+        may_inherit: Final = new_mcp_server_request.auth_type not in _STAGED_AUTH_VALUE_AUTH_TYPES or (
+            saved_origin is not None and saved_origin == preview_origin
+        )
+        request: Final = (
+            _inherit_credentials_from_existing_server(new_mcp_server_request) if may_inherit else new_mcp_server_request
+        )
         mcp_auth_header: Final = (
             request.credentials.get("auth_value")
             if request.auth_type in _STAGED_AUTH_VALUE_AUTH_TYPES and isinstance(request.credentials, dict)
@@ -1255,8 +1343,15 @@ if MCP_AVAILABLE:
             if _oauth2_flow == "client_credentials" and not request.token_url:
                 _oauth2_flow = None
 
+            # Static previews inherit credentials before this step, but must not resolve back to
+            # the saved record during client creation and discard the edited connection settings.
+            preview_server_id: Final = (
+                ""
+                if request.auth_type in _STAGED_AUTH_VALUE_AUTH_TYPES or request.auth_type in (None, MCPAuth.none)
+                else request.server_id or ""
+            )
             server_model: Final = MCPServer(
-                server_id=request.server_id or "",
+                server_id=preview_server_id,
                 name=request.alias or request.server_name or "",
                 url=request.url,
                 transport=request.transport,
@@ -1344,11 +1439,18 @@ if MCP_AVAILABLE:
         except (KeyboardInterrupt, SystemExit, asyncio.CancelledError):
             raise
         except BaseException as e:
-            verbose_logger.error("Error in MCP operation: %s", e, exc_info=True)
+            effective_timeout: Final = (
+                min(request.timeout if request.timeout is not None else MCP_CLIENT_TIMEOUT, timeout_seconds)
+                if any(
+                    isinstance(cause, McpError) and as_mcp_read_timeout(cause) is not None
+                    for cause in iter_exception_tree(e)
+                )
+                else timeout_seconds
+            )
             return {
                 "status": "error",
                 "error": True,
-                "message": _connection_error_message(e, request.url, timeout_seconds),
+                "message": _connection_error_message(e, request.url, effective_timeout),
             }
 
     async def _preview_openapi_tools(spec_path: str) -> dict:
diff --git a/litellm/proxy/_experimental/mcp_server/server.py b/litellm/proxy/_experimental/mcp_server/server.py
index 44c00df996c..95129d9aeed 100644
--- a/litellm/proxy/_experimental/mcp_server/server.py
+++ b/litellm/proxy/_experimental/mcp_server/server.py
@@ -49,7 +49,11 @@ from litellm.proxy._experimental.mcp_server.mcp_context import (
     _mcp_gateway_server_name,
     _mcp_proxy_mode,  # pyright: ignore[reportPrivateUsage]  # server-owned request mode
 )
-from litellm.proxy._experimental.mcp_server.mcp_debug import MCPDebug
+from litellm.proxy._experimental.mcp_server.mcp_debug import (
+    MCP_AUTH_DIAGNOSTICS_SCOPE_KEY,
+    MCPAuthDiagnostics,
+    MCPDebug,
+)
 from litellm.proxy._experimental.mcp_server.oauth_utils import (
     _redact_mcp_resource_url,
     get_passthrough_www_authenticate,
@@ -767,12 +771,12 @@ if MCP_AVAILABLE:
                     _stateful_auth_context_cleanup_task.cancel()
                     with contextlib.suppress(asyncio.CancelledError):
                         await _stateful_auth_context_cleanup_task
-                if _session_manager_cm:
-                    await _session_manager_cm.__aexit__(None, None, None)
-                if _session_manager_stateful_cm:
-                    await _session_manager_stateful_cm.__aexit__(None, None, None)
                 if _sse_session_manager_cm:
                     await _sse_session_manager_cm.__aexit__(None, None, None)
+                if _session_manager_stateful_cm:
+                    await _session_manager_stateful_cm.__aexit__(None, None, None)
+                if _session_manager_cm:
+                    await _session_manager_cm.__aexit__(None, None, None)
             except Exception as e:
                 verbose_logger.exception("Error during session manager shutdown: %s", e)
 
@@ -1005,6 +1009,7 @@ if MCP_AVAILABLE:
 
         if _mcp_proxy_mode.get() and name in MCP_PROXY_TOOL_NAMES:
             assert user_api_key_auth is not None
+            proxy_call_start: Final = datetime.now()  # noqa: DTZ005  # logging pipeline uses naive datetimes
             proxy_logging_obj: Final = (
                 await _build_virtual_call_logging_obj(
                     name=name,
@@ -1016,18 +1021,55 @@ if MCP_AVAILABLE:
                 if name == MCP_PROXY_CALL_TOOL_NAME
                 else None
             )
-            return await handle_mcp_proxy_tool(
-                name=name,
-                arguments=arguments or {},  # mutable-ok: proxy handler payload
-                user_api_key_dict=user_api_key_auth,
-                client_ip=client_ip,
-                mcp_servers=mcp_servers,
-                mcp_auth_header=mcp_auth_header,
-                mcp_server_auth_headers=mcp_server_auth_headers,
-                oauth2_headers=oauth2_headers,
-                raw_headers=raw_headers,
-                litellm_logging_obj=proxy_logging_obj,
-            )
+            try:
+                proxy_result: Final = await handle_mcp_proxy_tool(
+                    name=name,
+                    arguments=arguments or {},  # mutable-ok: proxy handler payload
+                    user_api_key_dict=user_api_key_auth,
+                    client_ip=client_ip,
+                    mcp_servers=mcp_servers,
+                    mcp_auth_header=mcp_auth_header,
+                    mcp_server_auth_headers=mcp_server_auth_headers,
+                    oauth2_headers=oauth2_headers,
+                    raw_headers=raw_headers,
+                    litellm_logging_obj=proxy_logging_obj,
+                )
+            except Exception as exc:
+                if proxy_logging_obj is not None:
+                    from litellm.proxy.proxy_server import proxy_logging_obj as request_logging_obj
+
+                    failure_end: Final = datetime.now()  # noqa: DTZ005  # matches the logging pipeline start time
+                    failure_traceback: Final = traceback.format_exc(limit=MAXIMUM_TRACEBACK_LINES_TO_LOG)
+                    try:
+                        proxy_logging_obj.failure_handler(exc, failure_traceback, proxy_call_start, failure_end)
+                        await proxy_logging_obj.async_failure_handler(
+                            exc, failure_traceback, proxy_call_start, failure_end
+                        )
+                        if not isinstance(exc, MCPUpstreamAuthError):
+                            await request_logging_obj.post_call_failure_hook(
+                                request_data={  # mutable-ok: failure hook mutates its request payload
+                                    "name": name,
+                                    "arguments": arguments,
+                                    "litellm_logging_obj": proxy_logging_obj,
+                                },
+                                original_exception=exc,
+                                user_api_key_dict=user_api_key_auth,
+                                route="/mcp/call_tool",
+                                traceback_str=failure_traceback,
+                            )
+                    except Exception:  # noqa: BLE001  # a failing failure hook must not mask the tool call's own error
+                        verbose_logger.exception("Error logging failed MCP proxy tool call")
+                raise
+            if proxy_logging_obj is not None:
+                return await _fire_mcp_tool_call_logging(
+                    logging_obj=proxy_logging_obj,
+                    result=proxy_result,
+                    start_time=proxy_call_start,
+                    end_time=datetime.now(),  # noqa: DTZ005  # matches the logging pipeline start time
+                    user_api_key_auth=user_api_key_auth,
+                    request_data=types.MappingProxyType({"name": name, "arguments": arguments}),
+                )
+            return proxy_result
 
         if name not in VIRTUAL_TOOL_NAMES:
             return None
@@ -2006,18 +2048,44 @@ if MCP_AVAILABLE:
             return texts[0][1]
         return "\n\n---\n\n".join(f"[{lbl}]\n{txt}" for lbl, txt in texts)
 
+    async def _raise_if_initialize_grants_no_mcp_servers(
+        allowed: Sequence[MCPServer],
+        user_api_key_auth: UserAPIKeyAuth | None,
+        mcp_servers: Sequence[str] | None,
+        client_ip: str | None,
+    ) -> None:
+        if allowed or user_api_key_auth is None or not user_api_key_auth.api_key:
+            return
+        if mcp_servers:
+            await raise_denied_scoped_mcp_access(
+                requested_names=mcp_servers,
+                user_api_key_auth=user_api_key_auth,
+                client_ip=client_ip,
+            )
+        no_servers_denial: Final[_McpDeniedDetail] = {
+            "error": (
+                "The key has no MCP servers granted, or none of its granted servers is loaded and allowed for "
+                "this client IP. Grant servers or access groups to the key, its team, or its organization "
+                "(object_permission.mcp_servers), check the server's allowed IPs, and reconnect."
+            )
+        }
+        raise HTTPException(status_code=403, detail=no_servers_denial)
+
     @contextlib.asynccontextmanager
     async def _gateway_initialize_instructions_request_scope(
         user_api_key_auth: UserAPIKeyAuth | None,
         mcp_servers: list[str] | None,
         client_ip: str | None,
         scoped_server_endpoint: bool = False,
+        is_initialize: bool = False,
     ) -> AsyncIterator[None]:
         allowed: Final = await _get_allowed_mcp_servers(
             user_api_key_auth=user_api_key_auth,
             mcp_servers=mcp_servers,
             client_ip=client_ip,
         )
+        if is_initialize:
+            await _raise_if_initialize_grants_no_mcp_servers(allowed, user_api_key_auth, mcp_servers, client_ip)
         if allowed:
             # return_exceptions=True: a per-server probe failure (incl. CancelledError
             # bubbled from anyio task group teardown on connection refused) must not
@@ -3493,7 +3561,9 @@ if MCP_AVAILABLE:
         server_name: str | None,
         session_id: str | None = None,
     ) -> StandardLoggingMCPToolCall:
-        mcp_server: Final = global_mcp_server_manager._get_mcp_server_from_tool_name(name)
+        mcp_server: Final = global_mcp_server_manager._get_mcp_server_from_tool_name(
+            add_server_prefix_to_name(name, server_name) if server_name else name
+        )
         namespaced_tool_name: Final = f"{server_name}/{name}" if server_name else name
         if mcp_server:
             mcp_info: Final = mcp_server.mcp_info or {}
@@ -4432,13 +4502,15 @@ if MCP_AVAILABLE:
                 raw_headers=raw_headers,
                 scope=dict(scope),
                 mcp_servers=mcp_servers,
-                mcp_auth_header=mcp_auth_header,
-                mcp_server_auth_headers=mcp_server_auth_headers,
                 oauth2_headers=oauth2_headers,
                 client_ip=_client_ip,
             )
-            if _debug_headers:
-                send = MCPDebug.wrap_send_with_debug_headers(send, _debug_headers)
+            diagnostics: Final = MCPAuthDiagnostics() if _debug_headers else None
+            if diagnostics is not None:
+                scope[MCP_AUTH_DIAGNOSTICS_SCOPE_KEY] = diagnostics
+                send = MCPDebug.wrap_send_with_debug_headers(
+                    send, _debug_headers, diagnostics.headers, request_method=scope.get("method")
+                )
 
             # Ensure session managers are initialized
             if not _SESSION_MANAGERS_INITIALIZED:
@@ -4637,6 +4709,7 @@ if MCP_AVAILABLE:
                     mcp_servers,
                     _client_ip,
                     scoped_server_endpoint=scoped_server_endpoint,
+                    is_initialize=is_initialize,
                 ):
                     await target_manager.handle_request(scope, receive, local_send)
                     if use_stateful and session_id and scope.get("method") == "DELETE":
@@ -4773,6 +4846,7 @@ if MCP_AVAILABLE:
                 mcp_servers,
                 _sse_client_ip,
                 scoped_server_endpoint=scoped_server_endpoint,
+                is_initialize=scope.get("method") == "GET",
             ):
                 await sse_session_manager.handle_request(scope, receive, send)
         except MCPUpstreamAuthError as e:
diff --git a/litellm/proxy/_experimental/mcp_server/toolset_db.py b/litellm/proxy/_experimental/mcp_server/toolset_db.py
index ecaaf35e817..48bad178927 100644
--- a/litellm/proxy/_experimental/mcp_server/toolset_db.py
+++ b/litellm/proxy/_experimental/mcp_server/toolset_db.py
@@ -132,10 +132,18 @@ async def update_mcp_toolset(
     data: UpdateMCPToolsetRequest,
     touched_by: str,
 ) -> MCPToolset | None:
-    data_dict: Final = data.model_dump(exclude_none=True, exclude={"toolset_id"})
-    if "tools" in data_dict:
-        data_dict["tools"] = json.dumps(data_dict["tools"])
-    data_dict["updated_by"] = touched_by
+    """A partial update: absent keeps, null clears. A toolset always has a name and a
+    tool list, so a null ``toolset_name`` or ``tools`` is a no-op rather than a clear;
+    emptying the tool selection is an explicit ``[]``, which cannot be mistaken for a
+    caller that left the field out."""
+    data_dict: Final = dict(  # mutable-ok: Prisma requires a plain dict for JSON query serialization
+        (
+            (field, json.dumps(value) if field == "tools" else value)
+            for field, value in data.model_dump(exclude_unset=True).items()
+            if field != "toolset_id" and (field not in ("toolset_name", "tools") or value is not None)
+        ),
+        updated_by=touched_by,
+    )
     try:
         row: Final = await _toolset_table(prisma_client).update(
             where={"toolset_id": data.toolset_id},
diff --git a/litellm/proxy/_lazy_openapi_snapshot.json b/litellm/proxy/_lazy_openapi_snapshot.json
index 4d5cdcc8003..f0af17ab818 100644
--- a/litellm/proxy/_lazy_openapi_snapshot.json
+++ b/litellm/proxy/_lazy_openapi_snapshot.json
@@ -5384,7 +5384,7 @@
               "additionalProperties": {
                 "type": "string"
               },
-              "description": "Git source reference",
+              "description": "Plugin source reference",
               "title": "Source",
               "type": "object"
             },
@@ -5411,7 +5411,7 @@
           "type": "object"
         },
         "RegisterPluginRequest": {
-          "description": "Request body for registering a plugin in the marketplace.\n\nLiteLLM acts as a registry/discovery layer. Plugins are hosted on\nGitHub/GitLab/Bitbucket and referenced by their git source.",
+          "description": "Request body for registering a plugin in the marketplace.\n\nLiteLLM acts as a registry/discovery layer. Plugins are hosted on\nGitHub/GitLab/Bitbucket or as a zip archive on any https host and referenced by their source.",
           "properties": {
             "author": {
               "anyOf": [
@@ -5509,7 +5509,7 @@
               "additionalProperties": {
                 "type": "string"
               },
-              "description": "Git source reference. Supported formats:\n- GitHub: {'source': 'github', 'repo': 'org/repo'}\n- Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}\n- Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}",
+              "description": "Plugin source reference. Supported formats:\n- GitHub: {'source': 'github', 'repo': 'org/repo'}\n- Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}\n- Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}\n- Zip archive on any https host (e.g. S3): {'source': 'archive', 'url': 'https://bucket.s3.amazonaws.com/plugin.zip', 'sha256': '<optional hex digest>'}",
               "title": "Source",
               "type": "object"
             },
@@ -5653,7 +5653,7 @@
               "additionalProperties": {
                 "type": "string"
               },
-              "description": "Git source reference. Supported formats:\n- GitHub: {'source': 'github', 'repo': 'org/repo'}\n- Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}\n- Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}",
+              "description": "Plugin source reference. Supported formats:\n- GitHub: {'source': 'github', 'repo': 'org/repo'}\n- Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}\n- Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}\n- Zip archive on any https host (e.g. S3): {'source': 'archive', 'url': 'https://bucket.s3.amazonaws.com/plugin.zip', 'sha256': '<optional hex digest>'}",
               "title": "Source",
               "type": "object"
             },
@@ -5721,8 +5721,26 @@
     "paths": {
       "/claude-code/marketplace.json": {
         "get": {
-          "description": "Serve marketplace.json for Claude Code plugin discovery.\n\nThis endpoint is accessed by Claude Code CLI when users run:\n- claude plugin marketplace add <url>\n- claude plugin install <name>@<marketplace>\n\nReturns:\n    Marketplace catalog with list of available plugins and their git sources.\n\nExample:\n    ```bash\n    claude plugin marketplace add http://localhost:4000/claude-code/marketplace.json\n    claude plugin install my-plugin@litellm\n    ```",
+          "description": "Serve marketplace.json for Claude Code plugin discovery.\n\nThis endpoint is accessed by Claude Code CLI when users run:\n- claude plugin marketplace add <url>\n- claude plugin install <name>@<marketplace>\n\nWithout `key` the catalog holds the enabled (public) plugins. With `?key=sk-...`\nthe key is authenticated and the catalog also holds the disabled plugins granted\nto it through `object_permission.skills` on the key or its team.\n\nReturns:\n    Marketplace catalog with list of available plugins and their git sources.\n\nExample:\n    ```bash\n    claude plugin marketplace add http://localhost:4000/claude-code/marketplace.json\n    claude plugin marketplace add \"http://localhost:4000/claude-code/marketplace.json?key=sk-...\"\n    claude plugin install my-plugin@litellm\n    ```",
           "operationId": "get_marketplace_claude_code_marketplace_json_get",
+          "parameters": [
+            {
+              "in": "query",
+              "name": "key",
+              "required": false,
+              "schema": {
+                "anyOf": [
+                  {
+                    "type": "string"
+                  },
+                  {
+                    "type": "null"
+                  }
+                ],
+                "title": "Key"
+              }
+            }
+          ],
           "responses": {
             "200": {
               "content": {
@@ -5731,6 +5749,16 @@
                 }
               },
               "description": "Successful Response"
+            },
+            "422": {
+              "content": {
+                "application/json": {
+                  "schema": {
+                    "$ref": "#/components/schemas/HTTPValidationError"
+                  }
+                }
+              },
+              "description": "Validation Error"
             }
           },
           "summary": "Get Marketplace",
@@ -5788,7 +5816,7 @@
           ]
         },
         "post": {
-          "description": "Register a new plugin in the LiteLLM marketplace.\n\nLiteLLM acts as a registry/discovery layer. Plugins are hosted on\nGitHub/GitLab/Bitbucket. Claude Code will clone from the git source\nwhen users install.\n\nThis endpoint is create-only and never overwrites. If a plugin with\nthe same name already exists it returns 409 Conflict; use\nPUT /claude-code/plugins/{plugin_name} to update an existing plugin.\n\nRequires a proxy admin API key.\n\nParameters:\n    - name: Plugin name (kebab-case)\n    - source: Git source reference (github, url, or git-subdir format)\n    - version: Semantic version (optional)\n    - description: Plugin description (optional)\n    - author: Author information (optional)\n    - homepage: Plugin homepage URL (optional)\n    - keywords: Search keywords (optional)\n    - category: Plugin category (optional)\n\nReturns:\n    Registration status (action is always \"created\") and plugin information.\n\nExample:\n    ```bash\n    curl -X POST http://localhost:4000/claude-code/plugins \\\n      -H \"Authorization: Bearer sk-...\" \\\n      -H \"Content-Type: application/json\" \\\n      -d '{\n        \"name\": \"my-plugin\",\n        \"source\": {\"source\": \"github\", \"repo\": \"org/my-plugin\"},\n        \"version\": \"1.0.0\",\n        \"description\": \"My awesome plugin\"\n      }'\n    ```",
+          "description": "Register a new plugin in the LiteLLM marketplace.\n\nLiteLLM acts as a registry/discovery layer. Plugins are hosted on\nGitHub/GitLab/Bitbucket or as a zip archive on any https host (e.g. S3).\nClaude Code clones the git source or downloads the archive when users install.\n\nThis endpoint is create-only and never overwrites. If a plugin with\nthe same name already exists it returns 409 Conflict; use\nPUT /claude-code/plugins/{plugin_name} to update an existing plugin.\n\nRequires a proxy admin API key.\n\nParameters:\n    - name: Plugin name (kebab-case)\n    - source: Plugin source reference (github, url, git-subdir, or archive format)\n    - version: Semantic version (optional)\n    - description: Plugin description (optional)\n    - author: Author information (optional)\n    - homepage: Plugin homepage URL (optional)\n    - keywords: Search keywords (optional)\n    - category: Plugin category (optional)\n\nReturns:\n    Registration status (action is always \"created\") and plugin information.\n\nExample:\n    ```bash\n    curl -X POST http://localhost:4000/claude-code/plugins \\\n      -H \"Authorization: Bearer sk-...\" \\\n      -H \"Content-Type: application/json\" \\\n      -d '{\n        \"name\": \"my-plugin\",\n        \"source\": {\"source\": \"github\", \"repo\": \"org/my-plugin\"},\n        \"version\": \"1.0.0\",\n        \"description\": \"My awesome plugin\"\n      }'\n    ```",
           "operationId": "register_plugin_claude_code_plugins_post",
           "requestBody": {
             "content": {
@@ -5923,7 +5951,7 @@
           ]
         },
         "put": {
-          "description": "Update an existing plugin in the LiteLLM marketplace.\n\nThe plugin is identified by its name in the path, which is the resource\nidentity and cannot be changed here. This is a full replace, not a merge:\nthe manifest is rebuilt from the request body, so any optional field left\nout is reset to its default (e.g. an omitted version is cleared, not kept).\nSend the full desired state.\n\nReturns 404 if no plugin with the given name exists; use\nPOST /claude-code/plugins to create a new plugin.\n\nRequires a proxy admin API key.\n\nParameters:\n    - plugin_name: Name of the plugin to update (path parameter)\n    - source: Git source reference (github, url, or git-subdir format)\n    - version: Semantic version (optional)\n    - description: Plugin description (optional)\n    - author: Author information (optional)\n    - homepage: Plugin homepage URL (optional)\n    - keywords: Search keywords (optional)\n    - category: Plugin category (optional)\n\nReturns:\n    Update status (action is always \"updated\") and plugin information.\n\nExample:\n    ```bash\n    curl -X PUT http://localhost:4000/claude-code/plugins/my-plugin \\\n      -H \"Authorization: Bearer sk-...\" \\\n      -H \"Content-Type: application/json\" \\\n      -d '{\n        \"source\": {\"source\": \"github\", \"repo\": \"org/my-plugin\"},\n        \"version\": \"2.0.0\",\n        \"description\": \"My awesome plugin\"\n      }'\n    ```",
+          "description": "Update an existing plugin in the LiteLLM marketplace.\n\nThe plugin is identified by its name in the path, which is the resource\nidentity and cannot be changed here. This is a full replace, not a merge:\nthe manifest is rebuilt from the request body, so any optional field left\nout is reset to its default (e.g. an omitted version is cleared, not kept).\nSend the full desired state.\n\nReturns 404 if no plugin with the given name exists; use\nPOST /claude-code/plugins to create a new plugin.\n\nRequires a proxy admin API key.\n\nParameters:\n    - plugin_name: Name of the plugin to update (path parameter)\n    - source: Plugin source reference (github, url, git-subdir, or archive format)\n    - version: Semantic version (optional)\n    - description: Plugin description (optional)\n    - author: Author information (optional)\n    - homepage: Plugin homepage URL (optional)\n    - keywords: Search keywords (optional)\n    - category: Plugin category (optional)\n\nReturns:\n    Update status (action is always \"updated\") and plugin information.\n\nExample:\n    ```bash\n    curl -X PUT http://localhost:4000/claude-code/plugins/my-plugin \\\n      -H \"Authorization: Bearer sk-...\" \\\n      -H \"Content-Type: application/json\" \\\n      -d '{\n        \"source\": {\"source\": \"github\", \"repo\": \"org/my-plugin\"},\n        \"version\": \"2.0.0\",\n        \"description\": \"My awesome plugin\"\n      }'\n    ```",
           "operationId": "update_plugin_claude_code_plugins__plugin_name__put",
           "parameters": [
             {
diff --git a/litellm/proxy/_types.py b/litellm/proxy/_types.py
index d746cfd38d8..2cbff128635 100644
--- a/litellm/proxy/_types.py
+++ b/litellm/proxy/_types.py
@@ -3,6 +3,7 @@ import json
 import os
 from collections.abc import Callable, Mapping
 from datetime import datetime
+from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Literal, NamedTuple
 
 import httpx
@@ -496,6 +497,9 @@ class LiteLLMRoutes(enum.Enum):
         "/v1/messages/count_tokens",
         "/v1/skills",
         "/v1/skills/{skill_id}",
+        "/claude-code/marketplace.json",
+        "/claude-code/plugins",
+        "/claude-code/plugins/{plugin_name}",
     ]
 
     # MCP tool-call / passthrough routes — data-plane. Gated by DISABLE_LLM_API_ENDPOINTS.
@@ -699,6 +703,7 @@ class LiteLLMRoutes(enum.Enum):
         "/spend/logs",
         "/spend/logs/v2",
         "/spend/logs/ui",
+        "/spend/logs/ui/{request_id}",
         "/spend/logs/session/ui",
         "/key/spend/report",
         "/user/spend/report",
@@ -928,10 +933,10 @@ class LiteLLMRoutes(enum.Enum):
             # PROXY_ADMIN_VIEW_ONLY — the route gate must match).
             "/customer/list",
             "/customer/info",
-            # UI Logs page detail drawer (single + session) and the filter facets.
-            # The list endpoint `/spend/logs/ui` is covered via
-            # spend_tracking_routes below.
-            "/spend/logs/ui/{logId}",
+            # UI Logs page session detail drawer and the end-user filter facet.
+            # The list endpoint `/spend/logs/ui` and the single-log detail route
+            # `/spend/logs/ui/{request_id}` are covered via spend_tracking_routes
+            # below.
             "/spend/logs/session/ui",
             "/management/v1/spend_logs/end_users",
             "/management/v1/spend_logs/users",
@@ -1123,6 +1128,7 @@ class LiteLLM_ObjectPermissionBase(LiteLLMPydanticObjectBase):
     models: list[str] | None = None
     search_tools: list[str] | None = None
     mcp_tool_search_enabled: bool | None = None
+    skills: list[str] | None = None
 
 
 from litellm.models.team import BudgetLimitEntry as BudgetLimitEntry  # noqa: E402
@@ -1294,6 +1300,13 @@ class UpdateKeyRequest(KeyRequestBase):
     rotation_interval: str | None = None
     organization_id: str | None = None
 
+    @model_validator(mode="before")
+    @classmethod
+    def drop_blank_team_id(cls, values: object) -> object:
+        if isinstance(values, Mapping) and values.get("team_id") == "":
+            return MappingProxyType({k: v for k, v in values.items() if k != "team_id"})
+        return values
+
     @field_validator("organization_id", mode="before")
     @classmethod
     def treat_cleared_organization_id_as_unset(cls, v: object) -> object:
@@ -2419,6 +2432,13 @@ class CoordinationRedisParams(LiteLLMPydanticObjectBase):
     )
     sentinel_password: str | None = Field(None, description="password for the sentinel nodes")
     service_name: str | None = Field(None, description="sentinel service name")
+    aws_iam_auth: bool | str | None = Field(None, description="enable AWS ElastiCache IAM authentication")
+    aws_iam_user_name: str | None = Field(None, description="AWS ElastiCache IAM user name")
+    aws_iam_cache_name: str | None = Field(None, description="AWS ElastiCache cache name")
+    aws_iam_region: str | None = Field(None, description="AWS region for ElastiCache IAM authentication")
+    aws_iam_serverless: bool | str | None = Field(
+        None, description="the ElastiCache cache is serverless rather than a self-designed cluster"
+    )
 
     def has_connection_target(self) -> bool:
         return any(value is not None for value in (self.host, self.url, self.startup_nodes, self.sentinel_nodes))
@@ -2828,6 +2848,18 @@ class ConfigGeneralSettings(LiteLLMPydanticObjectBase):
             "UI username/password login. Default is False."
         ),
     )
+    disable_env_credential_login: bool | None = Field(
+        None,
+        description=(
+            "If True, disables signing in to the Admin UI with the environment credentials: "
+            "UI_USERNAME/UI_PASSWORD, or the master key when UI_PASSWORD is unset (that fallback "
+            "means env-credential login is always live by default). Database users with passwords "
+            "are unaffected. LOCKOUT RISK: create at least one proxy admin user with a password "
+            "before enabling, or nobody can sign in to the UI. A locked-out admin can still "
+            "administer the proxy over the API with the master key, and can unset this setting "
+            "and restart the proxy to restore env-credential login. Default is False."
+        ),
+    )
     disable_budget_reservation: bool | None = Field(
         None,
         description=(
@@ -3706,6 +3738,15 @@ class AllCallbacks(LiteLLMPydanticObjectBase):
         ],
     )
 
+    pointfive: CallbackOnUI = CallbackOnUI(
+        litellm_callback_name="pointfive",
+        ui_callback_name="PointFive",
+        litellm_callback_params=[  # mutable-ok: the registry field is typed list
+            "POINTFIVE_API_KEY",
+            "POINTFIVE_API_URL",
+        ],
+    )
+
 
 class SpendLogsRouterMetadata(TypedDict):
     """
@@ -5148,9 +5189,26 @@ class CostEstimateRequest(LiteLLMPydanticObjectBase):
     model: str = Field(description="Model name (from /model_group/info)")
     input_tokens: int = Field(description="Expected input tokens per request", ge=0)
     output_tokens: int = Field(description="Expected output tokens per request", ge=0)
+    cache_read_input_tokens: int = Field(
+        default=0, description="Input tokens read from the prompt cache; counted within input_tokens", ge=0
+    )
+    cache_creation_input_tokens: int = Field(
+        default=0, description="Input tokens written to the prompt cache; counted within input_tokens", ge=0
+    )
+    reasoning_tokens: int = Field(
+        default=0, description="Reasoning tokens the model emits; counted within output_tokens", ge=0
+    )
     num_requests_per_day: int | None = Field(default=None, description="Number of requests per day", ge=0)
     num_requests_per_month: int | None = Field(default=None, description="Number of requests per month", ge=0)
 
+    @model_validator(mode="after")
+    def validate_token_subsets(self) -> "CostEstimateRequest":
+        if self.cache_read_input_tokens + self.cache_creation_input_tokens > self.input_tokens:
+            raise ValueError("cache_read_input_tokens plus cache_creation_input_tokens cannot exceed input_tokens")
+        if self.reasoning_tokens > self.output_tokens:
+            raise ValueError("reasoning_tokens cannot exceed output_tokens")
+        return self
+
 
 class CostEstimateResponse(LiteLLMPydanticObjectBase):
     """Response body for /cost/estimate endpoint."""
@@ -5158,6 +5216,9 @@ class CostEstimateResponse(LiteLLMPydanticObjectBase):
     model: str
     input_tokens: int
     output_tokens: int
+    cache_read_input_tokens: int = 0
+    cache_creation_input_tokens: int = 0
+    reasoning_tokens: int = 0
     num_requests_per_day: int | None = None
     num_requests_per_month: int | None = None
     # Per-request costs
@@ -5165,17 +5226,33 @@ class CostEstimateResponse(LiteLLMPydanticObjectBase):
     input_cost_per_request: float = Field(description="Input token cost per request (before margin)")
     output_cost_per_request: float = Field(description="Output token cost per request (before margin)")
     margin_cost_per_request: float = Field(default=0.0, description="Margin/fee added per request")
+    cache_read_cost_per_request: float = Field(default=0.0, description="Cache-read share of input_cost_per_request")
+    cache_creation_cost_per_request: float = Field(
+        default=0.0, description="Cache-write share of input_cost_per_request"
+    )
+    reasoning_cost_per_request: float = Field(default=0.0, description="Reasoning share of output_cost_per_request")
     # Daily costs (if num_requests_per_day provided)
     daily_cost: float | None = Field(default=None, description="Total daily cost (includes margin)")
     daily_input_cost: float | None = Field(default=None, description="Daily input token cost")
     daily_output_cost: float | None = Field(default=None, description="Daily output token cost")
     daily_margin_cost: float | None = Field(default=None, description="Daily margin/fee")
+    daily_cache_read_cost: float | None = Field(default=None, description="Cache-read share of daily_input_cost")
+    daily_cache_creation_cost: float | None = Field(default=None, description="Cache-write share of daily_input_cost")
+    daily_reasoning_cost: float | None = Field(default=None, description="Reasoning share of daily_output_cost")
     # Monthly costs (if num_requests_per_month provided)
     monthly_cost: float | None = Field(default=None, description="Total monthly cost (includes margin)")
     monthly_input_cost: float | None = Field(default=None, description="Monthly input token cost")
     monthly_output_cost: float | None = Field(default=None, description="Monthly output token cost")
     monthly_margin_cost: float | None = Field(default=None, description="Monthly margin/fee")
-    # Pricing info
-    input_cost_per_token: float | None = None
-    output_cost_per_token: float | None = None
+    monthly_cache_read_cost: float | None = Field(default=None, description="Cache-read share of monthly_input_cost")
+    monthly_cache_creation_cost: float | None = Field(
+        default=None, description="Cache-write share of monthly_input_cost"
+    )
+    monthly_reasoning_cost: float | None = Field(default=None, description="Reasoning share of monthly_output_cost")
+    # Pricing info: the rates this request's usage bills at, after token tiers and regional multipliers
+    input_cost_per_token: float | None = Field(default=None, description="Rate billed per input token")
+    output_cost_per_token: float | None = Field(default=None, description="Rate billed per output token")
+    cache_read_input_token_cost: float | None = Field(default=None, description="Rate billed per cache-read token")
+    cache_creation_input_token_cost: float | None = Field(default=None, description="Rate billed per cache-write token")
+    output_cost_per_reasoning_token: float | None = Field(default=None, description="Rate billed per reasoning token")
     provider: str | None = None
diff --git a/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_marketplace.py b/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_marketplace.py
index 65bc46edfaf..7c6a4571948 100644
--- a/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_marketplace.py
+++ b/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_marketplace.py
@@ -2,14 +2,15 @@
 CLAUDE CODE MARKETPLACE
 
 Provides a registry/discovery layer for Claude Code plugins.
-Plugins are stored as metadata + git source references in LiteLLM database.
-Actual plugin files are hosted on GitHub/GitLab/Bitbucket.
+Plugins are stored as metadata + source references in LiteLLM database.
+Actual plugin files are hosted on GitHub/GitLab/Bitbucket or as a zip archive on
+any HTTPS host (S3, Artifactory, a static file server).
 
 Endpoints:
-/claude-code/marketplace.json  - GET  - List plugins for Claude Code discovery (unauthenticated)
+/claude-code/marketplace.json  - GET  - List plugins for Claude Code discovery (unauthenticated; `?key=` adds the key's granted skills)
 /claude-code/plugins           - POST - Register a new plugin (create-only, proxy admin only)
-/claude-code/plugins           - GET  - List plugins (any authenticated key)
-/claude-code/plugins/{name}    - GET  - Get plugin details (any authenticated key)
+/claude-code/plugins           - GET  - List plugins visible to the key (enabled, plus granted disabled ones)
+/claude-code/plugins/{name}    - GET  - Get plugin details (403 on a disabled plugin the key is not granted)
 /claude-code/plugins/{name}    - PUT  - Update an existing plugin (proxy admin only)
 /claude-code/plugins/{name}/enable  - POST - Enable a plugin (proxy admin only)
 /claude-code/plugins/{name}/disable - POST - Disable a plugin (proxy admin only)
@@ -21,12 +22,17 @@ import re
 from collections.abc import Mapping, Sequence
 from datetime import datetime, timezone
 from typing import Annotated, Final, Protocol, TypedDict
+from urllib.parse import urlsplit
 
-from fastapi import APIRouter, Depends, HTTPException
+from fastapi import APIRouter, Depends, HTTPException, Request
 from fastapi.responses import JSONResponse
 
 from litellm._logging import verbose_proxy_logger
-from litellm.proxy._types import CommonProxyErrors, UserAPIKeyAuth
+from litellm.proxy._types import CommonProxyErrors, ProxyException, UserAPIKeyAuth
+from litellm.proxy.anthropic_endpoints.claude_code_endpoints.claude_code_skill_access import (
+    SkillVisibility,
+    skill_visibility,
+)
 from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
 from litellm.proxy.common_utils.resource_ownership import is_proxy_admin
 from litellm.repositories.table_repositories import ClaudeCodePluginRepository
@@ -82,7 +88,7 @@ async def _get_prisma_client() -> object:
     "/claude-code/marketplace.json",
     tags=["Claude Code Marketplace"],
 )
-async def get_marketplace():
+async def get_marketplace(request: Request, key: str | None = None):
     """
     Serve marketplace.json for Claude Code plugin discovery.
 
@@ -90,24 +96,35 @@ async def get_marketplace():
     - claude plugin marketplace add <url>
     - claude plugin install <name>@<marketplace>
 
+    Without `key` the catalog holds the enabled (public) plugins. With `?key=sk-...`
+    the key is authenticated and the catalog also holds the disabled plugins granted
+    to it through `object_permission.skills` on the key or its team.
+
     Returns:
         Marketplace catalog with list of available plugins and their git sources.
 
     Example:
         ```bash
         claude plugin marketplace add http://localhost:4000/claude-code/marketplace.json
+        claude plugin marketplace add "http://localhost:4000/claude-code/marketplace.json?key=sk-..."
         claude plugin install my-plugin@litellm
         ```
     """
     try:
         prisma_client: Final = await _get_prisma_client()
 
+        caller: Final[UserAPIKeyAuth | None] = (
+            await user_api_key_auth(request=request, api_key=f"Bearer {key}") if key else None
+        )
+        visibility: Final[SkillVisibility] = skill_visibility(caller)
         plugins: Final[Sequence[_PluginRecord]] = await ClaudeCodePluginRepository(prisma_client).table.find_many(
-            where={"enabled": True}
+            where=visibility.where()
         )
 
         plugin_list: Final = []
         for plugin in plugins:
+            if not visibility.allows(plugin):
+                continue
             try:
                 manifest: Mapping[str, object] = json.loads(plugin.manifest_json or "{}")
             except json.JSONDecodeError:
@@ -147,7 +164,7 @@ async def get_marketplace():
 
         return JSONResponse(content=marketplace)
 
-    except HTTPException:
+    except (HTTPException, ProxyException):
         raise
     except Exception as e:
         verbose_proxy_logger.exception("Error generating marketplace: %s", e)
@@ -162,6 +179,15 @@ async def get_marketplace():
 # alphanumeric characters, dots, hyphens, and underscores.
 # This implicitly blocks '..', leading '/', backslashes, and percent-encoded sequences.
 _VALID_GIT_SUBDIR_PATH_RE: Final = re.compile(r"^[a-zA-Z0-9][a-zA-Z0-9._-]*(/[a-zA-Z0-9][a-zA-Z0-9._-]*)*$")
+_VALID_SHA256_RE: Final = re.compile(r"^[0-9a-fA-F]{64}$")
+
+
+def _is_https_url_with_host(url: str) -> bool:
+    try:
+        parts: Final = urlsplit(url)
+    except ValueError:
+        return False
+    return parts.scheme == "https" and bool(parts.hostname)
 
 
 def _validate_plugin_source(source: Mapping[str, str]) -> None:
@@ -199,10 +225,24 @@ def _validate_plugin_source(source: Mapping[str, str]) -> None:
                     "error": "git-subdir 'path' must be a relative path of the form 'segment/segment' (alphanumeric, dots, hyphens, underscores only)"
                 },
             )
+    elif source_type == "archive":
+        if not _is_https_url_with_host(source.get("url", "")):
+            raise HTTPException(
+                status_code=400,
+                detail={
+                    "error": "archive source must include an https 'url' field "
+                    "(e.g., 'https://bucket.s3.amazonaws.com/plugins/plugin-name.zip')"
+                },
+            )
+        if "sha256" in source and not _VALID_SHA256_RE.match(source["sha256"]):
+            raise HTTPException(
+                status_code=400,
+                detail={"error": "archive 'sha256' must be a 64-character hex digest"},
+            )
     else:
         raise HTTPException(
             status_code=400,
-            detail={"error": "source.source must be 'github', 'url', or 'git-subdir'"},
+            detail={"error": "source.source must be 'github', 'url', 'git-subdir', or 'archive'"},
         )
 
 
@@ -248,8 +288,8 @@ async def register_plugin(
     Register a new plugin in the LiteLLM marketplace.
 
     LiteLLM acts as a registry/discovery layer. Plugins are hosted on
-    GitHub/GitLab/Bitbucket. Claude Code will clone from the git source
-    when users install.
+    GitHub/GitLab/Bitbucket or as a zip archive on any https host (e.g. S3).
+    Claude Code clones the git source or downloads the archive when users install.
 
     This endpoint is create-only and never overwrites. If a plugin with
     the same name already exists it returns 409 Conflict; use
@@ -259,7 +299,7 @@ async def register_plugin(
 
     Parameters:
         - name: Plugin name (kebab-case)
-        - source: Git source reference (github, url, or git-subdir format)
+        - source: Plugin source reference (github, url, git-subdir, or archive format)
         - version: Semantic version (optional)
         - description: Plugin description (optional)
         - author: Author information (optional)
@@ -370,13 +410,15 @@ async def list_plugins(
     try:
         prisma_client: Final = await _get_prisma_client()
 
-        where: Final = {"enabled": True} if enabled_only else {}
+        visibility: Final[SkillVisibility] = skill_visibility(user_api_key_dict)
         plugins: Final[Sequence[_PluginRecord]] = await ClaudeCodePluginRepository(prisma_client).table.find_many(
-            where=where
+            where={"enabled": True} if enabled_only else visibility.where()
         )
 
         plugin_list: Final = []
         for p in plugins:
+            if not visibility.allows(p):
+                continue
             # Parse manifest to get additional fields
             manifest = json.loads(p.manifest_json) if p.manifest_json else {}
 
@@ -448,6 +490,12 @@ async def get_plugin(
                 detail={"error": f"Plugin '{plugin_name}' not found"},
             )
 
+        if not skill_visibility(user_api_key_dict).allows(plugin):
+            raise HTTPException(
+                status_code=403,
+                detail={"error": f"Plugin '{plugin_name}' is not granted to this key"},
+            )
+
         manifest: Final[Mapping[str, object]] = json.loads(plugin.manifest_json or "{}") if plugin.manifest_json else {}
 
         return {
@@ -503,7 +551,7 @@ async def update_plugin(
 
     Parameters:
         - plugin_name: Name of the plugin to update (path parameter)
-        - source: Git source reference (github, url, or git-subdir format)
+        - source: Plugin source reference (github, url, git-subdir, or archive format)
         - version: Semantic version (optional)
         - description: Plugin description (optional)
         - author: Author information (optional)
diff --git a/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_skill_access.py b/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_skill_access.py
new file mode 100644
index 00000000000..e1e1ee6f160
--- /dev/null
+++ b/litellm/proxy/anthropic_endpoints/claude_code_endpoints/claude_code_skill_access.py
@@ -0,0 +1,67 @@
+"""
+Claude Code marketplace visibility: enabled plugins are public, disabled plugins
+are private and resolve only for proxy admins or keys granted them via
+``object_permission.skills``.
+"""
+
+from dataclasses import dataclass
+from typing import TYPE_CHECKING, Final, Protocol
+
+from litellm.proxy._types import LiteLLM_ObjectPermissionTable, UserAPIKeyAuth
+from litellm.proxy.common_utils.resource_ownership import is_proxy_admin
+
+if TYPE_CHECKING:
+    from prisma.types import LiteLLM_ClaudeCodePluginTableWhereInput
+
+
+class _SkillRecord(Protocol):
+    name: str
+    enabled: bool
+
+
+def _skills_of(permission: LiteLLM_ObjectPermissionTable | None) -> frozenset[str]:
+    return frozenset(permission.skills or ()) if permission is not None else frozenset()
+
+
+def granted_skills(user_api_key_dict: UserAPIKeyAuth) -> frozenset[str]:
+    """Key grant intersected with the team grant when both are non-empty; either alone applies as is.
+
+    An empty list is the Prisma column default for every object-permission row, so it means
+    "no private grants configured here" and defers to the other scope, same as the agents check.
+    """
+    key_skills: Final = _skills_of(user_api_key_dict.object_permission)
+    team_skills: Final = _skills_of(user_api_key_dict.team_object_permission)
+    match (bool(key_skills), bool(team_skills)):
+        case (True, True):
+            return key_skills & team_skills
+        case (True, False):
+            return key_skills
+        case _:
+            return team_skills
+
+
+@dataclass(frozen=True, slots=True)
+class SkillVisibility:
+    granted: frozenset[str]
+    sees_private: bool
+
+    def allows(self, skill: _SkillRecord) -> bool:
+        return skill.enabled or self.sees_private or skill.name in self.granted
+
+    def where(self) -> "LiteLLM_ClaudeCodePluginTableWhereInput":
+        if self.sees_private:
+            return {}
+        if not self.granted:
+            return {"enabled": True}
+        return {"OR": [{"enabled": True}, {"name": {"in": sorted(self.granted)}}]}
+
+
+PUBLIC_ONLY: Final = SkillVisibility(granted=frozenset(), sees_private=False)
+
+
+def skill_visibility(user_api_key_dict: UserAPIKeyAuth | None) -> SkillVisibility:
+    if user_api_key_dict is None:
+        return PUBLIC_ONLY
+    if is_proxy_admin(user_api_key_dict):
+        return SkillVisibility(granted=frozenset(), sees_private=True)
+    return SkillVisibility(granted=granted_skills(user_api_key_dict), sees_private=False)
diff --git a/litellm/proxy/auth/auth_checks.py b/litellm/proxy/auth/auth_checks.py
index dc693317de0..1efc9611fe6 100644
--- a/litellm/proxy/auth/auth_checks.py
+++ b/litellm/proxy/auth/auth_checks.py
@@ -94,6 +94,7 @@ from litellm.proxy.common_utils.user_api_key_cache import (
     team_membership_auth_cache_key,
     team_membership_reservation_cache_key,
 )
+from litellm.proxy.db.db_lookup_gate import db_lookup_gate
 from litellm.proxy.db.exception_handler import PrismaDBExceptionHandler
 from litellm.proxy.guardrails.tool_name_extraction import (
     TOOL_CAPABLE_CALL_TYPES,
@@ -475,6 +476,7 @@ def _is_model_cost_zero(model: str | list[str] | None, llm_router: Router | None
 
 
 _NO_MODEL_INFO: Final[Mapping[str, object]] = MappingProxyType({})
+_TEAM_GRANT_RELATIONS: Final[Mapping[str, object]] = MappingProxyType({"litellm_model_table": True})
 
 
 def _has_ptu_flat_cost(model: str, llm_router: "Router") -> bool:
@@ -2858,7 +2860,9 @@ class TeamNotFoundError(HTTPException):
 async def _get_team_db_check(
     team_id: str, prisma_client: PrismaClient, team_id_upsert: bool | None = None
 ) -> "_PrismaTeamRow | None":
-    response = await _team_table(TeamRepository(prisma_client)).find_unique(where={"team_id": team_id})
+    response = await _team_table(TeamRepository(prisma_client)).find_unique(
+        where={"team_id": team_id}, include=_TEAM_GRANT_RELATIONS
+    )
 
     if response is None and team_id_upsert:
         from litellm.proxy.management_endpoints.team_endpoints import new_team
@@ -3158,7 +3162,9 @@ async def get_team_object_by_alias(
 
     # Query database by team_alias
     try:
-        teams: Final = await _team_table(TeamRepository(prisma_client)).find_many(where={"team_alias": team_alias})
+        teams: Final = await _team_table(TeamRepository(prisma_client)).find_many(
+            where={"team_alias": team_alias}, include=_TEAM_GRANT_RELATIONS
+        )
 
         if not teams:
             raise HTTPException(
@@ -3445,36 +3451,37 @@ async def _fetch_key_object_from_db_with_reconnect(
     """
     Fetch key object from DB and retry once if a DB connection error can be healed.
     """
-    try:
-        return await prisma_client.get_data(
-            token=hashed_token,
-            table_name="combined_view",
-            parent_otel_span=parent_otel_span,
-            proxy_logging_obj=proxy_logging_obj,
-        )
-    except Exception as e:
-        if PrismaDBExceptionHandler.is_database_transport_error(e):
-            did_reconnect = False
-            if hasattr(prisma_client, "attempt_db_reconnect"):
-                auth_reconnect_timeout = getattr(prisma_client, "_db_auth_reconnect_timeout_seconds", 2.0)
-                if not isinstance(auth_reconnect_timeout, (int, float)):
-                    auth_reconnect_timeout = 2.0
-                auth_reconnect_lock_timeout = getattr(prisma_client, "_db_auth_reconnect_lock_timeout_seconds", 0.1)
-                if not isinstance(auth_reconnect_lock_timeout, (int, float)):
-                    auth_reconnect_lock_timeout = 0.1
-                did_reconnect = await prisma_client.attempt_db_reconnect(
-                    reason="auth_get_key_object_lookup_failure",
-                    timeout_seconds=auth_reconnect_timeout,
-                    lock_timeout_seconds=auth_reconnect_lock_timeout,
-                )
-            if did_reconnect:
-                return await prisma_client.get_data(
-                    token=hashed_token,
-                    table_name="combined_view",
-                    parent_otel_span=parent_otel_span,
-                    proxy_logging_obj=proxy_logging_obj,
-                )
-        raise
+    async with db_lookup_gate.current():
+        try:
+            return await prisma_client.get_data(
+                token=hashed_token,
+                table_name="combined_view",
+                parent_otel_span=parent_otel_span,
+                proxy_logging_obj=proxy_logging_obj,
+            )
+        except Exception as e:
+            if PrismaDBExceptionHandler.is_database_transport_error(e):
+                did_reconnect = False
+                if hasattr(prisma_client, "attempt_db_reconnect"):
+                    auth_reconnect_timeout = getattr(prisma_client, "_db_auth_reconnect_timeout_seconds", 2.0)
+                    if not isinstance(auth_reconnect_timeout, (int, float)):
+                        auth_reconnect_timeout = 2.0
+                    auth_reconnect_lock_timeout = getattr(prisma_client, "_db_auth_reconnect_lock_timeout_seconds", 0.1)
+                    if not isinstance(auth_reconnect_lock_timeout, (int, float)):
+                        auth_reconnect_lock_timeout = 0.1
+                    did_reconnect = await prisma_client.attempt_db_reconnect(
+                        reason="auth_get_key_object_lookup_failure",
+                        timeout_seconds=auth_reconnect_timeout,
+                        lock_timeout_seconds=auth_reconnect_lock_timeout,
+                    )
+                if did_reconnect:
+                    return await prisma_client.get_data(
+                        token=hashed_token,
+                        table_name="combined_view",
+                        parent_otel_span=parent_otel_span,
+                        proxy_logging_obj=proxy_logging_obj,
+                    )
+            raise
 
 
 def jwt_key_mapping_cache_key(jwt_claim_name: str, jwt_claim_value: str) -> str:
diff --git a/litellm/proxy/auth/auth_utils.py b/litellm/proxy/auth/auth_utils.py
index f78c4221f5a..be65c3b39ec 100644
--- a/litellm/proxy/auth/auth_utils.py
+++ b/litellm/proxy/auth/auth_utils.py
@@ -27,6 +27,7 @@ from litellm.litellm_core_utils.url_utils import (
     provider_url_destination_candidates,
     validate_url,
 )
+from litellm.llms.azure.passthrough.transformation import azure_router_model_in_endpoint
 from litellm.proxy._types import *
 from litellm.proxy.common_utils.http_parsing_utils import extract_nested_form_metadata
 from litellm.types.passthrough_endpoints.pass_through_endpoints import (
@@ -316,6 +317,7 @@ _BANNED_REQUEST_BODY_PARAMS: Final[tuple[str, ...]] = (
     "aws_profile_name",
     "aws_session_name",
     "aws_external_id",
+    "aws_session_tags",
     "vertex_credentials",
     # Azure managed-identity / federated-auth token. The Azure provider
     # transformer reads ``azure_ad_token`` (top-level or via
@@ -2003,9 +2005,20 @@ def get_model_from_request(
         bedrock_model: Final = _model_from_bedrock_route(route)
         return model if bedrock_model is None else bedrock_model
 
+    if route.lower().startswith(("/azure/", "/azure_ai/")):
+        azure_model: Final = _router_model_from_azure_route(route, llm_router)
+        return model if azure_model is None else azure_model
+
     return model
 
 
+def _router_model_from_azure_route(route: str, llm_router: Router | None) -> str | None:
+    if llm_router is None:
+        return None
+    endpoint: Final = re.sub(r"^/azure(?:_ai)?/", "", route, flags=re.IGNORECASE)
+    return azure_router_model_in_endpoint(endpoint, frozenset(llm_router.get_model_names()))
+
+
 def _model_from_bedrock_route(route: str) -> str | None:
     from litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints import (
         _extract_model_from_bedrock_endpoint,
diff --git a/litellm/proxy/auth/handle_jwt.py b/litellm/proxy/auth/handle_jwt.py
index 0795cee7409..69091ee8344 100644
--- a/litellm/proxy/auth/handle_jwt.py
+++ b/litellm/proxy/auth/handle_jwt.py
@@ -53,6 +53,7 @@ from litellm.proxy._types import (
 )
 from litellm.proxy.auth.auth_checks import can_team_access_model
 from litellm.proxy.auth.route_checks import RouteChecks
+from litellm.proxy.auth.team_grants import team_model_aliases
 from litellm.proxy.common_utils.user_api_key_cache import (
     UserApiKeyCache,
     get_management_object_ttl,
@@ -1595,7 +1596,7 @@ class JWTAuthManager:
                             model=requested_model,
                             team_object=team_object,
                             llm_router=llm_router,
-                            team_model_aliases=None,
+                            team_model_aliases=team_model_aliases(team_object),
                         )
                     ):
                         is_allowed = allowed_routes_check(
@@ -2132,7 +2133,7 @@ class JWTAuthManager:
                         model=requested_model,
                         team_object=team_object,
                         llm_router=llm_router,
-                        team_model_aliases=None,
+                        team_model_aliases=team_model_aliases(team_object),
                     )
                 except ProxyException:
                     continue
diff --git a/litellm/proxy/auth/login_utils.py b/litellm/proxy/auth/login_utils.py
index 8d4f6f81363..c0a76a4fc20 100644
--- a/litellm/proxy/auth/login_utils.py
+++ b/litellm/proxy/auth/login_utils.py
@@ -85,6 +85,29 @@ def get_ui_credentials(master_key: str | None) -> tuple[str, str]:
     return ui_username, ui_password
 
 
+def _matches_env_credentials(username: str, password: str, master_key: str | None) -> bool:
+    ui_username, ui_password = get_ui_credentials(master_key)
+    return secrets.compare_digest(username.encode("utf-8"), ui_username.encode("utf-8")) and secrets.compare_digest(
+        password.encode("utf-8"), ui_password.encode("utf-8")
+    )
+
+
+def is_env_credential_login_enabled(general_settings: Mapping[str, object]) -> bool:
+    """Whether a login with UI_USERNAME/UI_PASSWORD (or the master-key fallback) can succeed.
+
+    Two settings can turn it off: `disable_env_credential_login` unconditionally, and
+    `disable_password_login_when_sso_enabled` as a side effect, since its gate rejects
+    every username/password login before the env comparison runs. Feeds both the
+    `authenticate_user` gate and the Admin UI warning banner, so the banner never nags
+    about a login path that is already unreachable.
+    """
+    if general_settings.get("disable_env_credential_login") is True:
+        return False
+    if general_settings.get("disable_password_login_when_sso_enabled") is True and is_sso_provider_fully_configured():
+        return False
+    return True
+
+
 class LoginResult:
     """Result object containing authentication data from login."""
 
@@ -129,7 +152,8 @@ async def authenticate_user(
         master_key: Master key for the proxy (required)
         prisma_client: Prisma database client (optional)
         general_settings: Proxy general_settings, checked for
-            `disable_password_login_when_sso_enabled`
+            `disable_password_login_when_sso_enabled` and
+            `disable_env_credential_login`
 
     Returns:
         LoginResult: Object containing authentication data
@@ -170,8 +194,6 @@ async def authenticate_user(
             code=500,
         )
 
-    ui_username, ui_password = get_ui_credentials(master_key)
-
     # Check if we can find the `username` in the db. On the UI, users can enter username=their email
     _user_row: LiteLLM_UserTable | None = None
     user_role: (
@@ -197,8 +219,8 @@ async def authenticate_user(
     - Login with UI_USERNAME and UI_PASSWORD
     - Login with Invite Link `user_email` and `password` combination
     """
-    if secrets.compare_digest(username.encode("utf-8"), ui_username.encode("utf-8")) and secrets.compare_digest(
-        password.encode("utf-8"), ui_password.encode("utf-8")
+    if general_settings.get("disable_env_credential_login") is not True and _matches_env_credentials(
+        username, password, master_key
     ):
         # Non SSO -> If user is using UI_USERNAME and UI_PASSWORD they are Proxy admin
         user_role = LitellmUserRoles.PROXY_ADMIN
@@ -340,8 +362,13 @@ async def authenticate_user(
                 code=401,
             )
     else:
+        env_credentials_hint: Final = (
+            "\nCheck 'UI_USERNAME', 'UI_PASSWORD' in .env file"
+            if is_env_credential_login_enabled(general_settings)
+            else ""
+        )
         raise ProxyException(
-            message="Invalid credentials used to access UI.\nCheck 'UI_USERNAME', 'UI_PASSWORD' in .env file",
+            message=f"Invalid credentials used to access UI.{env_credentials_hint}",
             type=ProxyErrorTypes.auth_error,
             param="invalid_credentials",
             code=401,
diff --git a/litellm/proxy/auth/team_grants.py b/litellm/proxy/auth/team_grants.py
new file mode 100644
index 00000000000..1196011dcdd
--- /dev/null
+++ b/litellm/proxy/auth/team_grants.py
@@ -0,0 +1,122 @@
+"""Project a team row (plus the caller's membership in it) onto the ``team_*`` fields of ``UserAPIKeyAuth``.
+
+The virtual-key path gets these fields for free from the combined-view SQL join. Every other auth path
+starts from a ``LiteLLM_TeamTable`` object instead and has to copy them over by hand, which is how JWT
+callers kept losing grants (aliases, permissions, limits) one field at a time. Build the badge through
+``team_grants`` and the two paths cannot drift.
+"""
+
+from collections.abc import Mapping, Sequence
+from types import MappingProxyType
+from typing import Annotated, Final
+
+from pydantic import BaseModel, BeforeValidator, ConfigDict, TypeAdapter, ValidationError
+from pydantic.main import IncEx
+from typing_extensions import ReadOnly, TypedDict
+
+from litellm.proxy._types import (
+    LiteLLM_ObjectPermissionTable,
+    LiteLLM_TeamMembership,
+    LiteLLM_TeamTable,
+    Member,
+)
+
+_MODEL_ALIASES_ADAPTER: Final = TypeAdapter(dict[str, str])
+_JSON_COLUMNS: Final[Mapping[str, IncEx | bool]] = MappingProxyType(
+    {"metadata": True, "litellm_model_table": MappingProxyType({"model_aliases": True})}
+)
+
+
+def _decode_model_aliases(value: object) -> object:
+    """``LiteLLM_ModelTable.model_aliases`` is typed ``str | dict``; writers hand Prisma ``json.dumps(...)``, so take both."""
+    if not isinstance(value, str):
+        return value
+    try:
+        return _MODEL_ALIASES_ADAPTER.validate_json(value)
+    except ValidationError:
+        return None
+
+
+class TeamModelAliasTable(BaseModel):
+    model_config = ConfigDict(protected_namespaces=())
+
+    model_aliases: Annotated[Mapping[str, str] | None, BeforeValidator(_decode_model_aliases)] = None
+
+
+class _TeamJsonColumns(BaseModel):
+    """The two loosely typed columns on ``LiteLLM_TeamTable``, re-read with the shape the badge needs."""
+
+    metadata: Mapping[str, object] | None = None
+    litellm_model_table: TeamModelAliasTable | None = None
+
+
+class TeamGrants(TypedDict, total=False):
+    """Keyword arguments for ``UserAPIKeyAuth``. Empty when the caller has no team, so the model's own defaults apply."""
+
+    team_alias: ReadOnly[str | None]
+    team_tpm_limit: ReadOnly[int | None]
+    team_rpm_limit: ReadOnly[int | None]
+    team_max_budget: ReadOnly[float | None]
+    team_soft_budget: ReadOnly[float | None]
+    team_spend: ReadOnly[float | None]
+    team_models: ReadOnly[Sequence[str]]
+    team_blocked: ReadOnly[bool]
+    team_metadata: ReadOnly[Mapping[str, object] | None]
+    team_model_aliases: ReadOnly[Mapping[str, str] | None]
+    team_object_permission_id: ReadOnly[str | None]
+    team_object_permission: ReadOnly[LiteLLM_ObjectPermissionTable | None]
+    team_member: ReadOnly[Member | None]
+    team_member_spend: ReadOnly[float | None]
+    team_member_tpm_limit: ReadOnly[int | None]
+    team_member_rpm_limit: ReadOnly[int | None]
+
+
+def _json_columns(team_object: LiteLLM_TeamTable) -> _TeamJsonColumns:
+    try:
+        return _TeamJsonColumns.model_validate(team_object.model_dump(include=_JSON_COLUMNS))
+    except ValidationError:
+        return _TeamJsonColumns()
+
+
+def team_model_aliases(team_object: LiteLLM_TeamTable | None) -> Mapping[str, str] | None:
+    if team_object is None:
+        return None
+    alias_table: Final = _json_columns(team_object).litellm_model_table
+    return alias_table.model_aliases if alias_table is not None else None
+
+
+def team_grants(
+    team_object: LiteLLM_TeamTable | None,
+    team_membership: LiteLLM_TeamMembership | None,
+    user_id: str | None,
+) -> TeamGrants:
+    if team_object is None:
+        return TeamGrants()
+    json_columns: Final = _json_columns(team_object)
+    return TeamGrants(
+        team_alias=team_object.team_alias,
+        team_tpm_limit=team_object.tpm_limit,
+        team_rpm_limit=team_object.rpm_limit,
+        team_max_budget=team_object.max_budget,
+        team_soft_budget=team_object.soft_budget,
+        team_spend=team_object.spend,
+        team_models=tuple(team_object.models),
+        team_blocked=team_object.blocked,
+        team_metadata=json_columns.metadata,
+        team_model_aliases=(
+            json_columns.litellm_model_table.model_aliases if json_columns.litellm_model_table is not None else None
+        ),
+        team_object_permission_id=team_object.object_permission_id,
+        team_object_permission=team_object.object_permission,
+        team_member=next(
+            (m for m in team_object.members_with_roles if user_id is not None and m.user_id == user_id),
+            None,
+        ),
+        team_member_spend=team_membership.spend if team_membership is not None else None,
+        team_member_tpm_limit=(
+            team_membership.safe_get_team_member_tpm_limit() if team_membership is not None else None
+        ),
+        team_member_rpm_limit=(
+            team_membership.safe_get_team_member_rpm_limit() if team_membership is not None else None
+        ),
+    )
diff --git a/litellm/proxy/auth/user_api_key_auth.py b/litellm/proxy/auth/user_api_key_auth.py
index 6b000489d5a..20ab9904f46 100644
--- a/litellm/proxy/auth/user_api_key_auth.py
+++ b/litellm/proxy/auth/user_api_key_auth.py
@@ -82,6 +82,7 @@ from litellm.proxy.auth.oauth2_proxy_hook import handle_oauth2_proxy_request
 from litellm.proxy.auth.resolvers import CredentialRef, Principal
 from litellm.proxy.auth.resolvers.store import IdentityStore
 from litellm.proxy.auth.route_checks import RouteChecks
+from litellm.proxy.auth.team_grants import team_grants
 from litellm.proxy.auth.trusted_proxy_utils import get_trusted_proxy_cidrs
 from litellm.proxy.common_utils.cache_coordinator import EventDrivenCacheCoordinator
 from litellm.proxy.common_utils.http_parsing_utils import (
@@ -90,7 +91,9 @@ from litellm.proxy.common_utils.http_parsing_utils import (
     _safe_get_request_query_params,
     _safe_set_request_parsed_body,
     populate_request_with_path_params,
+    read_raw_json_body,
 )
+from litellm.proxy.common_utils.model_listing_utils import claude_code_requested_group
 from litellm.proxy.common_utils.realtime_utils import _realtime_request_body
 from litellm.proxy.common_utils.user_api_key_cache import (
     UserApiKeyCache,
@@ -182,6 +185,44 @@ def _get_model_from_request_context(
     )
 
 
+_CLAUDE_MODEL_ROUTES: Final = frozenset(
+    f"/{prefix}{endpoint}" for prefix in ("", "v1/") for endpoint in ("messages", "chat/completions", "responses")
+)
+_CLAUDE_MODEL_NORMALIZED: Final = "litellm.claude_model_normalized"
+
+
+async def _normalize_claude_model(
+    request_data: dict, valid_token: UserAPIKeyAuth, request: Request | None, route: str
+) -> None:
+    from litellm.proxy.proxy_server import llm_router, prisma_client, proxy_config, proxy_logging_obj
+
+    if route not in _CLAUDE_MODEL_ROUTES or llm_router is None:
+        return
+    if request is not None and request.scope.get(_CLAUDE_MODEL_NORMALIZED) is True:
+        return
+    requested: Final = _get_model_from_request_context(request_data, route, request, llm_router)
+    if not isinstance(requested, str) or requested != request_data.get("model"):
+        return
+    if not requested.startswith("claude-router-") and not requested.lower().endswith("[1m]"):
+        return
+    settings: Final = await proxy_config.get_hierarchical_router_settings(
+        user_api_key_dict=valid_token, prisma_client=prisma_client, proxy_logging_obj=proxy_logging_obj
+    )
+    aliases: Final = settings.get("model_group_alias") if isinstance(settings, Mapping) else None
+    source: Final = claude_code_requested_group(
+        requested, llm_router, valid_token.team_id, (valid_token.aliases, valid_token.team_model_aliases, aliases)
+    )
+    if request is not None:
+        request.scope[_CLAUDE_MODEL_NORMALIZED] = True
+    if source is None:
+        return
+    request_data["model"] = source
+    _safe_set_request_parsed_body(request=request, parsed_body=request_data)
+    if request is not None:
+        request._json = request_data
+        request._body = orjson.dumps(request_data)
+
+
 def _get_model_names_for_budget_checks(
     model: str | list[str] | None,
 ) -> list[str]:
@@ -1476,24 +1517,16 @@ async def _user_api_key_auth_builder(
                             user_id=user_id,
                             user_email=user_email,
                             team_id=team_id,
-                            team_alias=(team_object.team_alias if team_object is not None else None),
-                            team_tpm_limit=(team_object.tpm_limit if team_object is not None else None),
-                            team_rpm_limit=(team_object.rpm_limit if team_object is not None else None),
-                            team_models=(team_object.models if team_object is not None else []),
-                            team_metadata=(team_object.metadata if team_object is not None else None),
                             org_id=org_id,
                             end_user_id=end_user_id,
                             parent_otel_span=parent_otel_span,
                             jwt_claims=jwt_claims,
+                            **team_grants(team_object=team_object, team_membership=team_membership, user_id=user_id),
                         )
 
                     valid_token = UserAPIKeyAuth(
                         api_key=None,
                         team_id=team_id,
-                        team_alias=(team_object.team_alias if team_object is not None else None),
-                        team_tpm_limit=(team_object.tpm_limit if team_object is not None else None),
-                        team_rpm_limit=(team_object.rpm_limit if team_object is not None else None),
-                        team_models=(team_object.models if team_object is not None else []),
                         user_role=(
                             LitellmUserRoles(user_object.user_role)
                             if user_object is not None and user_object.user_role is not None
@@ -1507,17 +1540,8 @@ async def _user_api_key_auth_builder(
                         user_tpm_limit=(user_object.tpm_limit if user_object is not None else None),
                         user_rpm_limit=(user_object.rpm_limit if user_object is not None else None),
                         user_model_max_budget=(user_object.model_max_budget if user_object is not None else None),
-                        team_member_rpm_limit=(
-                            team_membership.safe_get_team_member_rpm_limit() if team_membership is not None else None
-                        ),
-                        team_member_tpm_limit=(
-                            team_membership.safe_get_team_member_tpm_limit() if team_membership is not None else None
-                        ),
-                        team_metadata=(team_object.metadata if team_object is not None else None),
                         jwt_claims=jwt_claims,
-                    )
-                    valid_token.team_object_permission = (
-                        team_object.object_permission if team_object is not None else None
+                        **team_grants(team_object=team_object, team_membership=team_membership, user_id=user_id),
                     )
 
                     # AUTO_REGISTER deferred from _resolve_jwt_to_virtual_key.
@@ -2666,6 +2690,7 @@ async def _run_centralized_common_checks(
 
     await _reserve_budget_after_common_checks(
         user_api_key_auth_obj=user_api_key_auth_obj,
+        request=request,
         request_data=request_data,
         route=route,
         llm_router=llm_router,
@@ -2701,6 +2726,7 @@ async def _reserve_budget_after_common_checks(
     general_settings: dict,
     end_user_id: str | None = None,
     end_user_object: LiteLLM_EndUserTable | None = None,
+    request: Request | None = None,
 ) -> None:
     user_api_key_auth_obj.budget_reservation = None
     if skip_budget_checks:
@@ -2726,6 +2752,7 @@ async def _reserve_budget_after_common_checks(
         end_user_object=end_user_object,
         apply_user_budget_to_team_keys=general_settings.get("apply_user_budget_to_team_keys") is True,
         fail_closed_budget_enforcement=general_settings.get("fail_closed_budget_enforcement") is True,
+        raw_body=await read_raw_json_body(request=request),
     )
 
 
@@ -2784,6 +2811,7 @@ async def _authorize_authenticated_request(
     """
     ## ENSURE DISABLE ROUTE WORKS ACROSS ALL USER AUTH FLOWS ##
     RouteChecks.should_call_route(route=route, valid_token=user_api_key_auth_obj, request=request)
+    await _normalize_claude_model(request_data, user_api_key_auth_obj, request, route)
 
     # Single authorization point. Builder paths MUST NOT call common_checks.
     # Route through the same exception handler the builder uses so
@@ -3147,6 +3175,7 @@ async def _enforce_key_and_fallback_model_access(
     Key-level model allowlist and client fallbacks (same as standard auth).
     Not included in common_checks — common_checks enforces team/user/project model access only.
     """
+    await _normalize_claude_model(request_data, valid_token, request, route)
     config: Final = valid_token.config
 
     if config != {}:
diff --git a/litellm/proxy/client/cli/README.md b/litellm/proxy/client/cli/README.md
index f7d9eb7da9a..4045857a237 100644
--- a/litellm/proxy/client/cli/README.md
+++ b/litellm/proxy/client/cli/README.md
@@ -490,7 +490,7 @@ lite codex exec "summarize the repo"
 
 Each command resolves your LiteLLM key (logging in via SSO when none is stored and you are at a terminal; otherwise it expects `LITELLM_PROXY_API_KEY` or `--api-key`), checks the key against the proxy so bad credentials fail immediately instead of deep inside the agent, exports the environment variables the agent reads, then replaces itself with the agent process.
 
-The right variables are picked per agent. Claude Code gets `ANTHROPIC_BASE_URL` (the proxy root, so it appends `/v1/messages`) and `ANTHROPIC_AUTH_TOKEN`, with any stray `ANTHROPIC_API_KEY` cleared so the proxy token wins, and `ENABLE_TOOL_SEARCH=true` (unless you already set it) so Claude Code keeps tool search on even though the base URL is a proxy rather than a first-party Anthropic host. It also gets `CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY=1` (again unless you already set it) so Claude Code v2.1.129+ fills its `/model` picker from the proxy's `/v1/models`; Claude Code only lists entries whose id contains `claude` or `anthropic`, and older versions ignore the variable. Export it as `0` to turn discovery off. Codex and OpenCode get `OPENAI_BASE_URL` (the proxy plus `/v1`) and `OPENAI_API_KEY`. Codex ignores `OPENAI_BASE_URL`, so it is additionally pointed at the proxy through a custom provider passed as `-c` config overrides (HTTP/SSE Responses transport, since the proxy does not speak the Responses WebSocket protocol). OpenCode additionally gets `OPENCODE_CONFIG_CONTENT` holding a generated `litellm` provider (`@ai-sdk/openai-compatible`, the proxy `/v1` URL, `{env:OPENAI_API_KEY}`) with one model entry per chat model your key can see on `/v1/models`, so its model picker mirrors the proxy without a hand-maintained `opencode.json`; OpenCode merges that over your own config files, and if you already export `OPENCODE_CONFIG_CONTENT` yours is left alone. When the list cannot be fetched, `lite opencode` says so on stderr and launches anyway.
+The right variables are picked per agent. Claude Code gets `ANTHROPIC_BASE_URL` (the proxy root, so it appends `/v1/messages`) and `ANTHROPIC_AUTH_TOKEN`, with any stray `ANTHROPIC_API_KEY` cleared so the proxy token wins, and `ENABLE_TOOL_SEARCH=true` (unless you already set it) so Claude Code keeps tool search on even though the base URL is a proxy rather than a first-party Anthropic host. It also gets `CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY=1` (again unless you already set it) so Claude Code v2.1.129+ fills its `/model` picker from the proxy's `/v1/models`; Claude Code only lists entries whose id contains `claude` or `anthropic`, so the proxy lists every other group to Claude Code as `claude-router-<UTF-8 hex of the group name>` and marks a group whose input window reaches 1M with `[1m]`, and a request on such an id is served by the group. Older Claude Code versions ignore the variable. Export it as `0` to turn discovery off. Codex and OpenCode get `OPENAI_BASE_URL` (the proxy plus `/v1`) and `OPENAI_API_KEY`. Codex ignores `OPENAI_BASE_URL`, so it is additionally pointed at the proxy through a custom provider passed as `-c` config overrides (HTTP/SSE Responses transport, since the proxy does not speak the Responses WebSocket protocol). OpenCode additionally gets `OPENCODE_CONFIG_CONTENT` holding a generated `litellm` provider (`@ai-sdk/openai-compatible`, the proxy `/v1` URL, `{env:OPENAI_API_KEY}`) with one model entry per chat model your key can see on `/v1/models`, so its model picker mirrors the proxy without a hand-maintained `opencode.json`; OpenCode merges that over your own config files, and if you already export `OPENCODE_CONFIG_CONTENT` yours is left alone. When the list cannot be fetched, `lite opencode` says so on stderr and launches anyway.
 
 pi ignores base-URL environment variables entirely, so `lite pi` (kept out of the `lite --help` command listing for now, but fully functional) wires it up differently: before handoff it fetches the models your key can use from the proxy's `/v1/models` (plus each model's context window and output cap from `/model_group/info`, when available) and syncs them into a `litellm` provider entry in pi's `~/.pi/agent/models.json` (honoring `PI_CODING_AGENT_DIR`), then starts pi on that provider's first model via an injected `--model litellm/<id>`. Only that one provider entry is rewritten; the rest of the file, including any other custom providers, is left alone. The entry references the key as `$LITELLM_PROXY_API_KEY`, which the wrapper exports for the session, so the token itself never lands on disk and plain `pi` outside the wrapper simply shows the litellm models as unavailable. Your own flags come after the injected pin, so `lite pi --model litellm/<other-id>` wins, and inside the TUI the `/model` picker lists every synced litellm model.
 
@@ -508,7 +508,7 @@ The credential is short-lived by design (default 24h, configurable via `LITELLM_
 
 ### Route Every Claude Code Session Through the Proxy
 
-`lite claude` wraps a single invocation, but `lite up` goes further: it patches `~/.claude/settings.json`, Claude Code's own config file, so that every Claude Code session started afterward -- from any terminal, launched normally with just `claude`, no wrapper needed -- routes through your LiteLLM proxy. It sets `env.ANTHROPIC_BASE_URL` to the proxy URL, `env.ENABLE_TOOL_SEARCH` to `true` and `env.CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY` to `1` when those keys are missing, and `apiKeyHelper` to a `lite auth print-token` invocation, drops any stray static `ANTHROPIC_API_KEY` so the helper-issued token wins, and leaves every other setting in the file untouched. It backs up the original file before patching it.
+`lite claude` wraps a single invocation, but `lite up` goes further: it patches `~/.claude/settings.json`, Claude Code's own config file, so that every Claude Code session started afterward -- from any terminal, launched normally with just `claude`, no wrapper needed -- routes through your LiteLLM proxy. It sets `env.ANTHROPIC_BASE_URL` to the proxy URL, `env.ENABLE_TOOL_SEARCH` to `true` and `env.CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY` to `1` when those keys are missing, and `apiKeyHelper` to a `lite auth print-token` invocation, drops any stray static `ANTHROPIC_API_KEY` or `ANTHROPIC_AUTH_TOKEN` so the helper-issued token wins, and leaves every other setting in the file untouched. It backs up the original file before patching it.
 
 Two things need to already be true: you've run `lite login` (or `lite login --pkce`, whose key the helper renews on its own), since the apiKeyHelper depends on that stored token, and the proxy is already reachable, since `lite up` does not start one for you.
 
@@ -532,12 +532,28 @@ Cursor is not supported: it has no equivalent file-based config to hot-patch thi
 lite --base-url https://your-proxy.example.com login --config-claude
 ```
 
-It writes the same settings `lite up` does, `env.ANTHROPIC_BASE_URL`, `env.ENABLE_TOOL_SEARCH`, `env.CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY`, and `apiKeyHelper`, but persistently: there is no backup, nothing to restore, and no foreground process to keep alive. Every other key in `~/.claude/settings.json` is preserved, the file is created if it does not exist, and it is written atomically with owner-only permissions. Plain `lite login` is unchanged; nothing happens to your Claude Code config unless you pass the flag.
+It writes the same settings `lite up` does, `env.ANTHROPIC_BASE_URL`, `env.ENABLE_TOOL_SEARCH`, `env.CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY`, and `apiKeyHelper`, but persistently: no foreground process to keep alive, and `lite unconfigure claude` restores what it changed (see below). Every other key in `~/.claude/settings.json` is preserved, the file is created if it does not exist, and it is written atomically with owner-only permissions. Plain `lite login` is unchanged; nothing happens to your Claude Code config unless you pass the flag.
 
 Because the credential is reached through `apiKeyHelper` rather than copied into the file, a later `lite login` refreshes it with no further action: Claude Code re-runs the helper on every request and picks up whatever token the most recent login stored. Nothing secret is written to `settings.json`.
 
 Run it again to point Claude Code at a different proxy; the base URL and the helper are both rewritten. `lite up` and `--config-claude` manage the same file, so the flag refuses to run while a `lite up` session holds a backup, and tells you to run `lite down` first, rather than writing settings that `lite up` would silently revert when it stops.
 
+#### Configuring Claude Code Once, With a Virtual Key or Your Login
+
+`lite configure claude` wires Claude Code up persistently and `lite unconfigure claude` puts things back. It is what `lite login --config-claude` does, plus a pinned model and an undo, and it also takes a long-lived virtual key when that is what you have:
+
+```bash
+curl -fsSL https://raw.githubusercontent.com/BerriAI/litellm/main/scripts/install.sh | sh
+lite --base-url https://your-proxy.example.com configure claude --api-key sk-... --model claude-auto
+claude
+```
+
+With `--api-key` (or `lite --api-key` / `LITELLM_PROXY_API_KEY`) the key is written into `env.ANTHROPIC_AUTH_TOKEN`. Without one, your `lite login` credential is used the way `--config-claude` uses it, through `apiKeyHelper`, so a later `lite login` (or a `--pkce` renewal) picks up on its own and nothing secret lands in the file; a missing or stale login is refreshed first. Either way the command checks the key against `GET /v1/models`, then patches `~/.claude/settings.json`: `env.ANTHROPIC_BASE_URL`, the credential, and `env.ENABLE_TOOL_SEARCH` and `env.CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY` when those are missing, so Claude Code's `/model` picker lists the proxy's models (under `claude-router-<UTF-8 hex of the group name>` for a group whose id contains neither `claude` nor `anthropic`, since Claude Code lists only those) and you pick between them as usual. Claude Code keeps its own default model until you switch, so that id has to exist on the proxy for the first message to go through; `--model` (or the interactive prompt below) sets the model Claude Code starts on instead, as the top-level `model` key, which has to be on `/v1/models` for the key. Nothing forces Claude Code's sub-agent or background tiers onto a proxy model, so those built-in ids need to exist on the proxy too; `lite autoroute up` is the mode that pins every tier to one group. Claude Code treats a name it does not know as an unknown model: it prints a one-line `unrecognized_model` note, assumes a 200k context window (the proxy appends `[1m]` for a group whose configured or known input window reaches 1M) and sends no thinking parameters for it, so name the group like a Claude model id to change that. The other credential slots (`env.ANTHROPIC_API_KEY`, a stale `env.ANTHROPIC_AUTH_TOKEN` or `apiKeyHelper`) are removed so they cannot fight the one written. Every other setting is preserved and the file is written atomically with owner-only permissions; if `settings.json` is a symlink into a dotfiles repository, the key is written through to that target and the command says so, so keep it out of version control
+
+Plain `lite configure`, with no agent named, asks the same things interactively: which agents to wire (Claude Code today) and which of the proxy's models to start on, picked from `/v1/models` with a type-to-filter prompt
+
+What the command changed is recorded in `~/.litellm/claude_configure_state.json` (previous values plus fingerprints of what was written, never a second copy of the key). `lite unconfigure claude` restores each of those keys only if it still holds what `configure` wrote, so anything you changed since is left alone and named in the output; a `settings.json` or `env` object that only existed because of `configure` is removed again. Ownership moves only by a write: running `configure` again (a re-login is one) refreshes the record only for the keys its merge changed, keeps the original snapshot of a key that still holds what it wrote, and snapshots afresh a key you changed in between, so `unconfigure` brings back whatever the repeat displaced and never adopts your edit as its own. A credential (`env.ANTHROPIC_API_KEY`, `env.ANTHROPIC_AUTH_TOKEN`, `apiKeyHelper`) is put back only when the restored file points at the `ANTHROPIC_BASE_URL` it was captured next to; otherwise it stays removed, the output says which server it belonged to, and the receipt is kept so pointing the URL back and running `unconfigure` again finishes the job. It also undoes `lite login --config-claude`, which writes through the same path. Like `--config-claude`, both refuse to run while a `lite up` or `lite autoroute up` session holds a backup, and that check comes before any login prompt or request
+
 ### QA Complexity-Based Auto-Routing Against Your Real Proxy
 
 `lite autoroute` lets you try LiteLLM's complexity-based auto-routing -- picking a cheaper or more expensive model depending on how complex a prompt looks -- against models your key already has access to on your real, running proxy, without editing that proxy's `config.yaml` and without any real request ever bypassing it. It builds a second, throwaway proxy locally that forwards every request back to your real proxy, and points Claude Code at that local proxy for the duration of the session.
@@ -584,7 +600,7 @@ An interactive wizard. It runs the same model-group discovery as above, splits t
 
 The wizard writes the result to `~/.litellm/autorouter/config.yaml` with `0600` permissions, since the file embeds your real proxy API key. Every model referenced anywhere in that config -- tier targets, the classifier model, the embedding model -- becomes its own `litellm_proxy/<model-name>` deployment whose `api_base` and `api_key` point back at your real proxy. That is the trick that keeps your real proxy's config untouched: every actual network call this generates, whether it is the routed completion, an LLM-classifier call, or an embedding call, forwards transparently through your real, already-running proxy with your real key.
 
-You do not need to tell Claude Code to request `autorouter` by name yourself: `lite autoroute up` also sets `ANTHROPIC_DEFAULT_SONNET_MODEL`, `ANTHROPIC_DEFAULT_HAIKU_MODEL`, and `ANTHROPIC_DEFAULT_OPUS_MODEL` to `autorouter` in `~/.claude/settings.json`, so every one of Claude Code's own model tiers requests it directly regardless of `/model` or whatever it defaults to otherwise. (A bare `model_name: "*"` deployment looks like the obvious way to catch any request instead, but litellm's Router looks up auto-router deployments by the literal requested model string with no wildcard resolution, so a `"*"` entry would never actually match real traffic -- these env var overrides are what makes it work.)
+You do not need to tell Claude Code to request `autorouter` by name yourself: `lite autoroute up` also sets the top-level `model` and `ANTHROPIC_DEFAULT_SONNET_MODEL`, `ANTHROPIC_DEFAULT_HAIKU_MODEL`, `ANTHROPIC_DEFAULT_OPUS_MODEL` and `ANTHROPIC_DEFAULT_FABLE_MODEL` to `autorouter` in `~/.claude/settings.json` (and `CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY` to `1` when missing, like every other wiring), so every one of Claude Code's own model tiers requests it directly regardless of `/model` or whatever it defaults to otherwise. (A bare `model_name: "*"` deployment looks like the obvious way to catch any request instead, but litellm's Router looks up auto-router deployments by the literal requested model string with no wildcard resolution, so a `"*"` entry would never actually match real traffic -- these env var overrides are what makes it work.)
 
 You must run `configure` at least once before `up`; running `up` first fails with a clear error telling you to configure first.
 
diff --git a/litellm/proxy/client/cli/commands/agents.py b/litellm/proxy/client/cli/commands/agents.py
index 7a0ae9dc955..bf2a784f590 100644
--- a/litellm/proxy/client/cli/commands/agents.py
+++ b/litellm/proxy/client/cli/commands/agents.py
@@ -4,6 +4,7 @@ import subprocess
 import sys
 from collections.abc import Callable, Mapping, Sequence
 from dataclasses import dataclass
+from pathlib import Path
 from types import MappingProxyType
 from typing import Final, TypeAlias
 
@@ -12,10 +13,12 @@ import requests
 from pydantic import BaseModel, TypeAdapter, ValidationError
 
 from .auth import CliContextObj, context_secret_vault, get_stored_api_key, login
+from .claude_settings import claude_settings_path, lite_api_key_helper_configured
 from .cmd_quoting import quote_for_cmd
 from .pi import (
     LITELLM_PROXY_API_KEY_ENV,
     PI_PROVIDER_NAME,
+    ListingFailure,
     PiSyncError,
     fetch_model_ids,
     fetch_model_limits,
@@ -83,6 +86,8 @@ def build_agent_env(
     base_url: str,
     api_key: str,
     profiles: frozenset[str],
+    *,
+    export_anthropic_token: bool = True,
 ) -> dict[str, str]:
     """Return a copy of base_env wired to route the agent through the proxy.
 
@@ -97,12 +102,19 @@ def build_agent_env(
     proxy's /v1/models; likewise left alone when already set.
     pi ignores both base URL variables and instead resolves $LITELLM_PROXY_API_KEY
     from its synced models.json provider entry.
+
+    With export_anthropic_token=False the bearer is left out (and any inherited
+    one dropped) so Claude Code asks its configured apiKeyHelper instead; Claude
+    Code prefers ANTHROPIC_AUTH_TOKEN over the helper and warns when both are set.
     """
     env: Final = dict(base_env)
     root: Final = base_url.rstrip("/")
     if PROFILE_ANTHROPIC in profiles:
         env[ANTHROPIC_BASE_URL_ENV] = root
-        env[ANTHROPIC_AUTH_TOKEN_ENV] = api_key
+        if export_anthropic_token:
+            env[ANTHROPIC_AUTH_TOKEN_ENV] = api_key
+        else:
+            env.pop(ANTHROPIC_AUTH_TOKEN_ENV, None)
         env.pop(ANTHROPIC_API_KEY_ENV, None)
         if ENABLE_TOOL_SEARCH_ENV not in env:
             env[ENABLE_TOOL_SEARCH_ENV] = ENABLE_TOOL_SEARCH_VALUE
@@ -165,7 +177,9 @@ def prepare_pi(
     """
     ids: Final = fetch_model_ids(base_url, api_key, get=get)
     if isinstance(ids, PiSyncError):
-        raise AgentRunError(ids.message)
+        raise AgentRunError(
+            f"{ids.message} pi would have nothing to run." if ids.kind is ListingFailure.EMPTY else ids.message
+        )
     limits: Final = fetch_model_limits(base_url, api_key, get=get)
     path: Final = models_json_path(base_env)
     error: Final = sync_models_json(path, base_url, ids, limits)
@@ -460,6 +474,7 @@ def run_agent(
     launcher: Callable[[str, Sequence[str], Mapping[str, str]], None] = _hand_off,
     reattach_terminal: Callable[[], None] | None = None,
     preparers: Mapping[str, _Preparer] = MappingProxyType(_PREPARERS),
+    export_anthropic_token: bool = True,
 ) -> None:
     """Validate, wire the environment, and hand off to the agent.
 
@@ -491,7 +506,9 @@ def run_agent(
 
     env: Final = MappingProxyType(
         {
-            **build_agent_env(env_before_sync, base_url, api_key, profiles),
+            **build_agent_env(
+                env_before_sync, base_url, api_key, profiles, export_anthropic_token=export_anthropic_token
+            ),
             **(_NO_EXTRA_ENV if isinstance(synced, ModelSyncSkipped) else synced),
         }
     )
@@ -529,14 +546,26 @@ def resolve_api_key(ctx: click.Context) -> str:
 _SKIP_VERIFY_HELP: Final = "Skip the pre-launch key check against the proxy."
 
 
+def _helper_supplies_token(
+    ctx_obj: CliContextObj, base_url: str, profiles: frozenset[str], settings_path: Path
+) -> bool:
+    if PROFILE_ANTHROPIC not in profiles or not ctx_obj.get("api_key_from_token_file"):
+        return False
+    return lite_api_key_helper_configured(base_url, settings_path)
+
+
 def _launch(ctx: click.Context, binary: str, args: Sequence[str], *, skip_verify: bool) -> None:
     ctx_obj: Final[CliContextObj] = ctx.obj
     base_url: Final = ctx_obj["base_url"]
     started_interactive: Final = _is_interactive()
     api_key: Final = resolve_api_key(ctx)
 
-    display_name, _ = agent_profile(binary)
+    display_name, profiles = agent_profile(binary)
+    settings_path: Final = claude_settings_path(os.environ)
+    helper_supplies_token: Final = _helper_supplies_token(ctx_obj, base_url, profiles, settings_path)
     click.echo(f"litellm: routing {display_name} through proxy at {base_url.rstrip('/')}")
+    if helper_supplies_token:
+        click.echo(f"litellm: {display_name} reads its key from the apiKeyHelper in {settings_path}")
 
     try:
         run_agent(
@@ -545,6 +574,7 @@ def _launch(ctx: click.Context, binary: str, args: Sequence[str], *, skip_verify
             [binary, *args],
             skip_verify=skip_verify,
             reattach_terminal=(_restore_controlling_terminal if started_interactive else None),
+            export_anthropic_token=not helper_supplies_token,
         )
     except AgentRunError as e:
         raise click.ClickException(str(e))
diff --git a/litellm/proxy/client/cli/commands/auth.py b/litellm/proxy/client/cli/commands/auth.py
index 12a288202b6..4f704afe9d6 100644
--- a/litellm/proxy/client/cli/commands/auth.py
+++ b/litellm/proxy/client/cli/commands/auth.py
@@ -1,3 +1,4 @@
+import os
 import sys
 import time
 import webbrowser
@@ -40,10 +41,16 @@ from litellm.litellm_core_utils.cli_token_utils import (
 )
 
 from .claude_settings import (
-    CLAUDE_SETTINGS_PATH,
-    SETTINGS_FILE_OWNERS,
+    STARTING_MODEL_ROLE,
+    ApiKeyHelper,
     ClaudeSettingsError,
-    write_claude_settings,
+    KeepModel,
+    claude_settings_path,
+    configure_claude_settings,
+    configure_state_path,
+    refuse_while_owned,
+    resolve_api_key_helper,
+    settings_file_owners,
 )
 from .pkce_login import (
     Http,
@@ -778,13 +785,24 @@ def _render_and_prompt_for_team_selection(teams: list[CliTeam]) -> str | None:
 
 
 def _configure_claude_code(base_url: str) -> None:
-    """Point Claude Code at base_url by patching ~/.claude/settings.json."""
+    """Point Claude Code at base_url by patching the settings.json it reads, undoable with `lite unconfigure claude`."""
+    settings_path: Final = claude_settings_path(os.environ)
     try:
-        write_claude_settings(base_url, CLAUDE_SETTINGS_PATH, SETTINGS_FILE_OWNERS)
+        configure_claude_settings(
+            base_url,
+            ApiKeyHelper(resolve_api_key_helper(base_url)),
+            KeepModel(),
+            settings_path,
+            configure_state_path(settings_path),
+            settings_file_owners(settings_path),
+        )
     except ClaudeSettingsError as e:
         raise click.ClickException(f"Logged in, but could not configure Claude Code: {e}")
-    click.echo(f"\nConfigured Claude Code: {CLAUDE_SETTINGS_PATH} now routes through {base_url.rstrip('/')}.")
-    click.echo("Your other Claude Code settings were left untouched. Restart Claude Code to pick this up.")
+    click.echo(f"\nConfigured Claude Code: {settings_path} now routes through {base_url.rstrip('/')}.")
+    click.echo(
+        "Your other Claude Code settings were left untouched. Restart Claude Code to pick this up. "
+        f"Undo with `lite unconfigure claude`; `lite configure claude --model` sets {STARTING_MODEL_ROLE}."
+    )
 
 
 def _finish_login(base_url: str, api_key: str, config_claude: bool, stored: SecretSave) -> None:
@@ -853,6 +871,12 @@ def login(ctx: click.Context, config_claude: bool, pkce: bool) -> None:
 
     ctx_obj: Final[CliContextObj] = ctx.obj
     base_url: Final = ctx_obj["base_url"]
+    if config_claude:
+        settings_path: Final = claude_settings_path(os.environ)
+        try:
+            refuse_while_owned(settings_path, settings_file_owners(settings_path))
+        except ClaudeSettingsError as e:
+            raise click.ClickException(f"Cannot configure Claude Code, so not logging in: {e}")
 
     try:
         if pkce:
diff --git a/litellm/proxy/client/cli/commands/autoroute/commands.py b/litellm/proxy/client/cli/commands/autoroute/commands.py
index 26d45138a27..86701f186fd 100644
--- a/litellm/proxy/client/cli/commands/autoroute/commands.py
+++ b/litellm/proxy/client/cli/commands/autoroute/commands.py
@@ -14,11 +14,13 @@ from ..claude_settings import (
     AUTOROUTE_BACKUP_PATH,
     CLAUDE_SETTINGS_PATH,
     ClaudeSettingsError,
+    StaticToken,
     load_json_or_empty,
+    merge_claude_settings,
 )
 from ..up import BackupRecord as ClaudeBackupRecord
 from ..up import restore_claude_settings, write_backup
-from .config import master_key_from_config
+from .config import AUTOROUTER_MODEL_NAME, master_key_from_config
 from .process import (
     CONFIG_PATH,
     DEFAULT_AUTOROUTE_PORT,
@@ -37,7 +39,6 @@ from .process import (
     terminate,
     write_pid_record,
 )
-from .settings import merge_claude_settings_static_token
 from .wizard import run_configure_wizard
 
 _GENERATED_CONFIG_ADAPTER: Final = TypeAdapter(dict[str, JsonValue])
@@ -156,7 +157,9 @@ def up(port: int) -> None:
             ClaudeBackupRecord(existed=original_existed, content=original_settings if original_existed else None),
             AUTOROUTE_BACKUP_PATH,
         )
-        merged: Final = merge_claude_settings_static_token(original_settings, base_url, master_key)
+        merged: Final = merge_claude_settings(
+            original_settings, base_url, StaticToken(master_key), AUTOROUTER_MODEL_NAME, AUTOROUTER_MODEL_NAME
+        )
         CLAUDE_SETTINGS_PATH.parent.mkdir(parents=True, exist_ok=True)
         with secure_create(CLAUDE_SETTINGS_PATH) as f:
             json.dump(merged, f, indent=2)
diff --git a/litellm/proxy/client/cli/commands/autoroute/settings.py b/litellm/proxy/client/cli/commands/autoroute/settings.py
deleted file mode 100644
index 60729b5410d..00000000000
--- a/litellm/proxy/client/cli/commands/autoroute/settings.py
+++ /dev/null
@@ -1,51 +0,0 @@
-from typing import Final
-
-from pydantic import JsonValue
-
-from .config import AUTOROUTER_MODEL_NAME
-
-ENV_KEY: Final = "env"
-API_KEY_HELPER_KEY: Final = "apiKeyHelper"
-ANTHROPIC_API_KEY_KEY: Final = "ANTHROPIC_API_KEY"
-ANTHROPIC_AUTH_TOKEN_KEY: Final = "ANTHROPIC_AUTH_TOKEN"
-ANTHROPIC_BASE_URL_KEY: Final = "ANTHROPIC_BASE_URL"
-ENABLE_TOOL_SEARCH_KEY: Final = "ENABLE_TOOL_SEARCH"
-ENABLE_TOOL_SEARCH_VALUE: Final = "true"
-# Force every one of Claude Code's own model tiers to request the auto-router by name.
-# Router's auto-router registry is keyed by the literal requested model string
-# (litellm/router.py:10711-10717) with no wildcard/pattern resolution, so a bare "*"
-# model_name can never work as a catch-all -- these overrides are what actually makes
-# Claude Code send "autorouter" regardless of /model or its own version-specific defaults.
-ANTHROPIC_DEFAULT_MODEL_ENV_KEYS: Final = (
-    "ANTHROPIC_DEFAULT_SONNET_MODEL",
-    "ANTHROPIC_DEFAULT_HAIKU_MODEL",
-    "ANTHROPIC_DEFAULT_OPUS_MODEL",
-)
-
-
-def merge_claude_settings_static_token(
-    settings: dict[str, JsonValue], base_url: str, auth_token: str
-) -> dict[str, JsonValue]:
-    """Return a new settings dict wired to a local ephemeral proxy with a static token.
-
-    Unlike up.py's merge_claude_settings (which sets apiKeyHelper for a long-lived, real
-    remote proxy needing refreshable SSO tokens), this proxy is ephemeral and its key is the
-    locally persisted autoroute master key, so a plain env var is simpler and correct. Any
-    existing apiKeyHelper is cleared so it can't fight with the static token.
-    """
-    raw_env: Final = settings.get(ENV_KEY, {})
-    base_env: Final = raw_env if isinstance(raw_env, dict) else {}
-    env: Final[dict[str, JsonValue]] = {
-        ENABLE_TOOL_SEARCH_KEY: ENABLE_TOOL_SEARCH_VALUE,
-        **base_env,
-        ANTHROPIC_BASE_URL_KEY: base_url.rstrip("/"),
-        ANTHROPIC_AUTH_TOKEN_KEY: auth_token,
-        **{key: AUTOROUTER_MODEL_NAME for key in ANTHROPIC_DEFAULT_MODEL_ENV_KEYS},
-    }
-    env.pop(ANTHROPIC_API_KEY_KEY, None)
-    merged: Final[dict[str, JsonValue]] = {**settings, ENV_KEY: env}
-    merged.pop(API_KEY_HELPER_KEY, None)
-    return merged
-
-
-__all__ = ["merge_claude_settings_static_token"]
diff --git a/litellm/proxy/client/cli/commands/claude_settings.py b/litellm/proxy/client/cli/commands/claude_settings.py
index 5e3ce95f088..d0ee507f0b2 100644
--- a/litellm/proxy/client/cli/commands/claude_settings.py
+++ b/litellm/proxy/client/cli/commands/claude_settings.py
@@ -1,37 +1,71 @@
 """Shared handling of Claude Code's ~/.claude/settings.json.
 
-`lite up` patches this file temporarily and restores it on exit; `lite login
---config-claude` patches it persistently. Both need the same merge and the same
-apiKeyHelper command, and `up` already imports from `auth`, so the shared parts
-live here rather than in either command module.
+`lite up` and `lite autoroute up` patch this file temporarily and restore it on
+exit; `lite login --config-claude` and `lite configure claude` patch it
+persistently and record how to undo it. All of them need the same merge and the
+same apiKeyHelper command, and `up` already imports from `auth`, so the shared
+parts live here rather than in any one command module.
 """
 
+import hashlib
+import json
 import shlex
 import shutil
 import sys
-from collections.abc import Mapping, Sequence
+from collections.abc import Callable, Mapping, Sequence
 from dataclasses import dataclass
+from functools import reduce
+from itertools import chain
 from pathlib import Path
-from typing import Final
+from types import MappingProxyType
+from typing import Final, TypeAlias
 
-from pydantic import JsonValue, TypeAdapter, ValidationError
+from pydantic import BaseModel, ConfigDict, JsonValue, TypeAdapter, ValidationError
 
-from litellm.litellm_core_utils.private_json import write_private_json
+from litellm.litellm_core_utils.private_json import (
+    commit_staged_json,
+    discard_staged_json,
+    ensure_private_dir,
+    stage_private_json,
+)
 
 from .cmd_quoting import quote_for_cmd
 
 ENV_KEY: Final = "env"
 API_KEY_HELPER_KEY: Final = "apiKeyHelper"
+MODEL_KEY: Final = "model"
 ANTHROPIC_BASE_URL_KEY: Final = "ANTHROPIC_BASE_URL"
+ANTHROPIC_AUTH_TOKEN_KEY: Final = "ANTHROPIC_AUTH_TOKEN"
 ANTHROPIC_API_KEY_KEY: Final = "ANTHROPIC_API_KEY"
 ENABLE_TOOL_SEARCH_KEY: Final = "ENABLE_TOOL_SEARCH"
 ENABLE_TOOL_SEARCH_VALUE: Final = "true"
 ENABLE_GATEWAY_MODEL_DISCOVERY_KEY: Final = "CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"
 ENABLE_GATEWAY_MODEL_DISCOVERY_VALUE: Final = "1"
+ANTHROPIC_DEFAULT_MODEL_ENV_KEYS: Final = (
+    "ANTHROPIC_DEFAULT_SONNET_MODEL",
+    "ANTHROPIC_DEFAULT_HAIKU_MODEL",
+    "ANTHROPIC_DEFAULT_OPUS_MODEL",
+    "ANTHROPIC_DEFAULT_FABLE_MODEL",
+)
+OWNED_ENV_KEYS: Final = (
+    ENABLE_TOOL_SEARCH_KEY,
+    ENABLE_GATEWAY_MODEL_DISCOVERY_KEY,
+    ANTHROPIC_BASE_URL_KEY,
+    ANTHROPIC_AUTH_TOKEN_KEY,
+    ANTHROPIC_API_KEY_KEY,
+)
+OWNED_TOP_LEVEL_KEYS: Final = (API_KEY_HELPER_KEY, MODEL_KEY)
+OWNED_PATHS: Final = (*(f"{ENV_KEY}.{key}" for key in OWNED_ENV_KEYS), *OWNED_TOP_LEVEL_KEYS)
+_CREDENTIAL_ENV_KEYS: Final = frozenset((ANTHROPIC_API_KEY_KEY, ANTHROPIC_AUTH_TOKEN_KEY))
+_CREDENTIAL_PATHS: Final = (*(f"{ENV_KEY}.{key}" for key in sorted(_CREDENTIAL_ENV_KEYS)), API_KEY_HELPER_KEY)
+_BASE_URL_PATH: Final = f"{ENV_KEY}.{ANTHROPIC_BASE_URL_KEY}"
+STARTING_MODEL_ROLE: Final = "the /model picker's default row, the model Claude Code starts on"
 
 CLAUDE_SETTINGS_PATH: Final = Path.home() / ".claude" / "settings.json"
+CLAUDE_CONFIG_DIR_ENV: Final = "CLAUDE_CONFIG_DIR"
 BACKUP_PATH: Final = Path.home() / ".litellm" / "claude_settings_backup.json"
 AUTOROUTE_BACKUP_PATH: Final = Path.home() / ".litellm" / "autorouter" / "claude_settings_backup.json"
+CONFIGURE_STATE_PATH: Final = Path.home() / ".litellm" / "claude_configure_state.json"
 
 
 @dataclass(frozen=True, slots=True)
@@ -55,6 +89,129 @@ class ClaudeSettingsError(Exception):
     """Raised for any user-actionable failure while reading or writing Claude Code settings."""
 
 
+def claude_settings_path(environ: Mapping[str, str]) -> Path:
+    """The settings.json Claude Code reads: under CLAUDE_CONFIG_DIR when set, else ~/.claude/settings.json."""
+    config_dir: Final = environ.get(CLAUDE_CONFIG_DIR_ENV, "")
+    if not config_dir:
+        return CLAUDE_SETTINGS_PATH
+    return Path(config_dir).expanduser() / "settings.json"
+
+
+def _is_default_settings_file(settings_path: Path) -> bool:
+    return settings_path.resolve() == CLAUDE_SETTINGS_PATH.resolve()
+
+
+def settings_file_owners(settings_path: Path) -> tuple[SettingsFileOwner, ...]:
+    """The commands whose backups guard settings_path: `lite up` and `lite autoroute up` only ever manage the default file."""
+    return SETTINGS_FILE_OWNERS if _is_default_settings_file(settings_path) else ()
+
+
+def configure_state_path(settings_path: Path) -> Path:
+    """The receipt describing settings_path: the default file keeps CONFIGURE_STATE_PATH, and any other file
+    (a CLAUDE_CONFIG_DIR) gets its own beside it, keyed by its resolved path, so two settings files never
+    share one undo record."""
+    if _is_default_settings_file(settings_path):
+        return CONFIGURE_STATE_PATH
+    digest: Final = hashlib.sha256(str(settings_path.resolve()).encode()).hexdigest()
+    return CONFIGURE_STATE_PATH.parent / CONFIGURE_STATE_PATH.stem / f"{digest}.json"
+
+
+@dataclass(frozen=True, slots=True)
+class StaticToken:
+    """A long-lived virtual key, written into env.ANTHROPIC_AUTH_TOKEN."""
+
+    token: str
+
+
+@dataclass(frozen=True, slots=True)
+class ApiKeyHelper:
+    """A `lite auth print-token` command Claude Code runs per request, so a login renews in place."""
+
+    command: str
+
+
+ClaudeCredential: TypeAlias = StaticToken | ApiKeyHelper
+
+
+@dataclass(frozen=True, slots=True)
+class KeepModel:
+    """Leave the top-level `model` as it is, the user's or an earlier configure's (a re-login)."""
+
+
+@dataclass(frozen=True, slots=True)
+class UnpinModel:
+    """Let go of a `model` an earlier configure pinned; one the user set themselves stays."""
+
+
+@dataclass(frozen=True, slots=True)
+class StartOn:
+    """Pin the top-level `model`, the row Claude Code starts on."""
+
+    model: str
+
+
+ModelChoice: TypeAlias = KeepModel | UnpinModel | StartOn
+
+
+class OwnedValue(BaseModel):
+    """What one key held at a moment in time; `present=False` is an absent key, not a null one."""
+
+    model_config = ConfigDict(frozen=True)
+
+    present: bool
+    value: JsonValue = None
+
+
+class ConfigureReceipt(BaseModel):
+    """What `lite configure claude` found and what it owns, keyed by dotted path (`env.X` or a top-level key).
+
+    Ownership moves only by a write: `written` fingerprints the keys some configure changed, at the
+    value it wrote; a repeat configure refreshes a fingerprint only for a key its merge changed and
+    carries the earlier one otherwise, so a key the user edited in between stops matching and is left
+    alone. `previous` is what each key held before configure took it over; a repeat keeps the earlier
+    snapshot while the key still holds our value and snapshots afresh otherwise, so whatever the
+    repeat displaces is what comes back. `endpoints` is the ANTHROPIC_BASE_URL each credential slot
+    was captured beside, so a credential is only ever put back next to the server it was issued for.
+    No fingerprint is a second copy of a token.
+    """
+
+    model_config = ConfigDict(frozen=True)
+
+    file_existed: bool
+    env_present: bool
+    env_was_object: bool
+    previous: Mapping[str, OwnedValue]
+    written: Mapping[str, str]
+    endpoints: Mapping[str, OwnedValue]
+
+
+@dataclass(frozen=True, slots=True)
+class WithheldCredential:
+    """A credential left removed: captured beside `endpoint`, while the restored file points elsewhere."""
+
+    key: str
+    endpoint: str
+
+
+@dataclass(frozen=True, slots=True)
+class UnconfigureOutcome:
+    """Keys whose value unconfigure changed back, keys the user changed since and so were left as they
+    are, credentials withheld (the receipt is kept for them, so a later unconfigure can finish once the
+    URL points back), and whether no settings file remains."""
+
+    restored: tuple[str, ...]
+    kept: tuple[str, ...]
+    withheld: tuple[WithheldCredential, ...] = ()
+    file_removed: bool = False
+
+
+@dataclass(frozen=True, slots=True)
+class _Claim:
+    previous: OwnedValue
+    written: str | None
+    endpoint: OwnedValue | None
+
+
 def load_json_or_empty(path: Path) -> dict[str, JsonValue]:
     try:
         content: Final = path.read_bytes() if path.exists() else b""
@@ -70,29 +227,104 @@ def load_json_or_empty(path: Path) -> dict[str, JsonValue]:
         )
 
 
-def merge_claude_settings(
-    settings: Mapping[str, JsonValue], base_url: str, api_key_helper: str
-) -> dict[str, JsonValue]:
-    """Return a new settings dict wired to route Claude Code through the proxy.
+def _env_object(settings: Mapping[str, JsonValue], path: Path) -> Mapping[str, JsonValue]:
+    raw_env: Final = settings.get(ENV_KEY)
+    if raw_env is None:
+        return MappingProxyType({})
+    if not isinstance(raw_env, dict):
+        raise ClaudeSettingsError(
+            f'{path} has a non-object "{ENV_KEY}" value, which this would discard. Fix or remove it, then retry.'
+        )
+    return raw_env
 
-    Only env.ANTHROPIC_BASE_URL and the top-level apiKeyHelper are overridden; a
-    stray env.ANTHROPIC_API_KEY is dropped so it cannot outrank the helper-issued
-    token (same reasoning as build_agent_env in agents.py). ENABLE_TOOL_SEARCH
-    defaults to true because Claude Code turns tool search off when
-    ANTHROPIC_BASE_URL is not a first-party Anthropic host, and
-    CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY defaults to 1 so the /model picker
-    is filled from the proxy's /v1/models; existing values of both are left
-    alone. Every other key is preserved untouched.
+
+def refuse_while_owned(settings_path: Path, owners: Sequence[SettingsFileOwner]) -> None:
+    """Refuse while `lite up` or `lite autoroute up` holds a backup it will restore over any write; a
+    purely local check, so commands run it before any login prompt or request."""
+    for owner in owners:
+        if owner.backup_path.exists():
+            raise ClaudeSettingsError(
+                f"`{owner.start_command}` is currently managing {settings_path} (backup at "
+                f"{owner.backup_path}) and will restore it when it stops. "
+                f"Run `{owner.stop_command}` first, then retry."
+            )
+
+
+def _write_target(settings_path: Path) -> Path:
+    """Write through a symlinked settings.json rather than replacing the link, which would silently
+    detach a file symlinked into a dotfiles repo."""
+    try:
+        return settings_path.resolve() if settings_path.is_symlink() else settings_path
+    except OSError as e:
+        raise ClaudeSettingsError(f"Could not resolve {settings_path}: {e}") from e
+
+
+def _stage(path: Path, document: Mapping[str, object]) -> str:
+    try:
+        return stage_private_json(str(path), document)
+    except OSError as e:
+        raise ClaudeSettingsError(f"Could not write {path}: {e}") from e
+
+
+def _land(
+    path: Path,
+    staged: str | None,
+    also_discard: Sequence[str | None] = (),
+    commit: Callable[[str, str], None] = commit_staged_json,
+) -> None:
+    """Commit a staged file to `path`, or remove `path` when nothing is staged for it. The one place a
+    filesystem error becomes a ClaudeSettingsError; on failure the operation's other staged files are
+    discarded, so no temp file holding a token is left behind."""
+    try:
+        if staged is None:
+            path.unlink(missing_ok=True)
+        else:
+            commit(staged, str(path))
+    except OSError as e:
+        for other in also_discard:
+            if other is not None:
+                discard_staged_json(other)
+        raise ClaudeSettingsError(f"Could not {'remove' if staged is None else 'write'} {path}: {e}") from e
+
+
+def merge_claude_settings(
+    settings: Mapping[str, JsonValue],
+    base_url: str,
+    credential: ClaudeCredential,
+    default_model: str | None = None,
+    tier_model: str | None = None,
+) -> Mapping[str, JsonValue]:
+    """Return a new settings mapping wired to route Claude Code through the proxy.
+
+    A StaticToken lands in env.ANTHROPIC_AUTH_TOKEN, an ApiKeyHelper in the top-level apiKeyHelper;
+    the other credential slots are removed either way, since Claude Code given two credentials may
+    send the wrong one. ENABLE_TOOL_SEARCH and CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY get their
+    defaults only when missing. `default_model` is the top-level `model`, the row Claude Code starts
+    on; `tier_model` is `lite autoroute up`'s knob that points every ANTHROPIC_DEFAULT_*_MODEL at one
+    group. Apart from those tier keys, exactly OWNED_PATHS are touched.
     """
     raw_env: Final = settings.get(ENV_KEY, {})
-    base_env: Final = raw_env if isinstance(raw_env, dict) else {}
-    env: Final = {
-        ENABLE_TOOL_SEARCH_KEY: ENABLE_TOOL_SEARCH_VALUE,
-        ENABLE_GATEWAY_MODEL_DISCOVERY_KEY: ENABLE_GATEWAY_MODEL_DISCOVERY_VALUE,
-        **{key: value for key, value in base_env.items() if key != ANTHROPIC_API_KEY_KEY},
-        ANTHROPIC_BASE_URL_KEY: base_url.rstrip("/"),
-    }
-    return {**settings, ENV_KEY: env, API_KEY_HELPER_KEY: api_key_helper}
+    current_env: Final = raw_env if isinstance(raw_env, dict) else {}
+    env: Final = dict(  # mutable-ok: JSON document handed to json.dump, which rejects a read-only mapping
+        chain(
+            (
+                (ENABLE_TOOL_SEARCH_KEY, ENABLE_TOOL_SEARCH_VALUE),
+                (ENABLE_GATEWAY_MODEL_DISCOVERY_KEY, ENABLE_GATEWAY_MODEL_DISCOVERY_VALUE),
+            ),
+            ((key, value) for key, value in current_env.items() if key not in _CREDENTIAL_ENV_KEYS),
+            ((ANTHROPIC_BASE_URL_KEY, base_url.rstrip("/")),),
+            ((ANTHROPIC_AUTH_TOKEN_KEY, credential.token),) if isinstance(credential, StaticToken) else (),
+            ((key, tier_model) for key in ANTHROPIC_DEFAULT_MODEL_ENV_KEYS if tier_model is not None),
+        )
+    )
+    return dict(  # mutable-ok: JSON document handed to json.dump, which rejects a read-only mapping
+        chain(
+            ((key, value) for key, value in settings.items() if key not in (API_KEY_HELPER_KEY, ENV_KEY)),
+            ((ENV_KEY, env),),
+            ((API_KEY_HELPER_KEY, credential.command),) if isinstance(credential, ApiKeyHelper) else (),
+            ((MODEL_KEY, default_model),) if default_model is not None else (),
+        )
+    )
 
 
 def resolve_api_key_helper(base_url: str, platform: str = sys.platform) -> str:
@@ -121,56 +353,273 @@ def resolve_api_key_helper(base_url: str, platform: str = sys.platform) -> str:
     return " ".join(quote(token) for token in (lite_path, "--base-url", base_url, "auth", "print-token"))
 
 
-def write_claude_settings(base_url: str, settings_path: Path, owners: Sequence[SettingsFileOwner]) -> None:
-    """Persistently point Claude Code at base_url, preserving every unrelated setting.
+def lite_api_key_helper_configured(base_url: str, settings_path: Path) -> bool:
+    """Whether settings_path already carries the apiKeyHelper `lite login --config-claude` writes for base_url.
 
-    Refuses while any owner holds a backup: each restores its backup when it
-    stops, which would silently undo this write.
+    Only an exact match counts: a helper for another proxy, a hand-written one, or
+    settings that cannot be read leave the caller on the env-token path.
     """
-    for owner in owners:
-        if owner.backup_path.exists():
-            raise ClaudeSettingsError(
-                f"`{owner.start_command}` is currently managing {settings_path} (backup at "
-                f"{owner.backup_path}) and will restore it when it stops. "
-                f"Run `{owner.stop_command}` first, then retry."
-            )
-    normalized_base_url: Final = base_url.rstrip("/")
-    api_key_helper: Final = resolve_api_key_helper(normalized_base_url)
-    existing: Final = load_json_or_empty(settings_path)
-    raw_env: Final = existing.get(ENV_KEY)
-    if raw_env is not None and not isinstance(raw_env, dict):
-        raise ClaudeSettingsError(
-            f'{settings_path} has a non-object "{ENV_KEY}" value, which this would discard. '
-            "Fix or remove it, then retry."
-        )
-    merged: Final = merge_claude_settings(existing, normalized_base_url, api_key_helper)
-    # os.replace() swaps the symlink itself for a regular file, silently detaching a
-    # settings.json that is symlinked into a dotfiles repo. There is no backup to undo
-    # that here, unlike `lite up`, so write through to the link's target instead.
-    target: Final = settings_path.resolve() if settings_path.is_symlink() else settings_path
     try:
-        write_private_json(str(target), merged)
+        configured_helper: Final = load_json_or_empty(settings_path).get(API_KEY_HELPER_KEY)
+        return configured_helper == resolve_api_key_helper(base_url.rstrip("/"))
+    except ClaudeSettingsError:
+        return False
+
+
+def _owned(container: Mapping[str, JsonValue], key: str) -> OwnedValue:
+    return OwnedValue(present=key in container, value=container.get(key))
+
+
+def _fingerprint(owned: OwnedValue) -> str:
+    return hashlib.sha256(json.dumps(owned.model_dump(mode="json"), sort_keys=True).encode()).hexdigest()
+
+
+def _env(settings: Mapping[str, JsonValue]) -> Mapping[str, JsonValue]:
+    raw_env: Final = settings.get(ENV_KEY)
+    return raw_env if isinstance(raw_env, dict) else MappingProxyType({})
+
+
+def _lookup(settings: Mapping[str, JsonValue], path: str) -> OwnedValue:
+    section, _, key = path.rpartition(".")
+    return _owned(_env(settings) if section else settings, key)
+
+
+def _with_key(container: Mapping[str, JsonValue], key: str, owned: OwnedValue) -> Mapping[str, JsonValue]:
+    return dict(  # mutable-ok: JSON document handed to json.dump, which rejects a read-only mapping
+        chain(((k, v) for k, v in container.items() if k != key), ((key, owned.value),) if owned.present else ())
+    )
+
+
+def _with(settings: Mapping[str, JsonValue], path: str, owned: OwnedValue) -> Mapping[str, JsonValue]:
+    """`settings` with the key at `path` set (or removed when `owned` is absent); nothing else changes."""
+    section, _, key = path.rpartition(".")
+    if not section:
+        return _with_key(settings, key, owned)
+    return _with_key(settings, section, OwnedValue(present=True, value=_with_key(_env(settings), key, owned)))
+
+
+def _with_all(settings: Mapping[str, JsonValue], updates: Mapping[str, OwnedValue]) -> Mapping[str, JsonValue]:
+    return reduce(lambda acc, item: _with(acc, *item), updates.items(), settings)
+
+
+def _ours(settings: Mapping[str, JsonValue], path: str, receipt: ConfigureReceipt) -> bool:
+    """Whether the key still holds what a configure wrote (a key no configure ever changed is never ours)."""
+    return receipt.written.get(path) == _fingerprint(_lookup(settings, path))
+
+
+def _claim(
+    path: str,
+    current: Mapping[str, JsonValue],
+    merged: Mapping[str, JsonValue],
+    earlier: ConfigureReceipt | None,
+    url_now: OwnedValue,
+) -> _Claim:
+    """What this configure records for one key; see ConfigureReceipt for the rules."""
+    before, after = _lookup(current, path), _lookup(merged, path)
+    carried: Final = earlier if earlier is not None and _ours(current, path, earlier) else None
+    return _Claim(
+        previous=before if carried is None else carried.previous.get(path, before),
+        written=_fingerprint(after) if before != after else (None if earlier is None else earlier.written.get(path)),
+        endpoint=None
+        if path not in _CREDENTIAL_PATHS
+        else (url_now if carried is None else carried.endpoints.get(path, url_now)),
+    )
+
+
+def _receipt(
+    current: Mapping[str, JsonValue],
+    merged: Mapping[str, JsonValue],
+    earlier: ConfigureReceipt | None,
+    file_exists: bool,
+) -> ConfigureReceipt:
+    url_now: Final = _lookup(current, _BASE_URL_PATH)
+    claims: Final = MappingProxyType({path: _claim(path, current, merged, earlier, url_now) for path in OWNED_PATHS})
+    return ConfigureReceipt(
+        file_existed=file_exists if earlier is None else earlier.file_existed,
+        env_present=ENV_KEY in current if earlier is None else earlier.env_present,
+        env_was_object=isinstance(current.get(ENV_KEY), dict) if earlier is None else earlier.env_was_object,
+        previous=MappingProxyType({path: claim.previous for path, claim in claims.items()}),
+        written=MappingProxyType({path: claim.written for path, claim in claims.items() if claim.written is not None}),
+        endpoints=MappingProxyType(
+            {path: claim.endpoint for path, claim in claims.items() if claim.endpoint is not None}
+        ),
+    )
+
+
+def read_configure_receipt(state_path: Path) -> ConfigureReceipt | None:
+    if not state_path.exists():
+        return None
+    try:
+        return ConfigureReceipt.model_validate_json(state_path.read_bytes())
+    except (OSError, ValidationError) as e:
+        raise ClaudeSettingsError(
+            f"{state_path} is not a readable `lite configure claude` receipt ({e}). "
+            "Remove it and edit Claude Code's settings by hand if they still point at the proxy."
+        ) from e
+
+
+def configure_claude_settings(
+    base_url: str,
+    credential: ClaudeCredential,
+    model: ModelChoice,
+    settings_path: Path,
+    state_path: Path,
+    owners: Sequence[SettingsFileOwner],
+    commit: Callable[[str, str], None] = commit_staged_json,
+) -> None:
+    """Persistently route Claude Code through base_url, recording how to undo it.
+
+    Both files are staged before either is committed, so a full disk or a read-only directory fails
+    before anything changes. The two commits are still two renames: a receipt rename that fails
+    discards the staged settings, and a settings rename that fails after the receipt landed puts the
+    earlier receipt back (or removes the new one), so the receipt on disk never describes settings
+    that were not written. `model`: StartOn pins the starting model, UnpinModel lets go of a pin an
+    earlier configure made (never of the user's own), KeepModel leaves it alone (a re-login).
+    """
+    refuse_while_owned(settings_path, owners)
+    current: Final = load_json_or_empty(settings_path)
+    _env_object(current, settings_path)
+    earlier: Final = read_configure_receipt(state_path)
+    existing: Final = (
+        _with(current, MODEL_KEY, earlier.previous[MODEL_KEY])
+        if isinstance(model, UnpinModel) and earlier is not None and _ours(current, MODEL_KEY, earlier)
+        else current
+    )
+    merged: Final = merge_claude_settings(
+        existing, base_url, credential, model.model if isinstance(model, StartOn) else None
+    )
+    receipt: Final = _receipt(current, merged, earlier, settings_path.exists())
+    target: Final = _write_target(settings_path)
+    try:
+        ensure_private_dir(state_path.parent)
     except OSError as e:
-        raise ClaudeSettingsError(f"Could not write {target}: {e}") from e
+        raise ClaudeSettingsError(f"Could not write {state_path}: {e}") from e
+    staged_receipt: Final = _stage(state_path, receipt.model_dump(mode="json"))
+    try:
+        staged_settings: Final = _stage(target, merged)
+    except ClaudeSettingsError:
+        discard_staged_json(staged_receipt)
+        raise
+    _land(state_path, staged_receipt, (staged_settings,), commit)
+    try:
+        _land(target, staged_settings, commit=commit)
+    except ClaudeSettingsError as settings_error:
+        try:
+            _land(state_path, None if earlier is None else _stage(state_path, earlier.model_dump(mode="json")))
+        except ClaudeSettingsError as receipt_error:
+            raise ClaudeSettingsError(
+                f"{settings_error} The receipt at {state_path} now describes settings that were not written and "
+                f"could not be put back either ({receipt_error}); remove it before retrying."
+            ) from settings_error
+        raise
+
+
+def _endpoint_text(endpoint: OwnedValue) -> str:
+    if not endpoint.present:
+        return f"no {ANTHROPIC_BASE_URL_KEY} (Anthropic's default endpoint)"
+    return endpoint.value if isinstance(endpoint.value, str) else json.dumps(endpoint.value)
+
+
+def unconfigure_claude_settings(
+    settings_path: Path, state_path: Path, owners: Sequence[SettingsFileOwner]
+) -> UnconfigureOutcome:
+    """Undo `lite configure claude`: put back every key still holding what configure wrote, leave the
+    rest alone, and withhold a credential the restored file would send to a different server than it
+    was issued for (the receipt stays, owning only those slots, so a later unconfigure can finish)."""
+    refuse_while_owned(settings_path, owners)
+    receipt: Final = read_configure_receipt(state_path)
+    if receipt is None:
+        raise ClaudeSettingsError(
+            f"Claude Code is not configured by `lite configure claude` (no receipt at {state_path}); nothing to undo."
+        )
+    current: Final = load_json_or_empty(settings_path)
+    _env_object(current, settings_path)
+    ours: Final = tuple(path for path in receipt.written if _ours(current, path, receipt))
+    kept: Final = tuple(path for path in receipt.written if path not in ours and _lookup(current, path).present)
+    put_back: Final = _with_all(current, MappingProxyType({path: receipt.previous[path] for path in ours}))
+    url_after: Final = _lookup(put_back, _BASE_URL_PATH)
+    withheld: Final = tuple(
+        WithheldCredential(path, _endpoint_text(receipt.endpoints[path]))
+        for path in _CREDENTIAL_PATHS
+        if path in ours and receipt.previous[path].present and receipt.endpoints[path] != url_after
+    )
+    absent: Final = OwnedValue(present=False)
+    trimmed: Final = _with_all(put_back, MappingProxyType({item.key: absent for item in withheld}))
+    settings: Final = (
+        trimmed
+        if _env(trimmed) or receipt.env_was_object
+        else _with_key(trimmed, ENV_KEY, OwnedValue(present=receipt.env_present, value=None))
+    )
+    target: Final = _write_target(settings_path)
+    file_removed: Final = not settings and not (receipt.file_existed and target.exists())
+    kept_receipt: Final = (  # mutable-ok: pydantic serializes the update as given and rejects a mappingproxy
+        receipt.model_copy(update={"written": {item.key: _fingerprint(absent) for item in withheld}})
+        if withheld
+        else None
+    )
+    staged_settings: Final = None if file_removed else _stage(target, settings)
+    try:
+        staged_receipt: Final = (
+            None if kept_receipt is None else _stage(state_path, kept_receipt.model_dump(mode="json"))
+        )
+    except ClaudeSettingsError:
+        if staged_settings is not None:
+            discard_staged_json(staged_settings)
+        raise
+    _land(target, staged_settings, (staged_receipt,))
+    _land(state_path, staged_receipt)
+    return UnconfigureOutcome(
+        restored=tuple(path for path in ours if _lookup(current, path) != _lookup(settings, path)),
+        kept=kept,
+        withheld=withheld,
+        file_removed=file_removed,
+    )
 
 
 __all__ = (
     "ANTHROPIC_API_KEY_KEY",
+    "ANTHROPIC_AUTH_TOKEN_KEY",
     "ANTHROPIC_BASE_URL_KEY",
+    "ANTHROPIC_DEFAULT_MODEL_ENV_KEYS",
     "API_KEY_HELPER_KEY",
     "AUTOROUTE_BACKUP_PATH",
     "BACKUP_PATH",
+    "CLAUDE_CONFIG_DIR_ENV",
     "CLAUDE_SETTINGS_PATH",
+    "CONFIGURE_STATE_PATH",
     "ENABLE_GATEWAY_MODEL_DISCOVERY_KEY",
     "ENABLE_GATEWAY_MODEL_DISCOVERY_VALUE",
     "ENABLE_TOOL_SEARCH_KEY",
     "ENABLE_TOOL_SEARCH_VALUE",
     "ENV_KEY",
+    "MODEL_KEY",
+    "OWNED_ENV_KEYS",
+    "OWNED_PATHS",
+    "OWNED_TOP_LEVEL_KEYS",
     "SETTINGS_FILE_OWNERS",
+    "STARTING_MODEL_ROLE",
+    "ApiKeyHelper",
+    "ClaudeCredential",
     "ClaudeSettingsError",
+    "ConfigureReceipt",
+    "KeepModel",
+    "ModelChoice",
+    "OwnedValue",
     "SettingsFileOwner",
+    "StartOn",
+    "StaticToken",
+    "UnconfigureOutcome",
+    "UnpinModel",
+    "WithheldCredential",
+    "claude_settings_path",
+    "configure_claude_settings",
+    "configure_state_path",
+    "lite_api_key_helper_configured",
     "load_json_or_empty",
     "merge_claude_settings",
+    "read_configure_receipt",
+    "refuse_while_owned",
     "resolve_api_key_helper",
-    "write_claude_settings",
+    "settings_file_owners",
+    "unconfigure_claude_settings",
 )
diff --git a/litellm/proxy/client/cli/commands/configure.py b/litellm/proxy/client/cli/commands/configure.py
new file mode 100644
index 00000000000..9d329f8d8f2
--- /dev/null
+++ b/litellm/proxy/client/cli/commands/configure.py
@@ -0,0 +1,292 @@
+"""`lite configure claude` and `lite unconfigure claude`: persistent Claude Code wiring, undoable."""
+
+import os
+import sys
+from collections.abc import Callable, Sequence
+from dataclasses import dataclass
+from pathlib import Path
+from types import MappingProxyType
+from typing import Final
+
+import click
+from InquirerPy import inquirer
+from InquirerPy.base.control import Choice
+
+from litellm.proxy.common_utils.model_listing_utils import (
+    CLAUDE_CODE_CLIENT,
+    CLAUDE_CODE_PICKER_PATTERN,
+    GATEWAY_CLIENT_HEADER,
+)
+
+from .auth import CliContextObj, context_secret_vault, get_stored_api_key
+from .claude_settings import (
+    STARTING_MODEL_ROLE,
+    ApiKeyHelper,
+    ClaudeCredential,
+    ClaudeSettingsError,
+    ModelChoice,
+    StartOn,
+    StaticToken,
+    UnconfigureOutcome,
+    UnpinModel,
+    claude_settings_path,
+    configure_claude_settings,
+    configure_state_path,
+    refuse_while_owned,
+    resolve_api_key_helper,
+    settings_file_owners,
+    unconfigure_claude_settings,
+)
+from .pi import ListedModel, ListingFailure, PiSyncError, fetch_model_listing
+from .up import ensure_fresh_login
+
+_LISTED_MODELS_SHOWN: Final = 20
+_CLAUDE_TARGET: Final = "claude"
+_TARGETS: Final = ((_CLAUDE_TARGET, "Claude Code (CLI)"),)
+_KEEP_DEFAULT_MODEL: Final = "Keep Claude Code's own default"
+_CLAUDE_CODE_VIEW: Final = MappingProxyType(
+    {"anthropic-version": "2023-06-01", GATEWAY_CLIENT_HEADER: CLAUDE_CODE_CLIENT}
+)
+_MODEL_OPTION_HELP: Final = (
+    f"Proxy model to set as {STARTING_MODEL_ROLE}. Must be listed on /v1/models for the key; without it, "
+    "Claude Code keeps its own default and a pin an earlier configure made is let go of. Nothing pins Claude "
+    "Code's sub-agent or background tiers; `lite autoroute up` is the mode that does."
+)
+
+
+def resolve_credential(ctx: click.Context, api_key: str | None) -> tuple[ClaudeCredential, str]:
+    """The credential to write and the key to check the proxy with.
+
+    An explicit key (--api-key, `lite --api-key`, LITELLM_PROXY_API_KEY) is long-lived and goes
+    into settings.json as a static token. Without one, the stored `lite login` credential is used
+    the way `lite login --config-claude` uses it, through apiKeyHelper, since it expires within a
+    day and renews in place there; a missing or stale login is refreshed first, as `lite up` does.
+    """
+    ctx_obj: Final[CliContextObj] = ctx.obj
+    explicit: Final = api_key or (None if ctx_obj.get("api_key_from_token_file") else ctx_obj.get("api_key"))
+    if explicit:
+        return StaticToken(explicit), explicit
+    base_url: Final = ctx_obj["base_url"]
+    ensure_fresh_login(ctx)
+    stored: Final = get_stored_api_key(expected_base_url=base_url, vault=context_secret_vault(ctx))
+    if not stored:
+        raise ClaudeSettingsError("Login did not produce a usable token.")
+    return ApiKeyHelper(resolve_api_key_helper(base_url)), stored
+
+
+@dataclass(frozen=True, slots=True)
+class _Listing:
+    models: tuple[ListedModel, ...]
+
+    @property
+    def ids(self) -> tuple[str, ...]:
+        return tuple(model.id for model in self.models)
+
+
+def _start(ctx: click.Context, api_key: str | None) -> tuple[ClaudeCredential, _Listing]:
+    """Every configure path begins the same way: the local ownership check first, so a `lite up`
+    session is refused before any login prompt or request, then the credential, then the listing."""
+    settings_path: Final = claude_settings_path(os.environ)
+    try:
+        refuse_while_owned(settings_path, settings_file_owners(settings_path))
+        credential, key = resolve_credential(ctx, api_key)
+    except ClaudeSettingsError as e:
+        raise click.ClickException(str(e))
+    return credential, _listed_models(ctx.obj["base_url"], key)
+
+
+def _listing_error(base_url: str, error: PiSyncError) -> str:
+    """The hint that fits how the listing failed: only an unreachable proxy gets the "is it running" question."""
+    if error.kind is ListingFailure.REJECTED:
+        return f"LiteLLM rejected your key (HTTP {error.status}). Run `lite login` to refresh it, or pass a valid --api-key."
+    if error.kind is ListingFailure.UNREACHABLE:
+        return f"{error.message} Is the proxy at {base_url} running, and is --base-url (or LITELLM_PROXY_URL) correct?"
+    if error.kind is ListingFailure.EMPTY:
+        return f"{error.message} Claude Code would have nothing to run; give the key access to at least one model."
+    return f"{error.message} The proxy at {base_url} answered, so check that it is a LiteLLM proxy and is healthy."
+
+
+def _listed_models(base_url: str, key: str) -> _Listing:
+    listed: Final = fetch_model_listing(base_url, key, headers=_CLAUDE_CODE_VIEW)
+    if isinstance(listed, PiSyncError):
+        raise click.ClickException(_listing_error(base_url, listed))
+    return _Listing(listed)
+
+
+def _starting_model(model: str, listing: _Listing) -> str | None:
+    source: Final = next((listed.id for listed in listing.models if listed.source_model == model), None)
+    return source or next((listed.id for listed in listing.models if listed.id == model), None)
+
+
+def _model_choice(model: str | None) -> ModelChoice:
+    return StartOn(model) if model is not None else UnpinModel()
+
+
+def _apply_claude(ctx: click.Context, credential: ClaudeCredential, listing: _Listing, model: str | None) -> None:
+    ctx_obj: Final[CliContextObj] = ctx.obj
+    base_url: Final = ctx_obj["base_url"]
+    listed: Final = listing.ids
+    starting: Final = _starting_model(model, listing) if model is not None else None
+    if model is not None and starting is None:
+        shown: Final = ", ".join(listed[:_LISTED_MODELS_SHOWN])
+        more: Final = f", and {len(listed) - _LISTED_MODELS_SHOWN} more" if len(listed) > _LISTED_MODELS_SHOWN else ""
+        raise click.ClickException(
+            f"{model!r} is not served by {base_url} for this key. /v1/models lists: {shown}{more}."
+        )
+    settings_path: Final = claude_settings_path(os.environ)
+    try:
+        configure_claude_settings(
+            base_url,
+            credential,
+            _model_choice(starting),
+            settings_path,
+            configure_state_path(settings_path),
+            settings_file_owners(settings_path),
+        )
+    except ClaudeSettingsError as e:
+        raise click.ClickException(str(e))
+    in_picker: Final = sum(1 for listed_model in listed if CLAUDE_CODE_PICKER_PATTERN.search(listed_model))
+    click.echo(f"Configured Claude Code: {settings_path} now routes through {base_url}.")
+
+    click.echo(
+        "Credential: your virtual key, stored in the file as ANTHROPIC_AUTH_TOKEN."
+        if isinstance(credential, StaticToken)
+        else "Credential: your `lite login`, read through apiKeyHelper on every request, so a later login renews it."
+    )
+    click.echo(
+        f"Starting model: {starting} ({STARTING_MODEL_ROLE}); switch any time with /model."
+        if starting is not None
+        else "Starting model: not pinned (Claude Code's default, or a model you set yourself); switch with /model, or "
+        "pass --model to start on a proxy model."
+    )
+    click.echo(
+        f"/model will list all {len(listed)} of the proxy's models."
+        if in_picker == len(listed)
+        else f"/model will list {in_picker} of the proxy's {len(listed)} models: Claude Code shows only ids containing "
+        "'claude' or 'anthropic', and this proxy does not list the rest under such names."
+    )
+    click.echo("Start `claude` from any terminal. Undo with `lite unconfigure claude`.")
+    if isinstance(credential, StaticToken) and settings_path.is_symlink():
+        click.echo(
+            f"Note: {settings_path} is a symlink to {settings_path.resolve()}, so your key now lives in "
+            "that file; keep it out of version control.",
+            err=True,
+        )
+
+
+def _pick_targets() -> tuple[str, ...]:
+    picked: Final = inquirer.checkbox(
+        message="Which agents should route through LiteLLM?",
+        choices=[Choice(value, name=label, enabled=True) for value, label in _TARGETS],
+        validate=lambda chosen: len(chosen) > 0,
+        invalid_message="Pick at least one.",
+    ).execute()
+    return tuple(str(value) for value in picked)
+
+
+def _pick_model(listed: Sequence[str]) -> str | None:
+    picked: Final = inquirer.fuzzy(
+        message="Model Claude Code starts on (type to filter; /model switches any time):",
+        choices=[_KEEP_DEFAULT_MODEL, *listed],
+    ).execute()
+    return None if picked == _KEEP_DEFAULT_MODEL else str(picked)
+
+
+def interactive_configure(
+    ctx: click.Context,
+    pick_targets: Callable[[], tuple[str, ...]] = _pick_targets,
+    pick_model: Callable[[Sequence[str]], str | None] = _pick_model,
+) -> None:
+    """`lite configure` with no agent named: ask which agents to wire and which model to pin."""
+    targets: Final = pick_targets()
+    if _CLAUDE_TARGET not in targets:
+        return
+    credential, listing = _start(ctx, None)
+    _apply_claude(
+        ctx, credential, listing, pick_model(tuple(model.source_model or model.id for model in listing.models))
+    )
+
+
+@click.group(name="configure", invoke_without_command=True)
+@click.pass_context
+def configure_group(ctx: click.Context) -> None:
+    """Persistently route a coding agent through your LiteLLM proxy.
+
+    With no agent named, asks which agents to wire and which proxy model to pin.
+    """
+    if ctx.invoked_subcommand is not None:
+        return
+    if not sys.stdin.isatty():
+        raise click.ClickException(
+            "`lite configure` asks questions, so it needs a terminal. Non-interactively, run "
+            "`lite configure claude --api-key <key> --model <model>`."
+        )
+    interactive_configure(ctx)
+
+
+@click.group(name="unconfigure")
+def unconfigure_group() -> None:
+    """Undo `lite configure` for a coding agent."""
+
+
+@configure_group.command(name="claude")
+@click.option(
+    "--api-key",
+    "api_key",
+    default=None,
+    help="Long-lived LiteLLM virtual key written into Claude Code's settings. Defaults to the `lite --api-key` / "
+    "LITELLM_PROXY_API_KEY value; with neither, your `lite login` credential is used through apiKeyHelper.",
+)
+@click.option("--model", default=None, help=_MODEL_OPTION_HELP)
+@click.pass_context
+def configure_claude(ctx: click.Context, api_key: str | None, model: str | None) -> None:
+    """Route every Claude Code session through your LiteLLM proxy until `lite unconfigure claude`.
+
+    Patches ~/.claude/settings.json in place: the proxy URL, your credential (a virtual key as a
+    static token, or your `lite login` through apiKeyHelper), and gateway model discovery so
+    /model lists the proxy's models; --model picks the one Claude Code starts on. Every other
+    setting is kept, and what changed is recorded so `lite unconfigure claude` can put it back.
+    Assumes the proxy is already running.
+    """
+    credential, listing = _start(ctx, api_key)
+    _apply_claude(ctx, credential, listing, model)
+
+
+@unconfigure_group.command(name="claude")
+def unconfigure_claude() -> None:
+    """Return Claude Code's settings to what they were before `lite configure claude`.
+
+    Also undoes `lite login --config-claude`. Only keys still holding what configure wrote are
+    put back; anything you changed since is left as it is and named in the output.
+    """
+    settings_path: Final = claude_settings_path(os.environ)
+    state_path: Final = configure_state_path(settings_path)
+    try:
+        outcome: Final = unconfigure_claude_settings(settings_path, state_path, settings_file_owners(settings_path))
+    except ClaudeSettingsError as e:
+        raise click.ClickException(str(e))
+    _report_unconfigure(settings_path, state_path, outcome)
+
+
+def _report_unconfigure(settings_path: Path, state_path: Path, outcome: UnconfigureOutcome) -> None:
+    """Say what unconfigure did, naming only keys whose value it changed."""
+    if outcome.file_removed:
+        click.echo(
+            f"No settings file remains at {settings_path}; it held nothing but `lite configure claude`'s own keys."
+        )
+    elif outcome.restored:
+        click.echo(f"Restored in {settings_path}: {', '.join(outcome.restored)}.")
+    else:
+        click.echo(f"Nothing in {settings_path} was still ours to restore.")
+    if outcome.kept:
+        click.echo(f"Left as you changed them since: {', '.join(outcome.kept)}.")
+    if outcome.withheld:
+        click.echo(
+            "Left removed, since the file now points at a different server than they were issued for: "
+            + "; ".join(f"{item.key} (captured with {item.endpoint})" for item in outcome.withheld)
+            + f". They stay in {state_path}: point env.ANTHROPIC_BASE_URL back and run `lite unconfigure claude` "
+            "again to put them back, or delete that file to drop them."
+        )
+
+
+__all__ = ("configure_group", "interactive_configure", "resolve_credential", "unconfigure_group")
diff --git a/litellm/proxy/client/cli/commands/pi.py b/litellm/proxy/client/cli/commands/pi.py
index 7b0c1970c4e..9810e81ae36 100644
--- a/litellm/proxy/client/cli/commands/pi.py
+++ b/litellm/proxy/client/cli/commands/pi.py
@@ -10,21 +10,40 @@ import os
 import tempfile
 from collections.abc import Callable, Mapping
 from dataclasses import dataclass
+from enum import StrEnum
 from pathlib import Path
 from types import MappingProxyType
-from typing import Final
+from typing import Annotated, Final
 
 import requests
-from pydantic import BaseModel, JsonValue, TypeAdapter, ValidationError
+from pydantic import BaseModel, ConfigDict, JsonValue, TypeAdapter, ValidationError, model_validator
+from pydantic.types import StringConstraints
 
 PI_CONFIG_DIR_ENV: Final = "PI_CODING_AGENT_DIR"
 PI_PROVIDER_NAME: Final = "litellm"
 LITELLM_PROXY_API_KEY_ENV: Final = "LITELLM_PROXY_API_KEY"
+_REJECTED_STATUSES: Final = frozenset((401, 403))
+
+
+class ListingFailure(StrEnum):
+    """Why a proxy could not be listed, decided once where the HTTP outcome is classified.
+
+    `unreachable` means no response at all; the other kinds prove the proxy answered, so callers
+    must not suggest checking whether it is running.
+    """
+
+    UNREACHABLE = "unreachable"
+    REJECTED = "rejected"
+    BAD_BODY = "bad_body"
+    EMPTY = "empty"
+    OTHER = "other"
 
 
 @dataclass(frozen=True, slots=True)
 class PiSyncError:
     message: str
+    status: int | None = None
+    kind: ListingFailure | None = None
 
 
 @dataclass(frozen=True, slots=True)
@@ -33,12 +52,25 @@ class ModelLimits:
     max_tokens: int | None
 
 
-class _Model(BaseModel):
-    id: str
+_NonEmptyString = Annotated[str, StringConstraints(min_length=1)]
+
+
+class ListedModel(BaseModel):
+    model_config = ConfigDict(frozen=True)
+
+    id: _NonEmptyString
+    source_model: _NonEmptyString | None = None
 
 
 class _ModelList(BaseModel):
-    data: tuple[_Model, ...]
+    data: tuple[ListedModel, ...]
+
+    @model_validator(mode="after")
+    def unique_id_mappings(self) -> "_ModelList":
+        mappings: Final = frozenset((model.id, model.source_model or model.id) for model in self.data)
+        if len(frozenset(model.id for model in self.data)) != len(mappings):
+            raise ValueError("model ids must not map to multiple source models")
+        return self
 
 
 class _ModelGroup(BaseModel):
@@ -51,31 +83,47 @@ class _ModelGroupList(BaseModel):
     data: tuple[_ModelGroup, ...]
 
 
+def fetch_model_listing(
+    base_url: str,
+    api_key: str,
+    *,
+    get: Callable[..., requests.Response] = requests.get,
+    headers: Mapping[str, str] = MappingProxyType({}),
+) -> tuple[ListedModel, ...] | PiSyncError:
+    url: Final = base_url.rstrip("/") + "/v1/models"
+    try:
+        resp: Final = get(
+            url,
+            headers={"Authorization": f"Bearer {api_key}", **headers},  # mutable-ok: requests headers require a dict
+            timeout=10,
+        )
+    except requests.RequestException as e:
+        return PiSyncError(f"Could not list models from the proxy: {e}", kind=ListingFailure.UNREACHABLE)
+    if resp.status_code != 200:
+        return PiSyncError(
+            f"The proxy returned HTTP {resp.status_code} for /v1/models; cannot list models.",
+            resp.status_code,
+            ListingFailure.REJECTED if resp.status_code in _REJECTED_STATUSES else ListingFailure.OTHER,
+        )
+    try:
+        listing: Final = _ModelList.model_validate(resp.json())
+    except (ValueError, ValidationError) as e:
+        return PiSyncError(f"Unexpected /v1/models response from the proxy: {e}", kind=ListingFailure.BAD_BODY)
+    models: Final = tuple(dict.fromkeys(listing.data))
+    if not models:
+        return PiSyncError("The proxy returned no models for your key.", kind=ListingFailure.EMPTY)
+    return models
+
+
 def fetch_model_ids(
     base_url: str,
     api_key: str,
     *,
     get: Callable[..., requests.Response] = requests.get,
+    headers: Mapping[str, str] = MappingProxyType({}),
 ) -> tuple[str, ...] | PiSyncError:
-    url: Final = base_url.rstrip("/") + "/v1/models"
-    try:
-        resp: Final = get(
-            url,
-            headers={"Authorization": f"Bearer {api_key}"},  # mutable-ok: requests headers require a dict
-            timeout=10,
-        )
-    except requests.RequestException as e:
-        return PiSyncError(f"Could not list models from the proxy: {e}")
-    if resp.status_code != 200:
-        return PiSyncError(f"The proxy returned HTTP {resp.status_code} for /v1/models; cannot build pi's model list.")
-    try:
-        listing: Final = _ModelList.model_validate(resp.json())
-    except (ValueError, ValidationError) as e:
-        return PiSyncError(f"Unexpected /v1/models response from the proxy: {e}")
-    ids: Final = tuple(dict.fromkeys(model.id for model in listing.data))
-    if not ids:
-        return PiSyncError("The proxy returned no models for your key, so pi would have nothing to run.")
-    return ids
+    listed: Final = fetch_model_listing(base_url, api_key, get=get, headers=headers)
+    return listed if isinstance(listed, PiSyncError) else tuple(dict.fromkeys(model.id for model in listed))
 
 
 _NO_LIMITS: Final[Mapping[str, ModelLimits]] = MappingProxyType({})
@@ -200,10 +248,13 @@ __all__ = (
     "LITELLM_PROXY_API_KEY_ENV",
     "PI_CONFIG_DIR_ENV",
     "PI_PROVIDER_NAME",
+    "ListedModel",
+    "ListingFailure",
     "ModelLimits",
     "PiSyncError",
     "fetch_model_ids",
     "fetch_model_limits",
+    "fetch_model_listing",
     "models_json_path",
     "provider_block",
     "sync_models_json",
diff --git a/litellm/proxy/client/cli/commands/up.py b/litellm/proxy/client/cli/commands/up.py
index b7c02866d6f..ffece87ab83 100644
--- a/litellm/proxy/client/cli/commands/up.py
+++ b/litellm/proxy/client/cli/commands/up.py
@@ -23,6 +23,7 @@ from .auth import CliContextObj, context_secret_vault, get_stored_api_key, load_
 from .claude_settings import (
     BACKUP_PATH,
     CLAUDE_SETTINGS_PATH,
+    ApiKeyHelper,
     ClaudeSettingsError,
     load_json_or_empty,
     merge_claude_settings,
@@ -123,7 +124,7 @@ def _stored_login_is_pkce(vault: SecretVault) -> bool:
     return token_data is not None and token_data.get("refresh_token") is not None
 
 
-def _ensure_fresh_login(ctx: click.Context) -> None:
+def ensure_fresh_login(ctx: click.Context) -> None:
     ctx_obj: Final[CliContextObj] = ctx.obj
     base_url: Final = ctx_obj["base_url"].rstrip("/")
     vault: Final = context_secret_vault(ctx)
@@ -141,7 +142,7 @@ def _ensure_fresh_login(ctx: click.Context) -> None:
     click.echo("No fresh LiteLLM login found for this proxy; starting login...")
     ctx.invoke(login, pkce=pkce)
     if not _usable_login(get_stored_api_key(expected_base_url=base_url, vault=vault), vault):
-        raise UpError("Login did not produce a usable token; cannot start `lite up`.")
+        raise UpError("Login did not produce a usable token.")
 
 
 def _restore_and_report() -> None:
@@ -169,7 +170,7 @@ def up(ctx: click.Context) -> None:
     base_url: Final = ctx.obj["base_url"]
 
     try:
-        _ensure_fresh_login(ctx)
+        ensure_fresh_login(ctx)
         api_key: Final = resolve_api_key(ctx)
         verify_proxy_key(base_url, api_key)
 
@@ -190,7 +191,7 @@ def up(ctx: click.Context) -> None:
         )
 
         CLAUDE_SETTINGS_PATH.parent.mkdir(exist_ok=True)
-        merged: Final = merge_claude_settings(original_settings, base_url, api_key_helper)
+        merged: Final = merge_claude_settings(original_settings, base_url, ApiKeyHelper(api_key_helper))
         with open(CLAUDE_SETTINGS_PATH, "w") as f:
             json.dump(merged, f, indent=2)
     except (AgentRunError, ClaudeSettingsError) as e:
diff --git a/litellm/proxy/client/cli/main.py b/litellm/proxy/client/cli/main.py
index eae1b0f5bc9..b0e81a222c0 100644
--- a/litellm/proxy/client/cli/main.py
+++ b/litellm/proxy/client/cli/main.py
@@ -13,6 +13,7 @@ from .commands.auth import auth_group, context_secret_vault, get_stored_api_key,
 from .commands.autoroute.commands import autoroute_group
 from .commands.chat import chat
 from .commands.config import config_commands, get_config_value, hidden_command_names
+from .commands.configure import configure_group, unconfigure_group
 from .commands.credentials import credentials
 from .commands.debug import debug
 from .commands.encryption import encryption
@@ -162,6 +163,9 @@ cli.add_command(model_groups)
 # Add the autoroute command group (QA auto-routing against your real proxy)
 cli.add_command(autoroute_group, name="autoroute")
 cli.add_command(config_commands)
+# Add configure/unconfigure (persistently wire a coding agent to the proxy with a virtual key)
+cli.add_command(configure_group)
+cli.add_command(unconfigure_group)
 
 
 if __name__ == "__main__":
diff --git a/litellm/proxy/collector.py b/litellm/proxy/collector.py
new file mode 100644
index 00000000000..3ff2a83860b
--- /dev/null
+++ b/litellm/proxy/collector.py
@@ -0,0 +1,220 @@
+"""Collector sidecar: consume spend events from the pod's inference workers and run the cost pipeline.
+
+Runs the proxy startup lifespan (config, Prisma, Redis transaction buffer, scheduled spend flushes)
+without serving HTTP, then listens on ``LITELLM_COLLECTOR_ADDRESS`` for newline-delimited spend
+events. Each event goes through the unchanged ``_ProxyDBLogger._PROXY_track_cost_callback``, so
+spend logs, spend counters, budget reservation reconciliation and cache updates happen exactly as
+they would in-process, just in this container. Events are handled in order per producer connection
+(one per uvicorn worker); a slow pipeline fills the socket buffer and the producer's bounded queue,
+which is the backpressure that triggers its fallback or drop policy. ``SIGTERM`` stops accepting
+connections, half-closes every producer connection so the producers switch to their unavailable
+policy, finishes the events already sent, then runs the proxy shutdown (which flushes the buffered
+spend transactions).
+
+``DATABASE_URL`` is assembled from the same ``DATABASE_*`` inputs as the proxy container, and when
+``LITELLM_PGBOUNCER_ENABLED`` is set it points at the PgBouncer that container already runs on the
+pod's loopback, so the sidecar must see the same env as the proxy. Under ``IAM_TOKEN_DB_AUTH`` or
+``AZURE_POSTGRESQL_AUTH`` that PgBouncer only accepts the token the proxy container minted, so the
+sidecar goes to Postgres directly and mints its own. Works from any image that has ``litellm``
+installed:
+
+    python -m litellm.proxy.collector [--address unix:///path.sock]
+"""
+
+import asyncio
+import logging
+import os
+import signal
+import sys
+from collections.abc import Awaitable, Callable, Mapping, Sequence
+from pathlib import Path
+from typing import Final
+
+from litellm._logging import verbose_logger, verbose_proxy_logger, verbose_router_logger
+from litellm.proxy.db.db_url_settings import DatabaseURLSettings
+from litellm.proxy.db.pgbouncer import (
+    PgBouncerError,
+    PgBouncerSettings,
+    export_pooled_database_url,
+    pooled_database_url,
+)
+from litellm.proxy.spend_tracking.spend_event_producer import (
+    COLLECTOR_JOB_ROLE,
+    AddressError,
+    CollectorAddress,
+    CollectorSettings,
+    TcpAddress,
+    UnixAddress,
+    parse_collector_address,
+)
+
+MAX_EVENT_BYTES: Final = 64 * 1024 * 1024
+
+
+class SpendEventConsumer:
+    """Accepts producer connections and runs ``handler`` on every line each one sends, in order."""
+
+    def __init__(self, handler: Callable[[bytes], Awaitable[None]]) -> None:
+        self._handler = handler
+        self._open_connections: set[asyncio.StreamWriter] = set()  # mutable-ok: live producer connections
+        self._idle = asyncio.Event()
+        self._idle.set()
+        self._received = 0
+        self._handled = 0
+        self._failed = 0
+
+    @property
+    def received(self) -> int:
+        return self._received
+
+    @property
+    def handled(self) -> int:
+        return self._handled
+
+    @property
+    def failed(self) -> int:
+        return self._failed
+
+    async def serve(self, address: CollectorAddress) -> asyncio.Server:
+        match address:
+            case UnixAddress(path=path):
+                socket_path: Final = Path(path)
+                socket_path.parent.mkdir(parents=True, exist_ok=True)
+                socket_path.unlink(missing_ok=True)
+                return await asyncio.start_unix_server(self._on_connection, path=path, limit=MAX_EVENT_BYTES)
+            case TcpAddress(host=host, port=port):
+                return await asyncio.start_server(self._on_connection, host=host, port=port, limit=MAX_EVENT_BYTES)
+
+    async def _on_connection(self, reader: asyncio.StreamReader, writer: asyncio.StreamWriter) -> None:
+        self._open_connections.add(writer)
+        self._idle.clear()
+        try:
+            while line := await reader.readline():
+                if not line.endswith(b"\n"):
+                    verbose_proxy_logger.error("collector: discarding truncated spend event (%d bytes)", len(line))
+                    break
+                self._received += 1
+                await self._handle(line)
+        except (ConnectionError, asyncio.IncompleteReadError, asyncio.LimitOverrunError) as error:
+            verbose_proxy_logger.warning("collector: producer connection ended abnormally: %s", error)
+        finally:
+            writer.close()
+            self._open_connections.discard(writer)
+            if not self._open_connections:
+                self._idle.set()
+
+    async def _handle(self, line: bytes) -> None:
+        try:
+            await self._handler(line)
+            self._handled += 1
+        except Exception:  # noqa: BLE001  # the cost pipeline raises anything; one bad event must not stop the sidecar
+            self._failed += 1
+            verbose_proxy_logger.exception("collector: spend event failed")
+
+    async def drain(self, timeout: float) -> int:
+        """Half-close every producer connection, then keep reading until each producer hangs up or ``timeout``.
+
+        Returns how many producer connections were still open when the timeout hit.
+        """
+        for writer in tuple(self._open_connections):
+            if writer.is_closing() or not writer.can_write_eof():
+                continue
+            try:
+                writer.write_eof()
+            except (OSError, RuntimeError) as error:
+                verbose_proxy_logger.debug("collector: producer already gone before half-close: %s", error)
+        try:
+            await asyncio.wait_for(self._idle.wait(), timeout)
+        except TimeoutError:
+            pass
+        return len(self._open_connections)
+
+
+def _install_stop_signals(loop: asyncio.AbstractEventLoop, stop: asyncio.Event) -> None:
+    for signum in (signal.SIGTERM, signal.SIGINT):
+        loop.add_signal_handler(signum, stop.set)
+
+
+async def run_collector(address: CollectorAddress, drain_timeout: float) -> None:
+    from fastapi import FastAPI
+
+    from litellm.proxy.hooks.proxy_track_cost_callback import run_spend_event
+    from litellm.proxy.proxy_server import proxy_startup_event
+
+    stop: Final = asyncio.Event()
+    _install_stop_signals(asyncio.get_running_loop(), stop)
+    consumer: Final = SpendEventConsumer(handler=run_spend_event)
+    async with proxy_startup_event(FastAPI()):
+        server: Final = await consumer.serve(address)
+        verbose_proxy_logger.info("collector: listening on %s", address)
+        await stop.wait()
+        server.close()
+        still_open: Final = await consumer.drain(drain_timeout)
+        verbose_proxy_logger.info(
+            "collector: stopping. received=%d handled=%d failed=%d connections_cut=%d",
+            consumer.received,
+            consumer.handled,
+            consumer.failed,
+            still_open,
+        )
+
+
+def address_argument(argv: Sequence[str], default: str) -> str | AddressError:
+    match tuple(argv):
+        case ():
+            return default
+        case ("--address", value):
+            return value
+        case _:
+            return AddressError(f"usage: python -m litellm.proxy.collector [--address ADDRESS], got {tuple(argv)}")
+
+
+def apply_log_level(litellm_log: str | None) -> None:
+    """Mirror the proxy's ``LITELLM_LOG`` handling: the sidecar has no CLI flags to turn logging on."""
+    level: Final = logging.getLevelNamesMapping().get((litellm_log or "").upper())
+    if level is None:
+        return
+    for logger in (verbose_logger, verbose_router_logger, verbose_proxy_logger):
+        logger.setLevel(level)
+
+
+def pod_pgbouncer_database_url(
+    pgbouncer: PgBouncerSettings, environ: Mapping[str, str], *, token_auth: bool
+) -> str | PgBouncerError | None:
+    """The proxy container's PgBouncer URL for ``environ["DATABASE_URL"]``, or None to connect to Postgres directly.
+
+    Direct is the answer when PgBouncer is off, and also under token auth: that PgBouncer's auth file
+    only holds the token its own container minted, which this container cannot present.
+    """
+    if not pgbouncer.enabled or token_auth:
+        return None
+    upstream_url: Final = environ.get("DATABASE_URL")
+    if upstream_url is None:
+        return PgBouncerError("LITELLM_PGBOUNCER_ENABLED is set but no DATABASE_URL could be assembled")
+    return pooled_database_url(upstream_url, pgbouncer)
+
+
+def main(argv: Sequence[str]) -> None:
+    os.environ.setdefault("LITELLM_JOB_ROLE", COLLECTOR_JOB_ROLE)
+    apply_log_level(os.environ.get("LITELLM_LOG"))
+    database: Final = DatabaseURLSettings.from_env()
+    database.apply_to_env()
+    pooled: Final = pod_pgbouncer_database_url(
+        PgBouncerSettings(),
+        os.environ,
+        token_auth=database.iam_token_db_auth or database.azure_postgresql_auth,
+    )
+    if isinstance(pooled, PgBouncerError):
+        sys.exit(f"LiteLLM collector: cannot use the pod's pgbouncer: {pooled.reason}")
+    if pooled is not None:
+        export_pooled_database_url(pooled)
+    settings: Final = CollectorSettings()
+    raw_address: Final = address_argument(argv, default=settings.address)
+    address: Final = raw_address if isinstance(raw_address, AddressError) else parse_collector_address(raw_address)
+    if isinstance(address, AddressError):
+        sys.exit(f"LiteLLM collector: {address.reason}")
+    asyncio.run(run_collector(address, drain_timeout=settings.drain_timeout_seconds))
+
+
+if __name__ == "__main__":
+    main(sys.argv[1:])
diff --git a/litellm/proxy/common_request_processing.py b/litellm/proxy/common_request_processing.py
index 4c9bdf867cd..e3a2b892721 100644
--- a/litellm/proxy/common_request_processing.py
+++ b/litellm/proxy/common_request_processing.py
@@ -190,6 +190,7 @@ from litellm.proxy.litellm_pre_call_utils import (
     refresh_proxy_server_request_body_snapshot,
     reject_url_valued_destination,
 )
+from litellm.proxy.policy_engine.response_retrieval import attach_post_call_pipelines_to_retrieval
 from litellm.types.utils import (
     ModelResponse,
     ModelResponseStream,
@@ -1849,7 +1850,6 @@ class ProxyBaseLLMRequestProcessing:
                 data=self.data,
                 user_api_key_dict=user_api_key_dict,
             )
-
         # Calculate request queue time after add_litellm_data_to_request
         # which sets arrival_time in proxy_server_request. Ends at start_time
         # (not a freshly captured time.time() here) so this window is exactly
@@ -1997,6 +1997,12 @@ class ProxyBaseLLMRequestProcessing:
             data=self.data,
             call_type=route_type,
         )
+        if route_type == "aget_responses":
+            attach_post_call_pipelines_to_retrieval(
+                data=self.data,
+                user_api_key_dict=user_api_key_dict,
+                llm_router=llm_router,
+            )
 
         # Refresh AFTER pre_call_hook: guardrails (e.g. Presidio PII masking) may
         # have mutated `self.data` in place, and the audit-trail snapshot taken in
@@ -3294,9 +3300,10 @@ class ProxyBaseLLMRequestProcessing:
         has completed.
 
         Guardrails routed through unified_guardrail are skipped, since they already ran
-        via its streaming iterator.  Guardrails that override
-        async_post_call_success_hook directly run here, including those that implement
-        apply_guardrail but keep their native lifecycle hooks.
+        via its streaming iterator, and so are guardrails a post_call policy pipeline
+        manages, since the pipeline ran them against the buffered stream.  Guardrails
+        that override async_post_call_success_hook directly run here, including those
+        that implement apply_guardrail but keep their native lifecycle hooks.
 
         This is audit-only — content has already been delivered to the client.
 
@@ -3306,12 +3313,18 @@ class ProxyBaseLLMRequestProcessing:
         _response = assembled_response
         try:
             from litellm.proxy.proxy_server import llm_router as _global_llm_router
-            from litellm.proxy.utils import _check_and_merge_model_level_guardrails
+            from litellm.proxy.utils import (
+                _check_and_merge_model_level_guardrails,
+                stream_gated_guardrail_names,
+            )
 
             guardrail_data = _check_and_merge_model_level_guardrails(data=captured_data, llm_router=_global_llm_router)
+            stream_gated: Final = stream_gated_guardrail_names(captured_data, captured_user_api_key_dict)
             for cb in litellm.callbacks:
                 if not isinstance(cb, CustomGuardrail):
                     continue
+                if cb.guardrail_name in stream_gated:
+                    continue
                 if not cb.should_run_guardrail(
                     data=guardrail_data,
                     event_type=GuardrailEventHooks.post_call,
diff --git a/litellm/proxy/common_utils/callback_utils.py b/litellm/proxy/common_utils/callback_utils.py
index 770963a1f24..561a53409f4 100644
--- a/litellm/proxy/common_utils/callback_utils.py
+++ b/litellm/proxy/common_utils/callback_utils.py
@@ -1,10 +1,12 @@
 import copy
+import json
 import os
 from collections.abc import Callable, Iterable, Mapping
 from dataclasses import dataclass
+from itertools import accumulate
 from typing import TYPE_CHECKING, Any, Final, Literal, NoReturn, Optional, TypeAlias
 
-from typing_extensions import assert_never
+from typing_extensions import ReadOnly, TypedDict, assert_never
 
 import litellm
 from litellm import get_secret
@@ -12,6 +14,7 @@ from litellm._logging import verbose_proxy_logger
 from litellm.constants import (
     CLIENT_OUTPUT_CEILING_METADATA_KEY,
     CONSUMED_REQUEST_TAGS_METADATA_KEY,
+    MAX_GUARDRAIL_SCAN_METADATA_HEADER_LENGTH,
     PRE_CALL_EXECUTED_GUARDRAILS_KEY,
     ROUTING_REQUEST_TAGS_METADATA_KEY,
     SESSION_DEPLOYMENT_AFFINITY_TTL_METADATA_KEY,
@@ -28,6 +31,7 @@ from litellm.proxy.common_utils.encrypt_decrypt_utils import (
     encrypt_value_helper,
 )
 from litellm.proxy.types_utils.utils import get_instance_fn
+from litellm.types.guardrails import GuardrailEventHooks
 from litellm.types.utils import (
     StandardLoggingGuardrailInformation,
     StandardLoggingPayload,
@@ -52,6 +56,15 @@ reset_color_code: Final = "\033[0m"
 TRUSTED_PILLAR_RESPONSE_HEADERS_METADATA_KEY: Final = "_pillar_response_headers_trusted"
 
 GUARDRAIL_SCAN_IDS_METADATA_KEY: Final = "guardrail_scan_ids"
+GUARDRAIL_SCAN_METADATA_METADATA_KEY: Final = "guardrail_scan_metadata"
+
+
+class GuardrailScanMetadata(TypedDict):
+    guardrail: ReadOnly[str | None]
+    stage: ReadOnly[str]
+    provider: ReadOnly[str]
+    scan_id: ReadOnly[str]
+
 
 if TYPE_CHECKING:
     from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLogging
@@ -450,6 +463,16 @@ def get_remaining_tokens_and_requests_from_request_data(data: dict) -> dict[str,
     return headers
 
 
+def _serialize_scan_metadata_header(entries: Iterable[object], *, max_length: int) -> str | None:
+    """Compact JSON list of scan metadata entries, dropping trailing entries so the header fits in max_length."""
+    encoded: Final = tuple(json.dumps(entry, separators=(",", ":")) for entry in entries)
+    lengths: Final = tuple(accumulate(len(item) + 1 for item in encoded))
+    kept: Final = sum(1 for length in lengths if length + 1 <= max_length)
+    if kept == 0:
+        return None
+    return f"[{','.join(encoded[:kept])}]"
+
+
 def get_logging_caching_headers(request_data: dict) -> dict | None:
     _metadata: Final[dict] = {}
     metadata_bucket: Final = request_data.get("metadata")
@@ -468,6 +491,15 @@ def get_logging_caching_headers(request_data: dict) -> dict | None:
     if scan_ids:
         headers["x-litellm-guardrail-scan-id"] = ",".join(scan_ids)
 
+    scan_metadata: Final = _metadata.get(GUARDRAIL_SCAN_METADATA_METADATA_KEY)
+    scan_metadata_header: Final = (
+        _serialize_scan_metadata_header(scan_metadata, max_length=MAX_GUARDRAIL_SCAN_METADATA_HEADER_LENGTH)
+        if isinstance(scan_metadata, (list, tuple))
+        else None
+    )
+    if scan_metadata_header:
+        headers["x-litellm-guardrail-scan-metadata"] = scan_metadata_header
+
     if "applied_policies" in _metadata:
         headers["x-litellm-applied-policies"] = ",".join(_metadata["applied_policies"])
 
@@ -501,6 +533,7 @@ LITELLM_PROXY_INTERNAL_METADATA_KEYS: Final = frozenset(
         "applied_policies",
         "applied_guardrails",
         GUARDRAIL_SCAN_IDS_METADATA_KEY,
+        GUARDRAIL_SCAN_METADATA_METADATA_KEY,
         "policy_sources",
         "guardrails",
         "guardrail_config",
@@ -565,21 +598,40 @@ def add_guardrail_to_applied_guardrails_header(request_data: dict, guardrail_nam
         _metadata["applied_guardrails"] = [guardrail_name]
 
 
-def add_guardrail_scan_id(request_data: dict, scan_id: str | None) -> None:
+def add_guardrail_scan_id(
+    request_data: dict[str, object],
+    scan_id: str | None,
+    *,
+    guardrail_name: str | None,
+    provider: str,
+    stage: GuardrailEventHooks,
+) -> None:
     """
-    Record a provider scan id so it can be surfaced to the caller.
+    Record a provider scan id, keyed to the guardrail execution that produced it, so it can be surfaced to the caller.
 
     Guardrails only return scan details to the client when they block, so allowed requests carry no
-    audit trail. Ids recorded here become the x-litellm-guardrail-scan-id response header.
+    audit trail. Ids recorded here become the x-litellm-guardrail-scan-id response header, and the
+    (guardrail, stage, provider, scan_id) entries become the x-litellm-guardrail-scan-metadata header.
     """
     if not scan_id:
         return
     _, _metadata = get_or_create_metadata_bucket(request_data)
     existing: Final = _metadata.get(GUARDRAIL_SCAN_IDS_METADATA_KEY)
-    scan_ids: Final = tuple(existing) if isinstance(existing, (list, tuple)) else ()
+    scan_ids: Final[tuple[object, ...]] = tuple(existing) if isinstance(existing, (list, tuple)) else ()
     if scan_id not in scan_ids:
         _metadata[GUARDRAIL_SCAN_IDS_METADATA_KEY] = (*scan_ids, scan_id)
 
+    entry: Final[GuardrailScanMetadata] = {
+        "guardrail": guardrail_name,
+        "stage": stage.value,
+        "provider": provider,
+        "scan_id": scan_id,
+    }
+    existing_entries: Final = _metadata.get(GUARDRAIL_SCAN_METADATA_METADATA_KEY)
+    entries: Final[tuple[object, ...]] = tuple(existing_entries) if isinstance(existing_entries, (list, tuple)) else ()
+    if entry not in entries:
+        _metadata[GUARDRAIL_SCAN_METADATA_METADATA_KEY] = (*entries, entry)
+
 
 def add_policy_to_applied_policies_header(request_data: dict, policy_name: str | None):
     """
diff --git a/litellm/proxy/common_utils/http_parsing_utils.py b/litellm/proxy/common_utils/http_parsing_utils.py
index 54a0f18fd63..845589aee7a 100644
--- a/litellm/proxy/common_utils/http_parsing_utils.py
+++ b/litellm/proxy/common_utils/http_parsing_utils.py
@@ -39,7 +39,7 @@ def _is_form_content_type(content_type: str) -> bool:
     return _normalize_media_type(content_type) in _FORM_CONTENT_TYPES
 
 
-def _is_json_content_type(content_type: str) -> bool:
+def is_json_content_type(content_type: str) -> bool:
     """True iff the body should be parsed as JSON."""
     return _normalize_media_type(content_type) == "application/json"
 
@@ -213,6 +213,18 @@ async def _read_request_body(request: Request | None) -> dict:
         return {}
 
 
+async def read_raw_json_body(request: Request | None) -> bytes | None:
+    if request is None or _safe_get_request_parsed_body(request=request) is None:
+        return None
+    content_type: Final = _safe_get_request_headers(request=request).get("content-type", "")
+    if _is_form_content_type(content_type):
+        return None
+    try:
+        return await request.body()
+    except RuntimeError:
+        return None
+
+
 def _safe_get_request_parsed_body(request: Request | None) -> dict | None:
     if request is None:
         return None
@@ -406,7 +418,7 @@ async def get_request_body(request: Request) -> dict[str, Any]:
     """
     if request.method == "POST":
         content_type: Final = request.headers.get("content-type", "")
-        if _is_json_content_type(content_type):
+        if is_json_content_type(content_type):
             return await _read_request_body(request)
         elif _is_form_content_type(content_type):
             return await get_form_data(request)
diff --git a/litellm/proxy/common_utils/model_listing_utils.py b/litellm/proxy/common_utils/model_listing_utils.py
index 213a697b3dd..4b3ff2711b3 100644
--- a/litellm/proxy/common_utils/model_listing_utils.py
+++ b/litellm/proxy/common_utils/model_listing_utils.py
@@ -10,12 +10,24 @@ legacy internal names with `general_settings.use_team_public_model_name: false`.
 
 from __future__ import annotations
 
-from collections.abc import Mapping, Sequence
+import re
+from collections.abc import Container, Mapping, Sequence
+from dataclasses import dataclass
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Final, cast
 
+import litellm
+
 if TYPE_CHECKING:
     from litellm.router import Router
+    from litellm.types.proxy.model_listing import ModelInfoResponse
+
+CLAUDE_CODE_PICKER_PATTERN: Final = re.compile(r"claude|anthropic", re.IGNORECASE)
+GATEWAY_CLIENT_HEADER: Final = "x-gateway-client"
+CLAUDE_CODE_CLIENT: Final = "claude-code"
+_CLAUDE_CODE_ALIAS_PREFIX: Final = "claude-router-"
+_ONE_MILLION_SUFFIX: Final = "[1m]"
+_ONE_MILLION_TOKENS: Final = 1_000_000
 
 
 def configured_display_names(
@@ -40,6 +52,115 @@ def configured_display_names(
     )
 
 
+def _unmarked(name: str) -> str:
+    return name[: -len(_ONE_MILLION_SUFFIX)] if name.lower().endswith(_ONE_MILLION_SUFFIX) else name
+
+
+def _compatibility_id(model_id: str) -> str:
+    return f"{_CLAUDE_CODE_ALIAS_PREFIX}{model_id.encode().hex()}"
+
+
+def _decoded_compatibility_id(view_id: str) -> str | None:
+    encoded: Final = _unmarked(view_id).removeprefix(_CLAUDE_CODE_ALIAS_PREFIX)
+    if encoded == _unmarked(view_id):
+        return None
+    try:
+        model_id: Final = bytes.fromhex(encoded).decode()
+    except (ValueError, UnicodeDecodeError):
+        return None
+    return model_id if _compatibility_id(model_id) == _unmarked(view_id) else None
+
+
+def claude_code_model_id(
+    model_id: str,
+    max_input_tokens: float | None,
+    routing_names: Container[str],
+) -> str:
+    """The collision-free id Claude Code's picker lists a model under."""
+    if "*" in model_id:
+        return model_id
+    shaped: Final = model_id if CLAUDE_CODE_PICKER_PATTERN.search(model_id) else _compatibility_id(model_id)
+    one_million: Final = max_input_tokens is not None and max_input_tokens >= _ONE_MILLION_TOKENS
+    marked: Final = (
+        f"{shaped}{_ONE_MILLION_SUFFIX}" if one_million and not shaped.lower().endswith(_ONE_MILLION_SUFFIX) else shaped
+    )
+    return next(
+        (
+            name
+            for name in (marked, shaped)
+            if name == model_id or claude_code_group_name(name, routing_names) == model_id
+        ),
+        model_id,
+    )
+
+
+def claude_code_group_name(view_id: str, routing_names: Container[str]) -> str | None:
+    """Decode a canonical compatibility id only when no configured route claims it."""
+    if view_id in routing_names:
+        return None
+    unmarked: Final = _unmarked(view_id)
+    if unmarked != view_id and unmarked in routing_names:
+        return unmarked
+    model_id: Final = _decoded_compatibility_id(view_id)
+    return model_id if model_id and model_id in routing_names else None
+
+
+def is_claude_code_client(headers: Mapping[str, str]) -> bool:
+    """Claude Code itself, or a client asking for its view of the listing the way Ramp Router's does"""
+    from litellm.llms.anthropic.common_utils import is_claude_code_user_agent
+
+    return (
+        is_claude_code_user_agent(headers.get("user-agent", ""))
+        or headers.get(GATEWAY_CLIENT_HEADER, "").lower() == CLAUDE_CODE_CLIENT
+    )
+
+
+def claude_code_view_ids(
+    rows: Sequence[ModelInfoResponse],
+    headers: Mapping[str, str],
+    routing_names: Container[str],
+) -> Mapping[str, str]:
+    """served id -> Claude Code id for the requested listing view"""
+    if not is_claude_code_client(headers):
+        return MappingProxyType({})
+    return MappingProxyType(
+        {row["id"]: claude_code_model_id(row["id"], row.get("max_input_tokens"), routing_names) for row in rows}
+    )
+
+
+@dataclass(frozen=True, slots=True)
+class ClaudeCodeRoutingNames:
+    """Existing routes always own their names, including aliases and wildcard routes."""
+
+    llm_router: Router | None
+    team_id: str | None = None
+    alias_maps: tuple[object, ...] = ()
+
+    def __contains__(self, name: object) -> bool:
+        if not isinstance(name, str):
+            return False
+        if name in litellm.model_alias_map or any(
+            isinstance(aliases, Mapping) and name in aliases for aliases in self.alias_maps
+        ):
+            return True
+        if self.llm_router is None:
+            return False
+        return (
+            name in self.llm_router.model_group_alias
+            or self.llm_router.has_model_id(name)
+            or bool(self.llm_router.get_candidate_model_ids_for_route(name, self.team_id))
+        )
+
+
+def claude_code_requested_group(
+    requested: str,
+    llm_router: Router,
+    team_id: str | None,
+    alias_maps: tuple[object, ...] = (),
+) -> str | None:
+    return claude_code_group_name(requested, ClaudeCodeRoutingNames(llm_router, team_id, alias_maps))
+
+
 class TeamModelNameTranslator:
     """Translates internal team routing keys to their public names for the model
     listing/retrieve responses. Stateless; the live router and general_settings
diff --git a/litellm/proxy/common_utils/reset_budget_job.py b/litellm/proxy/common_utils/reset_budget_job.py
index f2648c8466e..35e74418628 100644
--- a/litellm/proxy/common_utils/reset_budget_job.py
+++ b/litellm/proxy/common_utils/reset_budget_job.py
@@ -224,33 +224,31 @@ def _queue_budget_linked_resets(
 
 
 def _queue_enduser_resets(writes: LinkedSpendResetWrites, cascade: "_BudgetCascade") -> None:
-    """End users are matched by id rather than budget link: rows with no
-    budget_id ride the default budget tier (litellm.max_end_user_budget_id).
-    Zero-before-decrement ordering matters here too (see
-    _queue_budget_linked_resets)."""
-    if not cascade.rollover_caps:
-        if cascade.endusers:
-            writes.queue_spend_zero(
-                where={"user_id": {"in": [row.user_id for row in cascade.endusers]}}
-            )  # mutable-ok: prisma where filter must be a dict
+    """End users reset on the budget link like every other gated table, plus a
+    NULL-budget_id branch: rows created implicitly persist no link and ride the
+    default tier (litellm.max_end_user_budget_id).
+
+    Matching on the link rather than enumerating user ids keeps a statement's
+    bind count proportional to the expiring tiers instead of the customer
+    population, which past ~32,700 dependents exceeds PostgreSQL's per-statement
+    bind ceiling and wedges the cascade permanently (#40564).
+    """
+    _queue_budget_linked_resets(writes, cascade, extra=_SPENT_ROWS_WHERE)
+    default_budget_id: Final = litellm.max_end_user_budget_id
+    if default_budget_id is None or default_budget_id not in cascade.budget_ids:
         return
-    tiered: Final = tuple((row.budget_id or litellm.max_end_user_budget_id, row.user_id) for row in cascade.endusers)
-    for budget_id, cap in cascade.rollover_caps.items():
-        if not (
-            user_ids := [uid for bid, uid in tiered if bid == budget_id]
-        ):  # mutable-ok: prisma "in" filter takes a list
-            continue
+    cap: Final = cascade.rollover_caps.get(default_budget_id)
+    if cap is None:
         writes.queue_spend_zero(
-            where={"user_id": {"in": user_ids}, "spend": {"lte": cap}}
+            where={"budget_id": None, **_SPENT_ROWS_WHERE}
         )  # mutable-ok: prisma where filter must be a dict
-        writes.queue_spend_decrement(
-            where={"user_id": {"in": user_ids}, "spend": {"gt": cap}}, amount=cap
-        )  # mutable-ok: prisma where filter must be a dict
-    plain: Final = [
-        uid for bid, uid in tiered if bid is None or bid not in cascade.rollover_caps
-    ]  # mutable-ok: prisma "in" filter takes a list
-    if plain:
-        writes.queue_spend_zero(where={"user_id": {"in": plain}})  # mutable-ok: prisma where filter must be a dict
+        return
+    writes.queue_spend_zero(
+        where={"budget_id": None, "spend": {"gt": 0, "lte": cap}}
+    )  # mutable-ok: prisma where filter must be a dict
+    writes.queue_spend_decrement(
+        where={"budget_id": None, "spend": {"gt": cap}}, amount=cap
+    )  # mutable-ok: prisma where filter must be a dict
 
 
 @dataclass(frozen=True, slots=True)
diff --git a/litellm/proxy/db/db_lookup_gate.py b/litellm/proxy/db/db_lookup_gate.py
new file mode 100644
index 00000000000..2fd427687bd
--- /dev/null
+++ b/litellm/proxy/db/db_lookup_gate.py
@@ -0,0 +1,23 @@
+import asyncio
+from typing import Final
+
+from litellm.constants import PROXY_DB_LOOKUP_MAX_CONCURRENCY
+
+
+class LoopBoundSemaphore:
+    __slots__ = ("_loop", "_semaphore", "_value")
+
+    def __init__(self, value: int) -> None:
+        self._value: Final = value
+        self._loop: asyncio.AbstractEventLoop | None = None
+        self._semaphore: asyncio.Semaphore | None = None
+
+    def current(self) -> asyncio.Semaphore:
+        loop: Final = asyncio.get_running_loop()
+        if self._semaphore is None or self._loop is not loop:
+            self._semaphore = asyncio.Semaphore(self._value)
+            self._loop = loop
+        return self._semaphore
+
+
+db_lookup_gate: Final = LoopBoundSemaphore(PROXY_DB_LOOKUP_MAX_CONCURRENCY)
diff --git a/litellm/proxy/db/db_transaction_queue/pod_lock_manager.py b/litellm/proxy/db/db_transaction_queue/pod_lock_manager.py
index 4be1331e955..bc67617e444 100644
--- a/litellm/proxy/db/db_transaction_queue/pod_lock_manager.py
+++ b/litellm/proxy/db/db_transaction_queue/pod_lock_manager.py
@@ -1,10 +1,11 @@
 import asyncio
 import json
+import logging
 from typing import TYPE_CHECKING, Any, Final
 
 from litellm._logging import verbose_proxy_logger
 from litellm._uuid import uuid
-from litellm.caching.redis_cache import RedisCache
+from litellm.caching.redis_cache import RedisCache, log_redis_failure
 from litellm.constants import DEFAULT_CRON_JOB_LOCK_TTL_SECONDS
 from litellm.proxy.db.db_transaction_queue.base_update_queue import service_logger_obj
 from litellm.types.services import ServiceTypes
@@ -109,7 +110,7 @@ end
                     )
             return False
         except Exception as e:
-            verbose_proxy_logger.error("Error acquiring Redis lock for %s: %s", cronjob_id, e)
+            log_redis_failure(verbose_proxy_logger, logging.ERROR, f"Error acquiring Redis lock for {cronjob_id}", e)
             return False
 
     async def release_lock(
@@ -151,7 +152,7 @@ end
                     cronjob_id,
                 )
         except Exception as e:
-            verbose_proxy_logger.error("Error releasing Redis lock for %s: %s", cronjob_id, e)
+            log_redis_failure(verbose_proxy_logger, logging.ERROR, f"Error releasing Redis lock for {cronjob_id}", e)
 
     async def _compare_and_delete_lock(self, lock_key: str) -> int:
         """
diff --git a/litellm/proxy/db/db_url_settings.py b/litellm/proxy/db/db_url_settings.py
index 4a0231ad9df..e93bc96da69 100644
--- a/litellm/proxy/db/db_url_settings.py
+++ b/litellm/proxy/db/db_url_settings.py
@@ -34,16 +34,25 @@ writer's connection params (pool size, timeouts, pgbouncer mode) for the
 ones the reader URL does not pin itself.
 """
 
+import _ssl
+import hashlib
 import os
+import socket
+import ssl
+import struct
+import sys
+import tempfile
 import urllib.parse
-from collections.abc import Mapping
+from collections.abc import Callable, Mapping, Sequence
 from functools import partial
+from pathlib import Path
 from types import MappingProxyType
-from typing import Annotated, Final, cast
+from typing import Annotated, Final, Protocol, TypeAlias, cast
 
 from pydantic import AliasChoices, BeforeValidator, Field
 from pydantic_settings import BaseSettings, SettingsConfigDict
 
+from litellm.proxy.db.pgbouncer import database_url_is_pooled
 from litellm.proxy.db.token_auth import (
     AZURE_POSTGRESQL_AUTH_ENV_VAR,
     DEFAULT_POSTGRES_PORT,
@@ -126,21 +135,100 @@ def add_missing_query_params(url: str, params: Mapping[str, str | int | float])
 
 
 LIBPQ_VERIFY_SSLMODES: Final[frozenset[str]] = frozenset({"verify-ca", "verify-full"})
+PEM_CERT_HEADER: Final = b"-----BEGIN CERTIFICATE-----"
+PG_SSL_REQUEST: Final = struct.pack("!ii", 8, 80877103)
+TLS_PROBE_TIMEOUT_SECONDS: Final = 10.0
+
+RootCertResolver: TypeAlias = Callable[[str, str, int], str]  # mutable-ok: Callable parameter syntax
 
 
-def translate_libpq_ssl_params(url: str) -> str:
+class _VerifiedChainSource(Protocol):
+    def get_verified_chain(self) -> Sequence[_ssl.Certificate] | None: ...
+
+
+def _verified_chain_der(tls: ssl.SSLSocket) -> tuple[bytes, ...]:
+    if sys.version_info >= (3, 13):
+        return tuple(tls.get_verified_chain())
+    legacy: Final = cast(  # cast-ok: the stub omits _sslobj, the C object has get_verified_chain since 3.10
+        "_VerifiedChainSource | None",
+        tls._sslobj,  # pyright: ignore[reportAttributeAccessIssue, reportUnknownMemberType]  # public API only from 3.13
+    )
+    chain: Final = () if legacy is None else legacy.get_verified_chain() or ()
+    return tuple(cert.public_bytes(_ssl.ENCODING_DER) for cert in chain)
+
+
+def _server_trust_anchor(cafile: str, host: str, port: int) -> bytes | None:
+    try:
+        context: Final = ssl.create_default_context(cafile=cafile)
+        with socket.create_connection((host, port), timeout=TLS_PROBE_TIMEOUT_SECONDS) as raw:
+            raw.sendall(PG_SSL_REQUEST)
+            if raw.recv(1) != b"S":
+                return None
+            with context.wrap_socket(raw, server_hostname=host) as tls:
+                chain: Final = _verified_chain_der(tls)
+    except (OSError, ValueError):
+        return None
+    return chain[-1] if chain else None
+
+
+def pin_bundle_root(cert_path: str, host: str, port: int) -> str:
+    """Reduce a multi-root CA bundle to the one root that verifies ``host``.
+
+    Prisma's ``sslcert`` loads a single PEM certificate (native-tls
+    ``Certificate::from_pem``), so pointing it at a bundle such as the AWS RDS
+    global bundle trusts only the first of its 108 regional roots and the
+    handshake fails with "unable to get local issuer certificate" for every
+    other region. A single-certificate file is returned as is. For a bundle,
+    one verifying handshake (chain and hostname, whole bundle as trust store)
+    identifies the trust anchor the server actually chains to, which is
+    written to a single-certificate file for Prisma. If the probe fails the
+    bundle path is returned unchanged, so Prisma fails closed exactly as
+    before rather than trusting anything the bundle would not.
+    """
+    try:
+        if Path(cert_path).read_bytes().count(PEM_CERT_HEADER) < 2:
+            return cert_path
+    except OSError:
+        return cert_path
+    root: Final = _server_trust_anchor(cert_path, host, port)
+    if root is None:
+        return cert_path
+    pinned: Final = Path(tempfile.gettempdir()) / f"litellm-sslcert-{hashlib.sha256(root).hexdigest()[:16]}.pem"
+    return str(pinned) if _replace_file(pinned, ssl.DER_cert_to_PEM_cert(root)) else cert_path
+
+
+def _replace_file(target: Path, content: str) -> bool:
+    """Write ``content`` to a private temp file and rename it over ``target``, so
+    readers never see a partial file and a symlink planted at ``target`` is
+    replaced rather than followed."""
+    try:
+        fd, staged = tempfile.mkstemp(dir=target.parent, prefix=f"{target.name}.")
+    except OSError:
+        return False
+    try:
+        with os.fdopen(fd, "w") as handle:
+            handle.write(content)
+        os.replace(staged, target)
+    except OSError:
+        Path(staged).unlink(missing_ok=True)
+        return False
+    return True
+
+
+def translate_libpq_ssl_params(url: str, resolve_root_cert: RootCertResolver = pin_bundle_root) -> str:
     """Rewrite libpq's certificate-verification params into Prisma's dialect.
 
     Prisma's engine only knows ``sslmode=disable|prefer|require``, ``sslcert``
-    (the CA bundle) and ``sslaccept=strict``. It silently discards
+    (a single CA certificate) and ``sslaccept=strict``. It silently discards
     ``sslrootcert`` and downgrades ``sslmode=verify-ca`` / ``verify-full`` to
     ``prefer``, so a URL copied from libpq / RDS docs connects over TLS with no
     certificate check at all. ``verify-ca`` and ``verify-full`` both become
     ``require`` (Prisma has no CA-only mode), ``sslrootcert`` becomes
-    ``sslcert``, and either one turns on ``sslaccept=strict`` (chain and
-    hostname), matching libpq where a root cert makes ``require`` verify.
-    Prisma params the operator pinned themselves win; anything else is left
-    untouched.
+    ``sslcert`` (run through ``resolve_root_cert``, which pins a multi-root
+    bundle down to the server's root), and either one turns on
+    ``sslaccept=strict`` (chain and hostname), matching libpq where a root
+    cert makes ``require`` verify. Prisma params the operator pinned
+    themselves win; anything else is left untouched.
     """
     parsed: Final = urllib.parse.urlsplit(url)
     pairs: Final = tuple(urllib.parse.parse_qsl(parsed.query, keep_blank_values=True))
@@ -154,7 +242,9 @@ def translate_libpq_ssl_params(url: str) -> str:
         if key != "sslrootcert"
     )
     root_cert: Final = tuple(
-        ("sslcert", value) for key, value in pairs if key == "sslrootcert" and "sslcert" not in keys
+        ("sslcert", resolve_root_cert(value, parsed.hostname or "", parsed.port or int(DEFAULT_POSTGRES_PORT)))
+        for key, value in pairs
+        if key == "sslrootcert" and "sslcert" not in keys
     )
     strict: Final = () if "sslaccept" in keys else (("sslaccept", "strict"),)
     query: Final = urllib.parse.urlencode(translated + root_cert + strict)
@@ -269,8 +359,12 @@ class DatabaseURLSettings(BaseSettings):
         Raises ``RuntimeError`` (naming the offending vars) when token auth is
         enabled but a required field is missing — the proxy cannot recover
         from this and a clear startup error beats a Prisma connect failure.
+        A ``DATABASE_URL`` the supervisor pointed at the in-container PgBouncer
+        is kept even under token auth: the pooler renews the token upstream.
         """
         auth: Final = self.token_auth()
+        if auth is not None and database_url_is_pooled():
+            return None
         if auth is not None:
             missing: Final = tuple(
                 env
diff --git a/litellm/proxy/db/exception_handler.py b/litellm/proxy/db/exception_handler.py
index f469587ab8e..2cee5128c66 100644
--- a/litellm/proxy/db/exception_handler.py
+++ b/litellm/proxy/db/exception_handler.py
@@ -221,6 +221,18 @@ class PrismaDBExceptionHandler:
             or "write conflict or a deadlock" in error_message
         )
 
+    @staticmethod
+    def is_read_only_transaction_error(e: Exception) -> bool:
+        """True iff ``e`` is Postgres SQLSTATE 25006 surfaced through prisma: the
+        pooled session answers reads but rejects writes, so the connection is
+        poisoned until the client is recreated."""
+        import prisma
+
+        if not isinstance(e, _exception_types(prisma.errors.PrismaError)):
+            return False
+        error_message: Final = str(e).lower()
+        return '"25006"' in error_message or "read-only transaction" in error_message
+
     @staticmethod
     def is_prisma_engine_internal_error(e: Exception) -> bool:
         """True iff ``e`` is a non-``PrismaError`` exception raised from inside
diff --git a/litellm/proxy/db/gateway_request_tracking.py b/litellm/proxy/db/gateway_request_tracking.py
index bebd74e877c..c9ace68db33 100644
--- a/litellm/proxy/db/gateway_request_tracking.py
+++ b/litellm/proxy/db/gateway_request_tracking.py
@@ -10,13 +10,28 @@ strings rather than passing the raw path through. Nothing a caller sends can
 add a key, so the fold and the table it commits to are bounded by (days x
 routes) however much traffic arrives, and the response path carries no
 unbounded queue that would block once full.
+
+A flush commits its whole snapshot as one multi-row ``INSERT ... ON CONFLICT DO
+UPDATE`` rather than one upsert per key, so a worker costs the primary one
+statement per interval however many routes it served. With
+``use_redis_transaction_buffer`` on, workers instead push their snapshot to a
+Redis list and one lock-holding pod folds every entry and writes the table, so
+the deployment as a whole costs the primary one statement per interval.
 """
 
-from dataclasses import asdict
+import json
+from collections.abc import AsyncIterator, Iterable
 from datetime import datetime, timezone
-from typing import TYPE_CHECKING, Final
+from itertools import chain
+from types import MappingProxyType
+from typing import TYPE_CHECKING, Final, TypeAlias
+
+from pydantic import TypeAdapter
 
 from litellm._logging import verbose_proxy_logger
+from litellm.caching import RedisCache
+from litellm.constants import MAX_REDIS_BUFFER_DEQUEUE_COUNT, REDIS_GATEWAY_REQUESTS_BUFFER_KEY
+from litellm.proxy.db.db_transaction_queue.pod_lock_manager import PodLockManager
 from litellm.proxy.middleware.billable_request_metrics_middleware import BillableCategory
 from litellm.types.proxy.gateway_requests import (
     GatewayRequestCounts,
@@ -28,6 +43,15 @@ if TYPE_CHECKING:
     from litellm.proxy.utils import PrismaClient
 
 _EMPTY: Final = GatewayRequestCounts(successful_requests=0, failed_requests=0)
+_TABLE: Final = '"LiteLLM_DailyGatewayRequests"'
+_COLUMNS_PER_ROW: Final = 5
+_UTC_NOW: Final = "(NOW() AT TIME ZONE 'UTC')"
+GATEWAY_REQUESTS_JOB_NAME: Final = "update_gateway_requests_job"
+
+_BufferedRows: TypeAlias = tuple[tuple[str, str, str, int, int], ...]
+_BUFFERED_ROWS: Final = TypeAdapter(_BufferedRows)
+_BUFFERED_ENTRIES: Final = TypeAdapter(tuple[str | bytes, ...])
+_NO_COUNTS: Final[GatewayRequestSnapshot] = MappingProxyType({})
 
 
 def _utc_date() -> str:
@@ -59,20 +83,54 @@ class GatewayRequestAccumulator:
         route) however long the database is unreachable.
 
         This buys at-least-once, not exactly-once, and the cost is worth stating.
-        The batch commits inside its context manager's ``__aexit__``, so a failure
-        raised after the transaction committed (a connection dropped while reading
-        the acknowledgement) restores counts that are already persisted, and the
-        next flush increments them a second time. Exactly-once would need a dedup
-        key the upserts could ignore on replay. For a traffic-volume metric a rare
+        The statement commits on the server before its acknowledgement is read, so
+        a failure raised after the commit (a connection dropped while reading the
+        acknowledgement) restores counts that are already persisted, and the next
+        flush increments them a second time. Exactly-once would need a dedup key
+        the upsert could ignore on replay. For a traffic-volume metric a rare
         overcount on a dropped acknowledgement beats losing a whole interval to
         every database blip, so the trade is deliberate.
         """
-        for key, counts in snapshot.items():
-            existing = self._counts.get(key, _EMPTY)
-            self._counts[key] = GatewayRequestCounts(
-                successful_requests=existing.successful_requests + counts.successful_requests,
-                failed_requests=existing.failed_requests + counts.failed_requests,
-            )
+        self._counts = dict(fold_counts(chain(self._counts.items(), snapshot.items())))  # mutable-ok: fold replaced
+
+
+def fold_counts(items: Iterable[tuple[GatewayRequestKey, GatewayRequestCounts]]) -> GatewayRequestSnapshot:
+    """Sum counts key-wise; the result stays bounded by (date x category x route)."""
+    folded: Final[dict[GatewayRequestKey, GatewayRequestCounts]] = {}  # mutable-ok: local fold returned once
+    for key, counts in items:
+        existing = folded.get(key, _EMPTY)
+        folded[key] = GatewayRequestCounts(
+            successful_requests=existing.successful_requests + counts.successful_requests,
+            failed_requests=existing.failed_requests + counts.failed_requests,
+        )
+    return folded
+
+
+def build_gateway_requests_upsert(snapshot: GatewayRequestSnapshot) -> tuple[str, tuple[str | int, ...]]:
+    """
+    One ``INSERT ... ON CONFLICT DO UPDATE`` that increments every (date, category,
+    route) in the snapshot. Rows are ordered by the conflict key so concurrent
+    writers lock rows in the same order and cannot deadlock.
+    """
+    ordered: Final = sorted(snapshot.items(), key=lambda item: (item[0].date, item[0].category, item[0].route))
+    rows: Final = ", ".join(
+        f"(${base + 1}::text, ${base + 2}::text, ${base + 3}::text, ${base + 4}::bigint, ${base + 5}::bigint, {_UTC_NOW})"
+        for base in range(0, len(ordered) * _COLUMNS_PER_ROW, _COLUMNS_PER_ROW)
+    )
+    sql: Final = (
+        f'INSERT INTO {_TABLE} ("date", "category", "route", "successful_requests", "failed_requests", "updated_at")\n'
+        f"VALUES {rows}\n"
+        'ON CONFLICT ("date", "category", "route") DO UPDATE SET\n'
+        f'  "successful_requests" = {_TABLE}."successful_requests" + EXCLUDED."successful_requests",\n'
+        f'  "failed_requests" = {_TABLE}."failed_requests" + EXCLUDED."failed_requests",\n'
+        f'  "updated_at" = {_UTC_NOW}'
+    )
+    params: Final[tuple[str | int, ...]] = tuple(
+        value
+        for key, counts in ordered
+        for value in (key.date, key.category, key.route, counts.successful_requests, counts.failed_requests)
+    )
+    return sql, params
 
 
 async def commit_gateway_requests_to_db(
@@ -80,50 +138,130 @@ async def commit_gateway_requests_to_db(
     prisma_client: "PrismaClient",
     snapshot: GatewayRequestSnapshot,
 ) -> None:
-    """Upsert one incrementing row per (date, category, route)."""
+    """Increment every (date, category, route) in the snapshot with a single statement."""
     if not snapshot:
         return
 
-    ordered: Final = sorted(snapshot.items(), key=lambda item: (item[0].date, item[0].category, item[0].route))
+    sql, params = build_gateway_requests_upsert(snapshot)
+    await prisma_client.db.execute_raw(sql, *params)  # pyright: ignore[reportAny]  # untyped prisma client
 
-    # pyright: ignore[reportAny] on both lines -- prisma's generated client is untyped,
-    # so .db and every table action off it resolve to Any at this boundary. The dict
-    # literals below are the shape prisma's generated inputs require.
-    async with prisma_client.db.batch_() as batcher:  # pyright: ignore[reportAny]  # untyped prisma client
-        for key, counts in ordered:
-            columns = asdict(key)
-            batcher.litellm_dailygatewayrequests.upsert(  # pyright: ignore[reportAny]  # untyped prisma client
-                where={"date_category_route": columns},  # mutable-ok: prisma input is dict-shaped
-                data={  # mutable-ok: prisma input is dict-shaped
-                    "create": {  # mutable-ok: prisma input is dict-shaped
-                        **columns,
-                        "successful_requests": counts.successful_requests,
-                        "failed_requests": counts.failed_requests,
-                    },
-                    "update": {  # mutable-ok: prisma input is dict-shaped
-                        "successful_requests": {"increment": counts.successful_requests},  # mutable-ok: as above
-                        "failed_requests": {"increment": counts.failed_requests},  # mutable-ok: as above
-                    },
-                },
+    verbose_proxy_logger.debug(
+        "Gateway request tracking - committed %d aggregated rows in one statement", len(snapshot)
+    )
+
+
+class GatewayRequestRedisBuffer:
+    """
+    Folds every worker's snapshot through one Redis list so a single pod per
+    interval writes the table, mirroring the spend writer's transaction buffer.
+
+    Each entry is one worker's snapshot as JSON rows; the lock holder pops them,
+    sums them, and commits one statement. A commit failure pushes the summed
+    rows back so the next holder retries, keeping the at-least-once guarantee.
+    If that push fails too, the rows go back to the holder's own accumulator so
+    they ride along with its next flush instead of vanishing with the pop.
+    """
+
+    def __init__(self, *, redis_cache: RedisCache, pod_lock_manager: PodLockManager) -> None:
+        self._redis_cache: Final = redis_cache
+        self._pod_lock_manager: Final = pod_lock_manager
+
+    async def push(self, snapshot: GatewayRequestSnapshot) -> None:
+        if not snapshot:
+            return
+        rows: Final[_BufferedRows] = tuple(
+            (key.date, key.category, key.route, counts.successful_requests, counts.failed_requests)
+            for key, counts in snapshot.items()
+        )
+        await self._redis_cache.async_rpush(key=REDIS_GATEWAY_REQUESTS_BUFFER_KEY, values=(json.dumps(rows),))
+
+    async def _pop_batch(self) -> tuple[str | bytes, ...]:
+        popped: Final[object] = await self._redis_cache.async_lpop(  # pyright: ignore[reportAny]  # redis returns Any
+            key=REDIS_GATEWAY_REQUESTS_BUFFER_KEY, count=MAX_REDIS_BUFFER_DEQUEUE_COUNT
+        )
+        if not popped:
+            return ()
+        return _BUFFERED_ENTRIES.validate_python(popped if isinstance(popped, list) else (popped,))
+
+    async def _pop_all(self) -> AsyncIterator[str | bytes]:
+        while True:
+            batch = await self._pop_batch()
+            for entry in batch:
+                yield entry
+            if len(batch) < MAX_REDIS_BUFFER_DEQUEUE_COUNT:
+                return
+
+    async def pop(self) -> GatewayRequestSnapshot:
+        entries: Final = tuple([entry async for entry in self._pop_all()])
+        return fold_counts(
+            (
+                GatewayRequestKey(date=date, category=category, route=route),
+                GatewayRequestCounts(successful_requests=succeeded, failed_requests=failed),
             )
+            for entry in entries
+            for date, category, route, succeeded, failed in _BUFFERED_ROWS.validate_json(entry)
+        )
 
-    verbose_proxy_logger.debug("Gateway request tracking - committed %d aggregated rows", len(ordered))
+    async def commit_if_leader(self, prisma_client: "PrismaClient") -> GatewayRequestSnapshot:
+        """
+        Drain the list and write it as one statement, but only on the pod holding the job lock.
+
+        The lock is a lease, never released: the holder re-enters it on every flush and
+        keeps committing alone until the TTL lapses, so the primary sees one statement
+        per flush interval deployment-wide instead of one per worker.
+
+        Returns the popped rows that could be neither committed nor re-queued, for the
+        caller to keep in memory. Empty on success.
+        """
+        if not await self._pod_lock_manager.acquire_lock(cronjob_id=GATEWAY_REQUESTS_JOB_NAME):
+            return _NO_COUNTS
+        buffered: Final = await self.pop()
+        try:
+            await commit_gateway_requests_to_db(prisma_client=prisma_client, snapshot=buffered)
+        except Exception:  # noqa: BLE001 -- a failed commit must not stop the scheduler
+            verbose_proxy_logger.warning(
+                "Gateway request tracking - failed to commit %d buffered rows, re-queuing to Redis for the next flush",
+                len(buffered),
+                exc_info=True,
+            )
+            return await self._requeue(buffered)
+        return _NO_COUNTS
+
+    async def _requeue(self, snapshot: GatewayRequestSnapshot) -> GatewayRequestSnapshot:
+        try:
+            await self.push(snapshot)
+        except Exception:  # noqa: BLE001 -- the rows go back to the caller's accumulator instead
+            verbose_proxy_logger.warning(
+                "Gateway request tracking - Redis re-queue failed, keeping %d rows in memory for the next flush",
+                len(snapshot),
+                exc_info=True,
+            )
+            return snapshot
+        return _NO_COUNTS
 
 
 async def flush_gateway_requests(
     prisma_client: "PrismaClient",
     accumulator: GatewayRequestAccumulator,
+    redis_buffer: GatewayRequestRedisBuffer | None = None,
 ) -> None:
     """
     Scheduler entrypoint. Never raises: a metering failure must not kill the job.
 
+    With ``redis_buffer`` the snapshot goes to Redis and only the lease holder
+    writes to Postgres. Shutdown passes no buffer so a departing worker writes its
+    own counts directly instead of parking them behind a lease it may not hold.
+
     ``CancelledError`` is deliberately not caught, so a flush cancelled during
     shutdown drops its snapshot rather than restoring counts onto an accumulator
     the process is about to discard.
     """
     snapshot: Final = accumulator.drain()
     try:
-        await commit_gateway_requests_to_db(prisma_client=prisma_client, snapshot=snapshot)
+        if redis_buffer is None:
+            await commit_gateway_requests_to_db(prisma_client=prisma_client, snapshot=snapshot)
+        else:
+            await redis_buffer.push(snapshot)
     except Exception:  # noqa: BLE001 -- a failed flush must not stop the scheduler
         accumulator.restore(snapshot)
         verbose_proxy_logger.warning(
@@ -131,3 +269,13 @@ async def flush_gateway_requests(
             len(snapshot),
             exc_info=True,
         )
+        return
+    if redis_buffer is None:
+        return
+    try:
+        accumulator.restore(await redis_buffer.commit_if_leader(prisma_client))
+    except Exception:  # noqa: BLE001 -- entries still in Redis are drained by the next flush
+        verbose_proxy_logger.warning(
+            "Gateway request tracking - leader drain failed, buffered rows stay in Redis for the next flush",
+            exc_info=True,
+        )
diff --git a/litellm/proxy/db/health_check_latest.py b/litellm/proxy/db/health_check_latest.py
new file mode 100644
index 00000000000..35bc838379c
--- /dev/null
+++ b/litellm/proxy/db/health_check_latest.py
@@ -0,0 +1,96 @@
+"""
+Latest health-check row per model, deduplicated by Postgres.
+
+prisma-client-py's ``find_many(distinct=...)`` dedups client-side: the emitted
+SQL carries no DISTINCT, so the whole append-only history table streams to the
+worker on every call. ``SELECT DISTINCT ON`` keeps the transfer at one row per
+(model_id, model_name) and is served by the matching descending index.
+"""
+
+from __future__ import annotations
+
+import json
+from collections.abc import Sequence
+from datetime import datetime, timezone
+from typing import TYPE_CHECKING, Final
+
+from pydantic import BaseModel, ConfigDict, JsonValue, TypeAdapter, field_validator
+
+from litellm._logging import verbose_proxy_logger
+
+if TYPE_CHECKING:
+    from litellm.proxy.utils import PrismaClient
+
+LATEST_HEALTH_CHECKS_SQL: Final = """
+SELECT DISTINCT ON ("model_id", "model_name")
+       "health_check_id", "model_name", "model_id", "status",
+       "healthy_count", "unhealthy_count", "error_message",
+       "response_time_ms", "details", "checked_by",
+       "checked_at", "created_at", "updated_at"
+FROM "LiteLLM_HealthCheckTable"
+ORDER BY "model_id" ASC, "model_name" ASC, "checked_at" DESC
+"""
+
+LATEST_HEALTH_CHECKS_FOR_MODELS_SQL: Final = """
+SELECT DISTINCT ON ("model_id", "model_name")
+       "health_check_id", "model_name", "model_id", "status",
+       "healthy_count", "unhealthy_count", "error_message",
+       "response_time_ms", "details", "checked_by",
+       "checked_at", "created_at", "updated_at"
+FROM "LiteLLM_HealthCheckTable"
+WHERE "model_name" = ANY($1)
+ORDER BY "model_id" ASC, "model_name" ASC, "checked_at" DESC
+"""
+
+
+class LatestHealthCheckRow(BaseModel):
+    model_config = ConfigDict(frozen=True, protected_namespaces=())
+
+    health_check_id: str
+    model_name: str
+    model_id: str | None = None
+    status: str
+    healthy_count: int = 0
+    unhealthy_count: int = 0
+    error_message: str | None = None
+    response_time_ms: float | None = None
+    details: JsonValue | None = None
+    checked_by: str | None = None
+    checked_at: datetime
+    created_at: datetime
+    updated_at: datetime
+
+    @field_validator("details", mode="before")
+    @classmethod
+    def _decode_json_text(cls, value: object) -> object:
+        return json.loads(value) if isinstance(value, str) else value
+
+    @field_validator("checked_at", "created_at", "updated_at")
+    @classmethod
+    def _assume_utc(cls, value: datetime) -> datetime:
+        return value.replace(tzinfo=timezone.utc) if value.tzinfo is None else value
+
+
+_ROWS_ADAPTER: Final = TypeAdapter(tuple[LatestHealthCheckRow, ...])
+
+
+async def fetch_latest_health_checks(prisma_client: PrismaClient) -> tuple[LatestHealthCheckRow, ...]:
+    try:
+        rows: Final = await prisma_client.db.query_raw(LATEST_HEALTH_CHECKS_SQL)
+        return _ROWS_ADAPTER.validate_python(rows)
+    except Exception as query_err:  # noqa: BLE001  # health decorates other reads; a driver error must not fail them
+        verbose_proxy_logger.error("Error getting all latest health checks: %s", query_err)
+        return ()
+
+
+async def fetch_latest_health_checks_for_models(
+    prisma_client: PrismaClient, model_names: Sequence[str]
+) -> tuple[LatestHealthCheckRow, ...]:
+    if not model_names:
+        return ()
+    try:
+        rows: Final = await prisma_client.db.query_raw(LATEST_HEALTH_CHECKS_FOR_MODELS_SQL, list(model_names))
+        return _ROWS_ADAPTER.validate_python(rows)
+    except Exception as query_err:  # noqa: BLE001  # a paged model list must not fail on its health decoration
+        verbose_proxy_logger.error("Error getting latest health checks for models: %s", query_err)
+        return ()
diff --git a/litellm/proxy/db/pgbouncer.py b/litellm/proxy/db/pgbouncer.py
new file mode 100644
index 00000000000..c9fbabd3585
--- /dev/null
+++ b/litellm/proxy/db/pgbouncer.py
@@ -0,0 +1,743 @@
+"""In-container PgBouncer shared by every proxy worker.
+
+Each uvicorn worker owns a Prisma query engine with its own pool of
+``connection_limit`` server connections, so the connections a pod holds open
+against Postgres scale as ``workers * connection_limit`` and a database with a
+fixed connection ceiling runs out of room as pods and workers are added.
+
+When ``LITELLM_PGBOUNCER_ENABLED`` is set, the supervisor process starts one
+PgBouncer next to the workers (no extra network hop: it listens on loopback
+inside the pod) in transaction pooling mode, points ``DATABASE_URL`` at it
+with ``pgbouncer=true`` so Prisma stops using server-side prepared statements,
+and keeps it running for the life of the proxy. Every worker's pool then
+becomes cheap client connections to PgBouncer while the upstream connection
+count is capped at ``LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS`` per pod, no matter
+how many workers run.
+
+Migrations and the schema diff run in the supervisor before the pooler is
+started, so they always go straight to Postgres. ``DATABASE_URL_READ_REPLICA``
+is left untouched.
+
+The workers never hold the upstream credential: they log in to PgBouncer as
+``litellm_pgbouncer`` with a random password made at startup, and PgBouncer
+takes the database user's password from its auth file. Under
+``IAM_TOKEN_DB_AUTH`` or ``AZURE_POSTGRESQL_AUTH`` that password is a
+short-lived token, so the supervisor mints a new one before it expires,
+rewrites the auth file and asks PgBouncer to reload; only new upstream
+connections authenticate, so live ones are unaffected. The pooled
+``DATABASE_URL`` then carries a static password, and the workers must not run
+their own token refresh against it: ``LITELLM_PGBOUNCER_POOLED_DATABASE_URL``
+tells them so, while a read replica keeps refreshing its own token.
+"""
+
+from __future__ import annotations
+
+import atexit
+import functools
+import os
+import re
+import secrets
+import shlex
+import shutil
+import signal
+import socket
+import subprocess
+import tempfile
+import threading
+import time
+import urllib.parse
+from collections.abc import Callable, Mapping, Sequence
+from dataclasses import dataclass
+from datetime import datetime, timezone
+from pathlib import Path
+from types import MappingProxyType
+from typing import Final
+
+from pydantic import Field
+from pydantic_settings import BaseSettings, SettingsConfigDict
+
+from litellm._logging import verbose_proxy_logger
+from litellm.proxy.db.token_auth import (
+    DatabaseTokenAuth,
+    IAMEndpoint,
+    mint_database_token,
+    parse_database_token_expiration,
+    parse_iam_endpoint_from_url,
+)
+
+PGBOUNCER_ENV_PREFIX: Final = "LITELLM_PGBOUNCER_"
+PGBOUNCER_POOLED_ENV_VAR: Final = "LITELLM_PGBOUNCER_POOLED_DATABASE_URL"
+PGBOUNCER_LISTEN_ADDR: Final = "127.0.0.1"
+PGBOUNCER_POOL_USER: Final = "litellm_pgbouncer"
+PGBOUNCER_INI_NAME: Final = "pgbouncer.ini"
+PGBOUNCER_USERLIST_NAME: Final = "userlist.txt"
+PGBOUNCER_CA_NAME: Final = "server-ca.pem"
+PGBOUNCER_RESTART_DELAY_SECONDS: Final = 1.0
+PGBOUNCER_READY_TIMEOUT_SECONDS: Final = 15.0
+PGBOUNCER_STOP_GRACE_SECONDS: Final = 10.0
+PGBOUNCER_UNPRIVILEGED_USER: Final = "nobody"
+PGBOUNCER_MIN_VERSION: Final = (1, 19)
+PGBOUNCER_MAX_PASSWORD_BYTES: Final = 2048
+PGBOUNCER_VERSION_PATTERN: Final = re.compile(r"PgBouncer (\d+)\.(\d+)")
+PGBOUNCER_TOKEN_REFRESH_BUFFER_SECONDS: Final = 180.0
+PGBOUNCER_TOKEN_FALLBACK_REFRESH_SECONDS: Final = 600.0
+PGBOUNCER_TOKEN_RETRY_SECONDS: Final = 30.0
+
+# Prisma's client-side TLS params describe the hop to Postgres, which becomes
+# PgBouncer's server side. They move into ``server_tls_*`` and must not stay on
+# the loopback URL: the listener speaks plain TCP and Prisma would refuse it
+# under ``sslmode=require`` or ``channel_binding=require``.
+PRISMA_TLS_PARAM_KEYS: Final[frozenset[str]] = frozenset(
+    {"sslmode", "sslcert", "sslaccept", "sslidentity", "sslpassword", "channel_binding", "gssencmode"}
+)
+POOLED_URL_DROPPED_KEYS: Final[frozenset[str]] = PRISMA_TLS_PARAM_KEYS | frozenset(("options", "pgbouncer"))
+PGBOUNCER_SSLMODES: Final[frozenset[str]] = frozenset(
+    {"disable", "allow", "prefer", "require", "verify-ca", "verify-full"}
+)
+
+
+class PgBouncerSettings(BaseSettings):
+    """``LITELLM_PGBOUNCER_*`` env vars, read once in the supervisor."""
+
+    model_config = SettingsConfigDict(
+        env_prefix=PGBOUNCER_ENV_PREFIX, case_sensitive=False, extra="ignore", frozen=True
+    )
+
+    enabled: bool = False
+    port: int = Field(default=6432, ge=1, le=65535)
+    max_db_connections: int = Field(default=20, ge=1)
+    max_client_conn: int = Field(default=1000, ge=1)
+    binary: str = "pgbouncer"
+
+
+@dataclass(frozen=True, slots=True)
+class PgBouncerPlan:
+    ini: str
+    pooled_url: str
+    upstream_user: str
+    upstream_password: str | None
+    pool_password: str
+    ca_source: str | None = None
+
+    def userlist(self, upstream_password: str) -> str:
+        return "".join(
+            f"{_userlist_quote(user)} {_userlist_quote(password)}\n"
+            for user, password in ((self.upstream_user, upstream_password), (PGBOUNCER_POOL_USER, self.pool_password))
+        )
+
+
+@dataclass(frozen=True, slots=True)
+class PgBouncerError:
+    reason: str
+
+
+def _single_quoted(value: str) -> str:
+    """Quote for SQL and for PgBouncer's ``[databases]`` connection string: both double a literal ``'``."""
+    return "'" + value.replace("'", "''") + "'"
+
+
+def _userlist_quote(value: str) -> str:
+    return '"' + value.replace('"', '""') + '"'
+
+
+def _option_settings(tokens: Sequence[str]) -> tuple[str, ...] | None:
+    """The ``name=value`` settings in a libpq ``options`` string, or None if it holds anything else.
+
+    Accepts ``-c name=value``, ``-cname=value`` and ``--name=value``; a
+    detached ``-c`` is folded into the token that follows it first.
+    """
+    folded: Final = tuple(
+        f"-c{tokens[index + 1]}" if token == "-c" and index + 1 < len(tokens) else token
+        for index, token in enumerate(tokens)
+        if index == 0 or tokens[index - 1] != "-c"
+    )
+    settings: Final = tuple(token[2:] for token in folded if token.startswith(("-c", "--")) and "=" in token[2:])
+    return settings if len(settings) == len(folded) else None
+
+
+def _connect_query(options: str) -> str | PgBouncerError:
+    """Turn Prisma's ``options=-c name=value ...`` startup param into ``SET`` statements.
+
+    PgBouncer rejects any ``-c`` setting in ``options`` that is not one of the
+    handful it tracks (``statement_timeout`` and ``lock_timeout`` are not), so
+    the settings are applied to each new server connection instead. Every
+    client shares them, which is what the single ``DATABASE_URL`` gave anyway.
+    """
+    settings: Final = _option_settings(tuple(shlex.split(options)))
+    if settings is None:
+        return PgBouncerError(f"cannot translate the DATABASE_URL options {options!r} into PgBouncer settings")
+    return "; ".join(
+        f"SET {name.strip()} TO {_single_quoted(value.strip())}"
+        for name, value in (setting.split("=", 1) for setting in settings)
+    )
+
+
+def _server_tls_settings(sslmode: str, sslcert: str, sslaccept: str, ca_path: Path) -> tuple[str, ...] | PgBouncerError:
+    """``server_tls_*`` lines naming ``ca_path``, the runtime-dir copy of the bundle: the original (or the
+    0600 root pinned by ``pin_bundle_root``) is often unreadable for the user PgBouncer drops to."""
+    if sslmode not in PGBOUNCER_SSLMODES:
+        return PgBouncerError(f"unsupported sslmode {sslmode!r} on DATABASE_URL")
+    verify: Final = sslmode in ("verify-ca", "verify-full") or (sslmode == "require" and sslaccept == "strict")
+    if verify and not sslcert:
+        return PgBouncerError(
+            "DATABASE_URL asks for a verified TLS connection but names no CA bundle; "
+            "add sslcert=<ca.pem> (or sslrootcert=) so the in-container PgBouncer can verify Postgres"
+        )
+    mode: Final = "verify-full" if verify else sslmode
+    return (f"server_tls_sslmode = {mode}", *((f"server_tls_ca_file = {ca_path}",) if sslcert else ()))
+
+
+def plan_pgbouncer(
+    upstream_url: str,
+    settings: PgBouncerSettings,
+    runtime_dir: Path,
+    run_as_user: str | None,
+) -> PgBouncerPlan | PgBouncerError:
+    """Render the PgBouncer config for ``upstream_url`` and the loopback URL Prisma uses instead.
+
+    Params describing Prisma's own pool (``connection_limit``, ``pool_timeout``,
+    ...) stay on the pooled URL; the TLS params and ``options`` describe the hop
+    to Postgres and move into the PgBouncer config. The upstream password is
+    left out of the config on purpose: PgBouncer then takes it from the auth
+    file, which can be rewritten while it runs. ``run_as_user`` is the
+    unprivileged user PgBouncer drops to when the proxy runs as root, which
+    PgBouncer itself refuses to do.
+    """
+    parsed: Final = urllib.parse.urlsplit(upstream_url)
+    params: Final[Mapping[str, str]] = MappingProxyType(
+        dict(urllib.parse.parse_qsl(parsed.query, keep_blank_values=True))
+    )
+    dbname: Final = urllib.parse.unquote(parsed.path.lstrip("/"))
+    username: Final = urllib.parse.unquote(parsed.username or "")
+    password: Final = None if parsed.password is None else urllib.parse.unquote(parsed.password)
+    if not parsed.hostname or not username or not dbname:
+        return PgBouncerError("DATABASE_URL must carry a host, user and database name for the in-container PgBouncer")
+    if username == PGBOUNCER_POOL_USER:
+        return PgBouncerError(
+            f"the database user cannot be named {PGBOUNCER_POOL_USER!r}: that is the user the workers log in to the "
+            "in-container PgBouncer as, and PgBouncer keeps one password per user"
+        )
+    if "sslidentity" in params:
+        return PgBouncerError("client certificates (sslidentity) are not supported with the in-container PgBouncer")
+    tls: Final = _server_tls_settings(
+        params.get("sslmode", "prefer"),
+        params.get("sslcert", ""),
+        params.get("sslaccept", ""),
+        runtime_dir / PGBOUNCER_CA_NAME,
+    )
+    if isinstance(tls, PgBouncerError):
+        return tls
+    connect_query: Final = _connect_query(params["options"]) if params.get("options") else ""
+    if isinstance(connect_query, PgBouncerError):
+        return connect_query
+    upstream: Final = " ".join(
+        (
+            f"host={_single_quoted(parsed.hostname)}",
+            f"port={parsed.port or 5432}",
+            f"dbname={_single_quoted(dbname)}",
+            f"user={_single_quoted(username)}",
+            *((f"connect_query={_single_quoted(connect_query)}",) if connect_query else ()),
+        )
+    )
+    ini: Final = "\n".join(
+        (
+            "[databases]",
+            f"{dbname} = {upstream}",
+            "",
+            "[pgbouncer]",
+            f"listen_addr = {PGBOUNCER_LISTEN_ADDR}",
+            f"listen_port = {settings.port}",
+            f"unix_socket_dir = {runtime_dir}",
+            f"auth_file = {runtime_dir / PGBOUNCER_USERLIST_NAME}",
+            "auth_type = scram-sha-256",
+            f"stats_users = {PGBOUNCER_POOL_USER}",
+            "pool_mode = transaction",
+            f"max_client_conn = {settings.max_client_conn}",
+            f"default_pool_size = {settings.max_db_connections}",
+            f"max_db_connections = {settings.max_db_connections}",
+            "ignore_startup_parameters = extra_float_digits",
+            *tls,
+            *((f"user = {run_as_user}",) if run_as_user else ()),
+            "",
+        )
+    )
+    pooled_query: Final = urllib.parse.urlencode(
+        (*((key, value) for key, value in params.items() if key not in POOLED_URL_DROPPED_KEYS), ("pgbouncer", "true"))
+    )
+    pool_password: Final = secrets.token_urlsafe(32)
+    pooled_url: Final = urllib.parse.urlunsplit(
+        parsed._replace(
+            netloc=f"{PGBOUNCER_POOL_USER}:{pool_password}@{PGBOUNCER_LISTEN_ADDR}:{settings.port}", query=pooled_query
+        )
+    )
+    return PgBouncerPlan(
+        ini=ini,
+        pooled_url=pooled_url,
+        upstream_user=username,
+        upstream_password=password,
+        pool_password=pool_password,
+        ca_source=params.get("sslcert") or None,
+    )
+
+
+def pooled_database_url(upstream_url: str, settings: PgBouncerSettings) -> str | PgBouncerError:
+    """The loopback URL of a PgBouncer another container in the pod already runs for ``upstream_url``.
+
+    Only the container that started PgBouncer knows the pool user's password, so
+    this logs in as the upstream user, whom the auth file lists as well.
+    """
+    plan: Final = plan_pgbouncer(upstream_url, settings, runtime_dir=Path("/nonexistent"), run_as_user=None)
+    if isinstance(plan, PgBouncerError):
+        return plan
+    password: Final = urllib.parse.urlsplit(upstream_url).password or ""
+    credentials: Final = f"{urllib.parse.quote(plan.upstream_user, safe='')}:{password}"
+    return urllib.parse.urlunsplit(
+        urllib.parse.urlsplit(plan.pooled_url)._replace(netloc=f"{credentials}@{PGBOUNCER_LISTEN_ADDR}:{settings.port}")
+    )
+
+
+def _write_private(path: Path, content: str, run_as_user: str | None) -> None:
+    with open(os.open(path, os.O_WRONLY | os.O_CREAT | os.O_TRUNC, 0o600), "w", encoding="utf-8") as handle:
+        handle.write(content)
+    if run_as_user is not None:
+        shutil.chown(path, user=run_as_user)
+
+
+def write_pgbouncer_ini(plan: PgBouncerPlan, runtime_dir: Path, run_as_user: str | None) -> Path | PgBouncerError:
+    """Write the ini (mode 0600) and the CA copy, and return the ini path.
+
+    ``run_as_user`` is the user PgBouncer drops to when started as root; it has
+    to own the files it re-reads on reload and the socket directory.
+    """
+    ini_path: Final = runtime_dir / PGBOUNCER_INI_NAME
+    ca_path: Final = runtime_dir / PGBOUNCER_CA_NAME
+    if plan.ca_source is not None:
+        try:
+            shutil.copyfile(plan.ca_source, ca_path)
+        except OSError as error:
+            return PgBouncerError(f"cannot read the CA bundle {plan.ca_source!r} named by sslcert: {error}")
+    _write_private(ini_path, plan.ini, run_as_user)
+    if run_as_user is not None:
+        runtime_dir.chmod(0o700)
+        for path in (runtime_dir, *((ca_path,) if plan.ca_source is not None else ())):
+            shutil.chown(path, user=run_as_user)
+    return ini_path
+
+
+def write_userlist(userlist: str, runtime_dir: Path, run_as_user: str | None) -> Path:
+    """Replace the auth file in one step, so a PgBouncer starting or reloading meanwhile reads the old or the new one whole."""
+    userlist_path: Final = runtime_dir / PGBOUNCER_USERLIST_NAME
+    staged_path: Final = runtime_dir / f".{PGBOUNCER_USERLIST_NAME}.next"
+    _write_private(staged_path, userlist, run_as_user)
+    os.replace(staged_path, userlist_path)
+    return userlist_path
+
+
+def export_pooled_database_url(pooled_url: str) -> None:
+    os.environ["DATABASE_URL"] = pooled_url
+    os.environ[PGBOUNCER_POOLED_ENV_VAR] = "true"
+
+
+def database_url_is_pooled(environ: Mapping[str, str] = os.environ) -> bool:
+    return environ.get(PGBOUNCER_POOLED_ENV_VAR) == "true"
+
+
+@dataclass(frozen=True, slots=True)
+class PgBouncerTokenSource:
+    auth: DatabaseTokenAuth
+    endpoint: IAMEndpoint
+
+    def mint(self) -> str:
+        """The token as Postgres expects it: ``mint_database_token`` returns it percent-encoded for a URL."""
+        return urllib.parse.unquote(mint_database_token(self.auth, self.endpoint))
+
+    def expires_at(self, token: str) -> datetime | None:
+        return parse_database_token_expiration(self.auth, token)
+
+
+def _utcnow() -> datetime:
+    return datetime.now(timezone.utc).replace(tzinfo=None)
+
+
+class PgBouncerTokenRefresher:
+    """Keeps the token in PgBouncer's auth file current from a daemon thread.
+
+    ``install`` gets each fresh token and is expected to rewrite the auth file
+    and reload PgBouncer. The next refresh is due ``buffer_seconds`` before the
+    token expires, or ``fallback_seconds`` later when the expiry cannot be read.
+    A refresh that fails leaves the previous auth file in place and is retried
+    after ``retry_seconds``: the old token stays good until it expires, so a
+    transient credential-provider error costs nothing unless it persists.
+    """
+
+    def __init__(
+        self,
+        source: PgBouncerTokenSource,
+        install: Callable[[str], None],
+        *,
+        buffer_seconds: float = PGBOUNCER_TOKEN_REFRESH_BUFFER_SECONDS,
+        fallback_seconds: float = PGBOUNCER_TOKEN_FALLBACK_REFRESH_SECONDS,
+        retry_seconds: float = PGBOUNCER_TOKEN_RETRY_SECONDS,
+        now: Callable[[], datetime] = _utcnow,
+    ) -> None:
+        self._source: Final = source
+        self._install: Final = install
+        self._buffer_seconds: Final = buffer_seconds
+        self._fallback_seconds: Final = fallback_seconds
+        self._retry_seconds: Final = retry_seconds
+        self._now: Final = now
+        self._stopping: Final = threading.Event()
+        self._delay: float = 0.0
+        self._thread: threading.Thread | None = None
+
+    def refresh(self) -> float | PgBouncerError:
+        label: Final = self._source.auth.label
+        try:
+            token: Final = self._source.mint()
+        except Exception as mint_error:
+            return PgBouncerError(f"could not mint a {label} for the in-container pgbouncer: {mint_error!r}")
+        if len(token.encode()) >= PGBOUNCER_MAX_PASSWORD_BYTES:
+            return PgBouncerError(
+                f"the {label} is {len(token.encode())} bytes long, but PgBouncer's auth file holds passwords of at "
+                f"most {PGBOUNCER_MAX_PASSWORD_BYTES - 1} bytes"
+            )
+        try:
+            self._install(token)
+        except OSError as install_error:
+            return PgBouncerError(f"could not install the {label} into the pgbouncer auth file: {install_error}")
+        expires_at: Final = self._source.expires_at(token)
+        if expires_at is None:
+            return self._fallback_seconds
+        return max(self._retry_seconds, (expires_at - self._now()).total_seconds() - self._buffer_seconds)
+
+    def start(self) -> PgBouncerError | None:
+        primed: Final = self.refresh()
+        if isinstance(primed, PgBouncerError):
+            return primed
+        self._delay = primed
+        self._thread = threading.Thread(target=self._run, daemon=True, name="litellm-pgbouncer-token-refresh")
+        self._thread.start()
+        return None
+
+    def _run(self) -> None:
+        while not self._stopping.wait(self._delay):
+            self._delay = self._refresh_and_report()
+
+    def _refresh_and_report(self) -> float:
+        outcome: Final = self.refresh()
+        if isinstance(outcome, PgBouncerError):
+            verbose_proxy_logger.error(
+                "In-container pgbouncer keeps its current %s (%s); retrying in %.0fs.",
+                self._source.auth.label,
+                outcome.reason,
+                self._retry_seconds,
+            )
+            return self._retry_seconds
+        verbose_proxy_logger.info(
+            "In-container pgbouncer picked up a fresh %s; the next one is due in %.0fs.",
+            self._source.auth.label,
+            outcome,
+        )
+        return outcome
+
+    def stop(self) -> None:
+        self._stopping.set()
+        if self._thread is not None:
+            self._thread.join()
+
+
+def _port_open(port: int) -> bool:
+    try:
+        with socket.create_connection((PGBOUNCER_LISTEN_ADDR, port), timeout=0.5):
+            return True
+    except OSError:
+        return False
+
+
+def _unix_socket_open(path: Path) -> bool:
+    with socket.socket(socket.AF_UNIX) as probe:
+        probe.settimeout(0.5)
+        try:
+            probe.connect(str(path))
+        except OSError:
+            return False
+        return True
+
+
+def unix_socket_path(runtime_dir: Path, port: int) -> Path:
+    return runtime_dir / f".s.PGSQL.{port}"
+
+
+def pgbouncer_version(binary: str) -> tuple[int, int] | PgBouncerError:
+    """``(major, minor)`` from ``<binary> --version``.
+
+    Readiness relies on PgBouncer exiting when it cannot bind its TCP port,
+    which it does from 1.19 on. Older releases log a warning and serve the unix
+    socket alone, so their socket would vouch for a port held by someone else.
+    """
+    try:
+        output: Final = subprocess.run(
+            (binary, "--version"), capture_output=True, text=True, check=False, timeout=10
+        ).stdout
+    except (OSError, subprocess.TimeoutExpired) as run_error:
+        return PgBouncerError(f"could not run {binary!r} --version: {run_error}")
+    found: Final = PGBOUNCER_VERSION_PATTERN.search(output)
+    if found is None:
+        return PgBouncerError(f"{binary!r} --version did not report a PgBouncer version: {output.strip()!r}")
+    return int(found[1]), int(found[2])
+
+
+def _end(process: subprocess.Popen[bytes]) -> None:
+    if process.poll() is not None:
+        return
+    process.terminate()
+    try:
+        process.wait(timeout=PGBOUNCER_STOP_GRACE_SECONDS)
+    except subprocess.TimeoutExpired:
+        process.kill()
+        process.wait()
+
+
+class PgBouncerProcess:
+    """Runs ``argv`` as a foreground child and restarts it whenever it exits on its own.
+
+    Prisma reconnects by itself after a failed query, so a PgBouncer crash
+    costs the requests in flight plus one failed query per idle pooled
+    connection the crash severed, and nothing else once the replacement is
+    listening again. A replacement that cannot be spawned, finds its port
+    taken, exits again or never starts listening is retried every
+    ``restart_delay_seconds`` until ``stop`` is called.
+
+    A connect probe of ``port`` cannot tell the child from another process
+    that grabbed the port after the availability check, so readiness also
+    needs ``socket_path``: the unix socket PgBouncer creates in the private
+    runtime directory, which it only does once every TCP listener is bound
+    (PgBouncer 1.19 or newer, see ``pgbouncer_version``).
+    """
+
+    def __init__(
+        self,
+        argv: Sequence[str],
+        port: int,
+        socket_path: Path,
+        restart_delay_seconds: float = PGBOUNCER_RESTART_DELAY_SECONDS,
+        ready_timeout_seconds: float = PGBOUNCER_READY_TIMEOUT_SECONDS,
+    ) -> None:
+        self.argv: Final = tuple(argv)
+        self.port: Final = port
+        self.socket_path: Final = socket_path
+        self.restart_delay_seconds: Final = restart_delay_seconds
+        self.ready_timeout_seconds: Final = ready_timeout_seconds
+        self._stopping: Final = threading.Event()
+        self._lock: Final = threading.Lock()
+        self._process: subprocess.Popen[bytes] | None = None
+
+    @property
+    def pid(self) -> int | None:
+        with self._lock:
+            return None if self._process is None else self._process.pid
+
+    def _spawn(self) -> subprocess.Popen[bytes] | PgBouncerError | None:
+        """Start a child, or None once ``stop`` ran; both take the lock so no child can slip in after a stop.
+
+        The port has to be free first: a listener that is already there would
+        pass the readiness check while the child fails to bind.
+        """
+        with self._lock:
+            if self._stopping.is_set():
+                return None
+            if _port_open(self.port):
+                return PgBouncerError(f"{PGBOUNCER_LISTEN_ADDR}:{self.port} is already in use by another process")
+            try:
+                process: Final = subprocess.Popen(self.argv)
+            except OSError as spawn_error:
+                return PgBouncerError(f"could not start {self.argv[0]!r}: {spawn_error}")
+            self._process = process
+            return process
+
+    def _wait_ready(self, process: subprocess.Popen[bytes]) -> PgBouncerError | None:
+        deadline: Final = time.monotonic() + self.ready_timeout_seconds
+        while time.monotonic() < deadline:
+            if process.poll() is not None:
+                return PgBouncerError(f"pgbouncer exited with status {process.returncode} during startup")
+            if _port_open(self.port) and _unix_socket_open(self.socket_path):
+                return None
+            time.sleep(0.1)
+        if _port_open(self.port):
+            return PgBouncerError(
+                f"{PGBOUNCER_LISTEN_ADDR}:{self.port} is served by another process, not the pgbouncer that was started"
+            )
+        return PgBouncerError(
+            f"pgbouncer did not start listening on {PGBOUNCER_LISTEN_ADDR}:{self.port} "
+            f"within {self.ready_timeout_seconds:.0f}s"
+        )
+
+    def start(self) -> PgBouncerError | None:
+        """Spawn PgBouncer, wait until it listens on port and unix socket, then supervise it from a daemon thread."""
+        process: Final = self._spawn()
+        if process is None:
+            return PgBouncerError("pgbouncer was stopped before it started")
+        if isinstance(process, PgBouncerError):
+            return process
+        not_ready: Final = self._wait_ready(process)
+        if not_ready is not None:
+            self.stop()
+            return not_ready
+        self._watch(process)
+        return None
+
+    def _watch(self, process: subprocess.Popen[bytes]) -> None:
+        threading.Thread(
+            target=self._supervise, args=(process,), daemon=True, name="litellm-pgbouncer-supervisor"
+        ).start()
+
+    def _supervise(self, process: subprocess.Popen[bytes]) -> None:
+        status: Final = process.wait()
+        if self._stopping.is_set():
+            return
+        verbose_proxy_logger.error(
+            "In-container pgbouncer (pid %s) exited with status %s; restarting in %.1fs.",
+            process.pid,
+            status,
+            self.restart_delay_seconds,
+        )
+        self._restart_after_delay()
+
+    def _restart_after_delay(self) -> None:
+        time.sleep(self.restart_delay_seconds)
+        process: Final = self._spawn()
+        if process is None:
+            return
+        if isinstance(process, PgBouncerError):
+            self._retry_restart(process.reason)
+            return
+        not_ready: Final = self._wait_ready(process)
+        if not_ready is None:
+            self._watch(process)
+            return
+        _end(process)
+        self._retry_restart(not_ready.reason)
+
+    def _retry_restart(self, reason: str) -> None:
+        if self._stopping.is_set():
+            return
+        verbose_proxy_logger.error(
+            "In-container pgbouncer could not be restarted (%s); retrying in %.1fs.", reason, self.restart_delay_seconds
+        )
+        threading.Thread(target=self._restart_after_delay, daemon=True, name="litellm-pgbouncer-supervisor").start()
+
+    def reload(self) -> None:
+        with self._lock:
+            if self._process is not None:
+                self._process.send_signal(signal.SIGHUP)
+
+    def stop(self) -> None:
+        with self._lock:
+            self._stopping.set()
+            process: Final = self._process
+        if process is not None:
+            _end(process)
+
+
+def install_pgbouncer_token(
+    plan: PgBouncerPlan, runtime_dir: Path, run_as_user: str | None, pooler: PgBouncerProcess, token: str
+) -> None:
+    write_userlist(plan.userlist(token), runtime_dir, run_as_user)
+    pooler.reload()
+
+
+def _install_upstream_password(
+    plan: PgBouncerPlan,
+    runtime_dir: Path,
+    run_as_user: str | None,
+    pooler: PgBouncerProcess,
+    token_auth: DatabaseTokenAuth | None,
+    upstream_url: str,
+) -> PgBouncerTokenRefresher | None | PgBouncerError:
+    if token_auth is None:
+        if plan.upstream_password is None:
+            return PgBouncerError(
+                "DATABASE_URL carries no password and neither IAM_TOKEN_DB_AUTH nor AZURE_POSTGRESQL_AUTH is on, "
+                "so the in-container PgBouncer has nothing to authenticate to Postgres with"
+            )
+        write_userlist(plan.userlist(plan.upstream_password), runtime_dir, run_as_user)
+        return None
+    refresher: Final = PgBouncerTokenRefresher(
+        PgBouncerTokenSource(auth=token_auth, endpoint=parse_iam_endpoint_from_url(upstream_url)),
+        functools.partial(install_pgbouncer_token, plan, runtime_dir, run_as_user, pooler),
+    )
+    failed: Final = refresher.start()
+    if failed is not None:
+        return failed
+    return refresher
+
+
+def _only_in_this_process(action: Callable[[], None]) -> Callable[[], None]:
+    """An exit hook that does nothing in a forked child, which inherits the parent's ``atexit`` table."""
+    owner_pid: Final = os.getpid()
+
+    def run() -> None:
+        if os.getpid() == owner_pid:
+            action()
+
+    return run
+
+
+def start_in_container_pgbouncer(
+    settings: PgBouncerSettings,
+    upstream_url: str,
+    token_auth: DatabaseTokenAuth | None = None,
+    register_exit_hook: Callable[[Callable[[], None]], object] = atexit.register,
+) -> str | PgBouncerError:
+    """Start the pooler for ``upstream_url`` and return the loopback URL the workers must use.
+
+    The pooler lives as long as this process: it is stopped from the exit hooks
+    once the worker manager has returned, and only by the process that started
+    it (gunicorn forks its workers, so they carry the hooks too). PgBouncer
+    refuses to run as root, so a root proxy (the default image) has it drop to
+    ``nobody``. With ``token_auth`` the password on ``upstream_url`` is ignored:
+    the pooler mints its own tokens and renews them for as long as it runs.
+    """
+    version: Final = pgbouncer_version(settings.binary)
+    if isinstance(version, PgBouncerError):
+        return version
+    if version < PGBOUNCER_MIN_VERSION:
+        return PgBouncerError(
+            f"PgBouncer {version[0]}.{version[1]} keeps running after failing to bind its TCP port, so the proxy "
+            f"cannot tell it apart from another listener; {PGBOUNCER_MIN_VERSION[0]}.{PGBOUNCER_MIN_VERSION[1]} "
+            "or newer is required"
+        )
+    runtime_dir: Final = Path(tempfile.mkdtemp(prefix="litellm-pgbouncer-"))
+    register_exit_hook(_only_in_this_process(lambda: shutil.rmtree(runtime_dir, ignore_errors=True)))
+    run_as_user: Final = PGBOUNCER_UNPRIVILEGED_USER if os.geteuid() == 0 else None
+    plan: Final = plan_pgbouncer(upstream_url, settings, runtime_dir, run_as_user)
+    if isinstance(plan, PgBouncerError):
+        return plan
+    ini_path: Final = write_pgbouncer_ini(plan, runtime_dir, run_as_user)
+    if isinstance(ini_path, PgBouncerError):
+        return ini_path
+    pooler: Final = PgBouncerProcess(
+        argv=(settings.binary, str(ini_path)),
+        port=settings.port,
+        socket_path=unix_socket_path(runtime_dir, settings.port),
+    )
+    refresher: Final = _install_upstream_password(plan, runtime_dir, run_as_user, pooler, token_auth, upstream_url)
+    if isinstance(refresher, PgBouncerError):
+        return refresher
+    failed: Final = pooler.start()
+    if failed is not None:
+        if refresher is not None:
+            refresher.stop()
+        return failed
+    register_exit_hook(_only_in_this_process(pooler.stop))
+    if refresher is not None:
+        register_exit_hook(_only_in_this_process(refresher.stop))
+    verbose_proxy_logger.info(
+        "In-container pgbouncer (pid %s) listening on %s:%s; capping this pod at %s upstream database connections%s.",
+        pooler.pid,
+        PGBOUNCER_LISTEN_ADDR,
+        settings.port,
+        settings.max_db_connections,
+        "" if token_auth is None else f" and renewing its {token_auth.label} before each one expires",
+    )
+    return plan.pooled_url
diff --git a/litellm/proxy/db/spend_counter_reseed.py b/litellm/proxy/db/spend_counter_reseed.py
index a38b8a47dbd..e35b1c8c82b 100644
--- a/litellm/proxy/db/spend_counter_reseed.py
+++ b/litellm/proxy/db/spend_counter_reseed.py
@@ -23,6 +23,7 @@ from litellm._logging import verbose_proxy_logger
 from litellm.constants import SPEND_COUNTER_RESEED_LOCKS_MAX_SIZE
 from litellm.litellm_core_utils.duration_parser import duration_in_seconds
 from litellm.proxy._types import Litellm_EntityType
+from litellm.proxy.db.db_lookup_gate import db_lookup_gate
 from litellm.repositories.organization_repository import OrganizationRepository
 from litellm.repositories.table_repositories import (
     BudgetWindowSpendRepository,
@@ -121,30 +122,33 @@ class SpendCounterReseed:
         if SpendCounterReseed._is_key_or_team_window_counter(counter_key):
             return None
         try:
-            if counter_key.startswith("spend:key:"):
-                token: Final = counter_key[len("spend:key:") :]
-                row = await VerificationTokenRepository(prisma_client).table.find_unique(where={"token": token})
-            elif counter_key.startswith("spend:team_member:"):
-                suffix: Final = counter_key[len("spend:team_member:") :]
-                if ":" not in suffix:
+            async with db_lookup_gate.current():
+                if counter_key.startswith("spend:key:"):
+                    token: Final = counter_key[len("spend:key:") :]
+                    row = await VerificationTokenRepository(prisma_client).table.find_unique(where={"token": token})
+                elif counter_key.startswith("spend:team_member:"):
+                    suffix: Final = counter_key[len("spend:team_member:") :]
+                    if ":" not in suffix:
+                        return None
+                    user_id, team_id = suffix.rsplit(":", 1)
+                    row = await TeamMembershipRepository(prisma_client).table.find_unique(
+                        where={"user_id_team_id": {"user_id": user_id, "team_id": team_id}}
+                    )
+                elif counter_key.startswith("spend:team:"):
+                    team_id = counter_key[len("spend:team:") :]
+                    row = await TeamRepository(prisma_client).table.find_unique(where={"team_id": team_id})
+                elif counter_key.startswith("spend:user:"):
+                    user_id = counter_key[len("spend:user:") :]
+                    row = await UserRepository(prisma_client).table.find_unique(where={"user_id": user_id})
+                elif counter_key.startswith(END_USER_COUNTER_PREFIX) or counter_key.startswith("spend:tag:"):
+                    return None
+                elif counter_key.startswith("spend:org:"):
+                    org_id: Final = counter_key[len("spend:org:") :]
+                    row = await OrganizationRepository(prisma_client).table.find_unique(
+                        where={"organization_id": org_id}
+                    )
+                else:
                     return None
-                user_id, team_id = suffix.rsplit(":", 1)
-                row = await TeamMembershipRepository(prisma_client).table.find_unique(
-                    where={"user_id_team_id": {"user_id": user_id, "team_id": team_id}}
-                )
-            elif counter_key.startswith("spend:team:"):
-                team_id = counter_key[len("spend:team:") :]
-                row = await TeamRepository(prisma_client).table.find_unique(where={"team_id": team_id})
-            elif counter_key.startswith("spend:user:"):
-                user_id = counter_key[len("spend:user:") :]
-                row = await UserRepository(prisma_client).table.find_unique(where={"user_id": user_id})
-            elif counter_key.startswith(END_USER_COUNTER_PREFIX) or counter_key.startswith("spend:tag:"):
-                return None
-            elif counter_key.startswith("spend:org:"):
-                org_id: Final = counter_key[len("spend:org:") :]
-                row = await OrganizationRepository(prisma_client).table.find_unique(where={"organization_id": org_id})
-            else:
-                return None
         except Exception:
             verbose_proxy_logger.exception("SpendCounterReseed.from_db: failed for %s", counter_key)
             return None
diff --git a/litellm/proxy/guardrails/auto_router_compression.py b/litellm/proxy/guardrails/auto_router_compression.py
index 98707e7ddca..c37b9fff1f0 100644
--- a/litellm/proxy/guardrails/auto_router_compression.py
+++ b/litellm/proxy/guardrails/auto_router_compression.py
@@ -80,17 +80,19 @@ def policy_from_litellm_params(litellm_params: Mapping[str, object]) -> AutoRout
 def policy_for_model(
     llm_router: "Router | None",
     model_alias: str,
-    team_id: str | None,
+    request_kwargs: Mapping[str, object],
     request_tags: Sequence[str],
 ) -> AutoRouterCompressionPolicy | None:
-    """The compression policy of the auto router marker `model_alias` resolves to.
+    """The compression policy of the auto router marker `model_alias` resolves to for this caller.
 
-    Pre-call arming and the routing hook both resolve through here, so an alias with
-    several tag-scoped markers cannot suppress under one and then route under another.
+    Pre-call arming and the routing hook both resolve through here, and here resolves through the
+    router's own request-scoped deployment lookup, so an alias with several tag-scoped markers
+    cannot suppress under one and then route under another, and a team router reached by its
+    public name carries its policy for every principal that can reach it.
     """
     if llm_router is None:
         return None
-    deployments: Final = llm_router.get_model_list(model_name=model_alias, team_id=team_id) or ()
+    deployments: Final = llm_router.deployments_for_request(model_alias, request_kwargs)
     markers: Final = tuple(
         litellm_params
         for deployment in deployments
@@ -108,17 +110,6 @@ def policy_for_model(
     return next((policy for policy in candidates if policy is not None), None)
 
 
-def team_id_from_request(request_kwargs: Mapping[str, object]) -> str | None:
-    """The caller's team id, from whichever metadata bucket this surface writes to."""
-    for meta_key in ("metadata", "litellm_metadata"):
-        meta = request_kwargs.get(meta_key)
-        if isinstance(meta, Mapping):
-            team_id = meta.get("user_api_key_team_id")
-            if isinstance(team_id, str):
-                return team_id
-    return None
-
-
 def _compression_guardrail_classes() -> tuple[type, ...]:
     """The registered guardrail classes whose provider compresses prompts."""
     from litellm.proxy.guardrails.guardrail_registry import guardrail_class_registry
@@ -172,7 +163,7 @@ async def arm_pre_call(
     policy: Final = policy_for_model(
         llm_router=llm_router,
         model_alias=model_alias,
-        team_id=team_id_from_request(data),
+        request_kwargs=data,
         request_tags=_get_tags_from_request_kwargs(data),
     )
     if policy is None:
diff --git a/litellm/proxy/guardrails/guardrail_hooks/bedrock_guardrails.py b/litellm/proxy/guardrails/guardrail_hooks/bedrock_guardrails.py
index 7204839f6d3..6a7ac4361b9 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/bedrock_guardrails.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/bedrock_guardrails.py
@@ -44,7 +44,7 @@ from litellm.llms.anthropic.chat.guardrail_translation.handler import AnthropicM
 from litellm.llms.base_llm.guardrail_translation.utils import (
     effective_scan_only_tool_results_for_guardrail,
 )
-from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM, bedrock_bearer_token
+from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM, bedrock_bearer_token, run_aws_signing
 from litellm.llms.custom_httpx.http_handler import (
     get_async_httpx_client,
     httpxSpecialProvider,
@@ -917,7 +917,9 @@ class BedrockGuardrail(CustomGuardrail, BaseAWSLLM):
                 source,
             )
             return BedrockGuardrailResponse()
-        credentials, aws_region_name = self._load_credentials(bearer_token=bedrock_bearer_token(api_key))
+        credentials, aws_region_name = await run_aws_signing(
+            self._load_credentials, bearer_token=bedrock_bearer_token(api_key)
+        )
         allow_chunking: Final = not self._content_uses_contextual_grounding(content)
 
         completed_chunk_usages: Final[list[BedrockGuardrailUsage]] = []  # mutable-ok: billed-chunk usage accumulator
@@ -1178,7 +1180,8 @@ class BedrockGuardrail(CustomGuardrail, BaseAWSLLM):
             **base_request_data,
             "content": content,
         }  # mutable-ok: outbound JSON request body
-        prepared_request: Final = self._prepare_request(
+        prepared_request: Final = await run_aws_signing(
+            self._prepare_request,
             credentials=credentials,
             data=bedrock_request_data,
             optional_params=self.optional_params,
@@ -1875,10 +1878,13 @@ class BedrockGuardrail(CustomGuardrail, BaseAWSLLM):
             return BedrockGuardrailResponse()
 
         api_key: Final[str | None] = request_data.get("api_key") if request_data else None
-        credentials, aws_region_name = self._load_credentials(bearer_token=bedrock_bearer_token(api_key))
+        credentials, aws_region_name = await run_aws_signing(
+            self._load_credentials, bearer_token=bedrock_bearer_token(api_key)
+        )
         body: Final[dict[str, object]] = {"messages": checks_messages, "checks": self.checks}
 
-        prepared_request: Final = self._prepare_request(
+        prepared_request: Final = await run_aws_signing(
+            self._prepare_request,
             credentials=credentials,
             data=body,
             optional_params=self.optional_params,
diff --git a/litellm/proxy/guardrails/guardrail_hooks/openai/moderations.py b/litellm/proxy/guardrails/guardrail_hooks/openai/moderations.py
index 10683550f85..c22d35509c1 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/openai/moderations.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/openai/moderations.py
@@ -17,7 +17,8 @@ from litellm.llms.custom_httpx.http_handler import (
     get_async_httpx_client,
     httpxSpecialProvider,
 )
-from litellm.types.guardrails import GuardrailEventHooks
+from litellm.proxy.common_utils.callback_utils import add_guardrail_scan_id
+from litellm.types.guardrails import GuardrailEventHooks, SupportedGuardrailIntegrations
 from litellm.types.utils import (
     GenericGuardrailAPIInputs,
     GuardrailStatus,
@@ -218,6 +219,13 @@ class OpenAIModerationGuardrail(OpenAIGuardrailBase, CustomGuardrail):
             metadata: Final = request_data.get("metadata") or {}
             request_data["metadata"] = metadata
             metadata["_openai_moderation_response"] = moderation_response.model_dump()
+            add_guardrail_scan_id(
+                request_data=request_data,
+                scan_id=moderation_response.id,
+                guardrail_name=self.guardrail_name,
+                provider=SupportedGuardrailIntegrations.OPENAI_MODERATION.value,
+                stage=GuardrailEventHooks.post_call if input_type == "response" else GuardrailEventHooks.pre_call,
+            )
 
         # Check if content is flagged and raise exception if needed
         self._check_moderation_result(moderation_response)
diff --git a/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py b/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py
index b73d3adb99e..3bc0dfabefc 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py
@@ -721,10 +721,18 @@ class PanwPrismaAirsHandler(CustomGuardrail):
             }
         }
 
-    def _record_scan_id(self, request_data: dict[str, object], scan_result: Mapping[str, object]) -> None:
+    def _record_scan_id(
+        self, request_data: dict[str, object], scan_result: Mapping[str, object], stage: GuardrailEventHooks
+    ) -> None:
         """Surface the AIRS scan id on the response, so allowed calls are auditable too."""
         scan_id: Final = scan_result.get("scan_id")
-        add_guardrail_scan_id(request_data=request_data, scan_id=str(scan_id) if scan_id else None)
+        add_guardrail_scan_id(
+            request_data=request_data,
+            scan_id=str(scan_id) if scan_id else None,
+            guardrail_name=self.guardrail_name,
+            provider=self._PROVIDER_NAME,
+            stage=stage,
+        )
 
     def _handle_api_error_with_logging(
         self,
@@ -948,7 +956,7 @@ class PanwPrismaAirsHandler(CustomGuardrail):
             event_type=GuardrailEventHooks.post_call,
         )
         add_guardrail_to_applied_guardrails_header(request_data=request_data, guardrail_name=self.guardrail_name)
-        self._record_scan_id(request_data, scan_result)
+        self._record_scan_id(request_data, scan_result, GuardrailEventHooks.post_call)
 
     def _check_and_mark_scanned(self, data: dict, scan_type: str) -> bool:
         """
@@ -1078,7 +1086,7 @@ class PanwPrismaAirsHandler(CustomGuardrail):
                 duration=(end_time - start_time).total_seconds(),
                 event_type=GuardrailEventHooks.pre_call,
             )
-            self._record_scan_id(data, scan_result)
+            self._record_scan_id(data, scan_result, GuardrailEventHooks.pre_call)
 
             action: Final = scan_result.get("action", "block")
             category: Final = scan_result.get("category", "unknown")
@@ -1199,7 +1207,7 @@ class PanwPrismaAirsHandler(CustomGuardrail):
                 duration=(end_time - start_time).total_seconds(),
                 event_type=GuardrailEventHooks.post_call,
             )
-            self._record_scan_id(data, scan_result)
+            self._record_scan_id(data, scan_result, GuardrailEventHooks.post_call)
 
             action: Final = scan_result.get("action", "block")
             category: Final = scan_result.get("category", "unknown")
@@ -1401,7 +1409,7 @@ class PanwPrismaAirsHandler(CustomGuardrail):
                     duration=(end_time - start_time).total_seconds(),
                     event_type=GuardrailEventHooks.post_call,
                 )
-                self._record_scan_id(request_data, scan_result)
+                self._record_scan_id(request_data, scan_result, GuardrailEventHooks.post_call)
 
                 # Add guardrail to applied guardrails header for observability
                 add_guardrail_to_applied_guardrails_header(
@@ -1475,7 +1483,11 @@ class PanwPrismaAirsHandler(CustomGuardrail):
                 )
                 continue
 
-            self._record_scan_id(request_data, scan_result)
+            self._record_scan_id(
+                request_data,
+                scan_result,
+                GuardrailEventHooks.post_call if is_response else GuardrailEventHooks.pre_call,
+            )
 
             action = scan_result.get("action", "block")
             masked_args = self._masked_tool_call_arguments(
@@ -1829,7 +1841,11 @@ class PanwPrismaAirsHandler(CustomGuardrail):
                 new_texts.append(text)
                 continue
 
-            self._record_scan_id(request_data, scan_result)
+            self._record_scan_id(
+                request_data,
+                scan_result,
+                GuardrailEventHooks.post_call if is_response else GuardrailEventHooks.pre_call,
+            )
 
             action = scan_result.get("action", "block")
             masked_text = self._get_masked_text(scan_result, is_response=is_response)
@@ -1901,7 +1917,7 @@ class PanwPrismaAirsHandler(CustomGuardrail):
                 )
                 # If we reach here, fallback_on_error="allow"
             else:
-                self._record_scan_id(request_data, mcp_scan_result)
+                self._record_scan_id(request_data, mcp_scan_result, GuardrailEventHooks.pre_call)
                 action = mcp_scan_result.get("action", "block")
                 masked_text = self._get_masked_text(mcp_scan_result, is_response=False)
                 if action == "allow":
diff --git a/litellm/proxy/health_endpoints/_health_endpoints.py b/litellm/proxy/health_endpoints/_health_endpoints.py
index 1785a2f0992..bf527e1e868 100644
--- a/litellm/proxy/health_endpoints/_health_endpoints.py
+++ b/litellm/proxy/health_endpoints/_health_endpoints.py
@@ -7,7 +7,7 @@ import secrets
 import time
 import traceback
 from collections.abc import Iterable, Mapping
-from datetime import datetime, timedelta
+from datetime import datetime, timedelta, timezone
 from typing import Any, Final, Literal, TypedDict, cast
 
 import fastapi
@@ -41,6 +41,7 @@ from litellm.proxy.auth.auth_utils import (
 )
 from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
 from litellm.proxy.db.exception_handler import PrismaDBExceptionHandler
+from litellm.proxy.db.health_check_latest import LatestHealthCheckRow
 from litellm.proxy.db.proxy_worker_heartbeat import count_live_proxy_workers
 from litellm.proxy.health_check import (
     ADMIN_ONLY_HEALTH_DISPLAY_PARAMS,
@@ -209,6 +210,7 @@ services = (
         "arize",
         "galileo",
         "newrelic",
+        "pointfive",
         "sqs",
     ]
     | str
@@ -296,6 +298,7 @@ async def health_services_endpoint(
             "arize",
             "galileo",
             "newrelic",
+            "pointfive",
             "sqs",
         ]:
             raise HTTPException(
@@ -320,7 +323,7 @@ async def health_services_endpoint(
             service == "openmeter"
             or service == "braintrust"
             or service == "generic_api"
-            or (service_in_success_callbacks and service != "langfuse")
+            or (service_in_success_callbacks and service not in ("langfuse", "pointfive"))
         ):
             _ = await litellm.acompletion(
                 model="openai/litellm-mock-response-model",
@@ -412,6 +415,27 @@ async def health_services_endpoint(
                 ),
             }
 
+        elif service == "pointfive":
+            if not _is_proxy_admin(user_api_key_dict):
+                non_admin_detail: Final[_ServiceTestErrorDetail] = {
+                    "error": "Only proxy admins can trigger the PointFive liveness ping."
+                }
+                raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail=non_admin_detail)
+            from litellm.integrations.pointfive import PointFiveLogger
+
+            try:
+                pointfive_logger: Final = PointFiveLogger(start_periodic_flush=False)
+            except ValueError as missing_key:
+                # No key configured is the answer the operator asked for, not a server error.
+                no_key: Final[_ServiceTestSuccessResponse] = {"status": "unhealthy", "message": str(missing_key)}
+                return no_key
+            response = await pointfive_logger.async_health_check()
+            pointfive_health: Final[_ServiceTestSuccessResponse] = {
+                "status": response["status"],
+                "message": (response["error_message"] if response["status"] == "unhealthy" else "PointFive is healthy")
+                or "PointFive is healthy",
+            }
+            return pointfive_health
         if service == "webhook":
             user_info: Final = CallInfo(
                 token=user_api_key_dict.token or "",
@@ -724,13 +748,42 @@ def _aggregate_health_check_results(
     return model_results
 
 
+class _AggregatedHealthResult(TypedDict):
+    """One entry of ``_aggregate_health_check_results``: a model's counts for this cycle."""
+
+    model_name: ReadOnly[str]
+    model_id: ReadOnly[str | None]
+    healthy_count: ReadOnly[int]
+    unhealthy_count: ReadOnly[int]
+    error_message: ReadOnly[str | None]
+
+
+def _new_health_status(result: _AggregatedHealthResult) -> str:
+    return "healthy" if result["healthy_count"] > 0 else "unhealthy"
+
+
+def _should_persist_health_check_result(
+    result: _AggregatedHealthResult, latest_checks_map: Mapping[str, LatestHealthCheckRow]
+) -> bool:
+    """
+    True when this result has to be written: no previous row, the status changed, or the
+    previous row is older than one hour (periodic refresh while the status is stable).
+    """
+    lookup_key: Final = result["model_id"] if result["model_id"] else result["model_name"]
+    last_check: Final = latest_checks_map.get(lookup_key)
+    if last_check is None or last_check.status != _new_health_status(result):
+        return True
+    time_since_last_check: Final = (datetime.now(timezone.utc) - last_check.checked_at).total_seconds()
+    return time_since_last_check >= 3600  # 1 hour threshold
+
+
 async def _save_health_check_results_if_changed(
     prisma_client,
     model_results: dict,
     latest_checks_map: dict,
     start_time: float,
     checked_by: str | None = None,
-):
+) -> bool:
     """
     Save health check results to database, but only if status changed or >1 hour since last save.
 
@@ -741,47 +794,39 @@ async def _save_health_check_results_if_changed(
     - Status changes: Immediate write (no delay)
     - Result: ~92% reduction in DB writes for stable systems, while maintaining real-time updates on changes
 
+    The writes are awaited rather than detached so the caller learns whether this cycle's
+    persistence completed.
+
     Args:
         prisma_client: Database client
         model_results: Dictionary of aggregated health check results per model
         latest_checks_map: Dictionary mapping model_id/model_name to latest health check
         start_time: Start time of health check for calculating response time
         checked_by: Identifier for who/what performed the check
+
+    Returns:
+        True when every row that needed writing was written (including when nothing needed
+        writing); False when any write failed.
     """
-    for result in model_results.values():
-        new_status = "healthy" if result["healthy_count"] > 0 else "unhealthy"
-
-        # Check if we should save this result
-        should_save = True
-        lookup_key = result["model_id"] if result["model_id"] else result["model_name"]
-        if lookup_key in latest_checks_map:
-            last_check = latest_checks_map[lookup_key]
-            # Only save if status changed or if it's been a while since last check
-            if last_check.status == new_status:
-                # Check if last check was recent (within 1 hour)
-                if last_check.checked_at:
-                    from datetime import datetime, timezone
-
-                    time_since_last_check = (datetime.now(timezone.utc) - last_check.checked_at).total_seconds()
-                    # Only skip if status unchanged AND checked recently (within 1 hour)
-                    # This ensures we still get periodic updates even if status is stable
-                    if time_since_last_check < 3600:  # 1 hour threshold
-                        should_save = False
-
-        if should_save:
-            asyncio.create_task(
-                prisma_client.save_health_check_result(
-                    model_name=result["model_name"],
-                    model_id=result["model_id"],
-                    status=new_status,
-                    healthy_count=result["healthy_count"],
-                    unhealthy_count=result["unhealthy_count"],
-                    error_message=result["error_message"],
-                    response_time_ms=(time.time() - start_time) * 1000,
-                    details=None,
-                    checked_by=checked_by,
-                )
-            )
+    to_write: Final = tuple(
+        result for result in model_results.values() if _should_persist_health_check_result(result, latest_checks_map)
+    )
+    writes: Final = tuple(
+        prisma_client.save_health_check_result(
+            model_name=result["model_name"],
+            model_id=result["model_id"],
+            status=_new_health_status(result),
+            healthy_count=result["healthy_count"],
+            unhealthy_count=result["unhealthy_count"],
+            error_message=result["error_message"],
+            response_time_ms=(time.time() - start_time) * 1000,
+            details=None,
+            checked_by=checked_by,
+        )
+        for result in to_write
+    )
+    rows: Final = await asyncio.gather(*writes)
+    return all(row is not None for row in rows)
 
 
 async def _save_background_health_checks_to_db(
@@ -791,7 +836,7 @@ async def _save_background_health_checks_to_db(
     unhealthy_endpoints: list,
     start_time: float,
     checked_by: str | None = None,
-):
+) -> bool:
     """
     Save background health check results to database for each model.
 
@@ -800,9 +845,13 @@ async def _save_background_health_checks_to_db(
 
     OPTIMIZATION: Only saves to database if the status has changed from the last saved check.
     This dramatically reduces database writes when health status remains stable.
+
+    Returns:
+        True when this cycle's persistence completed; False when it was skipped or any step
+        failed. Never raises: a database failure must not break the health check loop.
     """
     if prisma_client is None:
-        return
+        return False
 
     try:
         # Step 1: Build mapping from model parameter to model info
@@ -825,7 +874,7 @@ async def _save_background_health_checks_to_db(
                 latest_checks_map[key] = check
 
         # Step 4: Save aggregated results, but only if status changed
-        await _save_health_check_results_if_changed(
+        return await _save_health_check_results_if_changed(
             prisma_client,
             model_results,
             latest_checks_map,
@@ -835,6 +884,7 @@ async def _save_background_health_checks_to_db(
     except Exception as db_error:
         verbose_proxy_logger.warning("Failed to save background health checks to database: %s", db_error)
         # Continue execution - don't let database save failure break health checks
+        return False
 
 
 _PROXY_ADMIN_ROLES: Final = frozenset(
@@ -1582,6 +1632,13 @@ async def _show_no_redis_warning() -> bool:
     return await count_live_proxy_workers(prisma_client) != 1
 
 
+def _show_env_credential_login_warning() -> bool:
+    from litellm.proxy.auth.login_utils import is_env_credential_login_enabled
+    from litellm.proxy.proxy_server import general_settings
+
+    return is_env_credential_login_enabled(general_settings)
+
+
 async def _get_health_readiness_details(
     response: Response | None = None,
 ) -> dict[str, Any]:
@@ -1623,6 +1680,7 @@ async def _get_health_readiness_details(
         log_level_name: Final = logging.getLevelName(verbose_logger.getEffectiveLevel())
         is_detailed_debug: Final = verbose_logger.isEnabledFor(logging.DEBUG)
         show_no_redis_warning: Final = await _show_no_redis_warning()
+        show_env_credential_login_warning: Final = _show_env_credential_login_warning()
 
         # check DB
         if prisma_client is not None:  # if db passed in, check if it's connected
@@ -1650,6 +1708,7 @@ async def _get_health_readiness_details(
                 "log_level": log_level_name,
                 "is_detailed_debug": is_detailed_debug,
                 "show_no_redis_warning": show_no_redis_warning,
+                "show_env_credential_login_warning": show_env_credential_login_warning,
             }
         else:
             return {
@@ -1662,6 +1721,7 @@ async def _get_health_readiness_details(
                 "log_level": log_level_name,
                 "is_detailed_debug": is_detailed_debug,
                 "show_no_redis_warning": show_no_redis_warning,
+                "show_env_credential_login_warning": show_env_credential_login_warning,
             }
     except Exception as e:
         raise HTTPException(status_code=503, detail=f"Service Unhealthy ({e})")
diff --git a/litellm/proxy/hooks/batch_enqueued_tokens.py b/litellm/proxy/hooks/batch_enqueued_tokens.py
index 32bccca2ab0..1a410593854 100644
--- a/litellm/proxy/hooks/batch_enqueued_tokens.py
+++ b/litellm/proxy/hooks/batch_enqueued_tokens.py
@@ -9,6 +9,7 @@ the reservation is refunded when the batch reaches a terminal state
 """
 
 import asyncio
+import logging
 import math
 import time
 import uuid
@@ -19,6 +20,7 @@ from typing import TYPE_CHECKING, Annotated, Final, Literal, Protocol, TypeAlias
 from pydantic import BaseModel, ConfigDict, Field, TypeAdapter, ValidationError
 
 from litellm._logging import verbose_proxy_logger
+from litellm.caching.redis_cache import log_redis_failure
 from litellm.constants import BATCH_ENQUEUED_TOKEN_LIMIT_METADATA_KEY, BATCH_ENQUEUED_TOKEN_TTL_SECONDS
 from litellm.proxy._types import UserAPIKeyAuth
 
@@ -233,8 +235,11 @@ class BatchEnqueuedTokenStore:
             try:
                 return await self._reserve_via_redis(reserve_script, refund_script, tokens=tokens, scopes=scopes)
             except Exception as e:  # noqa: BLE001  # any Redis failure must fall back to the in-memory counters
-                verbose_proxy_logger.warning(
-                    "Redis enqueued-token reserve failed, falling back to in-memory: %s", str(e)
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "Redis enqueued-token reserve failed, falling back to in-memory",
+                    e,
                 )
         return await self._reserve_in_memory(tokens=tokens, scopes=scopes, span=litellm_parent_otel_span)
 
@@ -374,8 +379,11 @@ class BatchEnqueuedTokenStore:
                     (serialized, ttl),
                 )
             except Exception as e:  # noqa: BLE001  # any Redis failure must fall back to the in-memory record
-                verbose_proxy_logger.warning(
-                    "Redis enqueued-token reservation save failed, falling back to in-memory: %s", str(e)
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "Redis enqueued-token reservation save failed, falling back to in-memory",
+                    e,
                 )
             else:
                 return
@@ -421,8 +429,11 @@ class BatchEnqueuedTokenStore:
                 await pop_script((self._record_key(batch_id),), (BATCH_ENQUEUED_TOKEN_TTL_SECONDS,))
             )
         except Exception as e:  # noqa: BLE001  # any Redis failure must fall back to the in-memory record
-            verbose_proxy_logger.warning(
-                "Redis enqueued-token reservation pop failed, falling back to in-memory: %s", str(e)
+            log_redis_failure(
+                verbose_proxy_logger,
+                logging.WARNING,
+                "Redis enqueued-token reservation pop failed, falling back to in-memory",
+                e,
             )
             return None
 
diff --git a/litellm/proxy/hooks/dynamic_rate_limiter_v3.py b/litellm/proxy/hooks/dynamic_rate_limiter_v3.py
index de8834449de..0339cf4dfea 100644
--- a/litellm/proxy/hooks/dynamic_rate_limiter_v3.py
+++ b/litellm/proxy/hooks/dynamic_rate_limiter_v3.py
@@ -32,6 +32,10 @@ from litellm.proxy.hooks.rate_limiter_utils import (
     resolve_llm_provider_for_rate_limit,
 )
 from litellm.proxy.utils import InternalUsageCache
+from litellm.router_utils.add_retry_fallback_headers import (
+    ensure_response_additional_headers,
+    response_has_hidden_params,
+)
 from litellm.types.router import ModelGroupInfo
 from litellm.types.utils import CallTypesLiteral
 
@@ -55,6 +59,10 @@ def _get_priority_settings() -> "PriorityReservationSettings":
     return settings
 
 
+def _is_latin1_encodable(value: object) -> bool:
+    return all(ord(char) < 256 for char in str(value))
+
+
 class _PROXY_DynamicRateLimitHandlerV3(CustomLogger):
     """
     Saturation-aware priority-based rate limiter using v3 infrastructure.
@@ -659,22 +667,18 @@ class _PROXY_DynamicRateLimitHandlerV3(CustomLogger):
                 data=data, user_api_key_dict=user_api_key_dict, response=response
             )
 
-            # Add additional priority-specific headers
-            if isinstance(response, ModelResponse):
+            if response_has_hidden_params(response):
                 priority: Final = self._get_priority_from_user_api_key_dict(user_api_key_dict=user_api_key_dict)
-
-                # Get existing additional headers
-                additional_headers: Final = getattr(response, "_hidden_params", {}).get("additional_headers", {}) or {}
-
-                # Add priority information
-                additional_headers["x-litellm-priority"] = priority or "default"
+                additional_headers: Final = ensure_response_additional_headers(response)
+                priority_header: Final = priority or "default"
+                if _is_latin1_encodable(priority_header):
+                    additional_headers["x-litellm-priority"] = priority_header
+                else:
+                    verbose_proxy_logger.debug(
+                        "Skipping x-litellm-priority header: priority %r is not Latin-1 encodable", priority
+                    )
                 additional_headers["x-litellm-rate-limiter-version"] = "v3"
 
-                # Update response
-                if not hasattr(response, "_hidden_params"):
-                    response._hidden_params = {}
-                response._hidden_params["additional_headers"] = additional_headers
-
             return response
 
         except Exception as e:
diff --git a/litellm/proxy/hooks/max_budget_per_session_limiter.py b/litellm/proxy/hooks/max_budget_per_session_limiter.py
index 0b8e4e65258..e07b96e5773 100644
--- a/litellm/proxy/hooks/max_budget_per_session_limiter.py
+++ b/litellm/proxy/hooks/max_budget_per_session_limiter.py
@@ -14,11 +14,13 @@ Works across multiple proxy instances via DualCache (in-memory + Redis).
 Follows the same pattern as max_iterations_limiter.py.
 """
 
+import logging
 import os
 from typing import TYPE_CHECKING, Any, Final
 
 from litellm import DualCache
 from litellm._logging import verbose_proxy_logger
+from litellm.caching.redis_cache import log_redis_failure
 from litellm.exceptions import RateLimitType
 from litellm.integrations.custom_logger import CustomLogger
 from litellm.proxy._types import UserAPIKeyAuth
@@ -215,9 +217,11 @@ class _PROXY_MaxBudgetPerSessionHandler(CustomLogger):
                     return float(result)
                 return 0.0
             except Exception as e:
-                verbose_proxy_logger.warning(
-                    "MaxBudgetPerSessionHandler: Redis GET failed, falling back to in-memory: %s",
-                    str(e),
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "MaxBudgetPerSessionHandler: Redis GET failed, falling back to in-memory",
+                    e,
                 )
 
         result = await self.internal_usage_cache.async_get_cache(
@@ -239,9 +243,11 @@ class _PROXY_MaxBudgetPerSessionHandler(CustomLogger):
                 )
                 return float(result)
             except Exception as e:
-                verbose_proxy_logger.warning(
-                    "MaxBudgetPerSessionHandler: Redis INCRBYFLOAT failed, falling back to in-memory: %s",
-                    str(e),
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "MaxBudgetPerSessionHandler: Redis INCRBYFLOAT failed, falling back to in-memory",
+                    e,
                 )
 
         return await self._in_memory_increment_spend(cache_key, amount)
diff --git a/litellm/proxy/hooks/parallel_request_limiter_v3.py b/litellm/proxy/hooks/parallel_request_limiter_v3.py
index 31437af7770..c398abff099 100644
--- a/litellm/proxy/hooks/parallel_request_limiter_v3.py
+++ b/litellm/proxy/hooks/parallel_request_limiter_v3.py
@@ -6,6 +6,7 @@ This is currently in development and not yet ready for production.
 
 import asyncio
 import binascii
+import logging
 import os
 import uuid
 from collections.abc import Awaitable, Callable, Mapping, Sequence, Set
@@ -26,11 +27,13 @@ from typing_extensions import NotRequired, ReadOnly
 
 from litellm import DualCache
 from litellm._logging import verbose_proxy_logger
+from litellm.caching.redis_cache import log_redis_failure
 from litellm.constants import DYNAMIC_RATE_LIMIT_ERROR_THRESHOLD_PER_MINUTE, INTERNAL_CALL_ORIGIN_METADATA_KEY
 from litellm.integrations.custom_logger import CustomLogger
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     get_str_from_messages,
 )
+from litellm.litellm_core_utils.token_counter import offload_token_count
 from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.auth.auth_utils import (
     ESTIMATED_OUTPUT_TOKENS_FIELD,
@@ -52,6 +55,10 @@ from litellm.proxy.hooks.batch_enqueued_tokens import (
     canonical_provider_batch_id,
 )
 from litellm.proxy.hooks.rate_limiter_utils import resolve_llm_provider_for_rate_limit
+from litellm.router_utils.add_retry_fallback_headers import (
+    ensure_response_additional_headers,
+    response_has_hidden_params,
+)
 from litellm.types.caching import RedisPipelineIncrementOperation
 from litellm.types.llms.openai import BaseLiteLLMOpenAIResponseObject, ResponseAPIUsage
 from litellm.types.utils import (
@@ -1223,7 +1230,9 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                 )
                 all_cache_values.extend(group_cache_values)
             except Exception as e:
-                verbose_proxy_logger.warning("Redis Lua script failed for hash tag %s: %s", hash_tag, e)
+                log_redis_failure(
+                    verbose_proxy_logger, logging.WARNING, f"Redis Lua script failed for hash tag {hash_tag}", e
+                )
                 # Fallback to in-memory cache for this group
                 group_cache_values = await self.in_memory_cache_sliding_window(
                     keys=group_keys,
@@ -1470,7 +1479,9 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                     )
                     counts = [max(0, int(value)) for value in raw_counts]
                 except Exception as e:  # noqa: BLE001 - any Redis/Lua failure degrades to the local mirror, never a 500
-                    verbose_proxy_logger.warning("parallel_count_script failed, using local mirror: %s", e)
+                    log_redis_failure(
+                        verbose_proxy_logger, logging.WARNING, "parallel_count_script failed, using local mirror", e
+                    )
                     counts = await self._read_local_gauge_counts(gauge_keys, parent_otel_span)
             else:
                 counts = await self._read_local_gauge_counts(gauge_keys, parent_otel_span)
@@ -1500,7 +1511,12 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                     ],
                 )
             except Exception as e:  # noqa: BLE001 - any Redis/Lua failure degrades to in-memory enforcement, never a 500
-                verbose_proxy_logger.warning("parallel_acquire_script failed, falling back to in-memory gauge: %s", e)
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "parallel_acquire_script failed, falling back to in-memory gauge",
+                    e,
+                )
                 async with self._check_and_increment_lock:
                     return await self._acquire_parallel_slots_in_memory(gauges, slot_id, parent_otel_span)
             if int(raw[0]) == 1:
@@ -1626,7 +1642,12 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                     )
                 return
             except Exception as e:  # noqa: BLE001 - any Redis/Lua failure degrades to the in-memory release, never a 500
-                verbose_proxy_logger.warning("parallel_release_script failed, falling back to in-memory release: %s", e)
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "parallel_release_script failed, falling back to in-memory release",
+                    e,
+                )
 
         async with self._check_and_increment_lock:
             for counter_key in counter_keys:
@@ -1809,12 +1830,13 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                 # state ambiguous. Refund any prior groups so Redis returns
                 # to its pre-call state, then fall back to in-memory for the
                 # whole call (counters there are independent of Redis).
-                verbose_proxy_logger.error(
-                    "atomic_check_and_increment_by_n: Redis Lua execution failed (%s: %s). Refunding %s prior descriptors and falling back to in-memory enforcement — counters will diverge from Redis until window expires (window_size=%ss).",
-                    type(e).__name__,
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.ERROR,
+                    f"atomic_check_and_increment_by_n: Redis Lua execution failed ({type(e).__name__}). Refunding "
+                    f"{len(applied)} prior descriptors and falling back to in-memory enforcement, counters will "
+                    f"diverge from Redis until window expires (window_size={self.window_size}s)",
                     e,
-                    len(applied),
-                    self.window_size,
                 )
                 await self._refund_applied_descriptor_groups(applied)
                 flat_meta: list[AtomicCounterMeta] = [m for _k, _a, group_meta in descriptor_groups for m in group_meta]
@@ -1861,8 +1883,11 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                         value=-entry["increment"],
                     )
                 except Exception as e:
-                    verbose_proxy_logger.warning(
-                        "Failed to refund %s on cross-descriptor rollback: %s", entry["counter_key"], e
+                    log_redis_failure(
+                        verbose_proxy_logger,
+                        logging.WARNING,
+                        f"Failed to refund {entry['counter_key']} on cross-descriptor rollback",
+                        e,
                     )
 
     def _build_atomic_response(
@@ -3303,7 +3328,7 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
             min_configured_tpm_limit=min_configured_otpm_limit,
             call_type=call_type,
         )
-        raw_estimated_input_tokens: Final = self._estimate_precise_input_tokens(
+        raw_estimated_input_tokens: Final = await offload_token_count(self._estimate_precise_input_tokens)(
             data=data, model=requested_model, call_type=call_type
         )
         estimated_input_tokens: Final = max(raw_estimated_input_tokens, 1)
@@ -3851,7 +3876,9 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
             )
 
         except Exception as e:
-            verbose_proxy_logger.warning("TTL preservation failed, falling back to regular pipeline: %s", e)
+            log_redis_failure(
+                verbose_proxy_logger, logging.WARNING, "TTL preservation failed, falling back to regular pipeline", e
+            )
             # Fallback to regular pipeline on error
             await self.internal_usage_cache.dual_cache.async_increment_cache_pipeline(
                 increment_list=pipeline_operations,
@@ -3917,9 +3944,10 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
                     )
                     continue
                 except Exception as e:  # noqa: BLE001  # Redis failures use the plain increment fallback
-                    verbose_proxy_logger.warning(
-                        "Window-guarded token adjustment failed for %s: %s",
-                        operation["key"],
+                    log_redis_failure(
+                        verbose_proxy_logger,
+                        logging.WARNING,
+                        f"Window-guarded token adjustment failed for {operation['key']}",
                         e,
                     )
             if operation["increment_value"] > 0:
@@ -4677,34 +4705,17 @@ class _PROXY_MaxParallelRequestsHandler_v3(CustomLogger):
         Post-call hook to update rate limit headers in the response.
         """
         try:
-            from pydantic import BaseModel
-
             stash: Final = get_request_stash()
             litellm_proxy_rate_limit_response: Final = stash.rate_limit_response if stash is not None else None
 
-            if litellm_proxy_rate_limit_response is not None:
-                # Update response headers
-                if hasattr(response, "_hidden_params"):
-                    _hidden_params = getattr(response, "_hidden_params")
-                else:
-                    _hidden_params = None
-
-                if _hidden_params is not None and (
-                    isinstance(_hidden_params, BaseModel) or isinstance(_hidden_params, dict)
-                ):
-                    if isinstance(_hidden_params, BaseModel):
-                        _hidden_params = _hidden_params.model_dump()
-
-                    _additional_headers: Final = self._merge_ratelimit_statuses_into_additional_headers(
-                        additional_headers=_hidden_params.get("additional_headers", {}) or {},
+            if litellm_proxy_rate_limit_response is not None and response_has_hidden_params(response):
+                additional_headers: Final = ensure_response_additional_headers(response)
+                additional_headers.update(
+                    self._merge_ratelimit_statuses_into_additional_headers(
+                        additional_headers={},
                         statuses=litellm_proxy_rate_limit_response["statuses"],
                     )
-
-                    setattr(
-                        response,
-                        "_hidden_params",
-                        {**_hidden_params, "additional_headers": _additional_headers},
-                    )
+                )
 
         except Exception as e:
             verbose_proxy_logger.exception("Error in rate limit post-call hook: %s", e)
diff --git a/litellm/proxy/hooks/proxy_track_cost_callback.py b/litellm/proxy/hooks/proxy_track_cost_callback.py
index c4fba8ecf9e..00406ad436e 100644
--- a/litellm/proxy/hooks/proxy_track_cost_callback.py
+++ b/litellm/proxy/hooks/proxy_track_cost_callback.py
@@ -27,6 +27,16 @@ from litellm.proxy.db.db_spend_update_writer import (
     get_llm_router,
 )
 from litellm.proxy.litellm_pre_call_utils import LiteLLMProxyRequestSetup
+from litellm.proxy.spend_tracking.spend_event import (
+    ObjectMapping,
+    SpendEventBuildError,
+    SpendEventDecodeError,
+    build_spend_event,
+    decode_spend_event,
+    is_offloadable_success,
+    spend_event_callback_args,
+)
+from litellm.proxy.spend_tracking.spend_event_producer import SpendEventProducer
 from litellm.proxy.spend_tracking.spend_log_error_logger import (
     should_suppress_spend_log_tracebacks,
     spend_log_error,
@@ -34,6 +44,7 @@ from litellm.proxy.spend_tracking.spend_log_error_logger import (
 from litellm.proxy.spend_tracking.spend_tracking_utils import (
     _sanitize_error_information_for_spend_logs,
     get_request_model_access_groups,
+    should_store_prompts_and_responses_in_spend_logs,
 )
 from litellm.proxy.utils import ProxyUpdateSpend
 from litellm.types.utils import (
@@ -71,8 +82,43 @@ _CAPTURED_IDENTITY_CALL_TYPES: Final[frozenset[str]] = frozenset(
 
 
 class _ProxyDBLogger(CustomLogger):
-    async def async_log_success_event(self, kwargs, response_obj, start_time, end_time):
-        await self._PROXY_track_cost_callback(kwargs, response_obj, start_time, end_time)
+    def __init__(
+        self,
+        spend_event_producer: SpendEventProducer | None = None,
+        *,
+        turn_off_message_logging: bool = False,
+        message_logging: bool = True,
+    ) -> None:
+        super().__init__(turn_off_message_logging=turn_off_message_logging, message_logging=message_logging)
+        self.spend_event_producer = spend_event_producer
+
+    async def async_log_success_event(
+        self, kwargs: ObjectMapping, response_obj: object, start_time: datetime, end_time: datetime
+    ) -> None:
+        if self.spend_event_producer is None or not is_offloadable_success(response_obj):
+            await self._PROXY_track_cost_callback(kwargs, response_obj, start_time, end_time)
+            return
+        event: Final = build_spend_event(
+            kwargs,
+            response_obj,
+            start_time,
+            end_time,
+            store_bodies=should_store_prompts_and_responses_in_spend_logs(),
+        )
+        if isinstance(event, SpendEventBuildError):
+            verbose_proxy_logger.warning("collector: tracking cost in-process, event not buildable: %s", event.reason)
+            await self._PROXY_track_cost_callback(kwargs, response_obj, start_time, end_time)
+            return
+        await self.spend_event_producer.publish(event)
+
+    async def run_spend_event(self, line: bytes) -> None:
+        """Run the unchanged cost pipeline on a serialized spend event (sidecar consumer and in-process fallback)."""
+        event: Final = decode_spend_event(line)
+        if isinstance(event, SpendEventDecodeError):
+            verbose_proxy_logger.error("collector: discarding undecodable spend event: %s", event.reason)
+            return
+        args: Final = spend_event_callback_args(event)
+        await self._PROXY_track_cost_callback(args.kwargs, args.response_obj, args.start_time, args.end_time)
 
     async def async_post_call_failure_hook(
         self,
@@ -503,6 +549,10 @@ def _write_spend_metadata_to_kwargs(kwargs: dict, metadata: dict) -> None:
                     bucket[key] = value
 
 
+async def run_spend_event(line: bytes) -> None:
+    await _ProxyDBLogger().run_spend_event(line)
+
+
 def _is_unbilled_interaction_response(completion_response: object) -> bool:
     from litellm.interactions.background_cost_polling import missing_usage_is_expected
     from litellm.types.interactions import InteractionsAPIResponse
diff --git a/litellm/proxy/hooks/sensitive_data_routing.py b/litellm/proxy/hooks/sensitive_data_routing.py
index 4d846744b55..bc89dec7a11 100644
--- a/litellm/proxy/hooks/sensitive_data_routing.py
+++ b/litellm/proxy/hooks/sensitive_data_routing.py
@@ -10,11 +10,13 @@ this hook manages:
 Works across multiple proxy instances via DualCache (in-memory + Redis).
 """
 
+import logging
 import os
 from typing import TYPE_CHECKING, Any, Final
 
 from litellm._logging import verbose_proxy_logger
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import log_redis_failure
 from litellm.integrations.custom_guardrail import get_session_id_from_request_data
 from litellm.integrations.custom_logger import CustomLogger
 from litellm.proxy._types import UserAPIKeyAuth
@@ -96,9 +98,11 @@ class _PROXY_SensitiveDataRoutingHandler(CustomLogger):
                     )
                     return routed_model
             except Exception as e:
-                verbose_proxy_logger.warning(
-                    "SensitiveDataRoutingHandler: Redis GET failed, falling back to in-memory: %s",
-                    str(e),
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "SensitiveDataRoutingHandler: Redis GET failed, falling back to in-memory",
+                    e,
                 )
 
         result = await self.internal_usage_cache.async_get_cache(
@@ -142,9 +146,11 @@ class _PROXY_SensitiveDataRoutingHandler(CustomLogger):
                     ttl=self.ttl,
                 )
             except Exception as e:
-                verbose_proxy_logger.warning(
-                    "SensitiveDataRoutingHandler: Redis SET failed, falling back to in-memory: %s",
-                    str(e),
+                log_redis_failure(
+                    verbose_proxy_logger,
+                    logging.WARNING,
+                    "SensitiveDataRoutingHandler: Redis SET failed, falling back to in-memory",
+                    e,
                 )
 
         await self.internal_usage_cache.async_set_cache(
diff --git a/litellm/proxy/litellm_pre_call_utils.py b/litellm/proxy/litellm_pre_call_utils.py
index 924f84be5f4..ad4687e95db 100644
--- a/litellm/proxy/litellm_pre_call_utils.py
+++ b/litellm/proxy/litellm_pre_call_utils.py
@@ -31,6 +31,7 @@ from litellm.constants import (
     SESSION_ID_OMITTED_METADATA_KEY,
     X_LITELLM_DISABLE_CALLBACKS,
 )
+from litellm.litellm_core_utils.core_helpers import is_codex_user_agent
 from litellm.litellm_core_utils.credential_accessor import CredentialAccessor
 from litellm.litellm_core_utils.initialize_dynamic_callback_params import (
     TRUSTED_CALLBACK_VARS_FIELD,
@@ -83,10 +84,6 @@ _EXPLICIT_SESSION_HEADERS: Final = frozenset({"x-litellm-trace-id", "x-litellm-s
 # ``session-id``/``thread-id``; builds before the codex-api split sent
 # ``session_id``/``conversation_id``. Ordered session before thread.
 _CODEX_SESSION_ID_HEADERS: Final = ("session-id", "session_id", "thread-id", "conversation_id")
-# Matches every first-party Codex originator: codex-tui, codex_cli_rs, codex_exec,
-# codex_vscode, "Codex ...". A separator is required so an unrelated "codexfoo" client
-# does not read as Codex.
-_CODEX_CLIENT_PREFIX_RE: Final = re.compile(r"^codex[-_ /]", re.IGNORECASE)
 # Session-id values must be non-empty strings of alphanumerics, hyphens, or underscores
 # (covers UUIDs and most common session-id formats).
 _SESSION_ID_VALUE_RE: Final = re.compile(r"^[a-zA-Z0-9_\-]{8,}$")
@@ -235,6 +232,7 @@ _UNTRUSTED_ROOT_CONTROL_FIELDS: Final = (
     "applied_policies",
     "policy_sources",
     "guardrail_scan_ids",
+    "guardrail_scan_metadata",
     "routing_decision",
     GATEWAY_INJECTED_CACHE_METADATA_KEY,
     "pillar_response_headers",
@@ -291,6 +289,7 @@ _UNTRUSTED_METADATA_CONTROL_FIELDS: Final = (
     "applied_policies",
     "policy_sources",
     "guardrail_scan_ids",
+    "guardrail_scan_metadata",
     "routing_decision",
     GATEWAY_INJECTED_CACHE_METADATA_KEY,
     SESSION_DEPLOYMENT_AFFINITY_TTL_METADATA_KEY,
@@ -771,6 +770,16 @@ def apply_missing_session_id_policy(
         return
     if policy == "omit":
         metadata[SESSION_ID_OMITTED_METADATA_KEY] = True
+        requester_metadata: Final = data.get("metadata")
+        requester_session_id: Final = (
+            requester_metadata.get("session_id") if isinstance(requester_metadata, dict) else None
+        )
+        if (
+            (body_session_id := data.get("litellm_session_id"))
+            and not metadata.get("session_id")
+            and not requester_session_id
+        ):
+            metadata["session_id"] = body_session_id
         return
     if data.get("litellm_session_id") or metadata.get("session_id"):
         return
@@ -798,16 +807,6 @@ def apply_missing_session_id_policy(
             )
 
 
-def is_codex_user_agent(user_agent: str) -> bool:
-    """Codex builds its user agent as ``<originator>/<version> ...`` and ships
-    several first-party originators: ``codex-tui``, ``codex_cli_rs``,
-    ``codex_exec`` (exec mode), ``codex_vscode`` (IDE extension) and ``Codex ...``
-    (see ``is_first_party_originator`` in codex-rs). They agree only on the
-    ``codex`` stem, and the TUI sends a bare ``codex-tui`` with no version at all,
-    so match the stem plus a separator rather than any one spelling."""
-    return bool(_CODEX_CLIENT_PREFIX_RE.match(user_agent))
-
-
 def should_auto_drop_params_for_agentic_cli(user_agent: str, data: dict, proxy_config: ProxyConfig) -> bool:
     """drop_params defaults to on for agentic CLIs so their client-specific
     params (e.g. Claude Code's thinking, Codex's service_tier) don't fail
@@ -1748,7 +1747,9 @@ class LiteLLMProxyRequestSetup:
         callback_vars_dict.pop("success_callback", None)
         callback_vars_dict.pop("failure_callback", None)
         callback_vars_dict = {
-            key: (litellm.utils.get_secret(value, default_value=value) or value if isinstance(value, str) else value)
+            key: (
+                litellm.utils.get_secret(value, default_value=value) or value if isinstance(value, str) else str(value)
+            )
             for key, value in callback_vars_dict.items()
         }
 
diff --git a/litellm/proxy/management_endpoints/common_daily_activity.py b/litellm/proxy/management_endpoints/common_daily_activity.py
index ce6a97708ab..a8aef30107c 100644
--- a/litellm/proxy/management_endpoints/common_daily_activity.py
+++ b/litellm/proxy/management_endpoints/common_daily_activity.py
@@ -14,6 +14,7 @@ from litellm.proxy._types import CommonProxyErrors
 from litellm.proxy.spend_tracking.key_metadata_recovery import (
     attach_user_emails,
     recover_double_hashed_key_metadata,
+    recover_key_metadata_from_spend_logs,
 )
 from litellm.proxy.spend_tracking.ptu_feature_flag import is_ptu_cost_attribution_enabled
 from litellm.proxy.utils import PrismaClient
@@ -433,9 +434,29 @@ def update_breakdown_metrics(
     return breakdown
 
 
+def _spend_logs_window(dates: AbstractSet[str | None]) -> tuple[datetime, datetime] | None:
+    parsed: Final = sorted(day for day in (_parse_spend_date(raw) for raw in dates) if day is not None)
+    if not parsed:
+        return None
+    return (parsed[0] - timedelta(days=1), parsed[-1] + timedelta(days=2))
+
+
+def _parse_spend_date(raw: str | None) -> datetime | None:
+    if not isinstance(raw, str):
+        return None
+    try:
+        return datetime.fromisoformat(raw)
+    except ValueError:
+        return None
+
+
+_EMPTY_KEY_METADATA: Final[Mapping[str, _KeyMetadataDict]] = MappingProxyType({})
+
+
 async def get_api_key_metadata(
     prisma_client: PrismaClient,
     api_keys: AbstractSet[str],
+    spend_logs_window: tuple[datetime, datetime] | None = None,
 ) -> Mapping[str, _KeyMetadataDict]:
     """Get api key metadata, falling back to deleted keys table for keys not found in active table.
 
@@ -481,11 +502,17 @@ async def get_api_key_metadata(
             )
 
     still_missing: Final = api_keys - frozenset(result)
-    combined: Final = (
-        result
-        if not still_missing
-        else MappingProxyType({**result, **(await recover_double_hashed_key_metadata(prisma_client, still_missing))})
+    from_reverse_hash: Final = (
+        await recover_double_hashed_key_metadata(prisma_client, still_missing) if still_missing else _EMPTY_KEY_METADATA
     )
+    after_token_recovery: Final = MappingProxyType({**result, **from_reverse_hash})
+    unresolved: Final = api_keys - frozenset(after_token_recovery)
+    from_spend_logs: Final = (
+        await recover_key_metadata_from_spend_logs(prisma_client, unresolved, spend_logs_window)
+        if unresolved and spend_logs_window is not None
+        else _EMPTY_KEY_METADATA
+    )
+    combined: Final = MappingProxyType({**after_token_recovery, **from_spend_logs})
     return await attach_user_emails(prisma_client, combined)
 
 
@@ -898,7 +925,9 @@ async def _aggregate_spend_records(
 
     api_key_metadata: dict[str, _KeyMetadataDict] = {}
     if api_keys:
-        api_key_metadata = await get_api_key_metadata(prisma_client, api_keys)
+        api_key_metadata = await get_api_key_metadata(
+            prisma_client, api_keys, _spend_logs_window(frozenset(record.date for record in records))
+        )
 
     return await asyncio.to_thread(
         _aggregate_spend_records_sync,
@@ -1094,7 +1123,9 @@ async def _aggregate_grouping_sets_records(
 
     api_key_metadata: dict[str, _KeyMetadataDict] = {}
     if api_keys:
-        api_key_metadata = await get_api_key_metadata(prisma_client, api_keys)
+        api_key_metadata = await get_api_key_metadata(
+            prisma_client, api_keys, _spend_logs_window(frozenset(r.date for r in records))
+        )
 
     return await asyncio.to_thread(
         _aggregate_grouping_sets_records_sync,
@@ -1357,7 +1388,9 @@ async def get_daily_activity_aggregated(
                 r.api_key for r in entity_records if r.api_key and r.api_key != PTU_SENTINEL_API_KEY
             )
             entity_key_metadata: Final = (
-                await get_api_key_metadata(prisma_client, entity_api_keys)
+                await get_api_key_metadata(
+                    prisma_client, entity_api_keys, _spend_logs_window(frozenset(r.date for r in entity_records))
+                )
                 if entity_api_keys
                 else {}  # mutable-ok: matches the helper's dict return
             )
diff --git a/litellm/proxy/management_endpoints/coordination_redis_endpoints.py b/litellm/proxy/management_endpoints/coordination_redis_endpoints.py
index 86ce336c7a3..88dc09ab001 100644
--- a/litellm/proxy/management_endpoints/coordination_redis_endpoints.py
+++ b/litellm/proxy/management_endpoints/coordination_redis_endpoints.py
@@ -140,7 +140,7 @@ def _merge_over_saved(
 def _validated_params(settings: Mapping[str, object]) -> CoordinationRedisParams:
     """Validate settings the way startup does: resolve env refs, then require a connection target."""
     try:
-        params: Final = CoordinationRedisParams(**_resolve_env_refs(settings))
+        params: Final = CoordinationRedisParams.model_validate(_resolve_env_refs(settings))
     except ValidationError as e:
         invalid_fields: Final = sorted({str(error["loc"][0]) for error in e.errors() if error["loc"]})
         raise HTTPException(
diff --git a/litellm/proxy/management_endpoints/cost_tracking_settings.py b/litellm/proxy/management_endpoints/cost_tracking_settings.py
index 204051c3715..dc0da63555f 100644
--- a/litellm/proxy/management_endpoints/cost_tracking_settings.py
+++ b/litellm/proxy/management_endpoints/cost_tracking_settings.py
@@ -18,6 +18,7 @@ from fastapi import APIRouter, Depends, HTTPException
 from pydantic import BaseModel
 
 import litellm
+from litellm._internal_context import current_billing_time, pinned_billing_time
 from litellm._logging import verbose_proxy_logger
 from litellm.cost_calculator import completion_cost
 from litellm.proxy._types import (
@@ -27,7 +28,15 @@ from litellm.proxy._types import (
     UserAPIKeyAuth,
 )
 from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
-from litellm.types.utils import CostPerToken, LlmProvidersSet, ModelInfo
+from litellm.types.utils import (
+    CostBreakdown,
+    CostPerToken,
+    LlmProvidersSet,
+    ModelInfo,
+    ModelResponse,
+    PromptTokensDetailsWrapper,
+    Usage,
+)
 
 router: Final = APIRouter()
 
@@ -46,13 +55,15 @@ def _configured_price(key: str, sources: tuple[Mapping[str, object], ...]) -> fl
 
 
 def _extract_custom_pricing(
-    litellm_params: Mapping[str, object], model_info: Mapping[str, object]
+    litellm_params: Mapping[str, object], model_info: Mapping[str, object], builtin: ModelInfo | None
 ) -> CostPerToken | None:
     """
     Pull per-token pricing configured on a deployment so on-prem / self-hosted
     models (absent from the public cost map) still estimate a real cost.
     Pricing may live on ``litellm_params`` or ``model_info``; ``litellm_params``
-    wins, matching the router's cost-map registration precedence.
+    wins, matching the router's cost-map registration precedence. Cache rates the
+    deployment leaves unset come from the backend model's built-in entry, then its
+    own input rate, again matching what the router registers for live billing.
     """
     sources: Final = (litellm_params, model_info)
     input_price: Final = _configured_price("input_cost_per_token", sources)
@@ -61,15 +72,21 @@ def _extract_custom_pricing(
     if input_price is None and output_price is None:
         return None
 
+    input_rate: Final = input_price or 0.0
+    cache_sources: Final = sources if builtin is None else (*sources, builtin)
+    cache_read_price: Final = _configured_price("cache_read_input_token_cost", cache_sources)
+    cache_creation_price: Final = _configured_price("cache_creation_input_token_cost", cache_sources)
     return CostPerToken(
-        input_cost_per_token=input_price or 0.0,
+        input_cost_per_token=input_rate,
         output_cost_per_token=output_price or 0.0,
+        cache_read_input_token_cost=input_rate if cache_read_price is None else cache_read_price,
+        cache_creation_input_token_cost=input_rate if cache_creation_price is None else cache_creation_price,
     )
 
 
-def _lookup_model_info(model: str) -> ModelInfo | None:
+def _lookup_model_info(model: str, custom_llm_provider: str | None = None) -> ModelInfo | None:
     try:
-        return litellm.get_model_info(model=model)
+        return litellm.get_model_info(model=model, custom_llm_provider=custom_llm_provider)
     except Exception:
         return None
 
@@ -98,17 +115,14 @@ def _resolve_model_for_cost_lookup(model: str) -> ResolvedCostModel:
                 model_info: Final = first_deployment.get("model_info", {})
                 custom_llm_provider: Final = litellm_params.get("custom_llm_provider")
                 provider: Final = str(custom_llm_provider) if custom_llm_provider is not None else None
-                custom_cost_per_token: Final = _extract_custom_pricing(litellm_params, model_info)
-
-                # Check base_model first (needed for Azure custom deployment names)
+                # base_model wins (needed for Azure custom deployment names)
                 base_model: Final = model_info.get("base_model") or litellm_params.get("base_model")
-                if base_model:
-                    verbose_proxy_logger.debug("Resolved model '%s' to base_model '%s' from router", model, base_model)
-                    return ResolvedCostModel(str(base_model), provider, custom_cost_per_token)
-
-                resolved_model: Final = litellm_params.get("model")
+                resolved_model: Final = base_model or litellm_params.get("model")
                 if resolved_model:
                     verbose_proxy_logger.debug("Resolved model '%s' to '%s' from router", model, resolved_model)
+                    custom_cost_per_token: Final = _extract_custom_pricing(
+                        litellm_params, model_info, _lookup_model_info(str(resolved_model), provider)
+                    )
                     return ResolvedCostModel(str(resolved_model), provider, custom_cost_per_token)
         except Exception as e:
             verbose_proxy_logger.debug("Could not resolve model '%s' from router: %s", model, e)
@@ -117,19 +131,59 @@ def _resolve_model_for_cost_lookup(model: str) -> ResolvedCostModel:
     return ResolvedCostModel(model, None, None)
 
 
-def _calculate_period_costs(num_requests, cost_per_request, input_cost, output_cost, margin_cost):
-    """
-    Calculate costs for a given number of requests.
+@dataclass(frozen=True, slots=True)
+class CostLines:
+    """Cost of one request split the way the spend logs split it: the cache lines are
+    shares of input_cost and the reasoning line is a share of output_cost."""
 
-    Returns tuple of (total_cost, input_cost, output_cost, margin_cost) or all None if num_requests is None/0.
-    """
-    if not num_requests:
-        return None, None, None, None
-    return (
-        cost_per_request * num_requests,
-        input_cost * num_requests,
-        output_cost * num_requests,
-        margin_cost * num_requests,
+    total_cost: float
+    input_cost: float
+    output_cost: float
+    margin_cost: float
+    cache_read_cost: float
+    cache_creation_cost: float
+    reasoning_cost: float
+
+    def times(self, num_requests: int | None) -> "CostLines | None":
+        if not num_requests:
+            return None
+        return CostLines(
+            total_cost=self.total_cost * num_requests,
+            input_cost=self.input_cost * num_requests,
+            output_cost=self.output_cost * num_requests,
+            margin_cost=self.margin_cost * num_requests,
+            cache_read_cost=self.cache_read_cost * num_requests,
+            cache_creation_cost=self.cache_creation_cost * num_requests,
+            reasoning_cost=self.reasoning_cost * num_requests,
+        )
+
+
+def _cost_lines(cost_per_request: float, cost_breakdown: CostBreakdown | None) -> CostLines:
+    breakdown: Final = cost_breakdown if cost_breakdown is not None else CostBreakdown()
+    return CostLines(
+        total_cost=cost_per_request,
+        input_cost=breakdown.get("input_cost", 0.0),
+        output_cost=breakdown.get("output_cost", 0.0),
+        margin_cost=breakdown.get("margin_total_amount", 0.0),
+        cache_read_cost=breakdown.get("cache_read_cost", 0.0),
+        cache_creation_cost=breakdown.get("cache_creation_cost", 0.0),
+        reasoning_cost=breakdown.get("reasoning_cost", 0.0),
+    )
+
+
+def _usage_for_estimate(request: CostEstimateRequest) -> Usage:
+    cache_tokens: Final = request.cache_read_input_tokens + request.cache_creation_input_tokens
+    return Usage(
+        prompt_tokens=request.input_tokens,
+        completion_tokens=request.output_tokens,
+        total_tokens=request.input_tokens + request.output_tokens,
+        reasoning_tokens=request.reasoning_tokens,
+        prompt_tokens_details=PromptTokensDetailsWrapper(
+            cached_tokens=request.cache_read_input_tokens,
+            cache_creation_tokens=request.cache_creation_input_tokens,
+        )
+        if cache_tokens
+        else None,
     )
 
 
@@ -530,11 +584,14 @@ async def estimate_cost(
     - model: Model name (e.g., "gpt-4", "claude-3-opus")
     - input_tokens: Expected input tokens per request
     - output_tokens: Expected output tokens per request
+    - cache_read_input_tokens: Cache-read tokens per request, counted within input_tokens (optional)
+    - cache_creation_input_tokens: Cache-write tokens per request, counted within input_tokens (optional)
+    - reasoning_tokens: Reasoning tokens per request, counted within output_tokens (optional)
     - num_requests_per_day: Number of requests per day (optional)
     - num_requests_per_month: Number of requests per month (optional)
 
     Returns cost breakdown including:
-    - Per-request costs (input, output, margin)
+    - Per-request costs (input, output, margin, plus the cache-read, cache-write and reasoning shares)
     - Daily costs (if num_requests_per_day provided)
     - Monthly costs (if num_requests_per_month provided)
 
@@ -543,14 +600,15 @@ async def estimate_cost(
     {
         "model": "gpt-4",
         "input_tokens": 1000,
+        "cache_read_input_tokens": 800,
         "output_tokens": 500,
+        "reasoning_tokens": 200,
         "num_requests_per_day": 100,
         "num_requests_per_month": 3000
     }
     ```
     """
     from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
-    from litellm.types.utils import ModelResponse, Usage
 
     # Resolve model name (handles router aliases like 'e-model-router' -> 'azure_ai/gpt-4')
     resolved: Final = _resolve_model_for_cost_lookup(request.model)
@@ -559,15 +617,8 @@ async def estimate_cost(
 
     verbose_proxy_logger.debug("Cost estimate: request.model='%s' resolved to '%s'", request.model, resolved_model)
 
-    # Create a mock response with usage for completion_cost
-    mock_response: Final = ModelResponse(
-        model=resolved_model,
-        usage=Usage(
-            prompt_tokens=request.input_tokens,
-            completion_tokens=request.output_tokens,
-            total_tokens=request.input_tokens + request.output_tokens,
-        ),
-    )
+    usage: Final = _usage_for_estimate(request)
+    mock_response: Final = ModelResponse(model=resolved_model, usage=usage)
 
     # Create a logging object to capture cost breakdown
     litellm_logging_obj: Final = LiteLLMLoggingObj(
@@ -580,92 +631,73 @@ async def estimate_cost(
         function_id="cost-estimate",
     )
 
-    # Use completion_cost which handles all the logic including margins/discounts
-    try:
-        cost_per_request: Final = completion_cost(
-            completion_response=mock_response,
-            model=resolved_model,
-            custom_llm_provider=resolved_provider,
-            custom_cost_per_token=resolved.custom_cost_per_token,
-            litellm_logging_obj=litellm_logging_obj,
-        )
-    except Exception as e:
-        raise HTTPException(
-            status_code=404,
-            detail={
-                "error": f"Could not calculate cost for model '{request.model}' (resolved to '{resolved_model}'): {e}"
-            },
-        )
+    # Pinning one moment keeps an off-peak window that opens mid-quote from pricing the totals on
+    # one side of it and the reported rates on the other.
+    with pinned_billing_time(current_billing_time()):
+        # Use completion_cost which handles all the logic including margins/discounts
+        try:
+            cost_per_request: Final = completion_cost(
+                completion_response=mock_response,
+                model=resolved_model,
+                custom_llm_provider=resolved_provider,
+                custom_cost_per_token=resolved.custom_cost_per_token,
+                litellm_logging_obj=litellm_logging_obj,
+            )
+        except Exception as e:  # noqa: BLE001  # completion_cost raises a bare Exception for an unpriceable model
+            raise HTTPException(
+                status_code=404,
+                detail={
+                    "error": f"Could not calculate cost for model '{request.model}' (resolved to '{resolved_model}'): {e}"
+                },
+            )
 
-    # Get cost breakdown from the logging object
-    cost_breakdown: Final = litellm_logging_obj.cost_breakdown
+    # The rates come back from the pricing call itself rather than a second lookup, so they are the
+    # ones the cost lines above billed at even when completion_cost infers a provider this endpoint
+    # never resolved (an unrouted "xai/grok-4" prices on xai's inclusive tier thresholds; a lookup
+    # here without that provider would report the sub-200k rate for a line billed above it).
+    rates: Final = litellm_logging_obj.billed_token_rates
+    per_request: Final = _cost_lines(cost_per_request, litellm_logging_obj.cost_breakdown)
+    daily: Final = per_request.times(request.num_requests_per_day)
+    monthly: Final = per_request.times(request.num_requests_per_month)
 
-    input_cost: Final = cost_breakdown.get("input_cost", 0.0) if cost_breakdown else 0.0
-    output_cost: Final = cost_breakdown.get("output_cost", 0.0) if cost_breakdown else 0.0
-    margin_cost: Final = cost_breakdown.get("margin_total_amount", 0.0) if cost_breakdown else 0.0
-
-    model_info: Final = _lookup_model_info(resolved_model)
-    mapped_input_price: Final = model_info.get("input_cost_per_token") if model_info is not None else None
-    mapped_output_price: Final = model_info.get("output_cost_per_token") if model_info is not None else None
+    model_info: Final = _lookup_model_info(resolved_model, resolved_provider)
     mapped_provider: Final = model_info.get("litellm_provider") if model_info is not None else None
-
-    input_cost_per_token: Final = (
-        resolved.custom_cost_per_token["input_cost_per_token"]
-        if resolved.custom_cost_per_token is not None
-        else mapped_input_price
-    )
-    output_cost_per_token: Final = (
-        resolved.custom_cost_per_token["output_cost_per_token"]
-        if resolved.custom_cost_per_token is not None
-        else mapped_output_price
-    )
     custom_llm_provider: Final = mapped_provider if mapped_provider is not None else resolved_provider
 
-    # Calculate daily and monthly costs
-    (
-        daily_cost,
-        daily_input_cost,
-        daily_output_cost,
-        daily_margin_cost,
-    ) = _calculate_period_costs(
-        num_requests=request.num_requests_per_day,
-        cost_per_request=cost_per_request,
-        input_cost=input_cost,
-        output_cost=output_cost,
-        margin_cost=margin_cost,
-    )
-    (
-        monthly_cost,
-        monthly_input_cost,
-        monthly_output_cost,
-        monthly_margin_cost,
-    ) = _calculate_period_costs(
-        num_requests=request.num_requests_per_month,
-        cost_per_request=cost_per_request,
-        input_cost=input_cost,
-        output_cost=output_cost,
-        margin_cost=margin_cost,
-    )
-
     return CostEstimateResponse(
         model=request.model,
         input_tokens=request.input_tokens,
         output_tokens=request.output_tokens,
+        cache_read_input_tokens=request.cache_read_input_tokens,
+        cache_creation_input_tokens=request.cache_creation_input_tokens,
+        reasoning_tokens=request.reasoning_tokens,
         num_requests_per_day=request.num_requests_per_day,
         num_requests_per_month=request.num_requests_per_month,
-        cost_per_request=cost_per_request,
-        input_cost_per_request=input_cost,
-        output_cost_per_request=output_cost,
-        margin_cost_per_request=margin_cost,
-        daily_cost=daily_cost,
-        daily_input_cost=daily_input_cost,
-        daily_output_cost=daily_output_cost,
-        daily_margin_cost=daily_margin_cost,
-        monthly_cost=monthly_cost,
-        monthly_input_cost=monthly_input_cost,
-        monthly_output_cost=monthly_output_cost,
-        monthly_margin_cost=monthly_margin_cost,
-        input_cost_per_token=input_cost_per_token,
-        output_cost_per_token=output_cost_per_token,
+        cost_per_request=per_request.total_cost,
+        input_cost_per_request=per_request.input_cost,
+        output_cost_per_request=per_request.output_cost,
+        margin_cost_per_request=per_request.margin_cost,
+        cache_read_cost_per_request=per_request.cache_read_cost,
+        cache_creation_cost_per_request=per_request.cache_creation_cost,
+        reasoning_cost_per_request=per_request.reasoning_cost,
+        daily_cost=daily.total_cost if daily is not None else None,
+        daily_input_cost=daily.input_cost if daily is not None else None,
+        daily_output_cost=daily.output_cost if daily is not None else None,
+        daily_margin_cost=daily.margin_cost if daily is not None else None,
+        daily_cache_read_cost=daily.cache_read_cost if daily is not None else None,
+        daily_cache_creation_cost=daily.cache_creation_cost if daily is not None else None,
+        daily_reasoning_cost=daily.reasoning_cost if daily is not None else None,
+        monthly_cost=monthly.total_cost if monthly is not None else None,
+        monthly_input_cost=monthly.input_cost if monthly is not None else None,
+        monthly_output_cost=monthly.output_cost if monthly is not None else None,
+        monthly_margin_cost=monthly.margin_cost if monthly is not None else None,
+        monthly_cache_read_cost=monthly.cache_read_cost if monthly is not None else None,
+        monthly_cache_creation_cost=monthly.cache_creation_cost if monthly is not None else None,
+        monthly_reasoning_cost=monthly.reasoning_cost if monthly is not None else None,
+        input_cost_per_token=rates.input_cost_per_token if rates is not None else None,
+        output_cost_per_token=rates.output_cost_per_token if rates is not None else None,
+        cache_read_input_token_cost=rates.cache_read_input_token_cost if rates is not None else None,
+        cache_creation_input_token_cost=rates.cache_creation_input_token_cost if rates is not None else None,
+        output_cost_per_reasoning_token=rates.output_cost_per_reasoning_token if rates is not None else None,
         provider=custom_llm_provider,
     )
diff --git a/litellm/proxy/management_endpoints/key_management_endpoints.py b/litellm/proxy/management_endpoints/key_management_endpoints.py
index f46c4170071..749a940de0e 100644
--- a/litellm/proxy/management_endpoints/key_management_endpoints.py
+++ b/litellm/proxy/management_endpoints/key_management_endpoints.py
@@ -4559,6 +4559,23 @@ async def delete_verification_tokens(
                 litellm_changed_by=litellm_changed_by,
             )
 
+            # Snapshot before the delete: the FK cascade drops the mapping rows, but their
+            # cached jwt_key_mapping entries still resolve to the now-dead token (LIT-5380).
+            jwt_mapping_cache_keys: Final[tuple[str, ...]] = tuple(
+                cache_key
+                for keys_for_token in await asyncio.gather(
+                    *(
+                        get_jwt_key_mapping_cache_keys_for_token(
+                            hashed_token=key.token,
+                            prisma_client=prisma_client,
+                        )
+                        for key in authorized_keys
+                        if key.token is not None
+                    )
+                )
+                for cache_key in keys_for_token
+            )
+
             if user_api_key_dict.user_role == LitellmUserRoles.PROXY_ADMIN.value:
                 deleted_tokens = await prisma_client.delete_data(tokens=tokens)
                 if deleted_tokens is not None and len(deleted_tokens) != len(tokens):
@@ -4571,6 +4588,8 @@ async def delete_verification_tokens(
                 if len(deleted_tokens) != len(tokens):
                     failed_tokens = [token for token in tokens if token not in deleted_tokens]
 
+            await evict_and_broadcast(cache_keys=jwt_mapping_cache_keys, user_api_key_cache=user_api_key_cache)
+
         else:
             raise Exception("DB not connected. prisma_client is None")
     except Exception as e:
diff --git a/litellm/proxy/management_endpoints/mcp_management_endpoints.py b/litellm/proxy/management_endpoints/mcp_management_endpoints.py
index d5c3427f29a..4c97bbaf5de 100644
--- a/litellm/proxy/management_endpoints/mcp_management_endpoints.py
+++ b/litellm/proxy/management_endpoints/mcp_management_endpoints.py
@@ -2278,6 +2278,28 @@ if MCP_AVAILABLE:
         """Persist the OAuth2 access token obtained by the calling user."""
         prisma_client: Final = get_prisma_client_or_throw("Database not connected. Connect a database to your proxy")
         await _authorize_and_fetch_mcp_server(prisma_client, user_api_key_dict, server_id)
+        from litellm.proxy._experimental.mcp_server.mcp_server_manager import (  # noqa: PLC0415  # keep manager import lazy
+            global_mcp_server_manager as _manager,
+        )
+
+        # This endpoint accepts an opaque token with no upstream identity validation, so it must be
+        # closed for identity-bound servers or it becomes a bypass of the token-relay binding check.
+        registry_server: Final = _manager.get_mcp_server_by_id(server_id)
+        binding: Final = registry_server.oauth_identity_binding if registry_server else None
+        if binding is not None and binding.mode == "enforce":
+            raise HTTPException(
+                status_code=status.HTTP_403_FORBIDDEN,
+                detail={  # mutable-ok: FastAPI exception detail requires a JSON-serializable dictionary
+                    "error": "oauth_identity_binding_enforced",
+                    "error_description": (
+                        "Direct credential storage is disabled for this server: its OAuth identity "
+                        "binding is enforced and this endpoint cannot validate the token's principal. "
+                        "Complete the OAuth flow through the gateway instead."
+                    ),
+                    "server_id": server_id,
+                    "credential_stored": False,
+                },
+            )
         user_id: Final = user_api_key_dict.user_id or ""
         if not user_id:
             raise HTTPException(
@@ -2673,6 +2695,8 @@ if MCP_AVAILABLE:
         """
         Updates the MCP Server in the db.
 
+        Partial update: a field left out of the payload keeps its stored value, and a field sent as null is cleared.
+
         Parameters:
         - payload: UpdateMCPServerRequest - Required. The updated mcp server data.
         ```
@@ -3098,6 +3122,8 @@ if MCP_AVAILABLE:
         user_api_key_dict: UserAPIKeyAuth = Depends(user_api_key_auth),
         litellm_changed_by: str | None = Header(None),
     ):
+        """Partial update: a field left out keeps its stored value, and a field sent as null is cleared, except
+        ``toolset_name`` and ``tools``, which a toolset always has; empty the tool selection with an explicit []."""
         prisma_client: Final = get_prisma_client_or_throw("Database not connected. Connect a database to your proxy")
         if LitellmUserRoles.PROXY_ADMIN != user_api_key_dict.user_role:
             raise HTTPException(
diff --git a/litellm/proxy/management_endpoints/model_management_endpoints.py b/litellm/proxy/management_endpoints/model_management_endpoints.py
index 0f19e9ce149..94d2b773e14 100644
--- a/litellm/proxy/management_endpoints/model_management_endpoints.py
+++ b/litellm/proxy/management_endpoints/model_management_endpoints.py
@@ -111,6 +111,7 @@ from litellm.router_utils.auto_router_model_naming import (
     validate_strategy_router_model_write,
 )
 from litellm.router_utils.auto_router_tuning_baseline import is_mutable_tuned_candidate, tuning_quota_violation
+from litellm.types.llms.bedrock import AwsSessionTag
 from litellm.types.proxy.management_endpoints.model_management_endpoints import (
     AutoRouterClassifierDefaultPromptResponse,
     UpdateUsefulLinksRequest,
@@ -897,6 +898,12 @@ async def patch_model(
             existing_litellm_params=db_model.litellm_params,
         )
 
+        ModelManagementAuthChecks.can_user_set_aws_session_tags(
+            litellm_params=patch_data.litellm_params,
+            user_api_key_dict=user_api_key_dict,
+            existing_litellm_params=db_model.litellm_params,
+        )
+
         _raise_on_strategy_router_write_violation(
             incoming_params=patch_data.litellm_params,
             existing_params=db_model.litellm_params,
@@ -1650,6 +1657,10 @@ async def _update_existing_team_model_assignment(
     # No team_model_add/delete calls required; public name is already registered
 
 
+def _canonical_session_tags(tags: Sequence[AwsSessionTag]) -> tuple[tuple[str, str], ...]:
+    return tuple(sorted((tag["Key"], tag["Value"]) for tag in tags))
+
+
 class ModelManagementAuthChecks:
     """
     Common auth checks for model management endpoints
@@ -1704,6 +1715,28 @@ class ModelManagementAuthChecks:
             param="litellm_credential_name",
         )
 
+    @staticmethod
+    def can_user_set_aws_session_tags(
+        litellm_params: GenericLiteLLMParams | None,
+        user_api_key_dict: UserAPIKeyAuth,
+        existing_litellm_params: GenericLiteLLMParams | None = None,
+    ) -> Literal[True]:
+        if litellm_params is None or litellm_params.aws_session_tags is None:
+            return True
+        if user_api_key_dict.user_role == LitellmUserRoles.PROXY_ADMIN:
+            return True
+        existing_tags: Final = existing_litellm_params.aws_session_tags if existing_litellm_params is not None else None
+        if existing_tags is not None and _canonical_session_tags(existing_tags) == _canonical_session_tags(
+            litellm_params.aws_session_tags
+        ):
+            return True
+        raise ProxyException(
+            message=f"Only a proxy admin can set aws_session_tags on a model. Your role={user_api_key_dict.user_role}.",
+            type=ProxyErrorTypes.auth_error.value,
+            code=status.HTTP_403_FORBIDDEN,
+            param="aws_session_tags",
+        )
+
     @staticmethod
     async def allow_team_model_action(
         model_params: Deployment | updateDeployment,
@@ -2037,6 +2070,11 @@ async def add_new_model(
             user_api_key_dict=user_api_key_dict,
         )
 
+        ModelManagementAuthChecks.can_user_set_aws_session_tags(
+            litellm_params=model_params.litellm_params,
+            user_api_key_dict=user_api_key_dict,
+        )
+
         _raise_on_strategy_router_write_violation(
             incoming_params=model_params.litellm_params,
             existing_params=None,
@@ -2221,6 +2259,12 @@ async def update_model(
             existing_litellm_params=deployment.litellm_params,
         )
 
+        ModelManagementAuthChecks.can_user_set_aws_session_tags(
+            litellm_params=model_params.litellm_params,
+            user_api_key_dict=user_api_key_dict,
+            existing_litellm_params=deployment.litellm_params,
+        )
+
         _raise_on_strategy_router_write_violation(
             incoming_params=model_params.litellm_params,
             existing_params=deployment.litellm_params,
diff --git a/litellm/proxy/management_endpoints/organization_endpoints.py b/litellm/proxy/management_endpoints/organization_endpoints.py
index 1e711b036d2..96e946424bd 100644
--- a/litellm/proxy/management_endpoints/organization_endpoints.py
+++ b/litellm/proxy/management_endpoints/organization_endpoints.py
@@ -80,7 +80,23 @@ if TYPE_CHECKING:
     from prisma.models import LiteLLM_OrganizationTable as PrismaOrganizationTable
     from prisma.models import LiteLLM_UserTable as PrismaUserTable
 
-router: Final = APIRouter()
+
+async def _enterprise_license_required(
+    _user_api_key_dict: Annotated[UserAPIKeyAuth, Depends(user_api_key_auth)],
+) -> None:
+    from litellm.proxy.proxy_server import premium_user
+
+    if not premium_user:
+        raise HTTPException(
+            status_code=403,
+            detail={
+                "error": "Organizations are only available for LiteLLM Enterprise users. "
+                f"{CommonProxyErrors.not_premium_user.value}"
+            },
+        )
+
+
+router: Final = APIRouter(dependencies=[Depends(_enterprise_license_required)])
 
 
 class _ObjectPermissionRow(Protocol):
diff --git a/litellm/proxy/management_endpoints/team_endpoints.py b/litellm/proxy/management_endpoints/team_endpoints.py
index 2ec68a10f65..c050368b3fe 100644
--- a/litellm/proxy/management_endpoints/team_endpoints.py
+++ b/litellm/proxy/management_endpoints/team_endpoints.py
@@ -5601,7 +5601,7 @@ async def team_model_add(
     updated_team: Final = await _team_db(prisma_client).update(
         where={"team_id": data.team_id},
         data={"updated_at": datetime.now(timezone.utc)},
-        include={"object_permission": True},
+        include={"litellm_model_table": True, "object_permission": True},
     )
     if updated_team is None:
         raise HTTPException(
@@ -5688,7 +5688,7 @@ async def team_model_delete(
     updated_team: Final = await _team_db(prisma_client).update(
         where={"team_id": data.team_id},
         data={"models": updated_models},
-        include={"object_permission": True},
+        include={"litellm_model_table": True, "object_permission": True},
     )
     if updated_team is None:
         raise HTTPException(
diff --git a/litellm/proxy/management_endpoints/ui_sso.py b/litellm/proxy/management_endpoints/ui_sso.py
index 3e6434a5afd..1ba90725eff 100644
--- a/litellm/proxy/management_endpoints/ui_sso.py
+++ b/litellm/proxy/management_endpoints/ui_sso.py
@@ -22,7 +22,6 @@ from html import escape
 from types import MappingProxyType
 from typing import (
     TYPE_CHECKING,
-    Annotated,
     Any,
     Final,
     Literal,
@@ -42,12 +41,13 @@ if TYPE_CHECKING:
 import jwt
 from fastapi import APIRouter, Depends, Header, HTTPException, Request, Response, status
 from fastapi.responses import RedirectResponse
-from pydantic import BaseModel, BeforeValidator, ConfigDict, TypeAdapter, ValidationError
+from pydantic import BaseModel, TypeAdapter, ValidationError
 
 import litellm
 from litellm._logging import verbose_proxy_logger
 from litellm._uuid import uuid
 from litellm.caching.dual_cache import DualCache
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 from litellm.constants import (
     CLI_SSO_CLAIM_MAP,
     CLI_SSO_CLAIM_MAX_SCALAR_LENGTH,
@@ -95,6 +95,7 @@ from litellm.proxy.auth.auth_utils import (
 )
 from litellm.proxy.auth.handle_jwt import JWTHandler
 from litellm.proxy.auth.ip_address_utils import IPAddressUtils
+from litellm.proxy.auth.team_grants import TeamModelAliasTable
 from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
 from litellm.proxy.common_utils.admin_ui_utils import (
     admin_ui_disabled,
@@ -209,31 +210,14 @@ def _team_detail_db(repo: TeamRepository) -> "TableActions[_TeamDetailRow]":
     return repo.table
 
 
-_MODEL_ALIASES_ADAPTER: Final = TypeAdapter(dict[str, str])
 _SSO_TOKEN_CLAIMS_ADAPTER: Final = TypeAdapter(Mapping[str, object])
 
 
-def _decode_model_aliases(value: object) -> object:
-    """``/team/new`` stores team model aliases as a JSON-encoded string in the Json column."""
-    if not isinstance(value, str):
-        return value
-    try:
-        return _MODEL_ALIASES_ADAPTER.validate_json(value)
-    except ValidationError:
-        return None
-
-
-class _TeamModelAliasTable(BaseModel):
-    model_config = ConfigDict(protected_namespaces=())
-
-    model_aliases: Annotated[Mapping[str, str] | None, BeforeValidator(_decode_model_aliases)] = None
-
-
 class _TeamRowGrants(BaseModel):
     team_id: str
     team_alias: str | None = None
     models: tuple[str, ...] = ()
-    litellm_model_table: _TeamModelAliasTable | None = None
+    litellm_model_table: TeamModelAliasTable | None = None
 
 
 class CliSsoTeamDetail(BaseModel):
@@ -353,6 +337,16 @@ def _check_cli_sso_start_rate_limit(
         )
 
 
+def _read_cli_sso_flow(cache: DualCache, cache_key: str) -> object:
+    redis_cache: Final = cache.redis_cache
+    if redis_cache is None:
+        return cache.get_cache(key=cache_key)
+    try:
+        return redis_cache.get_cache(key=cache_key)
+    except RedisCircuitBreakerOpenError:
+        return None
+
+
 def _get_cli_sso_flow_or_raise(login_id: str | None, cache: DualCache) -> dict:
     if isinstance(login_id, str) and login_id.startswith("sk-"):
         raise HTTPException(
@@ -365,12 +359,7 @@ def _get_cli_sso_flow_or_raise(login_id: str | None, cache: DualCache) -> dict:
     if not _is_valid_cli_sso_login_id(login_id):
         raise HTTPException(status_code=400, detail="Invalid CLI login session id")
 
-    cache_key: Final = _get_cli_sso_flow_cache_key(cast(str, login_id))
-    redis_cache: Final = cache.redis_cache
-    if redis_cache is not None:
-        flow = redis_cache.get_cache(key=cache_key)
-    else:
-        flow = cache.get_cache(key=cache_key)
+    flow = _read_cli_sso_flow(cache, _get_cli_sso_flow_cache_key(cast(str, login_id)))
     if isinstance(flow, str):
         try:
             flow = _as_object(json.loads(flow))
diff --git a/litellm/proxy/pass_through_endpoints/llm_passthrough_endpoints.py b/litellm/proxy/pass_through_endpoints/llm_passthrough_endpoints.py
index 2ea46b740a8..face515ef88 100644
--- a/litellm/proxy/pass_through_endpoints/llm_passthrough_endpoints.py
+++ b/litellm/proxy/pass_through_endpoints/llm_passthrough_endpoints.py
@@ -15,6 +15,7 @@ import os
 import re
 from collections.abc import AsyncGenerator, Callable, Mapping, Sequence
 from dataclasses import dataclass
+from functools import partial
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Annotated, Final, Literal, Protocol, cast
 
@@ -33,6 +34,7 @@ from litellm.constants import (
 )
 from litellm.litellm_core_utils.aws_partition import get_aws_dns_suffix
 from litellm.llms.anthropic.common_utils import AnthropicModelInfo
+from litellm.llms.azure.passthrough.transformation import foreign_azure_deployment
 from litellm.llms.custom_httpx.http_handler import get_async_httpx_client
 from litellm.llms.vertex_ai.vertex_llm_base import VertexBase
 from litellm.passthrough.main import AsyncPassthroughStreamingResponse
@@ -52,6 +54,7 @@ from litellm.proxy.common_utils.http_parsing_utils import (
     _safe_set_request_parsed_body,
     get_form_data,
     get_request_body,
+    is_json_content_type,
 )
 from litellm.proxy.common_utils.sse_keepalive import (
     wrap_passthrough_sse_bytes_with_keepalive_pings,
@@ -77,6 +80,7 @@ from litellm.types.passthrough_endpoints.pass_through_endpoints import (
     LITELLM_PASS_THROUGH_RAW_BODY_STATE_KEY,
 )
 from litellm.types.passthrough_endpoints.vertex_ai import VertexPassThroughCredentials
+from litellm.types.router import LiteLLMParamsTypedDict
 from litellm.types.utils import LlmProviders
 from litellm.types.vector_stores import LiteLLM_ManagedVectorStore
 from litellm.utils import ProviderConfigManager
@@ -119,6 +123,24 @@ def is_passthrough_request_using_router_model(request_body: dict, llm_router: li
         return False
 
 
+class RelayRejection(TypedDict):
+    error: ReadOnly[str]
+
+
+def _deployment_model_name(litellm_params: LiteLLMParamsTypedDict) -> str:
+    model: Final = litellm_params.get("model", "")
+    try:
+        return get_llm_provider(model=model, custom_llm_provider=litellm_params.get("custom_llm_provider"))[0]
+    except litellm.BadRequestError:
+        return model
+
+
+def _models_served_by_group(llm_router: litellm.Router, model_group: str) -> frozenset[str]:
+    return frozenset(
+        _deployment_model_name(row["litellm_params"]) for row in llm_router.get_model_list(model_name=model_group) or ()
+    )
+
+
 def is_passthrough_request_streaming(request_body: object) -> bool:
     """
     Returns True if the request is streaming.
@@ -411,7 +433,7 @@ async def vllm_proxy_route(
                 content=None,
                 data=None,
                 files=None,
-                json=(request_body if request.headers.get("content-type") == "application/json" else None),
+                json=(request_body if is_json_content_type(request.headers.get("content-type", "")) else None),
                 params=None,
                 headers=None,
                 cookies=None,
@@ -1099,13 +1121,6 @@ async def bedrock_proxy_route(
     """
     create_request_copy(request)
 
-    try:
-        from botocore.auth import SigV4Auth
-        from botocore.awsrequest import AWSRequest
-        from botocore.credentials import Credentials
-    except ImportError:
-        raise ImportError("Missing boto3 to call bedrock. Run 'pip install boto3'.")
-
     aws_region_name: Final = get_secret_str(secret_name="AWS_REGION_NAME")
     if not _is_bedrock_agent_runtime_route(endpoint=endpoint):
         return await bedrock_llm_proxy_route(
@@ -1136,20 +1151,24 @@ async def bedrock_proxy_route(
     )
 
     # Add or update query parameters
+    from litellm.llms.bedrock.base_aws_llm import run_aws_signing, sign_aws_json_post
     from litellm.llms.bedrock.chat import BedrockConverseLLM
 
     bedrock_llm: Final = BedrockConverseLLM()
-    credentials: Final[Credentials] = bedrock_llm.get_credentials()
-    sigv4: Final = SigV4Auth(credentials, "bedrock", aws_region_name)
-    headers: Final = {"Content-Type": "application/json"}
     # Assuming the body contains JSON data, parse it
     try:
         data: Final = await _json_request_body(request)
     except Exception as e:
         raise HTTPException(status_code=400, detail={"error": e})
-    _request: Final = AWSRequest(method="POST", url=str(updated_url), data=json.dumps(data), headers=headers)
-    sigv4.add_auth(_request)
-    prepped: Final = _request.prepare()
+    prepped: Final = await run_aws_signing(
+        sign_aws_json_post,
+        get_credentials=bedrock_llm.get_credentials,
+        service_name="bedrock",
+        aws_region_name=aws_region_name,
+        url=str(updated_url),
+        body=json.dumps(data),
+        headers=MappingProxyType({"Content-Type": "application/json"}),
+    )
 
     ## check for streaming
     is_streaming_request = False
@@ -1207,13 +1226,6 @@ async def comprehend_medical_proxy_route(
 
     [Docs](https://docs.litellm.ai/docs/pass_through/comprehend_medical)
     """
-    try:
-        from botocore.auth import SigV4Auth
-        from botocore.awsrequest import AWSRequest
-        from botocore.credentials import Credentials
-    except ImportError:
-        raise ImportError("Missing boto3 to call comprehendmedical. Run 'pip install boto3'.")
-
     from .llm_provider_handlers.comprehend_medical_passthrough_logging_handler import (
         COMPREHEND_MEDICAL_SUPPORTED_OPERATIONS,
     )
@@ -1244,20 +1256,23 @@ async def comprehend_medical_proxy_route(
     if "stream" in data:
         raise HTTPException(status_code=400, detail="'stream' is not a Comprehend Medical request member")
 
-    from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM
+    from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM, run_aws_signing, sign_aws_json_post
 
-    credentials: Final[Credentials] = BaseAWSLLM().get_credentials(aws_region_name=aws_region_name)
-    sigv4: Final = SigV4Auth(credentials, "comprehendmedical", aws_region_name)
-    headers: Final = MappingProxyType(
-        {
-            "Content-Type": "application/x-amz-json-1.1",
-            "X-Amz-Target": f"{COMPREHEND_MEDICAL_TARGET_PREFIX}.{operation}",
-        }
-    )
     target_url: Final = f"https://comprehendmedical.{aws_region_name}.{get_aws_dns_suffix(aws_region_name)}/"
-    _request: Final = AWSRequest(method="POST", url=target_url, data=json.dumps(data), headers=headers)
-    sigv4.add_auth(_request)
-    prepped: Final = _request.prepare()
+    prepped: Final = await run_aws_signing(
+        sign_aws_json_post,
+        get_credentials=partial(BaseAWSLLM().get_credentials, aws_region_name=aws_region_name),
+        service_name="comprehendmedical",
+        aws_region_name=aws_region_name,
+        url=target_url,
+        body=json.dumps(data),
+        headers=MappingProxyType(
+            {
+                "Content-Type": "application/x-amz-json-1.1",
+                "X-Amz-Target": f"{COMPREHEND_MEDICAL_TARGET_PREFIX}.{operation}",
+            }
+        ),
+    )
 
     endpoint_func: Final = create_pass_through_route(
         endpoint=operation,
@@ -1505,6 +1520,14 @@ async def _relay_upstream_bytes(upstream: AsyncGenerator[bytes, bytes]) -> Async
         await upstream.aclose()
 
 
+async def _relay_upstream_response(upstream: httpx.Response) -> Response:
+    return Response(
+        content=await upstream.aread(),
+        status_code=upstream.status_code,
+        headers=HttpPassThroughEndpointHelpers.get_response_headers(headers=upstream.headers, custom_headers=None),
+    )
+
+
 async def _relay_azure_router_model(
     llm_router: litellm.Router,
     model: str,
@@ -1514,30 +1537,37 @@ async def _relay_azure_router_model(
     is_streaming_request: bool,
     user_api_key_dict: UserAPIKeyAuth,
 ) -> Response:
-    result: Final = await llm_router.allm_passthrough_route(
-        model=model,
-        method=request.method,
-        endpoint=endpoint,
-        request_query_params=request.query_params,
-        request_headers=_safe_get_request_headers(request),
-        stream=is_streaming_request,
-        content=None,
-        data=None,
-        files=None,
-        json=(request_body if request.headers.get("content-type") == "application/json" else None),
-        params=None,
-        headers=None,
-        cookies=None,
-        litellm_metadata=get_passthrough_router_request_metadata(user_api_key_dict),
+    foreign_deployment: Final = foreign_azure_deployment(
+        endpoint, model, lambda: _models_served_by_group(llm_router, model)
     )
+    if foreign_deployment is not None:
+        rejection: Final[RelayRejection] = {
+            "error": f"deployment '{foreign_deployment}' in the path is not served by model group '{model}'; "
+            "put the model group name in the deployments segment"
+        }
+        raise HTTPException(status_code=400, detail=rejection)
+    try:
+        result: Final = await llm_router.allm_passthrough_route(
+            model=model,
+            method=request.method,
+            endpoint=endpoint,
+            request_query_params=request.query_params,
+            request_headers=_safe_get_request_headers(request),
+            stream=is_streaming_request,
+            content=None,
+            data=None,
+            files=None,
+            json=(request_body if is_json_content_type(request.headers.get("content-type", "")) else None),
+            params=None,
+            headers=None,
+            cookies=None,
+            litellm_metadata=get_passthrough_router_request_metadata(user_api_key_dict),
+        )
+    except httpx.HTTPStatusError as upstream_error:
+        return await _relay_upstream_response(upstream_error.response)
 
     if not is_streaming_request:
-        upstream: Final = cast(httpx.Response, result)
-        return Response(
-            content=await upstream.aread(),
-            status_code=upstream.status_code,
-            headers=HttpPassThroughEndpointHelpers.get_response_headers(headers=upstream.headers, custom_headers=None),
-        )
+        return await _relay_upstream_response(cast(httpx.Response, result))
 
     if inspect.isasyncgen(result):
         sse_headers: Final = {"content-type": "text/event-stream"}
diff --git a/litellm/proxy/pass_through_endpoints/llm_provider_handlers/openai_passthrough_logging_handler.py b/litellm/proxy/pass_through_endpoints/llm_provider_handlers/openai_passthrough_logging_handler.py
index 5f6489a69ca..93fe3c5b31b 100644
--- a/litellm/proxy/pass_through_endpoints/llm_provider_handlers/openai_passthrough_logging_handler.py
+++ b/litellm/proxy/pass_through_endpoints/llm_provider_handlers/openai_passthrough_logging_handler.py
@@ -4,6 +4,7 @@ OpenAI Passthrough Logging Handler
 Handles cost tracking and logging for OpenAI passthrough endpoints, specifically /chat/completions.
 """
 
+from collections.abc import Mapping, Sequence
 from datetime import datetime
 from typing import Final
 from urllib.parse import urlparse
@@ -16,6 +17,7 @@ from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLogging
 from litellm.litellm_core_utils.litellm_logging import (
     get_standard_logging_object_payload,
 )
+from litellm.litellm_core_utils.token_counter import high_detail_image_token_upper_bound
 from litellm.llms.openai.openai import OpenAIConfig
 from litellm.llms.openai.openai import OpenAIConfig as OpenAIConfigType
 from litellm.llms.openai.responses.transformation import OpenAIResponsesAPIConfig
@@ -96,6 +98,47 @@ def _is_openai_compatible_url(url_route: str | None) -> bool:
     return False
 
 
+def _is_remote_high_detail_image(part: object) -> bool:
+    if not isinstance(part, Mapping) or part.get("type") != "image_url":
+        return False
+    image_url: Final = part.get("image_url")
+    if not isinstance(image_url, Mapping):
+        return False
+    url: Final = image_url.get("url")
+    return (
+        isinstance(url, str) and url.lower().startswith(("http://", "https://")) and image_url.get("detail") == "high"
+    )
+
+
+def _content_parts(message: Mapping[str, object]) -> Sequence[object]:
+    content: Final = message.get("content")
+    return content if isinstance(content, list) else ()
+
+
+def _without_remote_high_detail_images(message: Mapping[str, object]) -> Mapping[str, object]:
+    if not isinstance(message.get("content"), list):
+        return message
+    kept_parts: Final = [  # mutable-ok: token_counter reads message content only when it is a list
+        part for part in _content_parts(message) if not _is_remote_high_detail_image(part)
+    ]
+    return {**message, "content": kept_parts}  # mutable-ok: token_counter rejects any message that is not a dict
+
+
+def count_relayed_prompt_tokens(model: str, messages: Sequence[Mapping[str, object]] | None) -> int:
+    if messages is None:
+        return 0
+    remote_high_detail_images: Final = sum(
+        1 for message in messages for part in _content_parts(message) if _is_remote_high_detail_image(part)
+    )
+    local_messages: Final = [  # mutable-ok: token_counter takes a list of messages
+        _without_remote_high_detail_images(message) for message in messages
+    ]
+    return (
+        litellm.token_counter(model=model, messages=local_messages)
+        + high_detail_image_token_upper_bound() * remote_high_detail_images
+    )
+
+
 class OpenAIPassthroughLoggingHandler(BasePassthroughLoggingHandler):
     """
     OpenAI-specific passthrough logging handler that provides cost tracking for /chat/completions endpoints.
@@ -512,9 +555,10 @@ class OpenAIPassthroughLoggingHandler(BasePassthroughLoggingHandler):
 
     def _build_complete_streaming_response(
         self,
-        all_chunks: list[str],
+        all_chunks: Sequence[str],
         litellm_logging_obj: LiteLLMLoggingObj,
         model: str,
+        messages: Sequence[Mapping[str, object]] | None = None,
     ) -> ModelResponse | TextCompletionResponse | None:
         """
         Builds complete response from raw chunks for OpenAI streaming responses.
@@ -558,7 +602,11 @@ class OpenAIPassthroughLoggingHandler(BasePassthroughLoggingHandler):
                 return None
 
             # Build complete response from chunks
-            complete_streaming_response: Final = litellm.stream_chunk_builder(chunks=all_openai_chunks)
+            complete_streaming_response: Final = litellm.stream_chunk_builder(
+                chunks=all_openai_chunks,
+                messages=messages,
+                count_prompt_tokens=lambda: count_relayed_prompt_tokens(model, messages),
+            )
 
             return complete_streaming_response
 
diff --git a/litellm/proxy/policy_engine/pipeline_executor.py b/litellm/proxy/policy_engine/pipeline_executor.py
index 7bcb79cefc9..ed193c7f434 100644
--- a/litellm/proxy/policy_engine/pipeline_executor.py
+++ b/litellm/proxy/policy_engine/pipeline_executor.py
@@ -70,6 +70,10 @@ def _text_snapshot(texts: Sequence[str] | None) -> tuple[str, ...] | None:
     return None if texts is None else tuple(texts)
 
 
+def _scanned_texts(texts: Sequence[str] | None) -> tuple[str, ...]:
+    return tuple(texts or ())
+
+
 def _tool_call_shapes(tool_calls: Sequence[object] | None) -> tuple[tuple[object, object], ...] | None:
     return None if tool_calls is None else tuple(_tool_call_shape(tool_call) for tool_call in tool_calls)
 
@@ -78,6 +82,10 @@ def _rewrote(sent: tuple[object, ...] | None, returned: tuple[object, ...] | Non
     return sent is not None and returned is not None and returned != sent
 
 
+def _changed_count(sent: tuple[object, ...] | None, returned: tuple[object, ...] | None) -> bool:
+    return sent is not None and returned is not None and len(returned) != len(sent)
+
+
 _GuardrailMethodT = TypeVar("_GuardrailMethodT", bound=Callable[..., object])
 
 
@@ -89,10 +97,11 @@ def _logged_by_inner_guardrail(method: _GuardrailMethodT) -> _GuardrailMethodT:
 class _StreamRewriteObserver(CustomGuardrail):
     """Stand-in handed to the endpoint translation in place of a streaming pipeline step's
     guardrail. It records whether the guardrail returned different output than it was given,
-    which for guardrails like Bedrock's ANONYMIZED action is only known at runtime. Text
-    rewrites are deliverable on translations that write them back across the buffered chunks
-    (``delivers_ended_stream_text_rewrites``); tool-call rewrites and text rewrites on any
-    other translation are discarded by the executor, which releases the original chunks.
+    which for guardrails like Bedrock's ANONYMIZED action is only known at runtime. Text and
+    tool-call rewrites are deliverable on translations that write them back across the
+    buffered chunks (``delivers_ended_stream_rewrites``); rewrites on any other translation,
+    and a rewrite that drops or adds a tool call on any translation, are discarded by the
+    executor, which releases the original chunks.
     The inner guardrail's ``apply_guardrail`` already records the guardrail information
     and span, so the observer's stays out of ``log_guardrail_information``."""
 
@@ -101,6 +110,7 @@ class _StreamRewriteObserver(CustomGuardrail):
         self.inner: Final = inner
         self.rewrote_texts = False
         self.rewrote_tool_calls = False
+        self.changed_tool_call_count = False
 
     def structured_messages_cover_full_request(self) -> bool:
         return self.inner.structured_messages_cover_full_request()
@@ -118,13 +128,103 @@ class _StreamRewriteObserver(CustomGuardrail):
         outputs: Final = await self.inner.apply_guardrail(
             inputs=inputs, request_data=request_data, input_type=input_type, logging_obj=logging_obj
         )
+        returned_tool_shapes: Final = _tool_call_shapes(outputs.get("tool_calls"))
         self.rewrote_texts = self.rewrote_texts or _rewrote(sent_texts, _text_snapshot(outputs.get("texts")))
-        self.rewrote_tool_calls = self.rewrote_tool_calls or _rewrote(
-            sent_tool_shapes, _tool_call_shapes(outputs.get("tool_calls"))
+        self.rewrote_tool_calls = self.rewrote_tool_calls or _rewrote(sent_tool_shapes, returned_tool_shapes)
+        self.changed_tool_call_count = self.changed_tool_call_count or _changed_count(
+            sent_tool_shapes, returned_tool_shapes
         )
         return outputs
 
 
+class _ScannedTextRecorder(CustomGuardrail):
+    def __init__(self, guardrail_name: str) -> None:
+        super().__init__(guardrail_name=guardrail_name)
+        self.inputs: GenericGuardrailAPIInputs | None = None
+
+    @_logged_by_inner_guardrail
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict,  # mutable-ok: matches CustomGuardrail.apply_guardrail
+        input_type: Literal["request", "response"],
+        logging_obj: "LiteLLMLoggingObj | None" = None,
+    ) -> GenericGuardrailAPIInputs:
+        self.inputs = inputs
+        return inputs
+
+
+class _LegacyHookStreamAdapter(CustomGuardrail):
+    """Runs a guardrail that only implements the legacy post-call hook (no unified
+    ``apply_guardrail``, or ``use_native_lifecycle_hooks``) as a streaming pipeline step. The
+    endpoint translation hands it the texts it scanned plus the assembled response under
+    ``request_data["response"]``; the hook gets that response in the shape its route gives
+    non-streaming hooks, an exception it raises ends the stream through the executor's
+    fail/error classification, and the response it hands back, or the one it changed in place
+    and returned ``None`` for, is re-scanned by the same translation so its texts reach the
+    client through the translation's ended-stream write-back. A
+    replacement whose scanned texts do not line up with the originals, or whose tool calls
+    differ from them, is undeliverable, so the executor releases the original chunks. A stream
+    that carried no text to scan, such as a tool-only Anthropic message, stays deliverable as
+    long as the hook left the tool calls alone."""
+
+    def __init__(
+        self,
+        inner: CustomGuardrail,
+        endpoint_translation: "BaseTranslation",
+        user_api_key_dict: "UserAPIKeyAuth",
+    ) -> None:
+        super().__init__(guardrail_name=inner.guardrail_name)
+        self.inner: Final = inner
+        self.endpoint_translation: Final = endpoint_translation
+        self.user_api_key_dict: Final = user_api_key_dict
+
+    def structured_messages_cover_full_request(self) -> bool:
+        return self.inner.structured_messages_cover_full_request()
+
+    @_logged_by_inner_guardrail
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict,  # mutable-ok: matches CustomGuardrail.apply_guardrail
+        input_type: Literal["request", "response"],
+        logging_obj: "LiteLLMLoggingObj | None" = None,
+    ) -> GenericGuardrailAPIInputs:
+        hooked: Final = self.endpoint_translation.post_call_hook_response(request_data.get("response"))
+        replacement: Final = await self.inner.async_post_call_success_hook(
+            data=request_data,
+            user_api_key_dict=self.user_api_key_dict,
+            response=hooked,
+        )
+        rewrite: Final = hooked if replacement is None else replacement
+        if rewrite is None:
+            return inputs
+        rescanned: Final = await self._rescan(rewrite, logging_obj)
+        if rescanned is None:
+            raise UndeliverableStreamRewrite(self.guardrail_name or "unknown")
+        rewritten: Final = rescanned.get("texts")
+        if len(_scanned_texts(rewritten)) != len(_scanned_texts(inputs.get("texts"))):
+            raise UndeliverableStreamRewrite(self.guardrail_name or "unknown")
+        if _tool_call_shapes(rescanned.get("tool_calls")) != _tool_call_shapes(inputs.get("tool_calls")):
+            raise UndeliverableStreamRewrite(self.guardrail_name or "unknown")
+        if not rewritten:
+            return inputs
+        rewritten_inputs: Final[GenericGuardrailAPIInputs] = {**inputs, "texts": rewritten}
+        return rewritten_inputs
+
+    async def _rescan(
+        self, response: object, logging_obj: "LiteLLMLoggingObj | None"
+    ) -> GenericGuardrailAPIInputs | None:
+        recorder: Final = _ScannedTextRecorder(self.guardrail_name or "unknown")
+        await self.endpoint_translation.process_output_response(
+            response=response,
+            guardrail_to_apply=recorder,
+            litellm_logging_obj=logging_obj,
+            user_api_key_dict=self.user_api_key_dict,
+        )
+        return recorder.inputs
+
+
 def _prepare_hook_input(
     step: PipelineStep,
     callback: CustomGuardrail,
@@ -292,18 +392,29 @@ class PipelineExecutor:
         endpoint_translation: "BaseTranslation",
         streaming_chunks: list[object],  # mutable-ok: shared buffered-stream chunks the translation rewrites in place
         hook_input: dict[str, object],  # mutable-ok: same request-payload shape as data
-        user_api_key_dict: "UserAPIKeyAuth | None",
+        user_api_key_dict: "UserAPIKeyAuth",
         litellm_logging_obj: "LiteLLMLoggingObj | None",
     ) -> None:
         """Run one streaming post_call step through the endpoint translation, delivering
-        text rewrites on translations that support ended-stream write-back. A rewrite that
-        cannot reach the client yet (a tool-call rewrite, a text rewrite on a translation
-        without write-back, or one the translation refused with
-        ``UndeliverableStreamRewrite``) is discarded: the buffered chunks go back to the
-        originals and the step passes, so the client gets the stream the merge base sent."""
-        observer: Final = _StreamRewriteObserver(callback)
-        deliver_rewrites: Final = type(endpoint_translation).delivers_ended_stream_text_rewrites
+        text and tool-call rewrites on translations that support ended-stream write-back. A
+        guardrail without the unified interface runs its legacy post-call hook against the
+        assembled response through ``_LegacyHookStreamAdapter``. A rewrite that cannot reach the
+        client yet (one on a translation without write-back, one that drops or adds a tool call,
+        or one the translation or adapter refused with ``UndeliverableStreamRewrite``) is
+        discarded: the buffered chunks go back to the originals and the step passes, so the
+        client gets the stream the merge base sent, and the guardrail stays out of the
+        applied-guardrails header since its output never reached the client. The response an
+        earlier step's translation stored under ``request_data["response"]`` is dropped first,
+        so this step's hook sees the stream as the steps before it left it."""
+        scanner: Final = (
+            callback
+            if PipelineExecutor.supports_unified_execution(callback)
+            else _LegacyHookStreamAdapter(callback, endpoint_translation, user_api_key_dict)
+        )
+        observer: Final = _StreamRewriteObserver(scanner)
+        deliver_rewrites: Final = type(endpoint_translation).delivers_ended_stream_rewrites
         originals: Final = copy.deepcopy(streaming_chunks)
+        hook_input.pop("response", None)  # rebind-ok: an earlier step's stored response goes so this step's is stored
         try:
             if deliver_rewrites:
                 await endpoint_translation.process_output_streaming_response(
@@ -324,9 +435,12 @@ class PipelineExecutor:
                 )
         except UndeliverableStreamRewrite:
             _release_original_chunks(step.guardrail, streaming_chunks, originals)
-        else:
-            if observer.rewrote_tool_calls or (observer.rewrote_texts and not deliver_rewrites):
-                _release_original_chunks(step.guardrail, streaming_chunks, originals)
+            return
+        if observer.changed_tool_call_count or (
+            not deliver_rewrites and (observer.rewrote_texts or observer.rewrote_tool_calls)
+        ):
+            _release_original_chunks(step.guardrail, streaming_chunks, originals)
+            return
         if not callback.records_own_guardrail_information:
             add_guardrail_to_applied_guardrails_header(request_data=hook_input, guardrail_name=step.guardrail)
 
@@ -386,11 +500,11 @@ class PipelineExecutor:
                     if isinstance(response, dict):
                         callback.mark_pre_call_hook_ran(response)
             elif mode == "post_call" and streaming_chunks is not None:
-                if not use_unified or endpoint_translation is None:
+                if endpoint_translation is None:
                     return (
                         "error",
                         None,
-                        f"Guardrail '{step.guardrail}' does not support streaming pipeline execution",
+                        f"Guardrail '{step.guardrail}' cannot run on a stream without an endpoint translation",
                         None,
                     )
                 await PipelineExecutor._run_streaming_step(
@@ -446,10 +560,22 @@ class PipelineExecutor:
 
     @staticmethod
     def supports_unified_execution(callback: CustomGuardrail) -> bool:
-        """Whether this guardrail runs through the unified apply_guardrail path,
-        the interface streaming pipeline execution requires."""
+        """Whether this guardrail runs through the unified apply_guardrail path."""
         return "apply_guardrail" in type(callback).__dict__ and not callback.use_native_lifecycle_hooks
 
+    @staticmethod
+    def supports_streaming_execution(callback: CustomGuardrail) -> bool:
+        """Whether a streaming pipeline step can run this guardrail against the buffered
+        stream: through the unified path, or through its post-call hook on the assembled
+        response when that hook is its only streaming path. A guardrail with its own
+        streaming iterator hook, or with neither hook, keeps running on its own."""
+        callback_type: Final = type(callback)
+        return PipelineExecutor.supports_unified_execution(callback) or (
+            callback_type.async_post_call_success_hook is not CustomLogger.async_post_call_success_hook
+            and callback_type.async_post_call_streaming_iterator_hook
+            is CustomLogger.async_post_call_streaming_iterator_hook
+        )
+
     @staticmethod
     def find_guardrail_callback(guardrail_name: str) -> CustomGuardrail | None:
         """Look up an initialized guardrail callback by name from litellm.callbacks."""
diff --git a/litellm/proxy/policy_engine/response_retrieval.py b/litellm/proxy/policy_engine/response_retrieval.py
new file mode 100644
index 00000000000..d284c44397e
--- /dev/null
+++ b/litellm/proxy/policy_engine/response_retrieval.py
@@ -0,0 +1,152 @@
+from collections.abc import Mapping
+from dataclasses import dataclass
+from types import MappingProxyType
+from typing import TYPE_CHECKING, Final, Literal, TypeAlias
+
+from pydantic import TypeAdapter
+
+from litellm._logging import verbose_proxy_logger
+from litellm.litellm_core_utils.core_helpers import get_or_create_metadata_bucket
+from litellm.proxy.common_utils.callback_utils import (
+    add_guardrail_to_applied_guardrails_header,
+    add_policy_sources_to_metadata,
+    add_policy_to_applied_policies_header,
+)
+from litellm.proxy.common_utils.http_parsing_utils import get_tags_from_request_body
+from litellm.proxy.policy_engine.attachment_registry import get_attachment_registry
+from litellm.proxy.policy_engine.policy_matcher import PolicyMatcher
+from litellm.proxy.policy_engine.policy_registry import get_policy_registry
+from litellm.proxy.policy_engine.policy_resolver import PolicyResolver
+from litellm.responses.utils import ResponsesAPIRequestUtils
+from litellm.router_utils.common_utils import resolve_model_group_alias
+from litellm.types.proxy.policy_engine import PolicyMatchContext
+from litellm.types.proxy.policy_engine.pipeline_types import GuardrailPipeline
+
+if TYPE_CHECKING:
+    from litellm.proxy._types import UserAPIKeyAuth
+    from litellm.router import Router
+
+PolicyPipelines: TypeAlias = tuple[tuple[str, GuardrailPipeline], ...]
+
+_POLICY_PIPELINES_ADAPTER: Final = TypeAdapter(PolicyPipelines)
+
+
+@dataclass(frozen=True, slots=True)
+class UngovernedRetrieval:
+    reason: Literal["no router", "response id names no deployment", "deployment no longer in the router"]
+
+
+def _model_group_for_response_id(response_id: object, llm_router: "Router | None") -> str | UngovernedRetrieval:
+    if llm_router is None:
+        return UngovernedRetrieval("no router")
+    model_id: Final = (
+        ResponsesAPIRequestUtils.get_model_id_from_response_id(response_id) if isinstance(response_id, str) else None
+    )
+    if model_id is None:
+        return UngovernedRetrieval("response id names no deployment")
+    deployment: Final = llm_router.get_deployment(model_id)
+    if deployment is None:
+        return UngovernedRetrieval("deployment no longer in the router")
+    hidden_by: Final = _submit_model_hidden_by(deployment.model_name, llm_router.model_group_alias)
+    if hidden_by is not None:
+        verbose_proxy_logger.warning(
+            "Policy engine: background response %s re-matches policies on retrieval as model group %s (%s), "
+            "so a policy attached to the model name it was submitted as does not run on it",
+            response_id,
+            deployment.model_name,
+            hidden_by,
+        )
+    return deployment.model_name
+
+
+def _submit_model_hidden_by(model_group: str, model_group_alias: Mapping[str, object]) -> str | None:
+    if "*" in model_group:
+        return "a wildcard deployment"
+    aliases: Final = tuple(
+        alias for alias in model_group_alias if resolve_model_group_alias(model_group_alias, alias) == model_group
+    )
+    if not aliases:
+        return None
+    return f"the target of model_group_alias {', '.join(aliases)}"
+
+
+def _retrieval_context(
+    data: Mapping[str, object], user_api_key_dict: "UserAPIKeyAuth", model_group: str
+) -> PolicyMatchContext:
+    team_alias: Final = user_api_key_dict.team_alias
+    key_alias: Final = user_api_key_dict.key_alias
+    return PolicyMatchContext(
+        team_alias=team_alias if isinstance(team_alias, str) else None,
+        key_alias=key_alias if isinstance(key_alias, str) else None,
+        model=model_group,
+        tags=get_tags_from_request_body(data) or None,
+    )
+
+
+def _post_call_pipelines_for_context(context: PolicyMatchContext) -> tuple[PolicyPipelines, Mapping[str, str]]:
+    matches: Final = get_attachment_registry().get_attached_policies_with_reasons(context)
+    if not matches:
+        return (), MappingProxyType({})
+    applied_policy_names: Final = PolicyMatcher.get_policies_with_matching_conditions(
+        policy_names=[match["policy_name"] for match in matches],  # mutable-ok: the matcher takes a list
+        context=context,
+    )
+    post_call_pipelines: Final = tuple(
+        (policy_name, pipeline)
+        for policy_name, pipeline in PolicyResolver.resolve_pipelines_for_context(
+            context=context, policy_names=applied_policy_names
+        )
+        if pipeline.mode == "post_call"
+    )
+    return post_call_pipelines, MappingProxyType({match["policy_name"]: match["matched_via"] for match in matches})
+
+
+def attach_post_call_pipelines_to_retrieval(
+    data: dict[str, object],  # mutable-ok: request-state dict the policy engine hooks all write in place
+    user_api_key_dict: "UserAPIKeyAuth",
+    llm_router: "Router | None",
+) -> None:
+    if not get_policy_registry().is_initialized():
+        return
+    model_group: Final = _model_group_for_response_id(data.get("response_id"), llm_router)
+    if isinstance(model_group, UngovernedRetrieval):
+        verbose_proxy_logger.warning(
+            "Policy engine: background response %s is retrieved without its post_call policy pipelines (%s)",
+            data.get("response_id"),
+            model_group.reason,
+        )
+        return
+    context: Final = _retrieval_context(data, user_api_key_dict, model_group)
+    post_call_pipelines, policy_sources = _post_call_pipelines_for_context(context)
+    _, bucket = get_or_create_metadata_bucket(data)
+    already_attached: Final = _POLICY_PIPELINES_ADAPTER.validate_python(bucket.get("_guardrail_pipelines") or ())
+    attached_policy_names: Final = frozenset(policy_name for policy_name, _pipeline in already_attached)
+    added: Final = tuple(
+        (policy_name, pipeline)
+        for policy_name, pipeline in post_call_pipelines
+        if policy_name not in attached_policy_names
+    )
+    if not added:
+        return
+    pipelines: Final = (*already_attached, *added)
+    bucket["_guardrail_pipelines"] = pipelines
+    bucket["_pipeline_managed_guardrails"] = frozenset(
+        step.guardrail for _policy_name, pipeline in pipelines for step in pipeline.steps
+    )
+    for policy_name, _pipeline in added:
+        add_policy_to_applied_policies_header(request_data=data, policy_name=policy_name)
+    for _policy_name, pipeline in added:
+        for step in pipeline.steps:
+            add_guardrail_to_applied_guardrails_header(request_data=data, guardrail_name=step.guardrail)
+    add_policy_sources_to_metadata(
+        request_data=data,
+        policy_sources={  # mutable-ok: add_policy_sources_to_metadata takes a dict
+            policy_name: policy_sources[policy_name] for policy_name, _pipeline in added
+        },
+    )
+    verbose_proxy_logger.debug(
+        "Policy engine: attached post_call pipelines to the retrieval of background response %s (model group %s): %s",
+        data.get("response_id"),
+        model_group,
+        ", ".join(policy_name for policy_name, _pipeline in added),
+    )
diff --git a/litellm/proxy/proxy_cli.py b/litellm/proxy/proxy_cli.py
index e245367b1b4..c2d60cd5488 100644
--- a/litellm/proxy/proxy_cli.py
+++ b/litellm/proxy/proxy_cli.py
@@ -18,6 +18,12 @@ from pydantic import BaseModel, ConfigDict
 
 import litellm
 from litellm.constants import DEFAULT_NUM_WORKERS_LITELLM_PROXY
+from litellm.proxy.db.pgbouncer import (
+    PgBouncerError,
+    PgBouncerSettings,
+    export_pooled_database_url,
+    start_in_container_pgbouncer,
+)
 from litellm.proxy.db.query_engine_reaper import start_query_engine_reaper
 
 if TYPE_CHECKING:
@@ -1108,6 +1114,7 @@ def run_server(
         from litellm.proxy.db.token_auth import (
             AZURE_POSTGRESQL_AUTH_ENV_VAR,
             IAM_TOKEN_DB_AUTH_ENV_VAR,
+            resolve_database_token_auth,
             token_auth_flag_enabled,
         )
 
@@ -1377,6 +1384,21 @@ def run_server(
                 print(
                     f"Unable to connect to DB. DATABASE_URL found in environment, but prisma package not found."  # noqa: F541
                 )
+        pgbouncer_settings: Final = PgBouncerSettings()
+        upstream_database_url: Final = os.getenv("DATABASE_URL")
+        if pgbouncer_settings.enabled and upstream_database_url is not None:
+            pooled_database_url: Final = start_in_container_pgbouncer(
+                pgbouncer_settings, upstream_database_url, token_auth=resolve_database_token_auth()
+            )
+            if isinstance(pooled_database_url, PgBouncerError):
+                print(
+                    f"\033[1;31mLiteLLM Proxy: LITELLM_PGBOUNCER_ENABLED is set but the in-container pgbouncer "
+                    f"could not start: {pooled_database_url.reason}\033[0m",
+                    file=sys.stderr,
+                    flush=True,
+                )
+                sys.exit(1)
+            export_pooled_database_url(pooled_database_url)
         if port == 4000 and ProxyInitializationHelpers._is_port_in_use(port):
             port = random.randint(1024, 49152)
         if prometheus_metrics_port == port:
diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index 7219b373dc3..94e74b20297 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -16,7 +16,17 @@ import threading
 import time
 import traceback
 import warnings
-from collections.abc import AsyncGenerator, AsyncIterator, Callable, Collection, Mapping, MutableMapping, Sequence
+from collections.abc import (
+    AsyncGenerator,
+    AsyncIterator,
+    Awaitable,
+    Callable,
+    Collection,
+    Mapping,
+    MutableMapping,
+    Sequence,
+)
+from dataclasses import dataclass
 from datetime import datetime, timedelta, timezone
 from types import MappingProxyType, UnionType
 from typing import (
@@ -50,6 +60,7 @@ from litellm.constants import (
     AIOHTTP_NEEDS_CLEANUP_CLOSED,
     AIOHTTP_TTL_DNS_CACHE,
     AUDIO_SPEECH_CHUNK_SIZE,
+    BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME,
     BASE_MCP_ROUTE,
     DAILY_TAG_SPEND_BATCH_MULTIPLIER,
     DEFAULT_MAX_RECURSE_DEPTH,
@@ -62,11 +73,13 @@ from litellm.constants import (
     LITELLM_UI_SESSION_DURATION,
     RUNTIME_UPDATABLE_ROUTER_SETTINGS,
 )
+from litellm.litellm_core_utils.asyncify import asyncify
 from litellm.litellm_core_utils.litellm_logging import (
     _init_custom_logger_compatible_class,
 )
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
 from litellm.litellm_core_utils.safe_json_loads import safe_json_loads
+from litellm.litellm_core_utils.token_counter import offload_token_count
 from litellm.proxy._types import (
     UI_TEAM_ID,
     CallbackDelete,
@@ -131,6 +144,7 @@ from litellm.router_utils.auto_router_tuning_baseline import (
     snapshot_tuning_baselines,
     tuning_limit_violation,
 )
+from litellm.types.caching import RedisPipelineIncrementOperation
 from litellm.types.utils import (
     ModelResponse,
     ModelResponseStream,
@@ -138,11 +152,7 @@ from litellm.types.utils import (
     TextCompletionResponse,
     TokenCountResponse,
 )
-from litellm.utils import (
-    _invalidate_model_cost_lowercase_map,
-    load_credentials_from_list,
-    reapply_runtime_model_cost_registrations,
-)
+from litellm.utils import load_credentials_from_list
 
 if TYPE_CHECKING:
     from aiohttp import ClientSession
@@ -151,6 +161,7 @@ if TYPE_CHECKING:
     from prisma import models as prisma_models
 
     from litellm.integrations.opentelemetry import OpenTelemetry
+    from litellm.proxy.health_check_utils.shared_health_check_manager import SharedHealthCheckManager
 
     Span = _Span | Any
 else:
@@ -233,13 +244,14 @@ def generate_feedback_box():
 import contextlib
 from collections import defaultdict
 from contextlib import asynccontextmanager
-from functools import lru_cache
+from functools import lru_cache, partial
 
 import litellm
 import litellm._redis
 from litellm import Router
 from litellm._logging import _redact_string, verbose_proxy_logger, verbose_router_logger
 from litellm.caching.caching import DualCache, RedisCache
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 from litellm.caching.redis_cluster_cache import RedisClusterCache
 from litellm.constants import (
     _REALTIME_BODY_CACHE_SIZE,
@@ -268,13 +280,12 @@ from litellm.constants import (
     WEEKLY_SPEND_REPORT_JOB_ID,
 )
 from litellm.exceptions import RejectedRequestError
-from litellm.integrations.custom_guardrail import ModifyResponseException
+from litellm.integrations.custom_guardrail import CustomGuardrail, ModifyResponseException
 from litellm.integrations.custom_logger import CustomLogger
 from litellm.integrations.SlackAlerting.slack_alerting import SlackAlerting
 from litellm.litellm_core_utils.agentic_loop_settings import (
     validated_max_agentic_loops,
 )
-from litellm.litellm_core_utils.asyncify import asyncify
 from litellm.litellm_core_utils.audio_utils.utils import resolve_speech_media_type
 from litellm.litellm_core_utils.core_helpers import (
     _get_parent_otel_span_from_kwargs,
@@ -367,8 +378,11 @@ from litellm.proxy.common_utils.load_config_utils import (
 )
 from litellm.proxy.common_utils.model_deprecation import collect_model_deprecations
 from litellm.proxy.common_utils.model_listing_utils import (
+    ClaudeCodeRoutingNames,
     TeamModelNameTranslator,
+    claude_code_view_ids,
     configured_display_names,
+    is_claude_code_client,
 )
 from litellm.proxy.common_utils.openai_endpoint_utils import (
     remove_sensitive_info_from_deployment,
@@ -413,6 +427,7 @@ from litellm.proxy.config_resolvers.alerting import (
 )
 from litellm.proxy.container_endpoints.endpoints import router as container_router
 from litellm.proxy.credential_endpoints.endpoints import router as credential_router
+from litellm.proxy.db.db_transaction_queue.pod_lock_manager import PodLockManager
 from litellm.proxy.db.db_transaction_queue.spend_log_cleanup import (
     SPEND_LOG_CLEANUP_BOUND_SETTINGS,
     SpendLogCleanup,
@@ -426,6 +441,7 @@ from litellm.proxy.db.exception_handler import (
 )
 from litellm.proxy.db.gateway_request_tracking import (
     GatewayRequestAccumulator,
+    GatewayRequestRedisBuffer,
     flush_gateway_requests,
 )
 from litellm.proxy.db.proxy_worker_heartbeat import (
@@ -454,7 +470,7 @@ from litellm.proxy.hooks.model_max_budget_limiter import (
 from litellm.proxy.hooks.prompt_injection_detection import (
     _OPTIONAL_PromptInjectionDetection,
 )
-from litellm.proxy.hooks.proxy_track_cost_callback import _ProxyDBLogger
+from litellm.proxy.hooks.proxy_track_cost_callback import _ProxyDBLogger, run_spend_event
 from litellm.proxy.image_endpoints.endpoints import router as image_router
 from litellm.proxy.list_api.common import (
     PROBLEM_TYPE_BASE,
@@ -577,6 +593,11 @@ from litellm.proxy.plugin_routes import (
 from litellm.proxy.plugin_routes import (
     router as plugin_router,
 )
+from litellm.proxy.spend_tracking.spend_event_producer import (
+    CollectorSettings,
+    SpendEventProducer,
+    build_spend_event_producer,
+)
 from litellm.types.proxy.management_endpoints.management_v1 import ProblemDetail
 
 try:
@@ -928,6 +949,17 @@ def cleanup_router_config_variables():
     heuristic_v1_tuning_baselines = None
 
 
+async def flush_spend_counters_on_shutdown() -> None:
+    if prisma_client is None:
+        return
+    try:
+        await proxy_logging_obj.db_spend_update_writer.db_update_spend_transaction_handler(
+            prisma_client=prisma_client, n_retry_times=3, proxy_logging_obj=proxy_logging_obj
+        )
+    except Exception as e:  # noqa: BLE001  # shutdown must continue even if the commit fails
+        verbose_proxy_logger.exception("Error flushing spend counters on shutdown: %s", e)
+
+
 async def _flush_spend_logs_queue_on_shutdown() -> None:
     if prisma_client is None:
         return
@@ -1363,6 +1395,10 @@ async def proxy_startup_event(app: FastAPI) -> AsyncGenerator[None, None]:
         except Exception as e:
             verbose_proxy_logger.error("Error stopping DB health watchdog task: %s", e)
 
+    await _drain_spend_event_producer_on_shutdown()
+
+    await flush_spend_counters_on_shutdown()
+
     await _flush_spend_logs_queue_on_shutdown()
 
     await proxy_config.stop_config_sync_subscriber()
@@ -2357,6 +2393,17 @@ open_telemetry_logger: OpenTelemetry | None = None
 gateway_request_accumulator: Final = GatewayRequestAccumulator()
 ### INITIALIZE GLOBAL LOGGING OBJECT ###
 proxy_logging_obj: ProxyLogging = ProxyLogging(user_api_key_cache=user_api_key_cache, premium_user=premium_user)
+
+
+def _gateway_request_redis_buffer() -> GatewayRequestRedisBuffer | None:
+    """Shares the spend writer's transaction-buffer Redis and pod lock when use_redis_transaction_buffer is on."""
+    writer: Final = proxy_logging_obj.db_spend_update_writer
+    redis_cache: Final = writer.redis_update_buffer.redis_cache
+    if redis_cache is None or not writer.redis_update_buffer._should_commit_spend_updates_to_redis():
+        return None
+    return GatewayRequestRedisBuffer(redis_cache=redis_cache, pod_lock_manager=writer.pod_lock_manager)
+
+
 ### REDIS QUEUE ###
 async_result: Final = None
 celery_app_conn: Final = None
@@ -2431,16 +2478,27 @@ def load_from_azure_key_vault(use_azure_key_vault: bool = False):
         )
 
 
+spend_event_producer: SpendEventProducer | None = None
+
+
 def cost_tracking():
-    global prisma_client
+    global prisma_client, spend_event_producer
     if prisma_client is not None:
         from litellm.integrations.shadow_eval_logger import ShadowEvalLogger
 
-        litellm.logging_callback_manager.add_litellm_callback(_ProxyDBLogger())
-        litellm.logging_callback_manager.add_litellm_async_success_callback(_ProxyDBLogger())
+        spend_event_producer = build_spend_event_producer(CollectorSettings(), fallback=run_spend_event)
+        litellm.logging_callback_manager.add_litellm_callback(_ProxyDBLogger(spend_event_producer))
+        litellm.logging_callback_manager.add_litellm_async_success_callback(_ProxyDBLogger(spend_event_producer))
         litellm.logging_callback_manager.add_litellm_callback(ShadowEvalLogger())
 
 
+async def _drain_spend_event_producer_on_shutdown() -> None:
+    if spend_event_producer is None:
+        return
+    await spend_event_producer.close(drain_timeout=CollectorSettings().drain_timeout_seconds)
+    verbose_proxy_logger.info("collector: producer drained on shutdown. stats=%s", spend_event_producer.stats())
+
+
 # Bounds authoritative DB re-reads when enforcing a budget against a
 # stale-low spend counter: at most one DB read per counter per window.
 SPEND_DB_FLOOR_CACHE_TTL_SECONDS: Final = 5
@@ -2707,6 +2765,12 @@ async def _read_spend_counter_estimate(counter_key: str, fallback_spend: float)
     return fallback_spend, False
 
 
+@dataclass(frozen=True, slots=True)
+class _PendingSpendIncrement:
+    counter_key: str
+    increment: float
+
+
 async def increment_spend_counters(
     token: str | None,
     team_id: str | None,
@@ -2741,7 +2805,7 @@ async def increment_spend_counters(
 
     cost: Final[float] = response_cost
 
-    async def _key_scope(key_token: str) -> None:
+    async def _key_scope(key_token: str) -> tuple[_PendingSpendIncrement | BaseException, ...]:
         # key_token arrives pre-hashed from metadata["user_api_key"] (auth flow
         # hashes raw "sk-..." keys before they reach the callback). The
         # startswith("sk-") check is a safety net matching update_cache —
@@ -2752,30 +2816,29 @@ async def increment_spend_counters(
             hash_token(token=key_token) if isinstance(key_token, str) and key_token.startswith("sk-") else key_token
         )
         key_counter_key: Final = f"spend:key:{hashed_token}"
-        if key_counter_key not in reserved_counter_keys:
-            await _init_and_increment_spend_counter(
-                counter_key=key_counter_key,
-                source_cache_key=hashed_token,
-                increment=cost,
+        key_pending: Final[tuple[_PendingSpendIncrement, ...]] = (
+            ()
+            if key_counter_key in reserved_counter_keys
+            else (
+                await _prepare_spend_counter_increment(
+                    counter_key=key_counter_key,
+                    source_cache_key=hashed_token,
+                    increment=cost,
+                ),
             )
-
-        key_obj: Final[object] = await user_api_key_cache.async_get_cache(key=hashed_token)
-        if key_obj is None:
-            return
-        key_budget_limits = getattr(key_obj, "budget_limits", None) or (
-            key_obj.get("budget_limits") if isinstance(key_obj, dict) else None
         )
-        if isinstance(key_budget_limits, str):
-            key_budget_limits = json.loads(key_budget_limits)
-        if not isinstance(key_budget_limits, list):
-            return
-        for window in key_budget_limits:
-            duration = window["budget_duration"] if isinstance(window, dict) else window.budget_duration
-            key_window_reset_at = window.get("reset_at") if isinstance(window, dict) else window.reset_at
-            key_window_counter = f"spend:key:{hashed_token}:window:{duration}"
+
+        async def _key_window_increment(window: object) -> _PendingSpendIncrement | None:
+            duration = (
+                window["budget_duration"] if isinstance(window, dict) else getattr(window, "budget_duration", None)
+            )
+            key_window_reset_at = (
+                window.get("reset_at") if isinstance(window, dict) else getattr(window, "reset_at", None)
+            )
+            key_window_counter: Final = f"spend:key:{hashed_token}:window:{duration}"
             key_window_start = get_budget_window_start(window)
-            if key_window_counter not in reserved_counter_keys:
-                await _init_and_increment_window_spend_counter(
+            pending_window: Final = (
+                await _prepare_window_spend_counter_increment(
                     counter_key=key_window_counter,
                     entity_type="Key",
                     entity_id=hashed_token,
@@ -2783,6 +2846,9 @@ async def increment_spend_counters(
                     window_start=key_window_start,
                     increment=cost,
                 )
+                if key_window_counter not in reserved_counter_keys
+                else None
+            )
             await _enqueue_window_spend_row_update(
                 entity_type=Litellm_EntityType.KEY,
                 entity_id=hashed_token,
@@ -2792,33 +2858,48 @@ async def increment_spend_counters(
                 increment=cost,
                 request_started_at=request_started_at,
             )
+            return pending_window
 
-    async def _team_scope(scope_team_id: str) -> None:
-        team_counter_key: Final = f"spend:team:{scope_team_id}"
-        if team_counter_key not in reserved_counter_keys:
-            await _init_and_increment_spend_counter(
-                counter_key=team_counter_key,
-                source_cache_key=f"team_id:{scope_team_id}",
-                increment=cost,
-            )
-
-        team_obj: Final[object] = await user_api_key_cache.async_get_cache(key=f"team_id:{scope_team_id}")
-        if team_obj is None:
-            return
-        team_budget_limits = getattr(team_obj, "budget_limits", None) or (
-            team_obj.get("budget_limits") if isinstance(team_obj, dict) else None
+        key_obj: Final[object] = await user_api_key_cache.async_get_cache(key=hashed_token)
+        if key_obj is None:
+            return key_pending
+        key_budget_limits = getattr(key_obj, "budget_limits", None) or (
+            key_obj.get("budget_limits") if isinstance(key_obj, dict) else None
         )
-        if isinstance(team_budget_limits, str):
-            team_budget_limits = json.loads(team_budget_limits)
-        if not isinstance(team_budget_limits, list):
-            return
-        for window in team_budget_limits:
-            duration = window["budget_duration"] if isinstance(window, dict) else window.budget_duration
-            team_window_reset_at = window.get("reset_at") if isinstance(window, dict) else window.reset_at
-            team_window_counter = f"spend:team:{scope_team_id}:window:{duration}"
+        if isinstance(key_budget_limits, str):
+            key_budget_limits = json.loads(key_budget_limits)
+        if not isinstance(key_budget_limits, list):
+            return key_pending
+        window_pending: Final = await asyncio.gather(
+            *(_key_window_increment(window) for window in key_budget_limits), return_exceptions=True
+        )
+        return key_pending + tuple(item for item in window_pending if item is not None)
+
+    async def _team_scope(scope_team_id: str) -> tuple[_PendingSpendIncrement | BaseException, ...]:
+        team_counter_key: Final = f"spend:team:{scope_team_id}"
+        team_pending: Final[tuple[_PendingSpendIncrement, ...]] = (
+            ()
+            if team_counter_key in reserved_counter_keys
+            else (
+                await _prepare_spend_counter_increment(
+                    counter_key=team_counter_key,
+                    source_cache_key=f"team_id:{scope_team_id}",
+                    increment=cost,
+                ),
+            )
+        )
+
+        async def _team_window_increment(window: object) -> _PendingSpendIncrement | None:
+            duration = (
+                window["budget_duration"] if isinstance(window, dict) else getattr(window, "budget_duration", None)
+            )
+            team_window_reset_at = (
+                window.get("reset_at") if isinstance(window, dict) else getattr(window, "reset_at", None)
+            )
+            team_window_counter: Final = f"spend:team:{scope_team_id}:window:{duration}"
             team_window_start = get_budget_window_start(window)
-            if team_window_counter not in reserved_counter_keys:
-                await _init_and_increment_window_spend_counter(
+            pending_window: Final = (
+                await _prepare_window_spend_counter_increment(
                     counter_key=team_window_counter,
                     entity_type="Team",
                     entity_id=scope_team_id,
@@ -2826,6 +2907,9 @@ async def increment_spend_counters(
                     window_start=team_window_start,
                     increment=cost,
                 )
+                if team_window_counter not in reserved_counter_keys
+                else None
+            )
             await _enqueue_window_spend_row_update(
                 entity_type=Litellm_EntityType.TEAM,
                 entity_id=scope_team_id,
@@ -2835,25 +2919,47 @@ async def increment_spend_counters(
                 increment=cost,
                 request_started_at=request_started_at,
             )
+            return pending_window
 
-    async def _team_member_scope(scope_user_id: str, scope_team_id: str) -> None:
+        team_obj: Final[object] = await user_api_key_cache.async_get_cache(key=f"team_id:{scope_team_id}")
+        if team_obj is None:
+            return team_pending
+        team_budget_limits = getattr(team_obj, "budget_limits", None) or (
+            team_obj.get("budget_limits") if isinstance(team_obj, dict) else None
+        )
+        if isinstance(team_budget_limits, str):
+            team_budget_limits = json.loads(team_budget_limits)
+        if not isinstance(team_budget_limits, list):
+            return team_pending
+        window_pending: Final = await asyncio.gather(
+            *(_team_window_increment(window) for window in team_budget_limits), return_exceptions=True
+        )
+        return team_pending + tuple(item for item in window_pending if item is not None)
+
+    async def _team_member_scope(
+        scope_user_id: str, scope_team_id: str
+    ) -> tuple[_PendingSpendIncrement | BaseException, ...]:
         team_member_counter_key: Final = f"spend:team_member:{scope_user_id}:{scope_team_id}"
         if team_member_counter_key in reserved_counter_keys:
-            return
-        await _init_and_increment_spend_counter(
-            counter_key=team_member_counter_key,
-            source_cache_key=f"team_membership:{scope_user_id}:{scope_team_id}",
-            increment=cost,
+            return ()
+        return (
+            await _prepare_spend_counter_increment(
+                counter_key=team_member_counter_key,
+                source_cache_key=f"team_membership:{scope_user_id}:{scope_team_id}",
+                increment=cost,
+            ),
         )
 
-    async def _user_scope(scope_user_id: str) -> None:
+    async def _user_scope(scope_user_id: str) -> tuple[_PendingSpendIncrement | BaseException, ...]:
         user_counter_key: Final = f"spend:user:{scope_user_id}"
         if user_counter_key in reserved_counter_keys:
-            return
-        await _init_and_increment_spend_counter(
-            counter_key=user_counter_key,
-            source_cache_key=scope_user_id,
-            increment=cost,
+            return ()
+        return (
+            await _prepare_spend_counter_increment(
+                counter_key=user_counter_key,
+                source_cache_key=scope_user_id,
+                increment=cost,
+            ),
         )
 
     scope_coros: Final = tuple(
@@ -2863,7 +2969,7 @@ async def increment_spend_counters(
             _team_scope(team_id) if team_id is not None else None,
             _team_member_scope(user_id, team_id) if user_id is not None and team_id is not None else None,
             _user_scope(user_id) if user_id is not None else None,
-            _increment_end_user_and_tag_spend_counters(
+            _prepare_end_user_and_tag_spend_increments(
                 end_user_id=end_user_id,
                 tags=tags,
                 response_cost=cost,
@@ -2871,14 +2977,14 @@ async def increment_spend_counters(
             )
             if end_user_id is not None or tags is not None
             else None,
-            _increment_model_access_group_spend_counters(
+            _prepare_model_access_group_spend_increments(
                 model_access_groups=model_access_groups,
                 response_cost=cost,
                 reserved_counter_keys=reserved_counter_keys,
             )
             if model_access_groups
             else None,
-            _increment_org_spend_counter(
+            _prepare_org_spend_increment(
                 org_id=org_id,
                 response_cost=cost,
                 reserved_counter_keys=reserved_counter_keys,
@@ -2893,7 +2999,20 @@ async def increment_spend_counters(
     # as orphaned tasks that race the caller's reservation-counter invalidation;
     # all scopes settle, then the first error propagates as before.
     scope_results: Final = await asyncio.gather(*scope_coros, return_exceptions=True)
-    scope_errors: Final = [r for r in scope_results if isinstance(r, BaseException)]
+    scope_errors: Final = tuple(
+        item
+        for scope in scope_results
+        for item in (scope if isinstance(scope, tuple) else (scope,))
+        if isinstance(item, BaseException)
+    )
+    pending: Final = tuple(
+        item
+        for scope in scope_results
+        if not isinstance(scope, BaseException)
+        for item in scope
+        if not isinstance(item, BaseException)
+    )
+    await _apply_spend_counter_increments(pending=pending)
     if scope_errors:
         raise scope_errors[0]
 
@@ -2936,41 +3055,49 @@ async def _reconcile_budget_reservation_for_counter_update(
     return reserved_counter_keys
 
 
-async def _increment_end_user_and_tag_spend_counters(
+async def _prepare_end_user_and_tag_spend_increments(
     end_user_id: str | None,
     tags: list[str] | None,
     response_cost: float,
     reserved_counter_keys: set[str],
-) -> None:
-    if end_user_id is not None:
-        await _init_and_increment_unreserved_spend_counter(
-            counter_key=f"spend:end_user:{end_user_id}",
-            source_cache_key=end_user_cache_key(end_user_id),
-            increment=response_cost,
-            reserved_counter_keys=reserved_counter_keys,
-        )
-
-    if tags is None:
-        return
-
-    seen_tags: Final[set[str]] = set()
-    for tag_name in tags:
-        if not tag_name or not isinstance(tag_name, str) or tag_name in seen_tags:
-            continue
-        seen_tags.add(tag_name)
-        await _init_and_increment_unreserved_spend_counter(
-            counter_key=f"spend:tag:{tag_name}",
-            source_cache_key=tag_cache_key(tag_name),
-            increment=response_cost,
-            reserved_counter_keys=reserved_counter_keys,
-        )
+) -> tuple[_PendingSpendIncrement | BaseException, ...]:
+    unique_tags: Final = (
+        tuple(dict.fromkeys(tag for tag in tags if tag and isinstance(tag, str))) if tags is not None else ()
+    )
+    results: Final = await asyncio.gather(
+        *(
+            coro
+            for coro in (
+                _prepare_unreserved_spend_counter_increment(
+                    counter_key=f"spend:end_user:{end_user_id}",
+                    source_cache_key=end_user_cache_key(end_user_id),
+                    increment=response_cost,
+                    reserved_counter_keys=reserved_counter_keys,
+                )
+                if end_user_id is not None
+                else None,
+                *(
+                    _prepare_unreserved_spend_counter_increment(
+                        counter_key=f"spend:tag:{tag_name}",
+                        source_cache_key=tag_cache_key(tag_name),
+                        increment=response_cost,
+                        reserved_counter_keys=reserved_counter_keys,
+                    )
+                    for tag_name in unique_tags
+                ),
+            )
+            if coro is not None
+        ),
+        return_exceptions=True,
+    )
+    return tuple(item for item in results if item is not None)
 
 
-async def _increment_model_access_group_spend_counters(
+async def _prepare_model_access_group_spend_increments(
     model_access_groups: Sequence[object],
     response_cost: float,
     reserved_counter_keys: set[str],
-) -> None:
+) -> tuple[_PendingSpendIncrement | BaseException, ...]:
     """Charge the model access groups that authorized this request.
 
     Without this the counter auth reads is written only by the reservation path, so
@@ -2984,55 +3111,63 @@ async def _increment_model_access_group_spend_counters(
     unique_groups: Final = tuple(
         dict.fromkeys(group for group in model_access_groups if group and isinstance(group, str))
     )
-    for group in unique_groups:
-        await _init_and_increment_unreserved_spend_counter(
-            counter_key=model_access_group_spend_counter_key(group),
-            source_cache_key=model_access_group_cache_key(group),
-            increment=response_cost,
-            reserved_counter_keys=reserved_counter_keys,
-        )
+    results: Final = await asyncio.gather(
+        *(
+            _prepare_unreserved_spend_counter_increment(
+                counter_key=model_access_group_spend_counter_key(group),
+                source_cache_key=model_access_group_cache_key(group),
+                increment=response_cost,
+                reserved_counter_keys=reserved_counter_keys,
+            )
+            for group in unique_groups
+        ),
+        return_exceptions=True,
+    )
+    return tuple(item for item in results if item is not None)
 
 
-async def _increment_org_spend_counter(
+async def _prepare_org_spend_increment(
     org_id: str | None,
     response_cost: float,
     reserved_counter_keys: set[str],
-) -> None:
+) -> tuple[_PendingSpendIncrement, ...]:
     if org_id is None:
-        return
+        return ()
 
-    await _init_and_increment_unreserved_spend_counter(
+    pending: Final = await _prepare_unreserved_spend_counter_increment(
         counter_key=f"spend:org:{org_id}",
         source_cache_key=[f"org_id:{org_id}:with_budget", f"org_id:{org_id}"],
         increment=response_cost,
         reserved_counter_keys=reserved_counter_keys,
     )
+    return (pending,) if pending is not None else ()
 
 
-async def _init_and_increment_unreserved_spend_counter(
+async def _prepare_unreserved_spend_counter_increment(
     counter_key: str,
     source_cache_key: str | list[str],
     increment: float,
     reserved_counter_keys: set[str],
-) -> None:
+) -> _PendingSpendIncrement | None:
     if counter_key in reserved_counter_keys:
-        return
+        return None
 
-    await _init_and_increment_spend_counter(
+    return await _prepare_spend_counter_increment(
         counter_key=counter_key,
         source_cache_key=source_cache_key,
         increment=increment,
     )
 
 
-async def _init_and_increment_spend_counter(
+async def _prepare_spend_counter_increment(
     counter_key: str,
     source_cache_key: str | list[str],
     increment: float,
-):
+) -> _PendingSpendIncrement:
     """
     Initialize counter from the authoritative DB spend value if not yet
-    set, then atomically increment in both in-memory and Redis.
+    set, then return the pending increment for the caller to apply in one
+    pipelined Redis call.
 
     On first access per pod:
     1. Check spend_counter_cache (in-memory -> Redis via DualCache)
@@ -3044,13 +3179,13 @@ async def _init_and_increment_spend_counter(
        the counter as absent and seed it. Using increment means the worst case
        is over-counting (conservative, blocks slightly early) rather than
        under-counting (would allow overspend).
-    4. Increment atomically (both in-memory + Redis)
+    4. Increment is returned for the caller to apply via pipeline
     """
     await _ensure_spend_counter_initialized(
         counter_key=counter_key,
         source_cache_key=source_cache_key,
     )
-    await _increment_spend_counter_cache(counter_key=counter_key, increment=increment)
+    return _PendingSpendIncrement(counter_key=counter_key, increment=increment)
 
 
 async def _enqueue_window_spend_row_update(
@@ -3102,20 +3237,20 @@ async def _enqueue_window_spend_row_update(
         )
 
 
-async def _init_and_increment_window_spend_counter(
+async def _prepare_window_spend_counter_increment(
     counter_key: str,
     entity_type: str,
     entity_id: str,
     window_duration: str | None,
     window_start: datetime | None,
     increment: float,
-):
+) -> _PendingSpendIncrement | None:
     if window_start is None:
         verbose_proxy_logger.warning(
             "Skipping spend counter increment for invalid budget window %s",
             counter_key,
         )
-        return
+        return None
 
     initialized: Final = await _ensure_window_spend_counter_initialized(
         counter_key=counter_key,
@@ -3125,8 +3260,8 @@ async def _init_and_increment_window_spend_counter(
         window_start=window_start,
     )
     if initialized is False:
-        return
-    await _increment_spend_counter_cache(counter_key=counter_key, increment=increment)
+        return None
+    return _PendingSpendIncrement(counter_key=counter_key, increment=increment)
 
 
 async def _ensure_spend_counter_initialized(
@@ -3259,6 +3394,34 @@ async def _invalidate_spend_counter(counter_key: str):
             )
 
 
+async def _apply_spend_counter_increments(pending: Sequence[_PendingSpendIncrement]) -> None:
+    if not pending:
+        return
+    redis_cache: Final = spend_counter_cache.redis_cache
+    if redis_cache is None:
+        for item in pending:
+            await spend_counter_cache.async_increment_cache(
+                key=item.counter_key,
+                value=item.increment,
+                refresh_ttl=True,
+            )
+        return
+    ttl: Final = redis_cache.get_ttl()
+    increment_list: Final = [  # mutable-ok: async_increment_pipeline signature requires list[RedisPipelineIncrementOperation]
+        RedisPipelineIncrementOperation(key=item.counter_key, increment_value=item.increment, ttl=ttl)
+        for item in pending
+    ]
+    try:
+        results: Final = await redis_cache.async_increment_pipeline(increment_list=increment_list)
+    except Exception as e:
+        await asyncio.gather(*(_invalidate_spend_counter(counter_key=item.counter_key) for item in pending))
+        if isinstance(e, RedisCircuitBreakerOpenError):
+            return
+        raise
+    for item, current_value in zip(pending, results or ()):
+        spend_counter_cache.in_memory_cache.set_cache(key=item.counter_key, value=current_value)
+
+
 async def update_cache(
     token: str | None,
     user_id: str | None,
@@ -3630,13 +3793,50 @@ async def _run_direct_health_check_with_instrumentation(
     raise AssertionError("perform_health_check rejected every optional argument")
 
 
+async def _window_gated_health_check_db_save(
+    save: Callable[[], Awaitable[bool]],
+    pod_lock_manager: PodLockManager | None,
+    lock_ttl: int | None,
+) -> None:
+    """
+    Persist at most once per window fleet-wide. A completed save keeps the lock as the
+    "this window's save is done" marker, so it is deliberately never released and expires
+    with the interval. A save that reports failure or is cancelled releases the lock so
+    another pod's cycle in the same window can retry, instead of the fleet going a whole
+    window without a write.
+    """
+    if pod_lock_manager is None or pod_lock_manager.redis_cache is None:
+        await save()
+        return
+    acquired: Final = await pod_lock_manager.acquire_lock(
+        cronjob_id=BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME,
+        ttl=lock_ttl,
+        allow_reentrant=False,
+    )
+    if not acquired:
+        verbose_proxy_logger.debug("background_health_check_db_save_skipped another pod persisted this window")
+        return
+    try:
+        persisted: Final = await save()
+    except BaseException:
+        await pod_lock_manager.release_lock(cronjob_id=BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME)
+        raise
+    if not persisted:
+        verbose_proxy_logger.warning(
+            "background_health_check_db_save_incomplete released the window lock so another pod can retry"
+        )
+        await pod_lock_manager.release_lock(cronjob_id=BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME)
+
+
 def _schedule_background_health_check_db_save(
-    prisma_client,
-    shared_health_manager,
+    prisma_client: PrismaClient | None,
+    shared_health_manager: "SharedHealthCheckManager | None",
     model_list: list,
     healthy_endpoints: list,
     unhealthy_endpoints: list,
-):
+    pod_lock_manager: PodLockManager | None = None,
+    lock_ttl: int | None = None,
+) -> None:
     """Fire-and-forget: persist health check results to DB if prisma is available."""
     if prisma_client is None:
         return
@@ -3648,16 +3848,16 @@ def _schedule_background_health_check_db_save(
 
     checked_by: Final = shared_health_manager.pod_id if shared_health_manager is not None else "background_health_check"
     start_time: Final = time_module.time()
-    asyncio.create_task(
-        _save_background_health_checks_to_db(
-            prisma_client,
-            model_list,
-            healthy_endpoints,
-            unhealthy_endpoints,
-            start_time,
-            checked_by=checked_by,
-        )
+    save: Final = partial(
+        _save_background_health_checks_to_db,
+        prisma_client,
+        model_list,
+        healthy_endpoints,
+        unhealthy_endpoints,
+        start_time,
+        checked_by=checked_by,
     )
+    asyncio.create_task(_window_gated_health_check_db_save(save, pod_lock_manager, lock_ttl))
 
 
 def _get_endpoint_exception_status(endpoint: dict, exceptions: dict) -> int:
@@ -3964,6 +4164,8 @@ async def _run_background_health_check():
             _llm_model_list,
             healthy_endpoints,
             unhealthy_endpoints,
+            pod_lock_manager=proxy_logging_obj.db_spend_update_writer.pod_lock_manager,
+            lock_ttl=health_check_interval,
         )
 
         # Write health state to router cache for health-check-driven routing
@@ -4436,20 +4638,9 @@ def resolve_classifier_plugin(
 
 
 def _swap_in_model_cost_map(new_model_cost_map: dict) -> int:
-    """Adopt a freshly fetched cost map into this process's litellm state, return the model count"""
-    litellm.model_cost = new_model_cost_map
-    # Invalidate case-insensitive lookup map since model_cost was replaced
-    _invalidate_model_cost_lowercase_map()
-    # Repopulate provider model sets (e.g. litellm.anthropic_models) so that
-    # wildcard patterns like "anthropic/*" include any newly added models.
-    litellm.add_known_models(model_cost_map=new_model_cost_map)
-    # Counted before the re-apply below, which writes into this same dict, so the
-    # number reported describes the fetched price data alone.
-    fetched_model_count: Final = len(new_model_cost_map) if new_model_cost_map else 0
-    # The swap discards everything registered at runtime (deployment model_info,
-    # register_model overrides), so put it back on top of the fresh catalog.
-    reapply_runtime_model_cost_registrations()
-    return fetched_model_count
+    from litellm.litellm_core_utils.get_model_cost_map import adopt_model_cost_map
+
+    return adopt_model_cost_map(new_model_cost_map)
 
 
 def should_load_db_object(object_type: str | SupportedDBObjectType) -> bool:
@@ -4800,7 +4991,9 @@ class ProxyConfig:
         if not isinstance(raw_params, dict):
             raise ValueError("general_settings.coordination_redis must be a mapping of Redis connection params")
 
-        coordination_params: Final = CoordinationRedisParams(**_resolve_coordination_redis_env_refs(raw_params))
+        coordination_params: Final = CoordinationRedisParams.model_validate(
+            _resolve_coordination_redis_env_refs(raw_params)
+        )
         if not coordination_params.has_connection_target():
             raise ValueError(
                 "general_settings.coordination_redis needs a connection target: "
@@ -6536,6 +6729,14 @@ class ProxyConfig:
             return parsed
         return None
 
+    async def get_hierarchical_router_settings(
+        self,
+        user_api_key_dict: UserAPIKeyAuth | None,
+        prisma_client: PrismaClient | None,
+        proxy_logging_obj: ProxyLogging | None = None,
+    ) -> dict | None:
+        return await self._get_hierarchical_router_settings(user_api_key_dict, prisma_client, proxy_logging_obj)
+
     async def _get_hierarchical_router_settings(
         self,
         user_api_key_dict: Optional["UserAPIKeyAuth"],
@@ -8529,6 +8730,7 @@ _STREAM_KEEPALIVE: Final = object()
 _KEEPALIVE_MIN_SECONDS: Final = 1.0
 _KEEPALIVE_MAX_SECONDS: Final = 300.0
 _EMPTY_MAPPING: Final[Mapping[str, object]] = MappingProxyType({})
+_EMPTY_HEADERS: Final[Mapping[str, str]] = MappingProxyType({})
 
 
 async def _iter_with_keepalive(
@@ -9119,7 +9321,9 @@ class ProxyStartupEvent:
         if persisted is None:
             return None
 
-        coordination_params: Final = CoordinationRedisParams(**_resolve_coordination_redis_env_refs(persisted))
+        coordination_params: Final = CoordinationRedisParams.model_validate(
+            _resolve_coordination_redis_env_refs(persisted)
+        )
         if not coordination_params.has_connection_target():
             verbose_proxy_logger.warning(
                 "coordination_redis saved in the database names no connection target; ignoring it."
@@ -9543,7 +9747,7 @@ class ProxyStartupEvent:
             flush_gateway_requests,
             "interval",
             seconds=batch_writing_interval,
-            args=(prisma_client, gateway_request_accumulator),
+            args=(prisma_client, gateway_request_accumulator, _gateway_request_redis_buffer()),
             id="update_gateway_requests_job",
             replace_existing=True,
             misfire_grace_time=APSCHEDULER_MISFIRE_GRACE_TIME,
@@ -10366,6 +10570,24 @@ async def model_list(
     wants_anthropic_format: Final = (
         http_request is not None and http_request.headers.get("anthropic-version") is not None
     )
+    client_headers: Final[Mapping[str, str]] = http_request.headers if http_request is not None else _EMPTY_HEADERS
+    view_router_settings: Final = (
+        await proxy_config.get_hierarchical_router_settings(user_api_key_dict, prisma_client, proxy_logging_obj)
+        if wants_anthropic_format and is_claude_code_client(client_headers)
+        else None
+    )
+    view_aliases: Final = (
+        view_router_settings.get("model_group_alias") if isinstance(view_router_settings, Mapping) else None
+    )
+    routing_names: Final = ClaudeCodeRoutingNames(
+        llm_router,
+        team_id or user_api_key_dict.team_id,
+        (
+            user_api_key_dict.aliases,
+            user_api_key_dict.team_model_aliases,
+            view_aliases,
+        ),
+    )
 
     # Validate scope parameter if provided
     if scope is not None and scope != "expand":
@@ -10452,6 +10674,11 @@ async def model_list(
             return create_anthropic_model_list_response(
                 admin_listing,
                 display_names=configured_display_names(admin_entries, llm_router),
+                listed_ids=claude_code_view_ids(
+                    admin_listing,
+                    client_headers,
+                    routing_names,
+                ),
             )
 
         return dict(
@@ -10500,6 +10727,11 @@ async def model_list(
         return create_anthropic_model_list_response(
             listing,
             display_names=configured_display_names(entries, llm_router),
+            listed_ids=claude_code_view_ids(
+                listing,
+                client_headers,
+                routing_names,
+            ),
         )
 
     return dict(
@@ -12714,7 +12946,9 @@ async def token_counter(request: TokenCountRequest, call_endpoint: bool = False)
             CustomHuggingfaceTokenizer | None,
             model_info.get("custom_tokenizer", None),
         )
-    _tokenizer_used: Final = litellm.utils._select_tokenizer(model=model_to_use, custom_tokenizer=custom_tokenizer)
+    _tokenizer_used: Final = await asyncify(litellm.utils._select_tokenizer)(
+        model=model_to_use, custom_tokenizer=custom_tokenizer
+    )
 
     tokenizer_used: Final = str(_tokenizer_used["type"])
     system_message: Final = _system_message(system)
@@ -12727,7 +12961,7 @@ async def token_counter(request: TokenCountRequest, call_endpoint: bool = False)
     counted_tools: Final = cast(  # cast-ok: raw OpenAI or Anthropic tool dicts, both of which token_counter formats
         list[ChatCompletionToolParam] | None, tools if counted_messages is not None else None
     )
-    total_tokens: Final = await asyncify(litellm.token_counter)(
+    total_tokens: Final = await offload_token_count(litellm.token_counter)(
         model=model_to_use,
         text=prompt,
         messages=counted_messages,
@@ -17550,6 +17784,66 @@ async def delete_callback(
         )
 
 
+def _normalize_callback_alias(callback_name: str) -> str:
+    callback_aliases: Final = (
+        ("opentelemetry", "otel"),
+        ("s3_v2", "s3"),
+        ("aws_sqs", "sqs"),
+        ("custom_callback_api", "generic_api"),
+    )
+    return next(
+        (canonical_name for alias, canonical_name in callback_aliases if alias == callback_name),
+        callback_name,
+    )
+
+
+def _callback_module_name(callback: CustomLogger | Callable[..., object]) -> str:
+    if inspect.ismethod(callback):
+        return callback.__func__.__module__
+    if inspect.isfunction(callback):
+        return callback.__module__
+    return type(callback).__module__
+
+
+def _is_litellm_internal_callback(callback_name: str, callback: CustomLogger | Callable[..., object]) -> bool:
+    from litellm.litellm_core_utils.custom_logger_registry import CustomLoggerRegistry
+
+    module_owner: Final = _callback_module_name(callback).partition(".")[0]
+    is_registered_integration: Final = callback_name in CustomLoggerRegistry.CALLBACK_CLASS_STR_TO_CLASS_TYPE
+    return not is_registered_integration and module_owner in ("litellm", "litellm_enterprise")
+
+
+def _is_instance_of_configured_callback(
+    callback_name: str, callback: CustomLogger | Callable[..., object], configured_classes: tuple[type, ...]
+) -> bool:
+    """Self-naming OTel-family instances (`arize`, `weave_otel`) match by name, so a configured `logfire` (a bare
+    `OpenTelemetry`) does not hide YAML-configured siblings of the same class."""
+    from litellm.litellm_core_utils.custom_logger_registry import CustomLoggerRegistry
+
+    class_derived_name: Final = CustomLoggerRegistry.get_callback_str_from_class_type(type(callback))
+    return isinstance(callback, configured_classes) and callback_name in (class_derived_name, type(callback).__name__)
+
+
+def _hidden_runtime_callback_names(configured_callback_names: frozenset[str]) -> frozenset[str]:
+    from litellm.litellm_core_utils.custom_logger_registry import CustomLoggerRegistry
+
+    configured_classes: Final = tuple(
+        CustomLoggerRegistry.CALLBACK_CLASS_STR_TO_CLASS_TYPE[name]
+        for name in configured_callback_names
+        if name in CustomLoggerRegistry.CALLBACK_CLASS_STR_TO_CLASS_TYPE
+    )
+    configured_modules: Final = frozenset(name.rsplit(".", 1)[0] for name in configured_callback_names if "." in name)
+    internal_callback_names: Final = frozenset({"cache", "vector_store_pre_call_hook"})
+    return internal_callback_names | frozenset(
+        callback_name
+        for callback_name, callback in litellm.logging_callback_manager.get_callback_objects()
+        if isinstance(callback, CustomGuardrail)
+        or _is_litellm_internal_callback(callback_name, callback)
+        or _is_instance_of_configured_callback(callback_name, callback, configured_classes)
+        or _callback_module_name(callback) in configured_modules
+    )
+
+
 @router.get(
     "/get/config/callbacks",
     tags=["config.yaml"],
@@ -17582,10 +17876,10 @@ async def get_config(
         # Normalize string callbacks to lists
         def normalize_callback(callback):
             if isinstance(callback, str):
-                return [callback]
-            elif callback is None:
-                return []
-            return callback
+                return (callback,)
+            if callback is None:
+                return ()
+            return tuple(callback) if isinstance(callback, (list, dict)) else ()
 
         _success_callbacks = normalize_callback(_success_callbacks)
         _failure_callbacks = normalize_callback(_failure_callbacks)
@@ -17616,6 +17910,30 @@ async def get_config(
         for _callback in _success_and_failure_callbacks:
             _data_to_return.append(process_callback(_callback, "success_and_failure", environment_variables))
 
+        configured_callback_names: Final = frozenset(
+            _normalize_callback_alias(callback)
+            for callback in (_success_callbacks + _failure_callbacks + _success_and_failure_callbacks)
+        )
+        runtime_callbacks_by_type: Final = litellm.logging_callback_manager.get_callbacks_by_type()
+        hidden_callback_names: Final = _hidden_runtime_callback_names(configured_callback_names)
+        runtime_callback_rows: Final = tuple(
+            (_normalize_callback_alias(callback_name), callback_type)
+            for callback_type, callback_names in (
+                ("success", runtime_callbacks_by_type["success"]),
+                ("failure", runtime_callbacks_by_type["failure"]),
+                ("success_and_failure", runtime_callbacks_by_type["success_and_failure"]),
+            )
+            for callback_name in callback_names
+            if callback_name not in hidden_callback_names
+        )
+        runtime_only_rows: Final = sorted(
+            frozenset(row for row in runtime_callback_rows if row[0] not in configured_callback_names)
+        )
+        _data_to_return.extend(
+            dict(process_callback(callback_name, callback_type, environment_variables), read_only=True)
+            for callback_name, callback_type in runtime_only_rows
+        )
+
         _data_to_return = _apply_callback_role_gate(_data_to_return, is_full_admin)
 
         # Check if slack alerting is on
diff --git a/litellm/proxy/response_polling/background_streaming.py b/litellm/proxy/response_polling/background_streaming.py
index 0fd242f2bc1..fac45d4391c 100644
--- a/litellm/proxy/response_polling/background_streaming.py
+++ b/litellm/proxy/response_polling/background_streaming.py
@@ -15,6 +15,7 @@ from typing import TYPE_CHECKING, Final, TypeAlias
 
 from fastapi import Request, Response
 from fastapi.responses import StreamingResponse
+from starlette.types import Message
 from typing_extensions import ReadOnly, TypedDict
 
 from litellm._logging import verbose_proxy_logger
@@ -74,6 +75,20 @@ class _StreamEventParser:
     parse: Callable[[str], _StreamEvent] = staticmethod(json.loads)
 
 
+async def _never_receive() -> Message:
+    await asyncio.Event().wait()
+    raise AssertionError("unreachable")
+
+
+def detach_request_from_client(request: Request) -> Request:
+    """Same scope (headers, parsed body, auth) but a receive() that never yields http.disconnect.
+
+    The polling client closes its connection right after getting the polling id, so the
+    upstream call must not be cancelled by the client-disconnect guards.
+    """
+    return Request(request.scope, _never_receive)
+
+
 async def background_streaming_task(
     polling_id: str,
     data: dict[str, object],
@@ -123,7 +138,7 @@ async def background_streaming_task(
         # Pre-call checks (rate limits, guardrails, budget) were already run
         # before polling ID creation, so skip them here to avoid double-counting.
         response: Final[StreamingResponse] = await processor.base_process_llm_request(
-            request=request,
+            request=detach_request_from_client(request),
             fastapi_response=fastapi_response,
             user_api_key_dict=user_api_key_dict,
             route_type="aresponses",
diff --git a/litellm/proxy/schema.prisma b/litellm/proxy/schema.prisma
index 3d254cd2ea2..817df082d8c 100644
--- a/litellm/proxy/schema.prisma
+++ b/litellm/proxy/schema.prisma
@@ -282,6 +282,7 @@ model LiteLLM_ObjectPermissionTable {
   mcp_toolsets          String[]       @default([]) // Toolset IDs granted to this key/team/user
   search_tools          String[]       @default([]) // search_tool_name values this key/team/user may call
   mcp_tool_search_enabled Boolean?
+  skills                String[]       @default([]) // Claude Code plugin names granted to this key/team beyond the public (enabled) set
   teams                 LiteLLM_TeamTable[]
   projects              LiteLLM_ProjectTable[]
   verification_tokens   LiteLLM_VerificationToken[]
@@ -492,7 +493,7 @@ model LiteLLM_JWTKeyMapping {
     updated_at        DateTime @default(now()) @updatedAt
     updated_by        String?
 
-    litellm_verification_token LiteLLM_VerificationToken @relation(fields: [token], references: [token])
+    litellm_verification_token LiteLLM_VerificationToken @relation(fields: [token], references: [token], onDelete: Cascade)
 
     @@unique([jwt_claim_name, jwt_claim_value])
     @@index([jwt_claim_name, jwt_claim_value, is_active])
diff --git a/litellm/proxy/spend_tracking/budget_reservation.py b/litellm/proxy/spend_tracking/budget_reservation.py
index bf5eadcd85d..ef21551ca93 100644
--- a/litellm/proxy/spend_tracking/budget_reservation.py
+++ b/litellm/proxy/spend_tracking/budget_reservation.py
@@ -34,6 +34,7 @@ from litellm.proxy.common_utils.user_api_key_cache import (
 )
 from litellm.proxy.utils import PrismaClient, ProxyLogging
 from litellm.router import Router
+from litellm.rust_bridge.token_counter import count_anthropic_input_tokens, uses_anthropic_tokenizer
 from litellm.types.proxy.model_access_group_budget import ModelAccessGroupBudget
 from litellm.types.router import DeploymentTypedDict
 
@@ -210,6 +211,7 @@ async def reserve_budget_for_request(
     end_user_object: object = None,
     apply_user_budget_to_team_keys: bool = False,
     fail_closed_budget_enforcement: bool = False,
+    raw_body: bytes | None = None,
 ) -> dict | None:
     if valid_token is None or not RouteChecks.is_llm_api_route(route=route):
         return None
@@ -237,6 +239,7 @@ async def reserve_budget_for_request(
         request_body=request_body,
         route=route,
         llm_router=llm_router,
+        raw_body=raw_body,
     )
 
     current_spend_by_counter_key: Final[dict[str, float]] = {}
@@ -315,6 +318,7 @@ async def reserve_budget_for_request(
         "entries": applied_entries,
         "finalized": False,
         "input_cost": min(float(input_cost or 0.0), reservation_cost),
+        "input_tokens": max(input_token_counts.values(), default=None),
     }
 
 
@@ -1272,7 +1276,7 @@ def _get_model_cost_info(
     llm_router: Router | None,
 ) -> Mapping[str, object] | None:
     if llm_router is not None:
-        model_group_info: Final = llm_router.get_model_group_info(model_group=model)
+        model_group_info: Final = llm_router.cached_model_group_info(model)
         if model_group_info is not None:
             return model_group_info.model_dump()
     return dict(litellm.get_model_info(model=model))
@@ -1314,7 +1318,7 @@ def _deployment_tiered_pricing_table(
     backend_model: Final = _get_value(_get_value(deployment, "litellm_params"), "model")
     if not isinstance(model_id, str) or not isinstance(backend_model, str):
         return None
-    deployment_model_info: Final = llm_router.get_deployment_model_info(model_id=model_id, model_name=backend_model)
+    deployment_model_info: Final = llm_router.cached_deployment_model_info(model_id, backend_model)
     if deployment_model_info is None:
         return None
     tiered_pricing: Final = deployment_model_info.get("tiered_pricing")
@@ -1355,24 +1359,46 @@ async def count_request_input_tokens(
     request_body: dict,
     route: str,
     llm_router: Router | None,
+    raw_body: bytes | None = None,
 ) -> Mapping[str, int]:
     """Input-token count per candidate model, counted once per request.
 
     Tokenizing is the reservation path's dominant CPU cost and is O(prompt), so
     counting a large prompt inline stalls every other request on the worker.
-    Large prompts are counted in a worker thread, and the counts are reused by
-    both the max-cost and the input-cost estimate.
+    Models on the Anthropic tokenizer are counted from the raw body by the Rust
+    bridge when it is enabled, which parses and tokenizes with the GIL released.
+    Everything it declines is counted in Python, large prompts in a worker
+    thread. The counts are reused by both the max-cost and the input-cost
+    estimate.
     """
     models: Final = _get_request_models(request_body=request_body, route=route, llm_router=llm_router)
     if not models:
         return MappingProxyType({})
-    if _approximate_input_size(request_body) < TOKENIZE_OFF_EVENT_LOOP_MIN_CHARS:
-        return _count_input_tokens_for_models(request_body=request_body, models=models)
-    return await asyncio.to_thread(
-        _count_input_tokens_for_models,
-        request_body=request_body,
-        models=models,
+    rust_count: Final = (
+        await count_anthropic_input_tokens(raw_body)
+        if raw_body is not None and any(uses_anthropic_tokenizer(model) for model in models)
+        else None
     )
+    rust_counts: Final = MappingProxyType(
+        {
+            model: rust_count.input_tokens
+            for model in models
+            if rust_count is not None and uses_anthropic_tokenizer(model)
+        }
+    )
+    python_models: Final = tuple(model for model in models if model not in rust_counts)
+    if not python_models:
+        return rust_counts
+    python_counts: Final = (
+        _count_input_tokens_for_models(request_body=request_body, models=python_models)
+        if _approximate_input_size(request_body) < TOKENIZE_OFF_EVENT_LOOP_MIN_CHARS
+        else await asyncio.to_thread(
+            _count_input_tokens_for_models,
+            request_body=request_body,
+            models=python_models,
+        )
+    )
+    return MappingProxyType({**rust_counts, **python_counts})
 
 
 def _count_input_tokens_for_models(
diff --git a/litellm/proxy/spend_tracking/key_metadata_recovery.py b/litellm/proxy/spend_tracking/key_metadata_recovery.py
index 7de18521edd..29688b61b3d 100644
--- a/litellm/proxy/spend_tracking/key_metadata_recovery.py
+++ b/litellm/proxy/spend_tracking/key_metadata_recovery.py
@@ -1,5 +1,7 @@
+import asyncio
 from collections.abc import Awaitable, Callable, Mapping, Sequence
 from collections.abc import Set as AbstractSet
+from datetime import datetime, timedelta
 from types import MappingProxyType
 from typing import Final, TypeVar
 
@@ -7,6 +9,13 @@ from pydantic import BaseModel, TypeAdapter
 from typing_extensions import ReadOnly, TypedDict
 
 from litellm._logging import verbose_proxy_logger
+from litellm.caching.in_memory_cache import InMemoryCache
+from litellm.constants import (
+    SPEND_LOG_KEY_METADATA_CACHE_MAX_ITEMS,
+    SPEND_LOG_KEY_METADATA_CACHE_TTL,
+    SPEND_LOG_KEY_METADATA_MISS_CACHE_TTL,
+    SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS,
+)
 from litellm.litellm_core_utils.litellm_logging import is_valid_sha256_hash
 from litellm.proxy.utils import PrismaClient
 from litellm.repositories.user_repository import UserRepository
@@ -27,6 +36,33 @@ WHERE encode(sha256(convert_to(token, 'UTF8')), 'hex') = ANY($1::text[])
 ORDER BY token, deleted_at DESC
 """
 
+_SPEND_LOG_ALIAS_SQL: Final = """
+SELECT api_key AS digest,
+    MIN(key_alias) AS first_alias,
+    MAX(key_alias) AS last_alias,
+    MIN(team_id) AS first_team,
+    MAX(team_id) AS last_team,
+    MIN(user_id) AS first_owner,
+    MAX(user_id) AS last_owner
+FROM (
+    SELECT api_key,
+        NULLIF(metadata->>'user_api_key_alias', '') AS key_alias,
+        COALESCE(NULLIF(team_id, ''), NULLIF(metadata->>'user_api_key_team_id', '')) AS team_id,
+        COALESCE(NULLIF("user", ''), NULLIF(metadata->>'user_api_key_user_id', '')) AS user_id
+    FROM "LiteLLM_SpendLogs"
+    WHERE api_key = ANY($1::text[])
+      AND "startTime" >= $2::timestamp
+      AND "startTime" < $3::timestamp
+) named
+WHERE COALESCE(key_alias, user_id, team_id) IS NOT NULL
+GROUP BY api_key
+"""
+
+_SPEND_LOG_STATEMENT_TIMEOUT_SQL: Final = f"SET LOCAL statement_timeout = {SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS}"
+_SPEND_LOG_TRANSACTION_TIMEOUT: Final = timedelta(milliseconds=2 * SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS)
+
+_HASHED_JWT_PREFIX: Final = "hashed-jwt-"
+
 
 class KeyMetadataDict(TypedDict, total=False):
     key_alias: ReadOnly[str | None]
@@ -42,7 +78,35 @@ class _TokenDigestRow(BaseModel):
     user_id: str | None = None
 
 
+def _unanimous(first: str | None, last: str | None) -> str | None:
+    return first if first == last else None
+
+
+class _SpendLogDigestRow(BaseModel):
+    digest: str
+    first_alias: str | None = None
+    last_alias: str | None = None
+    first_team: str | None = None
+    last_team: str | None = None
+    first_owner: str | None = None
+    last_owner: str | None = None
+
+    def metadata(self) -> KeyMetadataDict:
+        return KeyMetadataDict(
+            key_alias=_unanimous(self.first_alias, self.last_alias),
+            team_id=_unanimous(self.first_team, self.last_team),
+            user_id=_unanimous(self.first_owner, self.last_owner),
+        )
+
+
 _TOKEN_DIGEST_ROWS: Final = TypeAdapter(tuple[_TokenDigestRow, ...])
+_SPEND_LOG_DIGEST_ROWS: Final = TypeAdapter(tuple[_SpendLogDigestRow, ...])
+_CACHED_KEY_METADATA: Final = TypeAdapter(KeyMetadataDict)
+_SPEND_LOG_METADATA_CACHE: Final = InMemoryCache(
+    max_size_in_memory=SPEND_LOG_KEY_METADATA_CACHE_MAX_ITEMS,
+    default_ttl=SPEND_LOG_KEY_METADATA_CACHE_TTL,
+)
+_SPEND_LOG_QUERY_LOCK: Final = asyncio.Lock()
 _EMPTY_KEY_METADATA: Final[Mapping[str, KeyMetadataDict]] = MappingProxyType({})
 _EMPTY_EMAILS: Final[Mapping[str, str]] = MappingProxyType({})
 
@@ -138,14 +202,6 @@ async def recover_double_hashed_key_metadata(
     prisma_client: PrismaClient,
     missing_keys: AbstractSet[str],
 ) -> Mapping[str, KeyMetadataDict]:
-    """
-    Recover key_alias/team_id/user_id for DailyUserSpend.api_key values that
-    were double-hashed by the v1.99 spend-log provenance gate.
-
-    Those rows store hash(VerificationToken.token) instead of the token, so the
-    exact join misses. Postgres hashes the token column itself, one pass over
-    active keys and one over deleted keys, so no key row crosses the wire.
-    """
     sha_missing: Final = frozenset(key for key in missing_keys if is_valid_sha256_hash(key))
     if not sha_missing:
         return _EMPTY_KEY_METADATA
@@ -168,6 +224,117 @@ async def recover_double_hashed_key_metadata(
     return MappingProxyType({**from_active, **from_deleted})
 
 
+def _is_spend_log_digest(key: str) -> bool:
+    return is_valid_sha256_hash(key.removeprefix(_HASHED_JWT_PREFIX))
+
+
+def _spend_log_cache_key(digest: str, window: tuple[datetime, datetime]) -> str:
+    start, end = window
+    return f"spend_log_key_metadata:{digest}:{start.isoformat()}:{end.isoformat()}"
+
+
+def _cached_spend_log_metadata(
+    cache: InMemoryCache,
+    digests: AbstractSet[str],
+    window: tuple[datetime, datetime],
+) -> Mapping[str, KeyMetadataDict]:
+    return MappingProxyType(
+        {
+            digest: _CACHED_KEY_METADATA.validate_python(cached)
+            for digest in digests
+            for cached in (cache.get_cache(_spend_log_cache_key(digest, window)),)
+            if cached is not None
+        }
+    )
+
+
+async def _spend_log_rows_within_the_statement_timeout(
+    prisma_client: PrismaClient,
+    digests: AbstractSet[str],
+    window: tuple[datetime, datetime],
+) -> Sequence[Mapping[str, object]]:
+    start, end = window
+    async with prisma_client.db.tx(timeout=_SPEND_LOG_TRANSACTION_TIMEOUT) as transaction:
+        await transaction.execute_raw(_SPEND_LOG_STATEMENT_TIMEOUT_SQL)
+        return await transaction.query_raw(_SPEND_LOG_ALIAS_SQL, sorted(digests), start, end)
+
+
+async def _query_spend_log_metadata(
+    prisma_client: PrismaClient,
+    digests: AbstractSet[str],
+    window: tuple[datetime, datetime],
+) -> Mapping[str, KeyMetadataDict] | None:
+    rows: Final = await _db_or_empty(
+        lambda: _spend_log_rows_within_the_statement_timeout(prisma_client, digests, window),
+        "Failed spend-log alias recovery for %d missing keys: %s",
+        len(digests),
+    )
+    if rows is None:
+        return None
+    return MappingProxyType(
+        {
+            row.digest: meta
+            for row in _SPEND_LOG_DIGEST_ROWS.validate_python(rows)
+            for meta in (row.metadata(),)
+            if row.digest in digests and any(meta.values())
+        }
+    )
+
+
+def _remember_spend_log_metadata(
+    cache: InMemoryCache, digest: str, window: tuple[datetime, datetime], meta: KeyMetadataDict | None
+) -> None:
+    key: Final = _spend_log_cache_key(digest, window)
+    if meta is not None:
+        cache.set_cache(key, meta)
+        return
+    missed_before: Final = f"{key}:missed-before"
+    if cache.get_cache(missed_before) is not None:
+        cache.set_cache(key, KeyMetadataDict())
+        return
+    cache.set_cache(key, KeyMetadataDict(), ttl=SPEND_LOG_KEY_METADATA_MISS_CACHE_TTL)
+    cache.set_cache(missed_before, True)
+
+
+async def _spend_log_metadata_one_query_at_a_time(
+    prisma_client: PrismaClient,
+    cache: InMemoryCache,
+    lock: asyncio.Lock,
+    digests: AbstractSet[str],
+    window: tuple[datetime, datetime],
+) -> Mapping[str, KeyMetadataDict]:
+    async with lock:
+        settled: Final = _cached_spend_log_metadata(cache, digests, window)
+        pending: Final = digests - frozenset(settled)
+        fresh: Final = (
+            await _query_spend_log_metadata(prisma_client, pending, window) if pending else _EMPTY_KEY_METADATA
+        )
+        found: Final = fresh if fresh is not None else _EMPTY_KEY_METADATA
+        for digest in pending:
+            _remember_spend_log_metadata(cache, digest, window, found.get(digest))
+        return MappingProxyType({**settled, **found})
+
+
+async def recover_key_metadata_from_spend_logs(
+    prisma_client: PrismaClient,
+    missing_keys: AbstractSet[str],
+    window: tuple[datetime, datetime],
+    cache: InMemoryCache = _SPEND_LOG_METADATA_CACHE,
+    lock: asyncio.Lock = _SPEND_LOG_QUERY_LOCK,
+) -> Mapping[str, KeyMetadataDict]:
+    digests: Final = frozenset(key for key in missing_keys if _is_spend_log_digest(key))
+    if not digests:
+        return _EMPTY_KEY_METADATA
+    cached: Final = _cached_spend_log_metadata(cache, digests, window)
+    uncached: Final = digests - frozenset(cached)
+    settled: Final = (
+        await _spend_log_metadata_one_query_at_a_time(prisma_client, cache, lock, uncached, window)
+        if uncached
+        else _EMPTY_KEY_METADATA
+    )
+    return MappingProxyType({digest: meta for digest, meta in (*cached.items(), *settled.items()) if meta})
+
+
 def _row_with_recovered_fields(
     row: Mapping[str, object],
     recovered: Mapping[str, KeyMetadataDict],
diff --git a/litellm/proxy/spend_tracking/spend_event.py b/litellm/proxy/spend_tracking/spend_event.py
new file mode 100644
index 00000000000..53f26346f85
--- /dev/null
+++ b/litellm/proxy/spend_tracking/spend_event.py
@@ -0,0 +1,418 @@
+"""Compact, typed success event handed from an inference worker to the collector.
+
+``build_spend_event`` runs on the inference worker right after ``Logging.async_success_handler``
+has built the ``standard_logging_object`` (so the cost is already known). It validates the success
+callback's ``kwargs`` into the projection ``_PROXY_track_cost_callback`` and
+``DBSpendUpdateWriter.update_database`` actually read: identities and metadata, timings, usage, the
+standard logging payload without its prompt/response bodies, and the tool names. The request
+messages, the raw ``proxy_server_request`` body and the full response travel only when spend logs
+are configured to store prompts and responses. The cache key is the preset key the caching layer
+already computed, never a fresh hash over the request body.
+
+``spend_event_callback_args`` rebuilds the ``(kwargs, response_obj, start_time, end_time)`` tuple
+the existing cost pipeline consumes, so the sidecar runs the unchanged pipeline against the event.
+"""
+
+from collections.abc import Mapping, Sequence
+from dataclasses import dataclass
+from datetime import datetime
+from types import MappingProxyType
+from typing import Final, Literal, TypeAlias
+
+from pydantic import BaseModel, ConfigDict, TypeAdapter, ValidationError
+from typing_extensions import NotRequired, ReadOnly, TypedDict
+
+import litellm
+from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy.db.spend_log_tool_index import response_tool_call_names
+from litellm.types.interactions import InteractionsAPIResponse
+from litellm.types.utils import LiteLLMBatch, Usage
+
+SPEND_EVENT_VERSION: Final = 1
+CACHE_OFF_KEY: Final = "Cache OFF"
+
+ObjectMapping: TypeAlias = Mapping[str, object]
+
+_UNSERIALIZABLE_METADATA_KEYS: Final = frozenset({"user_api_key_auth", "litellm_parent_otel_span"})
+_STANDARD_LOGGING_BODY_KEYS: Final = frozenset({"messages", "response"})
+_STANDARD_LOGGING_DROPPED_KEYS: Final = frozenset({"model_parameters"})
+_NOT_OFFLOADED_RESPONSE_TYPES: Final = (LiteLLMBatch, InteractionsAPIResponse)
+
+
+class _LitellmParams(TypedDict, total=False):
+    api_base: ReadOnly[str | None]
+    custom_llm_provider: ReadOnly[str | None]
+    litellm_call_id: ReadOnly[str | None]
+    user_api_key_end_user_id: ReadOnly[str | None]
+    metadata: ReadOnly[ObjectMapping | None]
+    litellm_metadata: ReadOnly[ObjectMapping | None]
+    proxy_server_request: ReadOnly[ObjectMapping | None]
+    preset_cache_key: ReadOnly[str | None]
+
+
+class _DynamicParams(TypedDict, total=False):
+    turn_off_message_logging: ReadOnly[bool | None]
+
+
+class _RequestBody(TypedDict, total=False):
+    tools: ReadOnly[Sequence[ObjectMapping] | None]
+
+
+class _PassthroughPayload(TypedDict, total=False):
+    request_body: ReadOnly[_RequestBody | None]
+
+
+class _ToolCallFunction(TypedDict):
+    name: ReadOnly[str]
+    arguments: ReadOnly[str]
+
+
+class _ToolCall(TypedDict):
+    id: ReadOnly[str | None]
+    type: ReadOnly[Literal["function"]]
+    function: ReadOnly[_ToolCallFunction]
+
+
+class _ToolCallMessage(TypedDict):
+    role: ReadOnly[Literal["assistant"]]
+    content: ReadOnly[None]
+    tool_calls: ReadOnly[Sequence[_ToolCall]]
+
+
+class _ToolCallChoice(TypedDict):
+    index: ReadOnly[int]
+    finish_reason: ReadOnly[Literal["tool_calls"]]
+    message: ReadOnly[_ToolCallMessage]
+
+
+class CompactResponse(TypedDict, total=False):
+    """What the spend pipeline reads off a response: its id, usage and which tools it called."""
+
+    id: ReadOnly[object]
+    model: ReadOnly[object]
+    usage: ReadOnly[object]
+    usage_info: ReadOnly[object]
+    status: ReadOnly[object]
+    background: ReadOnly[object]
+    choices: ReadOnly[Sequence[_ToolCallChoice]]
+
+
+class _SuccessKwargs(TypedDict, total=False):
+    """The success callback's ``kwargs`` (``Logging.model_call_details``), validated and projected."""
+
+    litellm_call_id: ReadOnly[str | None]
+    call_type: ReadOnly[str | None]
+    model: ReadOnly[str | None]
+    custom_llm_provider: ReadOnly[str | None]
+    stream: ReadOnly[bool | None]
+    complete_streaming_response: ReadOnly[object]
+    cache_hit: ReadOnly[bool | None]
+    response_cost: ReadOnly[float | None]
+    completion_start_time: ReadOnly[datetime | None]
+    agent_id: ReadOnly[str | None]
+    litellm_trace_id: ReadOnly[str | None]
+    litellm_params: ReadOnly[_LitellmParams]
+    standard_logging_object: ReadOnly[ObjectMapping | None]
+    standard_callback_dynamic_params: ReadOnly[_DynamicParams | None]
+    combined_usage_object: ReadOnly[Usage | None]
+    realtime_tools: ReadOnly[Sequence[object] | None]
+    realtime_tool_calls: ReadOnly[Sequence[object] | None]
+    tools: ReadOnly[Sequence[ObjectMapping] | None]
+    passthrough_logging_payload: ReadOnly[_PassthroughPayload | None]
+
+
+class _FunctionToolFunction(TypedDict):
+    name: ReadOnly[str]
+
+
+class _FunctionTool(TypedDict):
+    type: ReadOnly[Literal["function"]]
+    function: ReadOnly[_FunctionToolFunction]
+
+
+class SpendCallbackKwargs(TypedDict):
+    """The ``kwargs`` handed to ``_PROXY_track_cost_callback`` on the sidecar."""
+
+    litellm_call_id: ReadOnly[str | None]
+    call_type: ReadOnly[str | None]
+    model: ReadOnly[str | None]
+    custom_llm_provider: ReadOnly[str | None]
+    stream: ReadOnly[bool | None]
+    cache_hit: ReadOnly[bool | None]
+    response_cost: ReadOnly[float | None]
+    completion_start_time: ReadOnly[datetime | None]
+    agent_id: ReadOnly[str | None]
+    litellm_trace_id: ReadOnly[str | None]
+    litellm_params: ReadOnly[_LitellmParams]
+    standard_logging_object: ReadOnly[ObjectMapping | None]
+    standard_callback_dynamic_params: ReadOnly[_DynamicParams | None]
+    combined_usage_object: ReadOnly[Usage | None]
+    realtime_tools: ReadOnly[Sequence[object] | None]
+    realtime_tool_calls: ReadOnly[Sequence[object] | None]
+    tools: ReadOnly[Sequence[_FunctionTool] | None]
+    complete_streaming_response: NotRequired[ReadOnly[CompactResponse | None]]
+
+
+_NO_LITELLM_PARAMS: Final[_LitellmParams] = {}
+_SUCCESS_KWARGS: Final = TypeAdapter(_SuccessKwargs)
+_OBJECT_MAPPING: Final = TypeAdapter(ObjectMapping)
+_COMPACT_RESPONSE: Final = TypeAdapter(CompactResponse)
+
+
+class SpendEvent(BaseModel):
+    model_config = ConfigDict(frozen=True, extra="forbid")
+
+    version: Literal[1]
+    litellm_call_id: str | None
+    call_type: str | None
+    model: str | None
+    custom_llm_provider: str | None
+    stream: bool | None
+    complete_streaming_response: bool
+    cache_hit: bool | None
+    response_cost: float | None
+    start_time: datetime
+    end_time: datetime
+    completion_start_time: datetime | None
+    agent_id: str | None
+    litellm_trace_id: str | None
+    litellm_params: _LitellmParams
+    standard_logging_object: ObjectMapping | None
+    standard_callback_dynamic_params: _DynamicParams | None
+    response: CompactResponse | None
+    combined_usage: ObjectMapping | None
+    realtime_tools: Sequence[object] | None
+    realtime_tool_calls: Sequence[object] | None
+    request_tool_names: tuple[str, ...]
+
+
+@dataclass(frozen=True, slots=True)
+class SpendEventCallbackArgs:
+    kwargs: SpendCallbackKwargs
+    response_obj: CompactResponse | None
+    start_time: datetime
+    end_time: datetime
+
+
+@dataclass(frozen=True, slots=True)
+class SpendEventBuildError:
+    reason: str
+
+
+@dataclass(frozen=True, slots=True)
+class SpendEventDecodeError:
+    reason: str
+
+
+def is_offloadable_success(response_obj: object) -> bool:
+    """Batch retrieves and interaction polls branch on the concrete response class, so they stay in-process."""
+    return not isinstance(response_obj, _NOT_OFFLOADED_RESPONSE_TYPES)
+
+
+def _json_fallback(value: object) -> str:
+    return str(value)
+
+
+def _mapping_or_none(value: object) -> ObjectMapping | None:
+    try:
+        return _OBJECT_MAPPING.validate_python(value)
+    except ValidationError:
+        return None
+
+
+def _drop_keys(mapping: ObjectMapping, keys: frozenset[str]) -> ObjectMapping:
+    return MappingProxyType({key: value for key, value in mapping.items() if key not in keys})
+
+
+def _budget_reservation(metadata: ObjectMapping) -> ObjectMapping | None:
+    """The admission-time reservation, wherever the request setup left it, so the sidecar can reconcile it."""
+    direct: Final = _mapping_or_none(metadata.get("user_api_key_budget_reservation"))
+    if direct is not None:
+        return direct
+    auth: Final = metadata.get("user_api_key_auth")
+    if isinstance(auth, UserAPIKeyAuth):
+        return auth.budget_reservation
+    auth_mapping: Final = _mapping_or_none(auth)
+    return _mapping_or_none(auth_mapping.get("budget_reservation")) if auth_mapping is not None else None
+
+
+def _metadata_for_event(
+    metadata: ObjectMapping | None, budget_reservation: ObjectMapping | None
+) -> ObjectMapping | None:
+    if metadata is None:
+        return None
+    kept: Final = _drop_keys(metadata, _UNSERIALIZABLE_METADATA_KEYS)
+    if budget_reservation is None:
+        return kept
+    return MappingProxyType({**kept, "user_api_key_budget_reservation": budget_reservation})
+
+
+def _litellm_params_for_event(
+    litellm_params: _LitellmParams, cache_key: str | None, store_bodies: bool
+) -> _LitellmParams:
+    metadata: Final = litellm_params.get("metadata")
+    litellm_metadata: Final = litellm_params.get("litellm_metadata")
+    budget_reservation: Final = next(
+        (
+            reservation
+            for source in (litellm_metadata, metadata)
+            if source is not None and (reservation := _budget_reservation(source)) is not None
+        ),
+        None,
+    )
+    projected: Final[_LitellmParams] = {
+        "api_base": litellm_params.get("api_base"),
+        "custom_llm_provider": litellm_params.get("custom_llm_provider"),
+        "litellm_call_id": litellm_params.get("litellm_call_id"),
+        "user_api_key_end_user_id": litellm_params.get("user_api_key_end_user_id"),
+        "metadata": _metadata_for_event(metadata, budget_reservation),
+        "litellm_metadata": _metadata_for_event(litellm_metadata, budget_reservation),
+        "proxy_server_request": litellm_params.get("proxy_server_request") if store_bodies else None,
+        "preset_cache_key": cache_key,
+    }
+    return projected
+
+
+def _standard_logging_for_event(sl_object: ObjectMapping | None, store_bodies: bool) -> ObjectMapping | None:
+    if sl_object is None:
+        return None
+    dropped: Final = (
+        _STANDARD_LOGGING_DROPPED_KEYS if store_bodies else _STANDARD_LOGGING_DROPPED_KEYS | _STANDARD_LOGGING_BODY_KEYS
+    )
+    return _drop_keys(sl_object, dropped)
+
+
+def _tool_call(name: str) -> _ToolCall:
+    tool_call: Final[_ToolCall] = {"id": None, "type": "function", "function": {"name": name, "arguments": "{}"}}
+    return tool_call
+
+
+def _tool_call_choice(names: Sequence[str]) -> _ToolCallChoice:
+    choice: Final[_ToolCallChoice] = {
+        "index": 0,
+        "finish_reason": "tool_calls",
+        "message": {"role": "assistant", "content": None, "tool_calls": tuple(_tool_call(name) for name in names)},
+    }
+    return choice
+
+
+def _compact_response(response_obj: object) -> CompactResponse | None:
+    """Usage, identity and tool calls of the response, in chat-completions shape, without the content."""
+    dumped: Final = response_obj.model_dump() if isinstance(response_obj, BaseModel) else _mapping_or_none(response_obj)
+    if dumped is None:
+        return None
+    scalars: Final = _COMPACT_RESPONSE.validate_python(_drop_keys(dumped, frozenset({"choices"})))
+    tool_call_names: Final = response_tool_call_names(response_obj)
+    if not tool_call_names:
+        return scalars
+    with_tool_calls: Final[CompactResponse] = {**scalars, "choices": (_tool_call_choice(tool_call_names),)}
+    return with_tool_calls
+
+
+def _tool_name(tool: ObjectMapping) -> str | None:
+    """Chat tools nest the name under ``function``; Anthropic and Responses API tools keep it at the top."""
+    function: Final = _mapping_or_none(tool.get("function"))
+    name: Final = function.get("name") if function is not None else tool.get("name")
+    return name.strip() if isinstance(name, str) and name.strip() else None
+
+
+def _request_tool_names(kwargs: _SuccessKwargs) -> tuple[str, ...]:
+    passthrough: Final = kwargs.get("passthrough_logging_payload")
+    request_body: Final = passthrough.get("request_body") if passthrough is not None else None
+    passthrough_tools: Final = request_body.get("tools") if request_body is not None else None
+    return tuple(
+        name
+        for source in (kwargs.get("tools"), passthrough_tools)
+        if source is not None
+        for tool in source
+        if (name := _tool_name(tool)) is not None
+    )
+
+
+def preset_spend_log_cache_key(litellm_params: _LitellmParams) -> str | None:
+    """The key the caching layer already stored in ``litellm_params``, or ``Cache OFF``; never hashes the body."""
+    if litellm.cache is None:
+        return CACHE_OFF_KEY
+    return litellm_params.get("preset_cache_key")
+
+
+def _function_tool(name: str) -> _FunctionTool:
+    tool: Final[_FunctionTool] = {"type": "function", "function": {"name": name}}
+    return tool
+
+
+def build_spend_event(
+    raw_kwargs: ObjectMapping, response_obj: object, start_time: datetime, end_time: datetime, store_bodies: bool
+) -> bytes | SpendEventBuildError:
+    """Validate the success callback's kwargs and serialize the event once, as a single JSON line."""
+    try:
+        kwargs: Final = _SUCCESS_KWARGS.validate_python(raw_kwargs)
+    except ValidationError as error:
+        return SpendEventBuildError(reason=str(error))
+    litellm_params: Final = kwargs.get("litellm_params", _NO_LITELLM_PARAMS)
+    sl_object: Final = kwargs.get("standard_logging_object")
+    cache_key: Final = preset_spend_log_cache_key(litellm_params)
+    response_cost: Final = sl_object.get("response_cost") if sl_object is not None else kwargs.get("response_cost")
+    combined_usage: Final = kwargs.get("combined_usage_object")
+    event: Final = SpendEvent(
+        version=SPEND_EVENT_VERSION,
+        litellm_call_id=kwargs.get("litellm_call_id"),
+        call_type=kwargs.get("call_type"),
+        model=kwargs.get("model"),
+        custom_llm_provider=kwargs.get("custom_llm_provider"),
+        stream=kwargs.get("stream"),
+        complete_streaming_response="complete_streaming_response" in kwargs,
+        cache_hit=kwargs.get("cache_hit"),
+        response_cost=response_cost if isinstance(response_cost, (int, float)) else None,
+        start_time=start_time,
+        end_time=end_time,
+        completion_start_time=kwargs.get("completion_start_time"),
+        agent_id=kwargs.get("agent_id"),
+        litellm_trace_id=kwargs.get("litellm_trace_id"),
+        litellm_params=_litellm_params_for_event(litellm_params, cache_key, store_bodies),
+        standard_logging_object=_standard_logging_for_event(sl_object, store_bodies),
+        standard_callback_dynamic_params=kwargs.get("standard_callback_dynamic_params"),
+        response=_compact_response(response_obj),
+        combined_usage=combined_usage.model_dump() if combined_usage is not None else None,
+        realtime_tools=kwargs.get("realtime_tools"),
+        realtime_tool_calls=kwargs.get("realtime_tool_calls"),
+        request_tool_names=_request_tool_names(kwargs),
+    )
+    return event.model_dump_json(fallback=_json_fallback).encode() + b"\n"
+
+
+def decode_spend_event(line: bytes) -> SpendEvent | SpendEventDecodeError:
+    try:
+        return SpendEvent.model_validate_json(line)
+    except ValidationError as error:
+        return SpendEventDecodeError(reason=str(error))
+
+
+def spend_event_callback_args(event: SpendEvent) -> SpendEventCallbackArgs:
+    """The ``(kwargs, response_obj, start_time, end_time)`` the in-process cost callback receives."""
+    tools: Final = tuple(_function_tool(name) for name in event.request_tool_names)
+    kwargs: Final[SpendCallbackKwargs] = {
+        "litellm_call_id": event.litellm_call_id,
+        "call_type": event.call_type,
+        "model": event.model,
+        "custom_llm_provider": event.custom_llm_provider,
+        "stream": event.stream,
+        "cache_hit": event.cache_hit,
+        "response_cost": event.response_cost,
+        "completion_start_time": event.completion_start_time,
+        "agent_id": event.agent_id,
+        "litellm_trace_id": event.litellm_trace_id,
+        "litellm_params": event.litellm_params,
+        "standard_logging_object": event.standard_logging_object,
+        "standard_callback_dynamic_params": event.standard_callback_dynamic_params,
+        "combined_usage_object": Usage.model_validate(event.combined_usage)
+        if event.combined_usage is not None
+        else None,
+        "realtime_tools": event.realtime_tools,
+        "realtime_tool_calls": event.realtime_tool_calls,
+        "tools": tools or None,
+    }
+    if not event.complete_streaming_response:
+        return SpendEventCallbackArgs(kwargs, event.response, event.start_time, event.end_time)
+    streaming_kwargs: Final[SpendCallbackKwargs] = {**kwargs, "complete_streaming_response": event.response}
+    return SpendEventCallbackArgs(streaming_kwargs, event.response, event.start_time, event.end_time)
diff --git a/litellm/proxy/spend_tracking/spend_event_producer.py b/litellm/proxy/spend_tracking/spend_event_producer.py
new file mode 100644
index 00000000000..20c7f177af0
--- /dev/null
+++ b/litellm/proxy/spend_tracking/spend_event_producer.py
@@ -0,0 +1,338 @@
+"""Fire-and-forget push of serialized spend events from an inference worker to the pod-local sidecar.
+
+``LITELLM_COLLECTOR_ENABLED=true`` turns the push on in the gateway; the sidecar process sets
+``LITELLM_JOB_ROLE=collector`` and always runs the pipeline in-process. Events queue in a bounded
+in-memory buffer that a single writer task flushes over a unix socket or loopback TCP connection.
+When the sidecar is unreachable, the buffer is full, or the connection breaks mid-write, each affected
+event follows ``LITELLM_COLLECTOR_ON_UNAVAILABLE``: ``fallback`` runs the existing cost pipeline in
+the worker, ``drop`` counts it and moves on. Transitions are logged with the counters, so a sidecar
+outage is visible without scraping anything.
+
+Delivery is at-most-once: a sidecar crash loses the events the kernel already took from its socket.
+A sidecar that stops gracefully half-closes each connection first (EOF towards the producer) and
+keeps reading until the producer hangs up, so the producer switches to the unavailable policy without
+losing the events in flight. A write that fails part-way follows the unavailable policy without double
+counting: ``drain()`` only fails while part of the line is still buffered in this process, so the
+sidecar can at most have read a truncated line, which it discards. When the gateway itself stops with
+the writer stuck mid-send, only an event whose bytes are still in the producer's write buffer follows
+the unavailable policy; the connection is aborted first so the sidecar discards the truncated line
+instead of also counting it. Events from one uvicorn worker are handled in the order it produced them;
+events from different workers interleave, exactly like the in-process callbacks do today.
+"""
+
+import asyncio
+import ipaddress
+import time
+from collections.abc import Awaitable, Callable
+from dataclasses import dataclass
+from typing import Final, Literal, TypeAlias
+from urllib.parse import urlsplit
+
+from pydantic import AliasChoices, Field
+from pydantic_settings import BaseSettings, SettingsConfigDict
+
+from litellm._logging import verbose_proxy_logger
+
+COLLECTOR_ENV_PREFIX: Final = "LITELLM_COLLECTOR_"
+COLLECTOR_JOB_ROLE: Final = "collector"
+DEFAULT_COLLECTOR_ADDRESS: Final = "unix:///var/run/litellm/collector.sock"
+RECONNECT_BACKOFF_SECONDS: Final = 1.0
+DROP_LOG_EVERY: Final = 1000
+
+UnavailablePolicy: TypeAlias = Literal["fallback", "drop"]
+PublishOutcome: TypeAlias = Literal["queued", "fallback", "dropped"]
+
+
+class CollectorSettings(BaseSettings):
+    """``LITELLM_COLLECTOR_*`` env vars, shared by the gateway producer and the sidecar consumer."""
+
+    model_config = SettingsConfigDict(
+        env_prefix=COLLECTOR_ENV_PREFIX, case_sensitive=False, extra="ignore", frozen=True, populate_by_name=True
+    )
+
+    enabled: bool = False
+    address: str = DEFAULT_COLLECTOR_ADDRESS
+    buffer_size: int = Field(default=1000, ge=1)
+    on_unavailable: UnavailablePolicy = "fallback"
+    drain_timeout_seconds: float = Field(default=10.0, gt=0)
+    connect_timeout_seconds: float = Field(default=1.0, gt=0)
+    job_role: str | None = Field(default=None, validation_alias=AliasChoices("LITELLM_JOB_ROLE"))
+
+    @property
+    def produces(self) -> bool:
+        return self.enabled and self.job_role != COLLECTOR_JOB_ROLE
+
+
+@dataclass(frozen=True, slots=True)
+class UnixAddress:
+    path: str
+
+
+@dataclass(frozen=True, slots=True)
+class TcpAddress:
+    host: str
+    port: int
+
+
+@dataclass(frozen=True, slots=True)
+class AddressError:
+    reason: str
+
+
+CollectorAddress: TypeAlias = UnixAddress | TcpAddress
+
+
+def _is_loopback(host: str) -> bool:
+    try:
+        return ipaddress.ip_address(host).is_loopback
+    except ValueError:
+        return host == "localhost"
+
+
+def parse_collector_address(address: str) -> CollectorAddress | AddressError:
+    """``unix:///path/to.sock`` or ``tcp://127.0.0.1:port``; the socket carries unauthenticated spend events."""
+    parsed: Final = urlsplit(address)
+    if parsed.scheme == "unix" and parsed.path:
+        return UnixAddress(path=parsed.path)
+    if parsed.scheme == "tcp" and parsed.hostname and parsed.port is not None:
+        if not _is_loopback(parsed.hostname):
+            return AddressError(reason=f"tcp collector address must be a loopback host, got {address!r}")
+        return TcpAddress(host=parsed.hostname, port=parsed.port)
+    return AddressError(reason=f"expected unix:///path or tcp://127.0.0.1:port, got {address!r}")
+
+
+async def open_collector_connection(
+    address: CollectorAddress, timeout: float
+) -> tuple[asyncio.StreamReader, asyncio.StreamWriter]:
+    match address:
+        case UnixAddress(path=path):
+            return await asyncio.wait_for(asyncio.open_unix_connection(path), timeout)
+        case TcpAddress(host=host, port=port):
+            return await asyncio.wait_for(asyncio.open_connection(host, port), timeout)
+
+
+def build_spend_event_producer(
+    settings: CollectorSettings, fallback: Callable[[bytes], Awaitable[None]]
+) -> "SpendEventProducer | None":
+    """The gateway producer for these settings, or ``None`` when the pipeline stays in-process."""
+    if not settings.produces:
+        return None
+    address: Final = parse_collector_address(settings.address)
+    if isinstance(address, AddressError):
+        verbose_proxy_logger.error("collector: %s; running the spend pipeline in-process", address.reason)
+        return None
+    verbose_proxy_logger.info(
+        "collector: offloading spend tracking to %s (buffer=%d, on_unavailable=%s)",
+        settings.address,
+        settings.buffer_size,
+        settings.on_unavailable,
+    )
+    return SpendEventProducer(
+        address=address,
+        on_unavailable=settings.on_unavailable,
+        buffer_size=settings.buffer_size,
+        connect_timeout=settings.connect_timeout_seconds,
+        fallback=fallback,
+    )
+
+
+@dataclass(frozen=True, slots=True)
+class _Connection:
+    reader: asyncio.StreamReader
+    writer: asyncio.StreamWriter
+
+    @property
+    def alive(self) -> bool:
+        return not self.writer.is_closing() and not self.reader.at_eof()
+
+
+@dataclass(frozen=True, slots=True)
+class SpendEventProducerStats:
+    queued: int
+    sent: int
+    fallback: int
+    dropped: int
+    connected: bool
+
+
+class SpendEventProducer:
+    """Bounded buffer plus one writer task per process; see the module docstring for the contract."""
+
+    def __init__(
+        self,
+        address: CollectorAddress,
+        on_unavailable: UnavailablePolicy,
+        buffer_size: int,
+        connect_timeout: float,
+        fallback: Callable[[bytes], Awaitable[None]],
+        clock: Callable[[], float] = time.monotonic,
+        open_connection: Callable[
+            [CollectorAddress, float], Awaitable[tuple[asyncio.StreamReader, asyncio.StreamWriter]]
+        ] = open_collector_connection,
+    ) -> None:
+        self._address = address
+        self._on_unavailable = on_unavailable
+        self._buffer_size = buffer_size
+        self._connect_timeout = connect_timeout
+        self._fallback = fallback
+        self._clock = clock
+        self._open_connection = open_connection
+        self._queue: asyncio.Queue[bytes] | None = None
+        self._writer_task: asyncio.Task[None] | None = None
+        self._connection: _Connection | None = None
+        self._in_flight: bytes | None = None
+        self._closing = False
+        self._next_connect_at = 0.0
+        self._queued = 0
+        self._sent = 0
+        self._fallback_count = 0
+        self._dropped = 0
+
+    def stats(self) -> SpendEventProducerStats:
+        return SpendEventProducerStats(
+            queued=self._queued,
+            sent=self._sent,
+            fallback=self._fallback_count,
+            dropped=self._dropped,
+            connected=self._connection is not None,
+        )
+
+    async def publish(self, line: bytes) -> PublishOutcome:
+        """Hand one serialized event to the writer task, or apply the unavailable policy right away."""
+        if self._closing or self._clock() < self._next_connect_at:
+            return await self._unavailable(line, "sidecar unreachable")
+        queue: Final = self._ensure_writer()
+        try:
+            queue.put_nowait(line)
+        except asyncio.QueueFull:
+            return await self._unavailable(line, "buffer full")
+        self._queued += 1
+        return "queued"
+
+    async def close(self, drain_timeout: float) -> None:
+        """Flush the buffer for up to ``drain_timeout`` seconds, then apply the unavailable policy to the rest."""
+        self._closing = True
+        queue: Final = self._queue
+        task: Final = self._writer_task
+        if queue is None or task is None:
+            return
+        try:
+            await asyncio.wait_for(queue.join(), drain_timeout)
+        except asyncio.TimeoutError:
+            verbose_proxy_logger.warning(
+                "collector: %s events still buffered after %.1fs drain timeout", queue.qsize(), drain_timeout
+            )
+        task.cancel()
+        try:
+            await task
+        except asyncio.CancelledError:
+            pass
+        unsent: Final = self._take_unsent()
+        await self._disconnect()
+        if unsent is not None:
+            await self._unavailable(unsent, "shutdown")
+        while not queue.empty():
+            await self._unavailable(queue.get_nowait(), "shutdown")
+
+    def _take_unsent(self) -> bytes | None:
+        """The in-flight event if any of its bytes never left this process, aborting the half-written connection."""
+        in_flight: Final = self._in_flight
+        self._in_flight = None
+        connection: Final = self._connection
+        if in_flight is None:
+            return None
+        if connection is None:
+            return in_flight
+        if connection.writer.transport.get_write_buffer_size() == 0:
+            return None
+        connection.writer.transport.abort()
+        return in_flight
+
+    def _ensure_writer(self) -> asyncio.Queue[bytes]:
+        if self._queue is None:
+            self._queue = asyncio.Queue(maxsize=self._buffer_size)
+        if self._writer_task is None or self._writer_task.done():
+            self._writer_task = asyncio.get_running_loop().create_task(self._run_writer(self._queue))
+        return self._queue
+
+    async def _run_writer(self, queue: asyncio.Queue[bytes]) -> None:
+        while True:
+            line = await queue.get()
+            try:
+                await self._send(line)
+            finally:
+                queue.task_done()
+
+    async def _send(self, line: bytes) -> None:
+        self._in_flight = line
+        connection: Final = await self._connect()
+        if connection is None:
+            self._in_flight = None
+            await self._unavailable(line, "sidecar unreachable")
+            return
+        try:
+            connection.writer.write(line)
+            await connection.writer.drain()
+        except (ConnectionError, OSError, RuntimeError) as error:  # uvloop: RuntimeError on a closed transport
+            self._in_flight = None
+            await self._disconnect()
+            self._next_connect_at = self._clock() + RECONNECT_BACKOFF_SECONDS
+            await self._unavailable(line, f"write failed: {error}")
+            return
+        self._in_flight = None
+        self._sent += 1
+
+    async def _connect(self) -> _Connection | None:
+        if self._connection is not None and self._connection.alive:
+            return self._connection
+        await self._disconnect()
+        if self._clock() < self._next_connect_at:
+            return None
+        try:
+            reader, writer = await self._open_connection(self._address, self._connect_timeout)
+        except (ConnectionError, OSError, asyncio.TimeoutError) as error:
+            self._next_connect_at = self._clock() + RECONNECT_BACKOFF_SECONDS
+            verbose_proxy_logger.warning(
+                "collector: cannot reach %s (%s); applying %s policy for %.0fs. stats=%s",
+                self._address,
+                error,
+                self._on_unavailable,
+                RECONNECT_BACKOFF_SECONDS,
+                self.stats(),
+            )
+            return None
+        self._connection = _Connection(reader=reader, writer=writer)
+        verbose_proxy_logger.info("collector: connected to %s. stats=%s", self._address, self.stats())
+        return self._connection
+
+    async def _disconnect(self) -> None:
+        connection: Final = self._connection
+        self._connection = None
+        if connection is None:
+            return
+        connection.writer.close()
+        try:
+            await connection.writer.wait_closed()
+        except (ConnectionError, OSError):
+            pass
+
+    async def _unavailable(self, line: bytes, reason: str) -> PublishOutcome:
+        if self._on_unavailable == "fallback":
+            self._fallback_count += 1
+            fallback: Final = asyncio.ensure_future(self._run_fallback(line, reason))
+            try:
+                await asyncio.shield(fallback)
+            except asyncio.CancelledError:
+                await fallback
+                raise
+            return "fallback"
+        self._dropped += 1
+        if self._dropped % DROP_LOG_EVERY == 1:
+            verbose_proxy_logger.warning("collector: dropping spend event (%s). stats=%s", reason, self.stats())
+        return "dropped"
+
+    async def _run_fallback(self, line: bytes, reason: str) -> None:
+        try:
+            await self._fallback(line)
+        except Exception:  # noqa: BLE001  # one failing event must not kill the writer task
+            verbose_proxy_logger.exception("collector: in-process fallback failed (%s)", reason)
diff --git a/litellm/proxy/spend_tracking/spend_management_endpoints.py b/litellm/proxy/spend_tracking/spend_management_endpoints.py
index f8831ca4152..da79328fa59 100644
--- a/litellm/proxy/spend_tracking/spend_management_endpoints.py
+++ b/litellm/proxy/spend_tracking/spend_management_endpoints.py
@@ -26,7 +26,12 @@ from typing_extensions import ReadOnly
 
 import litellm
 from litellm._logging import verbose_proxy_logger
-from litellm.constants import LITTELM_INTERNAL_HEALTH_SERVICE_ACCOUNT_NAME
+from litellm.constants import (
+    EMPTY_MAPPING,
+    LITELLM_TRUNCATED_PAYLOAD_FIELD,
+    LITTELM_INTERNAL_HEALTH_SERVICE_ACCOUNT_NAME,
+)
+from litellm.litellm_core_utils.classifier_logging import classifier_audit_fields, classifier_input_snapshot
 from litellm.proxy._types import *
 from litellm.proxy._types import ProviderBudgetResponse, ProviderBudgetResponseObject
 from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
@@ -3099,7 +3104,11 @@ async def _resolve_request_response_payload(
     proxy_server_request: Final = row.get("proxy_server_request")
 
     pg_payload: Final = RequestResponsePayload(messages, response, proxy_server_request)
-    if (
+    stored_request: Final = classifier_input_snapshot(proxy_server_request)
+    truncated_audit: Final = bool(stored_request and classifier_audit_fields(stored_request)) and (
+        LITELLM_TRUNCATED_PAYLOAD_FIELD in str(proxy_server_request)
+    )
+    if not truncated_audit and (
         _spend_log_field_has_content(messages)
         or _spend_log_field_has_content(response)
         or _spend_log_field_has_content(proxy_server_request)
@@ -3124,10 +3133,22 @@ async def _resolve_request_response_payload(
     if payload is None:
         return pg_payload
 
+    cold_audit: Final = classifier_audit_fields(payload)
+    resolved_request: Final = (
+        {
+            **(classifier_input_snapshot(payload.get("proxy_server_request")) or stored_request or EMPTY_MAPPING),
+            **cold_audit,
+        }
+        if cold_audit
+        else payload.get("proxy_server_request")
+    )
+    if truncated_audit:
+        return RequestResponsePayload(messages, response, resolved_request if cold_audit else proxy_server_request)
+
     return RequestResponsePayload(
         messages=payload.get("messages"),
         response=payload.get("response"),
-        proxy_server_request=payload.get("proxy_server_request"),
+        proxy_server_request=resolved_request,
     )
 
 
@@ -4633,16 +4654,16 @@ async def _assert_user_can_view_request_id(
     Verify the requesting non-admin user is allowed to view this spend-log row.
     Allowed when the log belongs to the user directly, or to one of their
     permitted teams (admin or ``/spend/logs`` permission).
-    Raises HTTP 403 if not.
+    Raises HTTP 403 if not, including when no spend-log row exists for the
+    request_id (e.g. it was pruned by retention), so a missing row can't be
+    used to read a payload out of cold storage via the detail endpoint.
     """
     row: Final = await _find_spend_log_row(prisma_client, request_id)
-    if row is None:
+
+    if row is not None and row.user is not None and row.user == user_api_key_dict.user_id:
         return
 
-    if row.user is not None and row.user == user_api_key_dict.user_id:
-        return
-
-    if row.team_id:
+    if row is not None and row.team_id:
         can_view: Final = await _can_team_member_view_log(
             prisma_client=prisma_client,
             user_api_key_dict=user_api_key_dict,
diff --git a/litellm/proxy/spend_tracking/spend_tracking_utils.py b/litellm/proxy/spend_tracking/spend_tracking_utils.py
index a21d761996f..f0f38358cf0 100644
--- a/litellm/proxy/spend_tracking/spend_tracking_utils.py
+++ b/litellm/proxy/spend_tracking/spend_tracking_utils.py
@@ -4,6 +4,7 @@ import secrets
 from collections.abc import Mapping, Sequence
 from datetime import datetime, timezone
 from datetime import datetime as dt
+from types import MappingProxyType
 from typing import Final, Literal, Protocol, cast, runtime_checkable
 
 from pydantic import BaseModel
@@ -11,17 +12,21 @@ from pydantic import BaseModel
 import litellm
 from litellm._logging import verbose_proxy_logger
 from litellm.constants import (
+    EMPTY_MAPPING,
     LITELLM_PROXY_MASTER_KEY_ALIAS,
     LITELLM_TRUNCATED_PAYLOAD_FIELD,
     LITELLM_TRUNCATION_DB_SAFEGUARD_NOTE,
     LITTELM_CLI_SERVICE_ACCOUNT_NAME,
     LITTELM_INTERNAL_HEALTH_SERVICE_ACCOUNT_NAME,
+    MAX_SPEND_LOG_MODEL_NAME_LENGTH,
     REDACTED_BY_LITELM_STRING,
     SESSION_ID_OMITTED_METADATA_KEY,
+    UNKNOWN_MODEL_SPEND_LOG_MODEL,
 )
 from litellm.constants import (
     MAX_STRING_LENGTH_PROMPT_IN_DB as DEFAULT_MAX_STRING_LENGTH_PROMPT_IN_DB,
 )
+from litellm.litellm_core_utils.classifier_logging import classifier_audit_fields, without_classifier_audit
 from litellm.litellm_core_utils.core_helpers import (
     get_litellm_metadata_from_kwargs,
     reconstruct_model_name,
@@ -34,6 +39,7 @@ from litellm.litellm_core_utils.litellm_logging import (
 )
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps, strip_null_bytes
 from litellm.proxy._types import SpendLogsMetadata, SpendLogsPayload, SpendLogsRouterMetadata
+from litellm.proxy.route_llm_request import ProxyModelNotFoundError
 from litellm.proxy.spend_tracking.spend_log_error_logger import spend_log_error
 from litellm.proxy.utils import PrismaClient, hash_token
 from litellm.types.utils import (
@@ -331,10 +337,15 @@ def _sl_attribution_fallback(
     return standard_logging_payload.get(field) or ""
 
 
+def _looks_like_model_name(model: str) -> bool:
+    return len(model) <= MAX_SPEND_LOG_MODEL_NAME_LENGTH and not any(char.isspace() for char in model)
+
+
 def get_logging_payload(kwargs, response_obj, start_time, end_time) -> SpendLogsPayload:
     if kwargs is None:
         kwargs = {}
 
+    rejected_as_unknown_model: Final = isinstance(response_obj, ProxyModelNotFoundError)
     if response_obj is None:
         response_obj = {}
     elif not isinstance(response_obj, BaseModel) and not isinstance(response_obj, dict):
@@ -432,9 +443,19 @@ def get_logging_payload(kwargs, response_obj, start_time, end_time) -> SpendLogs
         or None
     )
     raw_model: Final = cast(str, kwargs.get("model") or "")
-    model_name: Final = (
+    resolved_model: Final = (
         standard_logging_payload.get("model") if standard_logging_payload is not None else None
     ) or reconstruct_model_name(raw_model, custom_llm_provider, metadata or {})
+    failed_with_prompt_shaped_model: Final = (
+        _get_status_for_spend_log(metadata=metadata) == "failure"
+        and not _model_group
+        and not _looks_like_model_name(resolved_model)
+    )
+    model_name: Final = (
+        UNKNOWN_MODEL_SPEND_LOG_MODEL
+        if rejected_as_unknown_model or failed_with_prompt_shaped_model
+        else resolved_model
+    )
     litellm_call_id: Final = cast(
         str | None,
         kwargs.get("litellm_call_id") or litellm_params.get("litellm_call_id"),
@@ -533,10 +554,12 @@ def get_logging_payload(kwargs, response_obj, start_time, end_time) -> SpendLogs
                 additional_usage_values["cache_creation_input_tokens"] = cache_write_tokens
     clean_metadata["additional_usage_values"] = additional_usage_values
 
-    if litellm.cache is not None:
-        cache_key = litellm.cache.get_cache_key(**kwargs)
-    else:
+    if litellm.cache is None:
         cache_key = "Cache OFF"
+    elif litellm_params.get("preset_cache_key") is not None:
+        cache_key = litellm_params["preset_cache_key"]
+    else:
+        cache_key = litellm.cache.get_cache_key(**kwargs)
     if cache_hit is True:
         import time
 
@@ -843,7 +866,7 @@ def _get_messages_for_spend_logs_payload(
     standard_logging_payload: StandardLoggingPayload | None,
     metadata: dict | None = None,
 ) -> str:
-    if _should_store_prompts_and_responses_in_spend_logs():
+    if should_store_prompts_and_responses_in_spend_logs():
         if standard_logging_payload is not None:
             call_type: Final = standard_logging_payload.get("call_type", "")
             if call_type == "_arealtime":
@@ -860,7 +883,7 @@ _SENSITIVE_REQUEST_BODY_KEYS: Final = frozenset({"secret_fields"})
 
 
 def _sanitize_request_body_for_spend_logs_payload(
-    request_body: dict,
+    request_body: Mapping[str, object],
     visited: set | None = None,
     max_string_length_prompt_in_db: int | None = None,
 ) -> dict:
@@ -1093,7 +1116,7 @@ def _sanitize_guardrail_information_for_spend_logs(
     here to match OTEL's defensive read pattern; otherwise iteration would
     yield the dict's keys and crash the whole spend-log write.
     """
-    if guardrail_information is None or _should_store_prompts_and_responses_in_spend_logs():
+    if guardrail_information is None or should_store_prompts_and_responses_in_spend_logs():
         return guardrail_information
     entries: Final = [guardrail_information] if isinstance(guardrail_information, dict) else guardrail_information
     return [_redact_prompt_fields_in_guardrail_entry(entry) for entry in entries if isinstance(entry, dict)]
@@ -1165,7 +1188,7 @@ def _sanitize_error_information_for_spend_logs(
 
     sanitized = cast(dict, {**error_information})
 
-    if not _should_store_prompts_and_responses_in_spend_logs():
+    if not should_store_prompts_and_responses_in_spend_logs():
         for field in ("error_message", "traceback"):
             value = sanitized.get(field)
             if isinstance(value, str):
@@ -1242,14 +1265,18 @@ def _get_proxy_server_request_for_spend_logs_payload(
     kwargs: dict | None = None,
 ) -> str:
     """
-    Only store if _should_store_prompts_and_responses_in_spend_logs() is True
+    Only store if should_store_prompts_and_responses_in_spend_logs() is True
 
     If turn_off_message_logging is enabled, redact messages in the request body.
     """
-    if _should_store_prompts_and_responses_in_spend_logs():
-        _proxy_server_request: Final = cast(dict | None, litellm_params.get("proxy_server_request", {}))
+    if should_store_prompts_and_responses_in_spend_logs():
+        _proxy_server_request: Final = cast(dict | None, litellm_params.get("proxy_server_request", EMPTY_MAPPING))
         if _proxy_server_request is not None:
-            _request_body = _proxy_server_request.get("body", {}) or {}
+            _request_body = _proxy_server_request.get("body", EMPTY_MAPPING) or EMPTY_MAPPING
+
+            standard_payload: Final = (kwargs or EMPTY_MAPPING).get("standard_logging_object")
+            if isinstance(standard_payload, Mapping):
+                _request_body = MappingProxyType({**_request_body, **classifier_audit_fields(standard_payload)})
 
             if kwargs is not None:
                 realtime_tools: Final = kwargs.get("realtime_tools")
@@ -1272,7 +1299,7 @@ def _get_proxy_server_request_for_spend_logs_payload(
 
                 # If redaction is enabled, convert to serializable dict before redacting
                 if should_redact_message_logging(model_call_details=model_call_details):
-                    _request_body = _convert_mapping_to_json_serializable(_request_body)
+                    _request_body = _convert_mapping_to_json_serializable(without_classifier_audit(_request_body))
                     perform_redaction(model_call_details=_request_body, result=None)
 
             _request_body = _sanitize_request_body_for_spend_logs_payload(_request_body)
@@ -1292,7 +1319,7 @@ def _get_vector_store_request_for_spend_logs_payload(
     """
     If user does not want to store prompts and responses, then remove the content from the vector store request metadata
     """
-    if _should_store_prompts_and_responses_in_spend_logs():
+    if should_store_prompts_and_responses_in_spend_logs():
         return vector_store_request_metadata
 
     # if user does not want to store prompts and responses, then remove the content from the vector store request metadata
@@ -1316,7 +1343,7 @@ def _get_response_for_spend_logs_payload(
 ) -> str:
     if payload is None:
         return "{}"
-    if _should_store_prompts_and_responses_in_spend_logs():
+    if should_store_prompts_and_responses_in_spend_logs():
         response_obj: object = payload.get("response")
         if response_obj is None:
             return "{}"
@@ -1364,7 +1391,7 @@ def _get_response_for_spend_logs_payload(
     return "{}"
 
 
-def _should_store_prompts_and_responses_in_spend_logs() -> bool:
+def should_store_prompts_and_responses_in_spend_logs() -> bool:
     from litellm.proxy.proxy_server import general_settings
     from litellm.secret_managers.main import get_secret_bool
 
diff --git a/litellm/proxy/utils.py b/litellm/proxy/utils.py
index 53aa372d1a1..253494b02f4 100644
--- a/litellm/proxy/utils.py
+++ b/litellm/proxy/utils.py
@@ -68,6 +68,7 @@ except ImportError:
     raise ImportError("backoff is not installed. Please install it via 'pip install backoff'")
 
 from fastapi import HTTPException, status
+from pydantic import TypeAdapter
 
 import litellm
 import litellm.litellm_core_utils
@@ -94,12 +95,14 @@ from litellm.integrations.SlackAlerting.slack_alerting import SlackAlerting
 from litellm.integrations.SlackAlerting.utils import _add_langfuse_trace_id_to_alert
 from litellm.litellm_core_utils.core_helpers import (
     coerce_token_limit,
+    get_or_create_metadata_bucket,
     independent_snapshot,
     is_expected_client_error,
 )
 from litellm.litellm_core_utils.litellm_logging import Logging
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
 from litellm.litellm_core_utils.safe_json_loads import safe_json_loads
+from litellm.litellm_core_utils.token_counter import offload_token_count
 from litellm.llms import load_guardrail_translation_mappings
 from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
 from litellm.proxy._types import (
@@ -122,7 +125,13 @@ from litellm.proxy.db.exception_handler import (
     PrismaDBExceptionHandler,
     call_with_db_reconnect_retry,
 )
+from litellm.proxy.db.health_check_latest import (
+    LatestHealthCheckRow,
+    fetch_latest_health_checks,
+    fetch_latest_health_checks_for_models,
+)
 from litellm.proxy.db.log_db_metrics import log_db_metrics
+from litellm.proxy.db.pgbouncer import database_url_is_pooled
 from litellm.proxy.db.prisma_client import (
     PrismaWrapper,
     parse_iam_endpoint_from_url,
@@ -157,6 +166,8 @@ from litellm.proxy.hooks.sensitive_data_routing import (
 from litellm.proxy.litellm_pre_call_utils import LiteLLMProxyRequestSetup, add_guardrails_from_auth_metadata
 from litellm.proxy.management_helpers.key_settings_audit import with_settings_updated_at
 from litellm.proxy.policy_engine.pipeline_executor import PipelineExecutor
+from litellm.proxy.policy_engine.policy_registry import get_policy_registry
+from litellm.proxy.policy_engine.policy_resolver import PolicyResolver
 from litellm.repositories.budget_repository import BudgetRepository
 from litellm.repositories.config_repository import ConfigRepository
 from litellm.repositories.table_repositories import (
@@ -172,6 +183,7 @@ from litellm.repositories.verification_token_repository import (
 )
 from litellm.secret_managers.main import str_to_bool
 from litellm.types.integrations.slack_alerting import DEFAULT_ALERT_TYPES
+from litellm.types.llms.openai import ResponsesAPIResponse
 from litellm.types.mcp import (
     MCPDuringCallResponseObject,
     MCPPreCallRequestObject,
@@ -193,6 +205,7 @@ if TYPE_CHECKING:
     from prisma.types import HttpConfig
 
     from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
+    from litellm.llms.base_llm.guardrail_translation.base_translation import BaseTranslation
     from litellm.models.team import LiteLLM_TeamTableCachedObj
     from litellm.proxy.db.autorouter_session_rollup import AutoRouterTurnTransaction
     from litellm.proxy.db.spend_log_tool_index import ToolUsageTransaction
@@ -455,7 +468,7 @@ def _pipeline_step_guardrail_names(pipelines: Sequence[tuple[str, "GuardrailPipe
     return frozenset(step.guardrail for _policy_name, pipeline in pipelines for step in pipeline.steps)
 
 
-def _pipeline_managed_guardrail_names(
+def pipeline_managed_guardrail_names(
     data: Mapping[str, object], mode: Literal["pre_call", "post_call"]
 ) -> frozenset[str]:
     return _pipeline_step_guardrail_names(
@@ -518,9 +531,17 @@ def _merge_pipeline_metadata_writes(
         _merge_pipeline_metadata_bucket(data, bucket_key, modified_data.get(bucket_key))
 
 
-def _pipeline_step_supports_unified_streaming(guardrail_name: str) -> bool:
+def _pipeline_step_supports_streaming(guardrail_name: str, translation: "BaseTranslation | None") -> bool:
     callback: Final = PipelineExecutor.find_guardrail_callback(guardrail_name)
-    return callback is not None and PipelineExecutor.supports_unified_execution(callback)
+    if callback is None:
+        return False
+    if PipelineExecutor.supports_unified_execution(callback):
+        return True
+    return (
+        translation is not None
+        and type(translation).assembles_streamed_response
+        and PipelineExecutor.supports_streaming_execution(callback)
+    )
 
 
 def _post_call_pipelines(data: Mapping[str, object]) -> tuple[tuple[str, "GuardrailPipeline"], ...]:
@@ -529,50 +550,174 @@ def _post_call_pipelines(data: Mapping[str, object]) -> tuple[tuple[str, "Guardr
     )
 
 
-def _warn_background_skips_post_call_pipelines(data: Mapping[str, object]) -> None:
-    if data.get("background") is not True:
-        return
-    policy_names: Final = tuple(policy_name for policy_name, _pipeline in _post_call_pipelines(data))
-    if not policy_names:
-        return
-    verbose_proxy_logger.warning(
-        "Policies with post_call guardrail pipelines do not run on background responses yet; "
-        "the response is released ungoverned by them: %s",
-        ", ".join(policy_names),
+_PENDING_BACKGROUND_RESPONSE_STATUSES: Final = frozenset(("queued", "in_progress"))
+
+
+def _is_pending_background_response(response: LLMResponseTypes) -> bool:
+    return isinstance(response, ResponsesAPIResponse) and response.status in _PENDING_BACKGROUND_RESPONSE_STATUSES
+
+
+def _guardrails_outside_pipeline(policy_name: str, pipeline: "GuardrailPipeline") -> frozenset[str]:
+    resolved: Final = PolicyResolver.resolve_policy_guardrails(
+        policy_name=policy_name, policies=get_policy_registry().get_all_policies()
+    )
+    return frozenset(resolved.guardrails) - frozenset(step.guardrail for step in pipeline.steps)
+
+
+def _guardrails_run_standalone_pre_call(data: Mapping[str, object]) -> frozenset[str]:
+    return frozenset(
+        callback.guardrail_name
+        for callback in litellm.callbacks
+        if isinstance(callback, CustomGuardrail)
+        and callback.guardrail_name is not None
+        and callback.should_run_guardrail(data=data, event_type=GuardrailEventHooks.pre_call)
     )
 
 
-def _pipeline_is_streamable(policy_name: str, pipeline: "GuardrailPipeline") -> bool:
-    unsupported: Final = tuple(
+def _without_names(
+    bucket: dict[str, object],  # mutable-ok: the applied_* header slots live in the request-state dict hooks write
+    slot: str,
+    names: frozenset[str],
+) -> None:
+    claimed: Final = bucket.get(slot)
+    if not isinstance(claimed, list):
+        return
+    remaining: Final = [  # mutable-ok: the slot stays a list, the shape every applied_* header writer appends to
+        name for name in claimed if name not in names
+    ]
+    if remaining:
+        bucket[slot] = remaining  # rebind-ok: the slot lives in the shared request-state dict, rewritten in place
+    else:
+        bucket.pop(slot)
+
+
+def _withdraw_deferred_claims(
+    data: dict[str, object],  # mutable-ok: same request-payload shape as post_call_success_hook's data
+    deferred: Sequence[tuple[str, "GuardrailPipeline"]],
+) -> None:
+    outside_by_policy: Final = MappingProxyType(
+        {policy_name: _guardrails_outside_pipeline(policy_name, pipeline) for policy_name, pipeline in deferred}
+    )
+    running_elsewhere: Final = pipeline_managed_guardrail_names(data, "pre_call").union(
+        _guardrails_run_standalone_pre_call(data), *outside_by_policy.values()
+    )
+    withdrawn_policies: Final = frozenset(name for name, outside in outside_by_policy.items() if not outside)
+    withdrawn_guardrails: Final = _pipeline_step_guardrail_names(deferred) - running_elsewhere
+    _, bucket = get_or_create_metadata_bucket(data)
+    _without_names(bucket, "applied_policies", withdrawn_policies)
+    _without_names(bucket, "applied_guardrails", withdrawn_guardrails)
+    sources: Final = bucket.get("policy_sources")
+    if not isinstance(sources, dict):
+        return
+    remaining_sources: Final = {  # mutable-ok: policy_sources stays a dict, the shape its writer updates in place
+        name: reason for name, reason in sources.items() if name not in withdrawn_policies
+    }
+    if remaining_sources:
+        bucket["policy_sources"] = remaining_sources
+    else:
+        bucket.pop("policy_sources")
+
+
+def _defer_post_call_pipelines(
+    data: dict[str, object],  # mutable-ok: same request-payload shape as post_call_success_hook's data
+    response: ResponsesAPIResponse,
+) -> None:
+    deferred: Final = _post_call_pipelines(data)
+    if not deferred:
+        return
+    verbose_proxy_logger.debug(
+        "Post_call guardrail pipelines wait for background response %s (status=%s) to be retrieved complete: %s",
+        response.id,
+        response.status,
+        ", ".join(policy_name for policy_name, _pipeline in deferred),
+    )
+    tag_matched: Final = _tag_matched_deferrals(data, deferred)
+    if tag_matched:
+        verbose_proxy_logger.warning(
+            "Policy engine: background response %s matched post_call policies through a request tag at submit; "
+            "retrieval re-matches only the key, team, and model scopes, so a tag carried in the request body "
+            "does not govern the completed response: %s",
+            response.id,
+            ", ".join(tag_matched),
+        )
+    body_selected: Final = _body_selected_deferrals(data, deferred)
+    if body_selected:
+        verbose_proxy_logger.warning(
+            "Policy engine: background response %s matched post_call policies through the request body's policies "
+            "list at submit; retrieval carries no request body, so those policies do not govern the completed "
+            "response: %s",
+            response.id,
+            ", ".join(body_selected),
+        )
+    _withdraw_deferred_claims(data, deferred)
+
+
+def _tag_matched_deferrals(
+    data: Mapping[str, object], deferred: Sequence[tuple[str, "GuardrailPipeline"]]
+) -> tuple[str, ...]:
+    sources: Final = _policy_state_metadata(data).get("policy_sources")
+    if not isinstance(sources, dict):
+        return ()
+    return tuple(
+        policy_name
+        for policy_name, _pipeline in deferred
+        if policy_name in sources and "tag:" in str(sources[policy_name])
+    )
+
+
+def _body_selected_deferrals(
+    data: Mapping[str, object], deferred: Sequence[tuple[str, "GuardrailPipeline"]]
+) -> tuple[str, ...]:
+    sources: Final = _policy_state_metadata(data).get("policy_sources")
+    attributed: Final = frozenset(sources) if isinstance(sources, dict) else frozenset()
+    return tuple(policy_name for policy_name, _pipeline in deferred if policy_name not in attributed)
+
+
+def _pipeline_unsupported_streaming_guardrails(
+    pipeline: "GuardrailPipeline", translation: "BaseTranslation | None"
+) -> tuple[str, ...]:
+    return tuple(
         dict.fromkeys(
-            step.guardrail for step in pipeline.steps if not _pipeline_step_supports_unified_streaming(step.guardrail)
+            step.guardrail
+            for step in pipeline.steps
+            if not _pipeline_step_supports_streaming(step.guardrail, translation)
         )
     )
+
+
+def _pipeline_is_streamable(
+    policy_name: str, pipeline: "GuardrailPipeline", translation: "BaseTranslation | None"
+) -> bool:
+    unsupported: Final = _pipeline_unsupported_streaming_guardrails(pipeline, translation)
     if not unsupported:
         return True
     verbose_proxy_logger.warning(
-        "Policy '%s' has post_call pipeline guardrails without the unified apply_guardrail interface, "
-        "which streaming pipelines need; the stream skips the pipeline and its guardrails run on their own: %s",
+        "Policy '%s' has post_call pipeline guardrails a streaming pipeline cannot run on this route yet; they "
+        "need the unified apply_guardrail interface, or a post-call hook without a streaming iterator hook on a "
+        "route whose translation assembles the streamed response. The stream skips the pipeline and its "
+        "guardrails run on their own: %s",
         policy_name,
         ", ".join(unsupported),
     )
     return False
 
 
-def _route_supports_streaming_pipelines(user_api_key_dict: UserAPIKeyAuth) -> bool:
-    return not user_api_key_dict.request_route or resolve_endpoint_translation(user_api_key_dict, None) is not None
+def _streaming_pipeline_translation(user_api_key_dict: UserAPIKeyAuth) -> "BaseTranslation | None":
+    resolved: Final = resolve_endpoint_translation(user_api_key_dict, None)
+    return None if resolved is None else resolved[1]
 
 
-def _stream_gated_guardrail_names(
+def stream_gated_guardrail_names(
     request_data: Mapping[str, object], user_api_key_dict: UserAPIKeyAuth
 ) -> frozenset[str]:
-    if not _route_supports_streaming_pipelines(user_api_key_dict):
+    translation: Final = _streaming_pipeline_translation(user_api_key_dict)
+    if translation is None:
         return frozenset()
     return _pipeline_step_guardrail_names(
         tuple(
             (policy_name, pipeline)
             for policy_name, pipeline in _post_call_pipelines(request_data)
-            if all(_pipeline_step_supports_unified_streaming(step.guardrail) for step in pipeline.steps)
+            if not _pipeline_unsupported_streaming_guardrails(pipeline, translation)
         )
     )
 
@@ -584,16 +729,19 @@ def _streamable_post_call_pipelines(
     The post_call pipelines a streaming response can be gated through.
 
     Streaming pipelines scan the buffered stream through the endpoint guardrail
-    translation of the request route, so every step's guardrail needs the
-    unified apply_guardrail interface and the route needs a translation. A
-    pipeline that cannot be run that way yet is left out and its guardrails
-    run on the stream on their own, the way they did before pipelines ran on
-    streams at all, with a warning naming the pipeline.
+    translation of the request route, so every step's guardrail needs either the
+    unified apply_guardrail interface or, on a route whose translation assembles
+    the streamed response, a post-call hook that is its only streaming path, and
+    the route needs a translation. A pipeline that
+    cannot be run that way yet is left out and its guardrails run on the stream
+    on their own, the way they did before pipelines ran on streams at all, with
+    a warning naming the pipeline.
     """
     post_call_pipelines: Final = _post_call_pipelines(request_data)
     if not post_call_pipelines:
         return ()
-    if not _route_supports_streaming_pipelines(user_api_key_dict):
+    translation: Final = _streaming_pipeline_translation(user_api_key_dict)
+    if translation is None:
         verbose_proxy_logger.warning(
             "Policies with post_call guardrail pipelines cannot scan streaming responses on route %s yet "
             "(no endpoint guardrail translation); the stream skips the pipelines and their guardrails run "
@@ -605,7 +753,7 @@ def _streamable_post_call_pipelines(
     return tuple(
         (policy_name, pipeline)
         for policy_name, pipeline in post_call_pipelines
-        if _pipeline_is_streamable(policy_name, pipeline)
+        if _pipeline_is_streamable(policy_name, pipeline, translation)
     )
 
 
@@ -1985,8 +2133,6 @@ class ProxyLogging:
         )
 
         try:
-            _warn_background_skips_post_call_pipelines(data)
-
             # Execute guardrail pipelines before the normal callback loop
             data, _ = await self._maybe_execute_pipelines(  # rebind-ok: pipeline edits feed the callback loop below
                 data=data,
@@ -1997,7 +2143,7 @@ class ProxyLogging:
             )
 
             # Get pipeline-managed guardrails to skip in normal loop
-            pipeline_managed: Final = _pipeline_managed_guardrail_names(data, "pre_call")
+            pipeline_managed: Final = pipeline_managed_guardrail_names(data, "pre_call")
 
             caps: Final = ProxyLogging._callback_capabilities()
             # Skip the per-request callback walk entirely when nothing in
@@ -2762,7 +2908,7 @@ class ProxyLogging:
                 original_exception=original_exception,
             )
 
-        request_data.update(_failure_fields_to_lift(request_data))
+        request_data.update(await offload_token_count(_failure_fields_to_lift)(request_data))
 
         # Remove before callbacks iterate — not serialisable
         request_data.pop("litellm_logging_obj", None)
@@ -2956,6 +3102,24 @@ class ProxyLogging:
             daemon=True,
         ).start()
 
+    async def _run_post_call_pipelines(
+        self,
+        data: dict[str, object],  # mutable-ok: same request-payload shape as post_call_success_hook's data
+        user_api_key_dict: UserAPIKeyAuth,
+        response: LLMResponseTypes,
+    ) -> LLMResponseTypes | None:
+        if _is_pending_background_response(response):
+            _defer_post_call_pipelines(data, response)
+            return None
+        _, pipeline_response = await self._maybe_execute_pipelines(
+            data=data,
+            user_api_key_dict=user_api_key_dict,
+            call_type=getattr(data.get("litellm_logging_obj"), "call_type", None) or "acompletion",
+            event_hook="post_call",
+            response=response,
+        )
+        return pipeline_response
+
     async def post_call_success_hook(
         self,
         data: dict,
@@ -2975,17 +3139,15 @@ class ProxyLogging:
         from litellm.proxy.proxy_server import llm_router
         from litellm.types.guardrails import GuardrailEventHooks
 
-        _, pipeline_response = await self._maybe_execute_pipelines(
+        pipeline_response: Final = await self._run_post_call_pipelines(
             data=data,
             user_api_key_dict=user_api_key_dict,
-            call_type=getattr(data.get("litellm_logging_obj"), "call_type", None) or "acompletion",
-            event_hook="post_call",
             response=response,
         )
         if pipeline_response is not None:
             response = pipeline_response  # rebind-ok: adopt the pipeline's replacement response, same contract as the callback loops below
 
-        pipeline_managed: Final = _pipeline_managed_guardrail_names(data, "post_call")
+        pipeline_managed: Final = pipeline_managed_guardrail_names(data, "post_call")
         guardrail_callbacks, other_callbacks = _partition_post_call_callbacks()
         try:
             # Merge model-level guardrails before checking which guardrails to run
@@ -3301,7 +3463,7 @@ class ProxyLogging:
             _cached_guardrail_data: dict | None = None
             _guardrail_data_computed = False
             pipeline_gated: Final = (
-                _stream_gated_guardrail_names(data, user_api_key_dict) if caps.has_guardrail else frozenset()
+                stream_gated_guardrail_names(data, user_api_key_dict) if caps.has_guardrail else frozenset()
             )
 
             for callback in litellm.callbacks:
@@ -3436,12 +3598,16 @@ class ProxyLogging:
                     ),
                 )
 
-        if post_call_pipelines:
+        pipeline_translation: Final = (
+            resolve_endpoint_translation(user_api_key_dict, None) if post_call_pipelines else None
+        )
+        if pipeline_translation is not None:
             current_response = self._pipeline_gated_stream(
                 response=current_response,
                 user_api_key_dict=user_api_key_dict,
                 request_data=request_data,
                 pipelines=post_call_pipelines,
+                translation=pipeline_translation,
             )
 
         try:
@@ -3465,6 +3631,7 @@ class ProxyLogging:
         user_api_key_dict: UserAPIKeyAuth,
         request_data: dict,  # mutable-ok: same request-payload shape the hooks mutate
         pipelines: "tuple[tuple[str, GuardrailPipeline], ...]",
+        translation: "tuple[str, BaseTranslation]",
     ) -> "AsyncGenerator[Any, None]":
         """
         Execute post_call policy pipelines against a streamed response.
@@ -3474,14 +3641,13 @@ class ProxyLogging:
         assembled output through the endpoint guardrail translation, the same
         machinery flat post_call guardrails use at end of stream. An allow
         releases the buffered chunks: verbatim when no guardrail rewrote the
-        output, rewritten in place when one rewrote text and the translation
-        delivers ended-stream rewrites (later steps then re-scan the rewritten
-        chunks, so rewrites chain). A rewrite the translation cannot deliver
-        yet (a tool-call rewrite, or a text rewrite on a route without
-        write-back) is discarded by the executor and the original chunks are
-        released, as is a buffered shape no translation resolves; a block or
-        modify_response terminates with the translation's block chunks or the
-        raised error.
+        output, rewritten in place when one rewrote text or a tool call and the
+        translation delivers ended-stream rewrites (later steps then re-scan the
+        rewritten chunks, so rewrites chain). A rewrite the translation cannot
+        deliver yet (one on a route without write-back, or a shape the route
+        refuses) is discarded by the executor and the original chunks are
+        released; a block or modify_response terminates with the translation's
+        block chunks or the raised error.
         """
         buffered: Final[list[object]] = []  # mutable-ok: accumulates the stream before the pipeline verdict
         async for item in response:
@@ -3489,17 +3655,7 @@ class ProxyLogging:
         if not buffered:
             return
 
-        resolved: Final = resolve_endpoint_translation(user_api_key_dict, buffered[0])
-        if resolved is None:
-            verbose_proxy_logger.warning(
-                "Policies with post_call guardrail pipelines cannot scan this streaming response shape yet; "
-                "the stream is released ungoverned by them: %s",
-                ", ".join(policy_name for policy_name, _pipeline in pipelines),
-            )
-            for buffered_item in buffered:
-                yield buffered_item
-            return
-        call_type, endpoint_translation = resolved
+        call_type, endpoint_translation = translation
 
         for policy_name, pipeline in pipelines:
             result: PipelineExecutionResult = await PipelineExecutor.execute_steps(
@@ -3753,6 +3909,11 @@ async def prefetch_config_params(prisma_client: "PrismaClient | None", param_nam
         )
 
 
+_WRITER_WRITABILITY_PROBE_SQL: Final = "SELECT current_setting('transaction_read_only') AS transaction_read_only"
+_WRITER_WRITABILITY_PROBE_ROWS: Final = TypeAdapter(list[dict[str, object]])
+_READ_ONLY_RECREATE_BACKOFF_CAP_SECONDS: Final = 600
+
+
 class _ForcedRecreateDeclined(Exception):
     """A forced recreate was declined by the engine-generation guard.
 
@@ -3847,6 +4008,7 @@ class PrismaClient:
             verbose_proxy_logger.error("Please run 'prisma generate' to generate the Prisma client.")
             raise Exception("Unable to find Prisma binaries. Please run 'prisma generate' first.")
         token_auth: Final = self.token_auth
+        writer_token_auth: Final = None if database_url_is_pooled() else token_auth
         # When read-replica routing is on, tag log lines with [writer]/[reader]
         # so the two wrappers' interleaved token refresh logs can be told apart.
         # Single-DB deployments get an empty prefix (logs unchanged).
@@ -3855,13 +4017,13 @@ class PrismaClient:
         if http_client is not None:
             writer_wrapper = PrismaWrapper(
                 original_prisma=Prisma(http=http_client),
-                token_auth=token_auth,
+                token_auth=writer_token_auth,
                 log_prefix=writer_log_prefix,
             )
         else:
             writer_wrapper = PrismaWrapper(
                 original_prisma=Prisma(),
-                token_auth=token_auth,
+                token_auth=writer_token_auth,
                 log_prefix=writer_log_prefix,
             )
 
@@ -3930,6 +4092,8 @@ class PrismaClient:
         self._db_health_watchdog_task: asyncio.Task | None = None
         self._db_last_reconnect_attempt_ts: float = 0.0
         self._db_reconnect_cooldown_seconds: int = max(1, int(os.getenv("PRISMA_RECONNECT_COOLDOWN_SECONDS", "15")))
+        self._db_read_only_recreate_ts: float = 0.0
+        self._db_read_only_recreate_streak: int = 0
         self._db_health_watchdog_interval_seconds: int = max(
             5, int(os.getenv("PRISMA_HEALTH_WATCHDOG_INTERVAL_SECONDS", "30"))
         )
@@ -5647,15 +5811,20 @@ class PrismaClient:
                 writer: Final = self.writer_db
                 if force_recreate is False:
                     try:
-                        await writer.query_raw("SELECT 1")
-                        verbose_proxy_logger.info(
-                            "Writer healthy on probe; skipping recreate (engine "
-                            "likely already replaced by a token refresh)."
-                        )
-                        if isinstance(self.db, RoutingPrismaWrapper):
-                            self.db.mark_writer_recovered()
-                        await self._start_engine_watcher()
-                        return
+                        if await self._writer_is_read_only(writer):
+                            verbose_proxy_logger.warning(
+                                "Writer answers the probe but its session is read-only "
+                                "(writes fail with SQLSTATE 25006); recreating Prisma client."
+                            )
+                        else:
+                            verbose_proxy_logger.info(
+                                "Writer healthy on probe; skipping recreate (engine "
+                                "likely already replaced by a token refresh)."
+                            )
+                            if isinstance(self.db, RoutingPrismaWrapper):
+                                self.db.mark_writer_recovered()
+                            await self._start_engine_watcher()
+                            return
                     except Exception as probe_err:
                         verbose_proxy_logger.warning(
                             "Writer probe failed (%s); recreating Prisma client.",
@@ -5975,6 +6144,18 @@ class PrismaClient:
                         reason="db_health_watchdog_writer_unavailable",
                         timeout_seconds=self._db_watchdog_reconnect_timeout_seconds,
                     )
+                    continue
+                if await asyncio.wait_for(
+                    self._writer_is_read_only(self.writer_db),
+                    timeout=self._db_health_watchdog_probe_timeout_seconds,
+                ):
+                    await self.recreate_read_only_writer(
+                        reason="db_health_watchdog_writer_read_only",
+                        timeout_seconds=self._db_watchdog_reconnect_timeout_seconds,
+                    )
+                    continue
+                self._db_read_only_recreate_streak = 0
+                self._db_read_only_recreate_ts = 0.0
             except asyncio.CancelledError:
                 break
             except Exception as e:
@@ -5986,6 +6167,39 @@ class PrismaClient:
                 else:
                     verbose_proxy_logger.debug("Prisma DB health watchdog observed non-DB error: %s", e)
 
+    async def recreate_read_only_writer(self, reason: str, timeout_seconds: float | None = None) -> bool:
+        """Force-recreate the client behind a writer session that rejects writes
+        (SQLSTATE 25006). Each recreate doubles the wait before the next one
+        until the watchdog sees a writable session again, so a database that is
+        read-only as a whole (replica, failover in progress) does not get its
+        engine killed on every watchdog cycle or failed write."""
+        backoff_seconds: Final = min(
+            self._db_reconnect_cooldown_seconds * 2 ** min(self._db_read_only_recreate_streak, 10),
+            _READ_ONLY_RECREATE_BACKOFF_CAP_SECONDS,
+        )
+        if time.time() - self._db_read_only_recreate_ts < backoff_seconds:
+            verbose_proxy_logger.debug(
+                "Writer session still read-only after %s recreate(s); backing off %ss. reason=%s",
+                self._db_read_only_recreate_streak,
+                backoff_seconds,
+                reason,
+            )
+            return False
+        verbose_proxy_logger.warning(
+            "Writer session is read-only (writes fail with SQLSTATE 25006); recreating Prisma client. reason=%s",
+            reason,
+        )
+        self._db_read_only_recreate_ts = time.time()
+        self._db_read_only_recreate_streak += 1
+        return await self.attempt_db_reconnect(reason=reason, timeout_seconds=timeout_seconds, force_recreate=True)
+
+    async def _writer_is_read_only(self, writer: PrismaWrapper) -> bool:
+        """True iff the pooled writer session answers reads but rejects writes (SQLSTATE 25006)."""
+        rows: Final = _WRITER_WRITABILITY_PROBE_ROWS.validate_python(
+            await writer.query_raw(_WRITER_WRITABILITY_PROBE_SQL)
+        )
+        return any(row.get("transaction_read_only") == "on" for row in rows)
+
     def _probe_target_wrapper(self) -> PrismaWrapper:
         """The Prisma wrapper a `SELECT 1` health probe actually reaches.
 
@@ -6255,48 +6469,13 @@ class PrismaClient:
             verbose_proxy_logger.error("Error getting health check history: %s", e)
             return []
 
-    async def get_all_latest_health_checks(self) -> "Sequence[prisma_models.LiteLLM_HealthCheckTable]":
-        """
-        Get the latest health check for each model.
+    async def get_all_latest_health_checks(self) -> tuple[LatestHealthCheckRow, ...]:
+        """Latest health check per (model_id, model_name), deduplicated in Postgres."""
+        return await fetch_latest_health_checks(self)
 
-        Uses DB-level DISTINCT ON (model_id, model_name) with ORDER BY checked_at DESC
-        (via Prisma ``distinct`` + ``order``) so we never load the full history into memory.
-        """
-        try:
-            return await HealthCheckRepository(self).table.find_many(
-                distinct=["model_id", "model_name"],
-                order=[
-                    {"model_id": "asc"},
-                    {"model_name": "asc"},
-                    {"checked_at": "desc"},
-                ],
-            )
-        except Exception as e:
-            verbose_proxy_logger.error("Error getting all latest health checks: %s", e)
-            return []
-
-    async def get_latest_health_checks_for_models(
-        self, model_names: "Sequence[str]"
-    ) -> "Sequence[prisma_models.LiteLLM_HealthCheckTable]":
-        """
-        Get the latest health check for each of the named models.
-
-        Same DISTINCT ON as ``get_all_latest_health_checks``, bounded to the models asked
-        about, so a paged caller reads health for its page instead of for the whole table.
-        """
-        if not model_names:
-            return ()
-        latest_first: Final = (("model_id", "asc"), ("model_name", "asc"), ("checked_at", "desc"))
-        order: Final = [{field: direction} for field, direction in latest_first]  # mutable-ok: prisma order is a list
-        try:
-            return await HealthCheckRepository(self).table.find_many(
-                where={"model_name": {"in": list(model_names)}},  # mutable-ok: prisma filters are dicts and lists
-                distinct=["model_id", "model_name"],  # mutable-ok: prisma distinct takes a list
-                order=order,
-            )
-        except Exception as e:  # noqa: BLE001  # health decorates a list; a driver error must not fail the page
-            verbose_proxy_logger.error("Error getting latest health checks for models: %s", e)
-            return ()
+    async def get_latest_health_checks_for_models(self, model_names: Sequence[str]) -> tuple[LatestHealthCheckRow, ...]:
+        """Same as ``get_all_latest_health_checks``, bounded to the named models."""
+        return await fetch_latest_health_checks_for_models(self, model_names)
 
 
 ### HELPER FUNCTIONS ###
@@ -7398,6 +7577,12 @@ def _get_openapi_url() -> str | None:
     return "/openapi.json"
 
 
+def _recreate_writer_on_read_only_transaction(prisma_client: "PrismaClient | None") -> None:
+    if prisma_client is None:
+        return
+    asyncio.create_task(prisma_client.recreate_read_only_writer(reason="postgres_read_only_transaction"))
+
+
 def handle_exception_on_proxy(e: Exception) -> ProxyException:
     """
     Returns an Exception as ProxyException, this ensures all exceptions are OpenAI API compatible
@@ -7405,6 +7590,10 @@ def handle_exception_on_proxy(e: Exception) -> ProxyException:
     from fastapi import status
 
     verbose_proxy_logger.exception("Exception: %s", e)
+    if PrismaDBExceptionHandler.is_read_only_transaction_error(e):
+        from litellm.proxy.proxy_server import prisma_client
+
+        _recreate_writer_on_read_only_transaction(prisma_client)
 
     if isinstance(e, HTTPException):
         return ProxyException(
@@ -7806,6 +7995,88 @@ async def get_available_models_for_user(
     return all_models
 
 
+def _safe_get_model_info(model: str, get_model_info: Callable[[str], ModelInfo]) -> ModelInfo | None:
+    try:
+        return get_model_info(model)
+    except Exception as e:
+        verbose_proxy_logger.debug(
+            "create_model_info_response: cost map lookup failed for %s: %s",
+            model,
+            e,
+        )
+        return None
+
+
+def _resolve_listing_model_info(
+    deployment_model: str | None,
+    listed_model: str,
+    listed_info: ModelInfo | None,
+    get_model_info: Callable[[str], ModelInfo],
+) -> tuple[ModelInfo, ...]:
+    """
+    Cost-map entries describing one deployment behind a listed model, best source first.
+
+    The name a model is listed under is an arbitrary public alias, so it often misses the
+    cost map and lands on a fallback-generalization rule that answers with a conservative
+    family baseline instead of the real model's limits; the deployment's underlying model
+    is what the request actually reaches. Both names are kept because either can
+    generalize, and because a deployment's own model is registered into the cost map as a
+    stub that carries no limits of its own. Exact entries are consulted before generalized
+    ones, and each field is then taken from the first entry that has it.
+
+    ``listed_info`` is resolved once by the caller, since a group with several distinct
+    underlying models resolves the same alias for each of them.
+    """
+    # Fast path, and the only one a wildcard-expanded name takes: with a single name
+    # there is nothing to order, so skip the generalization test entirely. This keeps
+    # the per-model cost of the listing on the hot path #33721 exists to protect.
+    if deployment_model is None or deployment_model == listed_model:
+        return () if listed_info is None else (listed_info,)
+
+    deployment_info: Final = _safe_get_model_info(deployment_model, get_model_info)
+    if deployment_info is None:
+        return () if listed_info is None else (listed_info,)
+    if listed_info is None:
+        return (deployment_info,)
+
+    from litellm.utils import is_generalized_model_info
+
+    # Both names resolved: the deployment's model leads unless it only generalized
+    # while the listed name is an exact cost-map entry.
+    if is_generalized_model_info(deployment_info) and not is_generalized_model_info(listed_info):
+        return (listed_info, deployment_info)
+    return (deployment_info, listed_info)
+
+
+def _first_token_limit(candidates: tuple[ModelInfo, ...], field: str) -> int | None:
+    return next(
+        (limit for limit in (coerce_token_limit(info.get(field)) for info in candidates) if limit is not None),
+        None,
+    )
+
+
+def _group_token_limit(candidate_sets: tuple[tuple[ModelInfo, ...], ...], field: str) -> int | None:
+    """The widest limit any deployment behind the listed name declares for ``field``.
+
+    A model group is normally one model behind several interchangeable deployments, so
+    there is a single value to report and the choice of aggregate does not arise.
+
+    When a group genuinely mixes models no single number is right, and the widest is the
+    deliberate pick over the narrowest for two reasons. It is what ``/model_group/info``
+    has long reported to the Admin UI, so the two surfaces agree; disagreeing is the very
+    complaint this resolution path exists to fix. And of the two ways to be wrong,
+    under-advertising is worse: a client that trusts a narrowed window silently refuses
+    prompts the group would have served, while an over-long prompt that reaches a smaller
+    deployment comes back as a legible context-length error -- and does not reach one at
+    all when ``enable_pre_call_checks`` is set, which filters deployments the prompt does
+    not fit.
+    """
+    limits: Final = tuple(
+        limit for limit in (_first_token_limit(candidates, field) for candidates in candidate_sets) if limit is not None
+    )
+    return max(limits) if limits else None
+
+
 def create_model_info_response(
     model_id: str,
     provider: str,
@@ -7830,31 +8101,48 @@ def create_model_info_response(
         "owned_by": provider,
     }
 
-    try:
-        model_cost_info: ModelInfo | None = get_model_info(model_id)
-    except Exception as e:
-        verbose_proxy_logger.debug(
-            "create_model_info_response: cost map lookup failed for %s: %s",
-            model_id,
-            e,
-        )
-        model_cost_info = None
+    listing_info: Final = llm_router.get_model_listing_info(model_id) if llm_router is not None else None
 
-    max_input_tokens: int | None = None
-    max_output_tokens: int | None = None
-    if model_cost_info is not None:
-        max_input_tokens = coerce_token_limit(model_cost_info.get("max_input_tokens"))
-        max_output_tokens = coerce_token_limit(model_cost_info.get("max_output_tokens"))
-        mode: Final = model_cost_info.get("mode")
-        if isinstance(mode, str):
-            base["mode"] = mode
+    # One entry per distinct model behind the listed name; (None,) when the router knows
+    # nothing about it, so the listed name is resolved on its own as before.
+    deployment_models: Final[tuple[str | None, ...]] = (
+        listing_info.cost_map_keys if listing_info is not None and listing_info.cost_map_keys else (None,)
+    )
+    listed_info: Final = _safe_get_model_info(model_id, get_model_info)
+    candidate_sets: Final = tuple(
+        _resolve_listing_model_info(
+            deployment_model=deployment_model,
+            listed_model=model_id,
+            listed_info=listed_info,
+            get_model_info=get_model_info,
+        )
+        for deployment_model in deployment_models
+    )
+
+    max_input_tokens: int | None = _group_token_limit(candidate_sets, "max_input_tokens")
+    max_output_tokens: int | None = _group_token_limit(candidate_sets, "max_output_tokens")
+    mode: Final = next(
+        (
+            m
+            for m in (
+                cast("Mapping[str, object]", info).get("mode")  # cast-ok: an entry need not carry "mode"
+                for candidates in candidate_sets
+                for info in candidates
+            )
+            if isinstance(m, str)
+        ),
+        None,
+    )
+    if mode is not None:
+        base["mode"] = mode
+
+    if listing_info is not None:
+        if listing_info.max_input_tokens is not None:
+            max_input_tokens = listing_info.max_input_tokens
+        if listing_info.max_output_tokens is not None:
+            max_output_tokens = listing_info.max_output_tokens
 
     if llm_router is not None:
-        configured_input, configured_output = llm_router.get_configured_token_limits(model_id)
-        if configured_input is not None:
-            max_input_tokens = configured_input
-        if configured_output is not None:
-            max_output_tokens = configured_output
         configured_mode: Final = llm_router.get_configured_mode(model_id)
         if isinstance(configured_mode, str):
             base["mode"] = configured_mode
diff --git a/litellm/repositories/object_permission_repository.py b/litellm/repositories/object_permission_repository.py
index 6b1f9c68e47..7736939c696 100644
--- a/litellm/repositories/object_permission_repository.py
+++ b/litellm/repositories/object_permission_repository.py
@@ -40,6 +40,7 @@ class ObjectPermissionRepository(BaseRepository[LiteLLM_ObjectPermissionTable]):
         blocked_tools: list[str] | None = None,
         mcp_toolsets: list[str] | None = None,
         search_tools: list[str] | None = None,
+        skills: list[str] | None = None,
     ) -> LiteLLM_ObjectPermissionTable:
         """Create a new object permission record."""
         data: Final[dict[str, Any]] = {}
@@ -63,6 +64,8 @@ class ObjectPermissionRepository(BaseRepository[LiteLLM_ObjectPermissionTable]):
             data["mcp_toolsets"] = mcp_toolsets
         if search_tools is not None:
             data["search_tools"] = search_tools
+        if skills is not None:
+            data["skills"] = skills
 
         return await self.create(data)
 
@@ -79,6 +82,7 @@ class ObjectPermissionRepository(BaseRepository[LiteLLM_ObjectPermissionTable]):
         blocked_tools: list[str] | None = None,
         mcp_toolsets: list[str] | None = None,
         search_tools: list[str] | None = None,
+        skills: list[str] | None = None,
     ) -> LiteLLM_ObjectPermissionTable | None:
         """Update an object permission record."""
         data: Final[dict[str, Any]] = {}
@@ -102,6 +106,8 @@ class ObjectPermissionRepository(BaseRepository[LiteLLM_ObjectPermissionTable]):
             data["mcp_toolsets"] = mcp_toolsets
         if search_tools is not None:
             data["search_tools"] = search_tools
+        if skills is not None:
+            data["skills"] = skills
 
         return await self.update(object_permission_id, data, id_field="object_permission_id")
 
diff --git a/litellm/responses/litellm_completion_transformation/streaming_iterator.py b/litellm/responses/litellm_completion_transformation/streaming_iterator.py
index d7f8cd8f8bd..660dd8f0c92 100644
--- a/litellm/responses/litellm_completion_transformation/streaming_iterator.py
+++ b/litellm/responses/litellm_completion_transformation/streaming_iterator.py
@@ -437,14 +437,11 @@ class LiteLLMCompletionStreamingIterator(ResponsesAPIStreamingIterator):
             response_created_event_data["temperature"] = self.responses_api_request["temperature"]
         if "text" in self.responses_api_request:
             response_created_event_data["text"] = self.responses_api_request["text"]
-        if "tool_choice" in self.responses_api_request:
-            # Transform tool_choice from dict format (e.g., {"type": "auto"}) to string format
-            response_created_event_data["tool_choice"] = (
-                LiteLLMCompletionResponsesConfig._transform_tool_choice(self.responses_api_request["tool_choice"])
-                or "auto"
+        response_created_event_data["tool_choice"] = (
+            LiteLLMCompletionResponsesConfig._transform_tool_choice_for_responses_api_response(
+                self.responses_api_request.get("tool_choice")
             )
-        else:
-            response_created_event_data["tool_choice"] = "auto"
+        )
         if "tools" in self.responses_api_request:
             response_created_event_data["tools"] = self.responses_api_request["tools"]
         else:
diff --git a/litellm/responses/litellm_completion_transformation/transformation.py b/litellm/responses/litellm_completion_transformation/transformation.py
index b2d1a69e0d8..fca5b0d11cf 100644
--- a/litellm/responses/litellm_completion_transformation/transformation.py
+++ b/litellm/responses/litellm_completion_transformation/transformation.py
@@ -27,8 +27,10 @@ from openai.types.chat.chat_completion_named_tool_choice_param import (
 )
 from openai.types.responses import ResponseFunctionToolCall
 from openai.types.responses.response_create_params import ResponseInputParam
+from openai.types.responses.tool_choice_custom_param import ToolChoiceCustomParam
+from openai.types.responses.tool_choice_function_param import ToolChoiceFunctionParam
 from openai.types.responses.tool_param import FunctionToolParam
-from pydantic import TypeAdapter
+from pydantic import TypeAdapter, ValidationError
 from typing_extensions import ReadOnly, TypedDict
 
 from litellm._logging import verbose_logger
@@ -68,6 +70,7 @@ from litellm.types.llms.openai import (
     ResponsesAPIOptionalRequestParams,
     ResponsesAPIResponse,
     ResponsesAPIStatus,
+    ToolChoice,
     ValidChatCompletionMessageContentTypes,
     ValidChatCompletionMessageContentTypesLiteral,
 )
@@ -126,6 +129,7 @@ _STR_KEY_DICT_ADAPTER: Final = TypeAdapter(dict[str, object])
 _OBJECT_LIST_ADAPTER: Final = TypeAdapter(list[object])
 _DICT_ITEMS_LIST_ADAPTER: Final = TypeAdapter(list[dict[object, object]])
 _TEXT_ADAPTER: Final = TypeAdapter(str)
+_RESPONSES_API_TOOL_CHOICE_ADAPTER: Final = TypeAdapter(ToolChoice)
 
 
 @runtime_checkable
@@ -267,6 +271,27 @@ class LiteLLMCompletionResponsesConfig:
         # Return as-is for unknown formats
         return tool_choice
 
+    @staticmethod
+    def _transform_tool_choice_for_responses_api_response(tool_choice: object) -> ToolChoice:
+        if tool_choice is None:
+            return "auto"
+        try:
+            return _RESPONSES_API_TOOL_CHOICE_ADAPTER.validate_python(tool_choice)
+        except ValidationError:
+            return LiteLLMCompletionResponsesConfig._chat_tool_choice_as_responses_api_tool_choice(tool_choice)
+
+    @staticmethod
+    def _chat_tool_choice_as_responses_api_tool_choice(tool_choice: object) -> ToolChoice:
+        match tool_choice, LiteLLMCompletionResponsesConfig._transform_tool_choice(tool_choice):
+            case {"type": "custom"}, {"function": {"name": str(custom_name)}}:
+                return ToolChoiceCustomParam(type="custom", name=custom_name)
+            case _, {"type": "function", "function": {"name": str(function_name)}}:
+                return ToolChoiceFunctionParam(type="function", name=function_name)
+            case _, "none" | "auto" | "required" as normalized:
+                return normalized
+            case _, _:
+                return "auto"
+
     @staticmethod
     def _should_drop_derived_web_search_options(model: str, custom_llm_provider: str | None) -> bool:
         """
@@ -2263,7 +2288,9 @@ class LiteLLMCompletionResponsesConfig:
             ),
             parallel_tool_calls=getattr(chat_completion_response, "parallel_tool_calls", False),
             temperature=getattr(chat_completion_response, "temperature", 0),
-            tool_choice=getattr(chat_completion_response, "tool_choice", "auto"),
+            tool_choice=LiteLLMCompletionResponsesConfig._transform_tool_choice_for_responses_api_response(
+                responses_api_request.get("tool_choice")
+            ),
             tools=getattr(chat_completion_response, "tools", []),
             top_p=getattr(chat_completion_response, "top_p", None),
             max_output_tokens=getattr(chat_completion_response, "max_output_tokens", None),
diff --git a/litellm/responses/main.py b/litellm/responses/main.py
index 7a210cdd970..a68cd02e61b 100644
--- a/litellm/responses/main.py
+++ b/litellm/responses/main.py
@@ -4,10 +4,11 @@ from collections.abc import Coroutine, Generator, Iterable, Mapping
 from contextlib import contextmanager
 from dataclasses import dataclass
 from functools import partial
-from typing import TYPE_CHECKING, Any, Final, Literal, Optional, cast
+from typing import TYPE_CHECKING, Any, Final, Literal, NoReturn, Optional, TypeAlias, cast
 
 import httpx
 from pydantic import BaseModel
+from typing_extensions import assert_never
 
 import litellm
 from litellm._logging import verbose_logger
@@ -407,6 +408,37 @@ def _bridges_to_chat_completions(
     return responses_api_provider_config is None or use_chat_completions_api is True
 
 
+_ResponsesCompatibilityFailure: TypeAlias = Literal["encrypted_task_unsupported"]
+
+
+def _encrypted_task_support_failure(
+    responses_api_provider_config: BaseResponsesAPIConfig | None, use_chat_completions_api: bool
+) -> _ResponsesCompatibilityFailure | None:
+    if (
+        responses_api_provider_config is None
+        or _bridges_to_chat_completions(responses_api_provider_config, use_chat_completions_api)
+        or not responses_api_provider_config.supports_encrypted_agent_messages()
+    ):
+        return "encrypted_task_unsupported"
+    return None
+
+
+def _raise_responses_compatibility_failure(
+    failure: _ResponsesCompatibilityFailure, model: str, custom_llm_provider: str | None
+) -> NoReturn:
+    match failure:
+        case "encrypted_task_unsupported":
+            raise litellm.exception_type(
+                model=model,
+                custom_llm_provider=custom_llm_provider,
+                original_exception=ValueError(
+                    "Encrypted task classification requires a compatible native Responses deployment"
+                ),
+            )
+        case _:
+            assert_never(failure)
+
+
 def _deployment_passes_through_responses(model_info: object) -> bool:
     """Whether ``model_info.supported_endpoints`` opts the deployment into native ``{api_base}/responses``."""
     if not isinstance(model_info, dict):
@@ -1078,6 +1110,7 @@ def responses(
         litellm_call_id: Final[str | None] = kwargs.get("litellm_call_id", None)
         _is_async: Final = kwargs.pop("aresponses", False) is True
         skip_mcp_handler: Final = kwargs.pop("_skip_mcp_handler", False)
+        require_encrypted_task_support: Final = kwargs.pop("_require_encrypted_task_support", False) is True
         use_chat_completions_api = _pop_use_chat_completions_api_kw(kwargs)
 
         client_headers: Final = kwargs.get("headers")
@@ -1186,6 +1219,17 @@ def responses(
                 model, custom_llm_provider, deployment_model_info
             )
 
+        if (
+            require_encrypted_task_support
+            and (
+                compatibility_failure := _encrypted_task_support_failure(
+                    responses_api_provider_config, use_chat_completions_api
+                )
+            )
+            is not None
+        ):
+            _raise_responses_compatibility_failure(compatibility_failure, model, custom_llm_provider)
+
         local_vars.update(kwargs)
         # Map reasoning_effort (from litellm_params/proxy config) to reasoning when not set
         if reasoning is None and "reasoning_effort" in local_vars:
diff --git a/litellm/responses/streaming_iterator.py b/litellm/responses/streaming_iterator.py
index 9f9016c5a7f..40ff88fc557 100644
--- a/litellm/responses/streaming_iterator.py
+++ b/litellm/responses/streaming_iterator.py
@@ -13,6 +13,7 @@ from typing import TYPE_CHECKING, Any, Final, Literal, Protocol, overload, runti
 
 import httpx
 from openai._streaming import SSEDecoder
+from pydantic import BaseModel, ValidationError
 from typing_extensions import TypeIs
 
 import litellm
@@ -438,18 +439,7 @@ class BaseResponsesAPIStreamingIterator:
         if self._persist_completed_response_before_logging:
             self._persist_completed_response_to_cache(is_async=is_async)
 
-        # Create a copy for logging to avoid modifying the response object that will be returned to the user
-        # The logging handlers may transform usage from Responses API format (input_tokens/output_tokens)
-        # to chat completion format (prompt_tokens/completion_tokens) for internal logging
-        # Use model_dump + model_validate instead of deepcopy to avoid pickle errors with
-        # Pydantic ValidatorIterator when response contains tool_choice with allowed_tools (fixes #17192)
-        logging_response = self.completed_response
-        if self.completed_response is not None and hasattr(self.completed_response, "model_dump"):
-            try:
-                logging_response = type(self.completed_response).model_validate(self.completed_response.model_dump())
-            except Exception:
-                # Fallback to original if serialization fails
-                pass
+        logging_response: Final[object] = _logging_copy(self.completed_response)
         self._restore_provider_response_headers(logging_response)
 
         end_time: Final = datetime.now()
@@ -488,10 +478,10 @@ class BaseResponsesAPIStreamingIterator:
     def _restore_provider_response_headers(self, logging_response: object) -> None:
         """Re-apply the provider's response headers to the copy handed to logging callbacks.
 
-        ``model_validate(model_dump())`` above drops pydantic private attributes, so the
+        ``model_validate(model_dump())`` in ``_logging_copy`` drops pydantic private attributes, so the
         ``_hidden_params`` the provider transform set on the nested response are lost. Returns early
-        when that copy fell back to the original event, so logging-only state never lands on the
-        object the caller is iterating.
+        when the event was not a pydantic model and logging got the original, so logging-only state
+        never lands on the object the caller is iterating.
         """
         if logging_response is self.completed_response:
             return
@@ -544,7 +534,7 @@ class BaseResponsesAPIStreamingIterator:
     def _record_failed_response_usage(self, response_obj: ResponsesAPIResponse | None) -> None:
         if response_obj is None or self.logging_obj is None:
             return
-        usage_obj: Final[ResponseAPIUsage | None] = getattr(response_obj, "usage", None)
+        usage_obj: Final[ResponseAPIUsage | None] = _usage_as_model(getattr(response_obj, "usage", None))
         if usage_obj is None:
             return
         try:
@@ -1293,14 +1283,46 @@ def _add_text_like_part_events(
         )
 
 
+def _logging_copy(event: object) -> object:
+    """Hand logging callbacks a copy, so their usage rewrite (Responses shape to chat shape) never
+    reaches the event the caller is iterating. The round trip through ``model_dump`` sidesteps the
+    deepcopy pickle errors of #17192; when a provider payload fails validation (LIT-7391), shallow
+    copies of the event and its nested response still keep the caller's ``usage`` attribute separate."""
+    if not isinstance(event, BaseModel):
+        return event
+    try:
+        return type(event).model_validate(event.model_dump())
+    except Exception:
+        return _detached_shallow_copy(event)
+
+
+def _detached_shallow_copy(event: BaseModel) -> BaseModel:
+    nested: Final[object] = getattr(event, "response", None)
+    if isinstance(nested, BaseModel):
+        return event.model_copy(update={"response": nested.model_copy()})
+    return event.model_copy()
+
+
+def _usage_as_model(usage: object) -> ResponseAPIUsage | None:
+    if isinstance(usage, ResponseAPIUsage):
+        return usage
+    if not isinstance(usage, dict):
+        return None
+    try:
+        return ResponseAPIUsage.model_validate(usage)
+    except ValidationError:
+        return None
+
+
 def _stamp_responses_usage_cost(
     response_obj: ResponsesAPIResponse | None, logging_obj: LiteLLMLoggingObj | None
 ) -> None:
     if response_obj is None or logging_obj is None:
         return
-    usage_obj: Final[ResponseAPIUsage | None] = getattr(response_obj, "usage", None)
+    usage_obj: Final[ResponseAPIUsage | None] = _usage_as_model(getattr(response_obj, "usage", None))
     if usage_obj is None:
         return
+    response_obj.usage = usage_obj  # rebind-ok: the stamped cost has to ride on the response the client receives
     if isinstance(getattr(usage_obj, "cost", None), (int, float)):
         return
     try:
diff --git a/litellm/responses/utils.py b/litellm/responses/utils.py
index 540d492beec..599e978df6a 100644
--- a/litellm/responses/utils.py
+++ b/litellm/responses/utils.py
@@ -543,6 +543,49 @@ class ResponsesAPIRequestUtils:
 
         return request_input
 
+    @staticmethod
+    def strip_encrypted_reasoning_from_input(request_input: object) -> None:
+        """Drop reasoning items the routed deployment cannot decrypt, keeping their readable summary.
+
+        Mutates ``request_input`` in place: the router's fallback snapshot shares this
+        list object, so a rebound list would replay the stripped items on the fallback hop.
+        """
+        if not isinstance(request_input, list):
+            return
+        items: Final = cast(list[object], request_input)  # cast-ok: untyped client json
+        stripped: Final = tuple(ResponsesAPIRequestUtils._without_encrypted_reasoning(item) for item in items)
+        items[:] = (item for item in stripped if item is not None)  # rebind-ok: list shared with fallback snapshot
+
+    @staticmethod
+    def _without_encrypted_reasoning(item: object) -> object | None:
+        if not isinstance(item, dict):
+            return item
+        reasoning: Final = cast(Mapping[str, object], item)  # cast-ok: untyped client json
+        if reasoning.get("type") != "reasoning" or not reasoning.get("encrypted_content"):
+            return reasoning
+        readable: Final = any(
+            ResponsesAPIRequestUtils._has_readable_text(reasoning.get(key)) for key in ("summary", "content")
+        )
+        if not readable:
+            return None
+        kept: Final[dict[str, object]] = {  # mutable-ok: request item rebuilt without the undecryptable keys
+            key: value for key, value in reasoning.items() if key not in ("encrypted_content", "id")
+        }
+        return kept
+
+    @staticmethod
+    def _has_readable_text(value: object) -> bool:
+        """A reasoning item's ``summary``/``content`` carries readable text: a non-empty string, or a
+        list holding at least one block with a non-empty ``text`` field (summary_text / output_text)."""
+        if isinstance(value, str):
+            return bool(value.strip())
+        if isinstance(value, list):
+            return any(
+                isinstance(block, dict) and bool(cast(Mapping[str, object], block).get("text"))  # cast-ok: untyped json
+                for block in value
+            )
+        return False
+
     @staticmethod
     def _build_responses_api_response_id(
         custom_llm_provider: str | None,
diff --git a/litellm/router.py b/litellm/router.py
index 934a4ac86a9..9e6db66db83 100644
--- a/litellm/router.py
+++ b/litellm/router.py
@@ -53,6 +53,7 @@ from litellm.caching.caching import (
     RedisCache,
     RedisClusterCache,
 )
+from litellm.caching.redis_cache import log_redis_failure
 from litellm.constants import (
     CLIENT_OUTPUT_CEILING_METADATA_KEY,
     CONSUMED_REQUEST_TAGS_METADATA_KEY,
@@ -67,7 +68,7 @@ from litellm.constants import (
     SESSION_DEPLOYMENT_AFFINITY_TTL_METADATA_KEY,
 )
 from litellm.integrations.custom_logger import CustomLogger
-from litellm.litellm_core_utils.asyncify import asyncify, run_async_function
+from litellm.litellm_core_utils.asyncify import run_async_function
 from litellm.litellm_core_utils.core_helpers import (
     _get_parent_otel_span_from_kwargs,
     coerce_token_limit,
@@ -98,6 +99,8 @@ from litellm.litellm_core_utils.sensitive_data_masker import (
     mask_credentials_in_payload,
     mask_sensitive_structure,
 )
+from litellm.litellm_core_utils.token_counter import offload_token_count
+from litellm.llms.base_llm.passthrough.transformation import replace_path_segment
 from litellm.llms.base_llm.vector_store.transformation import (
     RouterVectorStoreEmbeddingExecutor,
     vector_store_request_metadata,
@@ -148,6 +151,8 @@ from litellm.router_utils.common_utils import (
     _is_proxy_admin_request,
     filter_team_based_models,
     filter_web_search_deployments,
+    get_request_team_id,
+    provider_for_generic_call,
     resolve_model_group_alias,
     truncate_fallback_error_detail,
     warn_on_provider_credential_mismatch,
@@ -226,6 +231,7 @@ from litellm.types.router import (
     CredentialLiteLLMParams,
     CustomRoutingStrategyBase,
     Deployment,
+    DeploymentModelListingInfo,
     DeploymentTypedDict,
     FallbackAccessCheck,
     GuardrailTypedDict,
@@ -939,6 +945,9 @@ class Router:
         # ``id()``-reuse risk after GC). See
         # ``litellm.proxy.auth.auth_checks._is_model_cost_zero``.
         self._zero_cost_cache: dict[str, bool] = {}
+        self.cached_deployment_model_info = lru_cache(maxsize=DEFAULT_MAX_LRU_CACHE_SIZE)(
+            self.get_deployment_model_info
+        )
         self._routing_group_rows: tuple[DeploymentTypedDict, ...] | None = None
         self._init_routing_groups(None)
         self._provider_unresolved_deployments: tuple[Callable[[], Deployment | None], ...] = ()
@@ -1317,6 +1326,43 @@ class Router:
         if isinstance(litellm.input_callback, list):
             litellm.input_callback = [c for c in litellm.input_callback if id(c) not in selector_ids]
 
+    def _apply_updated_routing_strategy_args(self) -> None:
+        """
+        Re-link the default group's selector to the current `routing_strategy_args`.
+
+        Selectors freeze their `RoutingArgs` at construction, so a runtime args
+        update would otherwise keep serving the boot-time values until restart.
+        Latency/usage state survives the rebuild: it lives in the shared router
+        cache, not on the selector.
+        """
+        strategy: Final = self._normalize_strategy(self.routing_strategy)
+        if strategy == "lar1":
+            from litellm.router_strategy.lar1_routing import apply_lar1_routing_strategy
+
+            apply_lar1_routing_strategy(self, self.routing_strategy_args)
+            return
+
+        attr: Final = self._DEFAULT_SELECTOR_ATTR_BY_STRATEGY.get(strategy or "")
+        current: Final = getattr(self, attr, None) if attr is not None else None
+        if attr is None or current is None:
+            return
+
+        try:
+            rebuilt: Final = self._build_strategy_selector(
+                strategy=strategy or "",
+                routing_strategy_args=self.routing_strategy_args,
+            )
+        except (TypeError, ValidationError):
+            verbose_router_logger.exception(
+                "Invalid routing_strategy_args %s for '%s'; keeping the previous ones",
+                self.routing_strategy_args,
+                strategy,
+            )
+            return
+
+        self._unregister_router_selectors((current,))
+        setattr(self, attr, rebuilt)
+
     def routing_strategy_init(self, routing_strategy: RoutingStrategy | str, routing_strategy_args: dict):
         verbose_router_logger.info("Routing strategy: %s", routing_strategy)
         self._validate_routing_strategy(routing_strategy)
@@ -5160,7 +5206,7 @@ class Router:
                 # If get_llm_provider fails, fall back to using model_name as-is
                 replacement_model_name = model_name
 
-            kwargs["endpoint"] = kwargs["endpoint"].replace(model, replacement_model_name)
+            kwargs["endpoint"] = replace_path_segment(kwargs["endpoint"], model, replacement_model_name)
         return kwargs
 
     async def _ageneric_api_call_with_fallbacks_helper(self, model: str, original_generic_function: Callable, **kwargs):
@@ -5196,16 +5242,7 @@ class Router:
                 kwargs=kwargs, model=model, model_name=model_name
             )
 
-            # Get custom_llm_provider from deployment params
-            try:
-                custom_llm_provider = data.get("custom_llm_provider")
-                _, inferred_custom_llm_provider, _, _ = get_llm_provider(
-                    model=data["model"],
-                    custom_llm_provider=custom_llm_provider,
-                )
-                custom_llm_provider = custom_llm_provider or inferred_custom_llm_provider
-            except Exception:
-                custom_llm_provider = None
+            custom_llm_provider: Final = provider_for_generic_call(data)
 
             response_kwargs: Final = {
                 **data,
@@ -5716,15 +5753,7 @@ class Router:
             # Perform pre-call checks for routing strategy
             self.routing_strategy_pre_call_checks(deployment=deployment)
 
-            try:
-                custom_llm_provider = data.get("custom_llm_provider")
-                _, inferred_custom_llm_provider, _, _ = get_llm_provider(
-                    model=data["model"],
-                    custom_llm_provider=custom_llm_provider,
-                )
-                custom_llm_provider = custom_llm_provider or inferred_custom_llm_provider
-            except Exception:
-                custom_llm_provider = None
+            custom_llm_provider: Final = provider_for_generic_call(data)
 
             response: Final = original_function(
                 **{
@@ -10018,6 +10047,7 @@ class Router:
                 model=deployment.litellm_params.model,
                 custom_llm_provider=deployment.litellm_params.custom_llm_provider,
             )
+        self._invalidate_model_group_info_cache()
 
     def delete_deployment(self, id: str) -> Deployment | None:
         """
@@ -10186,15 +10216,71 @@ class Router:
             return None
         return Deployment(**first_usable) if isinstance(first_usable, dict) else first_usable
 
+    def get_model_listing_info(self, model_name: str) -> DeploymentModelListingInfo | None:
+        """
+        Return what the concrete deployments behind model_name contribute to its
+        /v1/models entry: the cost-map keys for their underlying models, plus the widest
+        token limits explicitly configured in their model_info. Resolved via O(1) index
+        lookup.
+
+        Returns None for wildcard-expanded or unknown names, where the listed name is the
+        real model name and no deployment-specific information exists, and treats a
+        malformed configured limit as absent rather than failing the listing.
+
+        The whole group is read rather than just its first deployment, so a group that
+        mixes models does not advertise a window that depends on config order; the widest
+        one is reported, which is what get_model_group_info already shows the Admin UI.
+        Keys are deduplicated, so the ordinary group of interchangeable deployments of one
+        model still costs the caller a single cost-map lookup. Unlike get_model_group_info,
+        this never triggers pattern matching or deep copies, so it is safe to call per
+        listed model on the /v1/models hot path.
+        """
+        indices: Final = self.model_name_to_deployment_indices.get(model_name)
+        if not indices:
+            return None
+
+        deployments: Final = tuple(self.model_list[index] for index in indices)
+        model_infos: Final = tuple(deployment.get("model_info") or MappingProxyType({}) for deployment in deployments)
+        params: Final = tuple(deployment.get("litellm_params") or MappingProxyType({}) for deployment in deployments)
+        # base_model resolution mirrors get_router_model_info: unset or blank means the
+        # deployment's own model name is the cost-map key.
+        cost_map_keys: Final = tuple(
+            dict.fromkeys(  # deduplicates while preserving config order
+                key
+                for key in (
+                    model_info.get("base_model") or litellm_params.get("base_model") or litellm_params.get("model")
+                    for model_info, litellm_params in zip(model_infos, params)
+                )
+                if isinstance(key, str) and key
+            )
+        )
+        return DeploymentModelListingInfo(
+            cost_map_keys=cost_map_keys,
+            max_input_tokens=self._widest_configured_limit(model_infos, "max_input_tokens"),
+            max_output_tokens=self._widest_configured_limit(model_infos, "max_output_tokens"),
+        )
+
+    @staticmethod
+    def _widest_configured_limit(model_infos: Sequence[Mapping[str, Any]], field: str) -> int | None:
+        """The largest usable value of ``field`` across a group's configured model_info blocks."""
+        limits: Final = tuple(
+            limit
+            for limit in (coerce_token_limit(model_info.get(field)) for model_info in model_infos)
+            if limit is not None
+        )
+        return max(limits) if limits else None
+
     def get_configured_token_limits(self, model_name: str) -> "tuple[int | None, int | None]":
         """
         Return (max_input_tokens, max_output_tokens) explicitly configured in a concrete
         deployment's model_info for model_name, via O(1) index lookup.
 
         Returns (None, None) for wildcard-expanded or unknown names, and treats a
-        malformed configured value as absent rather than failing the listing. Unlike
-        get_model_group_info, this never triggers pattern matching or deep copies, so it
-        is safe to call per listed model on the /v1/models hot path.
+        malformed configured value as absent rather than failing the caller.
+
+        Deliberately reads one deployment rather than aggregating the group the way
+        get_model_listing_info does: its caller truncates an embedding input to this
+        value, so the widest window in a mixed group would be the wrong answer there.
         """
         deployment: Final = self.get_deployment_by_model_group_name(model_group_name=model_name)
         if deployment is None:
@@ -10979,6 +11065,9 @@ class Router:
         """
         return self.get_model_group_info(model_group)
 
+    def cached_model_group_info(self, model_group: str) -> ModelGroupInfo | None:
+        return self._cached_get_model_group_info(model_group)
+
     async def get_remaining_model_group_usage(self, model_group: str) -> dict[str, int]:
         model_group_info: Final = self._cached_get_model_group_info(model_group)
 
@@ -11130,6 +11219,43 @@ class Router:
 
         return ids
 
+    def get_candidate_model_ids_for_route(self, model: str, team_id: str | None = None) -> frozenset[str]:
+        """
+        Deployment ids that could serve ``model`` for ``team_id``, following the same
+        precedence ``_common_checks_available_deployment`` uses to build a candidate pool:
+        ``model_group_alias``, then a routing group, then the first matching early-resolve
+        path for a name that is not a ``model_name`` (team route, wildcard pattern via
+        ``get_deployments_by_pattern``, team pattern router, default deployment), then the
+        ``model_name`` and team indexes. Delegating to the router's own resolvers keeps this
+        aligned with how a route actually resolves rather than re-deriving it, and unlike
+        ``_common_checks_available_deployment`` it is read-only: it does not apply request
+        fallbacks and (with ``include_team_models`` left off) does not raise. Lets a pre-call
+        check tell a genuine cross-group route from same-group unavailability without leaking
+        deployment ids into request kwargs bound for the provider.
+        """
+        resolved: Final = self._get_model_from_alias(model=model) or model
+        routing_group_members: Final = self._get_routing_group_deployments(model=resolved, team_id=team_id)
+        if routing_group_members is not None:
+            return self._deployment_ids(routing_group_members)
+        early: Final = self._try_early_resolve_deployments_for_model_not_in_names(
+            model=resolved, request_team_id=team_id
+        )
+        if early is not None:
+            early_deployments: Final = early[1]
+            return self._deployment_ids(
+                (early_deployments,) if isinstance(early_deployments, Mapping) else early_deployments
+            )
+        return self._deployment_ids(self._get_all_deployments(model_name=resolved, team_id=team_id))
+
+    @staticmethod
+    def _deployment_ids(deployments: Sequence[Mapping[str, object]]) -> frozenset[str]:
+        return frozenset(
+            str(model_info["id"])
+            for deployment in deployments
+            for model_info in (deployment.get("model_info"),)
+            if isinstance(model_info, Mapping) and model_info.get("id") is not None
+        )
+
     def has_model_id(self, candidate_id: str) -> bool:
         """
         O(1) membership check for a deployment ID without allocating large lists.
@@ -11719,6 +11845,7 @@ class Router:
         result and bypass budget enforcement.
         """
         self._cached_get_model_group_info.cache_clear()
+        self.cached_deployment_model_info.cache_clear()
         self._zero_cost_cache.clear()
         self._routing_group_rows = None
 
@@ -11847,7 +11974,7 @@ class Router:
 
         _existing_router_settings: Final = self.get_settings()
         rebuild_routing_groups = False
-        relink_lar1_from_args = False
+        routing_args_updated = False
         for var in kwargs:
             if var in RUNTIME_UPDATABLE_ROUTER_SETTINGS:
                 if var in _int_settings:
@@ -11886,15 +12013,13 @@ class Router:
                                 )
                             rebuild_routing_groups = True
                     elif var == "routing_strategy_args":
-                        relink_lar1_from_args = True
+                        routing_args_updated = True
                     setattr(self, var, value)
             else:
                 verbose_router_logger.debug("Setting %s is not allowed", var)
 
-        if relink_lar1_from_args and self._normalize_strategy(self.routing_strategy) == "lar1":
-            from litellm.router_strategy.lar1_routing import apply_lar1_routing_strategy
-
-            apply_lar1_routing_strategy(self, self.routing_strategy_args)
+        if routing_args_updated:
+            self._apply_updated_routing_strategy_args()
 
         if rebuild_routing_groups:
             self._init_routing_groups(self._routing_groups_input)
@@ -12040,7 +12165,7 @@ class Router:
         try:
             if not self._pre_call_checks_need_token_count(model, healthy_deployments):
                 return None
-            return await asyncify(self._count_pre_call_check_tokens)(
+            return await offload_token_count(self._count_pre_call_check_tokens)(
                 messages=cast(list[dict[str, str]] | None, messages),  # cast-ok: forwarded to the sync counter
                 input=cast(str | list | None, input),  # cast-ok: forwarded to the sync counter
                 request_kwargs=request_kwargs,
@@ -12268,27 +12393,7 @@ class Router:
             if team_deployments:
                 return model, team_deployments
         elif include_team_models:
-            team_deployments = [
-                self.model_list[index]
-                for (_, public_model_name), indices in self.team_model_to_deployment_indices.items()
-                if public_model_name == model
-                for index in indices
-            ]
-            team_ids: Final = {
-                team_id
-                for deployment in team_deployments
-                for team_id in [(deployment.get("model_info") or {}).get("team_id")]
-                if team_id is not None
-            }
-            if len(team_ids) > 1:
-                raise litellm.BadRequestError(
-                    message=(
-                        f"Model name '{model}' matches deployments from multiple teams. "
-                        "Specify the deployment ID directly to disambiguate."
-                    ),
-                    model=model,
-                    llm_provider="",
-                )
+            team_deployments = self._team_deployments_across_teams(model)
             if team_deployments:
                 return model, team_deployments
 
@@ -12315,6 +12420,45 @@ class Router:
 
         return None
 
+    def _team_deployments_across_teams(self, model: str) -> list[DeploymentTypedDict]:
+        """Every team's deployments under public name `model`, for a proxy admin calling without a team."""
+        team_deployments: Final = [
+            self.model_list[index]
+            for (_, public_model_name), indices in self.team_model_to_deployment_indices.items()
+            if public_model_name == model
+            for index in indices
+        ]
+        team_ids: Final = {
+            team_id
+            for deployment in team_deployments
+            for team_id in [(deployment.get("model_info") or {}).get("team_id")]
+            if team_id is not None
+        }
+        if len(team_ids) > 1:
+            raise litellm.BadRequestError(
+                message=(
+                    f"Model name '{model}' matches deployments from multiple teams. "
+                    "Specify the deployment ID directly to disambiguate."
+                ),
+                model=model,
+                llm_provider="",
+            )
+        return team_deployments
+
+    def deployments_for_request(
+        self, model: str, request_kwargs: Mapping[str, object]
+    ) -> Sequence[DeploymentTypedDict]:
+        """The deployments `model` names for this caller, through the same alias, then team-first, then
+        global, then admin-across-teams resolution `_common_checks_available_deployment` applies, so
+        strategy selection and compression policy can never disagree with deployment selection about
+        which marker a name means."""
+        registered_name: Final = self._get_model_from_alias(model=model) or model
+        team_id: Final = get_request_team_id(request_kwargs)
+        deployments: Final = self._get_all_deployments(model_name=registered_name, team_id=team_id)
+        if deployments or team_id is not None or not _is_proxy_admin_request(request_kwargs):
+            return deployments
+        return self._team_deployments_across_teams(registered_name)
+
     @staticmethod
     def _is_strategy_marker_deployment(deployment: Mapping[str, object]) -> bool:
         litellm_params: Final = deployment.get("litellm_params")
@@ -12342,11 +12486,7 @@ class Router:
         - Dict, if specific model chosen
         """
 
-        request_team_id: str | None = None
-        if request_kwargs is not None:
-            metadata: Final = request_kwargs.get("metadata") or {}
-            litellm_metadata: Final = request_kwargs.get("litellm_metadata") or {}
-            request_team_id = metadata.get("user_api_key_team_id") or litellm_metadata.get("user_api_key_team_id")
+        request_team_id: Final = get_request_team_id(request_kwargs)
         # check if aliases set on litellm model alias map
         if specific_deployment is True:
             return model, self._get_deployment_by_litellm_model(model=model)
@@ -12371,7 +12511,9 @@ class Router:
                 include_team_models=_is_proxy_admin_request(request_kwargs),
             )
             if early is not None:
-                return early
+                if not isinstance(early[1], list):
+                    return early
+                return early[0], self._drop_strategy_markers(early[0], early[1])
 
         ## get healthy deployments
         ### get all deployments
@@ -12448,19 +12590,22 @@ class Router:
                 model
             ]  # update the model to the actual value if an alias has been passed in
 
-        marker_flags: Final = tuple(self._is_strategy_marker_deployment(d) for d in healthy_deployments)
-        if not any(marker_flags):
-            return model, healthy_deployments
-        selectable: Final = [  # mutable-ok: matches this function's list contract expected by downstream filters
-            d for d, is_marker in zip(healthy_deployments, marker_flags, strict=True) if not is_marker
+        return model, self._drop_strategy_markers(model, healthy_deployments)
+
+    def _drop_strategy_markers(
+        self, model: str, deployments: Sequence[DeploymentTypedDict]
+    ) -> list[DeploymentTypedDict]:
+        """A strategy marker is never a callable deployment, whichever resolution arm produced it."""
+        selectable: Final = [  # mutable-ok: matches _common_checks_available_deployment's list contract
+            d for d in deployments if not self._is_strategy_marker_deployment(d)
         ]
-        if not selectable:
+        if deployments and not selectable:
             raise litellm.BadRequestError(
                 message=f"You passed in model={model}. {RouterErrors.only_strategy_marker_deployments.value}",
                 model=model,
                 llm_provider="",
             )
-        return model, selectable
+        return selectable
 
     def _filter_deployments_by_model_access_groups(
         self,
@@ -13150,12 +13295,8 @@ class Router:
 
         return filtered
 
-    def _model_name_has_plain_deployments(self, model: str) -> bool:
-        indices: Final = self.model_name_to_deployment_indices.get(model) or ()
-        return any(not self._is_strategy_marker_deployment(self.model_list[idx]) for idx in indices)
-
     def _select_pre_routing_strategy(
-        self, model: str, request_kwargs: dict
+        self, model: str, request_kwargs: Mapping[str, object]
     ) -> "TaggedPreRoutingStrategy[PreRoutingStrategy] | None":
         """
         Resolve the pre-routing strategy for `model`, disambiguating deployments
@@ -13166,6 +13307,12 @@ class Router:
         deployment the strategy was registered from via its (model_name, tags)
         pair.
 
+        The registries are keyed by the marker deployment's own `model_name`, which
+        for a team-scoped router is the internal `model_name_{team}_{uuid}` while
+        the caller sends the team's public name. So the names looked up are the
+        `model_name`s of whatever deployments this caller's request resolves `model`
+        to, and `model` itself when it resolves to none.
+
         With tag filtering enabled, router-wide or by the request's
         enable_tag_filtering (which the proxy sets from key/team
         router_settings), strategies that all carry real tags matching none of
@@ -13173,12 +13320,14 @@ class Router:
         deployments: returning None hands the request to ordinary tag-aware
         deployment selection.
         """
-        candidates: Final[list[TaggedPreRoutingStrategy[PreRoutingStrategy]]] = [
-            *self.auto_routers.get(model, []),
-            *self.complexity_routers.get(model, []),
-            *self.adaptive_routers.get(model, []),
-            *self.quality_routers.get(model, []),
-        ]
+        registries: Final = (self.auto_routers, self.complexity_routers, self.adaptive_routers, self.quality_routers)
+        if not any(registries):
+            return None
+        deployments: Final = self.deployments_for_request(model, request_kwargs)
+        registered_names: Final = tuple(dict.fromkeys(str(d["model_name"]) for d in deployments)) or (model,)
+        candidates: Final = tuple(
+            tagged for registry in registries for name in registered_names for tagged in registry.get(name, [])
+        )
         if not candidates:
             return None
 
@@ -13196,7 +13345,7 @@ class Router:
         if (
             (self.enable_tag_filtering or request_scoped_filtering)
             and all(tagged.tags for tagged in candidates)
-            and self._model_name_has_plain_deployments(model)
+            and any(not self._is_strategy_marker_deployment(d) for d in deployments)
         ):
             return None
         return candidates[0]
@@ -13247,8 +13396,10 @@ class Router:
                 return await session_cache.async_get_cache(key=cache_key)
             return await session_cache.redis_cache.async_get_cache(key=cache_key)
         except Exception as e:  # noqa: BLE001  # an optional binding must not make routing depend on Redis
-            verbose_router_logger.warning(
-                "Failed to read Claude Code session router binding; using the requested model: %s",
+            log_redis_failure(
+                verbose_router_logger,
+                logging.WARNING,
+                "Failed to read Claude Code session router binding; using the requested model",
                 e,
             )
             return None
@@ -13308,11 +13459,12 @@ class Router:
 
         Used for the litellm auto-router to modify the request before the routing decision is made.
 
-        `model` is whatever the caller asked for, which may be a `model_group_alias` key, while the
-        strategy registries and the marker deployment are keyed by the marker's own `model_name`, so
-        every lookup below resolves the alias first. Only the lookups: the caller-facing name stays
-        the alias, since spend metadata is stamped before routing and the response carries the tier
-        group the strategy picked.
+        `model` is whatever the caller asked for, which may be a `model_group_alias` key or a team's
+        public model name, while the strategy registries and the marker deployment are keyed by the
+        marker's own `model_name`, so every lookup below resolves the alias first and the team name
+        through the deployment path. Only the lookups: the caller-facing name stays the alias, since
+        spend metadata is stamped before routing and the response carries the tier group the
+        strategy picked.
         """
         requested_registered_model_name: Final = self._get_model_from_alias(model=model) or model
         registered_model_name: Final = await self._resolve_claude_code_session_router(
@@ -13349,7 +13501,6 @@ class Router:
             messages_for_routing,
             model_hop_compression_armed,
             policy_for_model,
-            team_id_from_request,
         )
 
         # Same tag-aware lookup the proxy's pre-call arming used, so an alias with
@@ -13357,7 +13508,7 @@ class Router:
         compression_policy: Final = policy_for_model(
             llm_router=self,
             model_alias=registered_model_name,
-            team_id=team_id_from_request(request_kwargs),
+            request_kwargs=request_kwargs,
             request_tags=_get_tags_from_request_kwargs(request_kwargs),
         )
         # Shared compression already ran in the pre-call hook, so reuse it rather than
@@ -13426,7 +13577,9 @@ class Router:
         # Per-tier `litellm_params` on the hook response are deliberate overrides
         # the caller applies on top, so those keys are never forwarded here.
         marker_params: Final = (
-            self._forwardable_alias_marker_params(model=registered_model_name, strategy_tags=selected_strategy.tags)
+            self._forwardable_alias_marker_params(
+                model=registered_model_name, strategy_tags=selected_strategy.tags, request_kwargs=request_kwargs
+            )
             if pre_routing_hook_response is not None
             else ()
         )
@@ -13444,13 +13597,14 @@ class Router:
         return pre_routing_hook_response
 
     def _forwardable_alias_marker_params(
-        self, model: str, strategy_tags: tuple[str, ...]
+        self, model: str, strategy_tags: tuple[str, ...], request_kwargs: Mapping[str, object]
     ) -> tuple[tuple[str, object], ...]:
         marker_params: Final = tuple(
             litellm_params
-            for idx in self.model_name_to_deployment_indices.get(model, ())
-            if isinstance(litellm_params := self.model_list[idx].get("litellm_params", {}), dict)
-            and str(litellm_params.get("model", "")).startswith(AUTO_ROUTER_MODEL_PREFIX)
+            for deployment in self.deployments_for_request(model, request_kwargs)
+            if str((litellm_params := deployment["litellm_params"]).get("model", "")).startswith(
+                AUTO_ROUTER_MODEL_PREFIX
+            )
         )
         tag_matched: Final = tuple(
             params for params in marker_params if tuple(params.get("tags") or ()) == strategy_tags
diff --git a/litellm/router_strategy/base_routing_strategy.py b/litellm/router_strategy/base_routing_strategy.py
index 8235761ca98..686d57e2b77 100644
--- a/litellm/router_strategy/base_routing_strategy.py
+++ b/litellm/router_strategy/base_routing_strategy.py
@@ -3,12 +3,13 @@ Base class across routing strategies to abstract commmon functions like batch in
 """
 
 import asyncio
+import logging
 from abc import ABC
 from typing import Final
 
 from litellm._logging import verbose_router_logger
 from litellm.caching.caching import DualCache
-from litellm.caching.redis_cache import RedisPipelineIncrementOperation
+from litellm.caching.redis_cache import RedisPipelineIncrementOperation, log_redis_failure
 from litellm.constants import DEFAULT_REDIS_SYNC_INTERVAL
 
 
@@ -147,7 +148,7 @@ class BaseRoutingStrategy(ABC):
                 return return_result
 
         except Exception as e:
-            verbose_router_logger.error("Error syncing in-memory cache with Redis: %s", e)
+            log_redis_failure(verbose_router_logger, logging.ERROR, "Error syncing in-memory cache with Redis", e)
             self.redis_increment_operation_queue = []
 
     def add_to_in_memory_keys_to_update(self, key: str):
diff --git a/litellm/router_strategy/budget_limiter.py b/litellm/router_strategy/budget_limiter.py
index a8d51f95e45..3e094df7ac8 100644
--- a/litellm/router_strategy/budget_limiter.py
+++ b/litellm/router_strategy/budget_limiter.py
@@ -20,6 +20,7 @@ anthropic:
 
 import asyncio
 import builtins
+import logging
 from collections.abc import Mapping
 from datetime import datetime, timedelta, timezone
 from typing import Any, Final
@@ -27,7 +28,7 @@ from typing import Any, Final
 import litellm
 from litellm._logging import verbose_router_logger
 from litellm.caching.caching import DualCache
-from litellm.caching.redis_cache import RedisPipelineIncrementOperation
+from litellm.caching.redis_cache import RedisCache, RedisPipelineIncrementOperation, log_redis_failure
 from litellm.integrations.custom_logger import CustomLogger, Span
 from litellm.litellm_core_utils.core_helpers import (
     get_metadata_variable_name_from_kwargs,
@@ -92,6 +93,13 @@ class _LiteLLMParamsDictView:
         return dict(self._params)
 
 
+async def _push_increments_to_redis(redis_cache: RedisCache, queued: list[RedisPipelineIncrementOperation]) -> None:
+    try:
+        await redis_cache.async_increment_pipeline(increment_list=queued)
+    except Exception as e:
+        log_redis_failure(verbose_router_logger, logging.ERROR, "Error syncing in-memory cache with Redis", e)
+
+
 class RouterBudgetLimiting(CustomLogger):
     def __init__(
         self,
@@ -536,17 +544,13 @@ class RouterBudgetLimiting(CustomLogger):
                 "Pushing Redis Increment Pipeline for queue: %s",
                 self.redis_increment_operation_queue,
             )
-            if len(self.redis_increment_operation_queue) > 0:
-                asyncio.create_task(
-                    self.dual_cache.redis_cache.async_increment_pipeline(
-                        increment_list=self.redis_increment_operation_queue,
-                    )
-                )
-
+            queued: Final = self.redis_increment_operation_queue
             self.redis_increment_operation_queue = []
+            if queued:
+                asyncio.create_task(_push_increments_to_redis(self.dual_cache.redis_cache, queued))
 
         except Exception as e:
-            verbose_router_logger.error("Error syncing in-memory cache with Redis: %s", e)
+            log_redis_failure(verbose_router_logger, logging.ERROR, "Error syncing in-memory cache with Redis", e)
 
     async def _sync_in_memory_spend_with_redis(self):
         """
@@ -601,7 +605,7 @@ class RouterBudgetLimiting(CustomLogger):
                         verbose_router_logger.debug("Updated in-memory cache for %s: %s", key, value)
 
         except Exception as e:
-            verbose_router_logger.error("Error syncing in-memory cache with Redis: %s", e)
+            log_redis_failure(verbose_router_logger, logging.ERROR, "Error syncing in-memory cache with Redis", e)
 
     def _get_budget_config_for_deployment(
         self,
diff --git a/litellm/router_strategy/complexity_router/README.md b/litellm/router_strategy/complexity_router/README.md
index d605b43e42a..1a4764c291e 100644
--- a/litellm/router_strategy/complexity_router/README.md
+++ b/litellm/router_strategy/complexity_router/README.md
@@ -361,6 +361,19 @@ model_list:
 keep the classifier deployment or provider default, or set a supported value such as `none` or
 `low` to override that call.
 
+When the current ask is a Responses API `agent_message` containing `encrypted_content`, LLM
+classification preserves the encrypted task and uses native Responses. This also bypasses the
+local scoring shortcut in `heuristic_first` and `hybrid` modes. The configured classifier must use
+a native OpenAI or Azure OpenAI Responses deployment with access to the encrypted content. The
+provider handles the encrypted task, and the classifier still chooses the tier dynamically
+
+Compatibility is checked after normal deployment selection. A paused incompatible member of the
+classifier group does not prevent an eligible compatible deployment from classifying the task
+
+Unsupported classifier deployments and provider decryption errors use the existing
+`classifier_fallback` policy. No fixed tier is introduced for encrypted tasks. Plaintext asks and
+requests carrying only historical encrypted reasoning retain the existing classifier path
+
 Classifier calls have a one-attempt hard deadline. After a timeout, the router opens a process-local
 circuit for that classifier and sends every session through `classifier_fallback` for
 `classifier_llm_config.circuit_breaker_cooldown_seconds` (30 seconds by default). When the cooldown
@@ -442,11 +455,26 @@ If 2+ reasoning markers are detected in the user message, the request is promote
 
 Reasoning markers in the system prompt do **not** trigger the reasoning override. This prevents system prompts like "Think step by step before answering" from forcing all requests to the reasoning tier.
 
+For requests identified by a `claude-cli/` or `claude-code/` user agent, the LLM classifier omits caller system
+text to avoid classifying environment, agent, and skill catalogs. The current ask, configured prior-turn context,
+and trajectory signal remain unchanged. The routed completion still receives the original system text. This
+also excludes genuine task constraints supplied only in Claude Code system messages. Other clients keep the
+existing system-context behavior. The browser routing preview has no client-identity field and retains that
+generic behavior; use the real client when checking Claude Code routing.
+
 ### Harness Reminder Blocks
 
 Agent harnesses inject their own context into the conversation as ordinary message text. That text is plumbing, not something a human asked for, so the router strips complete reminder blocks before classifying and picking a tier. A turn that is nothing but a reminder block strips to empty and is skipped, and the router falls back to the last real ask instead
 
-By default a block is anything between `<system-reminder>` and `</system-reminder>`. `reminder_markers` replaces that with your harness's own delimiters. Many harnesses use a different envelope per agent type, so list every pair you emit:
+By default the router strips complete `<system-reminder>` blocks. For requests with a Codex user agent, it also strips complete `<environment_context>`, `<recommended_plugins>`, `<user_instructions>`, and `<environments_instructions>` blocks, plus repository instructions from the fixed heading prefix `# AGENTS.md instructions for ` through `</INSTRUCTIONS>`, regardless of the repository path. Other clients keep those tags and their contents
+
+The proxy records the incoming user agent in request metadata. SDK callers can supply `metadata.user_agent` (or `litellm_metadata.user_agent` on Responses requests), or configure `reminder_markers` explicitly when their client identity is unavailable
+
+The Codex `Message Type: NEW_TASK` wrapper and its delegated-task payload remain available for classification. Cleanup applies to the current ask and quoted prior turns; the routed request retains its original content
+
+In `classification_mode: user_turn`, complete text-only reminder tails leave the preceding fresh ask eligible for classification. Assistant turns and tool results still mark continuations, including tool results carried alongside reminder text
+
+`reminder_markers` replaces these defaults with your harness's own delimiters. Many harnesses use a different envelope per agent type, so list every pair you emit:
 
 ```yaml
 model_list:
@@ -461,7 +489,7 @@ model_list:
             close: "[[SUBAGENT_CONTEXT_END]]"
 ```
 
-Setting `reminder_markers` replaces the built-in `<system-reminder>` pair rather than adding to it, so list that pair too if your harness also emits it. Matching is case-insensitive. Blocks that nest or overlap across pairs are stripped whole. An unclosed delimiter is not a block and is left in place, which keeps prose that merely mentions a delimiter from being eaten
+Setting `reminder_markers` replaces all built-in pairs, including the Codex heading pair, so include every default your harness still needs. Matching is case-insensitive. Blocks that nest or overlap across pairs are stripped whole. An unclosed delimiter is not a block and is left in place, which keeps prose that merely mentions a delimiter from being eaten
 
 ### Code Detection
 
diff --git a/litellm/router_strategy/complexity_router/complexity_router.py b/litellm/router_strategy/complexity_router/complexity_router.py
index 62b30365f4a..7519f4c5156 100644
--- a/litellm/router_strategy/complexity_router/complexity_router.py
+++ b/litellm/router_strategy/complexity_router/complexity_router.py
@@ -25,7 +25,7 @@ from threading import Lock
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Literal, NamedTuple, cast
 
-from pydantic import BaseModel, create_model
+from pydantic import BaseModel, TypeAdapter, ValidationError, create_model
 
 from litellm._logging import verbose_router_logger
 from litellm.constants import (
@@ -36,9 +36,11 @@ from litellm.constants import (
     SESSION_ID_GENERATED_METADATA_KEY,
 )
 from litellm.integrations.custom_logger import CustomLogger
+from litellm.litellm_core_utils.classifier_logging import masked_originating_request
 from litellm.litellm_core_utils.core_helpers import (
     _get_parent_otel_span_from_kwargs,
     get_metadata_variable_name_from_kwargs,
+    is_codex_user_agent,
 )
 from litellm.litellm_core_utils.internal_call_metadata import forwarded_internal_call_metadata
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
@@ -46,6 +48,7 @@ from litellm.litellm_core_utils.prompt_templates.common_utils import (
     request_contains_image_content,
 )
 from litellm.litellm_core_utils.sensitive_data_masker import mask_credentials_in_payload
+from litellm.llms.anthropic.common_utils import is_claude_code_user_agent
 from litellm.llms.base_llm.base_utils import type_to_response_format_param
 from litellm.router_strategy.adaptive_router.classifier import classify_prompt
 from litellm.router_strategy.complexity_router.tier_predictor import (
@@ -56,6 +59,7 @@ from litellm.types.llms.openai import (
     AllMessageValues,
     ChatCompletionImageObject,
     ChatCompletionTextObject,
+    ResponsesAPIResponse,
 )
 from litellm.types.utils import (
     AUTOROUTER_CLASSIFIER_CALL_ORIGIN,
@@ -364,7 +368,7 @@ def _parent_session_kwargs(request_kwargs: Mapping[str, Any] | None) -> Mapping[
     return {k: kwargs[k] for k in ("litellm_session_id", "litellm_trace_id") if kwargs.get(k) is not None}
 
 
-def _response_cost_or_none(response: ModelResponse) -> float | None:
+def _response_cost_or_none(response: ModelResponse | ResponsesAPIResponse) -> float | None:
     hidden_params: Final = response._hidden_params
     if not isinstance(hidden_params, dict):
         return None
@@ -387,6 +391,13 @@ def _effective_turn_off_message_logging(request_kwargs: Mapping[str, object] | N
 _REMINDER_OPEN: Final = "<system-reminder>"
 _REMINDER_CLOSE: Final = "</system-reminder>"
 _DEFAULT_REMINDER_MARKERS: Final = ((_REMINDER_OPEN, _REMINDER_CLOSE),)
+_CODEX_REMINDER_MARKERS: Final = _DEFAULT_REMINDER_MARKERS + (
+    ("<environment_context>", "</environment_context>"),
+    ("<recommended_plugins>", "</recommended_plugins>"),
+    ("<user_instructions>", "</user_instructions>"),
+    ("<environments_instructions>", "</environments_instructions>"),
+    ("# agents.md instructions for ", "</instructions>"),
+)
 
 _TRUNCATION_MARKER: Final = "..."
 _TRUNCATION_HEAD_FRACTION: Final = 0.3
@@ -486,6 +497,42 @@ def _human_text(content: object, marker_pairs: tuple[tuple[str, str], ...] = _DE
     return _strip_reminder_blocks(_message_text(content), marker_pairs)
 
 
+def _encrypted_classifier_task(
+    request_kwargs: Mapping[str, object] | None,
+    marker_pairs: tuple[tuple[str, str], ...],
+) -> dict[str, object] | None:
+    from litellm.litellm_core_utils.prompt_templates.factory import resolve_structured_messages
+
+    raw_input: Final = (request_kwargs or EMPTY_MAPPING).get("input")
+    if not isinstance(raw_input, list) or (request_kwargs or EMPTY_MAPPING).get("messages"):
+        return None
+    try:
+        items: Final = TypeAdapter(tuple[dict[str, object], ...]).validate_python(raw_input)
+    except ValidationError:
+        return None
+    current: Final = next(
+        (
+            item
+            for item in reversed(items)
+            if (messages := resolve_structured_messages(messages=None, request_kwargs={"input": [item]}))
+            and any(_iter_human_asks_newest_first(messages, marker_pairs))
+        ),
+        None,
+    )
+    if current is None or current.get("type") != "agent_message" or not isinstance(current.get("content"), list):
+        return None
+    try:
+        parts: Final = TypeAdapter(tuple[dict[str, object], ...]).validate_python(current["content"])
+    except ValidationError:
+        return None
+    if not any(part.get("type") == "encrypted_content" and part.get("encrypted_content") for part in parts):
+        return None
+    return {
+        **current,
+        "content": [part for part in parts if part.get("type") in ("input_text", "encrypted_content")],
+    }
+
+
 def _iter_human_asks_newest_first(
     messages: Sequence[Mapping[str, object]],
     marker_pairs: tuple[tuple[str, str], ...] = _DEFAULT_REMINDER_MARKERS,
@@ -591,6 +638,18 @@ def _last_human_ask_index(
     )
 
 
+def _is_reminder_only_turn(message: Mapping[str, object], marker_pairs: tuple[tuple[str, str], ...]) -> bool:
+    if message.get("role") != "user":
+        return False
+    content: Final = message.get("content")
+    if not isinstance(content, str) and not (
+        isinstance(content, list) and all(isinstance(part, Mapping) and part.get("type") == "text" for part in content)
+    ):
+        return False
+    text: Final = _message_text(content)
+    return bool(text.strip()) and not _strip_reminder_blocks(text, marker_pairs)
+
+
 def _newest_turn_is_human_ask(
     messages: Sequence[Mapping[str, object]] | None,
     marker_pairs: tuple[tuple[str, str], ...] = _DEFAULT_REMINDER_MARKERS,
@@ -601,21 +660,23 @@ def _newest_turn_is_human_ask(
     Anchored on `_last_human_ask_index` so every surface's plumbing reads as a continuation:
     chat-completions tool turns are role=tool, Messages-surface tool_result turns flatten to empty
     human text, and a hybrid turn carrying an ask alongside a tool_result still counts as an ask.
-    Compared against the newest non-system message rather than the raw tail, because Claude Code
-    appends a system-role reminder after the human turn; that trailing plumbing is neither an ask
-    nor loop traffic and must not turn a fresh ask into a continuation. An unreadable request (no
-    messages) is treated as a continuation: there is no ask to classify, which is the same reading
-    `_extract_current_ask_and_system_prompt` gives it downstream.
+    Trailing system messages and complete text-only reminders do not turn a fresh ask into a
+    continuation. Assistant turns and non-text content, including tool results alongside reminders,
+    still form continuation boundaries. An unreadable request has no ask to classify.
     """
     if not messages:
         return False
-    newest_non_system: Final = next(
-        (index for index in range(len(messages) - 1, -1, -1) if messages[index].get("role") != "system"),
+    newest_activity: Final = next(
+        (
+            index
+            for index in range(len(messages) - 1, -1, -1)
+            if messages[index].get("role") != "system" and not _is_reminder_only_turn(messages[index], marker_pairs)
+        ),
         None,
     )
-    if newest_non_system is None:
+    if newest_activity is None:
         return False
-    return _last_human_ask_index(messages, marker_pairs) == newest_non_system
+    return _last_human_ask_index(messages, marker_pairs) == newest_activity
 
 
 def _iter_system_scope_texts(
@@ -1630,6 +1691,10 @@ class ComplexityRouter(CustomLogger):
             return self._classify_with_heuristic_v2(prompt)
         if self.config.classifier_type == "custom":
             return await self._classify_with_plugin(prompt, system_prompt, request_kwargs, raw_messages)
+        if self.config.classifier_type in ("heuristic_first", "hybrid") and _encrypted_classifier_task(
+            request_kwargs, self._reminder_markers_for_request(request_kwargs or EMPTY_MAPPING)
+        ):
+            return await self._llm_classifier_outcome(prompt, system_prompt, request_kwargs, messages)
         if self.config.classifier_type == "heuristic_first" and self.config.classifier_llm_config is not None:
             return await self._classify_heuristic_first(prompt, system_prompt, request_kwargs, messages)
         if self.config.classifier_type == "hybrid" and self.config.classifier_llm_config is not None:
@@ -1924,16 +1989,12 @@ class ComplexityRouter(CustomLogger):
         Call the configured classifier model with a system/user role split and prior-turn context.
 
         Builds a structured classification prompt with:
-        - System message: the stable classifier rubric AND the caller's own system prompt (task
-          constraints). This is the largest, most repeated part of the call, so keeping it in the
-          system role lets the provider prompt-cache it across a session's classifier calls.
-        - User message: the variable payload -- a few prior user turns for context and the current
-          ask to classify.
+        - System message: the stable classifier rubric.
+        - User message: the caller's system prompt quoted as task context, prior turns, and the current ask.
 
         Args:
             prompt: The current user ask text (already extracted as the real human ask, not tool results)
-            system_prompt: The caller's system prompt (task constraints), always included so later
-                turns never lose it
+            system_prompt: Caller task constraints, omitted from classification for Claude Code requests
             request_kwargs: Request metadata for spend attribution
             messages: Full message history for extracting prior turns and the trajectory signal
         """
@@ -1944,6 +2005,7 @@ class ComplexityRouter(CustomLogger):
             raise ValueError("classifier_llm_config is not set")
 
         include_assistant: Final = self.config.classifier_context_include_assistant_turns
+        marker_pairs: Final = self._reminder_markers_for_request(request_kwargs or {})
         context_enabled: Final = bool(messages) and self.config.classifier_context_window_size > 0
         prior_turns: Final = (
             _extract_prior_turns(
@@ -1953,26 +2015,30 @@ class ComplexityRouter(CustomLogger):
                 budget_chars=self.config.classifier_context_budget_chars,
                 per_turn_chars=self.config.classifier_context_per_turn_chars,
                 include_assistant=include_assistant,
-                marker_pairs=self._reminder_markers,
+                marker_pairs=marker_pairs,
             )
             if context_enabled
             else ()
         )
         has_prior_conversation: Final = (
             context_enabled
-            and len(
-                tuple(
-                    islice(
-                        _iter_context_turns_newest_first(messages or (), include_assistant, self._reminder_markers), 2
-                    )
-                )
-            )
+            and len(tuple(islice(_iter_context_turns_newest_first(messages or (), include_assistant, marker_pairs), 2)))
             > 1
         )
 
+        encrypted_task: Final = _encrypted_classifier_task(request_kwargs, marker_pairs)
+        caller_system_prompt: Final = (
+            None
+            if any(
+                is_claude_code_user_agent(user_agent)
+                for metadata in (self._iter_metadata_dicts(request_kwargs) if request_kwargs is not None else ())
+                if isinstance(user_agent := metadata.get("user_agent"), str)
+            )
+            else system_prompt
+        )
         user_payload: Final = self._build_classifier_user_payload(
-            prompt=prompt,
-            system_prompt=system_prompt,
+            prompt="The delegated task in the following agent_message." if encrypted_task is not None else prompt,
+            system_prompt=caller_system_prompt,
             prior_turns=prior_turns,
             messages=messages,
             has_prior_conversation=has_prior_conversation,
@@ -2004,34 +2070,42 @@ class ComplexityRouter(CustomLogger):
         if llm_config.reasoning_effort is not None:
             classifier_call_params = MappingProxyType({"reasoning_effort": llm_config.reasoning_effort})
 
+        payload: Final = (
+            self._native_classifier_payload(messages_for_call, response_format, encrypted_task)
+            if encrypted_task is not None
+            else MappingProxyType(
+                {"messages": messages_for_call, "response_format": response_format, **classifier_call_params}
+            )
+        )
         proxy_server_request: Final = {
-            "body": {
-                "model": llm_config.model,
-                "messages": messages_for_call,
-                "response_format": response_format,
-                **classifier_call_params,
-            }
+            "originating_request_masked": masked_originating_request(request_kwargs),
+            "body": {"model": llm_config.model, **payload},
         }
+        classify: Final = (
+            self.litellm_router_instance.aresponses
+            if encrypted_task is not None
+            else self.litellm_router_instance.acompletion
+        )
 
         classifier_timeout_s: Final[float] = llm_config.timeout_ms / 1000
-        response: Final[ModelResponse] = await asyncio.wait_for(
-            self.litellm_router_instance.acompletion(
+        response: Final[ModelResponse | ResponsesAPIResponse] = await asyncio.wait_for(
+            classify(
                 model=llm_config.model,
-                messages=messages_for_call,
                 stream=False,
-                response_format=response_format,
                 timeout=classifier_timeout_s,
                 num_retries=0,
                 disable_fallbacks=True,
                 metadata=metadata,
                 proxy_server_request=proxy_server_request,
                 turn_off_message_logging=turn_off_message_logging,
-                **classifier_call_params,
+                **payload,
                 **_parent_session_kwargs(request_kwargs),
             ),
             timeout=classifier_timeout_s,
         )
-        content: Final = response.choices[0].message.content
+        content: Final = (
+            response.output_text if isinstance(response, ResponsesAPIResponse) else response.choices[0].message.content
+        )
         if not content:
             raise ValueError("LLM classifier returned empty content")
         raw_tier: Final = _LabeledTierClassification.model_validate_json(content).tier
@@ -2040,6 +2114,33 @@ class ComplexityRouter(CustomLogger):
             raise ValueError(f"LLM classifier returned an unrecognized tier: {raw_tier!r}")
         return tier, _response_cost_or_none(response)
 
+    def _native_classifier_payload(
+        self,
+        messages: list[AllMessageValues],  # mutable-ok: existing transformation accepts the SDK message list
+        response_format: Mapping[str, object],
+        encrypted_task: Mapping[str, object],
+    ) -> Mapping[str, object]:
+        from litellm.completion_extras.litellm_responses_transformation.transformation import (
+            LiteLLMResponsesTransformationHandler,
+        )
+
+        transformation: Final = LiteLLMResponsesTransformationHandler()
+        input_items, instructions = transformation.convert_chat_completion_messages_to_responses_api(messages)
+        llm_config: Final = self.config.classifier_llm_config
+        reasoning: Final = (
+            {"reasoning": {"effort": llm_config.reasoning_effort}}
+            if llm_config is not None and llm_config.reasoning_effort is not None
+            else {}
+        )
+        return {
+            "input": [*input_items, encrypted_task],
+            "instructions": instructions,
+            "text": transformation.transform_response_format_to_text_format(dict(response_format)),
+            "store": False,
+            "_require_encrypted_task_support": True,
+            **reasoning,
+        }
+
     @staticmethod
     def _build_classifier_user_payload(
         prompt: str,
@@ -2427,7 +2528,7 @@ class ComplexityRouter(CustomLogger):
             body if isinstance(body, Mapping) else None,
             resolved_messages,
             tuple(self.config.plan_mode_patterns or ()),
-            self._reminder_markers,
+            self._reminder_markers_for_request(request_kwargs),
         )
 
     def _matched_housekeeping_sentinel(self, newest_ask: str | None) -> str | None:
@@ -2568,14 +2669,14 @@ class ComplexityRouter(CustomLogger):
         """Real-tokenizer count of the resolved messages plus the out-of-band carriers, off the
         event loop; None when counting fails, and the gate then leaves the placement alone."""
         import litellm
-        from litellm.litellm_core_utils.asyncify import asyncify
+        from litellm.litellm_core_utils.token_counter import offload_token_count
 
         out_of_band: Final = self._out_of_band_request_text(request_kwargs)
         try:
-            counted: Final = await asyncify(litellm.token_counter)(
+            counted: Final = await offload_token_count(litellm.token_counter)(
                 messages=cast(list, resolved_messages)  # cast-ok: token_counter only iterates the sequence
             )
-            return counted + (await asyncify(litellm.token_counter)(text=out_of_band) if out_of_band else 0)
+            return counted + (await offload_token_count(litellm.token_counter)(text=out_of_band) if out_of_band else 0)
         except Exception as e:  # noqa: BLE001  # best-effort: an uncountable prompt must not fail the request
             verbose_router_logger.debug("ComplexityRouter: context-window token count failed. Got - %s", e)
             return None
@@ -3248,6 +3349,18 @@ class ComplexityRouter(CustomLogger):
         """
         return _extract_current_ask_and_system_prompt(messages)
 
+    def _reminder_markers_for_request(self, request_kwargs: Mapping[str, object]) -> tuple[tuple[str, str], ...]:
+        if self.config.reminder_markers is not None:
+            return self._reminder_markers
+        if any(
+            is_codex_user_agent(user_agent)
+            for metadata_key in ("litellm_metadata", "metadata")
+            if isinstance(metadata := request_kwargs.get(metadata_key), Mapping)
+            if isinstance(user_agent := metadata.get("user_agent"), str)
+        ):
+            return _CODEX_REMINDER_MARKERS
+        return _DEFAULT_REMINDER_MARKERS
+
     @staticmethod
     def _iter_metadata_dicts(request_kwargs: dict) -> list[dict]:
         """Metadata may land on `metadata` or `litellm_metadata` depending on the
@@ -3349,6 +3462,7 @@ class ComplexityRouter(CustomLogger):
         # chat-completions messages, so it is real work on every non-chat surface, and
         # both the conversation shape and the classifier read the same list.
         resolved_messages: Final = self._resolve_messages(messages, request_kwargs)
+        marker_pairs: Final = self._reminder_markers_for_request(request_kwargs)
         conversation_continuing: Final = _conversation_is_continuing(resolved_messages)
 
         use_session_affinity: Final = self._uses_tier_pin
@@ -3358,7 +3472,7 @@ class ComplexityRouter(CustomLogger):
         # In 'user_turn' mode a held pin is replayed only on continuation turns; a new human
         # ask falls through and re-classifies. session_affinity restores pin-first for asks too.
         pin_replay_allowed: Final = bool(self.config.session_affinity) or not _newest_turn_is_human_ask(
-            resolved_messages, self._reminder_markers
+            resolved_messages, marker_pairs
         )
 
         if cache_key is not None and pin_replay_allowed:
@@ -3369,7 +3483,7 @@ class ComplexityRouter(CustomLogger):
                 pin_escalation_keyword: str | None = None
                 if self.escalation_keywords:
                     user_message: Final = (
-                        _newest_turn_ask(resolved_messages, self._reminder_markers) if resolved_messages else None
+                        _newest_turn_ask(resolved_messages, marker_pairs) if resolved_messages else None
                     )
                     if user_message is not None:
                         pin_escalation_keyword = self._matched_escalation_keyword(user_message)
@@ -3557,7 +3671,8 @@ class ComplexityRouter(CustomLogger):
         # Determine whether the original request used messages directly
         has_original_messages: Final = messages is not None and len(messages) > 0
 
-        user_message, system_prompt = _extract_current_ask_and_system_prompt(resolved_messages, self._reminder_markers)
+        marker_pairs: Final = self._reminder_markers_for_request(request_kwargs)
+        user_message, system_prompt = _extract_current_ask_and_system_prompt(resolved_messages, marker_pairs)
         classifier_images: Final = self._classifier_image_parts(resolved_messages)
 
         if user_message is None and not classifier_images:
@@ -3591,7 +3706,7 @@ class ComplexityRouter(CustomLogger):
             )
 
         ask: Final = user_message or ""
-        newest_ask: Final = _newest_turn_ask(resolved_messages, self._reminder_markers)
+        newest_ask: Final = _newest_turn_ask(resolved_messages, marker_pairs)
         escalation_keyword: Final = self._matched_escalation_keyword(newest_ask) if newest_ask is not None else None
         # Resolved here rather than beside the classifier because the keyword-override path below
         # returns before any classification runs, and a forced tier gets stuck for the same reason
diff --git a/litellm/router_strategy/complexity_router/config.py b/litellm/router_strategy/complexity_router/config.py
index d28924c69b2..1f1b5a5cc4b 100644
--- a/litellm/router_strategy/complexity_router/config.py
+++ b/litellm/router_strategy/complexity_router/config.py
@@ -971,9 +971,11 @@ class ComplexityRouterConfig(BaseModel):
             "classified against what it refers to. Counts turns of both roles when "
             "classifier_context_include_assistant_turns is enabled. These turns are sent to the classifier "
             "model, which may "
-            "be a different deployment or provider than the routed completion model; that call already "
-            "carries the current user ask and the caller's system prompt in full. Set to 0 to send neither "
-            "prior turns nor any conversation context beyond the current ask. Only applies when "
+            "be a different deployment or provider than the routed completion model; that call carries "
+            "the current user ask and, except for Claude Code requests, the extracted system-role text in full. "
+            "Claude Code system text is omitted to avoid classifying harness instructions; the routed "
+            "completion still receives it. Set to 0 to send neither prior turns nor "
+            "any conversation context beyond the current ask. Only applies when "
             "classifier_type is 'llm'."
         ),
     )
@@ -985,9 +987,9 @@ class ComplexityRouterConfig(BaseModel):
             "context window, per classification call. Turns are taken newest first and quoted whole "
             "while they fit, so a conversation small enough to quote entirely is never cut; once the "
             "budget runs out the older turns are dropped whole and only the turn straddling the "
-            "boundary is truncated, into whatever space is left. The current ask and the caller's "
-            "system prompt sit outside this budget and are always sent in full, as does the numbering "
-            "each quoted turn carries. A budget under 120 leaves no room to quote a turn and "
+            "boundary is truncated, into whatever space is left. The current ask and, except for Claude "
+            "Code requests, the extracted system-role text sit outside this budget and are sent in full, as does "
+            "the numbering each quoted turn carries. A budget under 120 leaves no room to quote a turn and "
             "suppresses the block; set classifier_context_window_size to 0 to turn context off "
             "deliberately. Only applies when classifier_type is 'llm'."
         ),
@@ -1292,8 +1294,9 @@ class ComplexityRouterConfig(BaseModel):
             "Override the delimiter pairs used to recognize and strip harness-injected reminder "
             "blocks before classification. A harness that wraps injected context differently per "
             "agent type (main, subagent, cron) lists every pair it emits. Replaces, rather than "
-            "adds to, the built-in default of ('<system-reminder>', '</system-reminder>'), so a "
-            "harness that also emits that pair lists it too. Matching is case-insensitive."
+            "adds to, the built-in system-reminder pair and the Codex envelope pairs enabled "
+            "for Codex user agents, so list every built-in pair your harness also emits. "
+            "Matching is case-insensitive."
         ),
     )
 
diff --git a/litellm/router_strategy/least_busy.py b/litellm/router_strategy/least_busy.py
index 14e6592e1fd..0b73f4e31a7 100644
--- a/litellm/router_strategy/least_busy.py
+++ b/litellm/router_strategy/least_busy.py
@@ -1,3 +1,4 @@
+import logging
 from collections.abc import Mapping, Sequence
 from typing import Final
 
@@ -6,6 +7,7 @@ from typing_extensions import ReadOnly, TypedDict
 
 from litellm._logging import verbose_router_logger
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import log_redis_failure
 from litellm.integrations.custom_logger import CustomLogger
 
 IN_FLIGHT_COUNT_TTL_SECONDS: Final = 60 * 60
@@ -87,16 +89,22 @@ def _least_busy(
 
 
 def _warn_unreadable(model_group: str, error: Exception) -> None:
-    verbose_router_logger.warning(
-        "least-busy routing could not read the shared in-flight counts for %s, "
-        "falling back to this worker's own counts: %s",
-        model_group,
+    log_redis_failure(
+        verbose_router_logger,
+        logging.WARNING,
+        f"least-busy routing could not read the shared in-flight counts for {model_group}, "
+        "falling back to this worker's own counts",
         error,
     )
 
 
 def _warn_unwritable(key: str, error: Exception) -> None:
-    verbose_router_logger.warning("least-busy routing could not update the in-flight count under %s: %s", key, error)
+    log_redis_failure(
+        verbose_router_logger,
+        logging.WARNING,
+        f"least-busy routing could not update the in-flight count under {key}",
+        error,
+    )
 
 
 class LeastBusyLoggingHandler(CustomLogger):
diff --git a/litellm/router_strategy/lowest_latency.py b/litellm/router_strategy/lowest_latency.py
index 805d4ff9080..e902192811c 100644
--- a/litellm/router_strategy/lowest_latency.py
+++ b/litellm/router_strategy/lowest_latency.py
@@ -3,8 +3,11 @@
 import random
 from collections.abc import Sequence
 from datetime import datetime, timedelta
+from math import ceil
 from typing import TYPE_CHECKING, Any, Final
 
+from pydantic import Field
+
 import litellm
 from litellm import ModelResponse, token_counter, verbose_logger
 from litellm.caching.caching import DualCache
@@ -24,6 +27,7 @@ class RoutingArgs(LiteLLMPydanticObjectBase):
     ttl: float = 1 * 60 * 60  # 1 hour
     lowest_latency_buffer: float = 0
     max_latency_list_size: int = 10
+    ttft_percentile: float | None = Field(default=None, gt=0, le=1)
 
 
 def _average_latency(samples: Sequence[float]) -> float:
@@ -32,6 +36,12 @@ def _average_latency(samples: Sequence[float]) -> float:
     return sum(samples) / len(samples)
 
 
+def _percentile_latency(samples: Sequence[float], percentile: float) -> float:
+    values: Final = sorted(samples)
+    index: Final = ceil(len(values) * percentile) - 1
+    return values[index]
+
+
 def _ttft_seconds(elapsed: timedelta | float) -> float:
     if isinstance(elapsed, timedelta):
         return elapsed.total_seconds()
@@ -427,14 +437,17 @@ class LowestLatencyLoggingHandler(CustomLogger):
             item_rpm = item_map.get(precise_minute, {}).get("rpm", 0)
             item_tpm = item_map.get(precise_minute, {}).get("tpm", 0)
 
-            # get average latency or average ttft (depending on streaming/non-streaming)
             use_ttft = (
                 request_kwargs is not None
                 and request_kwargs.get("stream", None) is not None
                 and request_kwargs["stream"] is True
                 and len(item_ttft_latency) > 0
             )
-            average_latency = _average_latency(item_ttft_latency if use_ttft else item_latency)
+            selected_latency = (
+                _percentile_latency(item_ttft_latency, self.routing_args.ttft_percentile)
+                if use_ttft and self.routing_args.ttft_percentile is not None
+                else _average_latency(item_ttft_latency if use_ttft else item_latency)
+            )
 
             # -------------- #
             # Debugging Logic
@@ -443,7 +456,7 @@ class LowestLatencyLoggingHandler(CustomLogger):
             # this helps a user to debug why the router picked a specfic deployment      #
             _deployment_api_base = _deployment.get("litellm_params", {}).get("api_base", "")
             if _deployment_api_base is not None:
-                _latency_per_deployment[_deployment_api_base] = average_latency
+                _latency_per_deployment[_deployment_api_base] = selected_latency
             # -------------- #
             # End of Debugging Logic
             # -------------- #
@@ -453,7 +466,7 @@ class LowestLatencyLoggingHandler(CustomLogger):
             ):  # if user passed in tpm / rpm in the model_list
                 continue
             else:
-                potential_deployments.append((_deployment, average_latency))
+                potential_deployments.append((_deployment, selected_latency))
 
         if len(potential_deployments) == 0:
             return None
diff --git a/litellm/router_utils/add_retry_fallback_headers.py b/litellm/router_utils/add_retry_fallback_headers.py
index 3ec92ad226a..3251ea457cf 100644
--- a/litellm/router_utils/add_retry_fallback_headers.py
+++ b/litellm/router_utils/add_retry_fallback_headers.py
@@ -50,6 +50,12 @@ def prepare_response_for_header_attachment(response: object) -> object | None:
     return response
 
 
+def response_has_hidden_params(response: object) -> bool:
+    if isinstance(response, dict):
+        return "_hidden_params" in response
+    return hasattr(response, "_hidden_params")
+
+
 def ensure_response_additional_headers(response: object) -> dict[str, object]:
     hidden_params: Final = get_hidden_params_dict(response, create=isinstance(response, dict))
     _write_hidden_params(response, hidden_params)
diff --git a/litellm/router_utils/common_utils.py b/litellm/router_utils/common_utils.py
index 280a7defcf8..49cca8ee99e 100644
--- a/litellm/router_utils/common_utils.py
+++ b/litellm/router_utils/common_utils.py
@@ -7,6 +7,7 @@ from typing import TYPE_CHECKING, Final
 if TYPE_CHECKING:
     from litellm.types.llms.openai import OpenAIFileObject
 
+import litellm
 from litellm._logging import verbose_logger, verbose_router_logger
 from litellm.constants import ROUTER_FALLBACK_ERROR_DETAIL_MAX_CHARS
 from litellm.exceptions import BadRequestError
@@ -26,6 +27,18 @@ def _is_proxy_admin_request(request_kwargs: Mapping[str, object] | None) -> bool
     return getattr(user_api_key_auth, "user_role", None) == "proxy_admin"
 
 
+def get_request_team_id(request_kwargs: Mapping[str, object] | None) -> str | None:
+    """The caller's team id, from whichever metadata bucket this surface writes to."""
+    if request_kwargs is None:
+        return None
+    for bucket_name in ("metadata", "litellm_metadata"):
+        bucket = request_kwargs.get(bucket_name)
+        team_id = bucket.get("user_api_key_team_id") if isinstance(bucket, Mapping) else None
+        if isinstance(team_id, str) and team_id:
+            return team_id
+    return None
+
+
 def resolve_model_group_alias(model_group_alias: object, model: str) -> str | None:
     """
     Resolve ``model`` through a ``model_group_alias`` map.
@@ -110,7 +123,7 @@ def filter_team_based_models(
 
     metadata: Final = request_kwargs.get("metadata") or {}
     litellm_metadata: Final = request_kwargs.get("litellm_metadata") or {}
-    request_team_id: Final = metadata.get("user_api_key_team_id") or litellm_metadata.get("user_api_key_team_id")
+    request_team_id: Final = get_request_team_id(request_kwargs)
     if request_team_id is None and _is_proxy_admin_request(request_kwargs) and isinstance(healthy_deployments, list):
         requested_model: Final = (
             request_kwargs.get("model") or metadata.get("model_group") or litellm_metadata.get("model_group")
@@ -244,6 +257,32 @@ PROVIDER_SCOPED_CREDENTIAL_PARAMS: Final[Mapping[str, frozenset[str]]] = Mapping
 )
 
 
+def provider_for_generic_call(litellm_params: Mapping[str, object]) -> str | None:
+    """
+    The provider the router hands a deployment's generic SDK call, or None when it cannot be resolved.
+
+    A model that carries its own provider prefix keeps that prefix even where get_llm_provider
+    would resolve it to a sibling provider (azure_ai/<openai model> on an Azure OpenAI host
+    resolves to azure): the SDK call still receives the prefixed model, and an explicit provider
+    that contradicts the prefix makes get_llm_provider re-prefix it into a deployment name that
+    does not exist upstream.
+    """
+    declared: Final = litellm_params.get("custom_llm_provider")
+    if isinstance(declared, str) and declared:
+        return declared
+    model: Final = litellm_params.get("model")
+    if not isinstance(model, str) or not model:
+        return None
+    prefix: Final = model.split("/", 1)[0]
+    if "/" in model and prefix in litellm.provider_list:
+        return prefix
+    try:
+        _, inferred, _, _ = get_llm_provider(model=model)
+    except BadRequestError:
+        return None
+    return inferred
+
+
 def warn_on_provider_credential_mismatch(model_name: str, litellm_params: Mapping[str, object]) -> str | None:
     """
     Warn when a deployment carries one provider's credentials but resolves to another.
diff --git a/litellm/router_utils/health_state_cache.py b/litellm/router_utils/health_state_cache.py
index 22d816e13e9..c8ca7105392 100644
--- a/litellm/router_utils/health_state_cache.py
+++ b/litellm/router_utils/health_state_cache.py
@@ -12,6 +12,7 @@ from typing_extensions import TypedDict
 
 from litellm import verbose_logger
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 
 if TYPE_CHECKING:
     from opentelemetry.trace import Span as _Span
@@ -27,6 +28,16 @@ class DeploymentHealthStateValue(TypedDict):
     reason: str
 
 
+def _read_shared_health_snapshot(cache: DualCache, key: str) -> object:
+    redis_cache: Final = cache.redis_cache
+    if redis_cache is None:
+        return None
+    try:
+        return redis_cache.get_cache(key)
+    except RedisCircuitBreakerOpenError:
+        return None
+
+
 class DeploymentHealthCache:
     """
     Cache for deployment health states produced by background health checks.
@@ -50,13 +61,12 @@ class DeploymentHealthCache:
         coexist on the one shared entry without erasing each other's results.
         The snapshot is read from Redis when available, since a pod-local read
         would only ever see this writer's own previous merge. When the Redis
-        read comes back empty (a miss, or a swallowed connection error), the
-        pod-local copy of the last merge is used so peers are not erased.
+        read comes back empty (a miss, a swallowed connection error, or a read
+        refused by the open circuit breaker), the pod-local copy of the last
+        merge is used so peers are not erased.
         """
         try:
-            redis_raw: Final = (
-                self.cache.redis_cache.get_cache(self.CACHE_KEY) if self.cache.redis_cache is not None else None
-            )
+            redis_raw: Final = _read_shared_health_snapshot(self.cache, self.CACHE_KEY)
             raw: Final = redis_raw if isinstance(redis_raw, dict) else self.cache.get_cache(key=self.CACHE_KEY)
             existing: Final = raw if isinstance(raw, dict) else {}
             expiry_seconds: Final = self.staleness_threshold * 1.5
diff --git a/litellm/router_utils/pre_call_checks/encrypted_content_affinity_check.py b/litellm/router_utils/pre_call_checks/encrypted_content_affinity_check.py
index b623e31ce06..cdd70e6baf2 100644
--- a/litellm/router_utils/pre_call_checks/encrypted_content_affinity_check.py
+++ b/litellm/router_utils/pre_call_checks/encrypted_content_affinity_check.py
@@ -37,17 +37,21 @@ Safe to enable globally:
 """
 
 import time
+from collections.abc import Iterator, Mapping
 from typing import TYPE_CHECKING, Final, Optional, Protocol, cast
 
 import httpx
 
 from litellm._logging import verbose_router_logger
 from litellm.exceptions import (
-    BadRequestError,
     RateLimitError,
     ServiceUnavailableError,
 )
 from litellm.integrations.custom_logger import CustomLogger, Span
+from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    encrypted_content_of_block,
+    strip_encrypted_reasoning_from_messages,
+)
 from litellm.responses.utils import ResponsesAPIRequestUtils
 from litellm.router_utils.cooldown_cache import CooldownCacheValue
 from litellm.types.llms.openai import AllMessageValues
@@ -138,15 +142,48 @@ class EncryptedContentAffinityCheck(CustomLogger):
             # If no encoded ID, check if encrypted_content itself is wrapped
             encrypted_content = item.get("encrypted_content")
             if encrypted_content and isinstance(encrypted_content, str):
-                (
-                    model_id,
-                    _,
-                ) = ResponsesAPIRequestUtils._unwrap_encrypted_content_with_model_id(encrypted_content)
+                model_id = EncryptedContentAffinityCheck._model_id_from_wrapped_encrypted_content(encrypted_content)
                 if model_id:
                     return model_id
 
         return None
 
+    @staticmethod
+    def _anthropic_content_blocks(messages: object) -> Iterator[Mapping[str, object]]:
+        if not isinstance(messages, list):
+            return iter(())
+        return (
+            cast(Mapping[str, object], block)  # cast-ok: narrowed by isinstance
+            for message in cast(list[object], messages)  # cast-ok: narrowed by isinstance
+            if isinstance(message, Mapping)
+            for content in (cast(Mapping[str, object], message).get("content"),)  # cast-ok: narrowed by isinstance
+            if isinstance(content, list)
+            for block in cast(list[object], content)  # cast-ok: narrowed by isinstance
+            if isinstance(block, Mapping)
+        )
+
+    @staticmethod
+    def _model_id_from_wrapped_encrypted_content(encrypted_content: str) -> str | None:
+        model_id, _ = ResponsesAPIRequestUtils._unwrap_encrypted_content_with_model_id(encrypted_content)
+        return model_id or None
+
+    @staticmethod
+    def _extract_model_id_from_anthropic_messages(messages: object) -> str | None:
+        return next(
+            (
+                model_id
+                for block in EncryptedContentAffinityCheck._anthropic_content_blocks(messages)
+                if (encrypted_content := encrypted_content_of_block(block)) is not None
+                if (
+                    model_id := EncryptedContentAffinityCheck._model_id_from_wrapped_encrypted_content(
+                        encrypted_content
+                    )
+                )
+                is not None
+            ),
+            None,
+        )
+
     @staticmethod
     def _find_deployment_by_model_id(healthy_deployments: list[dict], model_id: str) -> dict | None:
         for deployment in healthy_deployments:
@@ -158,6 +195,23 @@ class EncryptedContentAffinityCheck(CustomLogger):
                 return deployment
         return None
 
+    @staticmethod
+    def _request_team_id(request_kwargs: Mapping[str, object]) -> str | None:
+        containers: Final = (request_kwargs.get("metadata"), request_kwargs.get("litellm_metadata"))
+        team_ids: Final = (c.get("user_api_key_team_id") for c in containers if isinstance(c, Mapping))
+        return next((tid for tid in team_ids if isinstance(tid, str)), None)
+
+    def _routed_group_candidate_model_ids(self, request_kwargs: Mapping[str, object], model: str) -> frozenset[str]:
+        """
+        Deployment ids that could serve this turn's routed ``model``, as the router
+        resolves a route (model_group_alias / routing group / model_name / team /
+        pattern). Delegates to the router so the full precedence is not re-derived here
+        and no deployment ids are written into request kwargs bound for the provider.
+        """
+        if self.router is None:
+            return frozenset()
+        return self.router.get_candidate_model_ids_for_route(model=model, team_id=self._request_team_id(request_kwargs))
+
     @staticmethod
     def _encryption_boundary_key(
         litellm_params: object,
@@ -223,12 +277,17 @@ class EncryptedContentAffinityCheck(CustomLogger):
         parent_otel_span: Span | None = None,
     ) -> list[dict]:
         """
-        If the request ``input`` contains litellm-encoded item IDs, decode the
-        embedded ``model_id`` and pin the request to that deployment. Raises
-        ``RateLimitError`` / ``ServiceUnavailableError`` / ``BadRequestError``
-        when the originating deployment is unavailable and no encryption-boundary
-        peer exists, rather than dispatching a doomed request to a non-peer
-        deployment. The 429/503 split mirrors the originating cooldown's status:
+        If the request ``input`` contains litellm-encoded item IDs, or its Anthropic
+        ``messages`` replay a bridge-tagged thinking block, decode the embedded
+        ``model_id`` and pin the request to that deployment. Raises
+        ``RateLimitError`` / ``ServiceUnavailableError`` when the originating
+        deployment is a member of the routed model group but currently unavailable
+        and no encryption-boundary peer exists, rather than dispatching a doomed
+        request to a non-peer deployment. When the origin is not a member of the
+        routed group (an auto-router tier change, a model switch with no peer, a
+        removed deployment, or an unknown/forged marker), the encrypted reasoning is
+        stripped and the request dispatches with its readable history instead. The
+        429/503 split mirrors the originating cooldown's status:
         a 429-induced cooldown surfaces as 429 (with ``Retry-After`` set to the
         remaining cooldown window) so OpenAI-compatible clients back off and
         retry after the deployment is eligible again.
@@ -249,12 +308,15 @@ class EncryptedContentAffinityCheck(CustomLogger):
             request_kwargs["litellm_metadata"]["encrypted_content_affinity_enabled"] = True
 
         request_input: Final = request_kwargs.get("input")
-        model_id: Final = self._extract_model_id_from_input(request_input)
+        anthropic_messages: Final = messages or request_kwargs.get("messages")
+        model_id: Final = self._extract_model_id_from_input(
+            request_input
+        ) or self._extract_model_id_from_anthropic_messages(anthropic_messages)
         if not model_id:
             return typed_healthy_deployments
 
         verbose_router_logger.debug(
-            "EncryptedContentAffinityCheck: decoded model_id=%s from input item IDs",
+            "EncryptedContentAffinityCheck: decoded model_id=%s from the request's encrypted content markers",
             model_id,
         )
 
@@ -285,12 +347,35 @@ class EncryptedContentAffinityCheck(CustomLogger):
             request_kwargs["_encrypted_content_affinity_pinned"] = True
             return boundary_matches
 
-        # Dispatching to a non-peer would guarantee an upstream
-        # `invalid_encrypted_content` 400, so fail fast with a clearer error.
+        # The origin cannot serve this turn's routed group and no peer shares the boundary, so its
+        # encrypted reasoning can never decrypt here. Strip it, keep the readable history, and dispatch
+        # to the routed group instead of failing. Membership is tested by deployment id against the set
+        # the router actually resolved for this route, not by model-group name, so an alias, a
+        # provider-qualified spelling, a team-public name, or a pattern route of the same group is not
+        # mistaken for a tier change. An unknown origin (a removed deployment, or a forged marker) is
+        # treated the same as a cross-group one, which also denies an authenticated caller a
+        # deployment-id existence oracle: a real cross-group id and a nonexistent id both strip and
+        # dispatch rather than returning distinguishable responses. Only a genuine same-group member
+        # that is currently unavailable falls through to the fail-fast, preserving the cooldown contract.
+        routed_group_model_ids: Final = (
+            self._routed_group_candidate_model_ids(request_kwargs, model) if originating is not None else frozenset()
+        )
+        if str(model_id) not in routed_group_model_ids:
+            verbose_router_logger.debug(
+                "EncryptedContentAffinityCheck: model_id=%s is not a candidate for the routed group %s; "
+                "forwarding without its encrypted reasoning",
+                model_id,
+                model,
+            )
+            ResponsesAPIRequestUtils.strip_encrypted_reasoning_from_input(request_input)
+            strip_encrypted_reasoning_from_messages(anthropic_messages)
+            return typed_healthy_deployments
+
+        # The origin is a member of the routed group but currently unavailable (cooled down); fail fast
+        # rather than dispatching to a non-peer, which would guarantee an upstream 400.
         raise await self._unavailable_origin_error(
             model=model,
             model_id=model_id,
-            originating=originating,
             parent_otel_span=parent_otel_span,
         )
 
@@ -298,25 +383,11 @@ class EncryptedContentAffinityCheck(CustomLogger):
         self,
         model: str,
         model_id: str,
-        originating: Deployment | None,
         parent_otel_span: Span | None,
     ) -> Exception:
         # Public error messages intentionally omit the originating ``model_id`` so
         # an authenticated caller forging encrypted-content markers cannot use the
         # error surface to enumerate which deployment IDs exist on this router.
-        if originating is None:
-            return BadRequestError(
-                message=(
-                    "The deployment that produced this encrypted_content is no "
-                    "longer configured on this router, and no deployment on the "
-                    "same encryption boundary is available. Re-issue the request "
-                    "without the stale encrypted_content items, or restore the "
-                    "originating deployment."
-                ),
-                model=model,
-                llm_provider="",
-            )
-
         cooldown: Final = await self._get_origin_cooldown(model_id=model_id, parent_otel_span=parent_otel_span)
 
         if cooldown is not None and str(cooldown.get("status_code")) == "429":
diff --git a/litellm/router_utils/pre_call_checks/io_token_rate_limit_check.py b/litellm/router_utils/pre_call_checks/io_token_rate_limit_check.py
index 01d42627001..fbd3e18e357 100644
--- a/litellm/router_utils/pre_call_checks/io_token_rate_limit_check.py
+++ b/litellm/router_utils/pre_call_checks/io_token_rate_limit_check.py
@@ -21,6 +21,7 @@ import litellm
 from litellm import token_counter
 from litellm._logging import verbose_router_logger
 from litellm.caching.dual_cache import DualCache
+from litellm.litellm_core_utils.token_counter import offload_token_count
 from litellm.types.router import RouterCacheEnum, RouterErrors
 from litellm.utils import get_utc_datetime
 
@@ -466,7 +467,7 @@ async def async_io_token_pre_call_check(
 
     request_kwargs: Final = get_io_token_rate_limit_request_kwargs()
     _model: Final = (deployment.get("litellm_params") or {}).get("model") or ""
-    estimated_input: Final = _estimate_input_tokens(request_kwargs, model=_model)
+    estimated_input: Final = await offload_token_count(_estimate_input_tokens)(request_kwargs, model=_model)
     max_tokens: Final = _resolve_max_tokens(request_kwargs, deployment)
 
     dt: Final = get_utc_datetime()
diff --git a/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py b/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py
index 70362e60495..0589e290b47 100644
--- a/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py
+++ b/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py
@@ -14,6 +14,7 @@ from litellm.integrations.anthropic_cache_control_hook import (
     AnthropicCacheControlHook,
 )
 from litellm.integrations.custom_logger import CustomLogger, Span
+from litellm.litellm_core_utils.token_counter import offload_token_count
 from litellm.types.llms.openai import AllMessageValues
 from litellm.types.utils import CallTypes, StandardLoggingPayload
 from litellm.utils import get_prompt_cache_min_tokens, is_prompt_caching_valid_prompt
@@ -61,7 +62,7 @@ class PromptCachingDeploymentCheck(CustomLogger):
         if request_kwargs is not None and request_kwargs.get("_target_order") is not None:
             return healthy_deployments
 
-        if messages is not None and is_prompt_caching_valid_prompt(
+        if messages is not None and await offload_token_count(is_prompt_caching_valid_prompt)(
             messages=messages,
             model=model,
             min_token_count=_get_min_token_count_for_deployments(healthy_deployments),
@@ -139,7 +140,7 @@ class PromptCachingDeploymentCheck(CustomLogger):
             return
 
         ## PROMPT CACHING - cache model id, if prompt caching valid prompt + provider
-        if is_prompt_caching_valid_prompt(
+        if await offload_token_count(is_prompt_caching_valid_prompt)(
             model=model,
             messages=cast(list[AllMessageValues], messages),
         ):
diff --git a/litellm/rust_bridge/token_counter.py b/litellm/rust_bridge/token_counter.py
new file mode 100644
index 00000000000..ee755b317d8
--- /dev/null
+++ b/litellm/rust_bridge/token_counter.py
@@ -0,0 +1,79 @@
+"""Thin Python wrapper for the native Rust input token counter."""
+
+from __future__ import annotations
+
+from collections.abc import Awaitable
+from dataclasses import dataclass
+from functools import lru_cache
+from typing import Final, Protocol, cast  # noqa: TID251  # native extension exposes dynamically typed callables
+
+from pydantic import TypeAdapter
+
+import litellm
+from litellm._logging import verbose_logger
+from litellm.rust_bridge.bindings import NativeBinding
+from litellm.rust_bridge.configuration import rust_enabled
+from litellm.rust_bridge.runtime import BridgeErrorContext, RustHandled, aattempt
+from litellm.utils import claude_json_str
+from litellm.utils import uses_anthropic_tokenizer as _python_uses_anthropic_tokenizer
+
+
+class RustTokenCounter(Protocol):
+    def acount_request(self, body: bytes) -> Awaitable[object]:
+        raise NotImplementedError
+
+
+class RustTokenCounterFactory(Protocol):
+    def __call__(self, tokenizer_json: str) -> RustTokenCounter:
+        raise NotImplementedError
+
+
+@dataclass(frozen=True, slots=True)
+class InputTokenCount:
+    model: str | None
+    input_tokens: int
+
+
+_INPUT_TOKEN_COUNT: Final = TypeAdapter(InputTokenCount)
+
+
+def _as_factory(value: object) -> RustTokenCounterFactory | None:
+    return (
+        cast(  # cast-ok: native extension protocol is runtime-defined
+            RustTokenCounterFactory, value
+        )
+        if callable(value)
+        else None
+    )
+
+
+TOKEN_COUNTER: Final = NativeBinding("TokenCounter", validate=_as_factory)
+
+
+def uses_anthropic_tokenizer(model: str) -> bool:
+    if litellm.disable_token_counter is True or litellm.disable_hf_tokenizer_download is True:
+        return False
+    return _python_uses_anthropic_tokenizer(model)
+
+
+@lru_cache(maxsize=4)
+def _anthropic_counter(factory: RustTokenCounterFactory) -> RustTokenCounter:
+    return factory(claude_json_str)
+
+
+async def count_anthropic_input_tokens(body: bytes) -> InputTokenCount | None:
+    if not rust_enabled():
+        return None
+    factory: Final = TOKEN_COUNTER.load()
+    if factory is None:
+        return None
+    try:
+        attempt: Final = await aattempt(
+            native_call=lambda: _anthropic_counter(factory).acount_request(body),
+            adapt=_INPUT_TOKEN_COUNT.validate_python,
+            context=BridgeErrorContext(route="token_counter", provider="anthropic", model=""),
+        )
+    except (RuntimeError, ValueError) as error:
+        verbose_logger.debug("Rust token counter failed, counting in Python: %s", error)
+        return None
+    return attempt.value if isinstance(attempt, RustHandled) else None
diff --git a/litellm/types/integrations/newrelic.py b/litellm/types/integrations/newrelic.py
index 36e4d02c2a8..b5905ad0b93 100644
--- a/litellm/types/integrations/newrelic.py
+++ b/litellm/types/integrations/newrelic.py
@@ -27,9 +27,9 @@ NEWRELIC_METRIC_ENDPOINT_BY_REGION: Final[Mapping[str, str]] = MappingProxyType(
 NEWRELIC_DEFAULT_REGION: Final = "us"
 
 #: Metric API caps a payload at 2000 data points / 1MB compressed; each queued
-#: record expands to at most 6 metrics, so cap the per-flush record count well
-#: below that.
-NEWRELIC_METRICS_MAX_BATCH_SIZE: Final = 250
+#: record expands to at most 6 bucket metrics plus 2 team budget gauges (8), so cap
+#: the per-flush record count well below 2000 / 8.
+NEWRELIC_METRICS_MAX_BATCH_SIZE: Final = 200
 
 #: Hard cap on records retained across failed flushes (5xx/network requeue).
 #: Beyond this the oldest records are dropped.
@@ -48,6 +48,8 @@ NEWRELIC_METRIC_PROMPT_TOKENS: Final = "litellm.tokens.prompt"
 NEWRELIC_METRIC_COMPLETION_TOKENS: Final = "litellm.tokens.completion"
 NEWRELIC_METRIC_TOTAL_TOKENS: Final = "litellm.tokens.total"
 NEWRELIC_METRIC_REQUEST_DURATION_MS: Final = "litellm.request.duration_ms"
+NEWRELIC_METRIC_TEAM_MAX_BUDGET: Final = "litellm.team.max_budget"
+NEWRELIC_METRIC_TEAM_REMAINING_BUDGET: Final = "litellm.team.remaining_budget"
 
 
 class NewRelicSummaryValue(TypedDict):
@@ -66,6 +68,13 @@ class NewRelicCountMetric(TypedDict):
     attributes: ReadOnly[Mapping[str, str]]
 
 
+class NewRelicGaugeMetric(TypedDict):
+    name: ReadOnly[str]
+    type: ReadOnly[Literal["gauge"]]
+    value: ReadOnly[float]
+    attributes: ReadOnly[Mapping[str, str]]
+
+
 class NewRelicSummaryMetric(TypedDict):
     name: ReadOnly[str]
     type: ReadOnly[Literal["summary"]]
@@ -73,7 +82,7 @@ class NewRelicSummaryMetric(TypedDict):
     attributes: ReadOnly[Mapping[str, str]]
 
 
-NewRelicMetric = NewRelicCountMetric | NewRelicSummaryMetric
+NewRelicMetric = NewRelicCountMetric | NewRelicGaugeMetric | NewRelicSummaryMetric
 
 
 #: ``interval.ms`` has a dot in it, so the functional TypedDict form is required.
@@ -108,6 +117,8 @@ class NewRelicMetricRecord:
     completion_tokens: int
     total_tokens: int
     duration_ms: float
+    team_max_budget: float | None = None
+    team_spend: float | None = None
 
     @property
     def bucket_key(self) -> tuple[str, str, str, str, str, str]:
diff --git a/litellm/types/integrations/pointfive.py b/litellm/types/integrations/pointfive.py
new file mode 100644
index 00000000000..9ff17393ecd
--- /dev/null
+++ b/litellm/types/integrations/pointfive.py
@@ -0,0 +1,45 @@
+from dataclasses import dataclass
+from typing import Final
+
+from pydantic import Field
+
+from litellm.types.integrations.custom_logger import StandardCustomLoggerInitParams
+
+RETRYABLE_UPLOAD_STATUS_CODES: Final = frozenset({429, 500, 502, 503, 504})
+
+DEFAULT_API_URL: Final = "https://api.pointfive.co/api/v1/ingestion"
+
+
+class PointFiveInitParams(StandardCustomLoggerInitParams):
+    """
+    Params for initializing a PointFive logger on litellm.
+
+    Defaults trade freshness for fewer, larger uploads: every flush becomes one object, so
+    the interval is minutes rather than seconds. ``batch_size`` also bounds how much a busy
+    proxy holds in memory between flushes, so it stays modest. ``max_batch_bytes`` bounds
+    how much a single object may hold, which matters most when message logging is left on,
+    since an unredacted payload is orders of magnitude larger than a redacted one.
+    """
+
+    api_key: str | None = None
+    api_url: str | None = None
+    batch_size: int = Field(default=1_000, gt=0)
+    flush_interval: int = Field(default=300, gt=0)
+    max_batch_bytes: int = Field(default=8 * 1024 * 1024, gt=0)
+    max_upload_retries: int = Field(default=3, ge=1)
+
+
+@dataclass(frozen=True, slots=True)
+class PointFiveUploadTarget:
+    """A single-use presigned destination for one batch, issued by the PointFive API."""
+
+    upload_url: str
+    object_key: str
+
+
+@dataclass(frozen=True, slots=True)
+class PointFiveUploadFailure:
+    """Why a batch could not be uploaded, and whether a later attempt could still succeed."""
+
+    detail: str
+    retryable: bool
diff --git a/litellm/types/integrations/prometheus.py b/litellm/types/integrations/prometheus.py
index 8498b6f6d00..a024581f600 100644
--- a/litellm/types/integrations/prometheus.py
+++ b/litellm/types/integrations/prometheus.py
@@ -154,6 +154,22 @@ LATENCY_BUCKETS: Final = (
     float("inf"),
 )
 
+UNKNOWN_INPUT_SEQUENCE_LENGTH: Final = "unknown"
+INPUT_SEQUENCE_LENGTH_BUCKETS: Final = (
+    (1_000, "0-1k"),
+    (4_000, "1k-4k"),
+    (16_000, "4k-16k"),
+    (64_000, "16k-64k"),
+    (float("inf"), "64k+"),
+)
+
+
+def get_input_sequence_length_bucket(prompt_tokens: object) -> str:
+    if not isinstance(prompt_tokens, int) or isinstance(prompt_tokens, bool) or prompt_tokens < 0:
+        return UNKNOWN_INPUT_SEQUENCE_LENGTH
+    return next(label for upper, label in INPUT_SEQUENCE_LENGTH_BUCKETS if prompt_tokens < upper)
+
+
 # Batch jobs can run for minutes to hours; buckets span 1 min → 24 h.
 BATCH_DURATION_BUCKETS: Final = (
     60.0,
@@ -205,6 +221,7 @@ class UserAPIKeyLabelNames(Enum):
     MCP_TOOL_NAME = "mcp_tool_name"
     MCP_SERVER_NAME = "mcp_server_name"
     SERVICE_TIER = "service_tier"
+    INPUT_SEQUENCE_LENGTH = "input_sequence_length"
 
 
 DEFINED_PROMETHEUS_METRICS = Literal[
@@ -857,6 +874,13 @@ class PrometheusMetricLabels:
             "litellm_images_generated_metric",
         }
     )
+    _input_sequence_length_metrics: ClassVar[frozenset[str]] = frozenset(
+        {
+            "litellm_llm_api_latency_metric",
+            "litellm_llm_api_time_to_first_token_metric",
+            "litellm_request_total_latency_metric",
+        }
+    )
     # Managed batch metrics
     _batch_user_labels = [
         UserAPIKeyLabelNames.v1_LITELLM_MODEL_NAME.value,
@@ -955,14 +979,23 @@ class PrometheusMetricLabels:
                     custom_labels.append(label)
 
         if label_name in PrometheusMetricLabels._org_label_metrics:
-            for label in [
+            for label in (
                 UserAPIKeyLabelNames.ORG_ID.value,
                 UserAPIKeyLabelNames.ORG_ALIAS.value,
-            ]:
+            ):
                 if label not in default_labels and label not in custom_labels:
                     custom_labels.append(label)
 
-        return default_labels + custom_labels
+        input_sequence_length_labels: Final = (
+            (UserAPIKeyLabelNames.INPUT_SEQUENCE_LENGTH.value,)
+            if (
+                label_name in PrometheusMetricLabels._input_sequence_length_metrics
+                and litellm.prometheus_emit_input_sequence_length_label is True
+                and UserAPIKeyLabelNames.INPUT_SEQUENCE_LENGTH.value not in custom_labels
+            )
+            else ()
+        )
+        return [*default_labels, *custom_labels, *input_sequence_length_labels]
 
 
 _USER_API_KEY_LABEL_VALUE_INIT_ALIASES: Final[Mapping[str, str]] = MappingProxyType(
@@ -1015,6 +1048,7 @@ class UserAPIKeyLabelValues:
     mcp_tool_name: str | None = None
     mcp_server_name: str | None = None
     service_tier: str | None = None
+    input_sequence_length: str | None = None
 
     # Added for test compatibility.
     def __init__(self, **kwargs: Any) -> None:
diff --git a/litellm/types/llms/bedrock.py b/litellm/types/llms/bedrock.py
index 9f93886a9c6..76756ac35bb 100644
--- a/litellm/types/llms/bedrock.py
+++ b/litellm/types/llms/bedrock.py
@@ -1107,6 +1107,11 @@ class BedrockTag(TypedDict):
     value: str
 
 
+class AwsSessionTag(TypedDict):
+    Key: str  # writable-ok: boto3's STS stubs type assume_role Tags as writable TagTypeDef, which rejects ReadOnly
+    Value: str  # writable-ok: boto3's STS stubs type assume_role Tags as writable TagTypeDef, which rejects ReadOnly
+
+
 class BedrockCreateBatchRequest(TypedDict, total=False):
     """
     Request structure for creating a Bedrock batch inference job.
diff --git a/litellm/types/llms/databricks.py b/litellm/types/llms/databricks.py
index e87a684aab8..a9c027bd2de 100644
--- a/litellm/types/llms/databricks.py
+++ b/litellm/types/llms/databricks.py
@@ -2,6 +2,7 @@ from typing import Any, Literal
 
 from pydantic import BaseModel
 from typing_extensions import (
+    ReadOnly,
     Required,
     TypedDict,
 )
@@ -57,6 +58,14 @@ class DatabricksMessage(TypedDict, total=False):
     role: Required[str]
     content: Required[AllDatabricksContentValues]
     tool_calls: list[DatabricksTool] | None
+    reasoning_content: ReadOnly[str | None]
+    reasoning: ReadOnly[str | None]
+
+
+class DatabricksDelta(TypedDict, total=False):
+    role: ReadOnly[str]
+    content: ReadOnly[AllDatabricksContentValues | None]
+    reasoning_content: ReadOnly[str | None]
 
 
 class DatabricksChoice(TypedDict, total=False):
diff --git a/litellm/types/llms/openai.py b/litellm/types/llms/openai.py
index b6da9490e01..b7c4371f32f 100644
--- a/litellm/types/llms/openai.py
+++ b/litellm/types/llms/openai.py
@@ -1564,6 +1564,9 @@ class ResponseIncompleteEvent(BaseLiteLLMOpenAIResponseObject):
     response: ResponsesAPIResponse
 
 
+ResponsesTerminalEvent: TypeAlias = ResponseCompletedEvent | ResponseIncompleteEvent | ResponseFailedEvent
+
+
 class ResponsePartAddedEvent(BaseLiteLLMOpenAIResponseObject):
     type: Literal[ResponsesAPIStreamEvents.RESPONSE_PART_ADDED]
     item_id: str
diff --git a/litellm/types/management_endpoints/cache_settings_endpoints.py b/litellm/types/management_endpoints/cache_settings_endpoints.py
index 32b32991449..cb05f3a50ac 100644
--- a/litellm/types/management_endpoints/cache_settings_endpoints.py
+++ b/litellm/types/management_endpoints/cache_settings_endpoints.py
@@ -237,4 +237,49 @@ CACHE_SETTINGS_FIELDS: Final[list[CacheSettingsField]] = [
         ui_field_name="SSL Check Hostname",
         redis_type=None,
     ),
+    CacheSettingsField(
+        field_name="aws_iam_auth",
+        field_type="Boolean",
+        field_value=None,
+        field_description="Enable AWS ElastiCache IAM authentication",
+        field_default=False,
+        ui_field_name="AWS IAM Authentication",
+        redis_type=None,
+    ),
+    CacheSettingsField(
+        field_name="aws_iam_user_name",
+        field_type="String",
+        field_value=None,
+        field_description="AWS ElastiCache IAM user name",
+        field_default=None,
+        ui_field_name="AWS IAM User Name",
+        redis_type=None,
+    ),
+    CacheSettingsField(
+        field_name="aws_iam_cache_name",
+        field_type="String",
+        field_value=None,
+        field_description="AWS ElastiCache cache name",
+        field_default=None,
+        ui_field_name="AWS IAM Cache Name",
+        redis_type=None,
+    ),
+    CacheSettingsField(
+        field_name="aws_iam_region",
+        field_type="String",
+        field_value=None,
+        field_description="AWS region for ElastiCache IAM authentication",
+        field_default=None,
+        ui_field_name="AWS IAM Region",
+        redis_type=None,
+    ),
+    CacheSettingsField(
+        field_name="aws_iam_serverless",
+        field_type="Boolean",
+        field_value=None,
+        field_description="The ElastiCache cache is serverless rather than a self-designed cluster",
+        field_default=False,
+        ui_field_name="AWS IAM Serverless Cache",
+        redis_type=None,
+    ),
 ]
diff --git a/litellm/types/management_endpoints/coordination_redis_endpoints.py b/litellm/types/management_endpoints/coordination_redis_endpoints.py
index 30033346ed7..d70a921a22f 100644
--- a/litellm/types/management_endpoints/coordination_redis_endpoints.py
+++ b/litellm/types/management_endpoints/coordination_redis_endpoints.py
@@ -102,4 +102,41 @@ COORDINATION_REDIS_SETTINGS_FIELDS: Final[list[CoordinationRedisSettingsField]]
         ui_field_name="Service Name",
         section="sentinel",
     ),
+    CoordinationRedisSettingsField(
+        field_name="aws_iam_auth",
+        field_type="Boolean",
+        field_description="Enable AWS ElastiCache IAM authentication",
+        field_default=False,
+        ui_field_name="AWS IAM Authentication",
+        section="connection",
+    ),
+    CoordinationRedisSettingsField(
+        field_name="aws_iam_user_name",
+        field_type="String",
+        field_description="AWS ElastiCache IAM user name",
+        ui_field_name="AWS IAM User Name",
+        section="connection",
+    ),
+    CoordinationRedisSettingsField(
+        field_name="aws_iam_cache_name",
+        field_type="String",
+        field_description="AWS ElastiCache cache name",
+        ui_field_name="AWS IAM Cache Name",
+        section="connection",
+    ),
+    CoordinationRedisSettingsField(
+        field_name="aws_iam_region",
+        field_type="String",
+        field_description="AWS region for ElastiCache IAM authentication",
+        ui_field_name="AWS IAM Region",
+        section="connection",
+    ),
+    CoordinationRedisSettingsField(
+        field_name="aws_iam_serverless",
+        field_type="Boolean",
+        field_description="The ElastiCache cache is serverless rather than a self-designed cluster",
+        field_default=False,
+        ui_field_name="AWS IAM Serverless Cache",
+        section="connection",
+    ),
 ]
diff --git a/litellm/types/mcp_server/mcp_server_manager.py b/litellm/types/mcp_server/mcp_server_manager.py
index 84ffd50eea1..58f9dadc1ce 100644
--- a/litellm/types/mcp_server/mcp_server_manager.py
+++ b/litellm/types/mcp_server/mcp_server_manager.py
@@ -1,7 +1,8 @@
 from datetime import datetime
 from typing import Any, Final, Literal
 
-from pydantic import BaseModel, ConfigDict, field_validator
+from pydantic import BaseModel, ConfigDict, Field, field_validator, model_validator
+from typing_extensions import Self
 
 from litellm.types.mcp import (
     DEFAULT_SUBJECT_TOKEN_TYPE,
@@ -38,6 +39,26 @@ class MCPOAuthMetadata(BaseModel):
     usable in memory but must never be persisted as configuration."""
 
 
+class MCPOAuthIdentityBinding(BaseModel):
+    """Per-server policy binding stored per-user OAuth credentials to the authenticated LiteLLM caller.
+
+    When enabled for an interactive oauth2 server, the token relay validates the upstream OIDC
+    ``id_token`` (signature via the pinned issuer's JWKS, issuer, audience, expiry, nonce) and compares its
+    principal claim to the LiteLLM caller's trusted identity before the token is returned, stored,
+    or cached. ``audit`` logs mismatches without changing behavior; ``enforce`` fails closed with
+    403 ``oauth_principal_mismatch`` and disables the direct ``oauth-user-credential`` POST, which
+    would otherwise bypass validation with an arbitrary opaque token.
+    """
+
+    mode: Literal["disabled", "audit", "enforce"] = "disabled"
+    issuer: str
+    jwks_url: str | None = None
+    audiences: list[str] = Field(min_length=1)  # mutable-ok: public Pydantic schema requires list values
+    principal_claim: str = "email"
+    caller_field: Literal["user_email", "user_id"] = "user_email"
+    require_email_verified: bool = True
+
+
 class MCPServer(BaseModel):
     server_id: str
     name: str
@@ -173,6 +194,7 @@ class MCPServer(BaseModel):
     # response (supports dot-notation for nested fields, e.g. "team.enterprise_id").
     # Tokens that fail validation are rejected before storage.
     token_validation: dict[str, Any] | None = None
+    oauth_identity_binding: MCPOAuthIdentityBinding | None = None
     # Optional TTL override (seconds) for the Redis per-user token cache, capped
     # at the token's expires_in minus the expiry buffer so a cached entry never
     # outlives the token. Defaults to the token's expires_in minus the expiry
@@ -225,6 +247,14 @@ class MCPServer(BaseModel):
         """
         return self.oauth2_flow == "client_credentials"
 
+    @model_validator(mode="after")
+    def validate_identity_binding_mode(self) -> Self:
+        binding: Final = self.oauth_identity_binding
+        if binding is not None and binding.mode != "disabled":
+            if not self.needs_user_oauth_token or self.delegate_auth_to_upstream:
+                raise ValueError("oauth_identity_binding requires gateway-managed per-user OAuth2 credentials")
+        return self
+
     @property
     def needs_user_oauth_token(self) -> bool:
         """True if this is an OAuth2 server that relies on per-user tokens (no client_credentials)."""
@@ -250,7 +280,23 @@ class MCPServer(BaseModel):
     @property
     def advertises_gateway_authorization_server(self) -> bool:
         """Whether named discovery should advertise the aggregate gateway authorization server."""
-        return self.is_gateway_managed_oauth2 and not self.uses_per_server_oauth_relay
+        if self.auth_type == MCPAuth.oauth2:
+            return self.is_gateway_managed_oauth2 and not self.uses_per_server_oauth_relay
+        if self.auth_type not in (
+            None,
+            MCPAuth.none,
+            MCPAuth.api_key,
+            MCPAuth.bearer_token,
+            MCPAuth.basic,
+            MCPAuth.authorization,
+            MCPAuth.token,
+            MCPAuth.aws_sigv4,
+        ):
+            return False
+        return not any(
+            header.lower() in ("authorization", "x-api-key", "api-key", "apikey")
+            for header in (self.extra_headers or ())
+        )
 
     @property
     def is_true_passthrough(self) -> bool:
diff --git a/litellm/types/object_permission.py b/litellm/types/object_permission.py
index 1b391a3a1ef..68661aed891 100644
--- a/litellm/types/object_permission.py
+++ b/litellm/types/object_permission.py
@@ -8,7 +8,7 @@ can adopt the type without violating the SDK-must-not-import-from-proxy
 layering rule.
 """
 
-from typing_extensions import TypedDict
+from typing_extensions import ReadOnly, TypedDict
 
 
 class ObjectPermissionDict(TypedDict, total=False):
@@ -23,3 +23,4 @@ class ObjectPermissionDict(TypedDict, total=False):
     models: list[str] | None
     search_tools: list[str] | None
     mcp_tool_search_enabled: bool | None
+    skills: ReadOnly[list[str] | None]
diff --git a/litellm/types/proxy/claude_code_endpoints.py b/litellm/types/proxy/claude_code_endpoints.py
index 2ee1bbbbb98..dcb5561cfeb 100644
--- a/litellm/types/proxy/claude_code_endpoints.py
+++ b/litellm/types/proxy/claude_code_endpoints.py
@@ -25,10 +25,12 @@ class PluginSpec(BaseModel):
     source: dict[str, str] = Field(
         ...,
         description=(
-            "Git source reference. Supported formats:\n"
+            "Plugin source reference. Supported formats:\n"
             "- GitHub: {'source': 'github', 'repo': 'org/repo'}\n"
             "- Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}\n"
-            "- Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}"
+            "- Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}\n"
+            "- Zip archive on any https host (e.g. S3): "
+            "{'source': 'archive', 'url': 'https://bucket.s3.amazonaws.com/plugin.zip', 'sha256': '<optional hex digest>'}"
         ),
     )
     version: str | None = Field("1.0.0", description="Semantic version")
@@ -46,7 +48,7 @@ class RegisterPluginRequest(PluginSpec):
     Request body for registering a plugin in the marketplace.
 
     LiteLLM acts as a registry/discovery layer. Plugins are hosted on
-    GitHub/GitLab/Bitbucket and referenced by their git source.
+    GitHub/GitLab/Bitbucket or as a zip archive on any https host and referenced by their source.
     """
 
     name: str = Field(
@@ -76,7 +78,7 @@ class PluginResponse(BaseModel):
     name: str = Field(..., description="Plugin name")
     version: str | None = Field(None, description="Plugin version")
     description: str | None = Field(None, description="Plugin description")
-    source: dict[str, str] = Field(..., description="Git source reference")
+    source: dict[str, str] = Field(..., description="Plugin source reference")
     enabled: bool = Field(..., description="Whether plugin is enabled")
 
 
diff --git a/litellm/types/router.py b/litellm/types/router.py
index 5c9eab30f3d..fc09c40fe08 100644
--- a/litellm/types/router.py
+++ b/litellm/types/router.py
@@ -4,7 +4,7 @@ litellm.Router Types - includes RouterConfig, UpdateRouterConfig, ModelInfo etc
 
 import datetime
 import enum
-from collections.abc import Mapping
+from collections.abc import Mapping, Sequence
 from dataclasses import dataclass
 from typing import TYPE_CHECKING, Any, ClassVar, Final, Generic, Literal, TypeVar, get_type_hints
 
@@ -21,6 +21,7 @@ if TYPE_CHECKING:
 
 from .completion import CompletionRequest
 from .embedding import EmbeddingRequest
+from .llms.bedrock import AwsSessionTag
 from .llms.openai import OpenAIFileObject
 from .search import SearchProvider
 from .utils import (
@@ -288,6 +289,7 @@ class CredentialLiteLLMParams(BaseModel):
     aws_web_identity_token: str | None = None
     aws_sts_endpoint: str | None = None
     aws_external_id: str | None = None
+    aws_session_tags: Sequence[AwsSessionTag] | None = None
     aws_bedrock_runtime_endpoint: str | None = None
     aws_bedrock_project_id: str | None = None
     s3_bucket_name: str | None = None
@@ -525,6 +527,7 @@ class LiteLLMParamsTypedDict(TypedDict, total=False):
     input_cost_per_second: float | None
     output_cost_per_second: float | None
     output_cost_per_second_480p: ReadOnly[float | None]
+    output_cost_per_second_720p: ReadOnly[float | None]
     output_cost_per_second_1080p: float | None
     output_cost_per_second_4k: ReadOnly[float | None]
     num_retries: int | None
@@ -611,6 +614,24 @@ class Deployment(BaseModel):
         setattr(self, key, value)
 
 
+@dataclass(frozen=True, slots=True)
+class DeploymentModelListingInfo:
+    """What the deployments behind a model name contribute to its OpenAI-compatible listing entry.
+
+    ``cost_map_keys`` are the names those deployments' underlying models are known by in
+    ``litellm.model_cost`` (``base_model`` when set, else ``litellm_params.model``), which
+    is what a request actually reaches; the public model name they are listed under is an
+    arbitrary alias and often absent from the cost map. Keys are deduplicated in config
+    order, so the ordinary group -- several interchangeable deployments of one model --
+    carries exactly one. The token limits are the widest explicitly set in any
+    deployment's ``model_info``, which outrank anything the cost map says.
+    """
+
+    cost_map_keys: tuple[str, ...]
+    max_input_tokens: int | None
+    max_output_tokens: int | None
+
+
 class RouterErrors(enum.Enum):
     """
     Enum for router specific errors with common codes
diff --git a/litellm/types/utils.py b/litellm/types/utils.py
index d62f00f3676..58b940227f8 100644
--- a/litellm/types/utils.py
+++ b/litellm/types/utils.py
@@ -35,6 +35,7 @@ from pydantic import (
     BaseModel,
     ConfigDict,
     Field,
+    JsonValue,
     PrivateAttr,
     SkipValidation,
     field_serializer,
@@ -318,6 +319,7 @@ class ModelInfoBase(ProviderSpecificModelInfo, total=False):
         float | None
     )  # video_generation tier: key output_cost_per_second_<resolution> (e.g. 1080p, 720p)
     output_cost_per_second_480p: ReadOnly[float | None]
+    output_cost_per_second_720p: ReadOnly[float | None]
     output_cost_per_second_4k: ReadOnly[float | None]
     ocr_cost_per_page: float | None  # for OCR models
     ocr_cost_per_credit: float | None  # for OCR models priced by credit
@@ -3372,7 +3374,12 @@ class StandardAuditLogPayload(TypedDict):
     updated_values: str | None
 
 
-class StandardLoggingPayload(TypedDict):
+class ClassifierAudit(TypedDict, total=False):
+    classifier_input: ReadOnly[Mapping[str, JsonValue]]
+    originating_request_masked: ReadOnly[Mapping[str, JsonValue]]
+
+
+class StandardLoggingPayload(ClassifierAudit):
     id: str
     trace_id: str  # Trace multiple LLM calls belonging to same overall request (e.g. fallbacks/retries)
     session_id: str  # End-user/conversation session id (litellm_session_id), independent of trace_id
@@ -3522,6 +3529,7 @@ class CustomPricingLiteLLMParams(MirroredPricingParams):
     output_cost_per_second: float | None = None
     output_cost_per_second_1080p: float | None = None
     output_cost_per_second_480p: float | None = None
+    output_cost_per_second_720p: float | None = None
     output_cost_per_second_4k: float | None = None
     input_cost_per_pixel: float | None = None
     output_cost_per_pixel: float | None = None
diff --git a/litellm/utils.py b/litellm/utils.py
index 36b48d3b8d8..a765e1b1246 100644
--- a/litellm/utils.py
+++ b/litellm/utils.py
@@ -66,6 +66,7 @@ from litellm.constants import (
     DEFAULT_EMBEDDING_PARAM_VALUES,
     DEFAULT_MAX_LRU_CACHE_SIZE,
     DEFAULT_MINIMUM_PROMPT_CACHE_TOKEN_COUNT,
+    DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
     DEFAULT_REASONING_EFFORT_MEDIUM_THINKING_BUDGET,
     DEFAULT_TRIM_RATIO,
     FUNCTION_DEFINITION_TOKEN_COUNT,
@@ -278,7 +279,7 @@ except (ImportError, AttributeError, TypeError):
 # Convert to str (if necessary)
 claude_json_str = json.dumps(json_data)
 import importlib.metadata
-from collections.abc import Callable, Iterable, Mapping, Sequence
+from collections.abc import AsyncIterator, Callable, Iterable, Iterator, Mapping, Sequence
 from typing import TYPE_CHECKING, Any, Final, Literal, Optional, Union, cast, get_args
 
 from litellm import utils as litellm_utils
@@ -1195,6 +1196,47 @@ def function_setup(
         raise e
 
 
+def _dispatch_success_logging(
+    logging_obj: LiteLLMLoggingObject,
+    result: object,
+    start_time: datetime.datetime,
+    end_time: datetime.datetime,
+    is_completion_with_fallbacks: bool,
+    is_litellm_internal_call: bool,
+) -> None:
+    if not is_litellm_internal_call:
+        if getattr(logging_obj, "_defer_async_logging", False):
+
+            def _enqueue_deferred_logging() -> None:
+                asyncio.create_task(
+                    _client_async_logging_helper(
+                        logging_obj=logging_obj,
+                        result=result,
+                        start_time=start_time,
+                        end_time=end_time,
+                        is_completion_with_fallbacks=is_completion_with_fallbacks,
+                    )
+                )
+
+            logging_obj._enqueue_deferred_logging = _enqueue_deferred_logging
+        else:
+            asyncio.create_task(
+                _client_async_logging_helper(
+                    logging_obj=logging_obj,
+                    result=result,
+                    start_time=start_time,
+                    end_time=end_time,
+                    is_completion_with_fallbacks=is_completion_with_fallbacks,
+                )
+            )
+
+    logging_obj.handle_sync_success_callbacks_for_async_calls(
+        result=result,
+        start_time=start_time,
+        end_time=end_time,
+    )
+
+
 async def _client_async_logging_helper(
     logging_obj: LiteLLMLoggingObject,
     result,
@@ -1662,6 +1704,16 @@ def client(original_function):
                 kwargs=kwargs,
             )
 
+            _update_response_metadata: Final = getattr(sys.modules[__name__], "update_response_metadata")
+            _update_response_metadata(
+                result=result,
+                logging_obj=logging_obj,
+                model=model,
+                kwargs=kwargs,
+                start_time=start_time,
+                end_time=end_time,
+            )
+
             # LOG SUCCESS - handle streaming success logging in the _next_ object, remove `handle_success` once it's deprecated
             verbose_logger.info("Wrapper: Completed Call, calling success_handler")
             # Copy the current context to propagate it to the background thread
@@ -1676,15 +1728,6 @@ def client(original_function):
                 end_time,
             )
             # RETURN RESULT
-            update_response_metadata = getattr(sys.modules[__name__], "update_response_metadata")
-            update_response_metadata(
-                result=result,
-                logging_obj=logging_obj,
-                model=model,
-                kwargs=kwargs,
-                start_time=start_time,
-                end_time=end_time,
-            )
             return result
         except Exception as e:
             call_type = original_function.__name__
@@ -1843,6 +1886,9 @@ def client(original_function):
                 elif _caching_handler_response.embedding_all_elements_cache_hit is True:
                     return _caching_handler_response.final_embedding_cached_response
 
+            if _llm_caching_handler.preset_cache_key is not None:
+                logging_obj.litellm_params["preset_cache_key"] = _llm_caching_handler.preset_cache_key
+
             # CHECK MAX TOKENS
             if (
                 kwargs.get("max_tokens", None) is not None
@@ -1941,48 +1987,20 @@ def client(original_function):
                 args=args,
             )
 
-            # LOG SUCCESS - handle streaming success logging in the _next_ object
-            # Internal sub-calls (e.g. emulated file-search steps) share the
-            # parent's logging obj; skip async logging here so only the outer call bills once.
-            # NOTE: streaming requests return early (before this point) via
-            # CustomStreamWrapper, so this block is non-streaming only.
-            if not _is_litellm_internal_call:
-                if getattr(logging_obj, "_defer_async_logging", False):
-
-                    def _enqueue_deferred_logging() -> None:
-                        asyncio.create_task(
-                            _client_async_logging_helper(
-                                logging_obj=logging_obj,
-                                result=result,
-                                start_time=start_time,
-                                end_time=end_time,
-                                is_completion_with_fallbacks=is_completion_with_fallbacks,
-                            )
-                        )
-
-                    logging_obj._enqueue_deferred_logging = _enqueue_deferred_logging
-                else:
-                    asyncio.create_task(
-                        _client_async_logging_helper(
-                            logging_obj=logging_obj,
-                            result=result,
-                            start_time=start_time,
-                            end_time=end_time,
-                            is_completion_with_fallbacks=is_completion_with_fallbacks,
-                        )
-                    )
-
-            logging_obj.handle_sync_success_callbacks_for_async_calls(
-                result=result,
-                start_time=start_time,
-                end_time=end_time,
-            )
             # REBUILD EMBEDDING CACHING
             if (
                 isinstance(result, EmbeddingResponse)
                 and _caching_handler_response is not None
                 and _caching_handler_response.final_embedding_cached_response is not None
             ):
+                _dispatch_success_logging(
+                    logging_obj=logging_obj,
+                    result=result,
+                    start_time=start_time,
+                    end_time=end_time,
+                    is_completion_with_fallbacks=is_completion_with_fallbacks,
+                    is_litellm_internal_call=_is_litellm_internal_call,
+                )
                 return _llm_caching_handler._combine_cached_embedding_response_with_api_result(
                     _caching_handler_response=_caching_handler_response,
                     embedding_response=result,
@@ -1998,6 +2016,14 @@ def client(original_function):
                 start_time=start_time,
                 end_time=end_time,
             )
+            _dispatch_success_logging(
+                logging_obj=logging_obj,
+                result=result,
+                start_time=start_time,
+                end_time=end_time,
+                is_completion_with_fallbacks=is_completion_with_fallbacks,
+                is_litellm_internal_call=_is_litellm_internal_call,
+            )
 
             return result
         except Exception as e:
@@ -2197,13 +2223,17 @@ def _return_openai_tokenizer(model: str) -> SelectTokenizerResponse:
     return {"type": "openai_tokenizer", "tokenizer": _get_default_encoding()}
 
 
+def uses_anthropic_tokenizer(model: str) -> bool:
+    return model in litellm.anthropic_models and "claude-3" not in model
+
+
 def _return_huggingface_tokenizer(model: str) -> SelectTokenizerResponse | None:
     if model in litellm.cohere_models and "command-r" in model:
         # cohere
         cohere_tokenizer: Final = Tokenizer.from_pretrained("Xenova/c4ai-command-r-v01-tokenizer")
         return {"type": "huggingface_tokenizer", "tokenizer": cohere_tokenizer}
     # anthropic
-    elif model in litellm.anthropic_models and "claude-3" not in model:
+    elif uses_anthropic_tokenizer(model):
         claude_tokenizer: Final = Tokenizer.from_str(claude_json_str)
         return {"type": "huggingface_tokenizer", "tokenizer": claude_tokenizer}
     # llama2
@@ -2293,15 +2323,7 @@ def create_pretrained_tokenizer(identifier: str, revision="main", auth_token: st
     dict: A dictionary with the tokenizer and its type.
     """
 
-    try:
-        tokenizer = Tokenizer.from_pretrained(
-            identifier,
-            revision=revision,
-            auth_token=auth_token,
-        )
-    except Exception as e:
-        verbose_logger.error("Error creating pretrained tokenizer: %s. Defaulting to version without 'auth_token'.", e)
-        tokenizer = Tokenizer.from_pretrained(identifier, revision=revision)
+    tokenizer: Final = Tokenizer.from_pretrained(identifier, revision=revision, token=auth_token)
     return {"type": "huggingface_tokenizer", "tokenizer": tokenizer}
 
 
@@ -2975,24 +2997,33 @@ def _resolve_builtin_model_cost_entry(key: str, provider: str) -> dict[str, obje
     return None
 
 
+def is_generalized_model_info(model_info: ModelInfo) -> bool:
+    """Whether ``model_info`` came from a fallback-generalization capability rule.
+
+    Detected as the resolved key missing ``litellm.model_cost`` while matching a
+    capability rule. A rule-derived entry carries no pricing and only a conservative
+    family-baseline context window, so callers holding a second candidate name should
+    prefer an exact cost-map entry from that name over this one.
+    """
+    key: Final = cast("Mapping[str, object]", model_info).get("key")  # cast-ok: partial dicts may omit "key"
+    if not isinstance(key, str):
+        return False
+    return key not in litellm.model_cost and match_capability_generalizations(key) is not None
+
+
 def _get_builtin_model_info_for_registration(model: str) -> ModelInfo | None:
     """Resolve ``model`` to its built-in cost-map entry for registration merging.
 
     Returns ``None`` when the lookup raises or when it resolved via a
-    fallback-generalization capability rule, detected as the resolved key missing
-    ``litellm.model_cost`` while matching a capability rule. A rule-derived entry
-    carries no pricing, so treating it as a hit would skip the built-in
-    cache-pricing inheritance for prefix-mangled keys.
+    fallback-generalization capability rule. A rule-derived entry carries no
+    pricing, so treating it as a hit would skip the built-in cache-pricing
+    inheritance for prefix-mangled keys.
     """
     try:
         info: Final = get_model_info(model=model)
     except Exception:
         return None
-    if info["key"] in litellm.model_cost:
-        return info
-    if match_capability_generalizations(info["key"]) is None:
-        return info
-    return None
+    return None if is_generalized_model_info(info) else info
 
 
 _runtime_registered_model_cost: Final[dict[str, dict[str, object]]] = {}  # mutable-ok: replayed on reload
@@ -3079,7 +3110,7 @@ def register_model(
         # Convert stringified numbers to appropriate numeric types
         loaded_model_cost = model_cost
     elif isinstance(model_cost, str):
-        loaded_model_cost = litellm.get_model_cost_map(url=model_cost)
+        loaded_model_cost = litellm.get_model_cost_map(url=model_cost, max_attempts=1)
 
     if persist_across_reloads:
         _registrations: Final[Mapping[str, Mapping[str, object]]] = loaded_model_cost
@@ -3103,7 +3134,10 @@ def register_model(
                 existing_model = cast(dict, builtin_model_info)
                 model_cost_key = existing_model["key"]
             else:
-                existing_model = {}
+                # An exact entry ends the lookup ladder before the capability rules are
+                # consulted, so seed from them: otherwise registering an unmapped model
+                # shadows the very defaults it would have resolved to unregistered.
+                existing_model = dict(match_capability_generalizations(_key_str) or {})  # mutable-ok: merge target
                 model_cost_key = key
                 builtin_entry = _resolve_builtin_model_cost_entry(key=_key_str, provider=provider)
                 if builtin_entry is not None:
@@ -3412,7 +3446,7 @@ def get_optional_params_image_gen(
             non_default_params=non_default_params,
             optional_params=optional_params,
             model=model or "",
-            drop_params=drop_params if drop_params is not None else False,
+            drop_params=litellm.drop_params is True or drop_params is True,
         )
     elif (
         custom_llm_provider == "openai"
@@ -5913,6 +5947,7 @@ def _get_model_info_helper(
                 output_cost_per_second=_model_info.get("output_cost_per_second", None),
                 output_cost_per_second_1080p=_model_info.get("output_cost_per_second_1080p", None),
                 output_cost_per_second_480p=_model_info.get("output_cost_per_second_480p", None),
+                output_cost_per_second_720p=_model_info.get("output_cost_per_second_720p", None),
                 output_cost_per_second_4k=_model_info.get("output_cost_per_second_4k", None),
                 output_cost_per_video_per_second=_model_info.get("output_cost_per_video_per_second", None),
                 output_cost_per_image=_model_info.get("output_cost_per_image", None),
@@ -6989,7 +7024,26 @@ class TextCompletionStreamWrapper:
             raise StopAsyncIteration
 
 
-def mock_completion_streaming_obj(model_response, mock_response, model, n: int | None = None):
+def mock_stream_usage_chunk(model_response: ModelResponseStream, model: str, prompt_tokens: int) -> ModelResponseStream:
+    return ModelResponseStream(
+        id=model_response.id,
+        choices=[],  # mutable-ok: ModelResponseStream only treats a list as explicit choices, a tuple gets a default choice
+        model=model,
+        usage=Usage(
+            prompt_tokens=prompt_tokens,
+            completion_tokens=DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
+            total_tokens=prompt_tokens + DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT,
+        ),
+    )
+
+
+def mock_completion_streaming_obj(
+    model_response: ModelResponseStream,
+    mock_response: str | MockException | ModelResponseStream,
+    model: str,
+    n: int | None = None,
+    prompt_tokens: int | None = None,
+) -> Iterator[ModelResponseStream]:
     if isinstance(mock_response, litellm.MockException):
         raise mock_response
     if isinstance(mock_response, ModelResponseStream):
@@ -7009,14 +7063,17 @@ def mock_completion_streaming_obj(model_response, mock_response, model, n: int |
                 _all_choices.append(_streaming_choice)
             model_response.choices = _all_choices
         yield model_response
+    if prompt_tokens is not None:
+        yield mock_stream_usage_chunk(model_response, model=model, prompt_tokens=prompt_tokens)
 
 
 async def async_mock_completion_streaming_obj(
-    model_response,
+    model_response: ModelResponseStream,
     mock_response: str | MockException | ModelResponseStream,
-    model,
+    model: str,
     n: int | None = None,
-):
+    prompt_tokens: int | None = None,
+) -> AsyncIterator[ModelResponseStream]:
     if isinstance(mock_response, litellm.MockException):
         raise mock_response
     if isinstance(mock_response, ModelResponseStream):
@@ -7036,6 +7093,8 @@ async def async_mock_completion_streaming_obj(
                 _all_choices.append(_streaming_choice)
             model_response.choices = _all_choices
         yield model_response
+    if prompt_tokens is not None:
+        yield mock_stream_usage_chunk(model_response, model=model, prompt_tokens=prompt_tokens)
 
 
 ########## Reading Config File ############################
@@ -8857,6 +8916,12 @@ class ProviderConfigManager:
             )
 
             return AzurePassthroughConfig()
+        elif LlmProviders.AZURE_AI == provider:
+            from litellm.llms.azure_ai.passthrough.transformation import (
+                AzureAIPassthroughConfig,
+            )
+
+            return AzureAIPassthroughConfig()
         elif LlmProviders.GIGACHAT == provider:
             from litellm.llms.gigachat.passthrough.transformation import (
                 GigaChatPassthroughConfig,
@@ -9241,6 +9306,10 @@ class ProviderConfigManager:
             from litellm.llms.openai.image_edit import get_openai_image_edit_config
 
             return get_openai_image_edit_config(model=model)
+        elif LlmProviders.HOSTED_VLLM == provider:
+            from litellm.llms.hosted_vllm.image_edit import get_hosted_vllm_image_edit_config
+
+            return get_hosted_vllm_image_edit_config(model=model)
         elif LlmProviders.AZURE == provider:
             from litellm.llms.azure.image_edit.transformation import (
                 AzureImageEditConfig,
diff --git a/model_prices_and_context_window.json b/model_prices_and_context_window.json
index 7784ed2a6ac..b7726290f0e 100644
--- a/model_prices_and_context_window.json
+++ b/model_prices_and_context_window.json
@@ -364,7 +364,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "amazon.nova-2-lite-v1:0": {
         "cache_read_input_token_cost": 7.5e-08,
@@ -380,6 +381,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -399,6 +401,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -416,6 +419,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -435,6 +439,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -452,6 +457,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -471,6 +477,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -488,6 +495,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -507,6 +515,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -537,7 +546,8 @@
         "output_cost_per_token": 1.4e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "amazon.nova-pro-v1:0": {
         "input_cost_per_token": 8e-07,
@@ -551,7 +561,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "amazon.nova-sonic-v1:0": {
         "deprecation_date": "2026-09-14",
@@ -756,6 +767,14 @@
         "mode": "chat",
         "supports_video_input": true
     },
+    "global.twelvelabs.pegasus-1-2-v1:0": {
+        "input_cost_per_video_per_second": 0.00049,
+        "output_cost_per_token": 7.5e-06,
+        "litellm_provider": "bedrock",
+        "mode": "chat",
+        "supports_video_input": true,
+        "source": "https://aws.amazon.com/bedrock/pricing/"
+    },
     "amazon.titan-text-express-v1": {
         "input_cost_per_token": 1.3e-06,
         "litellm_provider": "bedrock",
@@ -2876,7 +2895,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "apac.amazon.nova-micro-v1:0": {
         "input_cost_per_token": 3.7e-08,
@@ -2888,7 +2908,8 @@
         "output_cost_per_token": 1.48e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "apac.amazon.nova-pro-v1:0": {
         "input_cost_per_token": 8.4e-07,
@@ -2902,7 +2923,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "apac.anthropic.claude-3-5-sonnet-20240620-v1:0": {
         "deprecation_date": "2026-07-30",
@@ -3626,6 +3648,79 @@
         "supports_xhigh_reasoning_effort": true,
         "supports_minimal_reasoning_effort": false
     },
+    "azure_ai/gpt-chat-latest": {
+        "cache_read_input_token_cost": 5e-07,
+        "deprecation_date": "2026-12-02",
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 272000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "output_cost_per_token": 3e-05,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/cognitive-services/openai-service/",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_native_streaming": true,
+        "supports_parallel_function_calling": true,
+        "supports_pdf_input": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_system_messages": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "supports_web_search": true
+    },
+    "azure_ai/codex-mini": {
+        "cache_read_input_token_cost": 3.75e-07,
+        "deprecation_date": "2026-11-15",
+        "input_cost_per_token": 1.5e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 100000,
+        "max_tokens": 100000,
+        "mode": "responses",
+        "output_cost_per_token": 6e-06,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/cognitive-services/openai-service/",
+        "supported_endpoints": [
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_pdf_input": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_system_messages": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
+    "azure_ai/whisper": {
+        "deprecation_date": "2026-12-15",
+        "input_cost_per_second": 0.0001,
+        "litellm_provider": "azure_ai",
+        "mode": "audio_transcription",
+        "output_cost_per_second": 0.0001,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/cognitive-services/openai-service/"
+    },
     "azure_ai/gpt-5.5-2026-04-23": {
         "cache_read_input_token_cost": 5e-07,
         "cache_read_input_token_cost_above_272k_tokens": 1e-06,
@@ -4029,13 +4124,29 @@
         "supports_minimal_reasoning_effort": false
     },
     "azure_ai/model_router": {
+        "deprecation_date": "2027-05-20",
         "input_cost_per_token": 1.4e-07,
         "output_cost_per_token": 0,
         "litellm_provider": "azure_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
         "mode": "chat",
         "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/aoai/",
         "comment": "Flat cost of $0.14 per M input tokens for Azure AI Foundry Model Router infrastructure. Use pattern: azure_ai/model_router/<deployment-name> where deployment-name is your Azure deployment (e.g., azure-model-router)"
     },
+    "azure_ai/model-router": {
+        "deprecation_date": "2027-05-20",
+        "input_cost_per_token": 1.4e-07,
+        "output_cost_per_token": 0,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
+        "mode": "chat",
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/aoai/",
+        "comment": "Catalog-name twin of azure_ai/model_router: the flat $0.14 per M input tokens is the router's own fee, the routed model is priced on top of it"
+    },
     "azure/eu/gpt-4o-2024-08-06": {
         "deprecation_date": "2027-04-14",
         "cache_read_input_token_cost": 1.375e-06,
@@ -7975,7 +8086,8 @@
         "supports_system_messages": true,
         "supports_tool_choice": true,
         "supports_vision": true,
-        "supports_web_search": true
+        "supports_web_search": true,
+        "deprecation_date": "2027-10-26"
     },
     "azure/us/gpt-5.5-2026-04-23": {
         "cache_read_input_token_cost": 5.5e-07,
@@ -8019,7 +8131,8 @@
         "supports_system_messages": true,
         "supports_tool_choice": true,
         "supports_vision": true,
-        "supports_web_search": true
+        "supports_web_search": true,
+        "deprecation_date": "2027-10-26"
     },
     "azure/eu/gpt-5.5-2026-04-23": {
         "cache_read_input_token_cost": 5.5e-07,
@@ -8063,7 +8176,8 @@
         "supports_system_messages": true,
         "supports_tool_choice": true,
         "supports_vision": true,
-        "supports_web_search": true
+        "supports_web_search": true,
+        "deprecation_date": "2027-10-26"
     },
     "azure/gpt-5.5-pro": {
         "cache_read_input_token_cost": 3e-06,
@@ -10347,6 +10461,18 @@
             "/v1/ocr"
         ]
     },
+    "azure_ai/cohere-command-a": {
+        "input_cost_per_token": 2.5e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 131072,
+        "max_output_tokens": 8182,
+        "max_tokens": 8182,
+        "mode": "chat",
+        "output_cost_per_token": 1e-05,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/cohere/",
+        "supports_function_calling": true,
+        "supports_tool_choice": true
+    },
     "azure_ai/doc-intelligence/prebuilt-read": {
         "litellm_provider": "azure_ai",
         "ocr_cost_per_page": 0.0015,
@@ -10698,6 +10824,41 @@
         "supports_vision": true,
         "supports_web_search": true
     },
+    "azure_ai/grok-4-20-reasoning": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "deprecation_date": "2027-04-06",
+        "input_cost_per_token": 1.25e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 262000,
+        "max_output_tokens": 8192,
+        "max_tokens": 8192,
+        "mode": "chat",
+        "output_cost_per_token": 2.5e-06,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/grok/",
+        "supports_function_calling": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "supports_web_search": true,
+        "supports_reasoning": true
+    },
+    "azure_ai/grok-4-20-non-reasoning": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "deprecation_date": "2027-04-06",
+        "input_cost_per_token": 1.25e-06,
+        "litellm_provider": "azure_ai",
+        "max_input_tokens": 262000,
+        "max_output_tokens": 8192,
+        "max_tokens": 8192,
+        "mode": "chat",
+        "output_cost_per_token": 2.5e-06,
+        "source": "https://azure.microsoft.com/en-us/pricing/details/ai-foundry-models/grok/",
+        "supports_function_calling": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "supports_web_search": true
+    },
     "azure_ai/grok-4-fast-non-reasoning": {
         "deprecation_date": "2026-05-01",
         "input_cost_per_token": 2e-07,
@@ -12181,7 +12342,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-east-1/amazon.titan-embed-text-v1": {
         "input_cost_per_token": 1e-07,
@@ -12360,7 +12522,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-west-1/amazon.nova-micro-v1:0": {
         "input_cost_per_token": 4.2e-08,
@@ -12372,7 +12535,8 @@
         "output_cost_per_token": 1.68e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-west-1/amazon.nova-pro-v1:0": {
         "input_cost_per_token": 9.6e-07,
@@ -12386,7 +12550,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "bedrock/us-gov-west-1/amazon.titan-embed-text-v1": {
         "input_cost_per_token": 1e-07,
@@ -13837,7 +14002,8 @@
         "max_output_tokens": 3072,
         "max_tokens": 3072,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-2-7b-chat-int8": {
         "input_cost_per_token": 1.923e-06,
@@ -13846,7 +14012,8 @@
         "max_output_tokens": 2048,
         "max_tokens": 2048,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/mistral/mistral-7b-instruct-v0.1": {
         "input_cost_per_token": 1.923e-06,
@@ -13855,7 +14022,8 @@
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@hf/thebloke/codellama-7b-instruct-awq": {
         "input_cost_per_token": 1.923e-06,
@@ -13864,7 +14032,8 @@
         "max_output_tokens": 4096,
         "max_tokens": 4096,
         "mode": "chat",
-        "output_cost_per_token": 1.923e-06
+        "output_cost_per_token": 1.923e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/openai/gpt-oss-120b": {
         "input_cost_per_token": 3.5e-07,
@@ -13874,6 +14043,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 7.5e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13884,7 +14054,8 @@
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-3.2-3b-instruct": {
         "input_cost_per_token": 5.09e-08,
@@ -13893,7 +14064,8 @@
         "max_output_tokens": 80000,
         "max_tokens": 80000,
         "mode": "chat",
-        "output_cost_per_token": 3.35e-07
+        "output_cost_per_token": 3.35e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-guard-3-8b": {
         "input_cost_per_token": 4.84e-07,
@@ -13902,7 +14074,8 @@
         "max_output_tokens": 131072,
         "max_tokens": 131072,
         "mode": "chat",
-        "output_cost_per_token": 3e-08
+        "output_cost_per_token": 3e-08,
+        "rpm": 300
     },
     "cloudflare/@cf/mistral/mistral-7b-instruct-v0.2-lora": {
         "input_cost_per_token": 0.0,
@@ -13911,7 +14084,8 @@
         "max_output_tokens": 15000,
         "max_tokens": 15000,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/moonshotai/kimi-k2.7-code": {
         "cache_read_input_token_cost": 1.9e-07,
@@ -13922,6 +14096,7 @@
         "max_tokens": 262144,
         "mode": "chat",
         "output_cost_per_token": 4e-06,
+        "rpm": 20,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13933,6 +14108,7 @@
         "max_tokens": 80000,
         "mode": "chat",
         "output_cost_per_token": 4.881e-06,
+        "rpm": 300,
         "supports_reasoning": true
     },
     "cloudflare/@cf/meta/llama-3.1-8b-instruct-fp8": {
@@ -13942,7 +14118,8 @@
         "max_output_tokens": 32000,
         "max_tokens": 32000,
         "mode": "chat",
-        "output_cost_per_token": 2.87e-07
+        "output_cost_per_token": 2.87e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-3.2-1b-instruct": {
         "input_cost_per_token": 2.7e-08,
@@ -13951,7 +14128,8 @@
         "max_output_tokens": 60000,
         "max_tokens": 60000,
         "mode": "chat",
-        "output_cost_per_token": 2.01e-07
+        "output_cost_per_token": 2.01e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/moonshotai/kimi-k2.6": {
         "cache_read_input_token_cost": 1.6e-07,
@@ -13962,6 +14140,7 @@
         "max_tokens": 262144,
         "mode": "chat",
         "output_cost_per_token": 4e-06,
+        "rpm": 20,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13973,6 +14152,7 @@
         "max_tokens": 131072,
         "mode": "chat",
         "output_cost_per_token": 4e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -13983,7 +14163,8 @@
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/meta/llama-3.3-70b-instruct-fp8-fast": {
         "input_cost_per_token": 2.93e-07,
@@ -13993,6 +14174,7 @@
         "max_tokens": 24000,
         "mode": "chat",
         "output_cost_per_token": 2.253e-06,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/ibm-granite/granite-4.0-h-micro": {
@@ -14003,6 +14185,7 @@
         "max_tokens": 131000,
         "mode": "chat",
         "output_cost_per_token": 1.12e-07,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/qwen/qwen2.5-coder-32b-instruct": {
@@ -14012,7 +14195,8 @@
         "max_output_tokens": 32768,
         "max_tokens": 32768,
         "mode": "chat",
-        "output_cost_per_token": 1e-06
+        "output_cost_per_token": 1e-06,
+        "rpm": 300
     },
     "cloudflare/@cf/zai-org/glm-5.2": {
         "cache_read_input_token_cost": 2.6e-07,
@@ -14023,6 +14207,7 @@
         "max_tokens": 262144,
         "mode": "chat",
         "output_cost_per_token": 4.4e-06,
+        "rpm": 20,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14034,6 +14219,7 @@
         "max_tokens": 256000,
         "mode": "chat",
         "output_cost_per_token": 1.5e-06,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14044,7 +14230,8 @@
         "max_output_tokens": 128000,
         "max_tokens": 128000,
         "mode": "chat",
-        "output_cost_per_token": 5.55e-07
+        "output_cost_per_token": 5.55e-07,
+        "rpm": 300
     },
     "cloudflare/@cf/qwen/qwen3-30b-a3b-fp8": {
         "input_cost_per_token": 5.09e-08,
@@ -14054,6 +14241,7 @@
         "max_tokens": 32768,
         "mode": "chat",
         "output_cost_per_token": 3.35e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14064,7 +14252,8 @@
         "max_output_tokens": 3500,
         "max_tokens": 3500,
         "mode": "chat",
-        "output_cost_per_token": 0.0
+        "output_cost_per_token": 0.0,
+        "rpm": 300
     },
     "cloudflare/@cf/google/gemma-4-26b-a4b-it": {
         "input_cost_per_token": 1e-07,
@@ -14074,6 +14263,7 @@
         "max_tokens": 256000,
         "mode": "chat",
         "output_cost_per_token": 3e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14085,6 +14275,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 5.55e-07,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/meta/llama-3.2-11b-vision-instruct": {
@@ -14095,6 +14286,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 6.76e-07,
+        "rpm": 300,
         "supports_vision": true
     },
     "cloudflare/@cf/openai/gpt-oss-20b": {
@@ -14105,6 +14297,7 @@
         "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 3e-07,
+        "rpm": 300,
         "supports_function_calling": true,
         "supports_reasoning": true
     },
@@ -14116,6 +14309,7 @@
         "max_tokens": 131000,
         "mode": "chat",
         "output_cost_per_token": 8.5e-07,
+        "rpm": 300,
         "supports_function_calling": true
     },
     "cloudflare/@cf/qwen/qwq-32b": {
@@ -14126,6 +14320,7 @@
         "max_tokens": 24000,
         "mode": "chat",
         "output_cost_per_token": 1e-06,
+        "rpm": 300,
         "supports_reasoning": true
     },
     "codestral/codestral-2405": {
@@ -14252,6 +14447,28 @@
         "output_vector_size": 1536,
         "supports_embedding_image_input": true
     },
+    "us.cohere.embed-v4:0": {
+        "input_cost_per_token": 1.2e-07,
+        "litellm_provider": "bedrock",
+        "max_input_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "embedding",
+        "output_cost_per_token": 0.0,
+        "output_vector_size": 1536,
+        "supports_embedding_image_input": true,
+        "source": "https://aws.amazon.com/bedrock/pricing/"
+    },
+    "global.cohere.embed-v4:0": {
+        "input_cost_per_token": 1.2e-07,
+        "litellm_provider": "bedrock",
+        "max_input_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "embedding",
+        "output_cost_per_token": 0.0,
+        "output_vector_size": 1536,
+        "supports_embedding_image_input": true,
+        "source": "https://aws.amazon.com/bedrock/pricing/"
+    },
     "cohere/embed-v4.0": {
         "input_cost_per_token": 1.2e-07,
         "litellm_provider": "cohere",
@@ -20823,7 +21040,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "eu.amazon.nova-micro-v1:0": {
         "input_cost_per_token": 4.6e-08,
@@ -20835,7 +21053,8 @@
         "output_cost_per_token": 1.84e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "eu.amazon.nova-pro-v1:0": {
         "input_cost_per_token": 1.05e-06,
@@ -20850,24 +21069,25 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "eu.anthropic.claude-3-5-haiku-20241022-v1:0": {
-        "input_cost_per_token": 2.5e-07,
+        "input_cost_per_token": 8e-07,
         "litellm_provider": "bedrock",
         "max_input_tokens": 200000,
         "max_output_tokens": 8192,
         "max_tokens": 8192,
         "mode": "chat",
-        "output_cost_per_token": 1.25e-06,
+        "output_cost_per_token": 4e-06,
         "supports_assistant_prefill": true,
         "supports_function_calling": true,
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
         "supports_tool_choice": true,
-        "cache_read_input_token_cost": 2.5e-08,
-        "cache_creation_input_token_cost": 3.125e-07,
+        "cache_read_input_token_cost": 8e-08,
+        "cache_creation_input_token_cost": 1e-06,
         "prompt_cache_min_tokens": 2048
     },
     "eu.anthropic.claude-haiku-4-5-20251001-v1:0": {
@@ -23874,9 +24094,9 @@
         "input_cost_per_audio_token": 3e-06,
         "input_cost_per_token": 5e-07,
         "litellm_provider": "vertex_ai-language-models",
-        "max_input_tokens": 1048576,
-        "max_output_tokens": 65535,
-        "max_tokens": 65535,
+        "max_input_tokens": 131072,
+        "max_output_tokens": 65536,
+        "max_tokens": 65536,
         "mode": "realtime",
         "output_cost_per_audio_token": 1.2e-05,
         "output_cost_per_token": 2e-06,
@@ -23899,12 +24119,12 @@
         "supports_audio_output": true,
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
-        "supports_pdf_input": true,
-        "supports_prompt_caching": true,
-        "supports_response_schema": true,
+        "supports_pdf_input": false,
+        "supports_prompt_caching": false,
+        "supports_response_schema": false,
         "supports_system_messages": true,
         "supports_tool_choice": true,
-        "supports_url_context": true,
+        "supports_url_context": false,
         "supports_vision": true,
         "supports_web_search": true,
         "search_context_cost_per_query": {
@@ -27696,6 +27916,70 @@
         "max_tokens": 8191,
         "mode": "embedding"
     },
+    "chatgpt/gpt-5.5": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.5",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
+    "chatgpt/gpt-5.6-luna": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.6-luna",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
+    "chatgpt/gpt-5.6-sol": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.6-sol",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
+    "chatgpt/gpt-5.6-terra": {
+        "litellm_provider": "chatgpt",
+        "source": "https://platform.openai.com/docs/models/gpt-5.6-terra",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supports_function_calling": true,
+        "supports_parallel_function_calling": true,
+        "supports_response_schema": true,
+        "supports_vision": true
+    },
     "chatgpt/gpt-5.4": {
         "litellm_provider": "chatgpt",
         "max_input_tokens": 1050000,
@@ -28302,6 +28586,7 @@
         "supports_prompt_caching": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
+        "supports_tool_choice": true,
         "supports_video_input": true,
         "supports_vision": true
     },
@@ -29126,7 +29411,12 @@
         "supports_response_schema": true,
         "supports_system_messages": true,
         "supports_tool_choice": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "search_context_cost_per_query": {
+            "search_context_size_high": 0.025,
+            "search_context_size_low": 0.025,
+            "search_context_size_medium": 0.025
+        }
     },
     "gpt-4o-mini-2024-07-18": {
         "cache_read_input_token_cost": 7.5e-08,
@@ -29143,9 +29433,9 @@
         "output_cost_per_token_priority": 1e-06,
         "output_cost_per_token_batches": 3e-07,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.03,
+            "search_context_size_high": 0.025,
             "search_context_size_low": 0.025,
-            "search_context_size_medium": 0.0275
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29244,9 +29534,9 @@
         "output_cost_per_token": 6e-07,
         "output_cost_per_token_batches": 3e-07,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.03,
+            "search_context_size_high": 0.025,
             "search_context_size_low": 0.025,
-            "search_context_size_medium": 0.0275
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29271,9 +29561,9 @@
         "output_cost_per_token": 6e-07,
         "output_cost_per_token_batches": 3e-07,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.03,
+            "search_context_size_high": 0.025,
             "search_context_size_low": 0.025,
-            "search_context_size_medium": 0.0275
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29384,9 +29674,9 @@
         "output_cost_per_token": 1e-05,
         "output_cost_per_token_batches": 5e-06,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.05,
-            "search_context_size_low": 0.03,
-            "search_context_size_medium": 0.035
+            "search_context_size_high": 0.025,
+            "search_context_size_low": 0.025,
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29411,9 +29701,9 @@
         "output_cost_per_token": 1e-05,
         "output_cost_per_token_batches": 5e-06,
         "search_context_cost_per_query": {
-            "search_context_size_high": 0.05,
-            "search_context_size_low": 0.03,
-            "search_context_size_medium": 0.035
+            "search_context_size_high": 0.025,
+            "search_context_size_low": 0.025,
+            "search_context_size_medium": 0.025
         },
         "supports_function_calling": true,
         "supports_parallel_function_calling": true,
@@ -29495,6 +29785,66 @@
         "supports_vision": true,
         "supports_pdf_input": true
     },
+    "gpt-image-2.5-flare": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
+    "gpt-image-2.5-flare-2026-09-08": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
+    "gpt-image-2.5-sunburst": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
+    "gpt-image-2.5-sunburst-2026-09-08": {
+        "cache_read_input_token_cost": 1.25e-06,
+        "input_cost_per_token": 5e-06,
+        "litellm_provider": "openai",
+        "mode": "image_generation",
+        "input_cost_per_image_token": 8e-06,
+        "output_cost_per_image_token": 3e-05,
+        "supported_endpoints": [
+            "/v1/images/generations",
+            "/v1/images/edits"
+        ],
+        "supports_vision": true,
+        "supports_pdf_input": true,
+        "source": "https://developers.openai.com/api/docs/pricing"
+    },
     "low/1024-x-1024/gpt-image-1.5": {
         "deprecation_date": "2026-12-01",
         "input_cost_per_image": 0.009,
@@ -29945,7 +30295,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": false,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.1-2025-11-13": {
         "cache_read_input_token_cost": 1.25e-07,
@@ -29990,7 +30340,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": false,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.1-chat-latest": {
         "cache_read_input_token_cost": 1.25e-07,
@@ -30082,7 +30432,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.2-2025-12-11": {
         "cache_read_input_token_cost": 1.75e-07,
@@ -30128,7 +30478,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true
+        "supports_minimal_reasoning_effort": false
     },
     "gpt-5.2-chat-latest": {
         "cache_read_input_token_cost": 1.75e-07,
@@ -31124,7 +31474,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 2.5e-06,
         "output_cost_per_token_above_272k_tokens_flex": 1.125e-05,
         "cache_read_input_token_cost_above_272k_tokens_flex": 2.5e-07
@@ -31176,7 +31526,7 @@
         "supports_none_reasoning_effort": true,
         "default_reasoning_effort": "none",
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 2.5e-06,
         "output_cost_per_token_above_272k_tokens_flex": 1.125e-05,
         "cache_read_input_token_cost_above_272k_tokens_flex": 2.5e-07
@@ -31228,7 +31578,7 @@
         "supports_web_search": true,
         "supports_none_reasoning_effort": false,
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 3e-05,
         "output_cost_per_token_above_272k_tokens_flex": 0.000135
     },
@@ -31279,7 +31629,7 @@
         "supports_web_search": true,
         "supports_none_reasoning_effort": false,
         "supports_xhigh_reasoning_effort": true,
-        "supports_minimal_reasoning_effort": true,
+        "supports_minimal_reasoning_effort": false,
         "input_cost_per_token_above_272k_tokens_flex": 3e-05,
         "output_cost_per_token_above_272k_tokens_flex": 0.000135
     },
@@ -33359,13 +33709,14 @@
         "supports_tool_choice": true
     },
     "jina-reranker-v2-base-multilingual": {
-        "input_cost_per_token": 1.8e-08,
+        "input_cost_per_token": 5e-08,
         "litellm_provider": "jina_ai",
         "max_input_tokens": 1024,
         "max_output_tokens": 1024,
         "max_tokens": 1024,
         "mode": "rerank",
-        "output_cost_per_token": 1.8e-08
+        "output_cost_per_token": 0.0,
+        "source": "https://api.jina.ai/v1/models"
     },
     "jp.anthropic.claude-sonnet-4-5-20250929-v1:0": {
         "cache_creation_input_token_cost": 4.125e-06,
@@ -39619,6 +39970,45 @@
         "supports_tool_choice": true,
         "supports_vision": true
     },
+    "openrouter/openai/gpt-5.6-sol": {
+        "cache_creation_input_token_cost": 2.5e-06,
+        "cache_creation_input_token_cost_above_272k_tokens": 5e-06,
+        "cache_read_input_token_cost": 2e-07,
+        "cache_read_input_token_cost_above_272k_tokens": 4e-07,
+        "default_reasoning_effort": "medium",
+        "input_cost_per_token": 2e-06,
+        "input_cost_per_token_above_272k_tokens": 4e-06,
+        "litellm_provider": "openrouter",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "output_cost_per_token": 1e-05,
+        "output_cost_per_token_above_272k_tokens": 1.5e-05,
+        "reasoning_effort_levels": [
+            "none",
+            "low",
+            "medium",
+            "high",
+            "xhigh",
+            "max"
+        ],
+        "source": "https://openrouter.ai/openai/gpt-5.6-sol",
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_pdf_input": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
     "openrouter/openai/gpt-oss-120b": {
         "input_cost_per_token": 3.7e-08,
         "litellm_provider": "openrouter",
@@ -41575,6 +41965,28 @@
         "mode": "rerank",
         "output_cost_per_token": 0.0
     },
+    "rerank-v4.0-fast": {
+        "input_cost_per_query": 0.002,
+        "input_cost_per_token": 0.0,
+        "litellm_provider": "cohere",
+        "max_input_tokens": 32768,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
+        "mode": "rerank",
+        "output_cost_per_token": 0.0,
+        "source": "https://cohere.com/pricing"
+    },
+    "rerank-v4.0-pro": {
+        "input_cost_per_query": 0.0025,
+        "input_cost_per_token": 0.0,
+        "litellm_provider": "cohere",
+        "max_input_tokens": 32768,
+        "max_output_tokens": 32768,
+        "max_tokens": 32768,
+        "mode": "rerank",
+        "output_cost_per_token": 0.0,
+        "source": "https://cohere.com/pricing"
+    },
     "nvidia_nim/nvidia/nv-rerankqa-mistral-4b-v3": {
         "input_cost_per_query": 0.0,
         "input_cost_per_token": 0.0,
@@ -43535,7 +43947,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "us.amazon.nova-micro-v1:0": {
         "input_cost_per_token": 3.5e-08,
@@ -43547,7 +43960,8 @@
         "output_cost_per_token": 1.4e-07,
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "supports_response_schema": true
+        "supports_response_schema": true,
+        "supports_tool_choice": true
     },
     "us.amazon.nova-premier-v1:0": {
         "deprecation_date": "2026-09-14",
@@ -43576,7 +43990,8 @@
         "supports_pdf_input": true,
         "supports_prompt_caching": true,
         "supports_response_schema": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "supports_tool_choice": true
     },
     "us.anthropic.claude-3-5-haiku-20241022-v1:0": {
         "cache_creation_input_token_cost": 1e-06,
@@ -45755,8 +46170,8 @@
         "input_cost_per_token": 1e-06,
         "litellm_provider": "vertex_ai-anthropic_models",
         "max_input_tokens": 200000,
-        "max_output_tokens": 8192,
-        "max_tokens": 8192,
+        "max_output_tokens": 64000,
+        "max_tokens": 64000,
         "mode": "chat",
         "output_cost_per_token": 5e-06,
         "regional_endpoint_uplift_multiplier": 1.1,
@@ -45780,8 +46195,8 @@
         "input_cost_per_token": 1e-06,
         "litellm_provider": "vertex_ai-anthropic_models",
         "max_input_tokens": 200000,
-        "max_output_tokens": 8192,
-        "max_tokens": 8192,
+        "max_output_tokens": 64000,
+        "max_tokens": 64000,
         "mode": "chat",
         "output_cost_per_token": 5e-06,
         "regional_endpoint_uplift_multiplier": 1.1,
@@ -47761,9 +48176,9 @@
         "cache_read_input_token_cost": 5e-08,
         "input_cost_per_token": 2e-07,
         "litellm_provider": "vertex_ai",
-        "max_input_tokens": 2000000,
-        "max_output_tokens": 2000000,
-        "max_tokens": 2000000,
+        "max_input_tokens": 128000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 5e-07,
         "source": "https://docs.x.ai/developers/models",
@@ -47777,9 +48192,9 @@
         "cache_read_input_token_cost": 5e-08,
         "input_cost_per_token": 2e-07,
         "litellm_provider": "vertex_ai",
-        "max_input_tokens": 2000000,
-        "max_output_tokens": 2000000,
-        "max_tokens": 2000000,
+        "max_input_tokens": 128000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
         "mode": "chat",
         "output_cost_per_token": 5e-07,
         "source": "https://docs.x.ai/developers/models",
@@ -47792,14 +48207,17 @@
     },
     "vertex_ai/xai/grok-4.20-non-reasoning": {
         "cache_read_input_token_cost": 2e-07,
-        "input_cost_per_token": 2e-06,
+        "cache_read_input_token_cost_above_200k_tokens": 4e-07,
+        "input_cost_per_token": 1.25e-06,
+        "input_cost_per_token_above_200k_tokens": 2.5e-06,
         "litellm_provider": "vertex_ai",
         "max_input_tokens": 2000000,
         "max_output_tokens": 2000000,
         "max_tokens": 2000000,
         "mode": "chat",
-        "output_cost_per_token": 6e-06,
-        "source": "https://docs.x.ai/developers/models",
+        "output_cost_per_token": 2.5e-06,
+        "output_cost_per_token_above_200k_tokens": 5e-06,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
         "supports_function_calling": true,
         "supports_response_schema": true,
         "supports_tool_choice": true,
@@ -47808,14 +48226,17 @@
     },
     "vertex_ai/xai/grok-4.20-reasoning": {
         "cache_read_input_token_cost": 2e-07,
-        "input_cost_per_token": 2e-06,
+        "cache_read_input_token_cost_above_200k_tokens": 4e-07,
+        "input_cost_per_token": 1.25e-06,
+        "input_cost_per_token_above_200k_tokens": 2.5e-06,
         "litellm_provider": "vertex_ai",
         "max_input_tokens": 2000000,
         "max_output_tokens": 2000000,
         "max_tokens": 2000000,
         "mode": "chat",
-        "output_cost_per_token": 6e-06,
-        "source": "https://docs.x.ai/developers/models",
+        "output_cost_per_token": 2.5e-06,
+        "output_cost_per_token_above_200k_tokens": 5e-06,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
         "supports_function_calling": true,
         "supports_reasoning": true,
         "supports_response_schema": true,
@@ -47823,6 +48244,44 @@
         "supports_vision": true,
         "supports_web_search": true
     },
+    "vertex_ai/xai/grok-4.3": {
+        "cache_read_input_token_cost": 2e-07,
+        "cache_read_input_token_cost_above_200k_tokens": 4e-07,
+        "input_cost_per_token": 1.25e-06,
+        "input_cost_per_token_above_200k_tokens": 2.5e-06,
+        "litellm_provider": "vertex_ai",
+        "max_input_tokens": 200000,
+        "max_output_tokens": 200000,
+        "max_tokens": 200000,
+        "mode": "chat",
+        "output_cost_per_token": 2.5e-06,
+        "output_cost_per_token_above_200k_tokens": 5e-06,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
+        "supports_function_calling": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
+    "vertex_ai/xai/grok-4.6": {
+        "cache_read_input_token_cost": 5e-07,
+        "cache_read_input_token_cost_above_200k_tokens": 1e-06,
+        "input_cost_per_token": 2e-06,
+        "input_cost_per_token_above_200k_tokens": 4e-06,
+        "litellm_provider": "vertex_ai",
+        "max_input_tokens": 524288,
+        "max_output_tokens": 524288,
+        "max_tokens": 524288,
+        "mode": "chat",
+        "output_cost_per_token": 6e-06,
+        "output_cost_per_token_above_200k_tokens": 1.2e-05,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
+        "supports_function_calling": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true
+    },
     "vertex_ai/qwen/qwen3-235b-a22b-instruct-2507-maas": {
         "input_cost_per_token": 2.2e-07,
         "litellm_provider": "vertex_ai-qwen_models",
@@ -48081,6 +48540,16 @@
         "mode": "embedding",
         "output_cost_per_token": 0.0
     },
+    "voyage/voyage-multilingual-2": {
+        "input_cost_per_token": 1.2e-07,
+        "litellm_provider": "voyage",
+        "max_input_tokens": 32000,
+        "max_tokens": 32000,
+        "mode": "embedding",
+        "output_cost_per_token": 0.0,
+        "output_vector_size": 1024,
+        "source": "https://docs.voyageai.com/docs/pricing"
+    },
     "voyage/voyage-3-large": {
         "input_cost_per_token": 1.8e-07,
         "litellm_provider": "voyage",
@@ -48186,6 +48655,7 @@
         "output_cost_per_token": 0.0
     },
     "wandb/openai/gpt-oss-120b": {
+        "supports_reasoning": true,
         "max_tokens": 131072,
         "max_input_tokens": 131072,
         "max_output_tokens": 131072,
@@ -48196,6 +48666,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/openai/gpt-oss-20b": {
+        "supports_reasoning": true,
         "max_tokens": 131072,
         "max_input_tokens": 131072,
         "max_output_tokens": 131072,
@@ -48206,6 +48677,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/zai-org/GLM-4.5": {
+        "supports_reasoning": true,
         "max_tokens": 131072,
         "max_input_tokens": 131072,
         "max_output_tokens": 131072,
@@ -48234,6 +48706,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3-235B-A22B-Thinking-2507": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "max_output_tokens": 262144,
@@ -48290,6 +48763,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-V3.1": {
+        "supports_reasoning": true,
         "max_tokens": 128000,
         "max_input_tokens": 161000,
         "max_output_tokens": 128000,
@@ -48300,6 +48774,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-R1-0528": {
+        "supports_reasoning": true,
         "max_tokens": 161000,
         "max_input_tokens": 161000,
         "max_output_tokens": 161000,
@@ -52154,7 +52629,8 @@
         "max_tokens": 32768,
         "mode": "chat",
         "output_cost_per_token": 8e-07,
-        "supports_function_calling": true
+        "supports_function_calling": true,
+        "deprecation_date": "2026-10-01"
     },
     "scaleway/openai/gpt-oss-120b": {
         "input_cost_per_token": 1.5e-07,
@@ -52193,7 +52669,8 @@
         "mode": "chat",
         "output_cost_per_token": 5e-07,
         "supports_function_calling": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "deprecation_date": "2026-08-01"
     },
     "scaleway/hcompany/holo2-30b-a3b": {
         "input_cost_per_token": 3e-07,
@@ -52204,7 +52681,8 @@
         "mode": "chat",
         "output_cost_per_token": 7e-07,
         "supports_reasoning": true,
-        "supports_vision": true
+        "supports_vision": true,
+        "deprecation_date": "2026-08-09"
     },
     "scaleway/mistralai/mistral-medium-3.5-128b": {
         "input_cost_per_token": 1.5e-06,
@@ -52227,7 +52705,8 @@
         "max_tokens": 16384,
         "mode": "chat",
         "output_cost_per_token": 2e-06,
-        "supports_function_calling": true
+        "supports_function_calling": true,
+        "deprecation_date": "2026-08-01"
     },
     "scaleway/mistralai/voxtral-small-24b-2507": {
         "input_cost_per_audio_token": 1.5e-07,
@@ -52238,7 +52717,8 @@
         "max_tokens": 16384,
         "mode": "chat",
         "output_cost_per_token": 3.5e-07,
-        "supports_audio_input": true
+        "supports_audio_input": true,
+        "deprecation_date": "2026-08-01"
     },
     "scaleway/mistralai/mistral-small-3.2-24b-instruct-2506": {
         "input_cost_per_token": 1.5e-07,
@@ -52260,7 +52740,8 @@
         "mode": "chat",
         "output_cost_per_token": 2e-07,
         "supports_vision": true,
-        "supports_function_calling": true
+        "supports_function_calling": true,
+        "deprecation_date": "2026-10-01"
     },
     "scaleway/BAAI/bge-multilingual-gemma2": {
         "input_cost_per_token": 1e-07,
@@ -54710,7 +55191,7 @@
         "supports_tool_choice": true
     },
     "bedrock_mantle/openai.gpt-oss-20b": {
-        "input_cost_per_token": 7.5e-08,
+        "input_cost_per_token": 7e-08,
         "output_cost_per_token": 3e-07,
         "litellm_provider": "bedrock_mantle",
         "max_input_tokens": 131072,
@@ -54744,8 +55225,8 @@
         "supports_tool_choice": true
     },
     "bedrock_mantle/openai.gpt-oss-safeguard-20b": {
-        "input_cost_per_token": 7.5e-08,
-        "output_cost_per_token": 3e-07,
+        "input_cost_per_token": 7e-08,
+        "output_cost_per_token": 2e-07,
         "litellm_provider": "bedrock_mantle",
         "max_input_tokens": 131072,
         "max_output_tokens": 65536,
@@ -54865,6 +55346,39 @@
         "supports_tool_choice": true,
         "supports_vision": true
     },
+    "bedrock_mantle/openai.gpt-daybreak-blue-5.6-sol": {
+        "input_cost_per_token": 5.5e-06,
+        "input_cost_per_token_above_272k_tokens": 1.1e-05,
+        "cache_creation_input_token_cost": 6.875e-06,
+        "cache_creation_input_token_cost_above_272k_tokens": 1.375e-05,
+        "cache_read_input_token_cost": 5.5e-07,
+        "cache_read_input_token_cost_above_272k_tokens": 1.1e-06,
+        "output_cost_per_token": 3.3e-05,
+        "output_cost_per_token_above_272k_tokens": 4.95e-05,
+        "litellm_provider": "bedrock_mantle",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "use_openai_responses_path": true,
+        "supported_endpoints": [
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-daybreak-blue-56-sol.html"
+    },
     "bedrock_mantle/openai.gpt-5.6-luna": {
         "input_cost_per_token": 2.2e-07,
         "input_cost_per_token_above_272k_tokens": 4.4e-07,
@@ -55060,6 +55574,96 @@
         "supports_reasoning": true,
         "supports_vision": true
     },
+    "bedrock_mantle/openai.gpt-6-astra": {
+        "input_cost_per_token": 1.1e-05,
+        "input_cost_per_token_above_272k_tokens": 2.2e-05,
+        "cache_creation_input_token_cost": 1.375e-05,
+        "cache_creation_input_token_cost_above_272k_tokens": 2.75e-05,
+        "cache_read_input_token_cost": 1.1e-06,
+        "cache_read_input_token_cost_above_272k_tokens": 2.2e-06,
+        "output_cost_per_token": 5.5e-05,
+        "output_cost_per_token_above_272k_tokens": 8.25e-05,
+        "litellm_provider": "bedrock_mantle",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "responses",
+        "use_openai_responses_path": true,
+        "supported_endpoints": [
+            "/v1/chat/completions",
+            "/v1/responses"
+        ],
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_response_schema": true,
+        "supports_tool_choice": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-6-astra.html"
+    },
+    "us.openai.gpt-6-astra": {
+        "input_cost_per_token": 1.1e-05,
+        "input_cost_per_token_above_272k_tokens": 2.2e-05,
+        "cache_creation_input_token_cost": 1.375e-05,
+        "cache_creation_input_token_cost_above_272k_tokens": 2.75e-05,
+        "cache_read_input_token_cost": 1.1e-06,
+        "cache_read_input_token_cost_above_272k_tokens": 2.2e-06,
+        "output_cost_per_token": 5.5e-05,
+        "output_cost_per_token_above_272k_tokens": 8.25e-05,
+        "litellm_provider": "bedrock_converse",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_tool_choice": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-6-astra.html"
+    },
+    "global.openai.gpt-6-astra": {
+        "input_cost_per_token": 1e-05,
+        "input_cost_per_token_above_272k_tokens": 2e-05,
+        "cache_creation_input_token_cost": 1.25e-05,
+        "cache_creation_input_token_cost_above_272k_tokens": 2.5e-05,
+        "cache_read_input_token_cost": 1e-06,
+        "cache_read_input_token_cost_above_272k_tokens": 2e-06,
+        "output_cost_per_token": 5e-05,
+        "output_cost_per_token_above_272k_tokens": 7.5e-05,
+        "litellm_provider": "bedrock_converse",
+        "max_input_tokens": 1050000,
+        "max_output_tokens": 128000,
+        "max_tokens": 128000,
+        "mode": "chat",
+        "supported_modalities": [
+            "text",
+            "image"
+        ],
+        "supported_output_modalities": [
+            "text"
+        ],
+        "supports_function_calling": true,
+        "supports_tool_choice": true,
+        "supports_prompt_caching": true,
+        "supports_reasoning": true,
+        "supports_vision": true,
+        "source": "https://docs.aws.amazon.com/bedrock/latest/userguide/model-card-openai-gpt-6-astra.html"
+    },
     "bedrock_mantle/openai.gpt-5.5": {
         "input_cost_per_token": 5.5e-06,
         "input_cost_per_token_above_272k_tokens": 1.1e-05,
@@ -56654,6 +57258,14 @@
                 "model_info": {
                     "supports_mid_conversation_system": true
                 }
+            },
+            {
+                "name": "wandb-reasoning-baseline",
+                "pattern": "^wandb/",
+                "description": "Any Weights & Biases Inference model id, anchored to the wandb/ namespace so only that provider's ids match. W&B's serverless catalog is reasoning-first and grows faster than this registry names it, so an id the map has not described yet is treated as reasoning-capable and keeps the caller's reasoning_effort instead of dropping it or raising UnsupportedParamsError. Rules lose to exact entries, so a mapped non-reasoning model such as wandb/meta-llama/Llama-3.1-8B-Instruct is unaffected. Carries no mode and no pricing, so cost stays on the standard unpriced behavior and the deployment does not read as catalog-mapped to the router's reasoning-effort resolver.",
+                "model_info": {
+                    "supports_reasoning": true
+                }
             }
         ]
     },
@@ -56725,8 +57337,8 @@
         "rpm": 10
     },
     "vertex_ai/gemini-3.5-transcribe-preview": {
-        "input_cost_per_audio_token": 2.5e-06,
-        "input_cost_per_token": 2.5e-06,
+        "input_cost_per_audio_token": 2e-06,
+        "input_cost_per_token": 2e-06,
         "litellm_provider": "vertex_ai",
         "mode": "audio_transcription",
         "output_cost_per_token": 1.2e-05,
@@ -56761,6 +57373,27 @@
         ],
         "supports_audio_input": true
     },
+    "vertex_ai/gemini-3.5-live-translate-preview": {
+        "input_cost_per_audio_token": 3.5e-06,
+        "input_cost_per_token": 3.5e-06,
+        "litellm_provider": "vertex_ai",
+        "mode": "realtime",
+        "output_cost_per_audio_token": 2.1e-05,
+        "output_cost_per_token": 2.1e-05,
+        "source": "https://cloud.google.com/gemini-enterprise-agent-platform/generative-ai/pricing",
+        "supported_endpoints": [
+            "/v1/realtime"
+        ],
+        "supported_modalities": [
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "audio",
+            "text"
+        ],
+        "supports_audio_input": true,
+        "supports_audio_output": true
+    },
     "perplexity/pplx-embed-context-v1-0.6b": {
         "input_cost_per_token": 8e-09,
         "litellm_provider": "perplexity",
@@ -58011,6 +58644,7 @@
         "supports_vision": false
     },
     "wandb/deepseek-ai/DeepSeek-V4-Flash": {
+        "supports_reasoning": true,
         "max_tokens": 1048576,
         "max_input_tokens": 1048576,
         "input_cost_per_token": 1.4e-07,
@@ -58023,6 +58657,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-V4-Flash-0731": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 1.3e-07,
@@ -58035,6 +58670,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/deepseek-ai/DeepSeek-V4-Pro": {
+        "supports_reasoning": true,
         "max_tokens": 1048576,
         "max_input_tokens": 1048576,
         "input_cost_per_token": 1.15e-06,
@@ -58047,6 +58683,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/google/gemma-4-31B-it": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 1e-07,
@@ -58087,6 +58724,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/MiniMaxAI/MiniMax-M3": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 2.3e-07,
@@ -58099,6 +58737,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/moonshotai/Kimi-K2.7-Code": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 7.1e-07,
@@ -58111,6 +58750,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/moonshotai/Kimi-K2.6": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 6.5e-07,
@@ -58123,6 +58763,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/nvidia/NVIDIA-Nemotron-3.5-Lightning-30B-A3B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 1e-07,
@@ -58135,6 +58776,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/nvidia/NVIDIA-Nemotron-3-Ultra-550B-A55B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 7.5e-07,
@@ -58157,6 +58799,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.8-27B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 4e-07,
@@ -58169,6 +58812,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.6-35B-A3B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 2.5e-07,
@@ -58179,6 +58823,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.6-27B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 6e-07,
@@ -58191,6 +58836,7 @@
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
     "wandb/Qwen/Qwen3.5-35B-A3B": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 2.5e-07,
@@ -58210,7 +58856,28 @@
         "supports_vision": false,
         "source": "https://wandb.ai/site/pricing/tokens/"
     },
+    "wandb/deepseek-ai/DeepSeek-V4-Pro-0813": {
+        "litellm_provider": "wandb",
+        "mode": "chat",
+        "supports_reasoning": true,
+        "input_cost_per_token": 0.00000131,
+        "output_cost_per_token": 0.00000396,
+        "cache_read_input_token_cost": 0.000000044,
+        "supports_prompt_caching": true,
+        "source": "https://wandb.ai/site/pricing/tokens/"
+    },
+    "wandb/ibm-granite/granite-4.2-8b": {
+        "litellm_provider": "wandb",
+        "mode": "chat",
+        "supports_reasoning": true,
+        "input_cost_per_token": 0.0000001,
+        "output_cost_per_token": 0.00000015,
+        "cache_read_input_token_cost": 0.00000005,
+        "supports_prompt_caching": true,
+        "source": "https://wandb.ai/site/pricing/tokens/"
+    },
     "wandb/zai-org/GLM-5.2": {
+        "supports_reasoning": true,
         "max_tokens": 262144,
         "max_input_tokens": 262144,
         "input_cost_per_token": 7.6e-07,
@@ -59452,6 +60119,77 @@
             "image"
         ]
     },
+    "xai/grok-imagine-video": {
+        "input_cost_per_image": 0.002,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.05,
+        "output_cost_per_second_480p": 0.05,
+        "output_cost_per_second_720p": 0.07,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video",
+        "supported_modalities": [
+            "text",
+            "image",
+            "video"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
+    "xai/grok-imagine-video-1.5": {
+        "input_cost_per_image": 0.01,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.08,
+        "output_cost_per_second_1080p": 0.25,
+        "output_cost_per_second_480p": 0.08,
+        "output_cost_per_second_720p": 0.14,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video-1.5",
+        "supported_modalities": [
+            "text",
+            "image",
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
+    "xai/grok-imagine-video-1.5-2026-05-30": {
+        "input_cost_per_image": 0.01,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.08,
+        "output_cost_per_second_1080p": 0.25,
+        "output_cost_per_second_480p": 0.08,
+        "output_cost_per_second_720p": 0.14,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video-1.5",
+        "supported_modalities": [
+            "text",
+            "image",
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
+    "xai/grok-imagine-video-1.5-preview": {
+        "input_cost_per_image": 0.01,
+        "litellm_provider": "xai",
+        "mode": "video_generation",
+        "output_cost_per_second": 0.08,
+        "output_cost_per_second_1080p": 0.25,
+        "output_cost_per_second_480p": 0.08,
+        "output_cost_per_second_720p": 0.14,
+        "source": "https://docs.x.ai/docs/models/grok-imagine-video-1.5",
+        "supported_modalities": [
+            "text",
+            "image",
+            "audio"
+        ],
+        "supported_output_modalities": [
+            "video"
+        ]
+    },
     "low/1024-x-1024/grok-imagine-image-2.0": {
         "input_cost_per_image": 0.04,
         "litellm_provider": "xai",
@@ -60719,6 +61457,7 @@
         "litellm_provider": "cloudflare",
         "mode": "audio_transcription",
         "output_cost_per_second": 0.0,
+        "rpm": 720,
         "source": "https://developers.cloudflare.com/workers-ai/models/whisper/",
         "supported_endpoints": [
             "/v1/audio/transcriptions"
@@ -60729,6 +61468,7 @@
         "litellm_provider": "cloudflare",
         "mode": "audio_transcription",
         "output_cost_per_second": 0.0,
+        "rpm": 720,
         "source": "https://developers.cloudflare.com/workers-ai/models/whisper-large-v3-turbo/",
         "supported_endpoints": [
             "/v1/audio/transcriptions"
@@ -60784,6 +61524,31 @@
         "supports_web_search": false,
         "output_cost_per_image": 0.08
     },
+    "gemini/lyria-3.5": {
+        "input_cost_per_token": 0,
+        "litellm_provider": "gemini",
+        "max_input_tokens": 1048576,
+        "max_output_tokens": 65536,
+        "max_tokens": 65536,
+        "mode": "chat",
+        "output_cost_per_token": 0,
+        "source": "https://ai.google.dev/gemini-api/docs/pricing",
+        "supported_modalities": [
+            "text"
+        ],
+        "supported_output_modalities": [
+            "audio"
+        ],
+        "supports_audio_input": false,
+        "supports_audio_output": true,
+        "supports_function_calling": false,
+        "supports_prompt_caching": false,
+        "supports_response_schema": false,
+        "supports_system_messages": false,
+        "supports_vision": false,
+        "supports_web_search": false,
+        "output_cost_per_image": 0.08
+    },
     "perplexity/anthropic/claude-fable-5": {
         "litellm_provider": "perplexity",
         "mode": "responses",
diff --git a/model_prices_and_context_window.schema.json b/model_prices_and_context_window.schema.json
index 47a1934a703..7ed1e7e568b 100644
--- a/model_prices_and_context_window.schema.json
+++ b/model_prices_and_context_window.schema.json
@@ -478,6 +478,10 @@
           "type": "number",
           "minimum": 0
         },
+        "output_cost_per_second_720p": {
+          "type": "number",
+          "minimum": 0
+        },
         "output_cost_per_token": {
           "type": "number",
           "minimum": 0,
diff --git a/pyproject.toml b/pyproject.toml
index 04f2f3fd1dd..d33d693f794 100644
--- a/pyproject.toml
+++ b/pyproject.toml
@@ -67,7 +67,7 @@ proxy = [
     "azure-identity>=1.25.2,<2.0",
     "azure-storage-blob>=12.28.0,<13.0",
     "mcp>=1.28.1,<2.0",
-    "litellm-proxy-extras==0.4.95",
+    "litellm-proxy-extras==0.4.96",
     "litellm-enterprise==0.1.66",
     "RestrictedPython>=8.5,<9.0",
     "rich>=13.9.4,<14.0",
diff --git a/schema.prisma b/schema.prisma
index 3d254cd2ea2..817df082d8c 100644
--- a/schema.prisma
+++ b/schema.prisma
@@ -282,6 +282,7 @@ model LiteLLM_ObjectPermissionTable {
   mcp_toolsets          String[]       @default([]) // Toolset IDs granted to this key/team/user
   search_tools          String[]       @default([]) // search_tool_name values this key/team/user may call
   mcp_tool_search_enabled Boolean?
+  skills                String[]       @default([]) // Claude Code plugin names granted to this key/team beyond the public (enabled) set
   teams                 LiteLLM_TeamTable[]
   projects              LiteLLM_ProjectTable[]
   verification_tokens   LiteLLM_VerificationToken[]
@@ -492,7 +493,7 @@ model LiteLLM_JWTKeyMapping {
     updated_at        DateTime @default(now()) @updatedAt
     updated_by        String?
 
-    litellm_verification_token LiteLLM_VerificationToken @relation(fields: [token], references: [token])
+    litellm_verification_token LiteLLM_VerificationToken @relation(fields: [token], references: [token], onDelete: Cascade)
 
     @@unique([jwt_claim_name, jwt_claim_value])
     @@index([jwt_claim_name, jwt_claim_value, is_active])
diff --git a/terraform/litellm/README.md b/terraform/litellm/README.md
index d4b40741052..7cc6e4c08ba 100644
--- a/terraform/litellm/README.md
+++ b/terraform/litellm/README.md
@@ -183,6 +183,7 @@ only where the underlying cloud forces it.
 | Extra secret-backed env          | `gateway_extra_secrets`, `backend_extra_secrets` (ARNs) | `gateway_extra_secrets`, `backend_extra_secrets` (resource IDs) |
 | Uvicorn `--workers` on gateway   | `gateway_num_workers`                                   | `gateway_num_workers`                                     |
 | OpenTelemetry v2 (opt-in)        | `otel_endpoint`, `otel_exporter`, `otel_environment_name`, `otel_capture_message_content`, `otel_headers_secret_arn` | `otel_endpoint`, `otel_exporter`, `otel_environment_name`, `otel_capture_message_content`, `otel_headers_secret` |
+| Collector sidecar (opt-in)    | `collector_enabled`, `collector_port`, `collector_cpu`, `collector_memory`, `collector_buffer_size`, `collector_on_unavailable`, `collector_drain_timeout_seconds` | same names; `collector_cpu` / `collector_memory` take Cloud Run strings |
 
 Each module stamps its own stack-identity tag (`litellm:stack` on AWS,
 `litellm-stack` on GCP — GCP label keys forbid colons) plus
diff --git a/terraform/litellm/aws/README.md b/terraform/litellm/aws/README.md
index 923a4ca2da8..6fcbdc2f500 100644
--- a/terraform/litellm/aws/README.md
+++ b/terraform/litellm/aws/README.md
@@ -258,6 +258,133 @@ gateway_metrics_port         = 4001
 gateway_metrics_scrape_cidrs = ["10.0.0.0/16"]
 ```
 
+### In-container connection pool
+
+Each of the `gateway_num_workers` uvicorn workers opens its own Prisma pool
+straight to Postgres, so one task holds `workers x connection_limit`
+connections and the fleet's footprint against the database ceiling grows with
+every task. `gateway_connection_pool_enabled` runs a PgBouncer (transaction
+mode, loopback) inside the gateway container that all workers share, capping
+the task at `gateway_pool_max_db_connections` upstream connections however
+many workers it runs. `gateway_pool_max_client_conn` bounds the worker-side
+connections the pooler accepts. The module sets
+`LITELLM_PGBOUNCER_ENABLED`, `LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS` and
+`LITELLM_PGBOUNCER_MAX_CLIENT_CONN` on the gateway container only; the backend
+and the migration task keep the direct connection.
+
+```hcl
+gateway_num_workers             = 4
+gateway_connection_pool_enabled = true
+gateway_pool_max_db_connections = 20
+gateway_pool_max_client_conn    = 1000
+```
+
+The pool works with the module-created Aurora as well as an existing database
+via `database_url`. Against Aurora it authenticates with the same rotating IAM
+tokens the workers used to (see [Aurora + IAM auth](#aurora--iam-auth)): the
+pooler mints a token from the task role, renews it before it expires and hands
+the workers a loopback URL with a static password instead
+
+The componentized `gateway_image` starts through `python -m gateway.launch`,
+which reads these variables, starts the pooler once per task and hands the
+workers its loopback URL; the classic `litellm` image honours them the same
+way.
+
+### Scaling the gateway on requests and tokens
+
+By default the gateway service target-tracks CPU (`gateway_cpu_target`) and
+memory (`gateway_memory_target`). Two more targets add workload signals next
+to them. Application Auto Scaling evaluates every attached policy and follows
+the one asking for the most tasks, so the resource policies keep working as a
+floor while requests or tokens drive scale-out
+
+Both targets are per task per second, the way load is usually quoted (1k
+rps, 75M tok/s). CloudWatch is the limit on how fast they react: target
+tracking evaluates every metric, predefined or custom, aggregated over
+60-second periods and has no period setting, so ECS reacts on a roughly
+one-minute cadence whatever unit the variable is written in. The Kubernetes
+charts get a faster signal because the Prometheus `rate()` window and scrape
+interval are theirs to shorten
+
+`gateway_target_requests_per_second` adds an `ALBRequestCountPerTarget`
+policy on the gateway target group. The ALB publishes that metric as requests
+per minute per registered task, so the policy's target value is 60 times the
+variable: 90 rps becomes a target of 5,400 per minute. No agent or sidecar is
+needed
+
+`gateway_target_tokens_per_second` adds a metric-math policy over a
+CloudWatch metric of the gateway's `litellm_total_tokens_metric_total`
+counter and the service's `RunningTaskCount` from Container Insights. Nothing
+native to ECS carries token throughput, so you publish that metric yourself
+with the CloudWatch agent's Prometheus scraper pointed at the metrics sidecar
+above. The agent emits the delta of a counter between scrapes, so `Sum` over
+the 60-second period is the tokens served in that minute; the expression
+divides by 60 (`tokens_per_second`) and then by the task count
+(`tokens_per_second_per_task`). Tokens are counted when a response completes,
+so long streams show up late in this signal. `gateway_tokens_metric` tells the
+policy where the agent publishes: the namespace, the metric name (defaults to
+the counter name) and the dimensions from your `metric_declaration`
+
+```hcl
+gateway_metrics_port               = 4001
+gateway_target_requests_per_second = 90
+gateway_target_tokens_per_second   = 6000000
+gateway_tokens_metric = {
+  namespace  = "LiteLLM/Prometheus"
+  dimensions = { ClusterName = "acme-litellm-prod", TaskDefinitionFamily = "acme-litellm-prod-gateway" }
+}
+```
+
+Worked example for the request policy: 1,000 rps across 10 tasks is 100 rps
+per task (the ALB reports it as 6,000 per minute per target) against a target
+of 90 (5,400), so target tracking sizes the service to
+`ceil(10 * 100 / 90) = 12` tasks. The token policy does the same arithmetic:
+ten tasks handle 4,200,000,000 tokens in a minute, `tokens / 60` is
+70,000,000 tokens per second and `tokens_per_second / running_tasks` is
+7,000,000 against a target of 6,000,000, so the service grows to
+`ceil(10 * 7000000 / 6000000) = 12`. Container Insights must be enabled on the
+cluster for `RunningTaskCount` to exist
+
+### Collector sidecar
+
+`collector_enabled = true` adds a second container to the gateway task
+that runs `python -m litellm.proxy.collector` from the gateway image, and sets
+`LITELLM_COLLECTOR_ENABLED=true` on the gateway so its uvicorn workers
+ship spend events (SpendLogs writes, key/team/user spend updates, budget
+alerts) to the sidecar instead of running that pipeline in the request
+path. This is the Terraform counterpart of helm's `gateway.collector`.
+The default (`false`) leaves the task definition exactly as before.
+
+Fargate tasks share one network namespace, so the sidecar listens on
+loopback TCP (`tcp://127.0.0.1:${collector_port}`, default 4010) instead
+of the Unix socket helm uses; the proxy rejects any non-loopback address.
+The sidecar gets the same database, Redis, master-key, license, proxy
+config, and `gateway_extra_env` / `gateway_extra_secrets` values as the
+gateway container, runs with `LITELLM_JOB_ROLE=collector`, and is
+non-essential with an ECS restart policy, so a sidecar crash restarts it in
+place while the gateway falls back to in-process spend tracking. With
+`gateway_connection_pool_enabled` it also gets the `LITELLM_PGBOUNCER_*` env,
+so with a password-authenticated database (`create_database = false`) its
+Prisma client goes through the task-local PgBouncer instead of opening a
+second pool straight to the database. Under IAM token auth (the module-managed
+Aurora cluster) the collector keeps its own direct connection on purpose: the
+pooler's auth file only holds the token the gateway container minted, which
+the sidecar cannot present, so it mints its own.
+
+```hcl
+collector_enabled = true
+# collector_cpu               = 512    # carved out of gateway_cpu
+# collector_memory            = 2048   # MiB, carved out of gateway_memory
+# collector_buffer_size       = 1000
+# collector_on_unavailable    = "fallback"  # or "drop"
+# collector_drain_timeout_seconds = 10
+```
+
+Both sidecar reservations must leave room for the gateway container inside
+`gateway_cpu` / `gateway_memory` (the plan fails otherwise). Service
+autoscaling keeps tracking the whole task's CPU and memory, sidecar
+included
+
 ## Tenant deployment
 
 Every resource the stack creates is named `${tenant}-litellm-${env}` (or
diff --git a/terraform/litellm/aws/autoscaling.tf b/terraform/litellm/aws/autoscaling.tf
index 71b6c24fac7..5197311d1b3 100644
--- a/terraform/litellm/aws/autoscaling.tf
+++ b/terraform/litellm/aws/autoscaling.tf
@@ -52,6 +52,105 @@ resource "aws_appautoscaling_policy" "gateway_memory" {
   }
 }
 
+resource "aws_appautoscaling_policy" "gateway_requests" {
+  count              = var.gateway_autoscaling_enabled && var.gateway_target_requests_per_second > 0 ? 1 : 0
+  name               = "${local.name}-gateway-requests"
+  policy_type        = "TargetTrackingScaling"
+  service_namespace  = aws_appautoscaling_target.gateway[0].service_namespace
+  resource_id        = aws_appautoscaling_target.gateway[0].resource_id
+  scalable_dimension = aws_appautoscaling_target.gateway[0].scalable_dimension
+
+  target_tracking_scaling_policy_configuration {
+    predefined_metric_specification {
+      predefined_metric_type = "ALBRequestCountPerTarget"
+      resource_label         = "${aws_lb.this.arn_suffix}/${aws_lb_target_group.gateway.arn_suffix}"
+    }
+    # ALBRequestCountPerTarget is a per-minute count
+    target_value = var.gateway_target_requests_per_second * 60
+  }
+}
+
+resource "aws_appautoscaling_policy" "gateway_tokens" {
+  count              = var.gateway_autoscaling_enabled && var.gateway_target_tokens_per_second > 0 ? 1 : 0
+  name               = "${local.name}-gateway-tokens"
+  policy_type        = "TargetTrackingScaling"
+  service_namespace  = aws_appautoscaling_target.gateway[0].service_namespace
+  resource_id        = aws_appautoscaling_target.gateway[0].resource_id
+  scalable_dimension = aws_appautoscaling_target.gateway[0].scalable_dimension
+
+  lifecycle {
+    precondition {
+      condition     = var.gateway_tokens_metric != null
+      error_message = "gateway_tokens_metric is required when gateway_target_tokens_per_second > 0."
+    }
+  }
+
+  target_tracking_scaling_policy_configuration {
+    target_value = var.gateway_target_tokens_per_second
+
+    # target tracking has no period setting and always aggregates over 60s
+    customized_metric_specification {
+      metrics {
+        id          = "tokens"
+        return_data = false
+
+        metric_stat {
+          stat = "Sum"
+
+          metric {
+            namespace   = var.gateway_tokens_metric.namespace
+            metric_name = var.gateway_tokens_metric.name
+
+            dynamic "dimensions" {
+              for_each = var.gateway_tokens_metric.dimensions
+              content {
+                name  = dimensions.key
+                value = dimensions.value
+              }
+            }
+          }
+        }
+      }
+
+      metrics {
+        id          = "running_tasks"
+        return_data = false
+
+        metric_stat {
+          stat = "Average"
+
+          metric {
+            namespace   = "ECS/ContainerInsights"
+            metric_name = "RunningTaskCount"
+
+            dimensions {
+              name  = "ClusterName"
+              value = aws_ecs_cluster.this.name
+            }
+            dimensions {
+              name  = "ServiceName"
+              value = aws_ecs_service.gateway.name
+            }
+          }
+        }
+      }
+
+      metrics {
+        id          = "tokens_per_second"
+        expression  = "tokens / 60"
+        return_data = false
+      }
+
+      metrics {
+        id          = "tokens_per_second_per_task"
+        expression  = "tokens_per_second / running_tasks"
+        label       = "Tokens per second per gateway task"
+        return_data = true
+      }
+    }
+  }
+}
+
 # ---------- Backend ----------
 resource "aws_appautoscaling_target" "backend" {
   count              = var.backend_autoscaling_enabled ? 1 : 0
diff --git a/terraform/litellm/aws/ecs.tf b/terraform/litellm/aws/ecs.tf
index aa2c3d558e2..2b235c2bad5 100644
--- a/terraform/litellm/aws/ecs.tf
+++ b/terraform/litellm/aws/ecs.tf
@@ -213,6 +213,12 @@ locals {
   # otherwise we keep the image's ENTRYPOINT and only override `command`.
   gateway_uvicorn_args = "--host 0.0.0.0 --port 4000 --workers ${var.gateway_num_workers}"
 
+  gateway_pool_env = var.gateway_connection_pool_enabled ? [
+    { name = "LITELLM_PGBOUNCER_ENABLED", value = "true" },
+    { name = "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS", value = tostring(var.gateway_pool_max_db_connections) },
+    { name = "LITELLM_PGBOUNCER_MAX_CLIENT_CONN", value = tostring(var.gateway_pool_max_client_conn) },
+  ] : []
+
   metrics_enabled       = var.gateway_metrics_port != null
   metrics_multiproc_dir = "/tmp/litellm_prometheus_multiproc"
   metrics_volume        = "prometheus-multiproc"
@@ -253,7 +259,7 @@ locals {
 
   backend_uvicorn_args = "--host 0.0.0.0 --port 4001"
 
-  gateway_launch_cmd = "case \"$USE_DDTRACE\" in [Tt][Rr][Uu][Ee]) export DD_TRACE_OPENAI_ENABLED=\"False\"; exec ddtrace-run uvicorn gateway.main:app ${local.gateway_uvicorn_args};; *) exec uvicorn gateway.main:app ${local.gateway_uvicorn_args};; esac"
+  gateway_launch_cmd = "case \"$USE_DDTRACE\" in [Tt][Rr][Uu][Ee]) export DD_TRACE_OPENAI_ENABLED=\"False\"; exec ddtrace-run python -m gateway.launch ${local.gateway_uvicorn_args};; *) exec python -m gateway.launch ${local.gateway_uvicorn_args};; esac"
   backend_launch_cmd = "case \"$USE_DDTRACE\" in [Tt][Rr][Uu][Ee]) export DD_TRACE_OPENAI_ENABLED=\"False\"; exec ddtrace-run uvicorn backend.main:app ${local.backend_uvicorn_args};; *) exec uvicorn backend.main:app ${local.backend_uvicorn_args};; esac"
 
   gateway_proxy_overrides = local.proxy_config_enabled ? {
@@ -272,6 +278,62 @@ locals {
       "${local.proxy_config_fetch_cmd} && ${local.backend_launch_cmd}"
     ]
   } : {}
+
+  collector_address = "tcp://127.0.0.1:${var.collector_port}"
+  collector_env = var.collector_enabled ? [
+    { name = "LITELLM_COLLECTOR_ENABLED", value = "true" },
+    { name = "LITELLM_COLLECTOR_ADDRESS", value = local.collector_address },
+    { name = "LITELLM_COLLECTOR_BUFFER_SIZE", value = tostring(var.collector_buffer_size) },
+    { name = "LITELLM_COLLECTOR_ON_UNAVAILABLE", value = var.collector_on_unavailable },
+    { name = "LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS", value = tostring(var.collector_drain_timeout_seconds) },
+  ] : []
+
+  gateway_environment = concat(
+    local.shared_env,
+    local.gateway_otel_env,
+    local.billing_metrics_env,
+    local.gateway_extra_env_list,
+    local.proxy_config_env,
+    local.metrics_env,
+    local.gateway_pool_env,
+    local.collector_env,
+  )
+
+  collector_launch_cmd = "exec python -m litellm.proxy.collector"
+  collector_command = [
+    local.proxy_config_enabled ? "${local.proxy_config_fetch_cmd} && ${local.collector_launch_cmd}" : local.collector_launch_cmd
+  ]
+
+  collector_container = var.collector_enabled ? [{
+    name      = "collector"
+    image     = var.gateway_image
+    essential = false
+    cpu       = var.collector_cpu
+    memory    = var.collector_memory
+
+    restartPolicy = { enabled = true }
+
+    entryPoint = ["sh", "-c"]
+    command    = local.collector_command
+    environment = concat(
+      local.shared_env,
+      local.gateway_extra_env_list,
+      local.proxy_config_env,
+      local.gateway_pool_env,
+      local.collector_env,
+      [{ name = "LITELLM_JOB_ROLE", value = "collector" }],
+    )
+    secrets = concat(local.shared_secrets, local.gateway_extra_secrets_list)
+
+    logConfiguration = {
+      logDriver = "awslogs"
+      options = {
+        awslogs-group         = aws_cloudwatch_log_group.gateway.name
+        awslogs-region        = var.region
+        awslogs-stream-prefix = "collector"
+      }
+    }
+  }] : []
 }
 
 # ---------- Gateway ----------
@@ -298,6 +360,21 @@ resource "aws_ecs_task_definition" "gateway" {
       )
       error_message = "billing_metrics_client_cert_pem and billing_metrics_client_key_pem are both required when billing_metrics_endpoint is set."
     }
+
+    precondition {
+      condition     = !var.gateway_connection_pool_enabled || local.database_enabled
+      error_message = "gateway_connection_pool_enabled needs a database: set create_database = true or pass database_url."
+    }
+
+    precondition {
+      condition     = !var.collector_enabled || (var.collector_cpu < var.gateway_cpu && var.collector_memory < var.gateway_memory)
+      error_message = "collector_cpu and collector_memory are carved out of gateway_cpu / gateway_memory and must leave room for the gateway container."
+    }
+
+    precondition {
+      condition     = !var.collector_enabled || var.gateway_metrics_port == null || var.collector_port != var.gateway_metrics_port
+      error_message = "collector_port and gateway_metrics_port must differ: both sidecars bind loopback in the same task."
+    }
   }
 
   family                   = "${local.name}-gateway"
@@ -316,16 +393,9 @@ resource "aws_ecs_task_definition" "gateway" {
         essential = true
 
         portMappings = [{ containerPort = 4000, protocol = "tcp" }]
-        environment = concat(
-          local.shared_env,
-          local.gateway_otel_env,
-          local.billing_metrics_env,
-          local.gateway_extra_env_list,
-          local.proxy_config_env,
-          local.metrics_env,
-        )
-        secrets     = concat(local.shared_secrets, local.gateway_extra_secrets_list)
-        mountPoints = local.metrics_mount_points
+        environment  = local.gateway_environment
+        secrets      = concat(local.shared_secrets, local.gateway_extra_secrets_list)
+        mountPoints  = local.metrics_mount_points
 
         # Container-level healthCheck intentionally omitted — the wolfi
         # runtime image doesn't ship curl/wget. The ALB target group polls
@@ -342,7 +412,7 @@ resource "aws_ecs_task_definition" "gateway" {
       },
       local.gateway_proxy_overrides,
     )
-  ], local.gateway_metrics_container))
+  ], local.gateway_metrics_container, local.collector_container))
 
   dynamic "volume" {
     for_each = local.metrics_enabled ? [1] : []
diff --git a/terraform/litellm/aws/tests/collector.tftest.hcl b/terraform/litellm/aws/tests/collector.tftest.hcl
new file mode 100644
index 00000000000..1465130232f
--- /dev/null
+++ b/terraform/litellm/aws/tests/collector.tftest.hcl
@@ -0,0 +1,144 @@
+# Plan-only coverage for the opt-in collector sidecar in the gateway task.
+# The rendered container_definitions JSON is unknown at plan time (it embeds
+# Aurora/ElastiCache endpoints and secret ARNs), so the assertions target the
+# locals it is built from. Run from terraform/litellm/aws with `terraform test`.
+
+mock_provider "aws" {
+  mock_data "aws_iam_policy_document" {
+    defaults = {
+      json = "{\"Version\":\"2012-10-17\",\"Statement\":[]}"
+    }
+  }
+}
+mock_provider "random" {}
+
+variables {
+  region              = "us-east-1"
+  tenant              = "acme"
+  env                 = "test"
+  allow_plaintext_alb = true
+  azs                 = ["us-east-1a", "us-east-1b"]
+}
+
+run "disabled_by_default_leaves_the_task_untouched" {
+  command = plan
+
+  assert {
+    condition     = length(local.collector_container) == 0
+    error_message = "The gateway task must stay single-container unless collector_enabled is set."
+  }
+
+  assert {
+    condition     = !anytrue([for e in local.gateway_environment : startswith(e.name, "LITELLM_COLLECTOR_")])
+    error_message = "No LITELLM_COLLECTOR_* env may reach the gateway while the sidecar is disabled."
+  }
+}
+
+run "enabled_adds_a_sidecar_that_shares_the_gateway_transport" {
+  command = plan
+
+  variables {
+    collector_enabled        = true
+    collector_port           = 4321
+    collector_buffer_size    = 250
+    collector_on_unavailable = "drop"
+    gateway_extra_env        = { OPENAI_API_BASE = "https://example.invalid" }
+    gateway_extra_secrets    = { OPENAI_API_KEY = "arn:aws:secretsmanager:us-east-1:111122223333:secret:openai-AbCdEf" }
+  }
+
+  assert {
+    condition     = length(local.collector_container) == 1 && local.collector_container[0].name == "collector"
+    error_message = "Enabling the sidecar must add exactly one collector container."
+  }
+
+  assert {
+    condition = alltrue([
+      for env in [local.gateway_environment, local.collector_container[0].environment] : (
+        { for e in env : e.name => e.value }["LITELLM_COLLECTOR_ENABLED"] == "true" &&
+        { for e in env : e.name => e.value }["LITELLM_COLLECTOR_ADDRESS"] == "tcp://127.0.0.1:4321" &&
+        { for e in env : e.name => e.value }["LITELLM_COLLECTOR_BUFFER_SIZE"] == "250" &&
+        { for e in env : e.name => e.value }["LITELLM_COLLECTOR_ON_UNAVAILABLE"] == "drop" &&
+        { for e in env : e.name => e.value }["LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS"] == "10"
+      )
+    ])
+    error_message = "Gateway and sidecar must agree on the loopback address and the collector knobs."
+  }
+
+  assert {
+    condition = (
+      local.collector_container[0].image == var.gateway_image &&
+      local.collector_container[0].entryPoint == ["sh", "-c"] &&
+      local.collector_container[0].command == ["exec python -m litellm.proxy.collector"] &&
+      local.collector_container[0].essential == false &&
+      local.collector_container[0].restartPolicy.enabled == true &&
+      { for e in local.collector_container[0].environment : e.name => e.value }["LITELLM_JOB_ROLE"] == "collector"
+    )
+    error_message = "The sidecar must run litellm.proxy.collector from the gateway image as a restartable, non-essential collector."
+  }
+
+  assert {
+    condition = (
+      { for e in local.collector_container[0].environment : e.name => e.value }["OPENAI_API_BASE"] == "https://example.invalid" &&
+      contains([for e in local.collector_container[0].environment : e.name], "DATABASE_HOST") &&
+      contains([for e in local.collector_container[0].environment : e.name], "REDIS_HOST") &&
+      contains([for s in local.collector_container[0].secrets : s.name], "LITELLM_MASTER_KEY") &&
+      contains([for s in local.collector_container[0].secrets : s.name], "OPENAI_API_KEY")
+    )
+    error_message = "The sidecar must receive the gateway's database, Redis, and shared secrets plus gateway_extra_env / gateway_extra_secrets."
+  }
+
+  assert {
+    condition     = !contains(keys(local.collector_container[0]), "portMappings")
+    error_message = "The sidecar must not expose a port to the task's load balancer."
+  }
+
+  assert {
+    condition     = local.collector_container[0].cpu == 512 && local.collector_container[0].memory == 2048
+    error_message = "The sidecar defaults must mirror helm's collector resources (500m / 2Gi)."
+  }
+}
+
+run "proxy_config_is_fetched_by_the_sidecar_too" {
+  command = plan
+
+  variables {
+    collector_enabled = true
+    proxy_config      = { model_list = [] }
+  }
+
+  assert {
+    condition = (
+      startswith(local.collector_container[0].command[0], local.proxy_config_fetch_cmd) &&
+      endswith(local.collector_container[0].command[0], "exec python -m litellm.proxy.collector") &&
+      contains([for e in local.collector_container[0].environment : e.name], "CONFIG_FILE_PATH")
+    )
+    error_message = "The sidecar must pull the proxy config from S3 before starting, like the gateway does."
+  }
+}
+
+run "sidecar_must_leave_room_for_the_gateway" {
+  command = plan
+
+  variables {
+    collector_enabled = true
+    collector_cpu     = 1024
+  }
+
+  expect_failures = [
+    aws_ecs_task_definition.gateway,
+  ]
+}
+
+run "sidecars_must_not_share_a_loopback_port" {
+  command = plan
+
+  variables {
+    collector_enabled    = true
+    collector_port       = 4001
+    gateway_metrics_port = 4001
+  }
+
+  expect_failures = [
+    aws_ecs_task_definition.gateway,
+  ]
+}
diff --git a/terraform/litellm/aws/tests/connection_pool.tftest.hcl b/terraform/litellm/aws/tests/connection_pool.tftest.hcl
new file mode 100644
index 00000000000..7408b1179ed
--- /dev/null
+++ b/terraform/litellm/aws/tests/connection_pool.tftest.hcl
@@ -0,0 +1,164 @@
+# Plan-only coverage for the in-container PgBouncer knobs on the gateway task.
+# `mock_provider` keeps this offline: no AWS credentials, no API calls, no
+# resources. Run from terraform/litellm/aws with `terraform test`.
+
+mock_provider "aws" {
+  mock_data "aws_iam_policy_document" {
+    defaults = {
+      json = "{\"Version\":\"2012-10-17\",\"Statement\":[]}"
+    }
+  }
+}
+mock_provider "random" {}
+
+variables {
+  region              = "us-east-1"
+  tenant              = "acme"
+  env                 = "test"
+  azs                 = ["us-east-1a", "us-east-1b"]
+  allow_plaintext_alb = true
+}
+
+run "pool_off_by_default" {
+  command = plan
+
+  assert {
+    condition     = length(local.gateway_pool_env) == 0
+    error_message = "The gateway must get no LITELLM_PGBOUNCER_* env unless gateway_connection_pool_enabled is set."
+  }
+}
+
+run "pool_enabled_renders_the_three_vars_with_configured_sizes" {
+  command = plan
+
+  variables {
+    create_database                 = false
+    database_url                    = "postgresql://litellm:pw@db.internal:5432/litellm"
+    gateway_num_workers             = 4
+    gateway_connection_pool_enabled = true
+    gateway_pool_max_db_connections = 8
+    gateway_pool_max_client_conn    = 250
+  }
+
+  assert {
+    condition = alltrue([
+      length(local.gateway_pool_env) == 3,
+      local.gateway_pool_env[0].name == "LITELLM_PGBOUNCER_ENABLED" && local.gateway_pool_env[0].value == "true",
+      local.gateway_pool_env[1].name == "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS" && local.gateway_pool_env[1].value == "8",
+      local.gateway_pool_env[2].name == "LITELLM_PGBOUNCER_MAX_CLIENT_CONN" && local.gateway_pool_env[2].value == "250",
+    ])
+    error_message = "The pool env must carry the enabled flag and the configured sizes as strings."
+  }
+}
+
+run "collector_sidecar_gets_the_same_pool_env_as_the_gateway" {
+  command = plan
+
+  variables {
+    create_database                 = false
+    database_url                    = "postgresql://litellm:pw@db.internal:5432/litellm"
+    collector_enabled               = true
+    gateway_connection_pool_enabled = true
+    gateway_pool_max_db_connections = 8
+    gateway_pool_max_client_conn    = 250
+  }
+
+  assert {
+    condition = alltrue([
+      for env in [local.gateway_environment, local.collector_container[0].environment] : (
+        { for e in env : e.name => e.value }["LITELLM_PGBOUNCER_ENABLED"] == "true" &&
+        { for e in env : e.name => e.value }["LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS"] == "8" &&
+        { for e in env : e.name => e.value }["LITELLM_PGBOUNCER_MAX_CLIENT_CONN"] == "250"
+      )
+    ])
+    error_message = "The collector sidecar must carry the same three LITELLM_PGBOUNCER_* vars as the gateway so its Prisma connects to the task-local pool."
+  }
+}
+
+run "collector_sidecar_gets_no_pool_env_when_the_pool_is_off" {
+  command = plan
+
+  variables {
+    collector_enabled = true
+  }
+
+  assert {
+    condition     = !anytrue([for e in local.collector_container[0].environment : startswith(e.name, "LITELLM_PGBOUNCER_")])
+    error_message = "The collector sidecar must get no LITELLM_PGBOUNCER_* env unless gateway_connection_pool_enabled is set."
+  }
+}
+
+run "pool_enabled_uses_the_module_default_sizes" {
+  command = plan
+
+  variables {
+    create_database                 = false
+    database_url                    = "postgresql://litellm:pw@db.internal:5432/litellm"
+    gateway_connection_pool_enabled = true
+  }
+
+  assert {
+    condition = alltrue([
+      length(local.gateway_pool_env) == 3,
+      local.gateway_pool_env[1].name == "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS" && local.gateway_pool_env[1].value == "20",
+      local.gateway_pool_env[2].name == "LITELLM_PGBOUNCER_MAX_CLIENT_CONN" && local.gateway_pool_env[2].value == "1000",
+    ])
+    error_message = "The pool env must fall back to the module defaults of 20 upstream and 1000 client connections."
+  }
+}
+
+run "gateway_starts_through_the_pool_aware_launcher" {
+  command = plan
+
+  variables {
+    gateway_num_workers = 4
+  }
+
+  assert {
+    condition = alltrue([
+      strcontains(local.gateway_launch_cmd, "exec python -m gateway.launch --host 0.0.0.0 --port 4000 --workers 4"),
+      strcontains(local.gateway_launch_cmd, "exec ddtrace-run python -m gateway.launch --host 0.0.0.0 --port 4000 --workers 4"),
+      !strcontains(local.gateway_launch_cmd, "uvicorn gateway.main:app"),
+      local.gateway_proxy_overrides.command[0] == local.gateway_launch_cmd,
+    ])
+    error_message = "The gateway must start through gateway.launch (with and without ddtrace) so the pooler starts once before uvicorn forks the workers."
+  }
+}
+
+run "pool_with_module_created_iam_aurora_plans_with_both_the_pool_and_iam_auth" {
+  command = plan
+
+  variables {
+    gateway_connection_pool_enabled = true
+  }
+
+  assert {
+    condition = alltrue([
+      length(local.gateway_pool_env) == 3,
+      contains(local.managed_db_env, { name = "IAM_TOKEN_DB_AUTH", value = "true" }),
+    ])
+    error_message = "With the module-created Aurora the gateway must get the pool env alongside IAM token auth."
+  }
+}
+
+run "pool_without_any_database_fails_at_plan" {
+  command = plan
+
+  variables {
+    create_database                 = false
+    gateway_connection_pool_enabled = true
+  }
+
+  expect_failures = [
+    aws_ecs_task_definition.gateway,
+  ]
+}
+
+run "module_created_iam_aurora_without_the_pool_still_plans" {
+  command = plan
+
+  assert {
+    condition     = contains(local.managed_db_env, { name = "IAM_TOKEN_DB_AUTH", value = "true" })
+    error_message = "Without the pool the module-created Aurora must keep IAM token auth."
+  }
+}
diff --git a/terraform/litellm/aws/tests/workload_autoscaling.tftest.hcl b/terraform/litellm/aws/tests/workload_autoscaling.tftest.hcl
new file mode 100644
index 00000000000..94e281faf94
--- /dev/null
+++ b/terraform/litellm/aws/tests/workload_autoscaling.tftest.hcl
@@ -0,0 +1,194 @@
+# Plan-only coverage for the gateway request and token autoscaling policies.
+# Offline via mock_provider, same as byo_infrastructure.tftest.hcl.
+
+mock_provider "aws" {
+  mock_data "aws_iam_policy_document" {
+    defaults = {
+      json = "{\"Version\":\"2012-10-17\",\"Statement\":[]}"
+    }
+  }
+}
+mock_provider "random" {}
+
+variables {
+  region              = "us-east-1"
+  tenant              = "acme"
+  env                 = "test"
+  allow_plaintext_alb = true
+  azs                 = ["us-east-1a", "us-east-1b"]
+}
+
+run "defaults_scale_on_cpu_and_memory_only" {
+  command = plan
+
+  assert {
+    condition = alltrue([
+      length(aws_appautoscaling_policy.gateway_cpu) == 1,
+      length(aws_appautoscaling_policy.gateway_memory) == 1,
+      length(aws_appautoscaling_policy.gateway_requests) == 0,
+      length(aws_appautoscaling_policy.gateway_tokens) == 0,
+    ])
+    error_message = "Request and token policies must be absent by default while the CPU and memory policies stay."
+  }
+}
+
+run "requests_per_second_adds_an_alb_request_count_policy" {
+  command = plan
+
+  variables {
+    gateway_target_requests_per_second = 90
+  }
+
+  assert {
+    condition     = length(aws_appautoscaling_policy.gateway_requests) == 1 && length(aws_appautoscaling_policy.gateway_tokens) == 0
+    error_message = "A request target alone must add exactly the request policy."
+  }
+
+  assert {
+    condition = alltrue([
+      aws_appautoscaling_policy.gateway_requests[0].name == "acme-litellm-test-gateway-requests",
+      aws_appautoscaling_policy.gateway_requests[0].policy_type == "TargetTrackingScaling",
+      aws_appautoscaling_policy.gateway_requests[0].service_namespace == "ecs",
+      aws_appautoscaling_policy.gateway_requests[0].resource_id == "service/acme-litellm-test/acme-litellm-test-gateway",
+      aws_appautoscaling_policy.gateway_requests[0].scalable_dimension == "ecs:service:DesiredCount",
+    ])
+    error_message = "The request policy must be a target-tracking policy on the gateway service's desired count."
+  }
+
+  assert {
+    condition = alltrue([
+      one(aws_appautoscaling_policy.gateway_requests[0].target_tracking_scaling_policy_configuration).target_value == 5400,
+      one(one(aws_appautoscaling_policy.gateway_requests[0].target_tracking_scaling_policy_configuration).predefined_metric_specification).predefined_metric_type == "ALBRequestCountPerTarget",
+      length(one(aws_appautoscaling_policy.gateway_requests[0].target_tracking_scaling_policy_configuration).customized_metric_specification) == 0,
+    ])
+    error_message = "The request policy must track ALBRequestCountPerTarget at 60 times the configured requests per second per task."
+  }
+}
+
+run "tokens_per_second_adds_a_metric_math_policy" {
+  command = plan
+
+  variables {
+    gateway_target_tokens_per_second = 6000000
+    gateway_tokens_metric = {
+      namespace  = "LiteLLM/Prometheus"
+      dimensions = { ClusterName = "acme-litellm-test", TaskDefinitionFamily = "acme-litellm-test-gateway" }
+    }
+  }
+
+  assert {
+    condition     = length(aws_appautoscaling_policy.gateway_tokens) == 1 && length(aws_appautoscaling_policy.gateway_requests) == 0
+    error_message = "A token target alone must add exactly the token policy."
+  }
+
+  assert {
+    condition = alltrue([
+      aws_appautoscaling_policy.gateway_tokens[0].name == "acme-litellm-test-gateway-tokens",
+      aws_appautoscaling_policy.gateway_tokens[0].resource_id == "service/acme-litellm-test/acme-litellm-test-gateway",
+      one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).target_value == 6000000,
+      length(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).predefined_metric_specification) == 0,
+    ])
+    error_message = "The token policy must track a customized metric at the configured tokens per second per task."
+  }
+
+  assert {
+    condition = alltrue([
+      length(one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics) == 4,
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].id == "tokens",
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].return_data == false,
+      one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].metric_stat).stat == "Sum",
+      one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].metric_stat).metric).namespace == "LiteLLM/Prometheus",
+      one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].metric_stat).metric).metric_name == "litellm_total_tokens_metric_total",
+      { for d in one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].metric_stat).metric).dimensions : d.name => d.value } == { ClusterName = "acme-litellm-test", TaskDefinitionFamily = "acme-litellm-test-gateway" },
+    ])
+    error_message = "The first metric must sum the published token counter deltas under the configured namespace and dimensions."
+  }
+
+  assert {
+    condition = alltrue([
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["running_tasks"].id == "running_tasks",
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["running_tasks"].return_data == false,
+      one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["running_tasks"].metric_stat).stat == "Average",
+      one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["running_tasks"].metric_stat).metric).namespace == "ECS/ContainerInsights",
+      one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["running_tasks"].metric_stat).metric).metric_name == "RunningTaskCount",
+      { for d in one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["running_tasks"].metric_stat).metric).dimensions : d.name => d.value } == { ClusterName = "acme-litellm-test", ServiceName = "acme-litellm-test-gateway" },
+    ])
+    error_message = "The second metric must read the gateway service's Container Insights RunningTaskCount."
+  }
+
+  assert {
+    condition = alltrue([
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens_per_second"].expression == "tokens / 60",
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens_per_second"].return_data == false,
+    ])
+    error_message = "The 60s period Sum must be divided by 60 to yield tokens per second."
+  }
+
+  assert {
+    condition = alltrue([
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens_per_second_per_task"].expression == "tokens_per_second / running_tasks",
+      { for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens_per_second_per_task"].return_data == true,
+      length([for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m if m.return_data]) == 1,
+    ])
+    error_message = "Only the per-task tokens per second may return data to the scaling policy."
+  }
+}
+
+run "tokens_per_second_needs_the_metric_location" {
+  command = plan
+
+  variables {
+    gateway_target_tokens_per_second = 6000000
+  }
+
+  expect_failures = [
+    aws_appautoscaling_policy.gateway_tokens,
+  ]
+}
+
+run "requests_and_tokens_scale_next_to_cpu_and_memory" {
+  command = plan
+
+  variables {
+    gateway_target_requests_per_second = 90
+    gateway_target_tokens_per_second   = 6000000
+    gateway_tokens_metric              = { namespace = "LiteLLM/Prometheus" }
+  }
+
+  assert {
+    condition = alltrue([
+      length(aws_appautoscaling_policy.gateway_cpu) == 1,
+      length(aws_appautoscaling_policy.gateway_memory) == 1,
+      length(aws_appautoscaling_policy.gateway_requests) == 1,
+      length(aws_appautoscaling_policy.gateway_tokens) == 1,
+      one(aws_appautoscaling_policy.gateway_cpu[0].target_tracking_scaling_policy_configuration).target_value == 70,
+      one(aws_appautoscaling_policy.gateway_memory[0].target_tracking_scaling_policy_configuration).target_value == 80,
+    ])
+    error_message = "Workload policies must coexist with the CPU and memory policies at their default targets."
+  }
+
+  assert {
+    condition     = length(one(one({ for m in one(one(aws_appautoscaling_policy.gateway_tokens[0].target_tracking_scaling_policy_configuration).customized_metric_specification).metrics : m.id => m }["tokens"].metric_stat).metric).dimensions) == 0
+    error_message = "Omitting dimensions must query the token metric without any."
+  }
+}
+
+run "workload_targets_are_ignored_when_autoscaling_is_off" {
+  command = plan
+
+  variables {
+    gateway_autoscaling_enabled        = false
+    gateway_target_requests_per_second = 90
+    gateway_target_tokens_per_second   = 6000000
+    gateway_tokens_metric              = { namespace = "LiteLLM/Prometheus" }
+  }
+
+  assert {
+    condition = alltrue([
+      length(aws_appautoscaling_target.gateway) == 0,
+      length(aws_appautoscaling_policy.gateway_requests) == 0,
+      length(aws_appautoscaling_policy.gateway_tokens) == 0,
+    ])
+    error_message = "Disabling gateway autoscaling must drop the workload policies with the target."
+  }
+}
diff --git a/terraform/litellm/aws/variables.tf b/terraform/litellm/aws/variables.tf
index 667f6db63c9..580a0cc657a 100644
--- a/terraform/litellm/aws/variables.tf
+++ b/terraform/litellm/aws/variables.tf
@@ -200,6 +200,44 @@ variable "gateway_num_workers" {
   }
 }
 
+variable "gateway_connection_pool_enabled" {
+  description = <<-EOT
+    Run an in-container PgBouncer (transaction mode, loopback) in each gateway
+    task, shared by every uvicorn worker. Without it each of the
+    `gateway_num_workers` workers opens its own Prisma pool straight to
+    Postgres, so a task's footprint against the database connection ceiling is
+    workers x connection_limit and grows with every task. Sets
+    LITELLM_PGBOUNCER_ENABLED / LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS /
+    LITELLM_PGBOUNCER_MAX_CLIENT_CONN on the gateway container only. Works with
+    the module-created Aurora too: the pooler mints the IAM token itself and
+    renews it before it expires.
+  EOT
+  type        = bool
+  default     = false
+}
+
+variable "gateway_pool_max_db_connections" {
+  description = "Upstream Postgres connections one gateway task may hold when gateway_connection_pool_enabled is set, regardless of gateway_num_workers. 20 suits 4 workers; a 5000-connection database then fits roughly 200 tasks."
+  type        = number
+  default     = 20
+
+  validation {
+    condition     = var.gateway_pool_max_db_connections >= 1
+    error_message = "gateway_pool_max_db_connections must be >= 1."
+  }
+}
+
+variable "gateway_pool_max_client_conn" {
+  description = "Client connections the in-container PgBouncer accepts from the gateway workers when gateway_connection_pool_enabled is set."
+  type        = number
+  default     = 1000
+
+  validation {
+    condition     = var.gateway_pool_max_client_conn >= 1
+    error_message = "gateway_pool_max_client_conn must be >= 1."
+  }
+}
+
 variable "backend_cpu" {
   description = "Fargate CPU units for the backend task (1024 = 1 vCPU)."
   type        = number
@@ -272,6 +310,47 @@ variable "gateway_memory_target" {
   default     = 80
 }
 
+variable "gateway_target_requests_per_second" {
+  description = <<-EOT
+    Requests per second one gateway task should serve. Adds an
+    ALBRequestCountPerTarget target-tracking policy next to the CPU/memory
+    ones (Application Auto Scaling follows whichever asks for more tasks).
+    CloudWatch publishes that metric as a 1-minute count, so the policy
+    targets 60x this value and ECS reacts on a ~1 minute cadence. 0 skips
+    the policy.
+  EOT
+  type        = number
+  default     = 0
+}
+
+variable "gateway_target_tokens_per_second" {
+  description = <<-EOT
+    Tokens per second one gateway task should serve. Adds a target-tracking
+    policy on gateway_tokens_metric summed over each 60s period, divided by
+    60 and by the service's Container Insights RunningTaskCount. Tokens are
+    counted when a response completes, so the signal trails long streams.
+    0 skips the policy.
+  EOT
+  type        = number
+  default     = 0
+}
+
+variable "gateway_tokens_metric" {
+  description = <<-EOT
+    CloudWatch metric carrying the gateway's litellm_total_tokens_metric_total
+    counter, as published by the CloudWatch agent's Prometheus scraper (it
+    emits the delta between scrapes, so Sum over a period is the tokens
+    served in it). Required when gateway_target_tokens_per_second > 0.
+    dimensions must match the metric_declaration the agent publishes with.
+  EOT
+  type = object({
+    namespace  = string
+    name       = optional(string, "litellm_total_tokens_metric_total")
+    dimensions = optional(map(string), {})
+  })
+  default = null
+}
+
 variable "backend_autoscaling_enabled" {
   description = "Toggle Application Auto Scaling target-tracking on the backend service."
   type        = bool
@@ -729,3 +808,73 @@ variable "billing_metrics_ca_cert_pem" {
   default     = ""
   sensitive   = true
 }
+
+# ---------- Collector sidecar ----------
+#
+# Opt-in offload of spend tracking from the gateway's uvicorn workers to a
+# `python -m litellm.proxy.collector` sidecar in the same Fargate task (helm's
+# `gateway.collector`). Fargate awsvpc tasks share one network namespace,
+# so the sidecar listens on loopback TCP. Disabled (the default) adds nothing
+# to the task definition.
+
+variable "collector_enabled" {
+  description = "Run the collector sidecar next to the gateway container and have the gateway ship spend events to it (sets LITELLM_COLLECTOR_ENABLED=true on both). Autoscaling still targets the whole task's CPU/memory, sidecar included."
+  type        = bool
+  default     = false
+}
+
+variable "collector_port" {
+  description = "Loopback TCP port the sidecar listens on (LITELLM_COLLECTOR_ADDRESS=tcp://127.0.0.1:<port>)."
+  type        = number
+  default     = 4010
+
+  validation {
+    condition     = var.collector_port >= 1024 && var.collector_port <= 65535 && var.collector_port != 4000
+    error_message = "collector_port must be in 1024-65535 and not 4000."
+  }
+}
+
+variable "collector_cpu" {
+  description = "CPU units reserved for the sidecar container, carved out of gateway_cpu. Matches helm's collector.resources.requests.cpu (500m)."
+  type        = number
+  default     = 512
+}
+
+variable "collector_memory" {
+  description = "Hard memory limit (MiB) for the sidecar container, carved out of gateway_memory. Matches helm's collector.resources.limits.memory (2Gi)."
+  type        = number
+  default     = 2048
+}
+
+variable "collector_buffer_size" {
+  description = "Per-worker in-memory queue of spend events waiting to be shipped to the sidecar (LITELLM_COLLECTOR_BUFFER_SIZE)."
+  type        = number
+  default     = 1000
+
+  validation {
+    condition     = var.collector_buffer_size >= 1
+    error_message = "collector_buffer_size must be >= 1."
+  }
+}
+
+variable "collector_on_unavailable" {
+  description = "What the gateway does with spend events when the sidecar is unreachable or the buffer is full (LITELLM_COLLECTOR_ON_UNAVAILABLE): `fallback` runs the pipeline in-process, `drop` discards them."
+  type        = string
+  default     = "fallback"
+
+  validation {
+    condition     = contains(["fallback", "drop"], var.collector_on_unavailable)
+    error_message = "collector_on_unavailable must be one of: fallback, drop."
+  }
+}
+
+variable "collector_drain_timeout_seconds" {
+  description = "Seconds a gateway worker waits on shutdown for its buffered spend events to reach the sidecar (LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS)."
+  type        = number
+  default     = 10
+
+  validation {
+    condition     = var.collector_drain_timeout_seconds > 0
+    error_message = "collector_drain_timeout_seconds must be > 0."
+  }
+}
diff --git a/terraform/litellm/gcp/README.md b/terraform/litellm/gcp/README.md
index c93e5f6b303..4b2f576adc1 100644
--- a/terraform/litellm/gcp/README.md
+++ b/terraform/litellm/gcp/README.md
@@ -238,6 +238,129 @@ this with `litellm_license`. To tune the export cadence, set
 
 Behavior matches the AWS stack 1:1; the variable names are identical
 
+### Prometheus metrics sidecar
+
+`gateway_metrics_port` adds a `metrics` sidecar
+(`python -m litellm.proxy.prometheus_metrics_server`) to the gateway Cloud Run
+service that aggregates the workers' samples over an in-memory volume shared
+with the gateway container, so the collector's scrape never runs on an
+inference worker. Cloud Run only routes traffic to the gateway container, so
+the load balancer keeps hitting port 4000 (including the gateway's own
+authenticated `/metrics`, which stays as it was) and the sidecar port is
+reachable on localhost inside the instance only. To get the series out, the
+stack also adds Google's
+[Managed Service for Prometheus sidecar](https://cloud.google.com/stackdriver/docs/managed-prometheus/cloudrun-sidecar)
+(`gateway_metrics_collector_image`) with a `RunMonitoring` config stored in
+Secret Manager that scrapes `localhost:<port>/metrics` every 30s and writes to
+Cloud Monitoring as `prometheus.googleapis.com/...` metrics. Enabling it grants
+the runtime service account `roles/monitoring.metricWriter` and
+`roles/logging.logWriter` on the project. Needs `gateway_image` v1.101.0 or
+newer. See [Prometheus metrics](https://docs.litellm.ai/docs/proxy/prometheus)
+for the metrics themselves
+
+```hcl
+gateway_metrics_port = 4001
+```
+
+The collector scrapes from inside the instance, so scrapes on an instance with
+no in-flight requests can fail when CPU is throttled between requests. Keep
+`gateway_min_instances` at 1 or more and, if you see gaps, enable
+instance-based billing on the gateway service. Unlike the AWS stack there is
+no `gateway_metrics_scrape_cidrs`: nothing outside the instance can reach the
+sidecar port, so there is no network rule to open
+
+### Autoscaling
+
+Cloud Run scales the gateway on request concurrency (plus its built-in CPU
+target), not on a metric you attach. Each instance takes up to
+`gateway_max_instance_request_concurrency` requests at once (default 80)
+and Cloud Run adds instances between `gateway_min_instances` and
+`gateway_max_instances` when the in-flight count fills up. That is the
+request-rate signal for this stack: lower the concurrency for LLM streams
+that hold a worker for tens of seconds, since a stream counts as one request
+for as long as it is open
+
+There is no tokens-per-second path here. Cloud Run's autoscaler has no
+custom-metric input, so the `litellm_total_tokens_metric_total` counter the
+proxy exposes cannot drive it. If you need token-based scaling on GCP, run
+the gateway on GKE with the Helm chart's `targetTokensPerSecond` (see
+"Dependencies only" below) rather than wiring the counter into Cloud
+Monitoring, which the autoscaler would ignore
+
+### In-container connection pool
+
+Each of the `gateway_num_workers` uvicorn workers opens its own Prisma pool
+straight to Cloud SQL, so one instance holds `workers x connection_limit`
+connections and the fleet's footprint against the database ceiling grows with
+every instance Cloud Run adds. `gateway_connection_pool_enabled` runs a
+PgBouncer (transaction mode, loopback) inside the gateway container that all
+workers share, capping the instance at `gateway_pool_max_db_connections`
+upstream connections however many workers it runs.
+`gateway_pool_max_client_conn` bounds the worker-side connections the pooler
+accepts. The module sets `LITELLM_PGBOUNCER_ENABLED`,
+`LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS` and `LITELLM_PGBOUNCER_MAX_CLIENT_CONN`
+on the gateway service only; the backend service and the migrations job keep
+the direct connection
+
+```hcl
+gateway_num_workers             = 4
+gateway_connection_pool_enabled = true
+gateway_pool_max_db_connections = 20
+gateway_pool_max_client_conn    = 1000
+```
+
+The pooler holds one static database password for the life of the instance.
+This stack authenticates to Cloud SQL with the Secret Manager password (see
+[Database authentication](#database-authentication)), so nothing else is
+needed; a Cloud SQL Auth Proxy sidecar with IAM auth would not work with the
+pool
+
+The gateway container starts through `python -m gateway.launch` (the
+componentized image's own entrypoint) rather than `uvicorn` directly. The
+launcher reads these variables, starts the pooler once per instance before
+uvicorn forks the workers and hands them its loopback `DATABASE_URL`. It also
+honours `KEEPALIVE_TIMEOUT` from `gateway_extra_env` the way the image does
+
+### Collector sidecar
+
+`collector_enabled = true` adds a `spend-collector` container to the gateway
+Cloud Run service that runs `python -m litellm.proxy.collector` from the gateway
+image, and sets `LITELLM_COLLECTOR_ENABLED=true` on the gateway so its
+uvicorn workers ship spend events (SpendLogs writes, key/team/user spend
+updates, budget alerts) to the sidecar instead of running that pipeline in
+the request path. This is the Terraform counterpart of helm's
+`gateway.collector`. The default (`false`) leaves the service exactly as
+before. It is independent of the metrics sidecars above, whose GMP scraper
+already owns the `collector` container name.
+
+Containers in one Cloud Run instance share localhost, so the sidecar listens
+on loopback TCP (`tcp://127.0.0.1:${collector_port}`, default 4010)
+instead of the Unix socket helm uses; the proxy rejects any non-loopback
+address. The sidecar runs the same Redis CA + `DATABASE_URL` bootstrap as
+the gateway container, gets the same database, Redis, master-key, license,
+proxy config, and `gateway_extra_env` / `gateway_extra_secrets` values, and
+runs with `LITELLM_JOB_ROLE=collector`. With `gateway_connection_pool_enabled`
+it also gets the `LITELLM_PGBOUNCER_*` env, so its Prisma client goes through
+the instance-local PgBouncer instead of opening a second pool straight to the
+database. When it is unreachable the gateway falls back to in-process spend
+tracking.
+
+```hcl
+collector_enabled = true
+# collector_cpu               = "1000m"  # added on top of gateway_cpu
+# collector_memory            = "2Gi"    # added on top of gateway_memory
+# collector_buffer_size       = 1000
+# collector_on_unavailable    = "fallback"  # or "drop"
+# collector_drain_timeout_seconds = 10
+```
+
+Cloud Run allocates CPU per instance while requests are in flight, and the
+sidecar shares that allocation. Spend events are shipped right after each
+response, so this works with request-based billing, but keep
+`gateway_min_instances >= 1` if spend must keep draining while an instance
+is otherwise idle. Variable names match the AWS stack; only the resource
+units differ (Cloud Run strings vs Fargate units)
+
 ## Tenant deployment
 
 Every resource the stack creates is named `${tenant}-litellm-${env}` (or
diff --git a/terraform/litellm/gcp/cloudrun.tf b/terraform/litellm/gcp/cloudrun.tf
index 84ae8b9247f..d0b32a367d6 100644
--- a/terraform/litellm/gcp/cloudrun.tf
+++ b/terraform/litellm/gcp/cloudrun.tf
@@ -138,10 +138,16 @@ locals {
     "export DATABASE_URL_READ_REPLICA=\"postgresql://$${DATABASE_USER}:$${DATABASE_PASSWORD}@$${DATABASE_HOST_READ_REPLICA}:$${DATABASE_PORT_READ_REPLICA}/$${DATABASE_NAME}\"",
   ]
 
+  gateway_pool_env = var.gateway_connection_pool_enabled ? [
+    { name = "LITELLM_PGBOUNCER_ENABLED", value = "true" },
+    { name = "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS", value = tostring(var.gateway_pool_max_db_connections) },
+    { name = "LITELLM_PGBOUNCER_MAX_CLIENT_CONN", value = tostring(var.gateway_pool_max_client_conn) },
+  ] : []
+
   gateway_uvicorn_args = "--host 0.0.0.0 --port 4000 --workers ${var.gateway_num_workers}"
   backend_uvicorn_args = "--host 0.0.0.0 --port 4001"
 
-  gateway_launch_cmd = "case \"$USE_DDTRACE\" in [Tt][Rr][Uu][Ee]) export DD_TRACE_OPENAI_ENABLED=\"False\"; exec ddtrace-run uvicorn gateway.main:app ${local.gateway_uvicorn_args};; *) exec uvicorn gateway.main:app ${local.gateway_uvicorn_args};; esac"
+  gateway_launch_cmd = "case \"$USE_DDTRACE\" in [Tt][Rr][Uu][Ee]) export DD_TRACE_OPENAI_ENABLED=\"False\"; exec ddtrace-run python -m gateway.launch ${local.gateway_uvicorn_args};; *) exec python -m gateway.launch ${local.gateway_uvicorn_args};; esac"
   backend_launch_cmd = "case \"$USE_DDTRACE\" in [Tt][Rr][Uu][Ee]) export DD_TRACE_OPENAI_ENABLED=\"False\"; exec ddtrace-run uvicorn backend.main:app ${local.backend_uvicorn_args};; *) exec uvicorn backend.main:app ${local.backend_uvicorn_args};; esac"
 
   gateway_args = join(" && ", concat(
@@ -150,12 +156,55 @@ locals {
     [local.gateway_launch_cmd],
   ))
 
+  metrics_enabled       = var.create_runtime && var.gateway_metrics_port != null
+  metrics_multiproc_dir = "/tmp/litellm_prometheus_multiproc"
+  metrics_volume        = "prometheus-multiproc"
+  metrics_env_kv        = local.metrics_enabled ? [{ name = "PROMETHEUS_MULTIPROC_DIR", value = local.metrics_multiproc_dir }] : []
+  metrics_config_volume = "gmp-config"
+
+  metrics_run_monitoring_yaml = local.metrics_enabled ? yamlencode({
+    apiVersion = "monitoring.googleapis.com/v1beta"
+    kind       = "RunMonitoring"
+    metadata   = { name = "${local.name}-gateway" }
+    spec = {
+      endpoints = [{ port = var.gateway_metrics_port, path = "/metrics", interval = "30s" }]
+    }
+  }) : ""
+
   backend_args = join(" && ", concat(
     local.redis_ca_fragment,
     local.database_url_fragment,
     [local.backend_launch_cmd],
   ))
 
+  collector_address = "tcp://127.0.0.1:${var.collector_port}"
+  collector_env_kv = var.collector_enabled ? [
+    { name = "LITELLM_COLLECTOR_ENABLED", value = "true" },
+    { name = "LITELLM_COLLECTOR_ADDRESS", value = local.collector_address },
+    { name = "LITELLM_COLLECTOR_BUFFER_SIZE", value = tostring(var.collector_buffer_size) },
+    { name = "LITELLM_COLLECTOR_ON_UNAVAILABLE", value = var.collector_on_unavailable },
+    { name = "LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS", value = tostring(var.collector_drain_timeout_seconds) },
+  ] : []
+
+  gateway_env_kv      = concat(local.shared_env_kv, local.gateway_otel_env_kv, local.billing_metrics_env_kv, local.gateway_extra_env_kv, local.proxy_config_env, local.metrics_env_kv, local.gateway_pool_env, local.collector_env_kv)
+  gateway_env_secrets = concat(local.shared_env_secrets, local.otel_env_secrets, local.billing_metrics_env_secrets, local.gateway_extra_secret_kv)
+
+  collector_env_kv_all = concat(
+    local.shared_env_kv,
+    local.gateway_extra_env_kv,
+    local.proxy_config_env,
+    local.gateway_pool_env,
+    local.collector_env_kv,
+    [{ name = "LITELLM_JOB_ROLE", value = "collector" }],
+  )
+  collector_env_secrets = concat(local.shared_env_secrets, local.gateway_extra_secret_kv)
+
+  collector_args = join(" && ", concat(
+    local.redis_ca_fragment,
+    local.database_url_fragment,
+    ["exec python -m litellm.proxy.collector"],
+  ))
+
   # Env shipped to the migrations Job. The migrations image runs run.py
   # which assembles DATABASE_URL from these discrete vars itself, so we
   # only need writer-side DB env (no read replica, no proxy_config, no
@@ -182,6 +231,13 @@ resource "google_cloud_run_v2_service" "gateway" {
   labels              = local.labels
   deletion_protection = false
 
+  lifecycle {
+    precondition {
+      condition     = !var.collector_enabled || var.gateway_metrics_port == null || var.collector_port != var.gateway_metrics_port
+      error_message = "collector_port and gateway_metrics_port must differ: both sidecars bind loopback in the same instance."
+    }
+  }
+
   template {
     service_account                  = google_service_account.runtime.email
     max_instance_request_concurrency = var.gateway_max_instance_request_concurrency
@@ -197,6 +253,7 @@ resource "google_cloud_run_v2_service" "gateway" {
     }
 
     containers {
+      name    = "gateway"
       image   = local.gateway_image
       command = ["sh", "-c"]
       args    = [local.gateway_args]
@@ -213,7 +270,7 @@ resource "google_cloud_run_v2_service" "gateway" {
       }
 
       dynamic "env" {
-        for_each = concat(local.shared_env_kv, local.gateway_otel_env_kv, local.billing_metrics_env_kv, local.gateway_extra_env_kv, local.proxy_config_env)
+        for_each = local.gateway_env_kv
         content {
           name  = env.value.name
           value = env.value.value
@@ -221,7 +278,7 @@ resource "google_cloud_run_v2_service" "gateway" {
       }
 
       dynamic "env" {
-        for_each = concat(local.shared_env_secrets, local.otel_env_secrets, local.billing_metrics_env_secrets, local.gateway_extra_secret_kv)
+        for_each = local.gateway_env_secrets
         content {
           name = env.value.name
           value_source {
@@ -241,6 +298,14 @@ resource "google_cloud_run_v2_service" "gateway" {
         }
       }
 
+      dynamic "volume_mounts" {
+        for_each = local.metrics_enabled ? [1] : []
+        content {
+          name       = local.metrics_volume
+          mount_path = local.metrics_multiproc_dir
+        }
+      }
+
       startup_probe {
         http_get {
           path = "/health/readiness"
@@ -262,6 +327,117 @@ resource "google_cloud_run_v2_service" "gateway" {
       }
     }
 
+    dynamic "containers" {
+      for_each = local.metrics_enabled ? [1] : []
+      content {
+        name    = "metrics"
+        image   = local.gateway_image
+        command = ["python", "-m", "litellm.proxy.prometheus_metrics_server"]
+        args    = ["--port", tostring(var.gateway_metrics_port)]
+
+        dynamic "env" {
+          for_each = local.metrics_env_kv
+          content {
+            name  = env.value.name
+            value = env.value.value
+          }
+        }
+
+        volume_mounts {
+          name       = local.metrics_volume
+          mount_path = local.metrics_multiproc_dir
+        }
+
+        startup_probe {
+          http_get {
+            path = "/health"
+            port = var.gateway_metrics_port
+          }
+          period_seconds    = 5
+          timeout_seconds   = 3
+          failure_threshold = 12
+        }
+
+        liveness_probe {
+          http_get {
+            path = "/health"
+            port = var.gateway_metrics_port
+          }
+          period_seconds  = 30
+          timeout_seconds = 5
+        }
+      }
+    }
+
+    dynamic "containers" {
+      for_each = local.metrics_enabled ? [1] : []
+      content {
+        name       = "collector"
+        image      = var.gateway_metrics_collector_image
+        depends_on = ["metrics"]
+
+        volume_mounts {
+          name       = local.metrics_config_volume
+          mount_path = "/etc/rungmp"
+        }
+
+        liveness_probe {
+          http_get {
+            path = "/liveness"
+            port = 13133
+          }
+          period_seconds  = 30
+          timeout_seconds = 30
+        }
+      }
+    }
+
+    dynamic "containers" {
+      for_each = var.collector_enabled ? [1] : []
+      content {
+        name    = "spend-collector"
+        image   = local.gateway_image
+        command = ["sh", "-c"]
+        args    = [local.collector_args]
+
+        resources {
+          limits = {
+            cpu    = var.collector_cpu
+            memory = var.collector_memory
+          }
+        }
+
+        dynamic "env" {
+          for_each = local.collector_env_kv_all
+          content {
+            name  = env.value.name
+            value = env.value.value
+          }
+        }
+
+        dynamic "env" {
+          for_each = local.collector_env_secrets
+          content {
+            name = env.value.name
+            value_source {
+              secret_key_ref {
+                secret  = env.value.secret
+                version = env.value.version
+              }
+            }
+          }
+        }
+
+        dynamic "volume_mounts" {
+          for_each = local.proxy_config_enabled ? [1] : []
+          content {
+            name       = local.proxy_config_volume
+            mount_path = local.proxy_config_mount_path
+          }
+        }
+      }
+    }
+
     dynamic "volumes" {
       for_each = local.proxy_config_enabled ? [1] : []
       content {
@@ -272,6 +448,31 @@ resource "google_cloud_run_v2_service" "gateway" {
         }
       }
     }
+
+    dynamic "volumes" {
+      for_each = local.metrics_enabled ? [1] : []
+      content {
+        name = local.metrics_volume
+        empty_dir {
+          medium     = "MEMORY"
+          size_limit = "256Mi"
+        }
+      }
+    }
+
+    dynamic "volumes" {
+      for_each = local.metrics_enabled ? [1] : []
+      content {
+        name = local.metrics_config_volume
+        secret {
+          secret = google_secret_manager_secret.metrics_run_monitoring[0].secret_id
+          items {
+            version = "latest"
+            path    = "config.yaml"
+          }
+        }
+      }
+    }
   }
 
   depends_on = [
@@ -283,6 +484,8 @@ resource "google_cloud_run_v2_service" "gateway" {
     google_secret_manager_secret_iam_member.billing_metrics_client_cert,
     google_secret_manager_secret_iam_member.billing_metrics_client_key,
     google_secret_manager_secret_iam_member.billing_metrics_ca_cert,
+    google_secret_manager_secret_iam_member.metrics_run_monitoring,
+    google_project_iam_member.runtime_metric_writer,
     google_storage_bucket_iam_member.proxy_config_runtime,
     google_sql_user.app,
     # Don't go live until the schema is migrated; otherwise the proxy boots,
@@ -332,7 +535,7 @@ resource "google_cloud_run_v2_service" "backend" {
       }
 
       dynamic "env" {
-        for_each = concat(local.shared_env_kv, local.backend_default_env_kv, local.backend_otel_env_kv, local.billing_metrics_env_kv, local.backend_extra_env_kv, local.proxy_config_env)
+        for_each = concat(local.shared_env_kv, local.backend_default_env_kv, local.backend_otel_env_kv, local.billing_metrics_env_kv, local.backend_extra_env_kv, local.proxy_config_env, local.metrics_env_kv)
         content {
           name  = env.value.name
           value = env.value.value
diff --git a/terraform/litellm/gcp/examples/default/main.tf b/terraform/litellm/gcp/examples/default/main.tf
index f44b2a9a001..782d4ee4b65 100644
--- a/terraform/litellm/gcp/examples/default/main.tf
+++ b/terraform/litellm/gcp/examples/default/main.tf
@@ -53,4 +53,6 @@ module "litellm" {
   backend_extra_env     = var.backend_extra_env
   gateway_extra_secrets = var.gateway_extra_secrets
   backend_extra_secrets = var.backend_extra_secrets
+
+  gateway_metrics_port = var.gateway_metrics_port
 }
diff --git a/terraform/litellm/gcp/examples/default/terraform.tfvars.example b/terraform/litellm/gcp/examples/default/terraform.tfvars.example
index c35206503bb..ec6206734e2 100644
--- a/terraform/litellm/gcp/examples/default/terraform.tfvars.example
+++ b/terraform/litellm/gcp/examples/default/terraform.tfvars.example
@@ -107,3 +107,9 @@ env    = "stage"
 # main.tf (otel_endpoint, otel_exporter, otel_environment_name,
 # otel_capture_message_content, otel_headers_secret). Full docs in
 # ../../variables.tf.
+
+# ---------- Prometheus metrics sidecar ----------
+# Serve /metrics from a sidecar in the gateway service instead of the inference
+# workers. Scraped inside the instance by the Managed Service for Prometheus
+# sidecar and written to Cloud Monitoring; see ../../README.md.
+# gateway_metrics_port = 4001
diff --git a/terraform/litellm/gcp/examples/default/variables.tf b/terraform/litellm/gcp/examples/default/variables.tf
index 88b57ce27eb..08b78346df3 100644
--- a/terraform/litellm/gcp/examples/default/variables.tf
+++ b/terraform/litellm/gcp/examples/default/variables.tf
@@ -142,3 +142,9 @@ variable "backend_extra_secrets" {
   type        = map(string)
   default     = {}
 }
+
+variable "gateway_metrics_port" {
+  description = "Port for the Prometheus metrics sidecar in the gateway service. Null keeps /metrics on the gateway port only."
+  type        = number
+  default     = null
+}
diff --git a/terraform/litellm/gcp/iam.tf b/terraform/litellm/gcp/iam.tf
index 509e6d48ffd..5c2bc38bc12 100644
--- a/terraform/litellm/gcp/iam.tf
+++ b/terraform/litellm/gcp/iam.tf
@@ -116,3 +116,27 @@ resource "google_secret_manager_secret_iam_member" "billing_metrics_ca_cert" {
   role      = "roles/secretmanager.secretAccessor"
   member    = "serviceAccount:${google_service_account.runtime.email}"
 }
+
+resource "google_secret_manager_secret_iam_member" "metrics_run_monitoring" {
+  count = local.metrics_enabled ? 1 : 0
+
+  secret_id = google_secret_manager_secret.metrics_run_monitoring[0].id
+  role      = "roles/secretmanager.secretAccessor"
+  member    = "serviceAccount:${google_service_account.runtime.email}"
+}
+
+resource "google_project_iam_member" "runtime_metric_writer" {
+  count = local.metrics_enabled ? 1 : 0
+
+  project = var.project_id
+  role    = "roles/monitoring.metricWriter"
+  member  = "serviceAccount:${google_service_account.runtime.email}"
+}
+
+resource "google_project_iam_member" "runtime_log_writer" {
+  count = local.metrics_enabled ? 1 : 0
+
+  project = var.project_id
+  role    = "roles/logging.logWriter"
+  member  = "serviceAccount:${google_service_account.runtime.email}"
+}
diff --git a/terraform/litellm/gcp/secrets.tf b/terraform/litellm/gcp/secrets.tf
index 6ec77139996..b3b656721ab 100644
--- a/terraform/litellm/gcp/secrets.tf
+++ b/terraform/litellm/gcp/secrets.tf
@@ -118,3 +118,20 @@ resource "google_secret_manager_secret_version" "billing_metrics_ca_cert" {
   secret      = google_secret_manager_secret.billing_metrics_ca_cert[0].id
   secret_data = var.billing_metrics_ca_cert_pem
 }
+
+resource "google_secret_manager_secret" "metrics_run_monitoring" {
+  count = local.metrics_enabled ? 1 : 0
+
+  secret_id = "${local.name}-gateway-run-monitoring"
+  labels    = local.labels
+  replication {
+    auto {}
+  }
+}
+
+resource "google_secret_manager_secret_version" "metrics_run_monitoring" {
+  count = local.metrics_enabled ? 1 : 0
+
+  secret      = google_secret_manager_secret.metrics_run_monitoring[0].id
+  secret_data = local.metrics_run_monitoring_yaml
+}
diff --git a/terraform/litellm/gcp/tests/collector.tftest.hcl b/terraform/litellm/gcp/tests/collector.tftest.hcl
new file mode 100644
index 00000000000..7a5ea781acb
--- /dev/null
+++ b/terraform/litellm/gcp/tests/collector.tftest.hcl
@@ -0,0 +1,165 @@
+# Plan-only coverage for the opt-in collector sidecar on the gateway Cloud
+# Run service. `mock_provider` keeps this offline: no GCP credentials, no API
+# calls. Run from terraform/litellm/gcp with `terraform test`.
+
+mock_provider "google" {}
+mock_provider "google-beta" {}
+mock_provider "random" {}
+
+variables {
+  project_id         = "acme-test"
+  region             = "us-central1"
+  tenant             = "acme"
+  env                = "test"
+  allow_plaintext_lb = true
+}
+
+run "disabled_by_default_leaves_the_service_untouched" {
+  command = plan
+
+  assert {
+    condition     = [for c in google_cloud_run_v2_service.gateway[0].template[0].containers : c.name] == ["gateway"]
+    error_message = "The gateway service must stay single-container unless collector_enabled is set."
+  }
+
+  assert {
+    condition = !anytrue([
+      for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : startswith(e.name, "LITELLM_COLLECTOR_")
+    ])
+    error_message = "No LITELLM_COLLECTOR_* env may reach the gateway while the sidecar is disabled."
+  }
+}
+
+run "enabled_adds_a_sidecar_that_shares_the_gateway_transport" {
+  command = plan
+
+  variables {
+    collector_enabled        = true
+    collector_port           = 4321
+    collector_buffer_size    = 250
+    collector_on_unavailable = "drop"
+    collector_cpu            = "500m"
+    collector_memory         = "1Gi"
+    gateway_extra_env        = { OPENAI_API_BASE = "https://example.invalid" }
+    gateway_extra_secrets    = { OPENAI_API_KEY = "projects/acme-test/secrets/openai-api-key" }
+  }
+
+  assert {
+    condition     = [for c in google_cloud_run_v2_service.gateway[0].template[0].containers : c.name] == ["gateway", "spend-collector"]
+    error_message = "Enabling the sidecar must append a spend-collector container after the gateway container."
+  }
+
+  assert {
+    condition = alltrue([
+      for c in google_cloud_run_v2_service.gateway[0].template[0].containers : (
+        { for e in c.env : e.name => e.value }["LITELLM_COLLECTOR_ENABLED"] == "true" &&
+        { for e in c.env : e.name => e.value }["LITELLM_COLLECTOR_ADDRESS"] == "tcp://127.0.0.1:4321" &&
+        { for e in c.env : e.name => e.value }["LITELLM_COLLECTOR_BUFFER_SIZE"] == "250" &&
+        { for e in c.env : e.name => e.value }["LITELLM_COLLECTOR_ON_UNAVAILABLE"] == "drop" &&
+        { for e in c.env : e.name => e.value }["LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS"] == "10"
+      )
+    ])
+    error_message = "Gateway and sidecar must agree on the loopback address and the collector knobs."
+  }
+
+  assert {
+    condition = (
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].image == local.gateway_image &&
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].command == tolist(["sh", "-c"]) &&
+      endswith(google_cloud_run_v2_service.gateway[0].template[0].containers[1].args[0], " && exec python -m litellm.proxy.collector") &&
+      strcontains(google_cloud_run_v2_service.gateway[0].template[0].containers[1].args[0], "export DATABASE_URL=") &&
+      strcontains(google_cloud_run_v2_service.gateway[0].template[0].containers[1].args[0], "REDIS_SSL_CA_CERTS") &&
+      { for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name => e.value }["LITELLM_JOB_ROLE"] == "collector"
+    )
+    error_message = "The sidecar must run litellm.proxy.collector from the gateway image with the same Redis CA + DATABASE_URL bootstrap as the gateway."
+  }
+
+  assert {
+    condition = (
+      length(google_cloud_run_v2_service.gateway[0].template[0].containers[1].ports) == 0 &&
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].resources[0].limits.cpu == "500m" &&
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].resources[0].limits.memory == "1Gi"
+    )
+    error_message = "The sidecar must not claim the ingress port and must carry its own resource limits."
+  }
+
+  assert {
+    condition = (
+      { for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name => e.value }["OPENAI_API_BASE"] == "https://example.invalid" &&
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name], "DATABASE_HOST") &&
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name], "REDIS_HOST") &&
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name if length(e.value_source) > 0], "LITELLM_MASTER_KEY") &&
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name if length(e.value_source) > 0], "DATABASE_PASSWORD") &&
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e.name if length(e.value_source) > 0], "OPENAI_API_KEY")
+    )
+    error_message = "The sidecar must receive the gateway's database, Redis, and Secret Manager env plus gateway_extra_env / gateway_extra_secrets."
+  }
+}
+
+run "coexists_with_the_metrics_sidecars" {
+  command = plan
+
+  variables {
+    collector_enabled    = true
+    gateway_metrics_port = 4001
+  }
+
+  assert {
+    condition     = [for c in google_cloud_run_v2_service.gateway[0].template[0].containers : c.name] == ["gateway", "metrics", "collector", "spend-collector"]
+    error_message = "The spend collector must keep its own container name next to the GMP metrics collector."
+  }
+
+  assert {
+    condition = (
+      { for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e.name => e.value }["PROMETHEUS_MULTIPROC_DIR"] == local.metrics_multiproc_dir &&
+      { for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e.name => e.value }["LITELLM_COLLECTOR_ENABLED"] == "true"
+    )
+    error_message = "The gateway container must keep both the metrics and the collector env when both sidecars are on."
+  }
+}
+
+run "sidecars_must_not_share_a_loopback_port" {
+  command = plan
+
+  variables {
+    collector_enabled    = true
+    collector_port       = 4001
+    gateway_metrics_port = 4001
+  }
+
+  expect_failures = [
+    google_cloud_run_v2_service.gateway,
+  ]
+}
+
+run "collector_cannot_take_the_metrics_sidecar_health_port" {
+  command = plan
+
+  variables {
+    collector_enabled = true
+    collector_port    = 13133
+  }
+
+  expect_failures = [
+    var.collector_port,
+  ]
+}
+
+run "proxy_config_is_mounted_into_the_sidecar_too" {
+  command = plan
+
+  variables {
+    collector_enabled = true
+    proxy_config      = { model_list = [] }
+  }
+
+  assert {
+    condition = alltrue([
+      for c in google_cloud_run_v2_service.gateway[0].template[0].containers : (
+        [for m in c.volume_mounts : m.name] == [local.proxy_config_volume] &&
+        contains([for e in c.env : e.name], "CONFIG_FILE_PATH")
+      )
+    ])
+    error_message = "Both containers must mount the proxy-config GCS volume and point CONFIG_FILE_PATH at it."
+  }
+}
diff --git a/terraform/litellm/gcp/tests/connection_pool.tftest.hcl b/terraform/litellm/gcp/tests/connection_pool.tftest.hcl
new file mode 100644
index 00000000000..999e4f0ff95
--- /dev/null
+++ b/terraform/litellm/gcp/tests/connection_pool.tftest.hcl
@@ -0,0 +1,174 @@
+# Plan-only coverage for the in-container PgBouncer knobs on the gateway
+# service. `mock_provider` keeps this offline: no GCP credentials, no API
+# calls, no resources. Run from terraform/litellm/gcp with `terraform test`.
+
+mock_provider "google" {
+  mock_resource "google_redis_instance" {
+    defaults = {
+      host = "10.0.0.4"
+      port = 6379
+      server_ca_certs = [{
+        cert = "-----BEGIN CERTIFICATE-----\nmock\n-----END CERTIFICATE-----"
+      }]
+    }
+  }
+}
+
+mock_provider "google-beta" {}
+mock_provider "random" {}
+
+variables {
+  project_id         = "test-project"
+  tenant             = "tenant"
+  env                = "test"
+  allow_plaintext_lb = true
+  image_registry     = "us-central1-docker.pkg.dev/test-project/litellm"
+}
+
+run "pool_off_by_default" {
+  command = plan
+
+  assert {
+    condition     = length(local.gateway_pool_env) == 0
+    error_message = "The gateway must get no LITELLM_PGBOUNCER_* env unless gateway_connection_pool_enabled is set."
+  }
+
+  assert {
+    condition = !anytrue([
+      for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : startswith(e.name, "LITELLM_PGBOUNCER_")
+    ])
+    error_message = "The gateway service must carry no LITELLM_PGBOUNCER_* env by default."
+  }
+}
+
+run "pool_enabled_renders_the_three_vars_with_configured_sizes" {
+  command = plan
+
+  variables {
+    gateway_num_workers             = 4
+    gateway_connection_pool_enabled = true
+    gateway_pool_max_db_connections = 8
+    gateway_pool_max_client_conn    = 250
+  }
+
+  assert {
+    condition = alltrue([
+      length(local.gateway_pool_env) == 3,
+      local.gateway_pool_env[0].name == "LITELLM_PGBOUNCER_ENABLED" && local.gateway_pool_env[0].value == "true",
+      local.gateway_pool_env[1].name == "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS" && local.gateway_pool_env[1].value == "8",
+      local.gateway_pool_env[2].name == "LITELLM_PGBOUNCER_MAX_CLIENT_CONN" && local.gateway_pool_env[2].value == "250",
+    ])
+    error_message = "The pool env must carry the enabled flag and the configured sizes as strings."
+  }
+
+  assert {
+    condition = alltrue([
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e.name], "LITELLM_PGBOUNCER_ENABLED"),
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e.name], "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS"),
+      contains([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e.name], "LITELLM_PGBOUNCER_MAX_CLIENT_CONN"),
+    ])
+    error_message = "The gateway service must receive all three LITELLM_PGBOUNCER_* env vars."
+  }
+
+  assert {
+    condition = !anytrue(concat(
+      [for e in google_cloud_run_v2_service.backend[0].template[0].containers[0].env : startswith(e.name, "LITELLM_PGBOUNCER_")],
+      [for e in google_cloud_run_v2_job.migrations[0].template[0].template[0].containers[0].env : startswith(e.name, "LITELLM_PGBOUNCER_")],
+    ))
+    error_message = "The backend service and the migrations job must keep their direct database connection."
+  }
+}
+
+run "collector_sidecar_gets_the_same_pool_env_as_the_gateway" {
+  command = plan
+
+  variables {
+    collector_enabled               = true
+    gateway_connection_pool_enabled = true
+    gateway_pool_max_db_connections = 8
+    gateway_pool_max_client_conn    = 250
+  }
+
+  assert {
+    condition = alltrue([
+      for c in google_cloud_run_v2_service.gateway[0].template[0].containers : (
+        { for e in c.env : e.name => e.value }["LITELLM_PGBOUNCER_ENABLED"] == "true" &&
+        { for e in c.env : e.name => e.value }["LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS"] == "8" &&
+        { for e in c.env : e.name => e.value }["LITELLM_PGBOUNCER_MAX_CLIENT_CONN"] == "250"
+      ) if c.name == "spend-collector"
+    ]) && length([for c in google_cloud_run_v2_service.gateway[0].template[0].containers : c.name if c.name == "spend-collector"]) == 1
+    error_message = "The spend-collector sidecar must carry the same three LITELLM_PGBOUNCER_* vars as the gateway so its Prisma connects to the instance-local pool."
+  }
+}
+
+run "collector_sidecar_gets_no_pool_env_when_the_pool_is_off" {
+  command = plan
+
+  variables {
+    collector_enabled = true
+  }
+
+  assert {
+    condition = !anytrue(flatten([
+      for c in google_cloud_run_v2_service.gateway[0].template[0].containers : [
+        for e in c.env : startswith(e.name, "LITELLM_PGBOUNCER_")
+      ] if c.name == "spend-collector"
+    ])) && length([for c in google_cloud_run_v2_service.gateway[0].template[0].containers : c.name if c.name == "spend-collector"]) == 1
+    error_message = "The spend-collector sidecar must get no LITELLM_PGBOUNCER_* env unless gateway_connection_pool_enabled is set."
+  }
+}
+
+run "pool_enabled_uses_the_module_default_sizes" {
+  command = plan
+
+  variables {
+    gateway_connection_pool_enabled = true
+  }
+
+  assert {
+    condition = alltrue([
+      length(local.gateway_pool_env) == 3,
+      local.gateway_pool_env[1].name == "LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS" && local.gateway_pool_env[1].value == "20",
+      local.gateway_pool_env[2].name == "LITELLM_PGBOUNCER_MAX_CLIENT_CONN" && local.gateway_pool_env[2].value == "1000",
+    ])
+    error_message = "The pool env must fall back to the module defaults of 20 upstream and 1000 client connections."
+  }
+}
+
+run "gateway_starts_through_the_pool_aware_launcher" {
+  command = plan
+
+  variables {
+    gateway_num_workers = 4
+  }
+
+  assert {
+    condition = alltrue([
+      strcontains(local.gateway_launch_cmd, "exec python -m gateway.launch --host 0.0.0.0 --port 4000 --workers 4"),
+      strcontains(local.gateway_launch_cmd, "exec ddtrace-run python -m gateway.launch --host 0.0.0.0 --port 4000 --workers 4"),
+      !strcontains(local.gateway_launch_cmd, "uvicorn gateway.main:app"),
+      endswith(google_cloud_run_v2_service.gateway[0].template[0].containers[0].args[0], local.gateway_launch_cmd),
+    ])
+    error_message = "The gateway must start through gateway.launch (with and without ddtrace) so the pooler starts once before uvicorn forks the workers."
+  }
+
+  assert {
+    condition     = strcontains(local.backend_launch_cmd, "uvicorn backend.main:app")
+    error_message = "The backend has no workers to share a pooler and keeps starting uvicorn directly."
+  }
+}
+
+run "pool_sizes_below_one_fail_at_plan" {
+  command = plan
+
+  variables {
+    gateway_connection_pool_enabled = true
+    gateway_pool_max_db_connections = 0
+    gateway_pool_max_client_conn    = 0
+  }
+
+  expect_failures = [
+    var.gateway_pool_max_db_connections,
+    var.gateway_pool_max_client_conn,
+  ]
+}
diff --git a/terraform/litellm/gcp/tests/metrics_sidecar.tftest.hcl b/terraform/litellm/gcp/tests/metrics_sidecar.tftest.hcl
new file mode 100644
index 00000000000..7de62065d23
--- /dev/null
+++ b/terraform/litellm/gcp/tests/metrics_sidecar.tftest.hcl
@@ -0,0 +1,200 @@
+mock_provider "google" {
+  mock_resource "google_redis_instance" {
+    defaults = {
+      host = "10.0.0.4"
+      port = 6379
+      server_ca_certs = [{
+        cert = "-----BEGIN CERTIFICATE-----\nmock\n-----END CERTIFICATE-----"
+      }]
+    }
+  }
+}
+
+mock_provider "google-beta" {}
+mock_provider "random" {}
+
+variables {
+  project_id         = "test-project"
+  tenant             = "tenant"
+  env                = "test"
+  allow_plaintext_lb = true
+  image_registry     = "us-central1-docker.pkg.dev/test-project/litellm"
+}
+
+run "metrics_sidecar_off_by_default" {
+  command = plan
+
+  assert {
+    condition     = length(google_cloud_run_v2_service.gateway[0].template[0].containers) == 1
+    error_message = "The gateway service must run only the gateway container when gateway_metrics_port is null."
+  }
+
+  assert {
+    condition     = length([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e if e.name == "PROMETHEUS_MULTIPROC_DIR"]) == 0
+    error_message = "PROMETHEUS_MULTIPROC_DIR must not be set when the metrics sidecar is off."
+  }
+
+  assert {
+    condition     = length(google_cloud_run_v2_service.gateway[0].template[0].volumes) == 0
+    error_message = "No shared multiproc or collector config volume must exist when the metrics sidecar is off."
+  }
+
+  assert {
+    condition = alltrue([
+      length(google_secret_manager_secret.metrics_run_monitoring) == 0,
+      length(google_secret_manager_secret_version.metrics_run_monitoring) == 0,
+      length(google_secret_manager_secret_iam_member.metrics_run_monitoring) == 0,
+      length(google_project_iam_member.runtime_metric_writer) == 0,
+      length(google_project_iam_member.runtime_log_writer) == 0,
+    ])
+    error_message = "No RunMonitoring secret or monitoring IAM must be created when the metrics sidecar is off."
+  }
+}
+
+run "metrics_sidecar_enabled" {
+  command = plan
+
+  variables {
+    gateway_metrics_port = 4001
+  }
+
+  assert {
+    condition     = join(",", [for c in google_cloud_run_v2_service.gateway[0].template[0].containers : c.name]) == "gateway,metrics,collector"
+    error_message = "gateway_metrics_port must add the metrics and collector sidecars after the gateway container."
+  }
+
+  assert {
+    condition = alltrue([
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].image == local.gateway_image,
+      join(" ", google_cloud_run_v2_service.gateway[0].template[0].containers[1].command) == "python -m litellm.proxy.prometheus_metrics_server",
+      join(" ", google_cloud_run_v2_service.gateway[0].template[0].containers[1].args) == "--port 4001",
+    ])
+    error_message = "The metrics sidecar must run the gateway image's prometheus_metrics_server on the configured port."
+  }
+
+  assert {
+    condition = alltrue([
+      length([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[0].env : e if e.name == "PROMETHEUS_MULTIPROC_DIR" && e.value == "/tmp/litellm_prometheus_multiproc"]) == 1,
+      length([for e in google_cloud_run_v2_service.gateway[0].template[0].containers[1].env : e if e.name == "PROMETHEUS_MULTIPROC_DIR" && e.value == "/tmp/litellm_prometheus_multiproc"]) == 1,
+    ])
+    error_message = "Gateway and metrics containers must share PROMETHEUS_MULTIPROC_DIR."
+  }
+
+  assert {
+    condition = alltrue([
+      length([for m in google_cloud_run_v2_service.gateway[0].template[0].containers[0].volume_mounts : m if m.name == "prometheus-multiproc" && m.mount_path == "/tmp/litellm_prometheus_multiproc"]) == 1,
+      length([for m in google_cloud_run_v2_service.gateway[0].template[0].containers[1].volume_mounts : m if m.name == "prometheus-multiproc" && m.mount_path == "/tmp/litellm_prometheus_multiproc"]) == 1,
+      length([for v in google_cloud_run_v2_service.gateway[0].template[0].volumes : v if v.name == "prometheus-multiproc" && length(v.empty_dir) == 1 && v.empty_dir[0].medium == "MEMORY"]) == 1,
+    ])
+    error_message = "Gateway and metrics containers must mount the same in-memory empty_dir at the multiproc dir."
+  }
+
+  assert {
+    condition = alltrue([
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].startup_probe[0].http_get[0].path == "/health",
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].startup_probe[0].http_get[0].port == 4001,
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].liveness_probe[0].http_get[0].path == "/health",
+      google_cloud_run_v2_service.gateway[0].template[0].containers[1].liveness_probe[0].http_get[0].port == 4001,
+    ])
+    error_message = "The metrics sidecar must be probed on /health at the configured port."
+  }
+
+  assert {
+    condition     = length(google_cloud_run_v2_service.gateway[0].template[0].containers[1].ports) == 0 && length(google_cloud_run_v2_service.gateway[0].template[0].containers[2].ports) == 0
+    error_message = "Only the gateway container may declare a port; Cloud Run routes ingress to exactly one container."
+  }
+
+  assert {
+    condition = alltrue([
+      google_cloud_run_v2_service.gateway[0].template[0].containers[0].ports[0].container_port == 4000,
+      google_cloud_run_v2_service.gateway[0].template[0].containers[0].startup_probe[0].http_get[0].port == 4000,
+      google_cloud_run_v2_service.gateway[0].template[0].containers[0].liveness_probe[0].http_get[0].port == 4000,
+      google_compute_region_network_endpoint_group.gateway[0].cloud_run[0].service == "${local.name}-gateway",
+    ])
+    error_message = "The gateway must stay on port 4000 and remain the load balancer's Cloud Run target."
+  }
+
+  assert {
+    condition = alltrue([
+      google_cloud_run_v2_service.gateway[0].template[0].containers[2].image == var.gateway_metrics_collector_image,
+      join(",", google_cloud_run_v2_service.gateway[0].template[0].containers[2].depends_on) == "metrics",
+      length([for m in google_cloud_run_v2_service.gateway[0].template[0].containers[2].volume_mounts : m if m.name == "gmp-config" && m.mount_path == "/etc/rungmp"]) == 1,
+      google_cloud_run_v2_service.gateway[0].template[0].containers[2].liveness_probe[0].http_get[0].port == 13133,
+    ])
+    error_message = "The collector sidecar must start after the metrics server and read its RunMonitoring config from /etc/rungmp."
+  }
+
+  assert {
+    condition = alltrue([
+      length([for v in google_cloud_run_v2_service.gateway[0].template[0].volumes : v if v.name == "gmp-config" && length(v.secret) == 1 && v.secret[0].items[0].path == "config.yaml"]) == 1,
+      google_secret_manager_secret.metrics_run_monitoring[0].secret_id == "${local.name}-gateway-run-monitoring",
+      google_secret_manager_secret_iam_member.metrics_run_monitoring[0].role == "roles/secretmanager.secretAccessor",
+    ])
+    error_message = "The RunMonitoring config must be mounted from a Secret Manager secret readable by the runtime SA."
+  }
+
+  assert {
+    condition = alltrue([
+      yamldecode(google_secret_manager_secret_version.metrics_run_monitoring[0].secret_data).kind == "RunMonitoring",
+      yamldecode(google_secret_manager_secret_version.metrics_run_monitoring[0].secret_data).spec.endpoints[0].port == 4001,
+      yamldecode(google_secret_manager_secret_version.metrics_run_monitoring[0].secret_data).spec.endpoints[0].path == "/metrics",
+    ])
+    error_message = "The RunMonitoring config must scrape /metrics on the configured metrics port."
+  }
+
+  assert {
+    condition = alltrue([
+      google_project_iam_member.runtime_metric_writer[0].role == "roles/monitoring.metricWriter",
+      google_project_iam_member.runtime_log_writer[0].role == "roles/logging.logWriter",
+      google_project_iam_member.runtime_metric_writer[0].project == "test-project",
+    ])
+    error_message = "The runtime SA must be able to write metrics and logs for the collector sidecar."
+  }
+}
+
+run "metrics_sidecar_ignored_in_deps_only" {
+  command = plan
+
+  variables {
+    create_runtime       = false
+    gateway_metrics_port = 4001
+  }
+
+  assert {
+    condition = alltrue([
+      length(google_secret_manager_secret.metrics_run_monitoring) == 0,
+      length(google_project_iam_member.runtime_metric_writer) == 0,
+    ])
+    error_message = "Dependencies-only mode must not create metrics sidecar resources."
+  }
+}
+
+run "metrics_port_rejects_gateway_port" {
+  command = plan
+
+  variables {
+    gateway_metrics_port = 4000
+  }
+
+  expect_failures = [var.gateway_metrics_port]
+}
+
+run "metrics_port_rejects_collector_health_port" {
+  command = plan
+
+  variables {
+    gateway_metrics_port = 13133
+  }
+
+  expect_failures = [var.gateway_metrics_port]
+}
+
+run "metrics_port_rejects_fractional_port" {
+  command = plan
+
+  variables {
+    gateway_metrics_port = 4000.5
+  }
+
+  expect_failures = [var.gateway_metrics_port]
+}
diff --git a/terraform/litellm/gcp/variables.tf b/terraform/litellm/gcp/variables.tf
index 9c68ed3db76..412f919ab89 100644
--- a/terraform/litellm/gcp/variables.tf
+++ b/terraform/litellm/gcp/variables.tf
@@ -206,6 +206,45 @@ variable "gateway_num_workers" {
   }
 }
 
+variable "gateway_connection_pool_enabled" {
+  description = <<-EOT
+    Run an in-container PgBouncer (transaction mode, loopback) in each gateway
+    instance, shared by every uvicorn worker. Without it each of the
+    `gateway_num_workers` workers opens its own Prisma pool straight to
+    Cloud SQL, so an instance's footprint against the database connection
+    ceiling is workers x connection_limit and grows with every instance. Sets
+    LITELLM_PGBOUNCER_ENABLED / LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS /
+    LITELLM_PGBOUNCER_MAX_CLIENT_CONN on the gateway container only. The
+    module's Cloud SQL authenticates with the static password in Secret
+    Manager, which is what the pooler needs. Mirrors the AWS stack's
+    gateway_connection_pool_enabled.
+  EOT
+  type        = bool
+  default     = false
+}
+
+variable "gateway_pool_max_db_connections" {
+  description = "Upstream Cloud SQL connections one gateway instance may hold when gateway_connection_pool_enabled is set, regardless of gateway_num_workers. 20 suits 4 workers."
+  type        = number
+  default     = 20
+
+  validation {
+    condition     = var.gateway_pool_max_db_connections >= 1
+    error_message = "gateway_pool_max_db_connections must be >= 1."
+  }
+}
+
+variable "gateway_pool_max_client_conn" {
+  description = "Client connections the in-container PgBouncer accepts from the gateway workers when gateway_connection_pool_enabled is set."
+  type        = number
+  default     = 1000
+
+  validation {
+    condition     = var.gateway_pool_max_client_conn >= 1
+    error_message = "gateway_pool_max_client_conn must be >= 1."
+  }
+}
+
 # Cloud Run autoscales out of the box (request-rate driven). The min/max
 # bounds mirror the HPA replica bounds in helm/litellm/values.yaml so each
 # stack scales over the same range. Cloud Run has no direct CPU-utilization
@@ -517,6 +556,44 @@ variable "otel_capture_message_content" {
   }
 }
 
+# ---------- Prometheus metrics sidecar ----------
+
+variable "gateway_metrics_port" {
+  description = <<-EOT
+    Serve Prometheus /metrics from a `metrics` sidecar container in the
+    gateway Cloud Run service on this port (a whole number 1-65535, not 4000
+    or 13133), so the collector's scrape never runs on an inference worker.
+    The sidecar runs the gateway image with
+    `python -m litellm.proxy.prometheus_metrics_server` and aggregates the
+    workers' PROMETHEUS_MULTIPROC_DIR samples over an in-memory volume shared
+    with the gateway container. Cloud Run only routes ingress to the gateway
+    container, so the sidecar port is reachable on localhost inside the
+    instance only; a Managed Service for Prometheus collector sidecar
+    (gateway_metrics_collector_image) scrapes it and writes the series to
+    Cloud Monitoring. The load balancer keeps serving the authenticated
+    /metrics on the gateway port as before. Null (the default) leaves /metrics
+    on the gateway port only. Needs gateway_image v1.101.0 or newer.
+  EOT
+  type        = number
+  default     = null
+
+  validation {
+    condition     = var.gateway_metrics_port == null || (var.gateway_metrics_port >= 1 && var.gateway_metrics_port <= 65535 && floor(var.gateway_metrics_port) == var.gateway_metrics_port && !contains([4000, 13133], var.gateway_metrics_port))
+    error_message = "gateway_metrics_port must be a whole number between 1 and 65535 and must not be 4000 (the gateway port) or 13133 (the collector health port)."
+  }
+}
+
+variable "gateway_metrics_collector_image" {
+  description = <<-EOT
+    Managed Service for Prometheus sidecar image that scrapes
+    localhost:<gateway_metrics_port>/metrics and writes to Cloud Monitoring.
+    Override only to pin a different release or pull through your own
+    Artifact Registry. Ignored when gateway_metrics_port is null.
+  EOT
+  type        = string
+  default     = "us-docker.pkg.dev/cloud-ops-agents-artifacts/cloud-run-gmp-sidecar/cloud-run-gmp-sidecar:1.9.2"
+}
+
 # ---------- Enterprise billing metrics ----------
 #
 # License-gated request metering. Opt-in and gated entirely on
@@ -579,3 +656,73 @@ variable "billing_metrics_ca_cert_pem" {
   default     = ""
   sensitive   = true
 }
+
+# ---------- Collector sidecar ----------
+#
+# Opt-in offload of spend tracking from the gateway's uvicorn workers to a
+# `python -m litellm.proxy.collector` sidecar container in the same Cloud Run
+# instance (helm's `gateway.collector`, mirrors the AWS stack). Containers
+# in one instance share localhost, so the sidecar listens on loopback TCP.
+# Disabled (the default) adds nothing to the service.
+
+variable "collector_enabled" {
+  description = "Run the collector sidecar next to the gateway container and have the gateway ship spend events to it (sets LITELLM_COLLECTOR_ENABLED=true on both). The sidecar shares the instance's request-based CPU allocation, so pair it with a non-zero gateway_min_instances if spend must keep flowing between requests."
+  type        = bool
+  default     = false
+}
+
+variable "collector_port" {
+  description = "Loopback TCP port the sidecar listens on (LITELLM_COLLECTOR_ADDRESS=tcp://127.0.0.1:<port>)."
+  type        = number
+  default     = 4010
+
+  validation {
+    condition     = var.collector_port >= 1024 && var.collector_port <= 65535 && !contains([4000, 13133], var.collector_port)
+    error_message = "collector_port must be in 1024-65535 and not 4000 (the gateway port) or 13133 (the metrics sidecar health port)."
+  }
+}
+
+variable "collector_cpu" {
+  description = "Cloud Run CPU limit for the sidecar container, on top of gateway_cpu. Matches helm's collector.resources.limits.cpu."
+  type        = string
+  default     = "1000m"
+}
+
+variable "collector_memory" {
+  description = "Cloud Run memory limit for the sidecar container, on top of gateway_memory. Matches helm's collector.resources.limits.memory."
+  type        = string
+  default     = "2Gi"
+}
+
+variable "collector_buffer_size" {
+  description = "Per-worker in-memory queue of spend events waiting to be shipped to the sidecar (LITELLM_COLLECTOR_BUFFER_SIZE)."
+  type        = number
+  default     = 1000
+
+  validation {
+    condition     = var.collector_buffer_size >= 1
+    error_message = "collector_buffer_size must be >= 1."
+  }
+}
+
+variable "collector_on_unavailable" {
+  description = "What the gateway does with spend events when the sidecar is unreachable or the buffer is full (LITELLM_COLLECTOR_ON_UNAVAILABLE): `fallback` runs the pipeline in-process, `drop` discards them."
+  type        = string
+  default     = "fallback"
+
+  validation {
+    condition     = contains(["fallback", "drop"], var.collector_on_unavailable)
+    error_message = "collector_on_unavailable must be one of: fallback, drop."
+  }
+}
+
+variable "collector_drain_timeout_seconds" {
+  description = "Seconds a gateway worker waits on shutdown for its buffered spend events to reach the sidecar (LITELLM_COLLECTOR_DRAIN_TIMEOUT_SECONDS)."
+  type        = number
+  default     = 10
+
+  validation {
+    condition     = var.collector_drain_timeout_seconds > 0
+    error_message = "collector_drain_timeout_seconds must be > 0."
+  }
+}
diff --git a/terraform/provider/CHANGELOG.md b/terraform/provider/CHANGELOG.md
index 842bfb4bdb1..e5e0a164a83 100644
--- a/terraform/provider/CHANGELOG.md
+++ b/terraform/provider/CHANGELOG.md
@@ -16,6 +16,7 @@ longer signal it.
 
 ### Added
 
+- **team**: Optional `team_id` argument on `litellm_team`, so teams can be created with a stable, human-readable ID instead of a provider-generated UUID; changing it forces replacement
 - **jwt_key_mapping**: New `litellm_jwt_key_mapping` resource for the proxy's JWT to virtual key mappings, so JWT clients identified by a claim (`client_id`, `azp`, `sub`) map to virtual keys and inherit their models, budgets and rate limits. Supports `description` and `is_active`, rotating the mapped key in place, and forces replacement when the claim name or value changes
 - **team**: `soft_budget`, `tags`, and `soft_budget_alerting_emails` attributes on `litellm_team`, matching what `/team/new` and `/team/update` already accept; `soft_budget_alerting_emails` is sent under `metadata`, where the proxy reads it
 - **user**: New `litellm_user` resource and `litellm_user` / `litellm_users` data sources for managing internal users
@@ -38,12 +39,14 @@ longer signal it.
 
 - **team**: Read now decodes the `team_info` envelope `/team/info` actually returns, so team attributes refresh from the proxy instead of always falling back to the prior state
 - **key**: Read now unwraps the `info` envelope `/key/info` actually returns; previously reads mapped nothing back into state, so drift on a key was never detected
+- **key**: Read now picks up `model_rpm_limit`, `model_tpm_limit`, `guardrails`, `tags`, `enforced_params`, `allowed_passthrough_routes`, `rpm_limit_type`, `tpm_limit_type` and `prompts` from `info.metadata`, where the proxy actually stores them; previously they stayed empty in state, so a matching config showed a permanent phantom diff on them and out-of-band changes to them were never detected
 - **key**: Updates no longer send an empty `budget_duration`, which the proxy rejects with a 400; any update to a key without a configured `budget_duration` previously failed outright
 - **key**: A config-supplied `key` value (write-only) is now forwarded to `/key/generate`; previously it was silently dropped and the proxy generated a random key instead
 - **security**: The `litellm_key` data source and `litellm_key_block` resource normalize raw `sk-` keys to their SHA-256 token hash before building request URLs and resource IDs, so plaintext keys no longer land in reverse-proxy access logs, Terraform plan output, or state IDs
 
 ### Changed
 
+- **key** (breaking): `model_max_budget` on `litellm_key` is now a JSON string of per-model budget objects (`jsonencode({"gpt-4o-mini" = {budget_limit = 50, time_period = "30d"}})`), matching `litellm_user`, `litellm_budget` and `litellm_tag`. The old `map(number)` form sent bare numbers to `/key/generate`, which the proxy rejects with a 500 (`'int' object is not iterable`), so every key with a non-empty `model_max_budget` failed to apply. Existing state upgrades automatically (schema version 1) and the attribute is refilled from the proxy on the next read; configurations still using the map form must be rewritten
 - **Versioning**: the provider is now published at the LiteLLM version, from the same commit as the proxy, on every LiteLLM release (dev, rc, stable). The `0.x` line ends at `0.4.0`; a `~> 0.4` constraint will not receive further releases, so re-pin to the LiteLLM version your proxy runs (for example `~> 1.99.0`). Existing `0.x` versions remain in the registry and keep verifying
 
 ## [0.4.0] - 2026-08-06
diff --git a/terraform/provider/README.md b/terraform/provider/README.md
index 0a6d15c7844..b392fd6279d 100644
--- a/terraform/provider/README.md
+++ b/terraform/provider/README.md
@@ -103,9 +103,12 @@ resource "litellm_key" "example_key" {
   permissions          = {
     can_create_keys = "true"
   }
-  model_max_budget     = {
-    "gpt-4" = 50.0
-  }
+  model_max_budget     = jsonencode({
+    "gpt-4" = {
+      budget_limit = 50.0
+      time_period  = "30d"
+    }
+  })
   model_rpm_limit      = {
     "claude-3.5-sonnet" = 30
   }
diff --git a/terraform/provider/docs/resources/key.md b/terraform/provider/docs/resources/key.md
index 5094b77cbec..0ef0688830f 100644
--- a/terraform/provider/docs/resources/key.md
+++ b/terraform/provider/docs/resources/key.md
@@ -30,9 +30,12 @@ resource "litellm_key" "example" {
   permissions          = {
     "can_create_keys" = "true"
   }
-  model_max_budget     = {
-    "gpt-4" = 50.0
-  }
+  model_max_budget     = jsonencode({
+    "gpt-4" = {
+      budget_limit = 50.0
+      time_period  = "30d"
+    }
+  })
   model_rpm_limit      = {
     "gpt-3.5-turbo" = 30
   }
@@ -73,7 +76,7 @@ The following arguments are supported:
 
 * `key_alias` - (Optional) Alias for this key. This provides a human-readable identifier for the key.
 
-* `duration` - (Optional) Duration for which this key is valid. This sets an expiration time for the key.
+* `duration` - (Optional) How long the key stays valid, e.g. "30d" or "12h". The proxy stores this as an absolute `expires` timestamp. Changing the value resets the expiry to the time of the update plus the new duration; removing it from the configuration leaves the current expiry in place.
 
 * `aliases` - (Optional) Map of model aliases. This allows you to create custom names for models when using this key.
 
@@ -81,7 +84,7 @@ The following arguments are supported:
 
 * `permissions` - (Optional) Permissions associated with this key. This defines what actions are allowed with this key.
 
-* `model_max_budget` - (Optional) Maximum budget per model. This allows setting different budget limits for each model.
+* `model_max_budget` - (Optional) JSON string of per-model budget config, e.g. `jsonencode({"gpt-4" = {budget_limit = 50.0, time_period = "30d"}})`. Each model maps to an object with `budget_limit` (or `max_budget`), `time_period` (or `budget_duration`), `tpm_limit` and `rpm_limit`.
 
 * `model_rpm_limit` - (Optional) Requests per minute limit per model. This allows setting different RPM limits for each model.
 
diff --git a/terraform/provider/docs/resources/team.md b/terraform/provider/docs/resources/team.md
index 821d8c1dee3..19575907269 100644
--- a/terraform/provider/docs/resources/team.md
+++ b/terraform/provider/docs/resources/team.md
@@ -14,6 +14,16 @@ resource "litellm_team" "engineering" {
 }
 ```
 
+### Team with a Custom ID
+
+```hcl
+resource "litellm_team" "platform" {
+  team_id    = "platform-team"
+  team_alias = "platform"
+  models     = ["gpt-4-proxy"]
+}
+```
+
 ### Team with Comprehensive Configuration
 
 ```hcl
@@ -92,6 +102,8 @@ resource "litellm_team" "model_dependent_team" {
 
 The following arguments are supported:
 
+* `team_id` - (Optional) A stable, human-readable ID for the team (for example `platform-team`). If omitted, the provider generates a random UUID. Changing this forces a new team to be created.
+
 * `team_alias` - (Required) A human-readable identifier for the team.
 
 * `organization_id` - (Optional) The ID of the organization this team belongs to.
@@ -152,7 +164,7 @@ The following arguments are supported:
 
 In addition to the arguments above, the following attributes are exported:
 
-* `id` - The unique identifier for the team.
+* `id` - The unique identifier for the team, equal to `team_id`.
 
 ## Import
 
@@ -162,7 +174,7 @@ Teams can be imported using the team ID:
 terraform import litellm_team.engineering <team-id>
 ```
 
-Note: The team ID is generated when the team is created and is different from the `team_alias`.
+Note: Unless `team_id` is set, the team ID is generated when the team is created and is different from the `team_alias`.
 
 ## Note on Team Members
 
diff --git a/terraform/provider/litellm/client.go b/terraform/provider/litellm/client.go
index 0f825d85d31..e68b8a3a80b 100644
--- a/terraform/provider/litellm/client.go
+++ b/terraform/provider/litellm/client.go
@@ -4,6 +4,7 @@ import (
 	"bytes"
 	"crypto/tls"
 	"encoding/json"
+	"errors"
 	"fmt"
 	"io"
 	"log"
@@ -19,6 +20,20 @@ type Client struct {
 	InsecureSkipVerify bool
 }
 
+type apiError struct {
+	StatusCode int
+	Body       string
+}
+
+func (e *apiError) Error() string {
+	return fmt.Sprintf("API request failed with status code %d: %s", e.StatusCode, e.Body)
+}
+
+func isNotFound(err error) bool {
+	var apiErr *apiError
+	return errors.As(err, &apiErr) && apiErr.StatusCode == http.StatusNotFound
+}
+
 func NewClient(apiBase, apiKey string, insecureSkipVerify bool) *Client {
 	tr := &http.Transport{
 		TLSClientConfig: &tls.Config{InsecureSkipVerify: insecureSkipVerify},
@@ -57,6 +72,9 @@ func (c *Client) CreateKey(key *Key) (*Key, error) {
 
 func (c *Client) GetKey(keyID string) (*Key, error) {
 	resp, err := c.sendRequest("GET", fmt.Sprintf("/key/info?key=%s", keyID), nil)
+	if isNotFound(err) {
+		return nil, nil
+	}
 	if err != nil {
 		return nil, err
 	}
@@ -69,32 +87,71 @@ func (c *Client) GetKey(keyID string) (*Key, error) {
 				info["key"] = k
 			}
 		}
+		hoistKeyFieldsStoredInMetadata(info)
 		return c.parseKeyResponse(info)
 	}
 
 	return c.parseKeyResponse(resp)
 }
 
+var keyFieldsStoredInMetadata = []string{
+	"model_rpm_limit",
+	"model_tpm_limit",
+	"guardrails",
+	"tags",
+	"enforced_params",
+	"allowed_passthrough_routes",
+	"rpm_limit_type",
+	"tpm_limit_type",
+	"prompts",
+}
+
+func hoistKeyFieldsStoredInMetadata(info map[string]interface{}) {
+	metadata, ok := info["metadata"].(map[string]interface{})
+	if !ok {
+		return
+	}
+	for _, field := range keyFieldsStoredInMetadata {
+		if existing, present := info[field]; present && existing != nil {
+			continue
+		}
+		if v, present := metadata[field]; present {
+			info[field] = v
+		}
+	}
+}
+
 func (c *Client) UpdateKey(key *Key) (*Key, error) {
 	// Create a new map with only the fields that can be updated
 	updateData := map[string]interface{}{
 		"key":              key.Key,
 		"team_id":          key.TeamID,
-		"metadata":         key.Metadata,
 		"key_alias":        key.KeyAlias,
 		"aliases":          key.Aliases,
 		"permissions":      key.Permissions,
 		"model_max_budget": key.ModelMaxBudget,
-		"model_rpm_limit":  key.ModelRPMLimit,
-		"model_tpm_limit":  key.ModelTPMLimit,
 		"blocked":          key.Blocked,
 	}
 
+	// The proxy keeps the stored metadata only when the field is absent, so nil means omit.
+	if key.Metadata != nil {
+		updateData["metadata"] = key.Metadata
+	}
+	if key.ModelRPMLimit != nil {
+		updateData["model_rpm_limit"] = key.ModelRPMLimit
+	}
+	if key.ModelTPMLimit != nil {
+		updateData["model_tpm_limit"] = key.ModelTPMLimit
+	}
+
 	// The proxy rejects an empty-string budget_duration with a 400, so only
 	// send it when set.
 	if key.BudgetDuration != "" {
 		updateData["budget_duration"] = key.BudgetDuration
 	}
+	if key.Duration != "" {
+		updateData["duration"] = key.Duration
+	}
 
 	// Only add pointer fields if they are explicitly set
 	if key.MaxBudget != nil {
@@ -366,7 +423,7 @@ func (c *Client) sendRequest(method, path string, body interface{}) (map[string]
 	log.Printf("Response body: %s", c.redactSensitiveData(string(bodyBytes)))
 
 	if resp.StatusCode != http.StatusOK {
-		return nil, fmt.Errorf("API request failed with status code %d: %s", resp.StatusCode, string(bodyBytes))
+		return nil, &apiError{StatusCode: resp.StatusCode, Body: string(bodyBytes)}
 	}
 
 	var result map[string]interface{}
diff --git a/terraform/provider/litellm/resource_key.go b/terraform/provider/litellm/resource_key.go
index 0d8674f2d4c..018d01f75a8 100644
--- a/terraform/provider/litellm/resource_key.go
+++ b/terraform/provider/litellm/resource_key.go
@@ -2,7 +2,9 @@ package litellm
 
 import (
 	"context"
+	"encoding/json"
 	"fmt"
+	"log"
 
 	"github.com/hashicorp/go-cty/cty"
 	"github.com/hashicorp/terraform-plugin-sdk/v2/diag"
@@ -10,7 +12,7 @@ import (
 )
 
 func resourceKey() *schema.Resource {
-	return &schema.Resource{
+	r := &schema.Resource{
 		CreateContext: resourceKeyCreate,
 		ReadContext:   resourceKeyRead,
 		UpdateContext: resourceKeyUpdate,
@@ -18,6 +20,7 @@ func resourceKey() *schema.Resource {
 		Importer: &schema.ResourceImporter{
 			StateContext: schema.ImportStatePassthroughContext,
 		},
+		SchemaVersion: 1,
 		Schema: map[string]*schema.Schema{
 			"key": {
 				Type:      schema.TypeString,
@@ -86,8 +89,9 @@ func resourceKey() *schema.Resource {
 				Optional: true,
 			},
 			"duration": {
-				Type:     schema.TypeString,
-				Optional: true,
+				Type:        schema.TypeString,
+				Optional:    true,
+				Description: "How long the key stays valid, e.g. \"30d\" or \"12h\". Changing it resets the expiry to the time of the update plus the new duration; removing it leaves the current expiry in place",
 			},
 			"aliases": {
 				Type:     schema.TypeMap,
@@ -105,9 +109,11 @@ func resourceKey() *schema.Resource {
 				Elem:     &schema.Schema{Type: schema.TypeString},
 			},
 			"model_max_budget": {
-				Type:     schema.TypeMap,
-				Optional: true,
-				Elem:     &schema.Schema{Type: schema.TypeFloat, Computed: true},
+				Type:             schema.TypeString,
+				Optional:         true,
+				ValidateFunc:     validateKeyModelMaxBudget,
+				DiffSuppressFunc: budgetSuppressEquivalentJSON,
+				Description:      "JSON string of per-model budget config (e.g. '{\"gpt-4o-mini\": {\"budget_limit\": 50, \"time_period\": \"30d\"}}')",
 			},
 			"model_rpm_limit": {
 				Type:     schema.TypeMap,
@@ -182,6 +188,79 @@ func resourceKey() *schema.Resource {
 			},
 		},
 	}
+	r.StateUpgraders = []schema.StateUpgrader{{
+		Version: 0,
+		Type:    resourceKeyV0Type(r.Schema),
+		Upgrade: resourceKeyStateUpgradeV0,
+	}}
+	return r
+}
+
+// Schema version 0 typed model_max_budget as map(number), which the proxy
+// rejects; version 1 stores the per-model BudgetConfig objects as a JSON string.
+func resourceKeyV0Type(current map[string]*schema.Schema) cty.Type {
+	v0 := make(map[string]*schema.Schema, len(current))
+	for k, v := range current {
+		v0[k] = v
+	}
+	v0["model_max_budget"] = &schema.Schema{
+		Type:     schema.TypeMap,
+		Optional: true,
+		Elem:     &schema.Schema{Type: schema.TypeFloat},
+	}
+	return (&schema.Resource{Schema: v0}).CoreConfigSchema().ImpliedType()
+}
+
+func resourceKeyStateUpgradeV0(_ context.Context, rawState map[string]interface{}, _ interface{}) (map[string]interface{}, error) {
+	delete(rawState, "model_max_budget")
+	return rawState, nil
+}
+
+var keyModelBudgetFields = map[string]bool{
+	"budget_limit":    true,
+	"max_budget":      true,
+	"time_period":     true,
+	"budget_duration": true,
+	"tpm_limit":       true,
+	"rpm_limit":       true,
+}
+
+func validateKeyModelMaxBudget(v interface{}, k string) ([]string, []error) {
+	var parsed map[string]json.RawMessage
+	if err := json.Unmarshal([]byte(v.(string)), &parsed); err != nil || parsed == nil {
+		return nil, []error{fmt.Errorf("%q must be a JSON object keyed by model name, got %s", k, v)}
+	}
+	for model, cfg := range parsed {
+		var budget map[string]json.RawMessage
+		if err := json.Unmarshal(cfg, &budget); err != nil || len(budget) == 0 {
+			return nil, []error{fmt.Errorf("%q[%q] must be a budget object such as {\"budget_limit\": 50, \"time_period\": \"30d\"}, got %s", k, model, cfg)}
+		}
+		for field := range budget {
+			if !keyModelBudgetFields[field] {
+				return nil, []error{fmt.Errorf("%q[%q] has unknown budget field %q; supported fields are budget_limit, max_budget, time_period, budget_duration, tpm_limit, rpm_limit", k, model, field)}
+			}
+		}
+	}
+	return nil, nil
+}
+
+func parseKeyModelMaxBudget(raw string) map[string]interface{} {
+	var parsed map[string]interface{}
+	if err := json.Unmarshal([]byte(raw), &parsed); err != nil || parsed == nil {
+		return map[string]interface{}{}
+	}
+	return parsed
+}
+
+func keyModelMaxBudgetJSON(modelMaxBudget map[string]interface{}) string {
+	if len(modelMaxBudget) == 0 {
+		return ""
+	}
+	encoded, err := json.Marshal(modelMaxBudget)
+	if err != nil {
+		return ""
+	}
+	return string(encoded)
 }
 
 func resourceKeyCreate(ctx context.Context, d *schema.ResourceData, m interface{}) diag.Diagnostics {
@@ -219,10 +298,12 @@ func resourceKeyRead(ctx context.Context, d *schema.ResourceData, m interface{})
 	}
 
 	if key == nil {
+		log.Printf("[WARN] Key %s not found, removing from state", d.Id())
 		d.SetId("")
 		return nil
 	}
 
+	key.Metadata = declaredKeyMetadata(key.Metadata, d.Get("metadata").(map[string]interface{}))
 	mapKeyToResourceData(d, key)
 	return nil
 }
@@ -232,15 +313,76 @@ func resourceKeyUpdate(ctx context.Context, d *schema.ResourceData, m interface{
 
 	key := &Key{Key: d.Id()}
 	mapResourceDataToKey(d, key)
+	if !d.HasChange("duration") {
+		key.Duration = ""
+	}
+	key.ModelRPMLimit = changedMap(d, "model_rpm_limit")
+	key.ModelTPMLimit = changedMap(d, "model_tpm_limit")
 
-	_, err := c.UpdateKey(key)
+	metadata, err := plannedKeyMetadata(c, d)
 	if err != nil {
+		d.Partial(true)
+		return diag.FromErr(fmt.Errorf("error updating key: %s", err))
+	}
+	key.Metadata = metadata
+
+	if _, err := c.UpdateKey(key); err != nil {
+		d.Partial(true)
 		return diag.FromErr(fmt.Errorf("error updating key: %s", err))
 	}
 
 	return resourceKeyRead(ctx, d, m)
 }
 
+func changedMap(d *schema.ResourceData, name string) map[string]interface{} {
+	if !d.HasChange(name) {
+		return nil
+	}
+	return d.Get(name).(map[string]interface{})
+}
+
+func plannedKeyMetadata(c *Client, d *schema.ResourceData) (map[string]interface{}, error) {
+	if !d.HasChange("metadata") {
+		return nil, nil
+	}
+	current, err := c.GetKey(d.Id())
+	if err != nil {
+		return nil, err
+	}
+	if current == nil {
+		return nil, fmt.Errorf("key %s no longer exists", d.Id())
+	}
+	oldDeclared, newDeclared := d.GetChange("metadata")
+	return mergeKeyMetadata(current.Metadata, oldDeclared.(map[string]interface{}), newDeclared.(map[string]interface{})), nil
+}
+
+func declaredKeyMetadata(server, declared map[string]interface{}) map[string]interface{} {
+	if server == nil {
+		return nil
+	}
+	result := make(map[string]interface{}, len(declared))
+	for k := range declared {
+		if v, ok := server[k]; ok {
+			result[k] = v
+		}
+	}
+	return result
+}
+
+func mergeKeyMetadata(server, oldDeclared, newDeclared map[string]interface{}) map[string]interface{} {
+	result := make(map[string]interface{}, len(server)+len(newDeclared))
+	for k, v := range server {
+		result[k] = v
+	}
+	for k := range oldDeclared {
+		delete(result, k)
+	}
+	for k, v := range newDeclared {
+		result[k] = v
+	}
+	return result
+}
+
 func resourceKeyDelete(ctx context.Context, d *schema.ResourceData, m interface{}) diag.Diagnostics {
 	c := m.(*Client)
 
@@ -285,7 +427,7 @@ func mapResourceDataToKey(d *schema.ResourceData, key *Key) {
 	key.Aliases = d.Get("aliases").(map[string]interface{})
 	key.Config = d.Get("config").(map[string]interface{})
 	key.Permissions = d.Get("permissions").(map[string]interface{})
-	key.ModelMaxBudget = d.Get("model_max_budget").(map[string]interface{})
+	key.ModelMaxBudget = parseKeyModelMaxBudget(d.Get("model_max_budget").(string))
 	key.ModelRPMLimit = d.Get("model_rpm_limit").(map[string]interface{})
 	key.ModelTPMLimit = d.Get("model_tpm_limit").(map[string]interface{})
 	key.Guardrails = expandStringList(d.Get("guardrails").([]interface{}))
@@ -358,9 +500,7 @@ func mapKeyToResourceData(d *schema.ResourceData, key *Key) {
 	if key.Permissions != nil {
 		d.Set("permissions", key.Permissions)
 	}
-	if key.ModelMaxBudget != nil {
-		d.Set("model_max_budget", key.ModelMaxBudget)
-	}
+	d.Set("model_max_budget", keyModelMaxBudgetJSON(key.ModelMaxBudget))
 	if key.ModelRPMLimit != nil {
 		d.Set("model_rpm_limit", key.ModelRPMLimit)
 	}
diff --git a/terraform/provider/litellm/resource_key_test.go b/terraform/provider/litellm/resource_key_test.go
index 91f0061a9ef..66291eadcc5 100644
--- a/terraform/provider/litellm/resource_key_test.go
+++ b/terraform/provider/litellm/resource_key_test.go
@@ -6,9 +6,11 @@ import (
 	"io"
 	"net/http"
 	"net/http/httptest"
+	"reflect"
 	"testing"
 
 	"github.com/hashicorp/terraform-plugin-sdk/v2/helper/schema"
+	"github.com/hashicorp/terraform-plugin-sdk/v2/terraform"
 )
 
 func newKeyResourceData(t *testing.T, raw map[string]interface{}) *schema.ResourceData {
@@ -193,6 +195,102 @@ func TestCreateKeySendsConfigSuppliedKey(t *testing.T) {
 	}
 }
 
+// The proxy validates each model_max_budget entry as a BudgetConfig object and
+// 500s on a bare number, so the JSON string must reach /key/generate as nested
+// objects and the proxy's response must map back to equivalent JSON in state.
+func TestCreateKeySendsModelMaxBudgetAsBudgetObjects(t *testing.T) {
+	var captured map[string]interface{}
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		if r.URL.Path == "/key/generate" {
+			body, _ := io.ReadAll(r.Body)
+			json.Unmarshal(body, &captured)
+			w.Write([]byte(`{"key": "sk-test", "token_id": "hash-1"}`))
+			return
+		}
+		w.Write([]byte(`{"key": "hash-1", "info": {"model_max_budget": {"gpt-4o-mini": {"budget_limit": 50, "time_period": "30d", "rpm_limit": 60}}}}`))
+	}))
+	defer srv.Close()
+
+	client := NewClient(srv.URL, "test-key", true)
+	d := newKeyResourceData(t, map[string]interface{}{
+		"model_max_budget": `{"gpt-4o-mini": {"budget_limit": 50, "time_period": "30d"}}`,
+	})
+
+	if diags := resourceKeyCreate(context.Background(), d, client); diags.HasError() {
+		t.Fatalf("create returned error: %v", diags)
+	}
+
+	budgets, ok := captured["model_max_budget"].(map[string]interface{})
+	if !ok {
+		t.Fatalf("create payload model_max_budget = %v, want object", captured["model_max_budget"])
+	}
+	cfg, ok := budgets["gpt-4o-mini"].(map[string]interface{})
+	if !ok {
+		t.Fatalf("model_max_budget[gpt-4o-mini] = %v, want BudgetConfig object", budgets["gpt-4o-mini"])
+	}
+	if cfg["budget_limit"] != float64(50) || cfg["time_period"] != "30d" {
+		t.Errorf("BudgetConfig = %v, want budget_limit 50 and time_period 30d", cfg)
+	}
+
+	var state map[string]interface{}
+	if err := json.Unmarshal([]byte(d.Get("model_max_budget").(string)), &state); err != nil {
+		t.Fatalf("state model_max_budget %q is not JSON: %v", d.Get("model_max_budget"), err)
+	}
+	if got, _ := state["gpt-4o-mini"].(map[string]interface{}); got["budget_limit"] != float64(50) || got["rpm_limit"] != float64(60) {
+		t.Errorf("state model_max_budget = %v, want the BudgetConfig read back from /key/info", state)
+	}
+}
+
+// Schema version 0 stored model_max_budget as map(number); that state cannot
+// decode into the version 1 string attribute, so the upgrader must drop it.
+func TestKeyStateUpgradeV0DropsMapModelMaxBudget(t *testing.T) {
+	upgraded, err := resourceKey().StateUpgraders[0].Upgrade(context.Background(), map[string]interface{}{
+		"id":               "hash-1",
+		"key_alias":        "legacy",
+		"model_max_budget": map[string]interface{}{"gpt-4o-mini": 50.0},
+	}, nil)
+	if err != nil {
+		t.Fatalf("upgrade returned error: %v", err)
+	}
+	if _, present := upgraded["model_max_budget"]; present {
+		t.Errorf("upgraded state still carries map model_max_budget: %v", upgraded["model_max_budget"])
+	}
+	if upgraded["key_alias"] != "legacy" {
+		t.Errorf("upgrade dropped unrelated attribute: %v", upgraded)
+	}
+}
+
+func TestKeyModelMaxBudgetValidationRequiresBudgetObjects(t *testing.T) {
+	validate := resourceKey().Schema["model_max_budget"].ValidateFunc
+	for _, valid := range []string{
+		`{}`,
+		`{"gpt-4o-mini": {"budget_limit": 50, "time_period": "30d"}}`,
+		`{"gpt-4o-mini": {"max_budget": 50, "rpm_limit": 60}, "gpt-4o": {"budget_duration": "1d", "tpm_limit": 1000}}`,
+	} {
+		if _, errs := validate(valid, "model_max_budget"); len(errs) != 0 {
+			t.Errorf("validate(%s) = %v, want accepted", valid, errs)
+		}
+	}
+	for _, invalid := range []string{
+		`null`,
+		`[]`,
+		`"gpt-4o-mini"`,
+		`50`,
+		`{"gpt-4o-mini": 50}`,
+		`{"gpt-4o-mini": null}`,
+		`{"gpt-4o-mini": [50]}`,
+		`{"gpt-4o-mini": {}}`,
+		`{"gpt-4o-mini": {"budget_limt": 50}}`,
+		`{"gpt-4o-mini": {"budget_limit": 50, "max_tokens": 100}}`,
+		`not json`,
+	} {
+		if _, errs := validate(invalid, "model_max_budget"); len(errs) == 0 {
+			t.Errorf("validate(%s) accepted a value that would send no per-model budget", invalid)
+		}
+	}
+}
+
 // The proxy 400s on budget_duration: "", so an unset duration must be
 // omitted from the update payload entirely.
 func TestUpdateKeyOmitsEmptyBudgetDuration(t *testing.T) {
@@ -221,6 +319,47 @@ func TestUpdateKeyOmitsEmptyBudgetDuration(t *testing.T) {
 	}
 }
 
+func TestResourceKeyUpdateFailureKeepsPriorState(t *testing.T) {
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		if r.URL.Path == "/key/update" {
+			w.WriteHeader(http.StatusBadRequest)
+			w.Write([]byte(`{"error":{"message":"Invalid budget_duration 'bad'"}}`))
+			return
+		}
+		w.Write([]byte(`{"key":"hash-1","info":{"key_alias":"demo","models":["fake-model"]}}`))
+	}))
+	defer srv.Close()
+
+	res := resourceKey()
+	priorData := newKeyResourceData(t, map[string]interface{}{
+		"key_alias": "demo",
+		"models":    []interface{}{"fake-model"},
+	})
+	priorData.SetId("hash-1")
+	prior := priorData.State()
+	config := terraform.NewResourceConfigRaw(map[string]interface{}{
+		"key_alias":       "demo",
+		"models":          []interface{}{"fake-model"},
+		"budget_duration": "bad",
+	})
+	diff, err := res.Diff(context.Background(), prior, config, nil)
+	if err != nil {
+		t.Fatalf("diff failed: %v", err)
+	}
+
+	newState, diags := res.Apply(context.Background(), prior, diff, NewClient(srv.URL, "test-key", true))
+	if !diags.HasError() {
+		t.Fatal("apply succeeded, want the proxy's 400 surfaced as an error")
+	}
+	if got, ok := newState.Attributes["budget_duration"]; ok {
+		t.Errorf("failed update persisted budget_duration=%q into state, want it absent", got)
+	}
+	if newState.Attributes["key_alias"] != "demo" {
+		t.Errorf("prior key_alias lost from state: %v", newState.Attributes)
+	}
+}
+
 // /key/info nests the key's fields under "info"; GetKey must unwrap that
 // envelope or reads map nothing back into state.
 func TestGetKeyUnwrapsInfoEnvelope(t *testing.T) {
@@ -254,3 +393,296 @@ func TestGetKeyUnwrapsInfoEnvelope(t *testing.T) {
 		t.Errorf("RPMLimit not parsed: %+v", key.RPMLimit)
 	}
 }
+
+func TestGetKeyReadsFieldsStoredInMetadata(t *testing.T) {
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		w.Write([]byte(`{
+			"key": "hash-1",
+			"info": {
+				"models": ["gpt-4o-mini"],
+				"metadata": {
+					"team": "core-infra",
+					"model_rpm_limit": {"gpt-4o-mini": 7},
+					"model_tpm_limit": {"gpt-4o-mini": 10000},
+					"guardrails": ["pii-guard"],
+					"tags": ["prod"],
+					"enforced_params": ["user"],
+					"allowed_passthrough_routes": ["/v1/foo"],
+					"rpm_limit_type": "guaranteed_throughput",
+					"tpm_limit_type": "dynamic",
+					"prompts": ["p1"]
+				}
+			}
+		}`))
+	}))
+	defer srv.Close()
+
+	client := NewClient(srv.URL, "test-key", true)
+	key, err := client.GetKey("hash-1")
+	if err != nil {
+		t.Fatalf("GetKey returned error: %v", err)
+	}
+	if got, ok := key.ModelRPMLimit["gpt-4o-mini"].(float64); !ok || got != 7 {
+		t.Errorf("ModelRPMLimit = %v, want gpt-4o-mini=7 read from metadata", key.ModelRPMLimit)
+	}
+	if got, ok := key.ModelTPMLimit["gpt-4o-mini"].(float64); !ok || got != 10000 {
+		t.Errorf("ModelTPMLimit = %v, want gpt-4o-mini=10000 read from metadata", key.ModelTPMLimit)
+	}
+	if len(key.Guardrails) != 1 || key.Guardrails[0] != "pii-guard" {
+		t.Errorf("Guardrails = %v, want [pii-guard]", key.Guardrails)
+	}
+	if len(key.Tags) != 1 || key.Tags[0] != "prod" {
+		t.Errorf("Tags = %v, want [prod]", key.Tags)
+	}
+	if len(key.EnforcedParams) != 1 || key.EnforcedParams[0] != "user" {
+		t.Errorf("EnforcedParams = %v, want [user]", key.EnforcedParams)
+	}
+	if len(key.AllowedPassthroughRoutes) != 1 || key.AllowedPassthroughRoutes[0] != "/v1/foo" {
+		t.Errorf("AllowedPassthroughRoutes = %v, want [/v1/foo]", key.AllowedPassthroughRoutes)
+	}
+	if key.RPMLimitType != "guaranteed_throughput" || key.TPMLimitType != "dynamic" {
+		t.Errorf("limit types = %q/%q, want guaranteed_throughput/dynamic", key.RPMLimitType, key.TPMLimitType)
+	}
+	if len(key.Prompts) != 1 || key.Prompts[0] != "p1" {
+		t.Errorf("Prompts = %v, want [p1]", key.Prompts)
+	}
+	if key.Metadata["team"] != "core-infra" {
+		t.Errorf("Metadata = %v, want team=core-infra preserved", key.Metadata)
+	}
+}
+
+func TestGetKeyPrefersTopLevelOverMetadataCopy(t *testing.T) {
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		w.Write([]byte(`{
+			"key": "hash-1",
+			"info": {
+				"tags": ["top-level"],
+				"guardrails": null,
+				"metadata": {
+					"tags": ["from-metadata"],
+					"guardrails": ["from-metadata"]
+				}
+			}
+		}`))
+	}))
+	defer srv.Close()
+
+	client := NewClient(srv.URL, "test-key", true)
+	key, err := client.GetKey("hash-1")
+	if err != nil {
+		t.Fatalf("GetKey returned error: %v", err)
+	}
+	if len(key.Tags) != 1 || key.Tags[0] != "top-level" {
+		t.Errorf("Tags = %v, want [top-level]", key.Tags)
+	}
+	if len(key.Guardrails) != 1 || key.Guardrails[0] != "from-metadata" {
+		t.Errorf("Guardrails = %v, want [from-metadata] (null top-level must not shadow)", key.Guardrails)
+	}
+}
+
+func TestResourceKeyReadDropsMissingKeyFromState(t *testing.T) {
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		w.WriteHeader(http.StatusNotFound)
+		w.Write([]byte(`{"error":{"message":"Key not found in database","type":"not_found_error","param":"key","code":"404"}}`))
+	}))
+	defer srv.Close()
+
+	d := newKeyResourceData(t, map[string]interface{}{"key_alias": "stale"})
+	d.SetId("deleted-out-of-band")
+
+	diags := resourceKeyRead(context.Background(), d, NewClient(srv.URL, "test-key", true))
+	if diags.HasError() {
+		t.Fatalf("read of a missing key must not error, got: %v", diags)
+	}
+	if d.Id() != "" {
+		t.Errorf("Id = %q, want empty so Terraform plans a recreate", d.Id())
+	}
+}
+
+func TestResourceKeyReadStillFailsOnNon404Errors(t *testing.T) {
+	srv := httptest.NewServer(http.HandlerFunc(func(w http.ResponseWriter, r *http.Request) {
+		w.WriteHeader(http.StatusInternalServerError)
+		w.Write([]byte(`{"error":{"message":"db down"}}`))
+	}))
+	defer srv.Close()
+
+	d := newKeyResourceData(t, map[string]interface{}{"key_alias": "live"})
+	d.SetId("still-exists")
+
+	diags := resourceKeyRead(context.Background(), d, NewClient(srv.URL, "test-key", true))
+	if !diags.HasError() {
+		t.Fatal("a 500 from /key/info must surface as an error, not be treated as a deleted key")
+	}
+	if d.Id() != "still-exists" {
+		t.Errorf("Id = %q, want unchanged on a transient error", d.Id())
+	}
+}
+
+// fakeKeyProxy serves /key/info from stored metadata and applies /key/update
+// the way the proxy does: an absent "metadata" keeps the stored map, a
+// present one replaces it wholesale.
+type fakeKeyProxy struct {
+	metadata map[string]interface{}
+	updates  []map[string]interface{}
+}
+
+func (p *fakeKeyProxy) handler() http.HandlerFunc {
+	return func(w http.ResponseWriter, r *http.Request) {
+		w.Header().Set("Content-Type", "application/json")
+		switch r.URL.Path {
+		case "/key/info":
+			json.NewEncoder(w).Encode(map[string]interface{}{
+				"key":  "hash-1",
+				"info": map[string]interface{}{"key_alias": "alias-1", "models": []string{"gpt-4o-mini"}, "metadata": p.metadata},
+			})
+		case "/key/update":
+			var body map[string]interface{}
+			json.NewDecoder(r.Body).Decode(&body)
+			p.updates = append(p.updates, body)
+			if m, ok := body["metadata"].(map[string]interface{}); ok {
+				p.metadata = m
+			}
+			json.NewEncoder(w).Encode(map[string]interface{}{"key": "hash-1", "metadata": p.metadata})
+		default:
+			http.NotFound(w, r)
+		}
+	}
+}
+
+func applyKeyUpdate(t *testing.T, client *Client, stateAttrs map[string]string, config map[string]interface{}) *terraform.InstanceState {
+	t.Helper()
+	r := resourceKey()
+	state := &terraform.InstanceState{ID: "hash-1", Attributes: stateAttrs}
+	diff, err := r.Diff(context.Background(), state, terraform.NewResourceConfigRaw(config), client)
+	if err != nil {
+		t.Fatalf("Diff returned error: %v", err)
+	}
+	if diff == nil {
+		t.Fatalf("expected a non-empty diff between %v and %v", stateAttrs, config)
+	}
+	newState, diags := r.Apply(context.Background(), state, diff, client)
+	if diags.HasError() {
+		t.Fatalf("Apply returned error: %v", diags)
+	}
+	return newState
+}
+
+func TestKeyUpdateWithoutMetadataChangePreservesServerMetadata(t *testing.T) {
+	proxy := &fakeKeyProxy{metadata: map[string]interface{}{"a": "1", "server_side": "x", "model_rpm_limit": map[string]interface{}{"gpt-4o-mini": float64(5)}}}
+	srv := httptest.NewServer(proxy.handler())
+	defer srv.Close()
+	client := NewClient(srv.URL, "test-key", true)
+
+	newState := applyKeyUpdate(t, client,
+		map[string]string{"key_alias": "alias-1", "max_budget": "10", "metadata.%": "1", "metadata.a": "1"},
+		map[string]interface{}{"key_alias": "alias-1", "max_budget": 20, "metadata": map[string]interface{}{"a": "1"}},
+	)
+
+	if len(proxy.updates) != 1 {
+		t.Fatalf("expected one /key/update call, got %d", len(proxy.updates))
+	}
+	for _, field := range []string{"metadata", "model_rpm_limit", "model_tpm_limit"} {
+		if _, present := proxy.updates[0][field]; present {
+			t.Errorf("unchanged %q was sent on /key/update: %v", field, proxy.updates[0][field])
+		}
+	}
+	if proxy.metadata["server_side"] != "x" {
+		t.Errorf("server-side metadata lost: %v", proxy.metadata)
+	}
+	if got := newState.Attributes["metadata.%"]; got != "1" {
+		t.Errorf("state metadata should hold only the declared entry, got %v", newState.Attributes)
+	}
+	if got := newState.Attributes["metadata.a"]; got != "1" {
+		t.Errorf("metadata.a = %q, want 1", got)
+	}
+}
+
+func TestKeyUpdateWithMetadataChangeMergesOverServerMetadata(t *testing.T) {
+	proxy := &fakeKeyProxy{metadata: map[string]interface{}{"a": "1", "b": "2", "server_side": "x"}}
+	srv := httptest.NewServer(proxy.handler())
+	defer srv.Close()
+	client := NewClient(srv.URL, "test-key", true)
+
+	applyKeyUpdate(t, client,
+		map[string]string{"key_alias": "alias-1", "metadata.%": "2", "metadata.a": "1", "metadata.b": "2"},
+		map[string]interface{}{"key_alias": "alias-1", "metadata": map[string]interface{}{"a": "2", "c": "3"}},
+	)
+
+	want := map[string]interface{}{"a": "2", "c": "3", "server_side": "x"}
+	if !reflect.DeepEqual(proxy.metadata, want) {
+		t.Errorf("metadata after update = %v, want %v", proxy.metadata, want)
+	}
+}
+
+func TestKeyUpdateSendsChangedModelLimits(t *testing.T) {
+	proxy := &fakeKeyProxy{metadata: map[string]interface{}{}}
+	srv := httptest.NewServer(proxy.handler())
+	defer srv.Close()
+	client := NewClient(srv.URL, "test-key", true)
+
+	applyKeyUpdate(t, client,
+		map[string]string{"key_alias": "alias-1", "model_rpm_limit.%": "1", "model_rpm_limit.gpt-4o-mini": "5"},
+		map[string]interface{}{"key_alias": "alias-1", "model_rpm_limit": map[string]interface{}{"gpt-4o-mini": 7}},
+	)
+
+	got, ok := proxy.updates[0]["model_rpm_limit"].(map[string]interface{})
+	if !ok || got["gpt-4o-mini"] != float64(7) {
+		t.Errorf("changed model_rpm_limit not sent: %v", proxy.updates[0])
+	}
+}
+
+func TestKeyReadKeepsOnlyDeclaredMetadata(t *testing.T) {
+	proxy := &fakeKeyProxy{metadata: map[string]interface{}{"a": "1", "server_side": "x"}}
+	srv := httptest.NewServer(proxy.handler())
+	defer srv.Close()
+	client := NewClient(srv.URL, "test-key", true)
+
+	d := newKeyResourceData(t, map[string]interface{}{"metadata": map[string]interface{}{"a": "1"}})
+	d.SetId("hash-1")
+	if diags := resourceKeyRead(context.Background(), d, client); diags.HasError() {
+		t.Fatalf("Read returned error: %v", diags)
+	}
+
+	want := map[string]interface{}{"a": "1"}
+	if got := d.Get("metadata"); !reflect.DeepEqual(got, want) {
+		t.Errorf("metadata in state = %v, want %v", got, want)
+	}
+}
+
+func TestKeyUpdateSendsChangedDuration(t *testing.T) {
+	proxy := &fakeKeyProxy{metadata: map[string]interface{}{}}
+	srv := httptest.NewServer(proxy.handler())
+	defer srv.Close()
+	client := NewClient(srv.URL, "test-key", true)
+
+	applyKeyUpdate(t, client,
+		map[string]string{"key_alias": "alias-1", "duration": "30d"},
+		map[string]interface{}{"key_alias": "alias-1", "duration": "90d"},
+	)
+
+	if got := proxy.updates[0]["duration"]; got != "90d" {
+		t.Errorf("update payload duration = %v, want 90d", got)
+	}
+}
+
+func TestKeyUpdateOmitsUnchangedDuration(t *testing.T) {
+	proxy := &fakeKeyProxy{metadata: map[string]interface{}{}}
+	srv := httptest.NewServer(proxy.handler())
+	defer srv.Close()
+	client := NewClient(srv.URL, "test-key", true)
+
+	applyKeyUpdate(t, client,
+		map[string]string{"key_alias": "alias-1", "duration": "30d"},
+		map[string]interface{}{"key_alias": "alias-2", "duration": "30d"},
+	)
+
+	if got := proxy.updates[0]["key_alias"]; got != "alias-2" {
+		t.Fatalf("update payload key_alias = %v, want alias-2", got)
+	}
+	if v, present := proxy.updates[0]["duration"]; present {
+		t.Errorf("update payload unexpectedly contains duration = %v", v)
+	}
+}
diff --git a/terraform/provider/litellm/resource_key_utils.go b/terraform/provider/litellm/resource_key_utils.go
index d426fec05b2..7046ef7097a 100644
--- a/terraform/provider/litellm/resource_key_utils.go
+++ b/terraform/provider/litellm/resource_key_utils.go
@@ -65,7 +65,7 @@ func buildKeyData(d *schema.ResourceData) map[string]interface{} {
 		keyData["permissions"] = v.(map[string]interface{})
 	}
 	if v, ok := d.GetOkExists("model_max_budget"); ok {
-		keyData["model_max_budget"] = v.(map[string]interface{})
+		keyData["model_max_budget"] = parseKeyModelMaxBudget(v.(string))
 	}
 	if v, ok := d.GetOkExists("model_rpm_limit"); ok {
 		keyData["model_rpm_limit"] = v.(map[string]interface{})
@@ -107,7 +107,7 @@ func setKeyResourceData(d *schema.ResourceData, key *Key) error {
 		"aliases":                key.Aliases,
 		"config":                 key.Config,
 		"permissions":            key.Permissions,
-		"model_max_budget":       key.ModelMaxBudget,
+		"model_max_budget":       keyModelMaxBudgetJSON(key.ModelMaxBudget),
 		"model_rpm_limit":        key.ModelRPMLimit,
 		"model_tpm_limit":        key.ModelTPMLimit,
 		"guardrails":             key.Guardrails,
diff --git a/terraform/provider/litellm/resource_team.go b/terraform/provider/litellm/resource_team.go
index 24c47843cd1..bf7d2508077 100644
--- a/terraform/provider/litellm/resource_team.go
+++ b/terraform/provider/litellm/resource_team.go
@@ -31,6 +31,13 @@ func ResourceLiteLLMTeam() *schema.Resource {
 		},
 
 		Schema: map[string]*schema.Schema{
+			"team_id": {
+				Type:        schema.TypeString,
+				Optional:    true,
+				Computed:    true,
+				ForceNew:    true,
+				Description: "Unique ID for the team. Generated by the provider if not provided",
+			},
 			"team_alias": {
 				Type:     schema.TypeString,
 				Required: true,
@@ -162,7 +169,7 @@ func ResourceLiteLLMTeam() *schema.Resource {
 func resourceLiteLLMTeamCreate(d *schema.ResourceData, m interface{}) error {
 	client := m.(*Client)
 
-	teamID := uuid.New().String()
+	teamID := resolveTeamID(d)
 	teamData := buildTeamData(d, teamID)
 
 	// Throughput limit types are only accepted by /team/new, not /team/update.
@@ -214,6 +221,7 @@ func resourceLiteLLMTeamRead(d *schema.ResourceData, m interface{}) error {
 	teamResp := infoResp.TeamInfo
 
 	// Update the state with values from the response or fall back to the data passed in during creation
+	d.Set("team_id", d.Id())
 	d.Set("team_alias", GetStringValue(teamResp.TeamAlias, d.Get("team_alias").(string)))
 	d.Set("organization_id", GetStringValue(teamResp.OrganizationID, d.Get("organization_id").(string)))
 
@@ -263,11 +271,11 @@ func resourceLiteLLMTeamRead(d *schema.ResourceData, m interface{}) error {
 		d.Set("team_member_tpm_limit", *teamResp.TeamMemberTPMLimit)
 	}
 	d.Set("team_member_key_duration", GetStringValue(teamResp.TeamMemberKeyDuration, d.Get("team_member_key_duration").(string)))
-	if teamResp.ModelRPMLimit != nil {
-		d.Set("model_rpm_limit", teamResp.ModelRPMLimit)
+	if v := teamModelLimit(teamResp.ModelRPMLimit, teamResp.Metadata, "model_rpm_limit"); v != nil {
+		d.Set("model_rpm_limit", v)
 	}
-	if teamResp.ModelTPMLimit != nil {
-		d.Set("model_tpm_limit", teamResp.ModelTPMLimit)
+	if v := teamModelLimit(teamResp.ModelTPMLimit, teamResp.Metadata, "model_tpm_limit"); v != nil {
+		d.Set("model_tpm_limit", v)
 	}
 	if teamResp.AllowedPassthroughRoutes != nil {
 		d.Set("allowed_passthrough_routes", teamResp.AllowedPassthroughRoutes)
@@ -354,6 +362,13 @@ func resourceLiteLLMTeamDelete(d *schema.ResourceData, m interface{}) error {
 	return nil
 }
 
+func resolveTeamID(d *schema.ResourceData) string {
+	if v, ok := d.GetOk("team_id"); ok {
+		return v.(string)
+	}
+	return uuid.New().String()
+}
+
 func buildTeamData(d *schema.ResourceData, teamID string) map[string]interface{} {
 	teamData := map[string]interface{}{
 		"team_id":    teamID,
@@ -364,14 +379,19 @@ func buildTeamData(d *schema.ResourceData, teamID string) map[string]interface{}
 		"organization_id", "tpm_limit", "rpm_limit", "max_budget", "budget_duration", "models",
 		"blocked", "team_member_permissions", "model_aliases", "guardrails", "prompts",
 		"team_member_budget", "team_member_budget_duration", "team_member_rpm_limit",
-		"team_member_tpm_limit", "team_member_key_duration", "model_rpm_limit",
-		"model_tpm_limit", "allowed_passthrough_routes",
+		"team_member_tpm_limit", "team_member_key_duration", "allowed_passthrough_routes",
 	} {
 		if v, ok := d.GetOk(key); ok {
 			teamData[key] = v
 		}
 	}
 
+	for _, key := range []string{"model_rpm_limit", "model_tpm_limit"} {
+		if v, ok := d.GetOk(key); ok || d.HasChange(key) {
+			teamData[key] = v
+		}
+	}
+
 	if v, ok := d.GetOk("soft_budget"); ok {
 		teamData["soft_budget"] = v
 	} else if d.HasChange("soft_budget") {
@@ -404,6 +424,14 @@ func buildTeamMetadata(d *schema.ResourceData) map[string]interface{} {
 	return metadata
 }
 
+func teamModelLimit(topLevel, metadata map[string]interface{}, key string) map[string]interface{} {
+	if topLevel != nil {
+		return topLevel
+	}
+	nested, _ := metadata[key].(map[string]interface{})
+	return nested
+}
+
 func splitTeamMetadata(raw map[string]interface{}) (map[string]string, []string, []string) {
 	metadata := map[string]string{}
 	var tags, alertEmails []string
diff --git a/terraform/provider/litellm/resource_team_test.go b/terraform/provider/litellm/resource_team_test.go
index 9638378cdfe..35d60401d30 100644
--- a/terraform/provider/litellm/resource_team_test.go
+++ b/terraform/provider/litellm/resource_team_test.go
@@ -9,6 +9,7 @@ import (
 	"reflect"
 	"testing"
 
+	"github.com/google/uuid"
 	"github.com/hashicorp/terraform-plugin-sdk/v2/helper/schema"
 	"github.com/hashicorp/terraform-plugin-sdk/v2/terraform"
 )
@@ -85,6 +86,87 @@ func TestTeamCreateSendsSoftBudgetTagsAndAlertEmails(t *testing.T) {
 	}
 }
 
+func TestTeamCreateSendsConfiguredTeamID(t *testing.T) {
+	var captured map[string]interface{}
+	srv := newTeamTestServer(t, &captured, `{"team_id":"platform-team","team_info":{"team_id":"platform-team","team_alias":"platform"},"keys":[],"team_memberships":[]}`)
+	defer srv.Close()
+
+	d := newTeamResourceData(t, map[string]interface{}{
+		"team_id":    "platform-team",
+		"team_alias": "platform",
+	})
+
+	if err := resourceLiteLLMTeamCreate(d, NewClient(srv.URL, "test-key", true)); err != nil {
+		t.Fatalf("create failed: %v", err)
+	}
+
+	if got := captured["team_id"]; got != "platform-team" {
+		t.Fatalf("payload team_id = %v, want platform-team", got)
+	}
+	if got := d.Id(); got != "platform-team" {
+		t.Fatalf("resource id = %q, want platform-team", got)
+	}
+	if got := d.Get("team_id"); got != "platform-team" {
+		t.Fatalf("state team_id = %v, want platform-team", got)
+	}
+}
+
+func TestTeamCreateGeneratesTeamIDWhenUnset(t *testing.T) {
+	var captured map[string]interface{}
+	srv := newTeamTestServer(t, &captured, `{"team_id":"x","team_info":{"team_alias":"eng"},"keys":[],"team_memberships":[]}`)
+	defer srv.Close()
+
+	d := newTeamResourceData(t, map[string]interface{}{"team_alias": "eng"})
+
+	if err := resourceLiteLLMTeamCreate(d, NewClient(srv.URL, "test-key", true)); err != nil {
+		t.Fatalf("create failed: %v", err)
+	}
+
+	sent, _ := captured["team_id"].(string)
+	if _, err := uuid.Parse(sent); err != nil {
+		t.Fatalf("payload team_id = %q, want a generated UUID: %v", sent, err)
+	}
+	if d.Id() != sent || d.Get("team_id") != sent {
+		t.Fatalf("id = %q, state team_id = %v, want both to equal the sent id %q", d.Id(), d.Get("team_id"), sent)
+	}
+}
+
+func TestTeamReadSetsTeamIDFromResourceID(t *testing.T) {
+	var captured map[string]interface{}
+	srv := newTeamTestServer(t, &captured, `{"team_id":"imported-team","team_info":{"team_id":"imported-team","team_alias":"imported"},"keys":[],"team_memberships":[]}`)
+	defer srv.Close()
+
+	d := newTeamResourceData(t, map[string]interface{}{})
+	d.SetId("imported-team")
+
+	if err := resourceLiteLLMTeamRead(d, NewClient(srv.URL, "test-key", true)); err != nil {
+		t.Fatalf("read failed: %v", err)
+	}
+	if got := d.Get("team_id"); got != "imported-team" {
+		t.Fatalf("team_id = %v, want imported-team", got)
+	}
+}
+
+func TestTeamIDChangeForcesReplacement(t *testing.T) {
+	res := ResourceLiteLLMTeam()
+	priorData := schema.TestResourceDataRaw(t, res.Schema, map[string]interface{}{
+		"team_id":    "old-team",
+		"team_alias": "eng",
+	})
+	priorData.SetId("old-team")
+	config := terraform.NewResourceConfigRaw(map[string]interface{}{
+		"team_id":    "new-team",
+		"team_alias": "eng",
+	})
+	diff, err := res.Diff(context.Background(), priorData.State(), config, nil)
+	if err != nil {
+		t.Fatalf("diff failed: %v", err)
+	}
+	if diff == nil || !diff.RequiresNew() {
+		t.Fatalf("changing team_id must force replacement, diff = %+v", diff)
+	}
+}
+
 func TestTeamReadMapsTeamInfoEnvelope(t *testing.T) {
 	var captured map[string]interface{}
 	srv := newTeamTestServer(t, &captured, teamInfoWithSoftBudget)
@@ -250,6 +332,77 @@ func TestTeamReadMapsNewFields(t *testing.T) {
 	}
 }
 
+func TestTeamReadMapsPerModelLimitsFromMetadata(t *testing.T) {
+	var captured map[string]interface{}
+	srv := newTeamTestServer(t, &captured, `{
+		"team_id": "team-1",
+		"team_info": {
+			"team_id": "team-1",
+			"team_alias": "eng",
+			"model_rpm_limit": null,
+			"model_tpm_limit": null,
+			"metadata": {
+				"department": "eng",
+				"model_rpm_limit": {"gpt-4o-mini": 250},
+				"model_tpm_limit": {"gpt-4o-mini": 5000}
+			}
+		}
+	}`)
+	defer srv.Close()
+
+	d := newTeamResourceData(t, map[string]interface{}{
+		"team_alias":      "eng",
+		"model_rpm_limit": map[string]interface{}{"gpt-4o-mini": 100},
+	})
+	d.SetId("team-1")
+
+	if err := resourceLiteLLMTeamRead(d, NewClient(srv.URL, "test-key", true)); err != nil {
+		t.Fatalf("read returned error: %v", err)
+	}
+	if got := d.Get("model_rpm_limit"); !reflect.DeepEqual(got, map[string]interface{}{"gpt-4o-mini": 250}) {
+		t.Errorf("model_rpm_limit = %v, want server value 250", got)
+	}
+	if got := d.Get("model_tpm_limit"); !reflect.DeepEqual(got, map[string]interface{}{"gpt-4o-mini": 5000}) {
+		t.Errorf("model_tpm_limit = %v, want server value 5000", got)
+	}
+	if got := d.Get("metadata"); !reflect.DeepEqual(got, map[string]interface{}{"department": "eng"}) {
+		t.Errorf("metadata = %v, want per-model limits kept out of the string map", got)
+	}
+}
+
+func TestTeamUpdateClearsRemovedPerModelLimits(t *testing.T) {
+	var captured map[string]interface{}
+	srv := newTeamTestServer(t, &captured, `{"team_id":"team-1","team_info":{"team_id":"team-1","team_alias":"eng"}}`)
+	defer srv.Close()
+
+	res := ResourceLiteLLMTeam()
+	priorData := schema.TestResourceDataRaw(t, res.Schema, map[string]interface{}{
+		"team_alias":      "eng",
+		"model_rpm_limit": map[string]interface{}{"gpt-4o-mini": 100},
+		"model_tpm_limit": map[string]interface{}{"gpt-4o-mini": 5000},
+	})
+	priorData.SetId("team-1")
+	prior := priorData.State()
+	config := terraform.NewResourceConfigRaw(map[string]interface{}{"team_alias": "eng"})
+	diff, err := res.Diff(context.Background(), prior, config, nil)
+	if err != nil {
+		t.Fatalf("diff failed: %v", err)
+	}
+	d, err := schema.InternalMap(res.Schema).Data(prior, diff)
+	if err != nil {
+		t.Fatalf("data failed: %v", err)
+	}
+
+	if err := resourceLiteLLMTeamUpdate(d, NewClient(srv.URL, "test-key", true)); err != nil {
+		t.Fatalf("update failed: %v", err)
+	}
+	for _, k := range []string{"model_rpm_limit", "model_tpm_limit"} {
+		if got, ok := captured[k]; !ok || !reflect.DeepEqual(got, map[string]interface{}{}) {
+			t.Errorf("payload %s = %v (present=%v), want explicit empty map", k, got, ok)
+		}
+	}
+}
+
 // rpm_limit_type / tpm_limit_type are accepted by /team/new but not
 // /team/update, so create must send them and update must not.
 func TestTeamLimitTypesSentOnCreateOnly(t *testing.T) {
diff --git a/tests/code_coverage_tests/router_code_coverage.py b/tests/code_coverage_tests/router_code_coverage.py
index 0af29f069c6..a11f015743b 100644
--- a/tests/code_coverage_tests/router_code_coverage.py
+++ b/tests/code_coverage_tests/router_code_coverage.py
@@ -87,6 +87,7 @@ ignored_function_names = [
     "_delete_claude_code_session_router_binding",  # Tested through Redis cleanup failure in test_router.py
     "_resolve_claude_code_session_router",  # Tested through Claude Code session routing in test_router.py
     "_get_claude_code_session_router_binding",  # Tested through the two-worker session routing test in test_router.py
+    "_apply_updated_routing_strategy_args",  # Tested via update_settings in test_lowest_latency.py (file lacks "router" in name)
 ]
 
 
diff --git a/tests/e2e/CLAUDE.md b/tests/e2e/CLAUDE.md
index 89c04208d65..34fbe9d9247 100644
--- a/tests/e2e/CLAUDE.md
+++ b/tests/e2e/CLAUDE.md
@@ -181,13 +181,15 @@ quota_management.<behavior>.<variant>.<assertion>
                                | team_multi_window | fallback | spend_counter
               <spend_tracking> chat_completions | stream | messages_bridge | embeddings
                                | cache_hit | key_rollup | concurrent_burst | tags | end_user
-                               | per_model | failure | spend_calculate | pagination
+                               | per_model | failure | spend_calculate | pagination | key_attribution
   assertion : blocks_over_limit | resets_after_window | headers_report_remaining | picks_under_tpm
               | blocks_then_resets | resets_windows_independently | alerts_without_blocking
               | isolates_per_model | isolates_per_member | isolates_per_group | enforced_across_keys
               | routes_to_fallback | reseed_matches_db | reports_spend | logs_cost | zero_cost
               | matches_sum_of_logs | loses_no_spend | attributes_spend | writes_own_rows
-              | writes_failure_row | returns_cost | keeps_total
+              | writes_failure_row | returns_cost | keeps_total | joins_key | reports_alias_and_email
+              | health_rows_keep_service_account | retrieve_batch_cost_joins_retrieving_key
+              | poller_batch_cost_joins_creating_key
   e.g.  quota_management.ratelimit.rpm.blocks_over_limit           exercised_on=[chat_completions, messages]
         quota_management.budget.key.blocks_over_limit              exercised_on=[chat_completions]
 ```
diff --git a/tests/e2e/batches/COVERAGE.md b/tests/e2e/batches/COVERAGE.md
index 8a7b68511ec..919c39f21a2 100644
--- a/tests/e2e/batches/COVERAGE.md
+++ b/tests/e2e/batches/COVERAGE.md
@@ -120,6 +120,36 @@ create traverse gateway -> gateway -> OpenAI (LIT-5347, PR #36240). The pin:
 nested managed ids round-trip retrieve. This self-chaining only needs the proxy to
 reach its own `PROXY_BASE_URL`, which holds both locally and on the e2e stage.
 
+## Cleanup
+
+Batch teardown cancels active batches before deleting their input files and keys.
+Raw file IDs from both `model_param` and `provider_fallback` uploads use the upload
+provider when deleted. Model-encoded and managed file IDs route themselves
+
+File deletion and batch cancellation check their responses and retry transient
+failures up to three times. Teardown attempts every registered cleanup before
+reporting failures as test errors. Already deleted files and batches that are
+terminal are safe to clean up again. Managed batch cancellation polls for up to eleven minutes
+before input deletion: the ten-minute provider window plus a propagation margin.
+Accepted cancellation may still report validating or in_progress while the provider
+updates its state. Raw and model-encoded batches are polled until cancelling or
+terminal before input deletion. OpenAI and Azure lifecycle cleanup also deletes
+output and error files returned by terminal batches. Bedrock deletion uses a signed S3 DELETE
+restricted to the configured storage buckets and managed file prefixes. The low-RPM
+test submits with its restricted key and cleans up with the test administrator key
+
+Managed deletion forwards the deployment's trusted bucket configuration and returns
+the requested managed file ID even when stored output metadata carries a provider ID
+
+Azure input uploads request `expires_after` anchored to `created_at` with
+`seconds=1209600`, and the lifecycle tests check the returned expiry. This is a
+fallback for interrupted runs: immediate deletion remains the normal cleanup.
+Azure's minimum supported native expiry is 14 days, so a three-day expiry cannot
+be requested through its Files API
+
+The Azure entry in `files_settings` must use `api_version: 2025-04-01-preview`
+for raw uploads to honor expiry, matching the batch deployment's API version
+
 ## Terminal state + cost write-back (cross-run marker baton)
 
 The 24h completion window rules out submit-and-wait inside one run, so
diff --git a/tests/e2e/batches/batch_cleanup.py b/tests/e2e/batches/batch_cleanup.py
new file mode 100644
index 00000000000..9284882ad82
--- /dev/null
+++ b/tests/e2e/batches/batch_cleanup.py
@@ -0,0 +1,140 @@
+from builtins import ExceptionGroup
+from collections.abc import Callable
+from itertools import count
+from time import monotonic, sleep
+from typing import Final, Protocol
+
+from batch_client import BatchObject, FileDeleteResponse
+from capabilities import is_managed_id
+from e2e_http import NetworkError, RateLimitedError, Result, Success, UnknownApiError
+from pydantic import BaseModel
+
+CLEANUP_DELAYS: Final = (1.0, 2.0, 4.0)
+BATCH_TERMINAL_STATUSES: Final = frozenset({"completed", "failed", "expired", "cancelled"})
+BATCH_PENDING_STATUSES: Final = frozenset({"validating", "in_progress", "finalizing", "cancelling"})
+BATCH_CANCEL_TIMEOUT_SECONDS: Final = 660.0
+BATCH_CANCEL_POLL_SECONDS: Final = 10.0
+
+
+class BatchCleanupClient(Protocol):
+    def delete_file(self, file_id: str, *, key: str, provider: str | None = None) -> Result[FileDeleteResponse]: ...
+
+    def retrieve_batch(self, batch_id: str, *, key: str, provider: str | None = None) -> Result[BatchObject]: ...
+
+    def cancel_batch(self, batch_id: str, *, key: str, provider: str | None = None) -> Result[BatchObject]: ...
+
+
+def cleanup_result[R: BaseModel](
+    action: Callable[[], Result[R]], *, wait: Callable[[float], None] = sleep
+) -> Result[R]:
+    for delay, result in ((delay, action()) for delay in CLEANUP_DELAYS):
+        match result:
+            case NetworkError() | RateLimitedError():
+                wait(delay)
+            case UnknownApiError(status_code=code) if code in {408, 429, 500, 502, 503, 504}:
+                wait(delay)
+            case _:
+                return result
+    return action()
+
+
+def _require_cleanup_success[R: BaseModel](result: Result[R], operation: str) -> R:
+    match result:
+        case Success(data=data):
+            return data
+        case UnknownApiError(status_code=code):
+            raise AssertionError(f"{operation} failed: HTTP {code}")
+        case _:
+            raise AssertionError(f"{operation} failed: {result.kind}")
+
+
+def cleanup_file(client: BatchCleanupClient, file_id: str, *, key: str, provider: str | None = None) -> None:
+    result: Final = cleanup_result(lambda: client.delete_file(file_id, key=key, provider=provider))
+    if isinstance(result, UnknownApiError) and result.status_code == 404:
+        return
+    deleted: Final = _require_cleanup_success(result, f"Delete file {file_id}")
+    assert deleted.deleted is True or (
+        deleted.deleted is None and is_managed_id(file_id) and deleted.id == file_id and deleted.object == "file"
+    ), f"Delete file {file_id} did not confirm deletion"
+
+
+def cleanup_batch(
+    client: BatchCleanupClient,
+    batch_id: str,
+    *,
+    key: str,
+    provider: str | None = None,
+    delete_output_files: bool = False,
+    wait: Callable[[float], None] = sleep,
+    clock: Callable[[], float] = monotonic,
+) -> None:
+    needs_terminal_state: Final = is_managed_id(batch_id)
+    fetched: Final = _require_cleanup_success(
+        cleanup_result(lambda: client.retrieve_batch(batch_id, key=key, provider=provider)),
+        f"Retrieve batch {batch_id} for cleanup",
+    )
+    if fetched.status in BATCH_TERMINAL_STATUSES:
+        if delete_output_files:
+            _cleanup_batch_outputs(client, fetched, key=key, provider=provider)
+        return
+    if fetched.status == "cancelling" and not needs_terminal_state:
+        return
+    result: Final = (
+        Success(status_code=200, data=fetched)
+        if fetched.status == "cancelling"
+        else cleanup_result(lambda: client.cancel_batch(batch_id, key=key, provider=provider))
+    )
+    conflicted: Final = isinstance(result, UnknownApiError) and result.status_code in {400, 409}
+    if not conflicted:
+        cancelled: Final = _require_cleanup_success(result, f"Cancel batch {batch_id}")
+        assert cancelled.status in BATCH_TERMINAL_STATUSES | BATCH_PENDING_STATUSES, (
+            f"Cancel batch {batch_id} left status {cancelled.status}"
+        )
+        if cancelled.status in BATCH_TERMINAL_STATUSES:
+            if delete_output_files:
+                _cleanup_batch_outputs(client, cancelled, key=key, provider=provider)
+            return
+        if cancelled.status == "cancelling" and not needs_terminal_state:
+            return
+    deadline: Final = clock() + BATCH_CANCEL_TIMEOUT_SECONDS
+    for current in (
+        _require_cleanup_success(
+            cleanup_result(lambda: client.retrieve_batch(batch_id, key=key, provider=provider)),
+            f"Retrieve batch {batch_id} after cancellation",
+        )
+        for _ in count()
+    ):
+        if current.status in BATCH_TERMINAL_STATUSES:
+            if delete_output_files:
+                _cleanup_batch_outputs(client, current, key=key, provider=provider)
+            return
+        assert current.status in ({"cancelling"} if conflicted else BATCH_PENDING_STATUSES), (
+            f"Cancel batch {batch_id} left status {current.status}"
+        )
+        if current.status == "cancelling" and not needs_terminal_state:
+            return
+        assert clock() < deadline, (
+            f"Batch {batch_id} cancellation did not finish within {BATCH_CANCEL_TIMEOUT_SECONDS}s"
+        )
+        wait(BATCH_CANCEL_POLL_SECONDS)
+
+
+def _cleanup_batch_outputs(client: BatchCleanupClient, batch: BatchObject, *, key: str, provider: str | None) -> None:
+    errors: Final = tuple(
+        error
+        for file_id in dict.fromkeys((batch.output_file_id, batch.error_file_id))
+        if file_id is not None and file_id != batch.input_file_id
+        if (error := _output_cleanup_error(client, file_id, key=key, provider=provider)) is not None
+    )
+    if errors:
+        raise ExceptionGroup(f"Batch {batch.id} output cleanup failed", errors)
+
+
+def _output_cleanup_error(
+    client: BatchCleanupClient, file_id: str, *, key: str, provider: str | None
+) -> Exception | None:
+    try:
+        cleanup_file(client, file_id, key=key, provider=provider)
+    except Exception as error:
+        return error
+    return None
diff --git a/tests/e2e/batches/batch_client.py b/tests/e2e/batches/batch_client.py
index 31e49f22450..c9c77e1f12e 100644
--- a/tests/e2e/batches/batch_client.py
+++ b/tests/e2e/batches/batch_client.py
@@ -13,8 +13,9 @@ co-located here because only this suite uses them.
 from __future__ import annotations
 
 from dataclasses import dataclass
+from typing import Final, Literal
 
-from pydantic import BaseModel
+from pydantic import BaseModel, Field
 
 from proxy_client import ProxyClient
 from e2e_http import (
@@ -27,6 +28,18 @@ from e2e_http import (
 from models import LiteLLMParamsBody
 
 UPLOAD_FILENAME = "batch_input.jsonl"
+AZURE_FILE_EXPIRY_SECONDS: Final = 14 * 24 * 60 * 60
+
+
+class ExpiringFileUploadForm(FileUploadForm):
+    expires_after_anchor: Literal["created_at"] = Field(default="created_at", alias="expires_after[anchor]")
+    expires_after_seconds: int = Field(default=AZURE_FILE_EXPIRY_SECONDS, alias="expires_after[seconds]")
+
+
+def batch_upload_form(provider: str, *, target_model_names: str | None = None) -> FileUploadForm:
+    if provider == "azure":
+        return ExpiringFileUploadForm(target_model_names=target_model_names)
+    return FileUploadForm(target_model_names=target_model_names)
 
 
 class FileObject(BaseModel):
@@ -37,6 +50,7 @@ class FileObject(BaseModel):
     bytes: int | None = None
     status: str | None = None
     created_at: int | None = None
+    expires_at: int | None = None
 
 
 class FileList(BaseModel):
@@ -85,7 +99,7 @@ class BatchList(BaseModel):
 class FileDeleteResponse(BaseModel):
     id: str
     object: str | None = None
-    deleted: bool
+    deleted: bool | None = None
 
 
 class BatchCreateBody(BaseModel):
diff --git a/tests/e2e/batches/capabilities.py b/tests/e2e/batches/capabilities.py
index 1bcea0a61ee..17749c2fb87 100644
--- a/tests/e2e/batches/capabilities.py
+++ b/tests/e2e/batches/capabilities.py
@@ -108,6 +108,10 @@ class Capability:
     def id(self) -> str:
         return f"{self.provider}-{self.scenario}"
 
+    @property
+    def file_provider(self) -> str | None:
+        return self.provider if self.scenario in {"model_param", "provider_fallback"} else None
+
     @property
     def jsonl_model(self) -> str:
         # Always the provider deployment name. Unified routes via
diff --git a/tests/e2e/batches/conftest.py b/tests/e2e/batches/conftest.py
index 3b133fab680..91a365b6b92 100644
--- a/tests/e2e/batches/conftest.py
+++ b/tests/e2e/batches/conftest.py
@@ -13,7 +13,7 @@ the proxy config.
 from __future__ import annotations
 
 import os
-from typing import Iterator
+from typing import Final, Iterator
 
 import pytest
 
@@ -21,6 +21,7 @@ from batch_client import BatchClient, build_client
 from capabilities import PROVIDERS
 from e2e_config import MANAGED_FILES_OPT_IN_ENV
 from e2e_http import NoBody
+from lifecycle import ResourceManager
 from proxy_client import ProxyClient
 
 
@@ -52,6 +53,13 @@ def client(proxy: ProxyClient) -> BatchClient:
     return build_client(proxy)
 
 
+@pytest.fixture
+def resources(client: BatchClient) -> Iterator[ResourceManager]:
+    manager: Final = ResourceManager(client=client.proxy, strict_cleanup=True)
+    yield manager
+    manager.teardown()
+
+
 @pytest.fixture(scope="session")
 def batch_deployments(client: BatchClient) -> Iterator[None]:
     probe = client.proxy.probe("/health/liveliness", params=NoBody())
diff --git a/tests/e2e/batches/test_batch_cleanup.py b/tests/e2e/batches/test_batch_cleanup.py
new file mode 100644
index 00000000000..d0038139dcf
--- /dev/null
+++ b/tests/e2e/batches/test_batch_cleanup.py
@@ -0,0 +1,313 @@
+from builtins import ExceptionGroup
+from collections.abc import Callable
+from typing import Final
+from unittest.mock import Mock, call
+
+import pytest
+from batch_cleanup import BATCH_CANCEL_TIMEOUT_SECONDS, CLEANUP_DELAYS, cleanup_batch, cleanup_file, cleanup_result
+from batch_client import AZURE_FILE_EXPIRY_SECONDS, BatchObject, FileDeleteResponse, batch_upload_form
+from capabilities import CAPABILITIES, Capability
+from e2e_http import NetworkError, RateLimitedError, Result, Success, UnknownApiError
+from lifecycle import ResourceManager
+from models import KeyGenerateBody
+
+MANAGED_FILE_ID: Final = "bGl0ZWxsbV9wcm94eTtmaWxlLTE="
+MANAGED_BATCH_ID: Final = "bGl0ZWxsbV9wcm94eTtiYXRjaC0x"
+
+
+class ExpectedCalls[T]:
+    def __init__(self, values: tuple[T, ...]) -> None:
+        self.values: Final = values
+        self.recorder: Final = Mock()
+
+    def __call__(self, value: T) -> None:
+        self.recorder(value)
+
+    def assert_done(self) -> None:
+        assert tuple(self.recorder.call_args_list) == tuple(call(value) for value in self.values)
+
+
+class CleanupClient:
+    def __init__(
+        self,
+        *,
+        calls: ExpectedCalls[str],
+        files: tuple[Result[FileDeleteResponse], ...] = (),
+        batches: tuple[Result[BatchObject], ...] = (),
+        cancellations: tuple[Result[BatchObject], ...] = (),
+    ) -> None:
+        self.calls: Final = calls
+        self.file_response: Final[Callable[[], Result[FileDeleteResponse]]] = Mock(side_effect=files)
+        self.batch_response: Final[Callable[[], Result[BatchObject]]] = Mock(side_effect=batches)
+        self.cancel_response: Final[Callable[[], Result[BatchObject]]] = Mock(side_effect=cancellations)
+
+    def delete_file(self, file_id: str, *, key: str, provider: str | None = None) -> Result[FileDeleteResponse]:
+        self.calls(f"delete {provider} {file_id}")
+        return self.file_response()
+
+    def retrieve_batch(self, batch_id: str, *, key: str, provider: str | None = None) -> Result[BatchObject]:
+        self.calls(f"retrieve {provider} {batch_id}")
+        return self.batch_response()
+
+    def cancel_batch(self, batch_id: str, *, key: str, provider: str | None = None) -> Result[BatchObject]:
+        self.calls(f"cancel {provider} {batch_id}")
+        return self.cancel_response()
+
+    def generate_key(self, body: KeyGenerateBody) -> str:
+        return "test-key"
+
+    def delete_key(self, key: str) -> None:
+        self.calls(f"delete key {key}")
+
+    def delete_customers(self, user_ids: list[str]) -> None:
+        self.calls(f"delete customers {user_ids}")
+
+
+def batch(status: str) -> Success[BatchObject]:
+    return Success(status_code=200, data=BatchObject(id="batch-1", status=status))
+
+
+def deleted_file(*, deleted: bool = True) -> Success[FileDeleteResponse]:
+    return Success(status_code=200, data=FileDeleteResponse(id="file-1", deleted=deleted))
+
+
+class TestFileCleanup:
+    def test_managed_delete_accepts_the_deleted_file_object(self) -> None:
+        response: Final = Success(
+            status_code=200, data=FileDeleteResponse.model_validate({"id": MANAGED_FILE_ID, "object": "file"})
+        )
+        client: Final = CleanupClient(calls=ExpectedCalls((f"delete None {MANAGED_FILE_ID}",)), files=(response,))
+        cleanup_file(client, MANAGED_FILE_ID, key="test-key")
+        client.calls.assert_done()
+
+    @pytest.mark.parametrize("file_id", ["file-1", MANAGED_FILE_ID])
+    def test_a_success_status_without_a_deletion_confirmation_is_rejected(self, file_id: str) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls((f"delete None {file_id}",)),
+            files=(Success(status_code=200, data=FileDeleteResponse(id=file_id)),),
+        )
+        with pytest.raises(AssertionError, match="did not confirm deletion"):
+            cleanup_file(client, file_id, key="test-key")
+        client.calls.assert_done()
+
+    @pytest.mark.parametrize("cap", CAPABILITIES, ids=[cap.id for cap in CAPABILITIES])
+    def test_deletes_raw_files_through_the_upload_provider(self, cap: Capability) -> None:
+        expected_provider: Final = cap.provider if cap.scenario in {"model_param", "provider_fallback"} else None
+        client: Final = CleanupClient(
+            calls=ExpectedCalls((f"delete {expected_provider} file-1",)), files=(deleted_file(),)
+        )
+        cleanup_file(client, "file-1", key="test-key", provider=cap.file_provider)
+        client.calls.assert_done()
+
+    def test_failed_delete_is_reported_after_remaining_resources_are_cleaned(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("delete azure file-1", "delete key test-key")),
+            files=(UnknownApiError(status_code=403, body="secret response"),),
+        )
+        manager: Final = ResourceManager(client=client, strict_cleanup=True)
+        key: Final = manager.key()
+        manager.defer(lambda: cleanup_file(client, "file-1", key=key, provider="azure"))
+        with pytest.raises(ExceptionGroup) as caught:
+            manager.teardown()
+        client.calls.assert_done()
+        assert len(caught.value.exceptions) == 1
+        assert str(caught.value.exceptions[0]) == "Delete file file-1 failed: HTTP 403"
+
+    def test_success_response_must_confirm_deletion(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("delete None file-1",)), files=(deleted_file(deleted=False),)
+        )
+        with pytest.raises(AssertionError, match="did not confirm deletion"):
+            cleanup_file(client, "file-1", key="test-key")
+        client.calls.assert_done()
+
+    def test_cleanup_is_idempotent_when_file_is_already_deleted(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("delete azure file-1",)),
+            files=(UnknownApiError(status_code=404, body="missing"),),
+        )
+        cleanup_file(client, "file-1", key="test-key", provider="azure")
+        client.calls.assert_done()
+
+    def test_default_resource_cleanup_keeps_existing_best_effort_behavior(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("delete None file-1", "delete key test-key")),
+            files=(UnknownApiError(status_code=403, body="forbidden"),),
+        )
+        manager: Final = ResourceManager(client=client)
+        key: Final = manager.key()
+        manager.defer(lambda: cleanup_file(client, "file-1", key=key))
+        manager.teardown()
+        client.calls.assert_done()
+
+
+class TestCleanupRetries:
+    @pytest.mark.parametrize(
+        "failure",
+        [NetworkError(message="offline"), RateLimitedError(), UnknownApiError(status_code=503, body="unavailable")],
+    )
+    def test_transient_error_retries_and_returns_success(self, failure: Result[FileDeleteResponse]) -> None:
+        responses: Final = (failure, deleted_file())
+        outcomes: Final = Mock(side_effect=responses)
+        delays: Final = ExpectedCalls((1.0,))
+        result: Final[Result[FileDeleteResponse]] = cleanup_result(outcomes, wait=delays)
+        assert isinstance(result, Success) and result.data.deleted
+        delays.assert_done()
+
+    def test_persistent_error_has_bounded_retries(self) -> None:
+        failure: Final = UnknownApiError(status_code=503, body="unavailable")
+        outcomes: Final = Mock(return_value=failure)
+        delays: Final = ExpectedCalls(CLEANUP_DELAYS)
+        result: Final[Result[FileDeleteResponse]] = cleanup_result(outcomes, wait=delays)
+        assert result is failure
+        delays.assert_done()
+        assert outcomes.call_count == len(CLEANUP_DELAYS) + 1
+
+    def test_permanent_error_is_not_retried(self) -> None:
+        failure: Final = UnknownApiError(status_code=403, body="forbidden")
+        responses: Final = (failure, deleted_file())
+        outcomes: Final = Mock(side_effect=responses)
+        delays: Final = ExpectedCalls[float](())
+        assert cleanup_result(outcomes, wait=delays) is failure
+        delays.assert_done()
+        assert outcomes.call_count == 1
+
+
+class TestBatchCancellation:
+    def test_cancelling_batch_is_polled_until_terminal_without_cancelling_again(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls((f"retrieve None {MANAGED_BATCH_ID}",) * 3),
+            batches=(batch("cancelling"), batch("cancelling"), batch("cancelled")),
+        )
+        delays: Final = ExpectedCalls((10.0,))
+        cleanup_batch(client, MANAGED_BATCH_ID, key="test-key", wait=delays)
+        client.calls.assert_done()
+        delays.assert_done()
+
+    def test_cancellation_timeout_is_reported_but_file_and_key_cleanup_still_run(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(
+                (
+                    f"retrieve None {MANAGED_BATCH_ID}",
+                    f"retrieve None {MANAGED_BATCH_ID}",
+                    "delete None file-1",
+                    "delete key test-key",
+                )
+            ),
+            batches=(batch("cancelling"), batch("cancelling")),
+            files=(deleted_file(),),
+        )
+        times: Final = (0.0, BATCH_CANCEL_TIMEOUT_SECONDS)
+        ticks: Final[Callable[[], float]] = Mock(side_effect=times)
+        manager: Final = ResourceManager(client=client, strict_cleanup=True)
+        key: Final = manager.key()
+        manager.defer(lambda: cleanup_file(client, "file-1", key=key))
+        manager.defer(lambda: cleanup_batch(client, MANAGED_BATCH_ID, key=key, clock=ticks))
+        with pytest.raises(ExceptionGroup) as caught:
+            manager.teardown()
+        assert "cancellation did not finish" in str(caught.value.exceptions[0])
+        client.calls.assert_done()
+
+    @pytest.mark.parametrize("status", ["completed", "failed", "expired", "cancelled"])
+    def test_inactive_batch_needs_no_cancellation(self, status: str) -> None:
+        client: Final = CleanupClient(calls=ExpectedCalls(("retrieve None batch-1",)), batches=(batch(status),))
+        cleanup_batch(client, "batch-1", key="test-key")
+        client.calls.assert_done()
+
+    def test_active_batch_is_cancelled_through_its_provider(self) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("retrieve azure batch-1", "cancel azure batch-1")),
+            batches=(batch("in_progress"), batch("cancelled")),
+            cancellations=(batch("cancelling"),),
+        )
+        cleanup_batch(client, "batch-1", key="test-key", provider="azure")
+        client.calls.assert_done()
+
+    @pytest.mark.parametrize("batch_id", ["batch-1", MANAGED_BATCH_ID])
+    @pytest.mark.parametrize("pending_status", ["validating", "in_progress"])
+    def test_accepted_cancellation_waits_through_stale_provider_status(
+        self, batch_id: str, pending_status: str
+    ) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(
+                (
+                    f"retrieve vertex_ai {batch_id}",
+                    f"cancel vertex_ai {batch_id}",
+                    f"retrieve vertex_ai {batch_id}",
+                    f"retrieve vertex_ai {batch_id}",
+                    f"retrieve vertex_ai {batch_id}",
+                    "delete vertex_ai file-1",
+                    "delete key test-key",
+                )
+            ),
+            batches=(batch("validating"), batch(pending_status), batch(pending_status), batch("cancelled")),
+            cancellations=(batch(pending_status),),
+            files=(deleted_file(),),
+        )
+        delays: Final = ExpectedCalls((10.0, 10.0))
+        manager: Final = ResourceManager(client=client, strict_cleanup=True)
+        key: Final = manager.key()
+        manager.defer(lambda: cleanup_file(client, "file-1", key=key, provider="vertex_ai"))
+        manager.defer(lambda: cleanup_batch(client, batch_id, key=key, provider="vertex_ai", wait=delays))
+        manager.teardown()
+        client.calls.assert_done()
+        delays.assert_done()
+
+    @pytest.mark.parametrize("output_delete_fails", [False, True])
+    def test_batch_that_completed_before_cleanup_deletes_output_and_error_files(
+        self, output_delete_fails: bool
+    ) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("retrieve openai batch-1", "delete openai file-output", "delete openai file-error")),
+            batches=(
+                Success(
+                    status_code=200,
+                    data=BatchObject(
+                        id="batch-1",
+                        status="completed",
+                        input_file_id="file-input",
+                        output_file_id="file-output",
+                        error_file_id="file-error",
+                    ),
+                ),
+            ),
+            files=(
+                UnknownApiError(status_code=403, body="forbidden") if output_delete_fails else deleted_file(),
+                deleted_file(),
+            ),
+        )
+        if output_delete_fails:
+            with pytest.raises(ExceptionGroup, match="output cleanup failed"):
+                cleanup_batch(client, "batch-1", key="test-key", provider="openai", delete_output_files=True)
+        else:
+            cleanup_batch(client, "batch-1", key="test-key", provider="openai", delete_output_files=True)
+        client.calls.assert_done()
+
+    @pytest.mark.parametrize("status", ["completed", "in_progress"])
+    def test_cancellation_conflict_is_accepted_only_when_batch_became_inactive(self, status: str) -> None:
+        client: Final = CleanupClient(
+            calls=ExpectedCalls(("retrieve None batch-1", "cancel None batch-1", "retrieve None batch-1")),
+            batches=(batch("in_progress"), batch(status)),
+            cancellations=(UnknownApiError(status_code=409, body="conflict"),),
+        )
+        if status == "completed":
+            cleanup_batch(client, "batch-1", key="test-key")
+        else:
+            with pytest.raises(AssertionError, match="Cancel batch batch-1 left status in_progress"):
+                cleanup_batch(client, "batch-1", key="test-key")
+        client.calls.assert_done()
+
+
+class TestAzureFileExpiry:
+    def test_azure_form_serializes_native_expiry_for_the_proxy(self) -> None:
+        form: Final = batch_upload_form("azure", target_model_names="azure-test")
+        assert form.model_dump(by_alias=True, exclude_none=True) == {
+            "purpose": "batch",
+            "target_model_names": "azure-test",
+            "expires_after[anchor]": "created_at",
+            "expires_after[seconds]": AZURE_FILE_EXPIRY_SECONDS,
+        }
+
+    @pytest.mark.parametrize("provider", ["openai", "vertex_ai", "bedrock"])
+    def test_other_providers_keep_their_existing_upload_fields(self, provider: str) -> None:
+        assert batch_upload_form(provider).model_dump(by_alias=True, exclude_none=True) == {"purpose": "batch"}
diff --git a/tests/e2e/batches/test_batches_e2e.py b/tests/e2e/batches/test_batches_e2e.py
index ed7cf656d01..c4b699190b8 100644
--- a/tests/e2e/batches/test_batches_e2e.py
+++ b/tests/e2e/batches/test_batches_e2e.py
@@ -21,14 +21,16 @@ import os
 import re
 import time
 from datetime import datetime, timedelta, timezone
-from typing import Callable
 
 import pytest
 from pydantic import BaseModel
 
-from e2e_config import PROXY_BASE_URL, unique_marker
+from e2e_config import MASTER_KEY, PROXY_BASE_URL, unique_marker
 
+from batch_cleanup import cleanup_batch, cleanup_file
 from batch_client import (
+    AZURE_FILE_EXPIRY_SECONDS,
+    batch_upload_form,
     UPLOAD_FILENAME,
     BatchClient,
     BatchCreateBody,
@@ -155,19 +157,19 @@ def upload_for_scenario(
     if cap.scenario == "encoded":
         return client.upload_file(
             content=content,
-            form=FileUploadForm(purpose="batch"),
+            form=batch_upload_form(cap.provider),
             model=cap.model,
             key=key,
         )
     if cap.scenario == "unified":
         return client.upload_file(
             content=content,
-            form=FileUploadForm(purpose="batch", target_model_names=cap.model),
+            form=batch_upload_form(cap.provider, target_model_names=cap.model),
             key=key,
         )
     return client.upload_file(
         content=content,
-        form=FileUploadForm(purpose="batch"),
+        form=batch_upload_form(cap.provider),
         key=key,
         provider=cap.provider,
     )
@@ -188,20 +190,11 @@ def create_for_scenario(
 
 
 def op_provider(cap: Capability) -> str | None:
-    """provider_fallback ids are raw, so retrieve/cancel/list/delete need the provider
+    """provider_fallback batch ids are raw, so retrieve/cancel/list need the provider
     hint; the other scenarios encode it into the id and route automatically."""
     return cap.provider if cap.scenario == "provider_fallback" else None
 
 
-def quietly(action: Callable[[], object]) -> Callable[[], None]:
-    """Adapt a value-returning call into a best-effort cleanup the teardown can run."""
-
-    def run() -> None:
-        action()
-
-    return run
-
-
 def assert_file_object(file: FileObject, *, provider: str) -> None:
     assert file.object == "file", f"file.object={file.object!r}"
     assert file.purpose == "batch", f"file.purpose={file.purpose!r}"
@@ -209,6 +202,10 @@ def assert_file_object(file: FileObject, *, provider: str) -> None:
     if provider != "bedrock":
         assert file.bytes > 0, f"file.bytes={file.bytes!r}"
     assert file.status, "file.status missing"
+    if provider == "azure":
+        assert file.expires_at is not None, "Azure batch input has no automatic expiry"
+        assert file.created_at is not None
+        assert file.expires_at - file.created_at == AZURE_FILE_EXPIRY_SECONDS
     assert (
         file.created_at is not None and file.created_at > 0
     ), "file.created_at missing"
@@ -249,7 +246,7 @@ def test_batch_lifecycle(
 
     file = unwrap(upload_for_scenario(client, cap, render_jsonl(cap.jsonl_model), key))
     resources.defer(
-        quietly(lambda: client.delete_file(file.id, key=key, provider=provider))
+        lambda: cleanup_file(client, file.id, key=key, provider=cap.file_provider)
     )
     assert_file_object(file, provider=cap.provider)
     assert matches_id_shape(
@@ -260,7 +257,9 @@ def test_batch_lifecycle(
     require_successful_call(created)
     batch = BatchObject.model_validate_json(created.body)
     resources.defer(
-        quietly(lambda: client.cancel_batch(batch.id, key=key, provider=provider))
+        lambda: cleanup_batch(
+            client, batch.id, key=key, provider=provider, delete_output_files=cap.provider in {"openai", "azure"}
+        )
     )
 
     assert batch.id, f"create returned no batch id (body={created.body[:200]})"
@@ -339,7 +338,7 @@ def test_batch_key_model_access_denied(
 
     denied_upload = client.upload_file(
         content=render_jsonl(AZURE_BATCH_MODEL),
-        form=FileUploadForm(purpose="batch"),
+        form=batch_upload_form("azure"),
         model=AZURE_BATCH_MODEL,
         key=key,
     )
@@ -356,7 +355,7 @@ def test_batch_key_model_access_denied(
         )
     ).id
     resources.defer(
-        quietly(lambda: client.delete_file(raw_file, key=key, provider="openai"))
+        lambda: cleanup_file(client, raw_file, key=key, provider="openai")
     )
 
     denied_create = client.create_batch(
@@ -383,6 +382,7 @@ def test_file_upload_and_delete_outputs(
             key=key,
         )
     )
+    resources.defer(lambda: cleanup_file(client, file.id, key=key))
     assert_file_object(file, provider="openai")
 
     deleted = unwrap(client.delete_file(file.id, key=key))
@@ -458,12 +458,12 @@ def test_rate_limited_batch_create_leaves_no_unattributed_spend_row(
             key=key,
         )
     )
-    resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+    resources.defer(lambda: cleanup_file(client, file.id, key=key))
 
     created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
     require_successful_call(created)
     batch = BatchObject.model_validate_json(created.body)
-    resources.defer(quietly(lambda: client.cancel_batch(batch.id, key=key)))
+    resources.defer(lambda: cleanup_batch(client, batch.id, key=key))
 
     _ = client.proxy.poll_logs_for_key(key, min_rows=1)
 
@@ -517,7 +517,7 @@ class TestBatchFileContent:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert file.id
 
         downloaded = client.proxy.transport.download(
@@ -559,11 +559,11 @@ class TestBatchFileContent:
         file = unwrap(
             client.upload_file(
                 content=payload,
-                form=FileUploadForm(purpose="batch", target_model_names=provider.model),
+                form=batch_upload_form(provider.name, target_model_names=provider.model),
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert_file_object(file, provider=provider.name)
         assert is_managed_id(file.id), (
             f"{provider.name}: unified upload must return a managed file id, got {file.id!r}"
@@ -626,7 +626,7 @@ class TestOpenAIFiles:
             )
         )
         resources.defer(
-            quietly(lambda: client.delete_file(file.id, key=key, provider="openai"))
+            lambda: cleanup_file(client, file.id, key=key, provider="openai")
         )
 
         listed = unwrap(client.list_files(key=key))
@@ -690,7 +690,7 @@ class TestOpenAIFiles:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
 
         fetched = unwrap(client.retrieve_file(file.id, key=key))
         assert fetched.id == file.id, "retrieve must echo the uploaded file id"
@@ -760,7 +760,7 @@ class TestBatchRateLimitErrorMapping:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
 
         created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
 
@@ -803,7 +803,7 @@ class TestBatchEnqueuedTokenLimit:
     """
 
     def _upload_batch_file(
-        self, client: BatchClient, resources: ResourceManager, key: str
+        self, client: BatchClient, resources: ResourceManager, key: str, *, cleanup_key: str | None = None
     ) -> FileObject:
         file = unwrap(
             client.upload_file(
@@ -813,7 +813,7 @@ class TestBatchEnqueuedTokenLimit:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=cleanup_key or key))
         return file
 
     def _generate_enqueued_key(
@@ -850,7 +850,7 @@ class TestBatchEnqueuedTokenLimit:
             marker="rpm",
             rpm_limit=BATCH_RL_RPM_LIMIT,
         )
-        file = self._upload_batch_file(client, resources, key)
+        file = self._upload_batch_file(client, resources, key, cleanup_key=MASTER_KEY)
 
         created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
 
@@ -861,7 +861,7 @@ class TestBatchEnqueuedTokenLimit:
         )
         require_successful_call(created)
         batch = BatchObject.model_validate_json(created.body)
-        resources.defer(quietly(lambda: client.cancel_batch(batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, batch.id, key=MASTER_KEY, delete_output_files=True))
 
     @pytest.mark.covers(
         "quota_management.ratelimit.batch_enqueued_tokens.blocks_when_exhausted",
@@ -904,7 +904,7 @@ class TestBatchEnqueuedTokenLimit:
         first = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
         require_successful_call(first)
         first_batch = BatchObject.model_validate_json(first.body)
-        resources.defer(quietly(lambda: client.cancel_batch(first_batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, first_batch.id, key=key))
 
         blocked = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
         assert blocked.status_code == 429, (
@@ -928,7 +928,7 @@ class TestBatchEnqueuedTokenLimit:
         )
         require_successful_call(retried)
         retry_batch = BatchObject.model_validate_json(retried.body)
-        resources.defer(quietly(lambda: client.cancel_batch(retry_batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, retry_batch.id, key=key))
 
 
 ASSUME_ROLE_RAW_MODEL = "bedrock/us.anthropic.claude-haiku-4-5-20251001-v1:0"
@@ -984,13 +984,13 @@ class TestBedrockBatchAssumeRole:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert_file_object(file, provider="bedrock")
 
         created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
         require_successful_call(created)
         batch = BatchObject.model_validate_json(created.body)
-        resources.defer(quietly(lambda: client.cancel_batch(batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, batch.id, key=key))
 
         assert batch.id, f"assume-role create returned no batch id: {created.body[:200]}"
         assert is_managed_id(batch.id), (
@@ -1044,7 +1044,7 @@ class TestGeminiFiles:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert_file_object(file, provider="gemini")
         assert file.id, "gemini file upload returned no id"
 
@@ -1099,13 +1099,13 @@ class TestHostedVllmBatch:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert_file_object(file, provider="hosted_vllm")
 
         created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
         require_successful_call(created)
         batch = BatchObject.model_validate_json(created.body)
-        resources.defer(quietly(lambda: client.cancel_batch(batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, batch.id, key=key))
 
         assert batch.id, f"hosted_vllm create returned no batch id: {created.body[:200]}"
         assert batch.status in CREATED_BATCH_STATUSES, (
@@ -1192,7 +1192,7 @@ class TestBatchFailurePaths:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
 
         created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
         require_successful_call(created)
@@ -1243,12 +1243,12 @@ class TestBatchFailurePaths:
         file = unwrap(
             client.upload_file(
                 content=render_jsonl(AZURE_BATCH_RAW_MODEL),
-                form=FileUploadForm(purpose="batch"),
+                form=batch_upload_form("azure"),
                 model=AZURE_BATCH_MODEL,
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert decoded_model_from_id(file.id) == AZURE_BATCH_MODEL, (
             f"upload did not encode the azure deployment into the file id: {file.id!r}"
         )
@@ -1258,7 +1258,7 @@ class TestBatchFailurePaths:
         )
         require_successful_call(created)
         batch = BatchObject.model_validate_json(created.body)
-        resources.defer(quietly(lambda: client.cancel_batch(batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, batch.id, key=key))
 
         assert decoded_model_from_id(batch.id) == AZURE_BATCH_MODEL, (
             "create with a foreign encoded file id must route by the file's embedded model, "
@@ -1307,7 +1307,7 @@ class TestBatchSecondHop:
                 key=key,
             )
         )
-        resources.defer(quietly(lambda: client.delete_file(file.id, key=key)))
+        resources.defer(lambda: cleanup_file(client, file.id, key=key))
         assert is_managed_id(file.id), (
             f"second-hop unified upload must return a managed file id, got {file.id!r}"
         )
@@ -1315,7 +1315,7 @@ class TestBatchSecondHop:
         created = client.create_batch(body=BatchCreateBody(input_file_id=file.id), key=key)
         require_successful_call(created)
         batch = BatchObject.model_validate_json(created.body)
-        resources.defer(quietly(lambda: client.cancel_batch(batch.id, key=key)))
+        resources.defer(lambda: cleanup_batch(client, batch.id, key=key))
 
         assert is_managed_id(batch.id), (
             f"second-hop create must return a managed batch id, got {batch.id!r}"
diff --git a/tests/e2e/batches/test_managed_files_enforcement_e2e.py b/tests/e2e/batches/test_managed_files_enforcement_e2e.py
index 7ad0b16adc3..4f703cf0fdc 100644
--- a/tests/e2e/batches/test_managed_files_enforcement_e2e.py
+++ b/tests/e2e/batches/test_managed_files_enforcement_e2e.py
@@ -21,6 +21,7 @@ from typing import Iterator
 import pytest
 
 from batch_client import BatchClient, FileObject
+from batch_cleanup import cleanup_file
 from capabilities import batch_model_name, is_managed_id, openai_batch_params
 from e2e_config import unique_marker
 from e2e_http import FileUploadForm, Result, UnknownApiError, unwrap
@@ -108,7 +109,7 @@ def test_cross_user_managed_id_denied_owner_allowed(
             key=owner_key,
         )
     )
-    resources.defer(lambda: client.delete_file(uploaded.id, key=owner_key))
+    resources.defer(lambda: cleanup_file(client, uploaded.id, key=owner_key))
     assert is_managed_id(uploaded.id), f"expected a managed unified file id, got {uploaded.id}"
 
     denied = client.retrieve_file(uploaded.id, key=other_key)
diff --git a/tests/e2e/coverage_registry/mcp.yaml b/tests/e2e/coverage_registry/mcp.yaml
index ab644118a47..f853e9ff8d6 100644
--- a/tests/e2e/coverage_registry/mcp.yaml
+++ b/tests/e2e/coverage_registry/mcp.yaml
@@ -119,3 +119,11 @@
   assertions: [succeeds]
   source: "server.py:1089"
   rationale: Smoke; rarely used; same auth model as tools
+- id: mcp.list_tools.api_key.toolset_scoped
+  module: mcp
+  tier: P0
+  operation: list_tools
+  auth_family: api_key
+  assertions: [toolset_scoped]
+  source: "user_api_key_auth_mcp.py:2137"
+  rationale: "A key granted a toolset lists exactly the toolset's tools: the rest of the server's catalog stays hidden and every stored name resolves"
diff --git a/tests/e2e/coverage_registry/mgmt.yaml b/tests/e2e/coverage_registry/mgmt.yaml
index 860d96a50b4..c8d7037d2fd 100644
--- a/tests/e2e/coverage_registry/mgmt.yaml
+++ b/tests/e2e/coverage_registry/mgmt.yaml
@@ -76,3 +76,13 @@
 - {id: mgmt.credential_migration.check.happy_path, module: mgmt, tier: P2, surface: api, assertions: [happy_path], source: "key_management_endpoints.py:4252", rationale: "Encryption migration (smoke)"}
 - {id: mgmt.credential.new.serves_request, module: mgmt, tier: P1, surface: api, assertions: [serves_request], source: "credential_endpoints/endpoints.py:42", rationale: "Stored credential resolves into a deployment and serves a live /messages request"}
 - {id: mgmt.model.test_connection.happy_path, module: mgmt, tier: P0, surface: api, assertions: [happy_path], source: "_health_endpoints.py:1785", rationale: "Test Connection for a responses-mode Bedrock Mantle deployment reaches the live provider and reports success; this exact shape 500ed on an acompletion partial before v1.91.0", fail_before_fix: proven}
+- {id: mgmt.mcp_server.new.persists, module: mgmt, tier: P0, surface: api, assertions: [persists], source: "mcp_management_endpoints.py:1577", rationale: "Every field of an admin-created MCP server reads back verbatim, by id and in the list, on every replica"}
+- {id: mgmt.mcp_server.list.persists, module: mgmt, tier: P1, surface: api, assertions: [persists], source: "mcp_management_endpoints.py:1112", rationale: "The MCP page grid lists a created server with the same field values its detail view reports"}
+- {id: mgmt.mcp_server.update.preserves_unrelated_fields, module: mgmt, tier: P0, surface: api, assertions: [preserves_unrelated_fields], source: "mcp_management_endpoints.py:2665", rationale: "A dashboard edit of one field leaves the others intact and is visible on every replica after one save; edits that took several saves to stick were a customer defect"}
+- {id: mgmt.mcp_server.update.clear_persists, module: mgmt, tier: P0, surface: api, assertions: [clear_persists], source: "mcp_management_endpoints.py:2665", rationale: "An explicit null clears the stored field (absent keeps, null clears)"}
+- {id: mgmt.mcp_server.delete.persists, module: mgmt, tier: P0, surface: api, assertions: [persists], source: "mcp_management_endpoints.py:2139", rationale: "A deleted server is gone by id and from the list on every replica"}
+- {id: mgmt.mcp_toolset.new.persists, module: mgmt, tier: P0, surface: api, assertions: [persists], source: "mcp_management_endpoints.py:3009", rationale: "Toolset tools read back under the exact server_id and tool_name written; a toolset stored under one name and read under another granted nothing"}
+- {id: mgmt.mcp_toolset.update.preserves_unrelated_fields, module: mgmt, tier: P0, surface: api, assertions: [preserves_unrelated_fields], source: "mcp_management_endpoints.py:3098", rationale: "Editing the description leaves the tools and name intact"}
+- {id: mgmt.mcp_toolset.update.persists, module: mgmt, tier: P0, surface: api, assertions: [persists], source: "mcp_management_endpoints.py:3098", rationale: "Narrowing the tools to one entry reads back exactly that entry"}
+- {id: mgmt.mcp_toolset.update.clear_persists, module: mgmt, tier: P0, surface: api, assertions: [clear_persists], source: "mcp_management_endpoints.py:3098", fail_before_fix: proven, rationale: "An explicit null clears the stored description; the update used to drop null and keep the old value"}
+- {id: mgmt.mcp_toolset.delete.persists, module: mgmt, tier: P0, surface: api, assertions: [persists], source: "mcp_management_endpoints.py:3149", rationale: "A deleted toolset is gone by id and from the list on every replica"}
diff --git a/tests/e2e/coverage_registry/quota_management.yaml b/tests/e2e/coverage_registry/quota_management.yaml
index d0afcaca848..ad0914d455b 100644
--- a/tests/e2e/coverage_registry/quota_management.yaml
+++ b/tests/e2e/coverage_registry/quota_management.yaml
@@ -58,3 +58,8 @@
 - {id: quota_management.spend_tracking.service_tier.bills_tier_rates, module: quota_management, tier: P1, behavior: spend_tracking, variant: service_tier, assertions: [bills_tier_rates], exercised_on: [chat_completions], source: "cost_calculator.py", rationale: "A priority service_tier call bills input, output, and reasoning at the deployment's *_priority rates and records the tier on the row (#35923, #35925)"}
 - {id: quota_management.spend_tracking.cost_headers.additive_components, module: quota_management, tier: P1, behavior: spend_tracking, variant: cost_headers, assertions: [additive_components], exercised_on: [chat_completions], source: "proxy/common_request_processing.py", rationale: "The x-litellm-response-cost-* component headers sum to the total, input covers only fresh tokens, and reasoning stays a subset of output (#36965)"}
 - {id: quota_management.spend_tracking.passthrough_stream.injects_usage_cost, module: quota_management, tier: P1, behavior: spend_tracking, variant: passthrough_stream, assertions: [injects_usage_cost], exercised_on: [openai_passthrough], source: "proxy/pass_through_endpoints/streaming_handler.py", rationale: "With include_cost_in_streaming_usage on, the /openai passthrough's final streaming usage frame carries the proxy-computed cost (#36503). Uncovered: the flag is only settable in litellm_settings, and the shared e2e stack does not turn it on yet"}
+- {id: quota_management.spend_tracking.key_attribution.joins_key, module: quota_management, tier: P1, behavior: spend_tracking, variant: key_attribution, assertions: [joins_key], exercised_on: [chat_completions, messages, responses, embeddings, batches, files, google_native, rust_control_plane], source: "proxy/spend_tracking/spend_tracking_utils.py", rationale: "Every spend row a virtual key writes across chat, queued chat, messages, responses, embeddings, the Gemini passthrough, file upload, batch create, and a replayed callback log carries api_key equal to the key's token hash and the key alias, the join the usage APIs depend on; a re-hashed token shows up as an unattributed key-hash-* row (#39568, #39572)"}
+- {id: quota_management.spend_tracking.key_attribution.reports_alias_and_email, module: quota_management, tier: P1, behavior: spend_tracking, variant: key_attribution, assertions: [reports_alias_and_email], exercised_on: [chat_completions, messages, responses, embeddings, batches, files, google_native, rust_control_plane], source: "proxy/management_endpoints/internal_user_endpoints.py", rationale: "/spend/logs?api_key= returns every one of the key's rows with its alias and /user/daily/activity aggregates them under the key's token with key_alias and user_email; /spend/logs carries no email field, so the email is asserted on daily activity only"}
+- {id: quota_management.spend_tracking.key_attribution.health_rows_keep_service_account, module: quota_management, tier: P1, behavior: spend_tracking, variant: key_attribution, assertions: [health_rows_keep_service_account], exercised_on: [chat_completions], source: "proxy/health_check.py", rationale: "A /health probe's spend row stays keyed by the literal litellm-internal-health-check service account rather than a hash of it, so health spend never appears as an unattributed key"}
+- {id: quota_management.spend_tracking.key_attribution.retrieve_batch_cost_joins_retrieving_key, module: quota_management, tier: P1, behavior: spend_tracking, variant: key_attribution, assertions: [retrieve_batch_cost_joins_retrieving_key], exercised_on: [batches], source: "proxy/batches_endpoints/endpoints.py", rationale: "The retrieve that first sees a batch in a terminal state prices it inline and writes its {provider_batch_id}_batch_cost row against the retrieving key, so the batch each run creates is one OpenAI fails at validation within seconds and the test retrieves it by its raw provider id with the same key until it is failed; a raw id is never owned by the CheckBatchCost poller, and the row must carry that key's token hash and alias"}
+- {id: quota_management.spend_tracking.key_attribution.poller_batch_cost_joins_creating_key, module: quota_management, tier: P1, behavior: spend_tracking, variant: key_attribution, assertions: [poller_batch_cost_joins_creating_key], exercised_on: [batches], source: "enterprise/litellm_enterprise/proxy/common_utils/check_batch_cost.py", rationale: "The CheckBatchCost poller bills a completed, positive-cost batch created through a unified id against the key that created it, a different writer from the inline retrieve. No test claims this cell yet: OpenAI's completion window is 24h and both e2e stacks boot a fresh Postgres per build, so a completed batch is out of one run's reach and the managed list never shows an earlier run's batch; the cell stays visible as a gap until a run can hand a completed batch to the poller"}
diff --git a/tests/e2e/e2e_http.py b/tests/e2e/e2e_http.py
index 9d5f1658e91..415c72bbb3c 100644
--- a/tests/e2e/e2e_http.py
+++ b/tests/e2e/e2e_http.py
@@ -49,6 +49,11 @@ class AnthropicHeaders(AuthHeaders):
     anthropic_version: str = Field(default="2023-06-01", alias="anthropic-version")
 
 
+class PartialBody(BaseModel):
+    """A body for a partial-update route (absent = keep, null = clear): a field left
+    unset is omitted from the wire, and a field set to None is sent as JSON null."""
+
+
 class NoBody(BaseModel):
     """Empty body/query for routes that take none."""
 
@@ -252,6 +257,13 @@ def assert_auth_denied(result: StreamingResponse, context: str) -> None:
         f"{context}: expected 401/403, got {result.status_code}: {result.body[:300]}"
     )
 
+
+def wire_body(json: BaseModel) -> dict[str, object]:
+    if isinstance(json, PartialBody):
+        return json.model_dump(by_alias=True, exclude_unset=True)
+    return json.model_dump(by_alias=True, exclude_none=True)
+
+
 def _headers(headers: BaseModel) -> dict[str, str]:
     dumped: dict[str, object] = headers.model_dump(by_alias=True, exclude_none=True)
     return {key: str(value) for key, value in dumped.items()}
@@ -307,9 +319,26 @@ def request_with_retry[T: RetryableResponse](
     return issue()
 
 
-def _classify[R: BaseModel](
-    resp: requests.Response, response_type: type[R]
-) -> Result[R]:
+class ClassifiableResponse(Protocol):
+    """What classifying an outcome reads off a response. requests.Response satisfies
+    it, and so does a fake, so the classification rules are testable on their own."""
+
+    @property
+    def status_code(self) -> int: ...
+
+    @property
+    def ok(self) -> bool: ...
+
+    @property
+    def text(self) -> str: ...
+
+    @property
+    def content(self) -> bytes: ...
+
+    def json(self) -> object: ...
+
+
+def classify[R: BaseModel](resp: ClassifiableResponse, response_type: type[R]) -> Result[R]:
     if resp.status_code == 401:
         return UnauthorizedError(body=resp.text)
     if resp.status_code == 429:
@@ -317,7 +346,8 @@ def _classify[R: BaseModel](
     if not resp.ok:
         return UnknownApiError(status_code=resp.status_code, body=resp.text)
     try:
-        return Success(status_code=resp.status_code, data=response_type.model_validate(resp.json()))
+        payload: Final[object] = resp.json() if resp.content else {}
+        return Success(status_code=resp.status_code, data=response_type.model_validate(payload))
     except Exception as exc:  # noqa: BLE001 - any parse/validation failure is a value
         return ValidationError(message=str(exc))
 
@@ -335,13 +365,13 @@ def post[R: BaseModel](
             lambda: requests.post(
                 str(url),
                 headers=_headers(headers),
-                json=json.model_dump(by_alias=True, exclude_none=True),
+                json=wire_body(json),
                 timeout=timeout,
             )
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def get[R: BaseModel](
@@ -363,7 +393,7 @@ def get[R: BaseModel](
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def get_external[R: BaseModel](
@@ -383,7 +413,7 @@ def get_external[R: BaseModel](
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def delete[R: BaseModel](
@@ -400,14 +430,14 @@ def delete[R: BaseModel](
             lambda: requests.delete(
                 str(url),
                 headers=_headers(headers),
-                json=json.model_dump(by_alias=True, exclude_none=True),
+                json=wire_body(json),
                 params=_params(params),
                 timeout=timeout,
             )
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def patch[R: BaseModel](
@@ -423,13 +453,13 @@ def patch[R: BaseModel](
             lambda: requests.patch(
                 str(url),
                 headers=_headers(headers),
-                json=json.model_dump(by_alias=True, exclude_none=True),
+                json=wire_body(json),
                 timeout=timeout,
             )
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def put[R: BaseModel](
@@ -445,13 +475,13 @@ def put[R: BaseModel](
             lambda: requests.put(
                 str(url),
                 headers=_headers(headers),
-                json=json.model_dump(by_alias=True, exclude_none=True),
+                json=wire_body(json),
                 timeout=timeout,
             )
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def probe(
@@ -555,7 +585,7 @@ def send(
                 str(url),
                 headers=_headers(headers),
                 params=_params(params),
-                json=json.model_dump(by_alias=True, exclude_none=True),
+                json=wire_body(json),
                 stream=stream,
                 timeout=timeout,
             )
@@ -605,7 +635,7 @@ def upload[R: BaseModel](
         )
     except requests.RequestException as exc:
         return NetworkError(message=str(exc))
-    return _classify(resp, response_type)
+    return classify(resp, response_type)
 
 
 def stream_binary(
@@ -623,7 +653,7 @@ def stream_binary(
         resp = requests.post(
             str(url),
             headers=_headers(headers),
-            json=json.model_dump(by_alias=True, exclude_none=True),
+            json=wire_body(json),
             stream=True,
             timeout=timeout,
         )
diff --git a/tests/e2e/guardrails/guardrails_client.py b/tests/e2e/guardrails/guardrails_client.py
index 1f55a0f9a56..ed112a79b9b 100644
--- a/tests/e2e/guardrails/guardrails_client.py
+++ b/tests/e2e/guardrails/guardrails_client.py
@@ -7,7 +7,7 @@ from __future__ import annotations
 import time
 from collections.abc import Callable
 from dataclasses import dataclass
-from typing import Literal
+from typing import Final, Literal
 
 from e2e_config import POLL_INTERVAL, POLL_TIMEOUT, settle_propagation, unique_marker
 from e2e_http import NoBody, Result, StreamingResponse, Success, unwrap
@@ -405,6 +405,29 @@ def build_client(proxy: ProxyClient) -> GuardrailsClient:
     return GuardrailsClient(proxy=proxy)
 
 
+def poll_until_guardrail_applied(
+    call: Callable[[], StreamingResponse],
+    guardrail_name: str,
+    *,
+    timeout: float = POLL_TIMEOUT,
+    interval: float = POLL_INTERVAL,
+    now: Callable[[], float] = time.monotonic,
+    sleep: Callable[[float], None] = time.sleep,
+) -> StreamingResponse:
+    deadline: Final = now() + timeout
+    if not (result := call()).ok:
+        return result
+    while (
+        guardrail_name
+        not in (name.strip() for name in result.headers.get("x-litellm-applied-guardrails", "").split(","))
+        and (remaining := deadline - now()) > 0
+    ):
+        sleep(min(interval, remaining))
+        if now() >= deadline or not (result := call()).ok:
+            break
+    return result
+
+
 def poll_until_blocked[R: BaseModel](call: Callable[[], Result[R]]) -> Result[R]:
     """Retry a call that a guardrail should reject until it is, returning the last result.
 
diff --git a/tests/e2e/guardrails/test_guardrails_client.py b/tests/e2e/guardrails/test_guardrails_client.py
new file mode 100644
index 00000000000..423c2ede599
--- /dev/null
+++ b/tests/e2e/guardrails/test_guardrails_client.py
@@ -0,0 +1,66 @@
+from dataclasses import dataclass
+from itertools import chain, repeat
+from typing import Final
+
+import pytest
+
+from e2e_http import StreamingResponse
+from guardrails_client import poll_until_guardrail_applied
+
+
+@dataclass
+class Clock:
+    elapsed: float = 0.0
+
+    def now(self) -> float:
+        return self.elapsed
+
+    def sleep(self, seconds: float) -> None:
+        self.elapsed += seconds
+
+
+def _response(applied: str, status: int = 200) -> StreamingResponse:
+    return StreamingResponse(status_code=status, body="{}", headers={"x-litellm-applied-guardrails": applied})
+
+
+def test_waits_for_requested_guardrail_after_an_unrelated_global_guardrail() -> None:
+    clock: Final = Clock()
+    expected: Final = _response("global-filter, tool-permission")
+    responses: Final = iter((_response("global-filter"), expected))
+
+    result: Final = poll_until_guardrail_applied(
+        lambda: next(responses), "tool-permission", timeout=5, interval=2, now=clock.now, sleep=clock.sleep
+    )
+
+    assert result is expected
+    assert clock.elapsed == 2
+
+
+@pytest.mark.parametrize("applied", ("", "global-filter", "tool-permission-sibling"))
+def test_missing_exact_guardrail_returns_failure_evidence_at_deadline(applied: str) -> None:
+    clock: Final = Clock()
+    missing: Final = _response(applied)
+    responses: Final = iter((missing, missing, missing))
+
+    result: Final = poll_until_guardrail_applied(
+        lambda: next(responses), "tool-permission", timeout=5, interval=2, now=clock.now, sleep=clock.sleep
+    )
+
+    assert result is missing
+    assert clock.elapsed == 5
+    with pytest.raises(StopIteration):
+        next(responses)
+
+
+@pytest.mark.parametrize("status", (400, 401, 429, 500))
+def test_http_failure_is_not_hidden_by_a_later_success(status: int) -> None:
+    clock: Final = Clock()
+    failed: Final = _response("", status)
+    responses: Final = iter(chain((failed,), repeat(_response("tool-permission"))))
+
+    result: Final = poll_until_guardrail_applied(
+        lambda: next(responses), "tool-permission", timeout=5, interval=2, now=clock.now, sleep=clock.sleep
+    )
+
+    assert result is failed
+    assert clock.elapsed == 0
diff --git a/tests/e2e/guardrails/test_tool_permission_guardrail_e2e.py b/tests/e2e/guardrails/test_tool_permission_guardrail_e2e.py
index 9ef3650625c..8d1047e53c7 100644
--- a/tests/e2e/guardrails/test_tool_permission_guardrail_e2e.py
+++ b/tests/e2e/guardrails/test_tool_permission_guardrail_e2e.py
@@ -30,6 +30,7 @@ from guardrails_client import (
     ToolPermissionParamsBody,
     ToolPermissionRuleBody,
     poll_until_blocked,
+    poll_until_guardrail_applied,
 )
 from lifecycle import ResourceManager
 from models import ChatResponse, ChatTool, ChatToolFunction
@@ -84,8 +85,8 @@ def _register_tool_permission(client: GuardrailsClient, resources: ResourceManag
     resources.defer(lambda: client.delete_guardrail(guardrail_id))
 
 
-def _applied_guardrails(outcome: StreamingResponse) -> str:
-    return outcome.headers.get("x-litellm-applied-guardrails", "")
+def _applied_guardrails(outcome: StreamingResponse) -> tuple[str, ...]:
+    return tuple(name.strip() for name in outcome.headers.get("x-litellm-applied-guardrails", "").split(","))
 
 
 def _tool_call_names(response: ChatResponse) -> tuple[str, ...]:
@@ -144,14 +145,17 @@ class TestToolPermissionPreCall:
         name = f"e2e-toolperm-allow-{unique_marker()}"
         _register_tool_permission(client, resources, name=name)
 
-        outcome = client.chat_raw(
-            scoped_key,
-            MODEL,
-            TOOL_PROMPT,
-            guardrails=[name],
-            max_tokens=128,
-            tools=[ALLOWED_TOOL],
-            tool_choice="required",
+        outcome = poll_until_guardrail_applied(
+            lambda: client.chat_raw(
+                scoped_key,
+                MODEL,
+                TOOL_PROMPT,
+                guardrails=[name],
+                max_tokens=128,
+                tools=[ALLOWED_TOOL],
+                tool_choice="required",
+            ),
+            name,
         )
 
         assert outcome.ok, f"the permitted tool must be served, got {outcome.status_code}: {outcome.body[:400]}"
diff --git a/tests/e2e/lifecycle.py b/tests/e2e/lifecycle.py
index c9a67ebdb8c..eb9704d4dcb 100644
--- a/tests/e2e/lifecycle.py
+++ b/tests/e2e/lifecycle.py
@@ -8,8 +8,9 @@ ResourceManager; the test registers a cleanup for every resource it creates, and
 the fixture's teardown releases them all even when the test body raises.
 """
 
+from builtins import ExceptionGroup
 from dataclasses import dataclass, field
-from typing import Callable, List, Protocol, runtime_checkable
+from typing import Callable, Final, List, Protocol, runtime_checkable
 
 from proxy_client import ProxyClient
 from models import KeyGenerateBody
@@ -52,6 +53,7 @@ class ResourceManager:
     """
 
     client: ResourceClient
+    strict_cleanup: bool = False
     _cleanups: List[Callable[[], object]] = field(
         default_factory=list
     )  # mutable-ok: append-only teardown registry
@@ -82,8 +84,17 @@ class ResourceManager:
         return customer_id
 
     def teardown(self) -> None:
-        for cleanup in reversed(self._cleanups):
-            try:
-                cleanup()
-            except Exception:
-                pass  # best-effort: a failed cleanup must not block the rest
+        failures: Final = tuple(
+            failure for cleanup in reversed(self._cleanups)
+            if (failure := _run_cleanup(cleanup)) is not None
+        )
+        if failures and self.strict_cleanup:
+            raise ExceptionGroup("Resource cleanup failed", failures)
+
+
+def _run_cleanup(cleanup: Callable[[], object]) -> Exception | None:
+    try:
+        cleanup()
+    except Exception as exc:
+        return exc
+    return None
diff --git a/tests/e2e/llm_translation/test_responses_bridge_streaming_e2e.py b/tests/e2e/llm_translation/test_responses_bridge_streaming_e2e.py
index 9a45743a0cd..75817340876 100644
--- a/tests/e2e/llm_translation/test_responses_bridge_streaming_e2e.py
+++ b/tests/e2e/llm_translation/test_responses_bridge_streaming_e2e.py
@@ -16,8 +16,10 @@ into a chat completion chunk. Two customer-visible contracts only hold on that p
 
 from __future__ import annotations
 
+from typing import Final, Literal
+
 import pytest
-from pydantic import BaseModel
+from pydantic import BaseModel, Field
 
 from e2e_config import unique_marker
 from e2e_http import StreamingResponse
@@ -51,7 +53,8 @@ class _BridgeChoice(BaseModel):
 
 class _BridgeChunk(BaseModel):
     id: str
-    choices: list[_BridgeChoice] = []
+    object: Literal["chat.completion.chunk"]
+    choices: list[_BridgeChoice] = Field(default_factory=list)
 
 
 class _WeatherArgs(BaseModel):
@@ -103,16 +106,19 @@ class TestResponsesBridgeChatCompletionsStreaming:
             resources.key(),
             ChatBody(
                 model=bridged_model,
-                messages=[ChatMessage(role="user", content=f"Count from 1 to 5, one number per line. {unique_marker()}")],
+                messages=[
+                    ChatMessage(role="user", content=f"Count from 1 to 5, one number per line. {unique_marker()}")
+                ],
                 max_tokens=64,
                 stream=True,
             ),
         )
 
-        chunks = _bridge_chunks(result)
-        ids = {chunk.id for chunk in chunks}
+        chunks: Final = _bridge_chunks(result)
+        assert len(chunks) > 1, "the shared-id contract needs more than one streamed chunk"
+        ids: Final = frozenset(chunk.id for chunk in chunks)
         assert len(ids) == 1, f"bridged stream used {len(ids)} different chunk ids: {sorted(ids)[:5]}"
-        assert ids.pop().startswith("chatcmpl-"), f"bridged chunk id is not chat-completion shaped: {chunks[0].id}"
+        assert chunks[0].id.strip(), "bridged stream emitted an empty chunk id"
 
     @pytest.mark.covers(
         "llm.chat_completions.openai.basic.stream.bridge_streams_sse",
@@ -134,9 +140,9 @@ class TestResponsesBridgeChatCompletionsStreaming:
         chunks = _bridge_chunks(result)
         content = "".join(choice.delta.content or "" for chunk in chunks for choice in chunk.choices)
         assert content.strip(), f"bridged stream completed with no content deltas: {result.stream_events[:3]}"
-        assert any(
-            choice.finish_reason for chunk in chunks for choice in chunk.choices
-        ), f"bridged stream never emitted a finish_reason: {result.stream_events[-3:]}"
+        assert any(choice.finish_reason for chunk in chunks for choice in chunk.choices), (
+            f"bridged stream never emitted a finish_reason: {result.stream_events[-3:]}"
+        )
         assert result.stream_done, f"bridged stream did not terminate with [DONE]: {result.stream_events[-2:]}"
 
     @pytest.mark.covers(
diff --git a/tests/e2e/logging/datadog_reader.py b/tests/e2e/logging/datadog_reader.py
index d0f478185c2..368c20cb6aa 100644
--- a/tests/e2e/logging/datadog_reader.py
+++ b/tests/e2e/logging/datadog_reader.py
@@ -12,8 +12,12 @@ empty result. External reads go through ``e2e_http``.
 
 from __future__ import annotations
 
+import math
+import random
 import time
-from dataclasses import dataclass
+from collections.abc import Callable, Mapping
+from dataclasses import dataclass, field
+from typing import Final
 
 import pytest
 from pydantic import BaseModel, ConfigDict, Field
@@ -27,17 +31,33 @@ from e2e_config import (
     DD_SITE,
     POLL_TIMEOUT,
 )
-from e2e_http import URL, Headers, RateLimitedError, Success, post
+from e2e_http import URL, Headers, StreamingResponse, send
 
-#: How many rate-limited responses in a row one search tolerates before the
-#: hard fail; each retry sleeps a full search interval, so this rides out a
-#: burst from a concurrent consumer of the org-wide search budget.
-_RATE_LIMIT_RETRIES = 5
+type SearchCall = Callable[[str, float], StreamingResponse]
+
+
+def _seconds(value: str | None) -> float | None:
+    if value is None:
+        return None
+    try:
+        seconds: Final = float(value)
+    except ValueError:
+        return None
+    return seconds if math.isfinite(seconds) and seconds >= 0 else None
+
+
+def _rate_limit_delay(headers: Mapping[str, str]) -> float:
+    delays: Final = tuple(
+        delay
+        for name in ("x-ratelimit-reset", "retry-after")
+        if (delay := _seconds(headers.get(name))) is not None
+    )
+    return max(1.0, max(delays, default=DD_SEARCH_INTERVAL))
 
 
 class _DdAuthHeaders(Headers):
-    api_key: str = Field(serialization_alias="DD-API-KEY")
-    app_key: str = Field(serialization_alias="DD-APPLICATION-KEY")
+    api_key: str = Field(serialization_alias="DD-API-KEY", repr=False)
+    app_key: str = Field(serialization_alias="DD-APPLICATION-KEY", repr=False)
 
 
 class _SearchFilter(BaseModel):
@@ -88,8 +108,12 @@ class _SearchResponse(BaseModel):
 @dataclass(frozen=True, slots=True)
 class DdLogsReader:
     site: str
-    api_key: str
-    app_key: str
+    api_key: str = field(repr=False)
+    app_key: str = field(repr=False)
+    search: SearchCall | None = field(default=None, repr=False)
+    now: Callable[[], float] = field(default=time.monotonic, repr=False)
+    sleep: Callable[[float], None] = field(default=time.sleep, repr=False)
+    jitter: Callable[[], float] = field(default=random.random, repr=False)
 
     def events_for_marker(self, marker: str) -> list[DdLogEvent]:
         """Every ingested event whose attributes carry the marker. DataDog
@@ -108,25 +132,28 @@ class DdLogsReader:
         a single event. A 429 backs off and retries - the search budget is
         org-wide, so another consumer can empty it under us - while any other
         failure stays a hard fail."""
-        for _ in range(_RATE_LIMIT_RETRIES):
-            result = post(
-                URL(f"https://api.{self.site}/api/v2/logs/events/search"),
-                headers=_DdAuthHeaders(api_key=self.api_key, app_key=self.app_key),
-                json=_SearchRequest(filter=_SearchFilter(query=query)),
-                response_type=_SearchResponse,
-                timeout=30.0,
-            )
-            match result:
-                case Success(data=page):
-                    return [event.attributes for event in page.data]
-                case RateLimitedError(retry_after_seconds=retry_after):
-                    time.sleep(retry_after if retry_after else DD_SEARCH_INTERVAL)
-                case failure:
-                    pytest.fail(f"DataDog Logs Search API at api.{self.site} failed: {failure}")
+        return self._events_for_query(query, self.now() + POLL_TIMEOUT)
+
+    def _events_for_query(self, query: str, deadline: float) -> list[DdLogEvent]:
+        search: Final = self.search or self._search_page
+        while (remaining := deadline - self.now()) > 0:
+            if (result := search(query, min(30.0, remaining))).ok:
+                return [event.attributes for event in _SearchResponse.model_validate_json(result.body).data]
+            if result.status_code != 429:
+                pytest.fail(f"DataDog Logs Search API at api.{self.site} failed with HTTP {result.status_code}")
+            if (delay := min(_rate_limit_delay(result.headers) + self.jitter(), deadline - self.now())) > 0:
+                self.sleep(delay)
         pytest.fail(
-            f"DataDog Logs Search API at api.{self.site} still rate-limited after "
-            f"{_RATE_LIMIT_RETRIES} retries {DD_SEARCH_INTERVAL}s apart - the org-wide "
-            "logs_public_search_api budget (2 requests per 10s) is exhausted by another consumer"
+            f"DataDog Logs Search API at api.{self.site} remained rate-limited for {POLL_TIMEOUT}s; "
+            "the org-wide logs_public_search_api budget is exhausted"
+        )
+
+    def _search_page(self, query: str, timeout: float) -> StreamingResponse:
+        return send(
+            URL(f"https://api.{self.site}/api/v2/logs/events/search"),
+            headers=_DdAuthHeaders(api_key=self.api_key, app_key=self.app_key),
+            json=_SearchRequest(filter=_SearchFilter(query=query)),
+            timeout=timeout,
         )
 
     def poll_events_for_marker(self, marker: str) -> list[DdLogEvent]:
@@ -140,33 +167,42 @@ class DdLogsReader:
         hide from the exactly-one assertion - real-DataDog jitter can surface
         one call's two events tens of seconds apart. Searches pace at
         DD_SEARCH_INTERVAL, not POLL_INTERVAL, to respect the search API's
-        request budget. At the deadline the last result is returned as-is."""
-        deadline = time.monotonic() + POLL_TIMEOUT
-        while time.monotonic() < deadline:
-            events = self.events_for_query(query)
+        request budget. Discovery, quota retries, and duplicate detection share
+        one POLL_TIMEOUT deadline; an incomplete settle window fails closed."""
+        deadline: Final = self.now() + POLL_TIMEOUT
+        while (remaining := deadline - self.now()) > 0:
+            events = self._events_for_query(query, deadline)
             if events:
-                return self._settled_events_for_query(query, events)
-            time.sleep(DD_SEARCH_INTERVAL)
-        return self.events_for_query(query)
+                return self._settled_events_for_query(query, events, deadline)
+            if (remaining := deadline - self.now()) > 0:
+                self.sleep(min(DD_SEARCH_INTERVAL, remaining))
+        return []
 
-    def _settled_events_for_query(self, query: str, events: list[DdLogEvent]) -> list[DdLogEvent]:
+    def _settled_events_for_query(self, query: str, events: list[DdLogEvent], deadline: float) -> list[DdLogEvent]:
         """Re-read at every search interval until the settle window closes; a
         duplicate ends the watch early because more waiting cannot clear it.
 
         Keep the last non-empty result: a transient empty search (index lag)
         must not erase events already confirmed earlier in the settle window.
+        A successful final search must reach the full settle window before the
+        shared read-back deadline; otherwise duplicate detection is incomplete.
         """
-        settle_deadline = time.monotonic() + DD_SETTLE_SECONDS
+        settle_deadline: Final = self.now() + DD_SETTLE_SECONDS
         last_nonempty = events
-        while time.monotonic() < settle_deadline:
-            time.sleep(DD_SEARCH_INTERVAL)
-            latest = self.events_for_query(query)
-            if not latest:
-                continue
+        if len(events) > 1:
+            return events
+        while (remaining := deadline - self.now()) > 0:
+            self.sleep(min(DD_SEARCH_INTERVAL, remaining))
+            if self.now() >= deadline:
+                break
+            latest = self._events_for_query(query, deadline)
             if len(latest) > 1:
                 return latest
-            last_nonempty = latest
-        return last_nonempty
+            if latest:
+                last_nonempty = latest
+            if self.now() >= settle_deadline:
+                return last_nonempty
+        pytest.fail(f"DataDog log delivery could not complete its duplicate-detection window within {POLL_TIMEOUT}s")
 
 
 def build_dd_logs_reader() -> DdLogsReader:
diff --git a/tests/e2e/logging/test_datadog_reader.py b/tests/e2e/logging/test_datadog_reader.py
new file mode 100644
index 00000000000..910a1cefd42
--- /dev/null
+++ b/tests/e2e/logging/test_datadog_reader.py
@@ -0,0 +1,223 @@
+import json
+from collections.abc import Iterator, Sequence
+from dataclasses import dataclass
+from typing import Final
+
+import pytest
+
+from datadog_reader import DdLogsReader
+from datadog_reader import _DdAuthHeaders  # pyright: ignore[reportPrivateUsage]  # verifies private auth-header serialization
+from e2e_config import DD_SEARCH_INTERVAL, POLL_TIMEOUT
+from e2e_http import StreamingResponse
+
+
+def test_failure_diagnostics_hide_credentials_without_changing_auth_headers() -> None:
+    api_key: Final = "test-datadog-api-secret"
+    app_key: Final = "test-datadog-app-secret"
+    reader: Final = DdLogsReader(site="datadoghq.com", api_key=api_key, app_key=app_key)
+    headers: Final = _DdAuthHeaders(api_key=api_key, app_key=app_key)
+
+    for value in (reader, headers):
+        assert api_key not in repr(value)
+        assert app_key not in repr(value)
+
+    assert headers.model_dump(by_alias=True) == {
+        "DD-API-KEY": api_key,
+        "DD-APPLICATION-KEY": app_key,
+    }
+
+
+@dataclass
+class Clock:
+    elapsed: float = 0.0
+
+    def now(self) -> float:
+        return self.elapsed
+
+    def sleep(self, seconds: float) -> None:
+        self.elapsed += seconds
+
+
+@dataclass
+class Search:
+    responses: Iterator[StreamingResponse]
+    calls: tuple[tuple[str, float], ...] = ()
+
+    def __call__(self, query: str, timeout: float) -> StreamingResponse:
+        self.calls += ((query, timeout),)
+        return next(self.responses)
+
+
+def _page(*event_ids: str) -> StreamingResponse:
+    return StreamingResponse(
+        status_code=200,
+        body=json.dumps({"data": [{"attributes": {"attributes": {"id": event_id}}} for event_id in event_ids]}),
+    )
+
+
+def _reader(responses: Sequence[StreamingResponse], clock: Clock) -> tuple[DdLogsReader, Search]:
+    search: Final = Search(iter(responses))
+    return DdLogsReader(
+        site="us5.datadoghq.com",
+        api_key="test-api-secret",
+        app_key="test-app-secret",
+        search=search,
+        now=clock.now,
+        sleep=clock.sleep,
+        jitter=lambda: 0.25,
+    ), search
+
+
+def test_429_honors_server_reset_and_preserves_duplicate_events() -> None:
+    clock: Final = Clock()
+    reader, search = _reader(
+        (StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": "6"}), _page("first", "duplicate")),
+        clock,
+    )
+
+    events: Final = reader.events_for_query("test-marker")
+
+    assert tuple(event.attributes["id"] for event in events) == ("first", "duplicate")
+    assert clock.elapsed == 6.25
+    assert search.calls == (("test-marker", 30.0), ("test-marker", 30.0))
+
+
+@pytest.mark.parametrize("reset", ("", "invalid", "nan", "inf", "-1"))
+def test_invalid_reset_uses_search_interval(reset: str) -> None:
+    clock: Final = Clock()
+    reader, _ = _reader(
+        (StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": reset}), _page()), clock
+    )
+
+    assert reader.events_for_query("test-marker") == []
+    assert clock.elapsed == DD_SEARCH_INTERVAL + 0.25
+
+
+def test_zero_reset_cannot_create_a_busy_retry_loop() -> None:
+    clock: Final = Clock()
+    reader, _ = _reader(
+        (StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": "0"}), _page()), clock
+    )
+
+    assert reader.events_for_query("test-marker") == []
+    assert clock.elapsed == 1.25
+
+
+def test_retry_after_is_not_shortened_by_an_earlier_reset() -> None:
+    clock: Final = Clock()
+    reader, _ = _reader(
+        (StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": "2", "retry-after": "8"}), _page()),
+        clock,
+    )
+
+    assert reader.events_for_query("test-marker") == []
+    assert clock.elapsed == 8.25
+
+
+def test_rate_limit_wait_stops_at_deadline_without_issuing_another_request() -> None:
+    clock: Final = Clock()
+    reader, search = _reader(
+        (StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": str(POLL_TIMEOUT * 10)}),), clock
+    )
+
+    with pytest.raises(pytest.fail.Exception, match="remained rate-limited"):
+        reader.events_for_query("test-marker")
+
+    assert clock.elapsed == POLL_TIMEOUT
+    assert search.calls == (("test-marker", 30.0),)
+
+
+def test_late_retry_cannot_receive_a_fresh_request_timeout() -> None:
+    clock: Final = Clock()
+    reader, search = _reader(
+        (StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": str(POLL_TIMEOUT - 5)}), _page()),
+        clock,
+    )
+
+    assert reader.events_for_query("test-marker") == []
+    assert search.calls == (("test-marker", 30.0), ("test-marker", 4.75))
+
+
+@pytest.mark.parametrize("status", (-1, 401, 403, 500))
+def test_non_quota_failures_are_not_retried_or_treated_as_empty_results(status: int) -> None:
+    clock: Final = Clock()
+    reader, search = _reader((StreamingResponse(status_code=status, body=""), _page()), clock)
+
+    with pytest.raises(pytest.fail.Exception, match=f"failed with HTTP {status}"):
+        reader.events_for_query("test-marker")
+
+    assert search.calls == (("test-marker", 30.0),)
+    assert clock.elapsed == 0
+
+
+def test_polling_quota_retries_share_the_original_deadline() -> None:
+    clock: Final = Clock()
+    reader, search = _reader(
+        (_page(), StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": str(POLL_TIMEOUT)})),
+        clock,
+    )
+
+    with pytest.raises(pytest.fail.Exception, match="remained rate-limited"):
+        reader.poll_events_for_query("test-marker")
+
+    assert clock.elapsed == POLL_TIMEOUT
+    assert len(search.calls) == 2
+
+
+def test_empty_polling_does_not_start_a_final_search_after_its_deadline() -> None:
+    clock: Final = Clock()
+    attempts: Final = int(POLL_TIMEOUT / DD_SEARCH_INTERVAL)
+    reader, search = _reader((_page(),) * attempts, clock)
+
+    assert reader.poll_events_for_query("test-marker") == []
+    assert clock.elapsed == POLL_TIMEOUT
+    assert len(search.calls) == attempts
+
+
+def test_settlement_quota_retries_keep_the_remaining_readback_budget() -> None:
+    clock: Final = Clock()
+    empty_reads: Final = int(POLL_TIMEOUT / DD_SEARCH_INTERVAL) - 2
+    reader, search = _reader(
+        (_page(),) * empty_reads
+        + (_page("first"), StreamingResponse(status_code=429, body="", headers={"x-ratelimit-reset": str(POLL_TIMEOUT)})),
+        clock,
+    )
+
+    with pytest.raises(pytest.fail.Exception, match="remained rate-limited"):
+        reader.poll_events_for_query("test-marker")
+
+    assert clock.elapsed == POLL_TIMEOUT
+    assert search.calls[-1] == ("test-marker", DD_SEARCH_INTERVAL)
+    assert len(search.calls) == empty_reads + 2
+
+
+def test_settlement_detects_a_duplicate_on_the_final_search() -> None:
+    clock: Final = Clock()
+    reader, _ = _reader((_page("first"), _page("first"), _page(), _page("first", "duplicate")), clock)
+
+    events: Final = reader.poll_events_for_query("test-marker")
+
+    assert tuple(event.attributes["id"] for event in events) == ("first", "duplicate")
+    assert clock.elapsed == 30
+
+
+def test_settlement_keeps_confirmed_events_through_empty_searches() -> None:
+    clock: Final = Clock()
+    reader, _ = _reader((_page("first"), _page(), _page(), _page()), clock)
+
+    events: Final = reader.poll_events_for_query("test-marker")
+
+    assert tuple(event.attributes["id"] for event in events) == ("first",)
+    assert clock.elapsed == 30
+
+
+def test_late_delivery_cannot_pass_without_a_complete_settle_window() -> None:
+    clock: Final = Clock()
+    empty_reads: Final = int(POLL_TIMEOUT / DD_SEARCH_INTERVAL) - 2
+    reader, search = _reader((_page(),) * empty_reads + (_page("first"), _page("first")), clock)
+
+    with pytest.raises(pytest.fail.Exception, match="duplicate-detection window"):
+        reader.poll_events_for_query("test-marker")
+
+    assert clock.elapsed == POLL_TIMEOUT
+    assert len(search.calls) == empty_reads + 2
diff --git a/tests/e2e/management/management_client.py b/tests/e2e/management/management_client.py
index 2b897f5f07f..1ef0d89a8f9 100644
--- a/tests/e2e/management/management_client.py
+++ b/tests/e2e/management/management_client.py
@@ -43,6 +43,9 @@ from models import (
     KeyResetSpendBody,
     KeyResetSpendResponse,
     KeyUpdateBody,
+    McpServerCreateBody,
+    McpServerRow,
+    McpServerUpdateBody,
     ModelDeleteBody,
     OrgDeleteBody,
     OrgInfoParams,
@@ -537,6 +540,38 @@ class ManagementClient:
             ).root
         )
 
+    def create_mcp_server(self, body: McpServerCreateBody) -> McpServerRow:
+        return unwrap(
+            self.proxy.transport.post(
+                "/v1/mcp/server",
+                headers=self.proxy.transport.master,
+                json=body,
+                response_type=McpServerRow,
+            )
+        )
+
+    def update_mcp_server(self, body: McpServerUpdateBody) -> McpServerRow:
+        """PUT /v1/mcp/server, the call behind the dashboard's Save Changes: a partial
+        update where a field left unset keeps its stored value and None clears it."""
+        return unwrap(
+            self.proxy.transport.put(
+                "/v1/mcp/server",
+                headers=self.proxy.transport.master,
+                json=body,
+                response_type=McpServerRow,
+            )
+        )
+
+    def delete_mcp_server(self, server_id: str) -> Result[NoBody]:
+        """DELETE /v1/mcp/server/{server_id}. Returns the outcome so the act phase can
+        unwrap it while a deferred teardown can ignore an already-deleted server."""
+        return self.proxy.transport.delete(
+            f"/v1/mcp/server/{server_id}",
+            headers=self.proxy.transport.master,
+            json=NoBody(),
+            response_type=NoBody,
+        )
+
     def chat_status(self, key: str, model: str, content: str) -> StreamingResponse:
         return self.proxy.transport.send(
             "/chat/completions",
diff --git a/tests/e2e/management/test_mcp_lifecycle_e2e.py b/tests/e2e/management/test_mcp_lifecycle_e2e.py
new file mode 100644
index 00000000000..9257d697647
--- /dev/null
+++ b/tests/e2e/management/test_mcp_lifecycle_e2e.py
@@ -0,0 +1,294 @@
+"""Live e2e: the MCP server and toolset management routes' lifecycle contract.
+
+Two customer defects sit on these routes, and each step here is the read-back that
+would have caught one of them: a dashboard edit that took several saves to stick
+because the read landed on a replica the write had not reached, and a toolset whose
+tools were stored under one name and read back under another, so it granted
+nothing. Every read-back therefore polls every replica that serves the route
+(ProxyClient.read_back_everywhere) and asserts the exact values written, and both
+update routes are held to the same partial-update contract: a field left out of the
+payload keeps its stored value, a field sent as null is cleared. The server URL is
+unreachable on purpose; only persistence is under test, never a tool call.
+"""
+
+from __future__ import annotations
+
+from collections.abc import Callable, Mapping
+from typing import Final
+
+import pytest
+from e2e_config import unique_marker
+from e2e_http import unwrap
+from lifecycle import ResourceManager
+from management_client import ManagementClient
+from models import (
+    McpInfo,
+    McpServerCreateBody,
+    McpServerListResponse,
+    McpServerRow,
+    McpServerUpdateBody,
+    ToolsetCreateBody,
+    ToolsetListResponse,
+    ToolsetRow,
+    ToolsetTool,
+    ToolsetUpdateBody,
+)
+
+pytestmark = pytest.mark.e2e
+
+UNREACHABLE_URL: Final = "https://e2e-fake-mcp.test.local/mcp"
+
+
+def _create_server(client: ManagementClient, resources: ResourceManager) -> tuple[McpServerCreateBody, str]:
+    name: Final = f"e2e_mcp_lifecycle_{unique_marker()}"
+    body: Final = McpServerCreateBody(
+        server_name=name,
+        alias=name,
+        url=UNREACHABLE_URL,
+        transport="http",
+        description="e2e lifecycle server",
+        mcp_info=McpInfo(
+            server_name=f"{name} (display)",
+            description="shown on the MCP page",
+            logo_url="https://e2e.test.local/logo.png",
+        ),
+    )
+    server_id: Final = client.create_mcp_server(body).server_id
+    resources.defer(lambda: client.delete_mcp_server(server_id))
+    return body, server_id
+
+
+def _assert_server_matches(row: McpServerRow, written: McpServerCreateBody, *, where: str) -> None:
+    stored: Final = (row.server_name, row.alias, row.url, row.transport, row.description, row.mcp_info)
+    expected: Final = (
+        written.server_name,
+        written.alias,
+        written.url,
+        written.transport,
+        written.description,
+        written.mcp_info,
+    )
+    assert stored == expected, f"{where}: stored {stored}, expected {expected}"
+
+
+def _server_everywhere(
+    client: ManagementClient, server_id: str, *, settled: Callable[[McpServerRow], bool]
+) -> Mapping[str, McpServerRow]:
+    return client.proxy.read_body_back_everywhere(f"/v1/mcp/server/{server_id}", McpServerRow, settled=settled)
+
+
+def _listed_server_everywhere(client: ManagementClient, server_id: str) -> Mapping[str, McpServerRow]:
+    listings: Final = client.proxy.read_body_back_everywhere(
+        "/v1/mcp/server",
+        McpServerListResponse,
+        settled=lambda rows: any(row.server_id == server_id for row in rows.root),
+    )
+    return {replica: next(row for row in rows.root if row.server_id == server_id) for replica, rows in listings.items()}
+
+
+class TestMcpServerLifecycle:
+    @pytest.mark.covers("mgmt.mcp_server.new.persists")
+    def test_create_persists_every_field_on_every_replica(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        body, server_id = _create_server(client, resources)
+
+        by_id: Final = _server_everywhere(client, server_id, settled=lambda row: row.server_id == server_id)
+        for replica, row in by_id.items():
+            _assert_server_matches(row, body, where=f"GET /v1/mcp/server/{server_id} on {replica}")
+
+    @pytest.mark.skip(
+        reason=(
+            "product gap: GET /v1/mcp/server builds each row from the in-memory registry, whose "
+            "_build_mcp_server_table sets description from mcp_info['description'], so the list "
+            "reports the mcp_info description while GET /v1/mcp/server/{server_id} reports the "
+            "stored description column. A server created with both set to different text reads "
+            "back with two different descriptions depending on the route"
+        )
+    )
+    @pytest.mark.covers("mgmt.mcp_server.list.persists")
+    def test_created_server_is_listed_with_every_field(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        body, server_id = _create_server(client, resources)
+
+        for replica, row in _listed_server_everywhere(client, server_id).items():
+            _assert_server_matches(row, body, where=f"GET /v1/mcp/server on {replica}")
+
+    @pytest.mark.covers("mgmt.mcp_server.update.preserves_unrelated_fields")
+    def test_updating_only_the_alias_keeps_every_other_field_on_every_replica(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        body, server_id = _create_server(client, resources)
+        renamed: Final = f"{body.alias}_renamed"
+
+        _ = client.update_mcp_server(McpServerUpdateBody(server_id=server_id, alias=renamed))
+
+        after_one_put: Final = _server_everywhere(client, server_id, settled=lambda row: row.alias == renamed)
+        for replica, row in after_one_put.items():
+            _assert_server_matches(
+                row,
+                body.model_copy(update={"alias": renamed}),
+                where=f"GET /v1/mcp/server/{server_id} on {replica} after one PUT of alias",
+            )
+
+    @pytest.mark.covers("mgmt.mcp_server.update.clear_persists")
+    def test_clearing_the_description_with_null_reads_back_null(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        body, server_id = _create_server(client, resources)
+
+        _ = client.update_mcp_server(McpServerUpdateBody(server_id=server_id, description=None))
+
+        cleared: Final = _server_everywhere(client, server_id, settled=lambda row: row.description is None)
+        for replica, row in cleared.items():
+            _assert_server_matches(
+                row,
+                body.model_copy(update={"description": None}),
+                where=f"GET /v1/mcp/server/{server_id} on {replica} after PUT description=null",
+            )
+
+    @pytest.mark.covers("mgmt.mcp_server.delete.persists")
+    def test_delete_removes_the_server_from_every_replica(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        _, server_id = _create_server(client, resources)
+
+        _ = unwrap(client.delete_mcp_server(server_id))
+
+        gone: Final = client.proxy.gone_everywhere(f"/v1/mcp/server/{server_id}")
+        assert set(gone.values()) == {404}, f"a deleted server must 404 on every replica; got {dict(gone)}"
+        listings: Final = client.proxy.read_body_back_everywhere(
+            "/v1/mcp/server",
+            McpServerListResponse,
+            settled=lambda rows: all(row.server_id != server_id for row in rows.root),
+        )
+        for replica, rows in listings.items():
+            assert all(row.server_id != server_id for row in rows.root), (
+                f"GET /v1/mcp/server on {replica} still lists the deleted server {server_id}"
+            )
+
+
+def _create_toolset(
+    client: ManagementClient, resources: ResourceManager, server_id: str
+) -> tuple[ToolsetCreateBody, str]:
+    body: Final = ToolsetCreateBody(
+        toolset_name=f"e2e_toolset_{unique_marker()}",
+        description="e2e lifecycle toolset",
+        tools=[
+            ToolsetTool(server_id=server_id, tool_name="search_datadog_logs"),
+            ToolsetTool(server_id=server_id, tool_name="get_datadog_metric"),
+        ],
+    )
+    toolset_id: Final = client.proxy.create_toolset(body).toolset_id
+    resources.defer(lambda: client.proxy.delete_toolset(toolset_id))
+    return body, toolset_id
+
+
+def _assert_toolset_matches(row: ToolsetRow, written: ToolsetCreateBody, *, where: str) -> None:
+    stored: Final = (row.toolset_name, row.description, row.tools)
+    expected: Final = (written.toolset_name, written.description, written.tools)
+    assert stored == expected, f"{where}: stored {stored}, expected {expected}"
+
+
+def _toolset_everywhere(
+    client: ManagementClient, toolset_id: str, *, settled: Callable[[ToolsetRow], bool]
+) -> Mapping[str, ToolsetRow]:
+    return client.proxy.read_body_back_everywhere(f"/v1/mcp/toolset/{toolset_id}", ToolsetRow, settled=settled)
+
+
+class TestMcpToolsetLifecycle:
+    @pytest.mark.covers("mgmt.mcp_toolset.new.persists")
+    def test_create_persists_both_tools_under_the_exact_names_written(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        _, server_id = _create_server(client, resources)
+        body, toolset_id = _create_toolset(client, resources, server_id)
+
+        by_id: Final = _toolset_everywhere(client, toolset_id, settled=lambda row: row.toolset_id == toolset_id)
+        for replica, row in by_id.items():
+            _assert_toolset_matches(row, body, where=f"GET /v1/mcp/toolset/{toolset_id} on {replica}")
+        listings: Final = client.proxy.read_body_back_everywhere(
+            "/v1/mcp/toolset",
+            ToolsetListResponse,
+            settled=lambda rows: any(row.toolset_id == toolset_id for row in rows.root),
+        )
+        for replica, rows in listings.items():
+            _assert_toolset_matches(
+                next(row for row in rows.root if row.toolset_id == toolset_id),
+                body,
+                where=f"GET /v1/mcp/toolset on {replica}",
+            )
+
+    @pytest.mark.covers("mgmt.mcp_toolset.update.preserves_unrelated_fields")
+    def test_updating_only_the_description_keeps_the_tools_and_name(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        _, server_id = _create_server(client, resources)
+        body, toolset_id = _create_toolset(client, resources, server_id)
+
+        _ = client.proxy.update_toolset(ToolsetUpdateBody(toolset_id=toolset_id, description="edited"))
+
+        edited: Final = _toolset_everywhere(client, toolset_id, settled=lambda row: row.description == "edited")
+        for replica, row in edited.items():
+            _assert_toolset_matches(
+                row,
+                body.model_copy(update={"description": "edited"}),
+                where=f"GET /v1/mcp/toolset/{toolset_id} on {replica} after PUT of description",
+            )
+
+    @pytest.mark.covers("mgmt.mcp_toolset.update.persists")
+    def test_updating_the_tools_to_one_entry_reads_back_exactly_that_entry(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        _, server_id = _create_server(client, resources)
+        body, toolset_id = _create_toolset(client, resources, server_id)
+        kept: Final = body.tools[:1]
+
+        _ = client.proxy.update_toolset(ToolsetUpdateBody(toolset_id=toolset_id, tools=kept))
+
+        narrowed: Final = _toolset_everywhere(client, toolset_id, settled=lambda row: row.tools == kept)
+        for replica, row in narrowed.items():
+            _assert_toolset_matches(
+                row,
+                body.model_copy(update={"tools": kept}),
+                where=f"GET /v1/mcp/toolset/{toolset_id} on {replica} after PUT of one tool",
+            )
+
+    @pytest.mark.covers("mgmt.mcp_toolset.update.clear_persists")
+    def test_clearing_the_description_with_null_reads_back_null(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        _, server_id = _create_server(client, resources)
+        body, toolset_id = _create_toolset(client, resources, server_id)
+
+        _ = client.proxy.update_toolset(ToolsetUpdateBody(toolset_id=toolset_id, description=None))
+
+        cleared: Final = _toolset_everywhere(client, toolset_id, settled=lambda row: row.description is None)
+        for replica, row in cleared.items():
+            _assert_toolset_matches(
+                row,
+                body.model_copy(update={"description": None}),
+                where=f"GET /v1/mcp/toolset/{toolset_id} on {replica} after PUT description=null",
+            )
+
+    @pytest.mark.covers("mgmt.mcp_toolset.delete.persists")
+    def test_delete_removes_the_toolset_from_every_replica(
+        self, client: ManagementClient, resources: ResourceManager
+    ) -> None:
+        _, server_id = _create_server(client, resources)
+        _, toolset_id = _create_toolset(client, resources, server_id)
+
+        _ = unwrap(client.proxy.delete_toolset(toolset_id))
+
+        gone: Final = client.proxy.gone_everywhere(f"/v1/mcp/toolset/{toolset_id}")
+        assert set(gone.values()) == {404}, f"a deleted toolset must 404 on every replica; got {dict(gone)}"
+        listings: Final = client.proxy.read_body_back_everywhere(
+            "/v1/mcp/toolset",
+            ToolsetListResponse,
+            settled=lambda rows: all(row.toolset_id != toolset_id for row in rows.root),
+        )
+        for replica, rows in listings.items():
+            assert all(row.toolset_id != toolset_id for row in rows.root), (
+                f"GET /v1/mcp/toolset on {replica} still lists the deleted toolset {toolset_id}"
+            )
diff --git a/tests/e2e/mcp/datadog_mcp.py b/tests/e2e/mcp/datadog_mcp.py
index d1ea53a0b3b..352b4446cfd 100644
--- a/tests/e2e/mcp/datadog_mcp.py
+++ b/tests/e2e/mcp/datadog_mcp.py
@@ -3,6 +3,7 @@
 from __future__ import annotations
 
 import os
+from collections.abc import Sequence
 
 from e2e_config import datadog_mcp_url, unique_marker
 from lifecycle import ResourceManager
@@ -35,7 +36,11 @@ def register_datadog_mcp(
     resources: ResourceManager,
     *,
     mcp_access_groups: list[str] | None = None,
+    allowed_tools: Sequence[str] | None = (SEARCH_LOGS_TOOL,),
 ) -> str:
+    """Register the core Datadog toolset with its credentials from the env. By default
+    the server exposes only `search_datadog_logs`; pass `allowed_tools=None` to expose
+    every tool the core toolset serves."""
     assert_dd_mcp_creds()
     name = f"e2e_dd_mcp_{unique_marker()}"
     server_id = client.register_server(
@@ -47,7 +52,7 @@ def register_datadog_mcp(
             "DD-API-KEY": _dd_api_key(),
             "DD-APPLICATION-KEY": _dd_app_key(),
         },
-        allowed_tools=[SEARCH_LOGS_TOOL],
+        allowed_tools=None if allowed_tools is None else list(allowed_tools),
         mcp_access_groups=mcp_access_groups,
     )
     resources.defer(lambda: client.delete_server(server_id))
diff --git a/tests/e2e/mcp/mcp_client.py b/tests/e2e/mcp/mcp_client.py
index 73453478e5a..210fc7a1e98 100644
--- a/tests/e2e/mcp/mcp_client.py
+++ b/tests/e2e/mcp/mcp_client.py
@@ -16,11 +16,11 @@ import time
 from collections.abc import Mapping
 from dataclasses import dataclass
 
-from pydantic import BaseModel, ConfigDict, Field, RootModel
+from pydantic import BaseModel, ConfigDict, Field
 
 from e2e_config import settle_propagation
 from e2e_http import Headers, NoBody, Result, Success, UnknownApiError, unwrap
-from models import KeyGenerateBody, ObjectPermission
+from models import KeyGenerateBody, McpServerListResponse, McpServerRow, ObjectPermission
 from proxy_client import ProxyClient
 
 McpToolArg = str | int | float | bool | list[str] | dict[str, str]
@@ -46,16 +46,6 @@ class McpServerNewResponse(BaseModel):
     server_id: str
 
 
-class McpServerRow(BaseModel):
-    server_id: str
-    alias: str | None = None
-    url: str | None = None
-
-
-class McpServersListResponse(RootModel[list[McpServerRow]]):
-    pass
-
-
 class McpToolMcpInfo(BaseModel):
     server_id: str | None = None
     alias: str | None = None
@@ -193,7 +183,7 @@ class McpClient:
                 "/v1/mcp/server",
                 headers=self.proxy.transport.master,
                 params=NoBody(),
-                response_type=McpServersListResponse,
+                response_type=McpServerListResponse,
             )
         ).root
 
@@ -224,11 +214,16 @@ class McpClient:
         user_id: str,
         mcp_servers: list[str] | None,
         mcp_access_groups: list[str] | None = None,
+        mcp_toolsets: list[str] | None = None,
         models: list[str] | None = None,
     ) -> str:
         object_permission = (
-            ObjectPermission(mcp_servers=mcp_servers, mcp_access_groups=mcp_access_groups)
-            if mcp_servers is not None or mcp_access_groups is not None
+            ObjectPermission(
+                mcp_servers=mcp_servers,
+                mcp_access_groups=mcp_access_groups,
+                mcp_toolsets=mcp_toolsets,
+            )
+            if mcp_servers is not None or mcp_access_groups is not None or mcp_toolsets is not None
             else None
         )
         return self.proxy.generate_key(
@@ -272,6 +267,20 @@ class McpClient:
                 )
             time.sleep(self.proxy.poll_interval)
 
+    def await_tools(self, key: str, server_id: str, *, expected: frozenset[str]) -> frozenset[str]:
+        """Poll tools/list until `server_id`'s tools as `key` sees them are exactly
+        `expected`, and return the last listing either way, so the caller's equality
+        assertion names the difference. Fails at poll_timeout only when the read
+        itself never succeeded."""
+        deadline = time.monotonic() + self.proxy.poll_timeout
+        while True:
+            result = self.list_tools(key)
+            if isinstance(result, Success) and result.data.tool_names_for_server(server_id) == expected:
+                return expected
+            if time.monotonic() >= deadline:
+                return unwrap(result).tool_names_for_server(server_id)
+            time.sleep(self.proxy.poll_interval)
+
     def await_call_tool(
         self,
         key: str,
diff --git a/tests/e2e/mcp/test_mcp_toolset_enforcement_e2e.py b/tests/e2e/mcp/test_mcp_toolset_enforcement_e2e.py
new file mode 100644
index 00000000000..6b901145eb1
--- /dev/null
+++ b/tests/e2e/mcp/test_mcp_toolset_enforcement_e2e.py
@@ -0,0 +1,95 @@
+"""Live e2e: a key granted a toolset lists exactly the toolset's tools.
+
+An admin registers the real Datadog remote MCP server with its whole core toolset
+exposed, discovers two of its tool names through a key granted the server outright,
+and curates a toolset naming exactly those two. A second key is granted the server
+plus that toolset, and its tools/list must come back as exactly those two names: no
+more, so the rest of the server's catalog stays hidden behind the toolset, and no
+fewer, so a tool stored under one name and read under another (which granted
+nothing) fails here first. Requires DD_API_KEY + DD_APP_KEY (the suite's real MCP
+upstream).
+"""
+
+from __future__ import annotations
+
+from typing import Final
+
+import pytest
+from datadog_mcp import SEARCH_LOGS_TOOL, register_datadog_mcp
+from e2e_config import unique_marker
+from e2e_http import unwrap
+from lifecycle import ResourceManager
+from mcp_client import McpClient
+from models import ToolsetCreateBody, ToolsetTool
+
+pytestmark = pytest.mark.e2e
+
+
+def _key(
+    client: McpClient,
+    resources: ResourceManager,
+    label: str,
+    *,
+    server_id: str,
+    toolset_id: str | None = None,
+) -> str:
+    key: Final = client.generate_key(
+        user_id=f"e2e-mcp-{label}-{unique_marker()}",
+        mcp_servers=[server_id],
+        mcp_toolsets=None if toolset_id is None else [toolset_id],
+    )
+    resources.defer(lambda: client.proxy.delete_key(key))
+    return key
+
+
+def _wire_prefix(wire_name: str, tool_name: str, catalog: frozenset[str]) -> str:
+    """The prefix tools/list puts in front of one server's tool names, measured off a
+    tool whose own name is known rather than guessed from the alias. A toolset grants
+    by the tool's own name, never the wire name, and the prefix is whatever the proxy
+    is configured to build (the alias, or a short server id), so measuring it is the
+    only way to cross between the two."""
+    assert wire_name.endswith(tool_name), f"tools/list served {wire_name!r}, expected it to end with {tool_name!r}"
+    prefix: Final = wire_name[: len(wire_name) - len(tool_name)]
+    unprefixed: Final = frozenset(name for name in catalog if not name.startswith(prefix))
+    assert not unprefixed, (
+        f"every tool of one server shares the wire prefix {prefix!r}, so {sorted(unprefixed)} "
+        f"cannot be reduced to the names a toolset grants by"
+    )
+    return prefix
+
+
+class TestMcpToolsetEnforcement:
+    @pytest.mark.covers("mcp.list_tools.api_key.toolset_scoped")
+    def test_key_granted_a_toolset_lists_exactly_its_tools(self, client: McpClient, resources: ResourceManager) -> None:
+        server_id: Final = register_datadog_mcp(client, resources, allowed_tools=None)
+        client.await_registered(server_id)
+
+        catalog_key: Final = _key(client, resources, "catalog", server_id=server_id)
+        known_wire: Final = client.await_tool(catalog_key, server_id, SEARCH_LOGS_TOOL)
+        catalog: Final = unwrap(client.list_tools(catalog_key)).tool_names_for_server(server_id)
+        assert len(catalog) > 2, (
+            f"the Datadog core toolset must serve more tools than the toolset names, or the "
+            f"restriction has nothing to hide; got {sorted(catalog)}"
+        )
+        prefix: Final = _wire_prefix(known_wire, SEARCH_LOGS_TOOL, catalog)
+        chosen_wire: Final = frozenset(sorted(catalog)[:2])
+        chosen: Final = frozenset(name.removeprefix(prefix) for name in chosen_wire)
+
+        toolset: Final = client.proxy.create_toolset(
+            ToolsetCreateBody(
+                toolset_name=f"e2e_toolset_{unique_marker()}",
+                description="two Datadog tools",
+                tools=[ToolsetTool(server_id=server_id, tool_name=name) for name in sorted(chosen)],
+            )
+        )
+        resources.defer(lambda: client.proxy.delete_toolset(toolset.toolset_id))
+        assert frozenset(tool.tool_name for tool in toolset.tools) == chosen, (
+            f"toolset stored {toolset.tools}, expected the two names {sorted(chosen)} verbatim"
+        )
+
+        scoped_key: Final = _key(client, resources, "toolset", server_id=server_id, toolset_id=toolset.toolset_id)
+        listed: Final = client.await_tools(scoped_key, server_id, expected=chosen_wire)
+        assert listed == chosen_wire, (
+            f"a key granted the toolset must list exactly its two tools; "
+            f"got {sorted(listed)}, expected {sorted(chosen_wire)}"
+        )
diff --git a/tests/e2e/models.py b/tests/e2e/models.py
index 9f2654e0eec..faf8557498b 100644
--- a/tests/e2e/models.py
+++ b/tests/e2e/models.py
@@ -10,6 +10,7 @@ from collections.abc import Sequence
 from datetime import datetime
 from typing import Final, Literal
 
+from e2e_http import PartialBody
 from pydantic import AliasChoices, BaseModel, ConfigDict, Field, RootModel, model_serializer, model_validator
 
 # ---------- keys ----------
@@ -55,6 +56,7 @@ class KeyMetadata(BaseModel):
 class ObjectPermission(BaseModel):
     mcp_servers: list[str] | None = None
     mcp_access_groups: list[str] | None = None
+    mcp_toolsets: list[str] | None = None
 
 
 class KeyGenerateBody(BaseModel):
@@ -77,11 +79,12 @@ class KeyGenerateBody(BaseModel):
     allowed_passthrough_routes: list[str] | None = None
     metadata: KeyMetadata | None = None
     object_permission: ObjectPermission | None = None
-    router_settings: "RouterSettingsOverride | None" = None
+    router_settings: RouterSettingsOverride | None = None
 
 
 class KeyGenerateResponse(BaseModel):
     key: str
+    token: str | None = None
     key_alias: str | None = None
     models: list[str] = []
     max_budget: float | None = None
@@ -516,6 +519,15 @@ class CountTokensResponse(BaseModel):
 # ---------- mcp servers ----------
 
 
+class McpInfo(BaseModel):
+    """The `mcp_info` display block stored on an MCP server; only the fields the
+    lifecycle test writes and reads back."""
+
+    server_name: str | None = None
+    description: str | None = None
+    logo_url: str | None = None
+
+
 class McpServerCreateBody(BaseModel):
     """POST /v1/mcp/server. For a gateway-managed OAuth server, `auth_type` is
     `oauth2` and `oauth2_flow` is `authorization_code`; the upstream endpoints
@@ -530,6 +542,18 @@ class McpServerCreateBody(BaseModel):
     oauth2_flow: Literal["client_credentials", "authorization_code"] | None = None
     authorization_url: str | None = None
     token_url: str | None = None
+    server_name: str | None = None
+    description: str | None = None
+    mcp_info: McpInfo | None = None
+
+
+class McpServerUpdateBody(PartialBody):
+    """PUT /v1/mcp/server: a field left unset keeps its stored value, a field set
+    to None is cleared."""
+
+    server_id: str
+    alias: str | None = None
+    description: str | None = None
 
 
 class McpServerInfo(BaseModel):
@@ -543,6 +567,54 @@ class McpServerInfo(BaseModel):
     allow_all_keys: bool | None = None
 
 
+class McpServerRow(McpServerInfo):
+    """A stored MCP server as the create, get, and list routes return it: the
+    fields the lifecycle test asserts survive the round trip."""
+
+    server_name: str | None = None
+    transport: str | None = None
+    description: str | None = None
+    mcp_info: McpInfo | None = None
+
+
+class McpServerListResponse(RootModel[list[McpServerRow]]):
+    """GET /v1/mcp/server answers with a bare array of servers."""
+
+
+class ToolsetTool(BaseModel):
+    server_id: str
+    tool_name: str
+
+
+class ToolsetCreateBody(BaseModel):
+    toolset_name: str
+    description: str | None = None
+    tools: list[ToolsetTool]
+
+
+class ToolsetUpdateBody(PartialBody):
+    """PUT /v1/mcp/toolset: a field left unset keeps its stored value, a field set
+    to None is cleared."""
+
+    toolset_id: str
+    description: str | None = None
+    tools: list[ToolsetTool] | None = None
+
+
+class ToolsetRow(BaseModel):
+    """A stored toolset as POST /v1/mcp/toolset, GET /v1/mcp/toolset/{toolset_id},
+    and each row of GET /v1/mcp/toolset return it."""
+
+    toolset_id: str
+    toolset_name: str
+    description: str | None = None
+    tools: list[ToolsetTool] = Field(default_factory=list)
+
+
+class ToolsetListResponse(RootModel[list[ToolsetRow]]):
+    """GET /v1/mcp/toolset answers with a bare array of toolsets."""
+
+
 class EmbedBody(BaseModel):
     model: str
     input: str
@@ -601,6 +673,7 @@ class GuardrailRunRecord(BaseModel):
 
 
 class SpendLogMetadata(BaseModel):
+    user_api_key_alias: str | None = None
     applied_guardrails: list[str] | None = None
     guardrail_information: list[GuardrailRunRecord] | None = None
 
diff --git a/tests/e2e/proxy_client.py b/tests/e2e/proxy_client.py
index 520cbfde5a9..1bac5116a9d 100644
--- a/tests/e2e/proxy_client.py
+++ b/tests/e2e/proxy_client.py
@@ -12,6 +12,7 @@ import time
 import warnings
 from collections.abc import Callable, Mapping
 from dataclasses import dataclass
+from functools import reduce
 from datetime import datetime
 from types import MappingProxyType
 from typing import Final
@@ -26,6 +27,7 @@ from e2e_http import (
     Result,
     StreamingResponse,
     Success,
+    UnknownApiError,
     is_ok,
     unwrap,
 )
@@ -70,6 +72,9 @@ from models import (
     SpendLogsPage,
     SpendLogsPageParams,
     SpendLogsParams,
+    ToolsetCreateBody,
+    ToolsetRow,
+    ToolsetUpdateBody,
 )
 from e2e_config import (
     CONTROL_PLANE_BASE_URL,
@@ -82,7 +87,7 @@ from e2e_config import (
     SLOW_PROVIDER_TIMEOUT_SECONDS,
     settle_propagation,
 )
-from transport import HttpTransport, SplitTransport, Transport
+from transport import HttpTransport, SplitTransport, Transport, is_control_plane_path
 
 RowsPredicate = Callable[[list[SpendLogRow]], bool]
 
@@ -235,6 +240,99 @@ def servable_timeout_message(
     )
 
 
+type ReplicaRead[T] = Callable[[float], T]
+
+
+@dataclass(frozen=True, slots=True)
+class EverywhereConverged[T]:
+    """Every replica answered with something `settled` accepts, keyed by replica."""
+
+    answers: Mapping[str, T]
+
+
+@dataclass(frozen=True, slots=True)
+class NeverConvergedOn[T]:
+    """`replica` ran out its budget without an answer `settled` accepts; `last` is
+    its final answer, so the failure can say what that replica still serves."""
+
+    replica: str
+    last: T
+
+
+def _last_answer[T](
+    read: ReplicaRead[T],
+    *,
+    settled: Callable[[T], bool],
+    timeout: float,
+    interval: float,
+    request_timeout: float,
+    now: Callable[[], float],
+    sleep: Callable[[float], None],
+) -> T:
+    """Poll `read` until `settled` accepts its answer or `timeout` runs out, and
+    return the last answer either way. Each read's request timeout is clamped to
+    the budget left, and the final poll runs even when less than an interval
+    remains, so a deadline never skips the read that would have settled."""
+    deadline: Final = now() + timeout
+    answer = read(min(request_timeout, timeout))
+    while not settled(answer):
+        remaining = deadline - now()
+        if remaining <= 0:
+            return answer
+        sleep(min(interval, remaining))
+        answer = read(min(request_timeout, remaining))
+    return answer
+
+
+def await_everywhere[T](
+    reads: Mapping[str, ReplicaRead[T]],
+    *,
+    settled: Callable[[T], bool],
+    timeout: float,
+    interval: float,
+    request_timeout: float,
+    now: Callable[[], float],
+    sleep: Callable[[float], None],
+) -> EverywhereConverged[T] | NeverConvergedOn[T]:
+    """`_last_answer` against every replica in turn, each with the full budget, so a
+    write counts as visible only once the last replica reflects it, and stop at the
+    first replica that never converges. Clock and sleep are injected."""
+    def read_replica(
+        outcome: EverywhereConverged[T] | NeverConvergedOn[T],
+        item: tuple[str, ReplicaRead[T]],
+    ) -> EverywhereConverged[T] | NeverConvergedOn[T]:
+        if isinstance(outcome, NeverConvergedOn):
+            return outcome
+        replica, read = item
+        answer: Final = _last_answer(
+            read,
+            settled=settled,
+            timeout=timeout,
+            interval=interval,
+            request_timeout=request_timeout,
+            now=now,
+            sleep=sleep,
+        )
+        if not settled(answer):
+            return NeverConvergedOn(replica=replica, last=answer)
+        return EverywhereConverged(answers=MappingProxyType({**outcome.answers, replica: answer}))
+
+    initial: Final[EverywhereConverged[T] | NeverConvergedOn[T]] = EverywhereConverged(answers=MappingProxyType({}))
+    return reduce(read_replica, reads.items(), initial)
+
+
+def _is_not_found[R: BaseModel](result: Result[R]) -> bool:
+    return isinstance(result, UnknownApiError) and result.status_code == 404
+
+
+def _status_of[R: BaseModel](result: Result[R]) -> int:
+    match result:
+        case Success(status_code=status_code) | UnknownApiError(status_code=status_code):
+            return status_code
+        case _:
+            return -1
+
+
 type Poller[T] = Callable[[], T]
 
 
@@ -321,6 +419,7 @@ def converge_timeout_message(*, what: str, replica: str, timeout: float, last_re
 class ProxyClient:
     transport: Transport
     replicas: Mapping[str, Transport]
+    control_replicas: Mapping[str, Transport]
     poll_timeout: float = 120.0
     poll_interval: float = 5.0
     model_servable_timeout: float = MODEL_SERVABLE_TIMEOUT
@@ -569,6 +668,112 @@ class ProxyClient:
         if not is_ok(result):
             warnings.warn(f"delete_model({model_id!r}) failed: {result}", stacklevel=2)
 
+    # ---- replica read-back ----------------------------------------------
+
+    def replicas_for(self, path: str) -> Mapping[str, Transport]:
+        """The replicas that serve `path`: every data-plane replica for an LLM route,
+        and for a management route the control-plane replicas, since the data-plane
+        replicas trim management routes and answer them 404. A monolith serves both
+        from every replica, so a management read-back polls all of them; a split
+        deployment exposes one control-plane address (there is one backend process
+        behind it on the stack these suites run against), so it polls that. A
+        control plane fronting several backends would need its own replica list to
+        prove each one converged, the way PROXY_REPLICA_URLS does for the gateways.
+        Never empty: a read-back against no replica would assert nothing and pass."""
+        replicas: Final = self.control_replicas if is_control_plane_path(path) else self.replicas
+        assert replicas, f"no replica is configured to serve {path}, so a read-back there would prove nothing"
+        return replicas
+
+    def read_body_back_everywhere[R: BaseModel](
+        self, path: str, response_type: type[R], *, settled: Callable[[R], bool]
+    ) -> Mapping[str, R]:
+        """GET `path` on every replica that serves it, polling each to poll_timeout
+        until `settled` accepts its body, and fail naming the first replica that
+        never converged. Returns each replica's settled body, keyed by replica, so
+        the caller can assert the rest of it."""
+        outcome: Final = await_everywhere(
+            {url: self._reader(transport, path, response_type) for url, transport in self.replicas_for(path).items()},
+            settled=lambda result: isinstance(result, Success) and settled(result.data),
+            timeout=self.poll_timeout,
+            interval=self.poll_interval,
+            request_timeout=REQUEST_TIMEOUT,
+            now=time.monotonic,
+            sleep=time.sleep,
+        )
+        match outcome:
+            case EverywhereConverged(answers=answers):
+                return MappingProxyType({url: unwrap(result) for url, result in answers.items()})
+            case NeverConvergedOn(replica=replica, last=last):
+                raise AssertionError(
+                    f"GET {path} on {replica} never converged within {self.poll_timeout}s of the write; "
+                    f"last read: {last}"
+                )
+
+    def gone_everywhere(self, path: str) -> Mapping[str, int]:
+        """Poll GET `path` on every replica that serves it until each stops serving
+        it, and fail naming the first replica that still does at poll_timeout.
+        Returns each replica's final status, so the caller asserts the 404 itself."""
+        outcome: Final = await_everywhere(
+            {url: self._reader(transport, path, NoBody) for url, transport in self.replicas_for(path).items()},
+            settled=_is_not_found,
+            timeout=self.poll_timeout,
+            interval=self.poll_interval,
+            request_timeout=REQUEST_TIMEOUT,
+            now=time.monotonic,
+            sleep=time.sleep,
+        )
+        match outcome:
+            case EverywhereConverged(answers=answers):
+                return MappingProxyType({url: _status_of(result) for url, result in answers.items()})
+            case NeverConvergedOn(replica=replica, last=last):
+                raise AssertionError(
+                    f"GET {path} on {replica} still answers {self.poll_timeout}s after the delete; last read: {last}"
+                )
+
+    @staticmethod
+    def _reader[R: BaseModel](transport: Transport, path: str, response_type: type[R]) -> ReplicaRead[Result[R]]:
+        return lambda request_timeout: transport.get(
+            path,
+            headers=transport.master,
+            params=NoBody(),
+            response_type=response_type,
+            timeout=request_timeout,
+        )
+
+    # ---- mcp toolsets ---------------------------------------------------
+
+    def create_toolset(self, body: ToolsetCreateBody) -> ToolsetRow:
+        return unwrap(
+            self.transport.post(
+                "/v1/mcp/toolset",
+                headers=self.transport.master,
+                json=body,
+                response_type=ToolsetRow,
+            )
+        )
+
+    def update_toolset(self, body: ToolsetUpdateBody) -> ToolsetRow:
+        """PUT /v1/mcp/toolset: a partial update where a field left unset keeps its
+        stored value and None clears it."""
+        return unwrap(
+            self.transport.put(
+                "/v1/mcp/toolset",
+                headers=self.transport.master,
+                json=body,
+                response_type=ToolsetRow,
+            )
+        )
+
+    def delete_toolset(self, toolset_id: str) -> Result[NoBody]:
+        """DELETE /v1/mcp/toolset/{toolset_id}. Returns the outcome so the act phase
+        can unwrap it while a deferred teardown can ignore an already-deleted row."""
+        return self.transport.delete(
+            f"/v1/mcp/toolset/{toolset_id}",
+            headers=self.transport.master,
+            json=NoBody(),
+            response_type=NoBody,
+        )
+
     def create_credential(self, body: CredentialCreateBody) -> None:
         unwrap(
             self.transport.post(
@@ -736,7 +941,10 @@ def build_proxy_client(
     base URLs are the same for a monolithic proxy, so routing is then a no-op.
     ``replica_urls`` (PROXY_REPLICA_URLS) names every data-plane replica the model
     barrier polls directly; it is the data-plane URL itself unless the stack
-    exports each gateway's own address.
+    exports each gateway's own address. Management read-backs poll those same
+    replicas when the two planes share a base URL (a monolith, where every replica
+    serves every route) and the control plane alone when they differ (a split
+    deployment, where the data-plane replicas do not serve management routes).
 
     The endpoints are injectable for callers that resolve the proxy some other
     way than ``e2e_config``'s env names (see ``claude_code/_env.py``); they must
@@ -764,9 +972,13 @@ def build_proxy_client(
             for url in replica_urls
         }
     )
+    control_replicas: Final = (
+        replicas if control_plane_base_url == base_url else MappingProxyType({control_plane_base_url: split.control})
+    )
     return ProxyClient(
         transport=split,
         replicas=replicas,
+        control_replicas=control_replicas,
         poll_timeout=POLL_TIMEOUT,
         poll_interval=POLL_INTERVAL,
     )
diff --git a/tests/e2e/quota_management/spend_tracking/conftest.py b/tests/e2e/quota_management/spend_tracking/conftest.py
index 0597c9af400..9c8ffd18144 100644
--- a/tests/e2e/quota_management/spend_tracking/conftest.py
+++ b/tests/e2e/quota_management/spend_tracking/conftest.py
@@ -36,6 +36,7 @@ DRIVER_MODELS: tuple[tuple[str, str, str], ...] = (
     ("claude-haiku-4-5", "anthropic/claude-haiku-4-5", "ANTHROPIC_API_KEY"),
     ("openai-text-embedding-3-small", "openai/text-embedding-3-small", "OPENAI_API_KEY"),
     ("openai-responses-codex", "openai/gpt-5.3-codex", "OPENAI_API_KEY"),
+    ("openai-gpt-4o-mini", "openai/gpt-4o-mini", "OPENAI_API_KEY"),
 )
 
 
diff --git a/tests/e2e/quota_management/spend_tracking/spend_e2e_client.py b/tests/e2e/quota_management/spend_tracking/spend_e2e_client.py
index 056799b8499..9ac97f57f47 100644
--- a/tests/e2e/quota_management/spend_tracking/spend_e2e_client.py
+++ b/tests/e2e/quota_management/spend_tracking/spend_e2e_client.py
@@ -15,9 +15,12 @@ import time
 from collections.abc import Callable
 from dataclasses import dataclass
 from datetime import datetime, timedelta, timezone
+from typing import Final
 
 from e2e_config import unique_marker
 from e2e_http import (
+    FileUploadForm,
+    Headers,
     NoBody,
     ProbeResult,
     Result,
@@ -35,6 +38,8 @@ from models import (
     DateRangeParams,
     EmbedBody,
     EmbedResponse,
+    KeyGenerateBody,
+    KeyGenerateResponse,
     OpenAPISchema,
     SpendCalculateBody,
     SpendCalculateResponse,
@@ -43,13 +48,27 @@ from models import (
     SpendLogsPageParams,
     SpendTagsResponse,
     TagSpend,
+    UserDeleteBody,
+    UserDeleteResponse,
+    UserNewBody,
+    UserNewResponse,
+    UserRole,
 )
-from proxy_client import ProxyClient
+from proxy_client import Converged, ProxyClient, await_converged
+from pydantic import BaseModel, Field
 
 __all__ = [
+    "BatchCreateBody",
+    "CallbackLogMetadata",
+    "CallbackLogPayload",
+    "BatchObject",
+    "DailyActivityKeyBreakdown",
+    "FileObject",
     "ProbeResult",
+    "ResponseIdentity",
     "SpendClient",
     "SpendLogRow",
+    "StreamingResponse",
     "build_client",
     "is_ok",
     "unique_marker",
@@ -57,6 +76,139 @@ __all__ = [
 ]
 
 
+class GeminiApiKeyHeaders(Headers):
+    x_goog_api_key: str = Field(serialization_alias="x-goog-api-key")
+    content_type: str = Field(default="application/json", serialization_alias="Content-Type")
+
+
+class GeminiPart(BaseModel):
+    text: str
+
+
+class GeminiContent(BaseModel):
+    parts: list[GeminiPart]
+
+
+class GeminiGenerationConfig(BaseModel):
+    maxOutputTokens: int
+
+
+class GeminiGenerateBody(BaseModel):
+    contents: list[GeminiContent]
+    generationConfig: GeminiGenerationConfig
+
+
+class ResponsesBody(BaseModel):
+    model: str
+    input: str
+    cache: dict[str, bool] | None = {"no-cache": True}
+
+
+class QueuedChatBody(ChatBody):
+    priority: int = 0
+
+
+class ResponseIdentity(BaseModel):
+    id: str | None = None
+
+
+class HealthParams(BaseModel):
+    model: str
+
+
+class ModelQuery(BaseModel):
+    model: str
+
+
+class FileObject(BaseModel):
+    id: str
+
+
+class BatchCreateBody(BaseModel):
+    input_file_id: str
+    endpoint: str = "/v1/chat/completions"
+    completion_window: str = "24h"
+    model: str
+    metadata: dict[str, str]
+
+
+class BatchObject(BaseModel):
+    id: str
+    status: str
+
+
+class ProviderQuery(BaseModel):
+    provider: str
+
+
+class CallbackLogMetadata(BaseModel):
+    user_api_key_hash: str
+    user_api_key_alias: str
+    user_api_key_user_id: str
+
+
+class CallbackLogPayload(BaseModel):
+    id: str
+    litellm_call_id: str
+    model: str
+    call_type: str = "acompletion"
+    start_time: float = Field(serialization_alias="startTime")
+    end_time: float = Field(serialization_alias="endTime")
+    response_cost: float
+    prompt_tokens: int
+    completion_tokens: int
+    total_tokens: int
+    metadata: CallbackLogMetadata
+
+
+class CallbackLogRecord(BaseModel):
+    status: str = "success"
+    standard_logging_payload: CallbackLogPayload
+
+
+class CallbackLogsRequest(BaseModel):
+    records: list[CallbackLogRecord]
+
+
+class CallbackLogsResponse(BaseModel):
+    processed: int
+    failed: int
+
+
+class DailyActivityParams(BaseModel):
+    start_date: str
+    end_date: str
+    api_key: str
+
+
+class DailyActivityKeyMetadata(BaseModel):
+    key_alias: str | None = None
+    team_id: str | None = None
+    user_email: str | None = None
+
+
+class DailyActivityKeyMetrics(BaseModel):
+    api_requests: int = 0
+
+
+class DailyActivityKeyBreakdown(BaseModel):
+    metrics: DailyActivityKeyMetrics
+    metadata: DailyActivityKeyMetadata
+
+
+class DailyActivityBreakdown(BaseModel):
+    api_keys: dict[str, DailyActivityKeyBreakdown] = {}
+
+
+class DailyActivityRow(BaseModel):
+    date: str
+    breakdown: DailyActivityBreakdown
+
+
+class DailyActivityResponse(BaseModel):
+    results: list[DailyActivityRow] = []
+
+
 def _chat_body(
     model: str,
     content: str,
@@ -207,6 +359,166 @@ class SpendClient:
     def probe(self, path: str, *, params: DateRangeParams) -> ProbeResult:
         return self.proxy.transport.probe(path, params=params)
 
+    def create_user(self, *, email: str, role: UserRole, user_id: str) -> str:
+        return unwrap(
+            self.proxy.transport.post(
+                "/user/new",
+                headers=self.proxy.transport.master,
+                json=UserNewBody(user_email=email, user_role=role, user_id=user_id),
+                response_type=UserNewResponse,
+            )
+        ).user_id
+
+    def delete_user(self, user_id: str) -> None:
+        _ = unwrap(
+            self.proxy.transport.post(
+                "/user/delete",
+                headers=self.proxy.transport.master,
+                json=UserDeleteBody(user_ids=[user_id]),
+                response_type=UserDeleteResponse,
+            )
+        )
+
+    def generate_key_record(self, body: KeyGenerateBody) -> KeyGenerateResponse:
+        return unwrap(
+            self.proxy.transport.post(
+                "/key/generate",
+                headers=self.proxy.transport.master,
+                json=body,
+                response_type=KeyGenerateResponse,
+            )
+        )
+
+    def send_chat(self, key: str, model: str, content: str, *, max_tokens: int) -> StreamingResponse:
+        return self.proxy.transport.send(
+            "/chat/completions",
+            headers=self.proxy.transport.bearer(key),
+            json=_chat_body(model, content, max_tokens=max_tokens),
+        )
+
+    def send_queued_chat(self, key: str, model: str, content: str, *, max_tokens: int) -> StreamingResponse:
+        return self.proxy.transport.send(
+            "/queue/chat/completions",
+            headers=self.proxy.transport.bearer(key),
+            json=QueuedChatBody(
+                model=model,
+                messages=[ChatMessage(role="user", content=content)],
+                max_tokens=max_tokens,
+            ),
+        )
+
+    def send_messages(self, key: str, model: str, content: str, *, max_tokens: int) -> StreamingResponse:
+        return self.proxy.transport.send(
+            "/v1/messages",
+            headers=self.proxy.transport.bearer(key),
+            json=AnthropicMessagesBody(
+                model=model,
+                messages=[ChatMessage(role="user", content=content)],
+                max_tokens=max_tokens,
+            ),
+        )
+
+    def send_responses(self, key: str, model: str, content: str) -> StreamingResponse:
+        return self.proxy.transport.send(
+            "/v1/responses",
+            headers=self.proxy.transport.bearer(key),
+            json=ResponsesBody(model=model, input=content),
+        )
+
+    def send_embed(self, key: str, model: str, content: str) -> StreamingResponse:
+        return self.proxy.transport.send(
+            "/embeddings",
+            headers=self.proxy.transport.bearer(key),
+            json=EmbedBody(model=model, input=content),
+        )
+
+    def send_gemini_generate(self, key: str, model: str, content: str, *, max_tokens: int) -> StreamingResponse:
+        return self.proxy.transport.send(
+            f"/gemini/v1beta/models/{model}:generateContent",
+            headers=GeminiApiKeyHeaders(x_goog_api_key=key),
+            json=GeminiGenerateBody(
+                contents=[GeminiContent(parts=[GeminiPart(text=content)])],
+                generationConfig=GeminiGenerationConfig(maxOutputTokens=max_tokens),
+            ),
+        )
+
+    def upload_batch_file(self, key: str, model: str, content: bytes) -> FileObject:
+        return unwrap(
+            self.proxy.transport.upload(
+                "/v1/files",
+                headers=self.proxy.transport.bearer(key),
+                form=FileUploadForm(purpose="batch"),
+                filename="key_attribution.jsonl",
+                content=content,
+                params=ModelQuery(model=model),
+                response_type=FileObject,
+            )
+        )
+
+    def create_batch(self, key: str, body: BatchCreateBody) -> BatchObject:
+        return unwrap(
+            self.proxy.transport.post(
+                "/v1/batches",
+                headers=self.proxy.transport.bearer(key),
+                json=body,
+                response_type=BatchObject,
+            )
+        )
+
+    def retrieve_batch(self, key: str, batch_id: str, *, provider: str) -> BatchObject:
+        return unwrap(
+            self.proxy.transport.get(
+                f"/v1/batches/{batch_id}",
+                headers=self.proxy.transport.bearer(key),
+                params=ProviderQuery(provider=provider),
+                response_type=BatchObject,
+            )
+        )
+
+    def replay_callback_log(self, key: str, payload: CallbackLogPayload) -> CallbackLogsResponse:
+        return unwrap(
+            self.proxy.transport.post(
+                "/v1/rust_control_plane/logs",
+                headers=self.proxy.transport.bearer(key),
+                json=CallbackLogsRequest(records=[CallbackLogRecord(standard_logging_payload=payload)]),
+                response_type=CallbackLogsResponse,
+            )
+        )
+
+    def health(self, model: str) -> ProbeResult:
+        return self.proxy.transport.probe("/health", params=HealthParams(model=model))
+
+    def daily_activity_for_key(self, token: str, *, start: datetime, end: datetime) -> DailyActivityKeyBreakdown | None:
+        response: Final = unwrap(
+            self.proxy.transport.get(
+                "/user/daily/activity",
+                headers=self.proxy.transport.master,
+                params=DailyActivityParams(
+                    start_date=start.strftime("%Y-%m-%d"),
+                    end_date=end.strftime("%Y-%m-%d"),
+                    api_key=token,
+                ),
+                response_type=DailyActivityResponse,
+            )
+        )
+        return next(
+            (row.breakdown.api_keys[token] for row in response.results if token in row.breakdown.api_keys),
+            None,
+        )
+
+    def poll_daily_activity_for_key(
+        self, token: str, *, start: datetime, end: datetime, min_requests: int
+    ) -> DailyActivityKeyBreakdown | None:
+        outcome: Final = await_converged(
+            lambda: self.daily_activity_for_key(token, start=start, end=end),
+            converged=lambda found: found is not None and found.metrics.api_requests >= min_requests,
+            timeout=self.proxy.poll_timeout,
+            interval=self.proxy.poll_interval,
+            now=time.monotonic,
+            sleep=time.sleep,
+        )
+        return outcome.result if isinstance(outcome, Converged) else outcome.last_result
+
     def openapi(self) -> OpenAPISchema:
         return unwrap(
             self.proxy.transport.get(
diff --git a/tests/e2e/quota_management/spend_tracking/test_key_attribution_e2e.py b/tests/e2e/quota_management/spend_tracking/test_key_attribution_e2e.py
new file mode 100644
index 00000000000..4a2c23927c6
--- /dev/null
+++ b/tests/e2e/quota_management/spend_tracking/test_key_attribution_e2e.py
@@ -0,0 +1,405 @@
+"""Every spend row a live proxy writes joins its virtual key (MAT-180).
+
+One virtual key with an alias, owned by a user with an email, drives every spend
+write path a key can reach: /chat/completions, /queue/chat/completions,
+/v1/messages, /v1/responses, /embeddings, the Gemini native passthrough, a batch
+input file upload, a batch create, and a replayed callback log (POST
+/v1/rust_control_plane/logs, the writer an external gateway feeds). Each row those calls write must carry
+`api_key` equal to the key's LiteLLM_VerificationToken.token (the sha256 hash
+/key/generate returns as `token`), which is the join /spend/logs?api_key= and
+/user/daily/activity rely on to report key_alias and user_email. A row keyed by a
+re-hashed token (v1.99.0's regression, #39568 and #39572) shows up as a
+key-hash-* row with no alias and no email in the customer's usage exports.
+
+The health-check service account writes rows too; those must stay keyed by the
+literal service-account name, never by a hash of it. A batch's cost row is
+written by the retrieve that first sees the batch in a terminal state, so the
+batch the run creates is one OpenAI fails at validation within seconds (its one
+line targets /v1/embeddings under a /v1/chat/completions batch), and the test
+retrieves it by its raw provider id with the same key until it is failed. A raw
+id is never owned by the CheckBatchCost poller, so that retrieve prices the batch
+inline against the retrieving key and its {provider_batch_id}_batch_cost row
+must join the key's token with its alias. A completed batch with a positive
+cost is out of a single run's reach (OpenAI's completion window is 24h, and a
+stack booted fresh per run lists no earlier run's batches), so the poller's own
+row is not asserted here.
+
+/spend/logs carries no email field, so the email assertion lives on
+/user/daily/activity alone; /spend/logs is held to the alias in metadata.
+"""
+
+import base64
+import time
+from collections.abc import Iterator
+from dataclasses import dataclass
+from datetime import datetime, timedelta, timezone
+from typing import Final
+
+import pytest
+from models import KeyGenerateBody
+from proxy_client import Converged, await_converged
+from pydantic import BaseModel
+from spend_e2e_client import (
+    BatchCreateBody,
+    BatchObject,
+    CallbackLogMetadata,
+    CallbackLogPayload,
+    DailyActivityKeyBreakdown,
+    ResponseIdentity,
+    SpendClient,
+    SpendLogRow,
+    StreamingResponse,
+    unique_marker,
+)
+
+pytestmark = pytest.mark.e2e
+
+CHAT_MODEL: Final = "gemini-2.5-flash"
+MESSAGES_MODEL: Final = "claude-haiku-4-5"
+RESPONSES_MODEL: Final = "openai-responses-codex"
+EMBED_MODEL: Final = "openai-text-embedding-3-small"
+BATCH_MODEL: Final = "openai-gpt-4o-mini"
+BATCH_BACKEND_MODEL: Final = "gpt-4o-mini"
+BATCH_PROVIDER: Final = "openai"
+HEALTH_SERVICE_ACCOUNT: Final = "litellm-internal-health-check"
+BATCH_TERMINAL_STATUSES: Final = frozenset({"completed", "failed", "cancelled", "expired"})
+FAILED_BATCH_POLL_SECONDS: Final = 120.0
+FAILED_BATCH_POLL_INTERVAL_SECONDS: Final = 5.0
+MAX_TOKENS: Final = 8
+REPLAY_RESPONSE_COST: Final = 0.0001
+REPLAY_PROMPT_TOKENS: Final = 5
+REPLAY_COMPLETION_TOKENS: Final = 1
+WRITE_PATHS: Final = (
+    "chat_completions",
+    "queue_chat_completions",
+    "messages",
+    "responses",
+    "embeddings",
+    "gemini_passthrough",
+    "batch_file_upload",
+    "batch_create",
+    "callback_replay",
+)
+
+
+class EmbeddingLineBody(BaseModel):
+    model: str
+    input: str
+
+
+class EmbeddingLine(BaseModel):
+    custom_id: str
+    method: str = "POST"
+    url: str = "/v1/embeddings"
+    body: EmbeddingLineBody
+
+
+@dataclass(frozen=True, slots=True)
+class AttributedKey:
+    key: str
+    token: str
+    alias: str
+    email: str
+    user_id: str
+
+
+@dataclass(frozen=True, slots=True)
+class WritePath:
+    name: str
+    request_id: str
+
+
+@dataclass(frozen=True, slots=True)
+class DrivenKey:
+    identity: AttributedKey
+    paths: tuple[WritePath, ...]
+    started_at: datetime
+
+
+def _body_id(name: str, sent: StreamingResponse) -> WritePath:
+    assert sent.ok, f"{name} failed with {sent.status_code}: {sent.body[:300]}"
+    response_id: Final = ResponseIdentity.model_validate_json(sent.body).id
+    assert response_id, f"{name} answered without a response id: {sent.body[:300]}"
+    return WritePath(name=name, request_id=response_id)
+
+
+def _call_id(name: str, sent: StreamingResponse) -> WritePath:
+    assert sent.ok, f"{name} failed with {sent.status_code}: {sent.body[:300]}"
+    assert sent.call_id, f"{name} answered without an x-litellm-call-id header"
+    return WritePath(name=name, request_id=sent.call_id)
+
+
+def _endpoint_mismatched_jsonl(marker: str) -> bytes:
+    line: Final = EmbeddingLine(custom_id=marker, body=EmbeddingLineBody(model=BATCH_BACKEND_MODEL, input=marker))
+    return f"{line.model_dump_json()}\n".encode()
+
+
+def _drive_batch(client: SpendClient, identity: AttributedKey, marker: str) -> tuple[WritePath, WritePath]:
+    uploaded: Final = client.upload_batch_file(identity.key, BATCH_MODEL, _endpoint_mismatched_jsonl(marker))
+    created: Final = client.create_batch(
+        identity.key,
+        BatchCreateBody(
+            input_file_id=uploaded.id,
+            model=BATCH_MODEL,
+            metadata={"run": marker},
+        ),
+    )
+    return (
+        WritePath(name="batch_file_upload", request_id=uploaded.id),
+        WritePath(name="batch_create", request_id=created.id),
+    )
+
+
+def _drive_callback_replay(client: SpendClient, identity: AttributedKey, marker: str) -> WritePath:
+    request_id: Final = f"callback-replay-{marker}"
+    finished_at: Final = time.time()
+    replayed: Final = client.replay_callback_log(
+        identity.key,
+        CallbackLogPayload(
+            id=request_id,
+            litellm_call_id=request_id,
+            model=CHAT_MODEL,
+            start_time=finished_at - 1,
+            end_time=finished_at,
+            response_cost=REPLAY_RESPONSE_COST,
+            prompt_tokens=REPLAY_PROMPT_TOKENS,
+            completion_tokens=REPLAY_COMPLETION_TOKENS,
+            total_tokens=REPLAY_PROMPT_TOKENS + REPLAY_COMPLETION_TOKENS,
+            metadata=CallbackLogMetadata(
+                user_api_key_hash=identity.token,
+                user_api_key_alias=identity.alias,
+                user_api_key_user_id=identity.user_id,
+            ),
+        ),
+    )
+    assert replayed.processed == 1 and replayed.failed == 0, f"callback replay rejected the payload: {replayed}"
+    return WritePath(name="callback_replay", request_id=request_id)
+
+
+def _drive_every_write_path(client: SpendClient, identity: AttributedKey) -> tuple[WritePath, ...]:
+    marker: Final = unique_marker()
+    prompt: Final = f"Reply with the word ok. {marker}"
+    key: Final = identity.key
+    return (
+        _body_id("chat_completions", client.send_chat(key, CHAT_MODEL, prompt, max_tokens=MAX_TOKENS)),
+        _body_id("queue_chat_completions", client.send_queued_chat(key, CHAT_MODEL, prompt, max_tokens=MAX_TOKENS)),
+        _body_id("messages", client.send_messages(key, MESSAGES_MODEL, prompt, max_tokens=MAX_TOKENS)),
+        _body_id("responses", client.send_responses(key, RESPONSES_MODEL, prompt)),
+        _call_id("embeddings", client.send_embed(key, EMBED_MODEL, prompt)),
+        _call_id("gemini_passthrough", client.send_gemini_generate(key, CHAT_MODEL, prompt, max_tokens=MAX_TOKENS)),
+        *_drive_batch(client, identity, marker),
+        _drive_callback_replay(client, identity, marker),
+    )
+
+
+def _provider_batch_id(unified_batch_id: str) -> str:
+    encoded: Final = unified_batch_id.removeprefix("batch_")
+    decoded: Final = base64.urlsafe_b64decode(encoded + "=" * (-len(encoded) % 4)).decode()
+    return decoded.removeprefix("litellm:").split(";", 1)[0]
+
+
+def _driven_batch_id(driven: DrivenKey) -> str:
+    return next(path.request_id for path in driven.paths if path.name == "batch_create")
+
+
+def _await_terminal_batch(client: SpendClient, key: str, provider_batch_id: str) -> BatchObject:
+    outcome: Final = await_converged(
+        lambda: client.retrieve_batch(key, provider_batch_id, provider=BATCH_PROVIDER),
+        converged=lambda batch: batch.status in BATCH_TERMINAL_STATUSES,
+        timeout=FAILED_BATCH_POLL_SECONDS,
+        interval=FAILED_BATCH_POLL_INTERVAL_SECONDS,
+        now=time.monotonic,
+        sleep=time.sleep,
+    )
+    return outcome.result if isinstance(outcome, Converged) else outcome.last_result
+
+
+def _health_rows_between(client: SpendClient, started_at: datetime) -> list[SpendLogRow]:
+    return [
+        row
+        for row in client.proxy.spend_logs_window(
+            start=started_at - timedelta(minutes=1), end=datetime.now(timezone.utc) + timedelta(minutes=1)
+        )
+        if HEALTH_SERVICE_ACCOUNT in (row.request_tags or [])
+    ]
+
+
+def _health_rows_since(client: SpendClient, started_at: datetime) -> list[SpendLogRow]:
+    outcome: Final = await_converged(
+        lambda: _health_rows_between(client, started_at),
+        converged=lambda rows: bool(rows),
+        timeout=client.proxy.poll_timeout,
+        interval=client.proxy.poll_interval,
+        now=time.monotonic,
+        sleep=time.sleep,
+    )
+    return outcome.result if isinstance(outcome, Converged) else outcome.last_result
+
+
+class TestKeyAttribution:
+    @pytest.fixture(scope="class")
+    def driven(self, client: SpendClient) -> Iterator[DrivenKey]:
+        marker: Final = unique_marker()
+        user_id: Final = client.create_user(
+            email=f"key-attribution-{marker}@example.com",
+            role="proxy_admin",
+            user_id=f"key-attribution-{marker}",
+        )
+        record: Final = client.generate_key_record(
+            KeyGenerateBody(models=[], user_id=user_id, key_alias=f"key-attribution-{marker}")
+        )
+        assert record.token, "/key/generate answered without the key's token hash"
+        assert record.key_alias, "/key/generate dropped the key alias"
+        identity: Final = AttributedKey(
+            key=record.key,
+            token=record.token,
+            alias=record.key_alias,
+            email=f"key-attribution-{marker}@example.com",
+            user_id=user_id,
+        )
+        started_at: Final = datetime.now(timezone.utc)
+        try:
+            yield DrivenKey(
+                identity=identity,
+                paths=_drive_every_write_path(client, identity),
+                started_at=started_at,
+            )
+        finally:
+            client.proxy.delete_key(identity.key)
+            client.delete_user(identity.user_id)
+
+    @pytest.mark.covers(
+        "quota_management.spend_tracking.key_attribution.joins_key",
+        exercised_on=[
+            "chat_completions",
+            "messages",
+            "responses",
+            "embeddings",
+            "batches",
+            "files",
+            "google_native",
+            "rust_control_plane",
+        ],
+    )
+    def test_every_write_path_row_joins_the_key(self, client: SpendClient, driven: DrivenKey) -> None:
+        assert tuple(path.name for path in driven.paths) == WRITE_PATHS
+        found: Final = tuple((path, client.proxy.poll_logs_for_request_id(path.request_id)) for path in driven.paths)
+        unwritten: Final = [path.name for path, rows in found if not rows]
+        assert not unwritten, f"write paths that produced no spend row within the poll window: {unwritten}"
+        unjoined: Final = [
+            (path.name, row.call_type, row.api_key)
+            for path, rows in found
+            for row in rows
+            if row.api_key != driven.identity.token
+        ]
+        assert not unjoined, (
+            "spend rows whose api_key does not join LiteLLM_VerificationToken.token "
+            f"{driven.identity.token}: {unjoined}"
+        )
+        unaliased: Final = [
+            (path.name, row.call_type, row.metadata.user_api_key_alias if row.metadata else None)
+            for path, rows in found
+            for row in rows
+            if row.metadata is None or row.metadata.user_api_key_alias != driven.identity.alias
+        ]
+        assert not unaliased, f"spend rows written without key alias {driven.identity.alias!r}: {unaliased}"
+
+    @pytest.mark.covers(
+        "quota_management.spend_tracking.key_attribution.reports_alias_and_email",
+        exercised_on=[
+            "chat_completions",
+            "messages",
+            "responses",
+            "embeddings",
+            "batches",
+            "files",
+            "google_native",
+            "rust_control_plane",
+        ],
+    )
+    def test_spend_logs_by_key_return_every_row_with_the_alias(self, client: SpendClient, driven: DrivenKey) -> None:
+        expected_ids: Final = frozenset(path.request_id for path in driven.paths)
+        rows: Final = client.poll_logs_for_key(
+            driven.identity.key,
+            min_rows=len(driven.paths),
+            predicate=lambda found: expected_ids <= frozenset(row.request_id or "" for row in found),
+        )
+        missing: Final = expected_ids - frozenset(row.request_id or "" for row in rows)
+        assert not missing, (
+            f"/spend/logs?api_key= does not return {len(missing)} of {len(expected_ids)} rows for the key: "
+            f"{sorted(path.name for path in driven.paths if path.request_id in missing)}"
+        )
+        aliases: Final = frozenset(row.metadata.user_api_key_alias if row.metadata else None for row in rows)
+        assert aliases == {driven.identity.alias}, f"/spend/logs rows carry aliases {sorted(map(str, aliases))}"
+
+    @pytest.mark.covers(
+        "quota_management.spend_tracking.key_attribution.reports_alias_and_email",
+        exercised_on=[
+            "chat_completions",
+            "messages",
+            "responses",
+            "embeddings",
+            "batches",
+            "files",
+            "google_native",
+            "rust_control_plane",
+        ],
+    )
+    def test_user_daily_activity_reports_alias_and_email(self, client: SpendClient, driven: DrivenKey) -> None:
+        breakdown: Final[DailyActivityKeyBreakdown | None] = client.poll_daily_activity_for_key(
+            driven.identity.token,
+            start=driven.started_at - timedelta(days=1),
+            end=datetime.now(timezone.utc) + timedelta(days=1),
+            min_requests=len(driven.paths),
+        )
+        assert breakdown is not None, (
+            f"/user/daily/activity?api_key={driven.identity.token} has no api_keys breakdown: "
+            "the key's rows did not aggregate under its token"
+        )
+        assert breakdown.metrics.api_requests >= len(driven.paths), (
+            f"/user/daily/activity counts {breakdown.metrics.api_requests} requests for the key, "
+            f"expected at least {len(driven.paths)}"
+        )
+        assert breakdown.metadata.key_alias == driven.identity.alias, f"key_alias={breakdown.metadata.key_alias!r}"
+        assert breakdown.metadata.user_email == driven.identity.email, f"user_email={breakdown.metadata.user_email!r}"
+
+    @pytest.mark.covers(
+        "quota_management.spend_tracking.key_attribution.health_rows_keep_service_account",
+        exercised_on=["chat_completions"],
+    )
+    def test_health_check_rows_keep_the_service_account_key(self, client: SpendClient) -> None:
+        started_at: Final = datetime.now(timezone.utc)
+        probe: Final = client.health(CHAT_MODEL)
+        assert probe.healthy, f"/health?model={CHAT_MODEL} answered {probe.status_code}: {probe.body[:300]}"
+        rows: Final = _health_rows_since(client, started_at)
+        assert rows, f"/health?model={CHAT_MODEL} wrote no {HEALTH_SERVICE_ACCOUNT}-tagged spend row"
+        rehashed: Final = [(row.request_id, row.api_key) for row in rows if row.api_key != HEALTH_SERVICE_ACCOUNT]
+        assert not rehashed, f"health-check rows keyed by something other than {HEALTH_SERVICE_ACCOUNT!r}: {rehashed}"
+
+    @pytest.mark.covers(
+        "quota_management.spend_tracking.key_attribution.retrieve_batch_cost_joins_retrieving_key",
+        exercised_on=["batches"],
+    )
+    def test_terminal_batch_cost_row_joins_the_retrieving_key(self, client: SpendClient, driven: DrivenKey) -> None:
+        provider_batch_id: Final = _provider_batch_id(_driven_batch_id(driven))
+        fetched: Final = _await_terminal_batch(client, driven.identity.key, provider_batch_id)
+        assert fetched.status == "failed", (
+            f"endpoint-mismatched batch {provider_batch_id} is {fetched.status!r} after "
+            f"{FAILED_BATCH_POLL_SECONDS:.0f}s, so its terminal cost row cannot be asserted"
+        )
+        cost_request_id: Final = f"{provider_batch_id}_batch_cost"
+        rows: Final = client.proxy.poll_logs_for_request_id(cost_request_id)
+        assert rows, f"retrieving failed batch {provider_batch_id} wrote no cost row under {cost_request_id}"
+        call_types: Final = tuple(sorted({row.call_type or "" for row in rows}))
+        assert call_types == ("aretrieve_batch",), f"cost rows under {cost_request_id} carry call types {call_types}"
+        unjoined: Final = [
+            (row.call_type, row.api_key, row.metadata.user_api_key_alias if row.metadata else None)
+            for row in rows
+            if row.api_key != driven.identity.token
+            or row.metadata is None
+            or row.metadata.user_api_key_alias != driven.identity.alias
+        ]
+        assert not unjoined, (
+            f"batch cost rows that do not join the retrieving key's token {driven.identity.token} "
+            f"with alias {driven.identity.alias!r}: {unjoined}"
+        )
diff --git a/tests/e2e/router/test_auto_router_regressions_e2e.py b/tests/e2e/router/test_auto_router_regressions_e2e.py
index 188db2a8eb5..374badcf5fc 100644
--- a/tests/e2e/router/test_auto_router_regressions_e2e.py
+++ b/tests/e2e/router/test_auto_router_regressions_e2e.py
@@ -41,6 +41,7 @@ which stores either the registered alias or the provider-prefixed form.
 import json
 import os
 from collections.abc import Iterator
+from contextlib import ExitStack
 from dataclasses import dataclass
 from typing import Final
 
@@ -120,19 +121,10 @@ class ResponsesApiResponse(BaseModel):
 
 
 @dataclass(frozen=True, slots=True)
-class TagSplitDeployments:
-    """Scenario A mirrors the customer-shaped config from GitHub issue #36619:
-    plain deployment registered first, tier deployment and marker both tagged.
-    Scenario B flips both axes for GitHub issue #36621: marker registered first
-    and its tier deployment left untagged, so routing depends neither on
-    registration order nor on tier deployments carrying tags."""
-
-    tag_a: str
-    shared_a: str
-    tier_a: str
-    tag_b: str
-    shared_b: str
-    tier_b: str
+class TagSplitDeployment:
+    tag: str
+    shared: str
+    tier: str
 
 
 @dataclass(frozen=True, slots=True)
@@ -173,9 +165,7 @@ def _uniform_tier_config(tier_model: str) -> dict[str, object]:
     }
 
 
-def _key_for(
-    proxy: ProxyClient, resources: ResourceManager, models: list[str], tag_filtering: bool = False
-) -> str:
+def _key_for(proxy: ProxyClient, resources: ResourceManager, models: list[str], tag_filtering: bool = False) -> str:
     key: Final = proxy.generate_key(
         KeyGenerateBody(
             models=models,
@@ -211,46 +201,61 @@ def _assert_served_only_by(rows: list[SpendLogRow], allowed: frozenset[str], con
     )
 
 
-@pytest.fixture(scope="module")
-def split(proxy: ProxyClient) -> Iterator[TagSplitDeployments]:
+@pytest.fixture(scope="class")
+def router_stack() -> Iterator[ExitStack]:
+    with ExitStack() as stack:
+        yield stack
+
+
+def _register_models(
+    proxy: ProxyClient, stack: ExitStack, registrations: tuple[tuple[str, LiteLLMParamsBody], ...]
+) -> None:
+    for name, params in registrations:
+        stack.callback(proxy.delete_model, proxy.create_model(name, params))
+
+
+def _tag_split(proxy: ProxyClient, stack: ExitStack, *, marker_first: bool) -> TagSplitDeployment:
     marker: Final = unique_marker()
-    deployments: Final = TagSplitDeployments(
-        tag_a=f"e2e-split-a-{marker}",
-        shared_a=f"e2e-autoroute-a-{marker}",
-        tier_a=f"e2e-tier-a-{marker}",
-        tag_b=f"e2e-split-b-{marker}",
-        shared_b=f"e2e-autoroute-b-{marker}",
-        tier_b=f"e2e-tier-b-{marker}",
+    named: Final = TagSplitDeployment(
+        tag=f"e2e-split-{marker}",
+        shared=f"e2e-autoroute-{marker}",
+        tier=f"e2e-tier-{marker}",
     )
     anthropic_key: Final = _provider_key("ANTHROPIC_API_KEY")
-    marker_params_a: Final = LiteLLMParamsBody(
-        model="auto_router/complexity_router",
-        complexity_router_config=_uniform_tier_config(deployments.tier_a),
-        tags=[deployments.tag_a],
+    marker_registration: Final = (
+        named.shared,
+        LiteLLMParamsBody(
+            model="auto_router/complexity_router",
+            complexity_router_config=_uniform_tier_config(named.tier),
+            tags=[named.tag],
+        ),
     )
-    marker_params_b: Final = LiteLLMParamsBody(
-        model="auto_router/complexity_router",
-        complexity_router_config=_uniform_tier_config(deployments.tier_b),
-        tags=[deployments.tag_b],
+    tier_registration: Final = (
+        named.tier,
+        LiteLLMParamsBody(model=CHEAP_MODEL, api_key=anthropic_key, tags=None if marker_first else [named.tag]),
     )
-    registrations: Final[tuple[tuple[str, LiteLLMParamsBody], ...]] = (
-        (deployments.shared_a, LiteLLMParamsBody(model=PLAIN_MODEL, api_key=anthropic_key)),
-        (deployments.tier_a, LiteLLMParamsBody(model=CHEAP_MODEL, api_key=anthropic_key, tags=[deployments.tag_a])),
-        (deployments.shared_a, marker_params_a),
-        (deployments.shared_b, marker_params_b),
-        (deployments.tier_b, LiteLLMParamsBody(model=CHEAP_MODEL, api_key=anthropic_key)),
-        (deployments.shared_b, LiteLLMParamsBody(model=PLAIN_MODEL, api_key=anthropic_key)),
+    plain_registration: Final = (named.shared, LiteLLMParamsBody(model=PLAIN_MODEL, api_key=anthropic_key))
+    registrations: Final = (
+        (marker_registration, tier_registration, plain_registration)
+        if marker_first
+        else (plain_registration, tier_registration, marker_registration)
     )
-    created: Final = tuple(proxy.create_model(name, params) for name, params in registrations)
-    try:
-        yield deployments
-    finally:
-        for model_id in created:
-            proxy.delete_model(model_id)
+    _register_models(proxy, stack, registrations)
+    return named
 
 
-@pytest.fixture(scope="module")
-def zero_priced_alias(proxy: ProxyClient) -> Iterator[ZeroPricedAlias]:
+@pytest.fixture(scope="class")
+def plain_first_split(proxy: ProxyClient, router_stack: ExitStack) -> TagSplitDeployment:
+    return _tag_split(proxy, router_stack, marker_first=False)
+
+
+@pytest.fixture(scope="class")
+def marker_first_split(proxy: ProxyClient, router_stack: ExitStack) -> TagSplitDeployment:
+    return _tag_split(proxy, router_stack, marker_first=True)
+
+
+@pytest.fixture(scope="class")
+def zero_priced_alias(proxy: ProxyClient, router_stack: ExitStack) -> ZeroPricedAlias:
     marker: Final = unique_marker()
     named: Final = ZeroPricedAlias(alias=f"e2e-priced-alias-{marker}", tier=f"e2e-priced-tier-{marker}")
     alias_params: Final = LiteLLMParamsBody(
@@ -263,16 +268,12 @@ def zero_priced_alias(proxy: ProxyClient) -> Iterator[ZeroPricedAlias]:
         (named.tier, LiteLLMParamsBody(model=CHEAP_MODEL, api_key=_provider_key("ANTHROPIC_API_KEY"))),
         (named.alias, alias_params),
     )
-    created: Final = tuple(proxy.create_model(name, params) for name, params in registrations)
-    try:
-        yield named
-    finally:
-        for model_id in created:
-            proxy.delete_model(model_id)
+    _register_models(proxy, router_stack, registrations)
+    return named
 
 
-@pytest.fixture(scope="module")
-def heuristic_split(proxy: ProxyClient) -> Iterator[HeuristicSplit]:
+@pytest.fixture(scope="class")
+def heuristic_split(proxy: ProxyClient, router_stack: ExitStack) -> HeuristicSplit:
     marker: Final = unique_marker()
     named: Final = HeuristicSplit(
         alias=f"e2e-heuristic-router-{marker}",
@@ -289,16 +290,12 @@ def heuristic_split(proxy: ProxyClient) -> Iterator[HeuristicSplit]:
         (named.strong, LiteLLMParamsBody(model=STRONG_MODEL, api_key=_provider_key("OPENAI_API_KEY"))),
         (named.alias, LiteLLMParamsBody(model="auto_router/complexity_router", complexity_router_config=config)),
     )
-    created: Final = tuple(proxy.create_model(name, params) for name, params in registrations)
-    try:
-        yield named
-    finally:
-        for model_id in created:
-            proxy.delete_model(model_id)
+    _register_models(proxy, router_stack, registrations)
+    return named
 
 
-@pytest.fixture(scope="module")
-def semantic_auto_router(proxy: ProxyClient) -> Iterator[SemanticAutoRouter]:
+@pytest.fixture(scope="class")
+def semantic_auto_router(proxy: ProxyClient, router_stack: ExitStack) -> SemanticAutoRouter:
     marker: Final = unique_marker()
     named: Final = SemanticAutoRouter(
         marker=f"e2e-semantic-router-{marker}",
@@ -321,16 +318,12 @@ def semantic_auto_router(proxy: ProxyClient) -> Iterator[SemanticAutoRouter]:
         (named.fallback, LiteLLMParamsBody(model=PLAIN_MODEL, api_key=_provider_key("ANTHROPIC_API_KEY"))),
         (named.marker, marker_params),
     )
-    created: Final = tuple(proxy.create_model(name, params) for name, params in registrations)
-    try:
-        yield named
-    finally:
-        for model_id in created:
-            proxy.delete_model(model_id)
+    _register_models(proxy, router_stack, registrations)
+    return named
 
 
-@pytest.fixture(scope="module")
-def credentialed_alias(proxy: ProxyClient) -> Iterator[CredentialedAlias]:
+@pytest.fixture(scope="class")
+def credentialed_alias(proxy: ProxyClient, router_stack: ExitStack) -> CredentialedAlias:
     marker: Final = unique_marker()
     named: Final = CredentialedAlias(alias=f"e2e-cred-alias-{marker}", tier=f"e2e-cred-tier-{marker}")
     alias_params: Final = LiteLLMParamsBody(
@@ -342,104 +335,110 @@ def credentialed_alias(proxy: ProxyClient) -> Iterator[CredentialedAlias]:
         (named.tier, LiteLLMParamsBody(model=CHEAP_MODEL, api_key=_provider_key("ANTHROPIC_API_KEY"))),
         (named.alias, alias_params),
     )
-    created: Final = tuple(proxy.create_model(name, params) for name, params in registrations)
-    try:
-        yield named
-    finally:
-        for model_id in created:
-            proxy.delete_model(model_id)
+    _register_models(proxy, router_stack, registrations)
+    return named
 
 
 class TestTagSplitRouting:
     @pytest.mark.covers("reliability.routing.tagged_marker.request_tag_selects_marker")
     def test_body_tagged_chat_routes_through_the_marker_to_its_tier(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, plain_first_split: TagSplitDeployment
     ) -> None:
         """Pins GitHub issue #36619: with tag filtering on, a chat request whose
         body metadata tags match the tagged marker under a shared model name is
         answered by the marker's tier deployment, not by the plain deployment
         that was registered under the name first."""
-        key: Final = _key_for(proxy, resources, [split.shared_a, split.tier_a], tag_filtering=True)
-        chat: Final = unwrap(proxy.chat(key, _hello_chat_body(split.shared_a, tags=[split.tag_a])))
+        key: Final = _key_for(proxy, resources, [plain_first_split.shared, plain_first_split.tier], tag_filtering=True)
+        chat: Final = unwrap(proxy.chat(key, _hello_chat_body(plain_first_split.shared, tags=[plain_first_split.tag])))
         assert chat.choices, "tagged chat through the shared name returned no choices"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, CHEAP_SERVED | {split.tier_a}, "body-tagged chat on the shared name")
+        _assert_served_only_by(rows, CHEAP_SERVED | {plain_first_split.tier}, "body-tagged chat on the shared name")
 
     @pytest.mark.covers("reliability.routing.tagged_marker.untagged_request_served_by_plain_deployment")
     def test_untagged_chat_is_always_served_by_the_plain_deployment(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, plain_first_split: TagSplitDeployment
     ) -> None:
         """Pins GitHub issue #36620: untagged chat requests to the shared name
         succeed on every call and are all served by the plain deployment; the
         tagged marker never captures them, so no intermittent auto-router
         errors and no tier hijacking."""
-        key: Final = _key_for(proxy, resources, [split.shared_a, split.tier_a], tag_filtering=True)
+        key: Final = _key_for(proxy, resources, [plain_first_split.shared, plain_first_split.tier], tag_filtering=True)
         for _ in range(5):
-            chat = unwrap(proxy.chat(key, _hello_chat_body(split.shared_a)))
+            chat = unwrap(proxy.chat(key, _hello_chat_body(plain_first_split.shared)))
             assert chat.choices, "untagged chat through the shared name returned no choices"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=5)
-        _assert_served_only_by(rows, PLAIN_SERVED | {split.shared_a}, "untagged chat on the shared name")
+        _assert_served_only_by(rows, PLAIN_SERVED | {plain_first_split.shared}, "untagged chat on the shared name")
 
     @pytest.mark.covers("reliability.routing.tagged_marker.untagged_request_served_by_plain_deployment")
     def test_untagged_messages_is_served_by_the_plain_deployment(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, plain_first_split: TagSplitDeployment
     ) -> None:
         """Pins GitHub issue #36620 on the /v1/messages surface: an untagged
         Anthropic-native request to the shared name is served by the plain
         deployment, not captured by the tagged marker."""
-        key: Final = _key_for(proxy, resources, [split.shared_a, split.tier_a], tag_filtering=True)
-        answer: Final = unwrap(proxy.messages(key, _hello_messages_body(split.shared_a)))
+        key: Final = _key_for(proxy, resources, [plain_first_split.shared, plain_first_split.tier], tag_filtering=True)
+        answer: Final = unwrap(proxy.messages(key, _hello_messages_body(plain_first_split.shared)))
         assert answer.content or answer.choices, "untagged /v1/messages returned neither content nor choices"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, PLAIN_SERVED | {split.shared_a}, "untagged /v1/messages on the shared name")
+        _assert_served_only_by(
+            rows, PLAIN_SERVED | {plain_first_split.shared}, "untagged /v1/messages on the shared name"
+        )
 
 
 class TestUntaggedTierDeployments:
     @pytest.mark.covers("reliability.routing.tagged_marker.header_tag_selects_marker")
     def test_header_tagged_messages_routes_through_the_marker_to_an_untagged_tier(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, marker_first_split: TagSplitDeployment
     ) -> None:
         """Pins GitHub issue #36621: a /v1/messages request tagged only via the
         x-litellm-tags header selects the tagged marker, and the rewrite still
         lands on the tier deployment even though that deployment carries no
         tags, because the marker consumed the routing tags."""
-        key: Final = _key_for(proxy, resources, [split.shared_b, split.tier_b], tag_filtering=True)
-        headers: Final = TaggedAnthropicHeaders(authorization=f"Bearer {key}", x_litellm_tags=split.tag_b)
+        key: Final = _key_for(
+            proxy, resources, [marker_first_split.shared, marker_first_split.tier], tag_filtering=True
+        )
+        headers: Final = TaggedAnthropicHeaders(authorization=f"Bearer {key}", x_litellm_tags=marker_first_split.tag)
         answer: Final = unwrap(
             proxy.transport.post(
                 "/v1/messages",
                 headers=headers,
-                json=_hello_messages_body(split.shared_b),
+                json=_hello_messages_body(marker_first_split.shared),
                 response_type=AnthropicMessagesResponse,
             )
         )
         assert answer.content or answer.choices, "header-tagged /v1/messages returned neither content nor choices"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, CHEAP_SERVED | {split.tier_b}, "header-tagged /v1/messages on the shared name")
+        _assert_served_only_by(
+            rows, CHEAP_SERVED | {marker_first_split.tier}, "header-tagged /v1/messages on the shared name"
+        )
 
     @pytest.mark.covers("reliability.routing.tagged_marker.untagged_tier_deployments_still_served")
     def test_body_tagged_chat_reaches_the_untagged_tier_after_marker_rewrite(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, marker_first_split: TagSplitDeployment
     ) -> None:
         """Pins the tag-consumption half of GitHub issue #36621: after the
         tagged marker rewrites the request to its tier model, the consumed
         routing tags no longer constrain deployment selection, so the untagged
         tier deployment serves the request instead of a strict-tag denial."""
-        key: Final = _key_for(proxy, resources, [split.shared_b, split.tier_b], tag_filtering=True)
-        chat: Final = unwrap(proxy.chat(key, _hello_chat_body(split.shared_b, tags=[split.tag_b])))
+        key: Final = _key_for(
+            proxy, resources, [marker_first_split.shared, marker_first_split.tier], tag_filtering=True
+        )
+        chat: Final = unwrap(
+            proxy.chat(key, _hello_chat_body(marker_first_split.shared, tags=[marker_first_split.tag]))
+        )
         assert chat.choices, "body-tagged chat through the marker-first shared name returned no choices"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, CHEAP_SERVED | {split.tier_b}, "body-tagged chat with untagged tier")
+        _assert_served_only_by(rows, CHEAP_SERVED | {marker_first_split.tier}, "body-tagged chat with untagged tier")
 
     @pytest.mark.covers("reliability.routing.tagged_marker.tag_semantics_stay_strict")
     def test_tagged_call_straight_at_an_untagged_deployment_stays_denied(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, marker_first_split: TagSplitDeployment
     ) -> None:
         """The tag-consumption fix must not loosen strict tag semantics: a
         tagged request aimed directly at an untagged deployment (no marker
         involved) is still rejected with the 401 tags-configuration error."""
-        key: Final = _key_for(proxy, resources, [split.tier_b], tag_filtering=True)
-        result: Final = proxy.chat(key, _hello_chat_body(split.tier_b, tags=[split.tag_b]))
+        key: Final = _key_for(proxy, resources, [marker_first_split.tier], tag_filtering=True)
+        result: Final = proxy.chat(key, _hello_chat_body(marker_first_split.tier, tags=[marker_first_split.tag]))
         assert isinstance(result, UnauthorizedError), (
             f"expected the tagged direct call to an untagged deployment to be denied with 401, got {result}"
         )
@@ -451,37 +450,39 @@ class TestUntaggedTierDeployments:
 class TestResponsesApiTagRouting:
     @pytest.mark.covers("reliability.routing.tagged_marker.responses_input_routes_through_marker")
     def test_header_tagged_responses_with_string_input_routes_to_the_tier(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, plain_first_split: TagSplitDeployment
     ) -> None:
         """Pins the /v1/responses surface of the tag split (GitHub issues
         #36620/#36621): a /v1/responses request with string input, tagged via
         the x-litellm-tags header, succeeds and routes through the tagged
         marker to its tier."""
-        key: Final = _key_for(proxy, resources, [split.shared_a, split.tier_a], tag_filtering=True)
-        headers: Final = TaggedAuthHeaders(authorization=f"Bearer {key}", x_litellm_tags=split.tag_a)
+        key: Final = _key_for(proxy, resources, [plain_first_split.shared, plain_first_split.tier], tag_filtering=True)
+        headers: Final = TaggedAuthHeaders(authorization=f"Bearer {key}", x_litellm_tags=plain_first_split.tag)
         body: Final = ResponsesBody(
-            model=split.shared_a, input=f"say hello {unique_marker()}", max_output_tokens=64
+            model=plain_first_split.shared, input=f"say hello {unique_marker()}", max_output_tokens=64
         )
         answer: Final = unwrap(
             proxy.transport.post("/v1/responses", headers=headers, json=body, response_type=ResponsesApiResponse)
         )
         assert answer.id, "header-tagged /v1/responses returned no response id"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, CHEAP_SERVED | {split.tier_a}, "header-tagged /v1/responses string input")
+        _assert_served_only_by(
+            rows, CHEAP_SERVED | {plain_first_split.tier}, "header-tagged /v1/responses string input"
+        )
 
     @pytest.mark.covers("reliability.routing.tagged_marker.responses_input_routes_through_marker")
     def test_body_tagged_responses_with_list_input_routes_to_the_tier(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, plain_first_split: TagSplitDeployment
     ) -> None:
         """Pins the body-tag and list-input combination of the same split:
         /v1/responses with litellm_metadata.tags and structured input items
         routes through the tagged marker to its tier."""
-        key: Final = _key_for(proxy, resources, [split.shared_a, split.tier_a], tag_filtering=True)
+        key: Final = _key_for(proxy, resources, [plain_first_split.shared, plain_first_split.tier], tag_filtering=True)
         body: Final = ResponsesBody(
-            model=split.shared_a,
+            model=plain_first_split.shared,
             input=[ResponsesInputItem(role="user", content=f"say hello {unique_marker()}")],
             max_output_tokens=64,
-            litellm_metadata=ResponsesTagMetadata(tags=[split.tag_a]),
+            litellm_metadata=ResponsesTagMetadata(tags=[plain_first_split.tag]),
         )
         answer: Final = unwrap(
             proxy.transport.post(
@@ -493,18 +494,18 @@ class TestResponsesApiTagRouting:
         )
         assert answer.id, "body-tagged /v1/responses returned no response id"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, CHEAP_SERVED | {split.tier_a}, "body-tagged /v1/responses list input")
+        _assert_served_only_by(rows, CHEAP_SERVED | {plain_first_split.tier}, "body-tagged /v1/responses list input")
 
     @pytest.mark.covers("reliability.routing.tagged_marker.untagged_request_served_by_plain_deployment")
     def test_untagged_responses_is_served_by_the_plain_deployment(
-        self, proxy: ProxyClient, resources: ResourceManager, split: TagSplitDeployments
+        self, proxy: ProxyClient, resources: ResourceManager, plain_first_split: TagSplitDeployment
     ) -> None:
         """Pins the untagged half of the /v1/responses tag split: an untagged
         request to the shared name is served by the plain deployment, matching
         the chat and messages surfaces."""
-        key: Final = _key_for(proxy, resources, [split.shared_a, split.tier_a], tag_filtering=True)
+        key: Final = _key_for(proxy, resources, [plain_first_split.shared, plain_first_split.tier], tag_filtering=True)
         body: Final = ResponsesBody(
-            model=split.shared_a, input=f"say hello {unique_marker()}", max_output_tokens=64
+            model=plain_first_split.shared, input=f"say hello {unique_marker()}", max_output_tokens=64
         )
         answer: Final = unwrap(
             proxy.transport.post(
@@ -516,7 +517,9 @@ class TestResponsesApiTagRouting:
         )
         assert answer.id, "untagged /v1/responses returned no response id"
         rows: Final = proxy.poll_logs_for_key(key, min_rows=1)
-        _assert_served_only_by(rows, PLAIN_SERVED | {split.shared_a}, "untagged /v1/responses on the shared name")
+        _assert_served_only_by(
+            rows, PLAIN_SERVED | {plain_first_split.shared}, "untagged /v1/responses on the shared name"
+        )
 
 
 class TestStrategyAliasPricing:
@@ -551,9 +554,7 @@ class TestComplexityHeuristicScope:
         while the accompanying ~2KB agent system prompt is packed with enough
         reasoning and complexity keywords that scoring the combined text lands
         in REASONING; only ask-only scoring keeps this on the cheap tier."""
-        key: Final = _key_for(
-            proxy, resources, [heuristic_split.alias, heuristic_split.cheap, heuristic_split.strong]
-        )
+        key: Final = _key_for(proxy, resources, [heuristic_split.alias, heuristic_split.cheap, heuristic_split.strong])
         body: Final = ChatBody(
             model=heuristic_split.alias,
             messages=[
diff --git a/tests/e2e/test_e2e_http.py b/tests/e2e/test_e2e_http.py
index 66841725d1d..81cd6c8d3d1 100644
--- a/tests/e2e/test_e2e_http.py
+++ b/tests/e2e/test_e2e_http.py
@@ -13,13 +13,24 @@ monkeypatches anything.
 from __future__ import annotations
 
 from collections.abc import Callable, Iterator, Mapping, Sequence
-from dataclasses import dataclass, field
+from dataclasses import dataclass
 from types import MappingProxyType
 from typing import Final
 
 import pytest
-
-from e2e_http import RETRY_ATTEMPTS, TRANSIENT_STATUSES, request_with_retry, streaming_outcome
+from e2e_http import (
+    RETRY_ATTEMPTS,
+    TRANSIENT_STATUSES,
+    NoBody,
+    PartialBody,
+    Success,
+    ValidationError,
+    classify,
+    request_with_retry,
+    streaming_outcome,
+    wire_body,
+)
+from pydantic import BaseModel, TypeAdapter
 
 
 @dataclass
@@ -33,10 +44,10 @@ class FakeResponse:
 
 @dataclass
 class SleepRecorder:
-    delays: list[float] = field(default_factory=list)
+    delays: tuple[float, ...] = ()
 
     def __call__(self, seconds: float) -> None:
-        self.delays.append(seconds)
+        self.delays += (seconds,)
 
 
 def _issue_from(responses: Sequence[FakeResponse]) -> Callable[[], FakeResponse]:
@@ -55,7 +66,7 @@ class TestTransientRetryPolicy:
         sleep = SleepRecorder()
         result = request_with_retry(_issue_from(responses), sleep=sleep)
         assert result is responses[0]
-        assert sleep.delays == []
+        assert sleep.delays == ()
         assert responses[0].close_calls == 0
 
     def test_429_is_never_retried(self) -> None:
@@ -63,7 +74,7 @@ class TestTransientRetryPolicy:
         sleep = SleepRecorder()
         result = request_with_retry(_issue_from(responses), sleep=sleep)
         assert result is responses[0]
-        assert sleep.delays == []
+        assert sleep.delays == ()
         assert responses[0].close_calls == 0
 
     def test_overloaded_529_retries_with_backoff_then_returns_the_success(self) -> None:
@@ -71,7 +82,7 @@ class TestTransientRetryPolicy:
         sleep = SleepRecorder()
         result = request_with_retry(_issue_from(responses), sleep=sleep)
         assert result is responses[1]
-        assert sleep.delays == [0.5]
+        assert sleep.delays == (0.5,)
         assert responses[0].close_calls == 1
         assert responses[1].close_calls == 0
 
@@ -80,7 +91,7 @@ class TestTransientRetryPolicy:
         sleep = SleepRecorder()
         result = request_with_retry(_issue_from(responses), sleep=sleep)
         assert result is responses[RETRY_ATTEMPTS - 1]
-        assert sleep.delays == [0.5, 1.0]
+        assert sleep.delays == (0.5, 1.0)
         assert [r.close_calls for r in responses] == [1, 1, 0, 0]
 
 
@@ -134,3 +145,65 @@ class TestStreamEventArrivals:
         assert result.stream_events == []
         assert result.stream_event_arrivals == []
         assert result.body == "bad request"
+
+
+class _ServerUpdate(PartialBody):
+    server_id: str
+    alias: str | None = None
+    description: str | None = None
+
+
+class _ServerCreate(BaseModel):
+    alias: str
+    description: str | None = None
+
+
+class TestWireBody:
+    """A partial-update body must put exactly the caller's choice on the wire: an
+    omitted field stays off it so the route keeps the stored value, and an explicit
+    None goes out as JSON null so the route clears it. Plain bodies keep dropping
+    None, which is what every create route expects."""
+
+    def test_partial_body_omits_unset_fields_and_sends_explicit_none_as_null(self) -> None:
+        assert wire_body(_ServerUpdate(server_id="s1", description=None)) == {"server_id": "s1", "description": None}
+        assert wire_body(_ServerUpdate(server_id="s1", alias="renamed")) == {"server_id": "s1", "alias": "renamed"}
+
+    def test_plain_body_drops_none_fields(self) -> None:
+        assert wire_body(_ServerCreate(alias="a", description=None)) == {"alias": "a"}
+
+
+_JSON: Final[TypeAdapter[object]] = TypeAdapter(object)
+
+
+@dataclass
+class FakeJsonResponse:
+    """The `classify` view of a response: a status, the raw body bytes, and the
+    parse that would raise on an empty one."""
+
+    status_code: int
+    content: bytes
+
+    @property
+    def ok(self) -> bool:
+        return self.status_code < 400
+
+    @property
+    def text(self) -> str:
+        return self.content.decode()
+
+    def json(self) -> object:
+        return _JSON.validate_json(self.content)
+
+
+class TestClassifyEmptyBody:
+    """A delete that answers 202 with no body is a success, not a parse failure:
+    the MCP server and toolset delete routes both answer that way, and reading it
+    as a failure would hide a delete that did not happen behind one that did."""
+
+    def test_empty_2xx_body_is_a_success(self) -> None:
+        result: Final = classify(FakeJsonResponse(status_code=202, content=b""), NoBody)
+        assert isinstance(result, Success) and result.status_code == 202
+
+    def test_body_that_is_not_json_is_still_a_validation_failure(self) -> None:
+        result: Final = classify(FakeJsonResponse(status_code=200, content=b"<html/>"), NoBody)
+        assert isinstance(result, ValidationError)
diff --git a/tests/e2e/test_proxy_client.py b/tests/e2e/test_proxy_client.py
index 2caac58333f..3b84a47e3cc 100644
--- a/tests/e2e/test_proxy_client.py
+++ b/tests/e2e/test_proxy_client.py
@@ -15,28 +15,35 @@ from collections.abc import Iterable, Mapping
 from dataclasses import dataclass
 from itertools import chain, repeat
 from types import MappingProxyType
-from typing import Final
+from typing import Final, cast
 
 import pytest
-
 from e2e_config import parse_replica_urls
 from e2e_http import Result, Success
 from models import KeyInfo, KeyInfoResponse, ModelListEntry, ModelsListResponse
 from proxy_client import (
-    Poller,
     ConvergeOutcome,
     Converged,
+    EverywhereConverged,
     ModelsPoller,
+    NeverConvergedOn,
     NotConverged,
     NotServableOn,
+    Poller,
+    ProxyClient,
+    ReplicaRead,
     Servable,
     await_converged_everywhere,
+    await_everywhere,
     await_servable_everywhere,
-    first_lagging_replica,
+    build_proxy_client,
     converge_timeout_message,
+    first_lagging_replica,
 )
+from transport import Transport
 
 MODEL: Final = "gpt-under-test"
+_NO_TRANSPORTS: Final = cast(Transport, None)
 TIMEOUT: Final = 10.0
 INTERVAL: Final = 2.0
 RPM_BEFORE_UPDATE: Final = 100
@@ -187,3 +194,83 @@ class TestParseReplicaUrls:
 
     def test_falls_back_to_the_data_plane_address_when_unset(self) -> None:
         assert parse_replica_urls("", "http://lb") == ("http://lb",)
+
+
+def _answers(answers: Iterable[str]) -> ReplicaRead[str]:
+    it: Final = iter(answers)
+    return lambda _timeout: next(it)
+
+
+def _await_everywhere(reads: Mapping[str, ReplicaRead[str]]) -> EverywhereConverged[str] | NeverConvergedOn[str]:
+    clock: Final = FakeClock()
+    return await_everywhere(
+        reads,
+        settled=lambda answer: answer == "renamed",
+        timeout=TIMEOUT,
+        interval=INTERVAL,
+        request_timeout=5.0,
+        now=clock.now,
+        sleep=clock.sleep,
+    )
+
+
+class TestAwaitEverywhere:
+    def test_waits_for_the_lagging_replica_and_returns_every_settled_answer(self) -> None:
+        reads: Final = {
+            "gateway-1": _answers(repeat("renamed")),
+            "gateway-2": _answers(chain(repeat("stale", 2), repeat("renamed"))),
+        }
+        outcome: Final = _await_everywhere(reads)
+        assert isinstance(outcome, EverywhereConverged)
+        assert dict(outcome.answers) == {"gateway-1": "renamed", "gateway-2": "renamed"}
+
+    def test_names_the_replica_that_never_converges_with_what_it_last_served(self) -> None:
+        reads: Final = {
+            "gateway-1": _answers(repeat("renamed")),
+            "gateway-2": _answers(repeat("stale")),
+        }
+        assert _await_everywhere(reads) == NeverConvergedOn(replica="gateway-2", last="stale")
+
+    def test_polls_until_the_deadline_before_giving_up(self) -> None:
+        lagging: Final = chain(repeat("stale", int(TIMEOUT / INTERVAL)), repeat("renamed"))
+        outcome: Final = _await_everywhere({"gateway-1": _answers(lagging)})
+        assert isinstance(outcome, EverywhereConverged), outcome
+
+
+class TestReplicasFor:
+    def test_split_deployment_reads_management_routes_back_from_the_control_plane(self) -> None:
+        client: Final = build_proxy_client(
+            base_url="http://lb",
+            control_plane_base_url="http://backend",
+            replica_urls=("http://gateway-1", "http://gateway-2"),
+        )
+        assert set(client.replicas_for("/key/info")) == {"http://backend"}
+        assert set(client.replicas_for("/v1/models")) == {"http://gateway-1", "http://gateway-2"}
+
+    def test_monolith_reads_management_routes_back_from_every_replica(self) -> None:
+        client: Final = build_proxy_client(
+            base_url="http://lb",
+            control_plane_base_url="http://lb",
+            replica_urls=("http://pod-1", "http://pod-2"),
+        )
+        assert set(client.replicas_for("/key/info")) == {"http://pod-1", "http://pod-2"}
+
+    def test_mcp_admin_routes_read_back_from_every_data_plane_replica(self) -> None:
+        """/v1/mcp/* is a lazily mounted feature, so a data-plane replica serves it
+        too and answers from its own in-memory registry. Routing it to the control
+        plane would leave every replica but that one unproven, and would move the
+        tools/list barrier in mcp_client off the plane that serves tools/list."""
+        client: Final = build_proxy_client(
+            base_url="http://lb",
+            control_plane_base_url="http://backend",
+            replica_urls=("http://gateway-1", "http://gateway-2"),
+        )
+        assert set(client.replicas_for("/v1/mcp/server/abc")) == {"http://gateway-1", "http://gateway-2"}
+        assert set(client.replicas_for("/v1/mcp/toolset/abc")) == {"http://gateway-1", "http://gateway-2"}
+
+    def test_a_route_no_replica_serves_is_refused_rather_than_read_back_vacuously(self) -> None:
+        """A read-back over zero replicas would satisfy every predicate and assert
+        nothing, so asking for one fails instead of passing silently."""
+        client: Final = ProxyClient(transport=_NO_TRANSPORTS, replicas={}, control_replicas={})
+        with pytest.raises(AssertionError, match="no replica is configured"):
+            _ = client.replicas_for("/v1/models")
diff --git a/tests/e2e/ui/helpers/navigation.ts b/tests/e2e/ui/helpers/navigation.ts
index 4a7c4e7baa9..e0e7b4da396 100644
--- a/tests/e2e/ui/helpers/navigation.ts
+++ b/tests/e2e/ui/helpers/navigation.ts
@@ -73,3 +73,13 @@ export async function clickTeamId(page: PlaywrightPage, teamId: string): Promise
   await cell.click();
   await expect(page.getByText("Back to Teams")).toBeVisible({ timeout: 10_000 });
 }
+
+export async function openKeyDetail(page: PlaywrightPage, alias: string): Promise<void> {
+  await page.getByPlaceholder("Search by key alias or ID").fill(alias);
+  const row = page.getByRole("row").filter({ hasText: alias });
+  await expect(row, `key row "${alias}" never appeared on the Virtual Keys page`).toBeVisible({ timeout: 15_000 });
+  await row.getByRole("button", { name: alias }).click();
+  await expect(page.getByText("Back to Keys"), `key detail for "${alias}" never opened`).toBeVisible({
+    timeout: 15_000,
+  });
+}
diff --git a/tests/e2e/ui/helpers/traffic.ts b/tests/e2e/ui/helpers/traffic.ts
index 7f8417cdffb..cb68747b364 100644
--- a/tests/e2e/ui/helpers/traffic.ts
+++ b/tests/e2e/ui/helpers/traffic.ts
@@ -1,4 +1,4 @@
-import { APIRequestContext, expect } from "@playwright/test";
+import { APIRequestContext, APIResponse, expect } from "@playwright/test";
 
 /** Model names served by fixtures/config.yml, both backed by the mock LLM server. */
 export const CHAT_MODEL_A = "fake-openai-gpt-4";
@@ -15,6 +15,9 @@ export const masterKey = (): string => process.env.LITELLM_MASTER_KEY || "sk-123
 
 export const rootPath = (): string => process.env.SERVER_ROOT_PATH ?? "";
 
+/** Date.now() alone collides: `--repeat-each` starts its copies inside the same millisecond. */
+export const uniqueSuffix = (): string => `${Date.now()}-${Math.random().toString(36).slice(2, 8)}`;
+
 interface ChatOptions {
   model: string;
   prompt: string;
@@ -25,9 +28,8 @@ interface ChatOptions {
   traceId?: string;
 }
 
-/** POST /v1/chat/completions and return the completion id (the Logs Request ID). */
-export async function sendChatCompletion(request: APIRequestContext, opts: ChatOptions): Promise<string> {
-  const res = await request.post(`${rootPath()}/v1/chat/completions`, {
+const postChatCompletion = (request: APIRequestContext, opts: ChatOptions): Promise<APIResponse> =>
+  request.post(`${rootPath()}/v1/chat/completions`, {
     headers: {
       Authorization: `Bearer ${opts.apiKey ?? masterKey()}`,
       "Content-Type": "application/json",
@@ -39,12 +41,26 @@ export async function sendChatCompletion(request: APIRequestContext, opts: ChatO
       ...(opts.traceId ? { litellm_trace_id: opts.traceId } : {}),
     },
   });
+
+/** POST /v1/chat/completions and return the completion id (the Logs Request ID). */
+export async function sendChatCompletion(request: APIRequestContext, opts: ChatOptions): Promise<string> {
+  const res = await postChatCompletion(request, opts);
   expect(res.ok(), `chat completion for ${opts.model} failed (${res.status()}): ${await res.text()}`).toBe(true);
   const body = await res.json();
   expect(body.choices?.[0]?.message?.content).toContain(MOCK_RESPONSE_TEXT);
   return body.id as string;
 }
 
+export interface ChatAttempt {
+  status: number;
+  body: string;
+}
+
+export async function attemptChatCompletion(request: APIRequestContext, opts: ChatOptions): Promise<ChatAttempt> {
+  const res = await postChatCompletion(request, opts);
+  return { status: res.status(), body: await res.text() };
+}
+
 /** `key` is the sk- value to authenticate with; `token` is its hash, which spend aggregates are keyed by. */
 export async function createVirtualKey(
   request: APIRequestContext,
@@ -66,6 +82,33 @@ export async function createVirtualKey(
   };
 }
 
+export interface KeyInfo {
+  key_alias: string | null;
+  max_budget: number | null;
+  budget_duration: string | null;
+  budget_reset_at: string | null;
+  blocked: boolean | null;
+  models: string[];
+  team_id: string | null;
+}
+
+export async function readKeyInfo(request: APIRequestContext, token: string): Promise<KeyInfo> {
+  const res = await request.get(`${rootPath()}/key/info?key=${encodeURIComponent(token)}`, {
+    headers: { Authorization: `Bearer ${masterKey()}` },
+  });
+  expect(res.ok(), `GET /key/info for ${token} failed (${res.status()}): ${await res.text()}`).toBe(true);
+  const body = await res.json();
+  return body.info as KeyInfo;
+}
+
+export async function deleteVirtualKey(request: APIRequestContext, token: string): Promise<void> {
+  const res = await request.post(`${rootPath()}/key/delete`, {
+    headers: { Authorization: `Bearer ${masterKey()}`, "Content-Type": "application/json" },
+    data: { keys: [token] },
+  });
+  expect(res.ok(), `key delete for ${token} failed (${res.status()}): ${await res.text()}`).toBe(true);
+}
+
 /** Spend logs are flushed on a timer, so an assertion straight after a completion races the writer. */
 export async function waitForSpendLog(
   request: APIRequestContext,
diff --git a/tests/e2e/ui/tests/internal-user/internalUserKeyScope.spec.ts b/tests/e2e/ui/tests/internal-user/internalUserKeyScope.spec.ts
new file mode 100644
index 00000000000..f923841257a
--- /dev/null
+++ b/tests/e2e/ui/tests/internal-user/internalUserKeyScope.spec.ts
@@ -0,0 +1,208 @@
+import { test, expect, type APIRequestContext } from "@playwright/test";
+import { Page } from "../../fixtures/pages";
+import {
+  dismissFeedbackPopup,
+  navigateToPage,
+  openKeyDetail,
+} from "../../helpers/navigation";
+import {
+  CHAT_MODEL_A,
+  CHAT_MODEL_B,
+  MOCK_RESPONSE_TEXT,
+  attemptChatCompletion,
+  createVirtualKey,
+  deleteVirtualKey,
+  masterKey,
+  readKeyInfo,
+  rootPath,
+  uniqueSuffix,
+} from "../../helpers/traffic";
+
+const MEMBER_PASSWORD = "E2e-Team-Member-Pass-1!";
+
+interface CreatedTeam {
+  readonly team_id: string;
+}
+
+function assertCreatedTeam(body: unknown): asserts body is CreatedTeam {
+  expect(body, "/team/new returned no team_id").toMatchObject({
+    team_id: expect.any(String),
+  });
+}
+
+async function postAsMaster(
+  request: APIRequestContext,
+  path: string,
+  data: Record<string, unknown>,
+): Promise<unknown> {
+  const res = await request.post(`${rootPath()}${path}`, {
+    headers: {
+      Authorization: `Bearer ${masterKey()}`,
+      "Content-Type": "application/json",
+    },
+    data,
+  });
+  expect(
+    res.ok(),
+    `POST ${path} failed (${res.status()}): ${await res.text()}`,
+  ).toBe(true);
+  return res.json();
+}
+
+test.describe("Internal User - own team key model scope", () => {
+  test.use({ storageState: { cookies: [], origins: [] } });
+
+  test("a team member narrows their own key's models and the proxy enforces it", async ({
+    page,
+    request,
+  }) => {
+    const suffix = uniqueSuffix();
+    const email = `team-member-${suffix}@test.local`;
+    const userId = `e2e-key-scope-user-${suffix}`;
+    const alias = `e2e-key-scope-${suffix}`;
+
+    const team = await postAsMaster(request, "/team/new", {
+      team_alias: `E2E Key Scope ${suffix}`,
+      models: [CHAT_MODEL_A, CHAT_MODEL_B],
+      team_member_permissions: ["/key/generate", "/key/update", "/key/info"],
+    });
+    assertCreatedTeam(team);
+    const teamId = team.team_id;
+
+    try {
+      await postAsMaster(request, "/user/new", {
+        user_id: userId,
+        user_email: email,
+        user_role: "internal_user",
+        auto_create_key: false,
+      });
+      await postAsMaster(request, "/user/update", {
+        user_id: userId,
+        password: MEMBER_PASSWORD,
+      });
+      await postAsMaster(request, "/team/member_add", {
+        team_id: teamId,
+        member: { role: "user", user_id: userId },
+      });
+
+      const created = await createVirtualKey(request, {
+        key_alias: alias,
+        team_id: teamId,
+        user_id: userId,
+        models: [],
+      });
+
+      try {
+        await page.goto("/ui/login");
+        await page.getByPlaceholder("Enter your username").fill(email);
+        await page
+          .getByPlaceholder("Enter your password")
+          .fill(MEMBER_PASSWORD);
+        await page.getByRole("button", { name: "Login", exact: true }).click();
+        await expect(
+          page.locator("a", { hasText: "Virtual Keys" }),
+          `${email} never reached the dashboard`,
+        ).toBeVisible({ timeout: 30_000 });
+        await dismissFeedbackPopup(page);
+
+        await navigateToPage(page, Page.ApiKeys);
+        await openKeyDetail(page, alias);
+
+        await page.getByRole("tab", { name: "Settings" }).click();
+        await page.getByRole("button", { name: "Edit Settings" }).click();
+
+        await page.getByRole("combobox", { name: "Select models" }).click();
+        await expect(
+          page.getByRole("option", { name: CHAT_MODEL_A, exact: true }),
+          `the Models dropdown does not offer ${CHAT_MODEL_A} to a team member`,
+        ).toBeVisible({ timeout: 15_000 });
+        await expect(
+          page.getByRole("option", { name: CHAT_MODEL_B, exact: true }),
+          `the Models dropdown does not offer ${CHAT_MODEL_B} to a team member`,
+        ).toBeVisible();
+
+        await page
+          .getByRole("option", { name: CHAT_MODEL_A, exact: true })
+          .click();
+        await page.keyboard.press("Escape");
+
+        const updated = page.waitForResponse(
+          (res) =>
+            res.url().includes("/key/update") &&
+            res.request().method() === "POST",
+        );
+        await page.getByRole("button", { name: "Save Changes" }).click();
+        const updateStatus = (await updated).status();
+        expect(
+          updateStatus,
+          "a team member's own-key edit was refused",
+        ).toBeGreaterThanOrEqual(200);
+        expect(
+          updateStatus,
+          "a team member's own-key edit was refused",
+        ).toBeLessThan(300);
+        await expect(
+          page.getByText("Key updated successfully").first(),
+        ).toBeVisible({ timeout: 15_000 });
+
+        await expect
+          .poll(
+            async () => (await readKeyInfo(request, created.token)).models,
+            {
+              message: `the narrowed model scope never reached /key/info for ${alias}`,
+              timeout: 20_000,
+            },
+          )
+          .toEqual([CHAT_MODEL_A]);
+
+        await expect
+          .poll(
+            async () =>
+              await attemptChatCompletion(request, {
+                model: CHAT_MODEL_B,
+                prompt: `out of scope ${suffix}`,
+                apiKey: created.key,
+              }),
+            {
+              message: `${CHAT_MODEL_B} was still served after the key was narrowed to ${CHAT_MODEL_A}`,
+              timeout: 30_000,
+            },
+          )
+          .toMatchObject({
+            status: 403,
+            body: expect.stringContaining(CHAT_MODEL_B),
+          });
+
+        const inScope = await attemptChatCompletion(request, {
+          model: CHAT_MODEL_A,
+          prompt: `in scope ${suffix}`,
+          apiKey: created.key,
+        });
+        expect(
+          inScope,
+          `${CHAT_MODEL_A} is no longer served by the narrowed key`,
+        ).toMatchObject({
+          status: 200,
+          body: expect.stringContaining(MOCK_RESPONSE_TEXT),
+        });
+      } finally {
+        await deleteVirtualKey(request, created.token);
+      }
+    } finally {
+      await request.post(`${rootPath()}/user/delete`, {
+        headers: {
+          Authorization: `Bearer ${masterKey()}`,
+          "Content-Type": "application/json",
+        },
+        data: { user_ids: [userId] },
+      });
+      await request.post(`${rootPath()}/team/delete`, {
+        headers: {
+          Authorization: `Bearer ${masterKey()}`,
+          "Content-Type": "application/json",
+        },
+        data: { team_ids: [teamId] },
+      });
+    }
+  });
+});
diff --git a/tests/e2e/ui/tests/internal-user/modelsByTeam.spec.ts b/tests/e2e/ui/tests/internal-user/modelsByTeam.spec.ts
new file mode 100644
index 00000000000..5e2c80b5845
--- /dev/null
+++ b/tests/e2e/ui/tests/internal-user/modelsByTeam.spec.ts
@@ -0,0 +1,196 @@
+import {
+  test as base,
+  expect,
+  type Locator,
+  type Page as PlaywrightPage,
+} from "@playwright/test";
+import {
+  E2E_TEAM_CRUD_ALIAS,
+  E2E_TEAM_ORG_ALIAS,
+  INTERNAL_USER_STORAGE_PATH,
+} from "../../constants";
+import { Page } from "../../fixtures/pages";
+import { navigateToPage } from "../../helpers/navigation";
+import { readBack } from "../../helpers/roundTrip";
+import { CHAT_MODEL_A, CHAT_MODEL_B, masterKey } from "../../helpers/traffic";
+
+const MOCK_LLM_BASE = `http://127.0.0.1:${process.env.MOCK_LLM_PORT ?? "8090"}/v1`;
+const CURRENT_TEAM_VIEW = "Current Team Models";
+const ALL_MODELS_VIEW = "All Available Models";
+const PERSONAL_TEAM = "Personal";
+
+const teamSelector = (page: PlaywrightPage): Locator =>
+  page.getByRole("combobox", { name: "Current team", exact: true });
+const viewSelector = (page: PlaywrightPage): Locator =>
+  page.getByRole("combobox", { name: "View", exact: true });
+
+async function chooseOption(
+  page: PlaywrightPage,
+  selector: Locator,
+  optionName: string,
+): Promise<void> {
+  await selector.click();
+  const option = page.getByRole("option", { name: optionName, exact: true });
+  await expect(option, `option ${optionName} is offered`).toBeVisible({
+    timeout: 10_000,
+  });
+  await option.click();
+  await expect(
+    selector,
+    `${optionName} is the selection the control now reports`,
+  ).toContainText(optionName, {
+    timeout: 10_000,
+  });
+}
+
+async function deleteDeployment(
+  page: PlaywrightPage,
+  id: string,
+): Promise<void> {
+  const post = () =>
+    page.request.post("/model/delete", {
+      headers: { Authorization: `Bearer ${masterKey()}` },
+      data: { id },
+    });
+  const deleted = await post().catch(() => post());
+  expect(
+    deleted.ok(),
+    `cleanup: /model/delete ${id} returned ${deleted.status()}`,
+  ).toBe(true);
+}
+
+function modelRow(page: PlaywrightPage, modelName: string): Locator {
+  return page.getByRole("row").filter({ hasText: modelName });
+}
+
+async function isRegistered(
+  page: PlaywrightPage,
+  modelName: string,
+): Promise<boolean> {
+  const body = await readBack<{ data: { model_name?: string }[] }>(
+    page,
+    "/v2/model/info",
+  );
+  return body.data.some((row) => row.model_name === modelName);
+}
+
+const uniqueSuffix = (): string =>
+  `${Date.now()}-${Math.random().toString(36).slice(2, 8)}`;
+
+const test = base.extend<{ ungrantedModelName: string }>({
+  ungrantedModelName: async ({ page }, use) => {
+    const ungrantedModelName = `e2e-ungranted-${uniqueSuffix()}`;
+    const created = await page.request.post("/model/new", {
+      headers: { Authorization: `Bearer ${masterKey()}` },
+      data: {
+        model_name: ungrantedModelName,
+        litellm_params: {
+          model: `openai/${ungrantedModelName}`,
+          api_base: MOCK_LLM_BASE,
+          api_key: "fake-key",
+        },
+        model_info: {},
+      },
+    });
+    expect(
+      created.ok(),
+      `/model/new failed: ${created.status()} ${await created.text()}`,
+    ).toBe(true);
+    const ungrantedModelId = (await created.json()).model_info?.id;
+    expect(ungrantedModelId, "model id from /model/new").toBeTruthy();
+
+    try {
+      await expect
+        .poll(async () => await isRegistered(page, ungrantedModelName), {
+          message: `deployment ${ungrantedModelName} never appeared in /v2/model/info after create`,
+          timeout: 60_000,
+        })
+        .toBe(true);
+      await use(ungrantedModelName);
+    } finally {
+      await deleteDeployment(page, ungrantedModelId);
+    }
+  },
+});
+
+test.describe("Models and Endpoints for an internal user", () => {
+  test.use({ storageState: INTERNAL_USER_STORAGE_PATH });
+
+  test("shows an internal user exactly the models of the team they select", async ({
+    page,
+    ungrantedModelName,
+  }) => {
+    await navigateToPage(page, Page.Models);
+
+    await expect(
+      page.getByRole("tab", { name: "Your Models" }),
+      "an internal user lands on their own models tab, not an admin-only view",
+    ).toBeVisible({ timeout: 15_000 });
+    await expect(
+      viewSelector(page),
+      "the models table opens scoped to the selected team",
+    ).toContainText(CURRENT_TEAM_VIEW, { timeout: 15_000 });
+    await expect(
+      modelRow(page, ungrantedModelName),
+      `the personal view lists ${ungrantedModelName}, so it is on the proxy and reachable from this page`,
+    ).toHaveCount(1, { timeout: 30_000 });
+
+    await chooseOption(page, teamSelector(page), E2E_TEAM_CRUD_ALIAS);
+    await expect(
+      modelRow(page, CHAT_MODEL_A),
+      `${E2E_TEAM_CRUD_ALIAS} lists ${CHAT_MODEL_A}`,
+    ).toHaveCount(1, {
+      timeout: 15_000,
+    });
+    await expect(
+      modelRow(page, CHAT_MODEL_B),
+      `${E2E_TEAM_CRUD_ALIAS} lists ${CHAT_MODEL_B}`,
+    ).toHaveCount(1, {
+      timeout: 15_000,
+    });
+    await expect(
+      modelRow(page, ungrantedModelName),
+      `${ungrantedModelName} is on the proxy but not granted to ${E2E_TEAM_CRUD_ALIAS}, so it must not be listed`,
+    ).toHaveCount(0);
+
+    await chooseOption(page, teamSelector(page), E2E_TEAM_ORG_ALIAS);
+    await expect(
+      modelRow(page, CHAT_MODEL_A),
+      `${E2E_TEAM_ORG_ALIAS} lists ${CHAT_MODEL_A}`,
+    ).toHaveCount(1, {
+      timeout: 15_000,
+    });
+    await expect(
+      page.getByTestId("pagination-range"),
+      `${E2E_TEAM_ORG_ALIAS} lists the one model it grants and nothing else`,
+    ).toHaveText("Showing 1-1 of 1", { timeout: 15_000 });
+    await expect(
+      modelRow(page, CHAT_MODEL_B),
+      `${CHAT_MODEL_B} belongs to another team and must not leak into ${E2E_TEAM_ORG_ALIAS}`,
+    ).toHaveCount(0);
+    await expect(
+      modelRow(page, ungrantedModelName),
+      `${ungrantedModelName} is granted to no team and must not leak into ${E2E_TEAM_ORG_ALIAS}`,
+    ).toHaveCount(0);
+
+    await chooseOption(page, viewSelector(page), ALL_MODELS_VIEW);
+    await expect(
+      modelRow(page, CHAT_MODEL_A),
+      `switching to ${ALL_MODELS_VIEW} leaves the table populated rather than blanking it`,
+    ).toHaveCount(1, { timeout: 15_000 });
+
+    await page.reload();
+    await expect(
+      teamSelector(page),
+      "the team selection is not persisted across a reload, so the table returns to the personal view",
+    ).toContainText(PERSONAL_TEAM, { timeout: 15_000 });
+    await expect(
+      viewSelector(page),
+      "the view selection is not persisted across a reload either",
+    ).toContainText(CURRENT_TEAM_VIEW, { timeout: 15_000 });
+    await expect(
+      modelRow(page, ungrantedModelName),
+      "the personal view still renders models after a reload rather than coming back empty",
+    ).toHaveCount(1, { timeout: 30_000 });
+  });
+});
diff --git a/tests/e2e/ui/tests/modelsPage/editLitellmParams.spec.ts b/tests/e2e/ui/tests/modelsPage/editLitellmParams.spec.ts
new file mode 100644
index 00000000000..4480515ae59
--- /dev/null
+++ b/tests/e2e/ui/tests/modelsPage/editLitellmParams.spec.ts
@@ -0,0 +1,252 @@
+import {
+  test as base,
+  expect,
+  type Page as PlaywrightPage,
+} from "@playwright/test";
+import { ADMIN_STORAGE_PATH } from "../../constants";
+import { Page } from "../../fixtures/pages";
+import { navigateToPage } from "../../helpers/navigation";
+import { captureRequestBody, readBack } from "../../helpers/roundTrip";
+import { masterKey, sendChatCompletion } from "../../helpers/traffic";
+
+const MOCK_LLM_BASE = `http://127.0.0.1:${process.env.MOCK_LLM_PORT ?? "8090"}/v1`;
+const CUSTOM_PARAM = "extra_headers";
+const CUSTOM_PARAM_VALUE = { "X-E2E-Edit-Probe": "one" };
+
+type StoredParams = Record<string, unknown>;
+
+async function readStoredParams(
+  page: PlaywrightPage,
+  modelId: string,
+): Promise<StoredParams> {
+  const body = await readBack<{ data: { litellm_params: StoredParams }[] }>(
+    page,
+    `/model/info?litellm_model_id=${modelId}`,
+  );
+  return body.data[0]?.litellm_params ?? {};
+}
+
+function paramsEditor(page: PlaywrightPage) {
+  return page.getByPlaceholder('"rpm": 100');
+}
+
+async function editParams(
+  page: PlaywrightPage,
+  mutate: (params: StoredParams) => StoredParams,
+): Promise<void> {
+  await page.getByRole("button", { name: "Edit Settings" }).click();
+  const editor = paramsEditor(page);
+  await expect(
+    editor,
+    "the LiteLLM Params editor is reachable on every visit to the edit form",
+  ).toBeVisible({
+    timeout: 15_000,
+  });
+  const shown = JSON.parse(await editor.inputValue()) as StoredParams;
+  await editor.fill(JSON.stringify(mutate(shown), null, 2));
+}
+
+async function deleteDeployment(
+  page: PlaywrightPage,
+  id: string,
+): Promise<void> {
+  const post = () =>
+    page.request.post("/model/delete", {
+      headers: { Authorization: `Bearer ${masterKey()}` },
+      data: { id },
+    });
+  const deleted = await post().catch(() => post());
+  expect(
+    deleted.ok(),
+    `cleanup: /model/delete ${id} returned ${deleted.status()}`,
+  ).toBe(true);
+}
+
+const uniqueSuffix = (): string =>
+  `${Date.now()}-${Math.random().toString(36).slice(2, 8)}`;
+
+const test = base.extend<{
+  deployment: { readonly modelName: string; readonly createdModelId: string };
+}>({
+  deployment: async ({ page, request }, use) => {
+    const modelName = `e2e-edit-params-${uniqueSuffix()}`;
+    const created = await page.request.post("/model/new", {
+      headers: { Authorization: `Bearer ${masterKey()}` },
+      data: {
+        model_name: modelName,
+        litellm_params: {
+          model: `openai/${modelName}`,
+          api_base: MOCK_LLM_BASE,
+          api_key: "fake-key",
+        },
+        model_info: {},
+      },
+    });
+    expect(
+      created.ok(),
+      `/model/new failed: ${created.status()} ${await created.text()}`,
+    ).toBe(true);
+    const createdModelId = (await created.json()).model_info?.id;
+    expect(createdModelId, "model id from /model/new").toBeTruthy();
+
+    try {
+      await expect
+        .poll(
+          async () => {
+            try {
+              await sendChatCompletion(request, {
+                model: modelName,
+                prompt: `warmup ${modelName}`,
+              });
+              return true;
+            } catch {
+              return false;
+            }
+          },
+          {
+            message: `deployment ${modelName} never became routable after /model/new`,
+            timeout: 60_000,
+          },
+        )
+        .toBe(true);
+      await use({ modelName, createdModelId });
+    } finally {
+      await deleteDeployment(page, createdModelId);
+    }
+  },
+});
+
+test.describe("Edit LiteLLM Params on a deployment", () => {
+  test.use({ storageState: ADMIN_STORAGE_PATH });
+
+  test("params added on a deployment can be re-edited, and the deployment keeps serving", async ({
+    page,
+    request,
+    deployment: { modelName, createdModelId },
+  }) => {
+    await navigateToPage(page, Page.Models);
+    const modelIdCell = page.getByTestId(`model-id-${createdModelId}`);
+    await expect(
+      modelIdCell,
+      `the Models table lists ${modelName}`,
+    ).toBeVisible({ timeout: 15_000 });
+    await modelIdCell.click();
+    await expect(page.getByText("Back to Models").first()).toBeVisible({
+      timeout: 15_000,
+    });
+
+    await editParams(page, (params) => ({
+      ...params,
+      temperature: 0.2,
+      [CUSTOM_PARAM]: CUSTOM_PARAM_VALUE,
+    }));
+    const firstSave = await captureRequestBody(
+      page,
+      { method: "PATCH", urlIncludes: `/model/${createdModelId}/update` },
+      async () => {
+        await page.getByRole("button", { name: "Save Changes" }).click();
+      },
+    );
+    expect(
+      firstSave.litellm_params?.temperature,
+      "the added temperature goes on the wire",
+    ).toBe(0.2);
+    expect(
+      firstSave.litellm_params?.[CUSTOM_PARAM],
+      `the added ${CUSTOM_PARAM} goes on the wire`,
+    ).toEqual(CUSTOM_PARAM_VALUE);
+    expect(
+      firstSave.litellm_params?.model,
+      "a params edit does not rewrite the upstream model",
+    ).toBe(`openai/${modelName}`);
+    expect(
+      firstSave.litellm_params?.api_base,
+      "a params edit does not rewrite the api base",
+    ).toBe(MOCK_LLM_BASE);
+    expect(
+      firstSave.litellm_params,
+      "the credential is never re-sent, so a masked placeholder cannot overwrite the stored key",
+    ).not.toHaveProperty("api_key");
+
+    await expect
+      .poll(
+        async () => (await readStoredParams(page, createdModelId)).temperature,
+        {
+          message: "the added temperature never reached the stored deployment",
+          timeout: 20_000,
+        },
+      )
+      .toBe(0.2);
+    const afterFirstSave = await readStoredParams(page, createdModelId);
+    expect(
+      afterFirstSave[CUSTOM_PARAM],
+      `the added ${CUSTOM_PARAM} reached the stored deployment`,
+    ).toEqual(CUSTOM_PARAM_VALUE);
+    expect(
+      afterFirstSave.model,
+      "the stored upstream model survived the edit",
+    ).toBe(`openai/${modelName}`);
+    expect(
+      afterFirstSave.api_base,
+      "the stored api base survived the edit",
+    ).toBe(MOCK_LLM_BASE);
+
+    await editParams(page, (params) => ({
+      ...Object.fromEntries(
+        Object.entries(params).filter(([key]) => key !== CUSTOM_PARAM),
+      ),
+      temperature: 0.7,
+    }));
+    const secondSave = await captureRequestBody(
+      page,
+      { method: "PATCH", urlIncludes: `/model/${createdModelId}/update` },
+      async () => {
+        await page.getByRole("button", { name: "Save Changes" }).click();
+      },
+    );
+    expect(
+      secondSave.litellm_params?.temperature,
+      "a param set by an earlier save can be edited again",
+    ).toBe(0.7);
+    expect(
+      secondSave.litellm_params,
+      `dropping ${CUSTOM_PARAM} from the editor drops it from the request the UI sends`,
+    ).not.toHaveProperty(CUSTOM_PARAM);
+    expect(
+      secondSave.litellm_params?.model,
+      "a second params edit still leaves the upstream model alone",
+    ).toBe(`openai/${modelName}`);
+    expect(
+      secondSave.litellm_params?.api_base,
+      "a second params edit still leaves the api base alone",
+    ).toBe(MOCK_LLM_BASE);
+    expect(
+      secondSave.litellm_params,
+      "the credential is still never re-sent",
+    ).not.toHaveProperty("api_key");
+
+    await expect
+      .poll(
+        async () => (await readStoredParams(page, createdModelId)).temperature,
+        {
+          message:
+            "the re-edited temperature never reached the stored deployment",
+          timeout: 20_000,
+        },
+      )
+      .toBe(0.7);
+
+    await page.reload();
+    await expect(
+      page
+        .getByRole("tabpanel", { name: "Overview" })
+        .getByText('"temperature": 0.7'),
+      "reopening the deployment renders the re-edited value, not the one from the first save",
+    ).toBeVisible({ timeout: 20_000 });
+
+    await sendChatCompletion(request, {
+      model: modelName,
+      prompt: `still serving ${modelName}`,
+    });
+  });
+});
diff --git a/tests/e2e/ui/tests/modelsPage/modelHealthStatus.spec.ts b/tests/e2e/ui/tests/modelsPage/modelHealthStatus.spec.ts
new file mode 100644
index 00000000000..247cce1b85d
--- /dev/null
+++ b/tests/e2e/ui/tests/modelsPage/modelHealthStatus.spec.ts
@@ -0,0 +1,245 @@
+import {
+  test as base,
+  expect,
+  type Locator,
+  type Page as PlaywrightPage,
+} from "@playwright/test";
+import { ADMIN_STORAGE_PATH } from "../../constants";
+import { Page } from "../../fixtures/pages";
+import { navigateToPage } from "../../helpers/navigation";
+import { readBack } from "../../helpers/roundTrip";
+import { masterKey } from "../../helpers/traffic";
+
+const MOCK_LLM_BASE = `http://127.0.0.1:${process.env.MOCK_LLM_PORT ?? "8090"}/v1`;
+const UNREACHABLE_BASE = "http://127.0.0.1:9/v1";
+
+async function isRegistered(
+  page: PlaywrightPage,
+  modelName: string,
+): Promise<boolean> {
+  const body = await readBack<{ data: { model_name?: string }[] }>(
+    page,
+    "/v2/model/info",
+  );
+  return body.data.some((row) => row.model_name === modelName);
+}
+
+function healthRow(page: PlaywrightPage, modelName: string): Locator {
+  return page.getByRole("row").filter({ hasText: modelName });
+}
+
+function pageOf(label: string): { current: number; total: number } {
+  const [current, total] = label
+    .replace("Page ", "")
+    .split(" of ")
+    .map((part) => Number(part.trim()));
+  return { current, total };
+}
+
+async function locateHealthRow(
+  page: PlaywrightPage,
+  modelName: string,
+): Promise<Locator> {
+  const pageLabel = page.getByTestId("pagination-page");
+  await expect(
+    pageLabel,
+    "the health table reports which page it is showing",
+  ).toBeVisible({ timeout: 20_000 });
+
+  const deadline = Date.now() + 60_000;
+  while (Date.now() < deadline) {
+    const row = healthRow(page, modelName);
+    const onThisPage = await row
+      .first()
+      .waitFor({ state: "visible", timeout: 3_000 })
+      .then(() => true)
+      .catch(() => false);
+    if (onThisPage) return row;
+
+    const { current, total } = pageOf(await pageLabel.innerText());
+    const goTo = current < total ? current + 1 : 1;
+    if (total === 1) continue;
+    await page
+      .getByRole("button", {
+        name: current < total ? "Go to next page" : "Go to first page",
+      })
+      .click();
+    await expect(pageLabel).toContainText(`Page ${goTo} of`, {
+      timeout: 15_000,
+    });
+  }
+  return healthRow(page, modelName);
+}
+
+async function openHealthTab(page: PlaywrightPage): Promise<void> {
+  await page.getByRole("tab", { name: "Health Status" }).click();
+  await expect(
+    page.getByRole("heading", { name: "Model Health Status" }),
+  ).toBeVisible({ timeout: 15_000 });
+}
+
+async function expectStatus(
+  page: PlaywrightPage,
+  modelName: string,
+  status: string,
+): Promise<void> {
+  const row = await locateHealthRow(page, modelName);
+  await expect(row, `${modelName} has one row in the health table`).toHaveCount(
+    1,
+    { timeout: 20_000 },
+  );
+  await expect(
+    row.getByText(status, { exact: true }),
+    `the Health Status cell for ${modelName} reads ${status}`,
+  ).toHaveCount(1, { timeout: 60_000 });
+}
+
+async function deleteDeployment(
+  page: PlaywrightPage,
+  id: string,
+): Promise<void> {
+  const post = () =>
+    page.request.post("/model/delete", {
+      headers: { Authorization: `Bearer ${masterKey()}` },
+      data: { id },
+    });
+  const deleted = await post().catch(() => post());
+  expect(
+    deleted.ok(),
+    `cleanup: /model/delete ${id} returned ${deleted.status()}`,
+  ).toBe(true);
+}
+
+const uniqueSuffix = (): string =>
+  `${Date.now()}-${Math.random().toString(36).slice(2, 8)}`;
+
+async function withDeployment(
+  page: PlaywrightPage,
+  prefix: string,
+  apiBase: string,
+  use: (name: string) => Promise<void>,
+): Promise<void> {
+  const name = `${prefix}-${uniqueSuffix()}`;
+  const created = await page.request.post("/model/new", {
+    headers: { Authorization: `Bearer ${masterKey()}` },
+    data: {
+      model_name: name,
+      litellm_params: {
+        model: `openai/${name}`,
+        api_base: apiBase,
+        api_key: "fake-key",
+      },
+      model_info: {},
+    },
+  });
+  expect(
+    created.ok(),
+    `/model/new for ${name} failed: ${created.status()} ${await created.text()}`,
+  ).toBe(true);
+  const id = (await created.json()).model_info?.id;
+  expect(id, `model id from /model/new for ${name}`).toBeTruthy();
+  try {
+    await expect
+      .poll(() => isRegistered(page, name), {
+        message: `deployment ${name} never appeared in /v2/model/info after create`,
+        timeout: 60_000,
+      })
+      .toBe(true);
+    await use(name);
+  } finally {
+    await deleteDeployment(page, id);
+  }
+}
+
+const test = base.extend<{ reachableName: string; unreachableName: string }>({
+  reachableName: async ({ page }, use) => {
+    await withDeployment(page, "e2e-health-up", MOCK_LLM_BASE, use);
+  },
+  unreachableName: async ({ page }, use) => {
+    await withDeployment(page, "e2e-health-down", UNREACHABLE_BASE, use);
+  },
+});
+
+test.describe("Model health status", () => {
+  test.use({ storageState: ADMIN_STORAGE_PATH });
+
+  test("Run Health Check reports a reachable deployment healthy and an unreachable one unhealthy", async ({
+    page,
+    reachableName,
+    unreachableName,
+  }) => {
+    await navigateToPage(page, Page.Models);
+    await openHealthTab(page);
+
+    for (const name of [reachableName, unreachableName]) {
+      const row = await locateHealthRow(page, name);
+      await expect(row, `${name} has one row in the health table`).toHaveCount(
+        1,
+        { timeout: 20_000 },
+      );
+      await row
+        .getByRole("button", { name: "Run Health Check", exact: true })
+        .click();
+    }
+
+    await expectStatus(page, reachableName, "healthy");
+    await expect(
+      healthRow(page, reachableName).getByText("unhealthy", { exact: true }),
+      "a reachable deployment is never reported unhealthy",
+    ).toHaveCount(0);
+    await expectStatus(page, unreachableName, "unhealthy");
+
+    const successDetail = (
+      await locateHealthRow(page, reachableName)
+    ).getByRole("button", {
+      name: "View response details",
+    });
+    await expect(
+      successDetail,
+      `${reachableName} offers its health check response for inspection`,
+    ).toBeVisible({ timeout: 60_000 });
+    await successDetail.click();
+    const successDialog = page.getByRole("dialog");
+    await expect(
+      successDialog.getByRole("heading", {
+        name: `Health Check Response - ${reachableName}`,
+      }),
+      "the healthy deployment's detail opens its own response dialog",
+    ).toBeVisible({ timeout: 10_000 });
+    await successDialog.getByRole("button", { name: "Close" }).last().click();
+    await expect(successDialog).toBeHidden({ timeout: 10_000 });
+
+    const errorDetail = (
+      await locateHealthRow(page, unreachableName)
+    ).getByRole("button", {
+      name: "View full error details",
+    });
+    await expect(
+      errorDetail,
+      `${unreachableName} offers its health check error for inspection`,
+    ).toBeVisible({ timeout: 60_000 });
+    await errorDetail.click();
+    const errorDialog = page.getByRole("dialog");
+    await expect(
+      errorDialog.getByRole("heading", {
+        name: `Health Check Error - ${unreachableName}`,
+      }),
+      "the unreachable deployment's detail opens its own error dialog",
+    ).toBeVisible({ timeout: 10_000 });
+    await expect(
+      errorDialog,
+      "the error dialog carries the upstream connection failure, not a generic message",
+    ).toContainText(/connection error/i, { timeout: 10_000 });
+    await expect(
+      errorDialog,
+      "the error dialog names the endpoint that could not be reached",
+    ).toContainText(UNREACHABLE_BASE);
+    await errorDialog.getByRole("button", { name: "Close" }).last().click();
+    await expect(errorDialog).toBeHidden({ timeout: 10_000 });
+
+    await page.reload();
+    await openHealthTab(page);
+    await expectStatus(page, reachableName, "healthy");
+    await expectStatus(page, unreachableName, "unhealthy");
+  });
+});
diff --git a/tests/e2e/ui/tests/proxy-admin/keyBlocking.spec.ts b/tests/e2e/ui/tests/proxy-admin/keyBlocking.spec.ts
new file mode 100644
index 00000000000..99a8065a797
--- /dev/null
+++ b/tests/e2e/ui/tests/proxy-admin/keyBlocking.spec.ts
@@ -0,0 +1,112 @@
+import { test as base, expect } from "@playwright/test";
+import { ADMIN_STORAGE_PATH } from "../../constants";
+import { Page } from "../../fixtures/pages";
+import { dismissFeedbackPopup, navigateToPage, openKeyDetail } from "../../helpers/navigation";
+import {
+  CHAT_MODEL_A,
+  MOCK_RESPONSE_TEXT,
+  attemptChatCompletion,
+  createVirtualKey,
+  deleteVirtualKey,
+  readKeyInfo,
+  sendChatCompletion,
+  uniqueSuffix,
+} from "../../helpers/traffic";
+
+interface ScopedKey {
+  alias: string;
+  token: string;
+  apiKey: string;
+}
+
+const test = base.extend<{ scopedKey: ScopedKey }>({
+  scopedKey: async ({ page }, use) => {
+    const alias = `e2e-block-key-${uniqueSuffix()}`;
+    const created = await createVirtualKey(page.request, {
+      key_alias: alias,
+      models: [CHAT_MODEL_A],
+    });
+    await use({ alias, token: created.token, apiKey: created.key });
+    await deleteVirtualKey(page.request, created.token);
+  },
+});
+
+test.describe("Proxy Admin - Key blocking", () => {
+  test.use({ storageState: ADMIN_STORAGE_PATH });
+
+  test("blocking a key stops it serving and unblocking restores it", async ({ page, scopedKey }) => {
+    const { alias, token, apiKey } = scopedKey;
+
+    await sendChatCompletion(page.request, {
+      model: CHAT_MODEL_A,
+      prompt: `pre-block ${alias}`,
+      apiKey,
+    });
+
+    await navigateToPage(page, Page.ApiKeys);
+    await dismissFeedbackPopup(page);
+    await openKeyDetail(page, alias);
+
+    await page.getByRole("button", { name: "More key actions" }).click();
+    await page.getByRole("menuitem", { name: "Block Key" }).click();
+    const blockDialog = page.getByRole("dialog", { name: "Block Key" });
+    await expect(blockDialog, "the Block Key confirmation never opened").toBeVisible({ timeout: 10_000 });
+    await blockDialog.getByRole("button", { name: "Block", exact: true }).click();
+
+    await expect
+      .poll(async () => (await readKeyInfo(page.request, token)).blocked, {
+        message: "the key never came back blocked from /key/info",
+        timeout: 20_000,
+      })
+      .toBe(true);
+
+    await expect
+      .poll(
+        async () =>
+          await attemptChatCompletion(page.request, {
+            model: CHAT_MODEL_A,
+            prompt: "blocked",
+            apiKey,
+          }),
+        {
+          message: "a blocked key was still served by /v1/chat/completions",
+          timeout: 30_000,
+        },
+      )
+      .toMatchObject({ status: 401, body: expect.stringContaining("blocked") });
+
+    await page.reload();
+    await expect(
+      page.getByText("Blocked", { exact: true }),
+      "the reloaded key detail does not show the key as blocked",
+    ).toBeVisible({ timeout: 15_000 });
+
+    await page.getByRole("button", { name: "More key actions" }).click();
+    await page.getByRole("menuitem", { name: "Unblock Key" }).click();
+    const unblockDialog = page.getByRole("dialog", { name: "Unblock Key" });
+    await expect(unblockDialog, "the Unblock Key confirmation never opened").toBeVisible({ timeout: 10_000 });
+    await unblockDialog.getByRole("button", { name: "Unblock", exact: true }).click();
+
+    await expect
+      .poll(async () => (await readKeyInfo(page.request, token)).blocked, {
+        message: "the key never came back unblocked from /key/info",
+        timeout: 20_000,
+      })
+      .toBe(false);
+
+    await expect
+      .poll(
+        async () =>
+          await attemptChatCompletion(page.request, {
+            model: CHAT_MODEL_A,
+            prompt: "unblocked",
+            apiKey,
+          }),
+        {
+          message: "an unblocked key is still refused by /v1/chat/completions",
+          timeout: 30_000,
+        },
+      )
+      .toMatchObject({ status: 200, body: expect.stringContaining(MOCK_RESPONSE_TEXT) });
+  });
+});
diff --git a/tests/e2e/ui/tests/proxy-admin/keyBudgetWindow.spec.ts b/tests/e2e/ui/tests/proxy-admin/keyBudgetWindow.spec.ts
new file mode 100644
index 00000000000..4e4d0a395c3
--- /dev/null
+++ b/tests/e2e/ui/tests/proxy-admin/keyBudgetWindow.spec.ts
@@ -0,0 +1,101 @@
+import { test as base, expect } from "@playwright/test";
+import { ADMIN_STORAGE_PATH, E2E_TEAM_CRUD_ID } from "../../constants";
+import { Page } from "../../fixtures/pages";
+import { dismissFeedbackPopup, navigateToPage, openKeyDetail } from "../../helpers/navigation";
+import { captureRequestBody } from "../../helpers/roundTrip";
+import { CHAT_MODEL_A, createVirtualKey, deleteVirtualKey, readKeyInfo, uniqueSuffix } from "../../helpers/traffic";
+
+interface ScopedKey {
+  alias: string;
+  token: string;
+}
+
+const test = base.extend<{ scopedKey: ScopedKey }>({
+  scopedKey: async ({ page }, use) => {
+    const alias = `e2e-budget-window-${uniqueSuffix()}`;
+    const created = await createVirtualKey(page.request, {
+      key_alias: alias,
+      team_id: E2E_TEAM_CRUD_ID,
+      models: [CHAT_MODEL_A],
+    });
+    await use({ alias, token: created.token });
+    await deleteVirtualKey(page.request, created.token);
+  },
+});
+
+test.describe("Proxy Admin - Key budget window", () => {
+  test.use({ storageState: ADMIN_STORAGE_PATH });
+
+  test("a monthly spend cap survives a reload, and clearing the window keeps the cap", async ({ page, scopedKey }) => {
+    const { alias, token } = scopedKey;
+
+    const before = await readKeyInfo(page.request, token);
+    expect(before.max_budget, "a freshly generated key starts with no budget").toBeNull();
+
+    await navigateToPage(page, Page.ApiKeys);
+    await dismissFeedbackPopup(page);
+    await openKeyDetail(page, alias);
+
+    await page.getByRole("tab", { name: "Settings" }).click();
+    await page.getByRole("button", { name: "Edit Settings" }).click();
+
+    await page.getByRole("spinbutton", { name: "Max Budget (USD)" }).fill("12.5");
+    await page.getByLabel("Reset Budget", { exact: true }).click();
+    await page.getByRole("option", { name: "monthly", exact: true }).click();
+    await page.getByRole("button", { name: "Save Changes" }).click();
+
+    await expect
+      .poll(async () => (await readKeyInfo(page.request, token)).max_budget, {
+        message: "the $12.50 cap never reached /key/info",
+        timeout: 20_000,
+      })
+      .toBe(12.5);
+    await expect
+      .poll(async () => (await readKeyInfo(page.request, token)).budget_duration, {
+        message: "the monthly reset window never reached /key/info",
+        timeout: 20_000,
+      })
+      .toBe("30d");
+
+    const capped = await readKeyInfo(page.request, token);
+    const resetAt = new Date(capped.budget_reset_at ?? "");
+    expect(Number.isNaN(resetAt.getTime()), "a monthly window left the key with no budget_reset_at").toBe(false);
+    expect(resetAt.getTime(), "budget_reset_at was set in the past").toBeGreaterThan(Date.now());
+    expect(resetAt.getUTCDate(), "a monthly window resets on the 1st, a daily one would not").toBe(1);
+
+    await page.reload();
+    await expect(
+      page.getByRole("paragraph").filter({ hasText: "of $12.50" }),
+      "the reloaded key detail does not render the $12.50 cap",
+    ).toBeVisible({ timeout: 15_000 });
+
+    await page.getByRole("tab", { name: "Settings" }).click();
+    await expect(
+      page.getByTestId("budget-reset-value"),
+      "the reloaded key detail does not name the 30d reset window",
+    ).toHaveText(/Every 30d/, { timeout: 15_000 });
+
+    await page.getByRole("button", { name: "Edit Settings" }).click();
+    await page.getByLabel("Reset Budget", { exact: true }).click();
+    await page.getByRole("option", { name: "Never resets", exact: true }).click();
+
+    const cleared = await captureRequestBody(page, { method: "POST", urlIncludes: "/key/update" }, async () => {
+      await page.getByRole("button", { name: "Save Changes" }).click();
+    });
+    expect(cleared).toHaveProperty("budget_duration");
+    expect(cleared.budget_duration, "clearing the window must send budget_duration: null explicitly").toBeNull();
+
+    await expect
+      .poll(async () => (await readKeyInfo(page.request, token)).budget_duration, {
+        message: "the reset window was never cleared on /key/info",
+        timeout: 20_000,
+      })
+      .toBeNull();
+
+    const after = await readKeyInfo(page.request, token);
+    expect(after.budget_reset_at, "clearing the reset window left a stale next-reset timestamp").toBeNull();
+    expect(after.max_budget, "clearing the reset window also wiped the spend cap").toBe(12.5);
+    expect(after.models, "editing the budget left the key's models untouched").toEqual(before.models);
+    expect(after.team_id, "editing the budget left the key's team untouched").toEqual(before.team_id);
+  });
+});
diff --git a/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py b/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
index 3fab20a28ad..e5826b18668 100644
--- a/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
+++ b/tests/litellm-proxy-extras/test_litellm_proxy_extras_utils.py
@@ -2,6 +2,7 @@ import glob
 import os
 import re
 import sys
+from pathlib import Path
 
 import pytest
 
@@ -870,3 +871,69 @@ class TestMigrateDeployAttemptAccounting:
             harness.run()
         assert len(harness.deploy_calls) == 1
         assert harness.resolved == []
+
+
+class TestJWTKeyMappingCascade:
+    """Regression tests for issue #33702.
+
+    A virtual key referenced by a LiteLLM_JWTKeyMapping row could not be deleted
+    because LiteLLM_JWTKeyMapping_token_fkey was created ON DELETE RESTRICT, so
+    deleting the key (Admin UI, /key/delete, team delete, ...) raised a foreign
+    key violation. The mapping must be removed automatically when its key is
+    deleted, which the FK now enforces via ON DELETE CASCADE.
+    """
+
+    _FK_NAME = "LiteLLM_JWTKeyMapping_token_fkey"
+
+    def _effective_on_delete(self):
+        """Replay every migration in order and return the last ON DELETE action
+        declared for the JWT key mapping FK."""
+        action = None
+        for _migration_name, sql in _get_all_migrations():
+            for match in re.finditer(
+                rf'ADD\s+CONSTRAINT\s+"{re.escape(self._FK_NAME)}".*?'
+                r"ON\s+DELETE\s+(CASCADE|RESTRICT|SET\s+NULL|NO\s+ACTION|SET\s+DEFAULT)",
+                sql,
+                re.IGNORECASE | re.DOTALL,
+            ):
+                action = re.sub(r"\s+", " ", match.group(1).upper())
+        return action
+
+    def test_fk_effective_on_delete_is_cascade(self):
+        """The final FK definition across all migrations must cascade deletes."""
+        assert self._effective_on_delete() == "CASCADE", (
+            f"{self._FK_NAME} must end up ON DELETE CASCADE so deleting a "
+            "virtual key removes its JWT key mapping (issue #33702)"
+        )
+
+    def test_schema_declares_cascade_on_relation(self):
+        """schema.prisma must declare onDelete: Cascade on the mapping relation
+        so the generated client and DB agree."""
+        schema_paths = glob.glob(
+            os.path.abspath(
+                os.path.join(
+                    os.path.dirname(__file__), "../../**/schema.prisma"
+                )
+            ),
+            recursive=True,
+        )
+        declaring = tuple(
+            (path, schema)
+            for path, schema in ((p, Path(p).read_text()) for p in schema_paths)
+            if "model LiteLLM_JWTKeyMapping" in schema
+        )
+        assert declaring, "No schema.prisma declaring LiteLLM_JWTKeyMapping found"
+        for path, schema in declaring:
+            match = re.search(
+                r"litellm_verification_token\s+LiteLLM_VerificationToken\s+@relation\(([^)]*)\)",
+                schema,
+            )
+            assert match is not None, (
+                f"{path} declares LiteLLM_JWTKeyMapping but its verification token "
+                "relation could not be parsed, so this test cannot vouch for it "
+                "(issue #33702)"
+            )
+            assert "onDelete: Cascade" in match.group(1), (
+                f"{path} must declare onDelete: Cascade on the JWT key mapping "
+                "relation (issue #33702)"
+            )
diff --git a/tests/litellm_utils_tests/test_proxy_budget_reset.py b/tests/litellm_utils_tests/test_proxy_budget_reset.py
index 9f6e1f4c3f7..4103536950d 100644
--- a/tests/litellm_utils_tests/test_proxy_budget_reset.py
+++ b/tests/litellm_utils_tests/test_proxy_budget_reset.py
@@ -401,7 +401,7 @@ async def test_reset_budget_endusers_are_zeroed_with_the_budget_window_advance()
 
     enduser_writes = [c for c in batch_calls if c["table"] == "enduser"]
     assert len(enduser_writes) == 1
-    assert enduser_writes[0]["where"]["user_id"]["in"] == [f"user{i}" for i in range(1, 7)]
+    assert enduser_writes[0]["where"] == {"budget_id": {"in": ["budget1"]}, "spend": {"gt": 0}}
     assert enduser_writes[0]["data"] == {"spend": 0}
 
     budget_writes = [c for c in batch_calls if c["table"] == "budget"]
@@ -602,7 +602,7 @@ async def test_reset_budget_continues_other_categories_on_failure():
     assert len([c for c in batch_calls if c["table"] == "team_membership"]) == 1
     enduser_writes = [c for c in batch_calls if c["table"] == "enduser"]
     assert len(enduser_writes) == 1
-    assert enduser_writes[0]["where"] == {"user_id": {"in": ["user1"]}}
+    assert enduser_writes[0]["where"] == {"budget_id": {"in": ["budget1"]}, "spend": {"gt": 0}}
     assert enduser_writes[0]["data"] == {"spend": 0}
 
     # Check the new batch write path: 2 keys + 1 user (user1 failed) + 2 teams.
@@ -1031,7 +1031,7 @@ async def test_service_logger_endusers_success():
 
     enduser_writes = [c for c in batch_calls if c["table"] == "enduser"]
     assert len(enduser_writes) == 1
-    assert enduser_writes[0]["where"] == {"user_id": {"in": ["user1", "user2"]}}
+    assert enduser_writes[0]["where"] == {"budget_id": {"in": ["budget1"]}, "spend": {"gt": 0}}
 
     proxy_logging_obj.service_logging_obj.async_service_success_hook.assert_called_once()
     (
diff --git a/tests/llm_translation/test_azure_o_series.py b/tests/llm_translation/test_azure_o_series.py
index 1a2d672af71..ce7e614cbe2 100644
--- a/tests/llm_translation/test_azure_o_series.py
+++ b/tests/llm_translation/test_azure_o_series.py
@@ -159,15 +159,23 @@ def test_azure_o_series_routing():
 def test_openai_o_series_max_retries_0(mock_get_openai_client):
     import litellm
 
+    mock_get_openai_client.return_value.chat.completions.with_raw_response.create.return_value.headers = {}
+    mock_get_openai_client.return_value.chat.completions.with_raw_response.create.return_value.parse.return_value = (
+        ModelResponse(choices=[{"message": {"role": "assistant", "content": "Hello"}}])
+    )
     litellm.set_verbose = True
     response = litellm.completion(
         model="azure/o1-preview",
         messages=[{"role": "user", "content": "hi"}],
         max_retries=0,
+        api_key="fake-key",
+        api_base="https://fake-azure.openai.azure.com",
+        api_version="2024-10-21",
     )
 
     mock_get_openai_client.assert_called_once()
     assert mock_get_openai_client.call_args.kwargs["max_retries"] == 0
+    assert response.choices[0].message.content == "Hello"
 
 
 @pytest.mark.asyncio
diff --git a/tests/llm_translation/test_azure_openai.py b/tests/llm_translation/test_azure_openai.py
index 0fa72b45ed8..e6528e77749 100644
--- a/tests/llm_translation/test_azure_openai.py
+++ b/tests/llm_translation/test_azure_openai.py
@@ -335,6 +335,10 @@ def test_azure_gpt_4o_with_tool_call_and_response_format(api_version):
     ]
 
     with patch.object(client.chat.completions.with_raw_response, "create") as mock_post:
+        mock_post.return_value.headers = {}
+        mock_post.return_value.parse.return_value = litellm.ModelResponse(
+            choices=[{"message": {"role": "assistant", "content": InvestigationOutput().model_dump_json()}}]
+        )
         response = litellm.completion(
             model="azure/gpt-4.1-mini",
             messages=[
@@ -362,6 +366,7 @@ def test_azure_gpt_4o_with_tool_call_and_response_format(api_version):
             assert "response_format" in mock_post.call_args.kwargs
         else:
             assert "response_format" not in mock_post.call_args.kwargs
+        assert response.choices[0].message.content == InvestigationOutput().model_dump_json()
 
 
 def test_map_openai_params():
diff --git a/tests/llm_translation/test_bedrock_dynamic_auth_params_unit_tests.py b/tests/llm_translation/test_bedrock_dynamic_auth_params_unit_tests.py
index dad2fdbf065..6c059423f74 100644
--- a/tests/llm_translation/test_bedrock_dynamic_auth_params_unit_tests.py
+++ b/tests/llm_translation/test_bedrock_dynamic_auth_params_unit_tests.py
@@ -194,6 +194,7 @@ class DummyCredentials:
         ("aws_web_identity_token", "dummy_web_identity_token"),
         ("aws_sts_endpoint", "dummy_sts_endpoint"),
         ("aws_external_id", "dummy_external_id"),
+        ("aws_session_tags", [{"Key": "team", "Value": "genai"}]),
     ],
 )
 def test_dynamic_aws_params_propagation(model, param_name, param_value):
diff --git a/tests/llm_translation/test_llm_response_utils/test_convert_dict_to_chat_completion.py b/tests/llm_translation/test_llm_response_utils/test_convert_dict_to_chat_completion.py
index b6e30ddc711..31c554985a7 100644
--- a/tests/llm_translation/test_llm_response_utils/test_convert_dict_to_chat_completion.py
+++ b/tests/llm_translation/test_llm_response_utils/test_convert_dict_to_chat_completion.py
@@ -1623,15 +1623,11 @@ class TestMissingChoicesGuard:
 
         assert "no 'choices'" in exc_info.value.message
 
-    def test_convert_to_model_response_object_empty_choices_raises_api_error(self):
-        """Empty choices list raises APIError, same as missing/null choices.
+    def test_convert_to_model_response_object_empty_choices_returns_empty_list(self):
+        """An empty choices list is a real provider answer, so it converts to choices=[] instead of raising.
 
-        Provider-specific repair (e.g. github_copilot synthesizing choices for
-        Anthropic-native responses) happens before this guard, in the provider
-        config; the core utility keeps treating empty choices as an error.
+        See: https://github.com/BerriAI/litellm/issues/40276
         """
-        from litellm.exceptions import APIError
-
         response_object = {
             "id": "msg_123",
             "model": "some-model",
@@ -1639,16 +1635,17 @@ class TestMissingChoicesGuard:
             "usage": {"prompt_tokens": 10, "completion_tokens": 1, "total_tokens": 11},
         }
 
-        with pytest.raises(APIError) as exc_info:
-            convert_to_model_response_object(
-                response_object=response_object,
-                model_response_object=ModelResponse(),
-            )
+        result = convert_to_model_response_object(
+            response_object=response_object,
+            model_response_object=ModelResponse(),
+        )
 
-        assert "no 'choices'" in exc_info.value.message
+        assert isinstance(result, ModelResponse)
+        assert result.choices == []
+        assert result.usage.prompt_tokens == 10
 
     def test_convert_to_model_response_object_null_choices_raises_api_error(self):
-        """choices=None raises APIError."""
+        """choices=None raises APIError that names the type instead of claiming the key is missing."""
         from litellm.exceptions import APIError
 
         response_object = {
@@ -1664,7 +1661,7 @@ class TestMissingChoicesGuard:
                 model_response_object=ModelResponse(),
             )
 
-        assert "no 'choices'" in exc_info.value.message
+        assert "'choices' that is not a list (NoneType)" in exc_info.value.message
 
     def test_convert_to_streaming_response_no_choices_raises_api_error(self):
         """Missing choices in streaming cache-hit path raises APIError."""
diff --git a/tests/llm_translation/test_openai.py b/tests/llm_translation/test_openai.py
index 2b9abdec5d0..af4ba85d58e 100644
--- a/tests/llm_translation/test_openai.py
+++ b/tests/llm_translation/test_openai.py
@@ -292,15 +292,21 @@ class TestOpenAIChatCompletion(BaseLLMChatTest):
 def test_openai_max_retries_0(mock_get_openai_client):
     import litellm
 
+    mock_get_openai_client.return_value.chat.completions.with_raw_response.create.return_value.headers = {}
+    mock_get_openai_client.return_value.chat.completions.with_raw_response.create.return_value.parse.return_value = (
+        ModelResponse(choices=[{"message": {"role": "assistant", "content": "Hello"}}])
+    )
     litellm.set_verbose = True
     response = litellm.completion(
         model="gpt-4o-mini",
         messages=[{"role": "user", "content": "hi"}],
         max_retries=0,
+        api_key="fake-key",
     )
 
     mock_get_openai_client.assert_called_once()
     assert mock_get_openai_client.call_args.kwargs["max_retries"] == 0
+    assert response.choices[0].message.content == "Hello"
 
 
 @patch("litellm.main.openai_chat_completions._get_openai_client")
diff --git a/tests/llm_translation/test_voyage_ai.py b/tests/llm_translation/test_voyage_ai.py
index 208e01110da..800751be115 100644
--- a/tests/llm_translation/test_voyage_ai.py
+++ b/tests/llm_translation/test_voyage_ai.py
@@ -139,6 +139,7 @@ class TestVoyageContextualEmbeddings:
 
         # Test contextual model detection
         assert config.is_contextualized_embeddings("voyage-context-3") is True
+        assert config.is_contextualized_embeddings("voyage-context-4") is True
         assert config.is_contextualized_embeddings("voyage-context-2") is True
         assert config.is_contextualized_embeddings("context-model") is True
 
diff --git a/tests/local_testing/test_completion.py b/tests/local_testing/test_completion.py
index f8f23ea015a..43ed57f63af 100644
--- a/tests/local_testing/test_completion.py
+++ b/tests/local_testing/test_completion.py
@@ -3999,10 +3999,14 @@ def test_completion_novita_ai():
     openai_client = OpenAI(api_key="fake-key")
 
     with patch.object(
-        openai_client.chat.completions, "create", new=MagicMock()
+        openai_client.chat.completions.with_raw_response, "create"
     ) as mock_call:
+        mock_call.return_value.headers = {}
+        mock_call.return_value.parse.return_value = litellm.ModelResponse(
+            choices=[{"message": {"role": "assistant", "content": "Hello"}}]
+        )
         try:
-            completion(
+            response = completion(
                 model="novita/meta-llama/llama-3.3-70b-instruct",
                 messages=messages,
                 client=openai_client,
@@ -4010,6 +4014,7 @@ def test_completion_novita_ai():
             )
 
             mock_call.assert_called_once()
+            assert response.choices[0].message.content == "Hello"
 
             # Verify model is passed correctly
             assert (
diff --git a/tests/local_testing/test_custom_callback_input.py b/tests/local_testing/test_custom_callback_input.py
index f0f24a6e6b2..834570091bd 100644
--- a/tests/local_testing/test_custom_callback_input.py
+++ b/tests/local_testing/test_custom_callback_input.py
@@ -1076,7 +1076,7 @@ def test_standard_logging_payload(model, turn_off_message_logging):
             )
         )
 
-        keys_list = list(StandardLoggingPayload.__annotations__.keys())
+        keys_list = list(StandardLoggingPayload.__required_keys__)
 
         for k in keys_list:
             assert (
@@ -1190,7 +1190,7 @@ def test_standard_logging_payload_audio(turn_off_message_logging, stream):
             )
         )
 
-        keys_list = list(StandardLoggingPayload.__annotations__.keys())
+        keys_list = list(StandardLoggingPayload.__required_keys__)
 
         for k in keys_list:
             assert (
diff --git a/tests/logging_callback_tests/test_datadog.py b/tests/logging_callback_tests/test_datadog.py
index 83a652e8884..7ac9ac0b5ad 100644
--- a/tests/logging_callback_tests/test_datadog.py
+++ b/tests/logging_callback_tests/test_datadog.py
@@ -270,7 +270,7 @@ async def test_datadog_logging_http_request():
         message = json.loads(body[0]["message"])
         print("logged message", json.dumps(message, indent=4))
 
-        expected_message_fields = StandardLoggingPayload.__annotations__.keys()
+        expected_message_fields = StandardLoggingPayload.__required_keys__
 
         for field in expected_message_fields:
             assert field in message, f"Field '{field}' is missing from the message"
diff --git a/tests/mcp_tests/mcp_server.py b/tests/mcp_tests/mcp_server.py
index bc6accbb721..eba7cae1bca 100644
--- a/tests/mcp_tests/mcp_server.py
+++ b/tests/mcp_tests/mcp_server.py
@@ -1,10 +1,12 @@
 # math_server.py
 import argparse
 import os
+from typing import Final
 
-from mcp.server.fastmcp import FastMCP
+from mcp.server.fastmcp import Context, FastMCP
 
 mcp = FastMCP("Math")
+ADD_OFFSET: Final = int(os.getenv("MCP_ADD_OFFSET", "0"))
 
 
 def _parse_args() -> argparse.Namespace:
@@ -31,7 +33,7 @@ def _parse_args() -> argparse.Namespace:
 @mcp.tool()
 def add(a: int, b: int) -> int:
     """Add two numbers"""
-    return a + b
+    return a + b + ADD_OFFSET
 
 
 @mcp.tool()
@@ -40,6 +42,15 @@ def multiply(a: int, b: int) -> int:
     return a * b
 
 
+@mcp.tool()
+def request_headers(ctx: Context) -> dict[str, str]:
+    request: Final = ctx.request_context.request
+    return {
+        "authorization": request.headers.get("authorization", "") if request is not None else "",
+        "x-request-tag": request.headers.get("x-request-tag", "") if request is not None else "",
+    }
+
+
 def main() -> None:
     args = _parse_args()
     transport = (args.transport or "stdio").lower()
diff --git a/tests/mcp_tests/test_configs/test_config_mcp_e2e.yaml b/tests/mcp_tests/test_configs/test_config_mcp_e2e.yaml
index ad68a03781d..19fad3d1393 100644
--- a/tests/mcp_tests/test_configs/test_config_mcp_e2e.yaml
+++ b/tests/mcp_tests/test_configs/test_config_mcp_e2e.yaml
@@ -23,3 +23,6 @@ mcp_servers:
     transport: http
     url: http://127.0.0.1:0/mcp
     allow_all_keys: true
+  math_restricted:
+    transport: http
+    url: http://127.0.0.1:0/mcp
diff --git a/tests/mcp_tests/test_proxy_mcp_e2e.py b/tests/mcp_tests/test_proxy_mcp_e2e.py
index a97eed82e18..e1099fe0a62 100644
--- a/tests/mcp_tests/test_proxy_mcp_e2e.py
+++ b/tests/mcp_tests/test_proxy_mcp_e2e.py
@@ -1,27 +1,39 @@
 import asyncio
 import json
 import os
+import queue
 import socket
 import subprocess
 import sys
+import tempfile
 import threading
 import time
 import typing
+from contextlib import asynccontextmanager, contextmanager
+from dataclasses import dataclass
+from datetime import datetime
 from pathlib import Path
 
+import httpx
 import pytest
 import uvicorn
 import yaml
 from mcp import ClientSession
 from mcp.client.streamable_http import streamablehttp_client
+from mcp.types import CallToolResult
+from starlette.requests import Request
 
+from litellm.integrations.custom_logger import CustomLogger
+from litellm.proxy._experimental.mcp_server.tool_search import handle_mcp_proxy_tool
+from litellm.proxy._types import LiteLLM_ObjectPermissionTable, ProxyException, UserAPIKeyAuth
 from litellm.proxy.proxy_server import (
     app as proxy_app,
+)
+from litellm.proxy.proxy_server import (
     cleanup_router_config_variables,
     initialize,
 )
 
-
 CONFIG_TEMPLATE_PATH = Path("tests/mcp_tests/test_configs/test_config_mcp_e2e.yaml")
 MCP_SERVER_SCRIPT = Path("tests/mcp_tests/mcp_server.py")
 PROJECT_ROOT = Path(__file__).resolve().parents[2]
@@ -46,28 +58,49 @@ def _clear_proxy_database_env() -> typing.Iterator[None]:
         mp.undo()
 
 
-def _initialize_proxy(config_path: str) -> None:
+async def _initialize_proxy(config_path: str) -> None:
+    from litellm.proxy._experimental.mcp_server.mcp_server_manager import global_mcp_server_manager
+
     cleanup_router_config_variables()
-    asyncio.run(initialize(config=config_path, debug=True))
+    await initialize(config=config_path, debug=True)
+    for server_id, upstream in tuple(global_mcp_server_manager.registry.items()):
+        if upstream.server_name != "math_restricted":
+            continue
+        global_mcp_server_manager.registry[server_id] = upstream.model_copy(
+            update={"tool_name_to_display_name": {"add": "Add Numbers"}}
+        )
+
+
+@dataclass(frozen=True)
+class ProxyRig:
+    url: str
+    config_path: str
+    loop: asyncio.AbstractEventLoop
 
 
 def _start_proxy_server(
     config_path: str,
-) -> tuple[str, uvicorn.Server, threading.Thread, socket.socket]:
-    _initialize_proxy(config_path)
-
+) -> tuple[ProxyRig, uvicorn.Server, threading.Thread, socket.socket]:
     sock = socket.socket(socket.AF_INET, socket.SOCK_STREAM)
     sock.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
     sock.bind(("127.0.0.1", 0))
     host, port = sock.getsockname()
 
-    config = uvicorn.Config(proxy_app, host=host, port=port, log_level="warning")
+    config = uvicorn.Config(proxy_app, host=host, port=port, log_level="warning", lifespan="off")
     server = uvicorn.Server(config)
 
+    loop = asyncio.new_event_loop()
+
+    async def _serve() -> None:
+        from litellm.proxy._experimental.mcp_server import server as mcp_server
+
+        await _initialize_proxy(config_path)
+        async with proxy_app.router.lifespan_context(proxy_app), mcp_server.lifespan(proxy_app):
+            await server.serve(sockets=[sock])
+
     def _run() -> None:
-        loop = asyncio.new_event_loop()
-        asyncio.set_event_loop(loop)
-        loop.run_until_complete(server.serve(sockets=[sock]))
+        with asyncio.Runner(loop_factory=lambda: loop) as runner:
+            runner.run(_serve())
 
     thread = threading.Thread(target=_run, daemon=True)
     thread.start()
@@ -80,75 +113,93 @@ def _start_proxy_server(
             raise TimeoutError("Proxy server did not start in time")
         time.sleep(0.05)
 
-    return f"http://{host}:{port}", server, thread, sock
+    return ProxyRig(f"http://{host}:{port}", config_path, loop), server, thread, sock
 
 
-@pytest.fixture(scope="session")
-def math_streamable_http_server() -> str:
+@contextmanager
+def _math_http_server(offset: int) -> typing.Iterator[str]:
     host = "127.0.0.1"
     with socket.socket(socket.AF_INET, socket.SOCK_STREAM) as sock:
         sock.bind((host, 0))
         _, port = sock.getsockname()
 
-    cmd = [
-        sys.executable,
-        str(MCP_SERVER_SCRIPT),
-        "--transport",
-        "http",
-        "--host",
-        host,
-        "--port",
-        str(port),
-    ]
-
-    env = os.environ.copy()
-    server_process = subprocess.Popen(
-        cmd,
-        cwd=str(PROJECT_ROOT),
-        stdout=subprocess.PIPE,
-        stderr=subprocess.PIPE,
-    )
-
-    start_time = time.time()
-    while True:
-        if server_process.poll() is not None:
-            stdout, stderr = server_process.communicate()
-            raise RuntimeError(
-                f"Streamable HTTP MCP server exited early.\nSTDOUT: {stdout.decode()}\nSTDERR: {stderr.decode()}"
-            )
+    with tempfile.TemporaryFile() as server_log:
+        process = subprocess.Popen(
+            [sys.executable, str(MCP_SERVER_SCRIPT), "--transport", "http", "--host", host, "--port", str(port)],
+            cwd=str(PROJECT_ROOT),
+            stdout=server_log,
+            stderr=subprocess.STDOUT,
+            env={**os.environ, "MCP_ADD_OFFSET": str(offset)},
+        )
         try:
-            with socket.create_connection((host, port), timeout=0.1):
-                break
-        except OSError:
-            if time.time() - start_time > PROXY_START_TIMEOUT:
-                server_process.terminate()
-                raise TimeoutError("Streamable HTTP MCP server did not start in time")
-            time.sleep(0.05)
-
-    yield f"http://{host}:{port}"
-
-    server_process.terminate()
-    try:
-        server_process.wait(timeout=5)
-    except subprocess.TimeoutExpired:
-        server_process.kill()
+            start_time = time.monotonic()
+            while True:
+                if process.poll() is not None:
+                    server_log.seek(0)
+                    raise RuntimeError(f"MCP upstream exited early: {server_log.read().decode()}")
+                try:
+                    with socket.create_connection((host, port), timeout=0.1):
+                        break
+                except OSError:
+                    if time.monotonic() - start_time > PROXY_START_TIMEOUT:
+                        raise TimeoutError("Streamable HTTP MCP server did not start in time")
+                    time.sleep(0.05)
+            yield f"http://{host}:{port}"
+        finally:
+            process.terminate()
+            try:
+                process.wait(timeout=5)
+            except subprocess.TimeoutExpired:
+                process.kill()
+                process.wait(timeout=5)
 
 
 @pytest.fixture(scope="session")
-def proxy_server_url(tmp_path_factory: pytest.TempPathFactory, math_streamable_http_server: str):
+def math_streamable_http_server() -> typing.Iterator[str]:
+    with _math_http_server(100) as url:
+        yield url
+
+
+@pytest.fixture(scope="session")
+def math_restricted_server() -> typing.Iterator[str]:
+    with _math_http_server(200) as url:
+        yield url
+
+
+@pytest.fixture(scope="session")
+def _proxy_server(
+    tmp_path_factory: pytest.TempPathFactory,
+    math_streamable_http_server: str,
+    math_restricted_server: str,
+):
     config_dir = tmp_path_factory.mktemp("mcp_e2e")
     config_path = config_dir / "config.yaml"
     config = yaml.safe_load(CONFIG_TEMPLATE_PATH.read_text())
+    config["mcp_servers"]["math_stdio"]["command"] = sys.executable
     config["mcp_servers"]["math_streamable_http"]["url"] = f"{math_streamable_http_server}/mcp"
+    config["mcp_servers"]["math_restricted"]["url"] = f"{math_restricted_server}/mcp"
+    config["general_settings"]["custom_auth"] = f"{__name__}.authorize_proxy_key"
+    config["litellm_settings"]["callbacks"] = [f"{__name__}.proxy_call_recorder"]
+    config["mcp_servers"]["math_restricted"]["mcp_info"] = {"mcp_server_cost_info": {"default_cost_per_query": 0.25}}
     config_path.write_text(yaml.safe_dump(config))
 
-    server_url, server, thread, sock = _start_proxy_server(str(config_path))
+    rig, server, thread, sock = _start_proxy_server(str(config_path))
 
-    yield server_url
+    try:
+        yield rig
+    finally:
+        server.should_exit = True
+        thread.join(timeout=10)
+        sock.close()
+        assert not thread.is_alive(), "Proxy did not shut down"
 
-    server.should_exit = True
-    thread.join(timeout=10)
-    sock.close()
+
+@pytest.fixture
+def proxy_server_url(_proxy_server: ProxyRig, setup_and_teardown: None) -> str:
+    asyncio.run_coroutine_threadsafe(_initialize_proxy(_proxy_server.config_path), _proxy_server.loop).result(
+        timeout=30
+    )
+    return _proxy_server.url
 
 
 class TestProxyMcpSimpleConnections:
@@ -192,7 +243,7 @@ class TestProxyMcpSimpleConnections:
                     assert result.content
                     first_content = result.content[0]
                     text = getattr(first_content, "text", None)
-                    assert text == "11"
+                    assert text == "111"
 
     @pytest.mark.asyncio
     async def test_proxy_mcp_lists_all_servers_without_header(self, proxy_server_url: str) -> None:
@@ -222,7 +273,7 @@ class TestProxyMcpSimpleConnections:
                     stdio_result = await _call_and_get_text("math_stdio-add", a=2, b=3)
                     streamable_result = await _call_and_get_text("math_streamable_http-add", a=4, b=5)
                     assert stdio_result == "5"
-                    assert streamable_result == "9"
+                    assert streamable_result == "109"
 
 
 class TestProxyMcpStatelessBehavior:
@@ -349,7 +400,7 @@ class TestProxyMcpSchemaDiscoveryMode:
                         },
                     )
                     assert stdio.isError is False and stdio.content[0].text == "7"
-                    assert http.isError is False and http.content[0].text == "11"
+                    assert http.isError is False and http.content[0].text == "111"
 
     @pytest.mark.asyncio
     async def test_server_scope_header_narrows_discovery(self, proxy_server_url: str) -> None:
@@ -384,6 +435,12 @@ class TestProxyMcpSchemaDiscoveryMode:
                     stale = await session.call_tool("get_tool_schema", arguments={"tool_id": "0" * 32})
                     assert stale.isError is True and "unauthorized tool_id" in stale.content[0].text
 
+                    for not_an_object in ("wrong", False):
+                        refused_args = await session.call_tool(
+                            "call_tool", arguments={"tool_id": tool_id, "arguments": not_an_object}
+                        )
+                        assert refused_args.isError is True and "object" in refused_args.content[0].text
+
                     direct = await session.call_tool("math_stdio-add", arguments={"a": 1, "b": 2})
                     assert direct.isError is True and "unavailable on /mcp/proxy" in direct.content[0].text
 
@@ -391,3 +448,273 @@ class TestProxyMcpSchemaDiscoveryMode:
                         with pytest.raises(McpError) as refused:
                             await operation()
                         assert refused.value.error.code == METHOD_NOT_FOUND
+
+
+async def authorize_proxy_key(request: Request, api_key: str) -> UserAPIKeyAuth:
+    permissions = {
+        "sk-1234": LiteLLM_ObjectPermissionTable(object_permission_id="open", mcp_servers=["math_stdio"]),
+        "sk-restricted": LiteLLM_ObjectPermissionTable(
+            object_permission_id="restricted", mcp_servers=["math_restricted"]
+        ),
+        "sk-none": LiteLLM_ObjectPermissionTable(object_permission_id="none", mcp_servers=["no-mcp-servers"]),
+        "sk-add-only": LiteLLM_ObjectPermissionTable(
+            object_permission_id="add-only", mcp_servers=["math_stdio"], mcp_tool_permissions={"math_stdio": ["add"]}
+        ),
+    }
+    permission = permissions.get(api_key)
+    if permission is None:
+        raise ProxyException(message="Unknown test key", type="authentication_error", param=None, code=401)
+    return UserAPIKeyAuth(api_key=api_key, user_id=api_key, object_permission=permission)
+
+
+class ProxyCallRecorder(CustomLogger):
+    def __init__(self) -> None:
+        super().__init__()
+        self.events: queue.Queue[str] = queue.Queue()
+        self.failures: queue.Queue[str] = queue.Queue()
+
+    async def async_log_success_event(
+        self, kwargs: dict[str, object], response_obj: object, start_time: datetime, end_time: datetime
+    ) -> None:
+        payload = kwargs.get("standard_logging_object")
+        if isinstance(payload, dict) and payload.get("call_type") == "call_mcp_tool":
+            self.events.put(json.dumps(payload, default=str))
+
+    async def async_log_failure_event(
+        self, kwargs: dict[str, object], response_obj: object, start_time: datetime, end_time: datetime
+    ) -> None:
+        payload = kwargs.get("standard_logging_object")
+        if isinstance(payload, dict) and payload.get("call_type") == "call_mcp_tool":
+            self.failures.put(json.dumps(payload, default=str))
+
+
+proxy_call_recorder = ProxyCallRecorder()
+
+
+@asynccontextmanager
+async def _scoped_session(url: str, key: str = "sk-1234", **headers: str) -> typing.AsyncIterator[ClientSession]:
+    async with asyncio.timeout(30):
+        async with _proxy_session(url, Authorization=f"Bearer {key}", **headers) as (read, write, _sid):
+            async with ClientSession(read, write) as session:
+                await session.initialize()
+                yield session
+
+
+async def _search(session: ClientSession, query: str) -> dict[str, str]:
+    result = await session.call_tool("search_tools", arguments={"query": query})
+    assert result.isError is False, result
+    return {hit["name"]: hit["tool_id"] for hit in _payload(result)}
+
+
+async def _call(session: ClientSession, tool_id: str, a: int = 3, b: int = 4) -> CallToolResult:
+    return await session.call_tool("call_tool", arguments={"tool_id": tool_id, "arguments": {"a": a, "b": b}})
+
+
+async def _raw_rpc(
+    proxy_server_url: str, key: str | None, method: str, params: dict[str, object], **headers: str
+) -> httpx.Response:
+    async with httpx.AsyncClient() as client:
+        return await client.post(
+            f"{proxy_server_url}/mcp/proxy",
+            headers={
+                "Accept": "application/json, text/event-stream",
+                **({"Authorization": f"Bearer {key}"} if key else {}),
+                **headers,
+            },
+            json={"jsonrpc": "2.0", "id": 1, "method": method, "params": params},
+        )
+
+
+async def _raw_initialize(proxy_server_url: str, key: str | None) -> httpx.Response:
+    return await _raw_rpc(
+        proxy_server_url,
+        key,
+        "initialize",
+        {"protocolVersion": "2025-03-26", "capabilities": {}, "clientInfo": {"name": "auth-test", "version": "1"}},
+    )
+
+
+def _rpc_result(response: httpx.Response) -> dict[str, typing.Any]:
+    if response.headers["content-type"].startswith("text/event-stream"):
+        data_line = next(line for line in response.text.splitlines() if line.startswith("data:"))
+        return json.loads(data_line.removeprefix("data:"))["result"]
+    return response.json()["result"]
+
+
+def _assert_unauthorized(result: CallToolResult) -> None:
+    assert result.isError is True
+    assert result.content[0].text == "Unknown or unauthorized tool_id"
+
+
+class TestProxyMcpAuthorizationScope:
+    @pytest.mark.asyncio
+    async def test_server_grant_bounds_search_and_blocks_foreign_ids(self, proxy_server_url: str) -> None:
+        async with _scoped_session(proxy_server_url, "sk-restricted") as granted:
+            restricted_id = (await _search(granted, "add"))["math_restricted-add"]
+            assert (await _call(granted, restricted_id)).content[0].text == "207"
+        async with _scoped_session(proxy_server_url) as ungranted:
+            assert set(await _search(ungranted, "add")) == {"math_stdio-add", "math_streamable_http-add"}
+            _assert_unauthorized(await ungranted.call_tool("get_tool_schema", {"tool_id": restricted_id}))
+            _assert_unauthorized(await _call(ungranted, restricted_id))
+
+    @pytest.mark.asyncio
+    async def test_no_mcp_servers_sentinel_rejects_initialize_and_hides_every_tool(self, proxy_server_url: str) -> None:
+        async with _scoped_session(proxy_server_url) as granted:
+            tool_id = (await _search(granted, "add"))["math_stdio-add"]
+        response = await _raw_initialize(proxy_server_url, "sk-none")
+        assert response.status_code == 403, response.text
+        assert "no MCP servers granted" in response.json()["detail"]["error"]
+
+        async def raw_call(name: str, arguments: dict[str, object]) -> dict[str, typing.Any]:
+            call = await _raw_rpc(proxy_server_url, "sk-none", "tools/call", {"name": name, "arguments": arguments})
+            assert call.status_code == 200, call.text
+            return _rpc_result(call)
+
+        listed = await _raw_rpc(proxy_server_url, "sk-none", "tools/list", {})
+        assert listed.status_code == 200, listed.text
+        assert {tool["name"] for tool in _rpc_result(listed)["tools"]} == {"search_tools", "get_tool_schema", "call_tool"}
+        search = await raw_call("search_tools", {"query": "add"})
+        assert search["isError"] is False, search
+        assert json.loads(search["content"][0]["text"]) == []
+        for name, arguments in (
+            ("get_tool_schema", {"tool_id": tool_id}),
+            ("call_tool", {"tool_id": tool_id, "arguments": {"a": 3, "b": 4}}),
+        ):
+            denied = await raw_call(name, arguments)
+            assert denied["isError"] is True, denied
+            assert denied["content"][0]["text"] == "Unknown or unauthorized tool_id"
+
+    @pytest.mark.asyncio
+    async def test_tool_grant_hides_ungranted_tools_and_blocks_their_ids(self, proxy_server_url: str) -> None:
+        async with _scoped_session(proxy_server_url) as granted:
+            multiply_id = (await _search(granted, "multiply"))["math_stdio-multiply"]
+        async with _scoped_session(proxy_server_url, "sk-add-only", **{"x-mcp-servers": "math_stdio"}) as session:
+            ids = await _search(session, "add multiply request_headers")
+            assert set(ids) == {"math_stdio-add"}
+            assert (await _call(session, ids["math_stdio-add"])).content[0].text == "7"
+            _assert_unauthorized(await session.call_tool("get_tool_schema", {"tool_id": multiply_id}))
+            _assert_unauthorized(await _call(session, multiply_id))
+
+    @pytest.mark.asyncio
+    async def test_same_named_tools_keep_distinct_ids_and_reach_their_own_upstream(self, proxy_server_url: str) -> None:
+        async with _scoped_session(proxy_server_url, "sk-restricted") as session:
+            ids = await _search(session, "add")
+            assert set(ids) == {"math_stdio-add", "math_streamable_http-add", "math_restricted-add"}
+            assert len(set(ids.values())) == 3
+            assert all(len(tool_id) == 32 for tool_id in ids.values())
+            for name, expected in (
+                ("math_stdio-add", "7"),
+                ("math_streamable_http-add", "107"),
+                ("math_restricted-add", "207"),
+            ):
+                schema = _payload(await session.call_tool("get_tool_schema", {"tool_id": ids[name]}))
+                assert schema["name"] == name
+                assert schema["tool_id"] == ids[name]
+                result = await _call(session, ids[name])
+                assert result.isError is False
+                assert result.content[0].text == expected
+
+    @pytest.mark.asyncio
+    async def test_server_scope_header_narrows_grants_and_blocks_out_of_scope_ids(self, proxy_server_url: str) -> None:
+        async with _scoped_session(proxy_server_url, "sk-restricted") as unscoped:
+            other_id = (await _search(unscoped, "add"))["math_stdio-add"]
+        async with _scoped_session(
+            proxy_server_url, "sk-restricted", **{"x-mcp-servers": "math_restricted"}
+        ) as session:
+            ids = await _search(session, "add")
+            assert set(ids) == {"math_restricted-add"}
+            _assert_unauthorized(await session.call_tool("get_tool_schema", {"tool_id": other_id}))
+            _assert_unauthorized(await _call(session, other_id))
+            assert (await _call(session, ids["math_restricted-add"])).content[0].text == "207"
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("key", [None, "sk-invalid"])
+    async def test_missing_or_invalid_key_cannot_initialize(self, proxy_server_url: str, key: str | None) -> None:
+        response = await _raw_initialize(proxy_server_url, key)
+        assert response.status_code == 401, response.text
+
+    @pytest.mark.asyncio
+    async def test_server_headers_are_forwarded_only_to_the_named_upstream(self, proxy_server_url: str) -> None:
+        for tag in ("first-request", "second-request"):
+            async with _scoped_session(
+                proxy_server_url,
+                "sk-restricted",
+                **{
+                    "x-mcp-math_restricted-authorization": f"Bearer {tag}",
+                    "x-mcp-math_restricted-x-request-tag": tag,
+                },
+            ) as session:
+                ids = await _search(session, "request_headers")
+                for name, expected in (
+                    ("math_restricted", {"authorization": f"Bearer {tag}", "x-request-tag": tag}),
+                    ("math_streamable_http", {"authorization": "", "x-request-tag": ""}),
+                ):
+                    result = await session.call_tool(
+                        "call_tool", {"tool_id": ids[f"{name}-request_headers"], "arguments": {}}
+                    )
+                    assert result.isError is False
+                    assert _payload(result) == expected
+
+    @pytest.mark.asyncio
+    async def test_proxy_call_emits_spend_log(self, proxy_server_url: str) -> None:
+        async with _scoped_session(proxy_server_url, "sk-restricted") as session:
+            tool_id = (await _search(session, "add"))["math_restricted-add"]
+            result = await _call(session, tool_id, 123, 456)
+            assert result.isError is False and result.content[0].text == "779"
+            async with asyncio.timeout(10):
+                while True:
+                    payload = json.loads(await asyncio.to_thread(proxy_call_recorder.events.get, True, 5))
+                    if payload.get("metadata", {}).get("mcp_tool_call_metadata", {}).get("arguments") == {
+                        "a": 123,
+                        "b": 456,
+                    }:
+                        break
+            assert payload["call_type"] == "call_mcp_tool"
+            assert payload["response_cost"] == 0.25
+            assert payload["status"] == "success"
+            assert payload["metadata"]["mcp_tool_call_metadata"]["mcp_server_name"] == "math_restricted"
+            assert payload["metadata"]["mcp_tool_call_metadata"]["name"] == "add"
+            assert payload["metadata"]["mcp_tool_call_metadata"]["namespaced_tool_name"] == "math_restricted/add"
+
+    @pytest.mark.asyncio
+    async def test_proxy_scope_exception_returns_iserror_and_emits_failure_log(self, proxy_server_url: str) -> None:
+        response = await _raw_rpc(
+            proxy_server_url,
+            "sk-none",
+            "tools/call",
+            {"name": "call_tool", "arguments": {"tool_id": "denied-scope", "arguments": {}}},
+            **{"x-mcp-servers": "math_restricted", "x-litellm-call-id": "proxy-scope-denial"},
+        )
+        assert response.status_code == 200, response.text
+        result = _rpc_result(response)
+        assert result["isError"] is True
+        assert result["content"][0]["text"] == (
+            "Error: The key is not allowed to access the requested MCP servers: math_restricted"
+        )
+        async with asyncio.timeout(10):
+            while True:
+                payload = json.loads(await asyncio.to_thread(proxy_call_recorder.failures.get, True, 5))
+                if payload["id"] == "proxy-scope-denial":
+                    break
+        assert payload["call_type"] == "call_mcp_tool"
+        assert payload["status"] == "failure"
+        assert payload["response_cost"] == 0
+        assert "math_restricted" in payload["error_str"]
+
+    @pytest.mark.parametrize("arguments", ["wrong", False, None, [], 0])
+    def test_handler_rejects_non_object_arguments(
+        self, proxy_server_url: str, _proxy_server: ProxyRig, arguments: object
+    ) -> None:
+        async def check() -> None:
+            auth = UserAPIKeyAuth(
+                object_permission=LiteLLM_ObjectPermissionTable(
+                    object_permission_id="validation", mcp_servers=["math_stdio"]
+                )
+            )
+            hits = _payload(await handle_mcp_proxy_tool("search_tools", {"query": "add"}, auth))
+            tool_id = next(hit["tool_id"] for hit in hits if hit["name"] == "math_stdio-add")
+            result = await handle_mcp_proxy_tool("call_tool", {"tool_id": tool_id, "arguments": arguments}, auth)
+            assert result.isError is True
+            assert result.content[0].text == "arguments must be an object"
+
+        asyncio.run_coroutine_threadsafe(check(), _proxy_server.loop).result(timeout=30)
diff --git a/tests/pass_through_unit_tests/test_claude_code_marketplace.py b/tests/pass_through_unit_tests/test_claude_code_marketplace.py
index 2ca81f1d5d3..bedb8830559 100644
--- a/tests/pass_through_unit_tests/test_claude_code_marketplace.py
+++ b/tests/pass_through_unit_tests/test_claude_code_marketplace.py
@@ -216,7 +216,7 @@ async def test_get_marketplace(mock_prisma_client):
     )
 
     # Now get the marketplace
-    response = await get_marketplace()
+    response = await get_marketplace(request=MagicMock())
 
     # Response is a JSONResponse, get the body
     body = json.loads(response.body.decode())
diff --git a/tests/proxy_unit_tests/test_custom_tokenizer_bug.py b/tests/proxy_unit_tests/test_custom_tokenizer_bug.py
index 89899d3e762..c4b1f4f3afd 100644
--- a/tests/proxy_unit_tests/test_custom_tokenizer_bug.py
+++ b/tests/proxy_unit_tests/test_custom_tokenizer_bug.py
@@ -23,9 +23,9 @@ from litellm.proxy.proxy_server import token_counter
 
 def _fake_hf_tokenizer(num_tokens: int) -> MagicMock:
     encoding = MagicMock()
-    encoding.ids = list(range(num_tokens))
+    encoding.__len__.return_value = num_tokens
     tokenizer = MagicMock()
-    tokenizer.encode.return_value = encoding
+    tokenizer.encode_batch_fast.return_value = [encoding]
     return tokenizer
 
 
@@ -68,13 +68,11 @@ async def test_custom_tokenizer_from_model_info_is_used(monkeypatch):
             )
         )
 
-    mock_tokenizer_cls.from_pretrained.assert_called_once_with(
-        "my-org/custom-tokenizer", revision="v2", auth_token=None
-    )
+    mock_tokenizer_cls.from_pretrained.assert_called_once_with("my-org/custom-tokenizer", revision="v2", token=None)
     assert response.tokenizer_type == "huggingface_tokenizer"
     assert response.request_model == "my-embedding-model"
     assert response.model_used == "self-hosted-embedder"
-    assert response.total_tokens > 0
+    assert response.total_tokens >= 7
 
 
 @pytest.mark.asyncio
diff --git a/tests/proxy_unit_tests/test_proxy_server.py b/tests/proxy_unit_tests/test_proxy_server.py
index 54cce9cdd78..d06eb0426c9 100644
--- a/tests/proxy_unit_tests/test_proxy_server.py
+++ b/tests/proxy_unit_tests/test_proxy_server.py
@@ -2920,7 +2920,7 @@ async def test_get_config_callbacks_with_all_types(client_no_auth):
         assert result["status"] == "success"
         assert "callbacks" in result
 
-        callbacks = result["callbacks"]
+        callbacks = [cb for cb in result["callbacks"] if not cb.get("read_only", False)]
 
         # Verify we have all 5 callbacks (2 success + 1 failure + 2 success_and_failure)
         assert len(callbacks) == 5
diff --git a/tests/proxy_unit_tests/test_response_polling_handler.py b/tests/proxy_unit_tests/test_response_polling_handler.py
index 772d3622745..467c1332325 100644
--- a/tests/proxy_unit_tests/test_response_polling_handler.py
+++ b/tests/proxy_unit_tests/test_response_polling_handler.py
@@ -14,13 +14,14 @@ These tests ensure the polling handler correctly manages response state
 following the OpenAI Response API format.
 """
 
+import asyncio
 import json
 from datetime import datetime, timezone
 from typing import Any, Dict, Optional
 from unittest.mock import AsyncMock, Mock, patch
 
 import pytest
-
+from fastapi import Request
 
 from litellm.proxy.response_polling.polling_handler import ResponsePollingHandler
 
@@ -1414,7 +1415,7 @@ def _make_background_streaming_kwargs(
         polling_id=polling_id,
         data={"model": "gpt-4o", "stream": False, "background": True},
         polling_handler=polling_handler,
-        request=Mock(),
+        request=Request({"type": "http", "method": "POST", "path": "/v1/responses", "headers": []}),
         fastapi_response=Mock(),
         user_api_key_dict=Mock(),
         general_settings={},
@@ -1663,6 +1664,63 @@ class TestBackgroundStreamingTerminalEvents:
         final_call = handler.update_state.call_args_list[-1]
         assert final_call.kwargs["status"] == "completed"
 
+    @pytest.mark.asyncio
+    async def test_polling_client_disconnect_does_not_cancel_upstream_call(self):
+        """The polling client hangs up right after getting its polling id. The detached task
+        must still stream the upstream response through the client-disconnect guards."""
+        from litellm.proxy.common_request_processing import create_response
+        from litellm.proxy.response_polling.background_streaming import (
+            background_streaming_task,
+        )
+
+        async def client_already_left():
+            return {"type": "http.disconnect"}
+
+        async def slow_upstream_stream():
+            await asyncio.sleep(0.05)
+            for event in (
+                {"type": "response.in_progress"},
+                {
+                    "type": "response.completed",
+                    "response": {
+                        "id": "resp_123",
+                        "status": "completed",
+                        "usage": {"input_tokens": 13, "output_tokens": 10},
+                        "model": "gpt-4o",
+                        "output": [{"id": "item_1", "type": "message"}],
+                    },
+                },
+            ):
+                yield f"data: {json.dumps(event)}\n\n"
+
+        async def upstream_call_behind_disconnect_guard(**kwargs):
+            return await create_response(
+                slow_upstream_stream(), "text/event-stream", {}, request=kwargs["request"]
+            )
+
+        handler = AsyncMock(spec=ResponsePollingHandler)
+        kwargs = _make_background_streaming_kwargs("poll_7", handler)
+        kwargs["request"] = Request(
+            {
+                "type": "http",
+                "method": "POST",
+                "path": "/v1/responses",
+                "headers": [(b"x-litellm-call-id", b"call-123")],
+                "query_string": b"",
+            },
+            client_already_left,
+        )
+
+        with patch(  # test-quality-ok: the processor is built inside the task, same idiom as the sibling tests
+            "litellm.proxy.response_polling.background_streaming.ProxyBaseLLMRequestProcessing"
+        ) as MockProcessor:
+            MockProcessor.return_value.base_process_llm_request = upstream_call_behind_disconnect_guard
+            await background_streaming_task(**kwargs)
+
+        final_call = handler.update_state.call_args_list[-1]
+        assert final_call.kwargs["status"] == "completed"
+        assert final_call.kwargs["usage"] == {"input_tokens": 13, "output_tokens": 10}
+
 
 class TestEdgeCases:
     """Test edge cases and error scenarios"""
diff --git a/tests/store_model_in_db_tests/test_openai_error_handling.py b/tests/store_model_in_db_tests/test_openai_error_handling.py
index d3f38f93bf3..5de7c427d19 100644
--- a/tests/store_model_in_db_tests/test_openai_error_handling.py
+++ b/tests/store_model_in_db_tests/test_openai_error_handling.py
@@ -193,7 +193,7 @@ async def test_chat_completion_bad_model_with_spend_logs():
 
         # Verify the structure of the log entry
         assert log_entry["request_id"] == litellm_call_id
-        assert log_entry["model"] == "non-existent-model"
+        assert log_entry["model"] == "unknown-model"
         assert log_entry["model_group"] in ("", "non-existent-model")
         assert log_entry["spend"] == 0.0
         assert log_entry["total_tokens"] == 0
diff --git a/tests/test_gateway/test_launch.py b/tests/test_gateway/test_launch.py
new file mode 100644
index 00000000000..a783ce6ac7e
--- /dev/null
+++ b/tests/test_gateway/test_launch.py
@@ -0,0 +1,202 @@
+import os
+import socket
+import sys
+import textwrap
+import urllib.parse
+from collections.abc import Iterator
+from pathlib import Path
+from typing import Final, cast
+from unittest.mock import MagicMock, patch
+
+import pytest
+from uvicorn.importer import import_from_string
+from uvicorn.main import main as uvicorn_main
+
+import gateway.main
+from gateway.launch import GATEWAY_APP, main, pool_database_url, uvicorn_argv
+from litellm.proxy.db.db_url_settings import DatabaseURLSettings
+from litellm.proxy.db.pgbouncer import PGBOUNCER_POOLED_ENV_VAR, PgBouncerError, PgBouncerSettings
+
+DB_ENV: Final = {
+    "DATABASE_HOST": "db.internal",
+    "DATABASE_PORT": "5432",
+    "DATABASE_USER": "litellm_pool",
+    "DATABASE_NAME": "litellm",
+    "DATABASE_PASSWORD": "p@ss",
+}
+
+
+def _free_port() -> int:
+    with socket.socket() as probe:
+        probe.bind(("127.0.0.1", 0))
+        return cast(tuple[str, int], probe.getsockname())[1]
+
+
+def _fake_pooler(tmp_path: Path) -> Path:
+    script: Final = tmp_path / "fake-pgbouncer"
+    script.write_text(
+        textwrap.dedent(
+            f"""\
+            #!{sys.executable}
+            import configparser, select, socket, sys
+            if sys.argv[1:] == ["--version"]:
+                print("PgBouncer 1.25.2")
+                sys.exit(0)
+            ini = configparser.ConfigParser()
+            ini.read(sys.argv[1])
+            port = ini.getint("pgbouncer", "listen_port")
+            tcp = socket.socket()
+            tcp.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+            tcp.bind(("127.0.0.1", port))
+            tcp.listen()
+            unix = socket.socket(socket.AF_UNIX)
+            unix.bind(ini.get("pgbouncer", "unix_socket_dir") + f"/.s.PGSQL.{{port}}")
+            unix.listen()
+            while True:
+                for ready in select.select([tcp, unix], [], [])[0]:
+                    ready.accept()[0].close()
+            """
+        )
+    )
+    script.chmod(0o700)
+    return script
+
+
+def _query(url: str) -> dict[str, str]:
+    return dict(urllib.parse.parse_qsl(urllib.parse.urlsplit(url).query))
+
+
+@pytest.fixture
+def password_env(monkeypatch: pytest.MonkeyPatch) -> Iterator[dict[str, str]]:
+    for var in (
+        "DATABASE_URL",
+        "IAM_TOKEN_DB_AUTH",
+        "AZURE_POSTGRESQL_AUTH",
+        "DATABASE_HOST_READ_REPLICA",
+        PGBOUNCER_POOLED_ENV_VAR,
+    ):
+        monkeypatch.setenv(var, "")
+        monkeypatch.delenv(var)
+    for var, value in DB_ENV.items():
+        monkeypatch.setenv(var, value)
+    yield dict(DB_ENV)
+    os.environ.pop("DATABASE_URL", None)
+
+
+def _minted_iam_token(token: str):
+    rds: Final = MagicMock()
+    rds.generate_db_auth_token.return_value = token
+    return patch("boto3.client", return_value=rds)
+
+
+def _uvicorn_params(argv: tuple[str, ...]) -> dict[str, object]:
+    return uvicorn_main.make_context("uvicorn", list(argv)).params
+
+
+class TestUvicornArgv:
+    def test_keepalive_env_reaches_uvicorn(self):
+        params: Final = _uvicorn_params(uvicorn_argv(("--workers", "4"), {"KEEPALIVE_TIMEOUT": "75"}))
+        assert params["app"] == GATEWAY_APP
+        assert params["workers"] == 4
+        assert params["timeout_keep_alive"] == 75
+
+    def test_unset_env_keeps_the_uvicorn_default(self):
+        assert _uvicorn_params(uvicorn_argv(("--workers", "4"), {}))["timeout_keep_alive"] == 5
+
+    def test_an_explicit_flag_wins_over_the_env(self):
+        argv: Final = uvicorn_argv(("--timeout-keep-alive", "30"), {"KEEPALIVE_TIMEOUT": "75"})
+        assert _uvicorn_params(argv)["timeout_keep_alive"] == 30
+
+    def test_the_app_uvicorn_is_told_to_serve_is_the_trimmed_gateway(self):
+        assert import_from_string(cast(str, _uvicorn_params(uvicorn_argv((), {}))["app"])) is gateway.main.app
+
+
+class TestPoolDatabaseUrl:
+    def test_a_disabled_pooler_yields_no_url_to_install(self, password_env: dict[str, str]):
+        settings: Final = DatabaseURLSettings.from_env()
+        settings.apply_to_env()
+        environ: Final = {"DATABASE_URL": "postgresql://litellm_pool:p%40ss@db.internal:5432/litellm"}
+        assert pool_database_url(settings, PgBouncerSettings(enabled=False), environ) is None
+
+    def test_a_missing_upstream_url_is_reported(self, password_env: dict[str, str]):
+        environ: Final[dict[str, str]] = {}
+        outcome: Final = pool_database_url(DatabaseURLSettings.from_env(), PgBouncerSettings(enabled=True), environ)
+        assert isinstance(outcome, PgBouncerError)
+        assert "DATABASE_URL" in outcome.reason
+
+    def test_token_auth_hands_the_workers_the_pool_user_not_the_token(
+        self, password_env: dict[str, str], monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+    ):
+        monkeypatch.setenv("IAM_TOKEN_DB_AUTH", "true")
+        monkeypatch.setenv("AWS_REGION_NAME", "us-east-1")
+        port: Final = _free_port()
+        environ: Final = {"DATABASE_URL": "postgresql://litellm:MINTED_TOKEN@db.internal:5432/litellm"}
+        with _minted_iam_token("MINTED_TOKEN"):
+            outcome: Final = pool_database_url(
+                DatabaseURLSettings.from_env(),
+                PgBouncerSettings(enabled=True, port=port, binary=str(_fake_pooler(tmp_path))),
+                environ,
+            )
+        assert isinstance(outcome, str), outcome
+        pooled: Final = urllib.parse.urlsplit(outcome)
+        assert (pooled.username, pooled.hostname, pooled.port) == ("litellm_pgbouncer", "127.0.0.1", port)
+        assert "MINTED_TOKEN" not in outcome
+
+
+class TestMain:
+    def test_workers_inherit_the_loopback_url_the_supervisor_installed(
+        self, password_env: dict[str, str], monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+    ):
+        port: Final = _free_port()
+        monkeypatch.setenv("LITELLM_PGBOUNCER_ENABLED", "true")
+        monkeypatch.setenv("LITELLM_PGBOUNCER_PORT", str(port))
+        monkeypatch.setenv("LITELLM_PGBOUNCER_BINARY", str(_fake_pooler(tmp_path)))
+        monkeypatch.setenv("KEEPALIVE_TIMEOUT", "75")
+        served: Final[list[tuple[str, ...]]] = []
+        main(("--workers", "4"), serve=lambda argv: served.append(tuple(argv)))
+
+        pooled: Final = os.environ["DATABASE_URL"]
+        assert urllib.parse.urlsplit(pooled).hostname == "127.0.0.1"
+        assert urllib.parse.urlsplit(pooled).port == port
+        assert urllib.parse.urlsplit(pooled).username == "litellm_pgbouncer"
+        assert "p%40ss" not in pooled
+        assert _query(pooled)["pgbouncer"] == "true"
+        assert _uvicorn_params(served[0])["timeout_keep_alive"] == 75
+
+        DatabaseURLSettings.from_env().apply_to_env()
+        assert urllib.parse.urlsplit(os.environ["DATABASE_URL"]).netloc == urllib.parse.urlsplit(pooled).netloc
+        assert _query(os.environ["DATABASE_URL"])["pgbouncer"] == "true"
+
+    def test_iam_workers_keep_the_loopback_url_instead_of_minting_their_own(
+        self, password_env: dict[str, str], monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+    ):
+        port: Final = _free_port()
+        monkeypatch.delenv("DATABASE_PASSWORD")
+        monkeypatch.setenv("IAM_TOKEN_DB_AUTH", "true")
+        monkeypatch.setenv("AWS_REGION_NAME", "us-east-1")
+        monkeypatch.setenv("LITELLM_PGBOUNCER_ENABLED", "true")
+        monkeypatch.setenv("LITELLM_PGBOUNCER_PORT", str(port))
+        monkeypatch.setenv("LITELLM_PGBOUNCER_BINARY", str(_fake_pooler(tmp_path)))
+        served: Final[list[tuple[str, ...]]] = []
+        with _minted_iam_token("SUPERVISOR_TOKEN"):
+            main(("--workers", "4"), serve=lambda argv: served.append(tuple(argv)))
+        pooled: Final = os.environ["DATABASE_URL"]
+        assert urllib.parse.urlsplit(pooled).netloc.endswith(f"@127.0.0.1:{port}")
+        assert "SUPERVISOR_TOKEN" not in pooled
+        assert os.environ[PGBOUNCER_POOLED_ENV_VAR] == "true"
+        assert len(served) == 1
+
+        with _minted_iam_token("WORKER_TOKEN"):
+            DatabaseURLSettings.from_env().apply_to_env()
+        assert os.environ["DATABASE_URL"] == pooled
+
+    def test_a_pooler_that_cannot_start_stops_the_gateway_before_uvicorn(
+        self, password_env: dict[str, str], monkeypatch: pytest.MonkeyPatch, tmp_path: Path
+    ):
+        monkeypatch.setenv("LITELLM_PGBOUNCER_ENABLED", "true")
+        monkeypatch.setenv("LITELLM_PGBOUNCER_BINARY", str(tmp_path / "missing-pgbouncer"))
+        served: Final[list[tuple[str, ...]]] = []
+        with pytest.raises(SystemExit) as stopped:
+            main(("--workers", "4"), serve=lambda argv: served.append(tuple(argv)))
+        assert "missing-pgbouncer" in str(stopped.value)
+        assert served == []
diff --git a/tests/test_litellm/caching/test_caching_handler.py b/tests/test_litellm/caching/test_caching_handler.py
index 8e0bc200012..071b99850f6 100644
--- a/tests/test_litellm/caching/test_caching_handler.py
+++ b/tests/test_litellm/caching/test_caching_handler.py
@@ -658,3 +658,38 @@ def test_async_cache_write_completes_when_asyncio_run_closes_the_loop(monkeypatc
     asyncio.run(_short_lived_script())
 
     assert len(writes) == 1
+
+
+@pytest.mark.asyncio
+async def test_cache_hit_records_the_looked_up_key_as_the_preset_cache_key(monkeypatch):
+    """The spend log for a cache hit must reuse the key the lookup already computed instead of hashing again."""
+    import litellm
+    from litellm.caching.caching import Cache
+    from litellm.types.utils import CallTypes
+
+    async def acompletion(**kwargs):
+        return None
+
+    monkeypatch.setattr(litellm, "cache", Cache(type="local"))
+    kwargs = {"model": "gpt-5.4", "messages": [{"role": "user", "content": "hello"}], "caching": True}
+    await litellm.cache.async_add_cache(
+        litellm.ModelResponse(choices=[{"message": {"role": "assistant", "content": "hi"}}]), **kwargs
+    )
+    handler = LLMCachingHandler(original_function=acompletion, request_kwargs=kwargs, start_time=datetime.now())
+    logging_obj = _build_logging_obj(CallTypes.acompletion.value, stream=False)
+    logging_obj.async_success_handler = AsyncMock()
+
+    hit = await handler._async_get_cache(
+        model="gpt-5.4",
+        original_function=acompletion,
+        logging_obj=logging_obj,
+        start_time=datetime.now(),
+        call_type=CallTypes.acompletion.value,
+        kwargs=kwargs,
+        args=(),
+    )
+
+    assert hit is not None and hit.cached_result is not None
+    assert handler.preset_cache_key is not None
+    assert logging_obj.litellm_params["preset_cache_key"] == handler.preset_cache_key
+    assert hit.cached_result._hidden_params["cache_key"] == handler.preset_cache_key
diff --git a/tests/test_litellm/caching/test_dual_cache.py b/tests/test_litellm/caching/test_dual_cache.py
index ded3be26630..4c9068722b8 100644
--- a/tests/test_litellm/caching/test_dual_cache.py
+++ b/tests/test_litellm/caching/test_dual_cache.py
@@ -1,4 +1,5 @@
 import asyncio
+import logging
 import time
 import uuid
 from unittest.mock import AsyncMock, MagicMock, patch
@@ -7,7 +8,8 @@ import pytest
 
 from litellm.caching.dual_cache import DualCache
 from litellm.caching.in_memory_cache import InMemoryCache
-from litellm.caching.redis_cache import RedisCache
+from litellm.caching.redis_cache import RedisCache, _redis_circuit_breaker_guard, _redis_circuit_breaker_guard_sync
+from litellm.types.caching import RedisPipelineIncrementOperation
 
 
 @pytest.mark.asyncio
@@ -576,3 +578,129 @@ async def test_dual_cache_late_attach_redis_wires_writes_and_ttl_async():
     assert mock_redis.async_set_cache.call_args[0][:2] == (key_after, val_after)
 
     assert in_memory.get_cache(key_after) == val_after
+
+
+class _OpenBreakerRedis:
+    def __init__(self) -> None:
+        from litellm.caching.redis_cache import RedisCircuitBreaker
+
+        self._circuit_breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+        for _ in range(3):
+            self._circuit_breaker.record_failure()
+
+    @_redis_circuit_breaker_guard
+    async def async_get_cache(self, key, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard
+    async def async_batch_get_cache(self, key_list, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard
+    async def async_set_cache(self, key, value, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard
+    async def async_set_cache_pipeline(self, cache_list, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard
+    async def async_increment_pipeline(self, increment_list, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard
+    async def async_increment(self, key, value, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard_sync
+    def get_cache(self, key, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard_sync
+    def batch_get_cache(self, key_list, **kwargs):
+        raise AssertionError("never reached")
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "call",
+    [
+        lambda cache: cache.async_get_cache("k"),
+        lambda cache: cache.async_batch_get_cache(["k1", "k2"]),
+        lambda cache: cache.async_set_cache("k", "v"),
+        lambda cache: cache.async_set_cache_pipeline([("k", "v")]),
+        lambda cache: cache.async_increment_cache_pipeline(
+            increment_list=[RedisPipelineIncrementOperation(key="k", increment_value=1.0, ttl=60)]
+        ),
+        lambda cache: cache.async_increment_cache("k", 1.0),
+    ],
+    ids=["get", "batch_get", "set", "set_pipeline", "increment_pipeline", "increment"],
+)
+async def test_an_open_circuit_breaker_is_not_an_error_per_request(caplog, call):
+    cache = DualCache(in_memory_cache=InMemoryCache(), redis_cache=_OpenBreakerRedis())  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    caplog.clear()
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM"):
+        await call(cache)
+
+    assert [record.levelno for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert any("circuit breaker is open" in record.getMessage() for record in caplog.records)
+
+
+@pytest.mark.parametrize(
+    "call",
+    [lambda cache: cache.get_cache("k"), lambda cache: cache.batch_get_cache(["k1", "k2"])],
+    ids=["get", "batch_get"],
+)
+def test_an_open_circuit_breaker_is_not_an_error_per_sync_request(caplog, call):
+    cache = DualCache(in_memory_cache=InMemoryCache(), redis_cache=_OpenBreakerRedis())  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    caplog.clear()
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM"):
+        call(cache)
+
+    assert [record.levelno for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert any("circuit breaker is open" in record.getMessage() for record in caplog.records)
+
+
+@pytest.mark.asyncio
+async def test_a_real_redis_failure_still_logs_an_error(caplog):
+    class _BrokenRedis:
+        async def async_get_cache(self, key, **kwargs):
+            raise ConnectionError("redis is down")
+
+    cache = DualCache(in_memory_cache=InMemoryCache(), redis_cache=_BrokenRedis())  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM"):
+        assert await cache.async_get_cache("k") is None
+
+    errors = [record for record in caplog.records if record.levelno == logging.ERROR]
+    assert [record.getMessage() for record in errors] == ["LiteLLM Cache: exception in async_get_cache: redis is down"]
+    assert errors[0].exc_info is not None
+
+
+def _dual_cache_with_open_breaker_and_a_memory_hit() -> DualCache:
+    in_memory = InMemoryCache()
+    in_memory.set_cache("k1", "v1")
+    return DualCache(in_memory_cache=in_memory, redis_cache=_OpenBreakerRedis(), default_redis_batch_cache_expiry=10)  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+
+
+def test_open_breaker_keeps_sync_batch_read_memory_hits_and_releases_reservations():
+    """A refused Redis batch read must still answer with the in-memory hits and hold no reservation.
+
+    The refusal was logged and turned into a bare None, so a caller lost its in-memory hits
+    for as long as the breaker stayed open, and the reserved keys stayed throttled until
+    the batch expiry passed even though nothing was ever read for them.
+    """
+    cache = _dual_cache_with_open_breaker_and_a_memory_hit()
+
+    assert list(cache.batch_get_cache(["k1", "k2"])) == ["v1", None]
+    assert "k2" not in cache.last_redis_batch_access_time
+
+
+@pytest.mark.asyncio
+async def test_open_breaker_keeps_async_batch_read_memory_hits_and_releases_reservations():
+    cache = _dual_cache_with_open_breaker_and_a_memory_hit()
+
+    assert list(await cache.async_batch_get_cache(["k1", "k2"])) == ["v1", None]
+    assert "k2" not in cache.last_redis_batch_access_time
diff --git a/tests/test_litellm/caching/test_redis_cache.py b/tests/test_litellm/caching/test_redis_cache.py
index 6b2df118611..bcae33b976e 100644
--- a/tests/test_litellm/caching/test_redis_cache.py
+++ b/tests/test_litellm/caching/test_redis_cache.py
@@ -1,11 +1,12 @@
 import asyncio
+import time
 from collections.abc import Iterator
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
 
 from litellm._service_logger import ServiceLogging
-from litellm.caching.redis_cache import RedisCache
+from litellm.caching.redis_cache import RedisCache, RedisCircuitBreakerOpenError
 
 
 @pytest.fixture
@@ -515,14 +516,46 @@ async def test_circuit_breaker_opens_when_method_swallows_redis_failure(call_met
         await call_method(cache)
 
 
-def test_circuit_breaker_open_keeps_sync_batch_get_cache_as_a_miss(sync_batch_redis_cache):
-    """An open breaker must preserve the sync batch read's dictionary fallback."""
+def test_circuit_breaker_open_makes_sync_batch_get_cache_fast_fail(sync_batch_redis_cache, caplog):
+    """Once the breaker is open the sync batch read refuses with the typed error instead of a miss.
+
+    Swallowing the refusal into `{}` made every sync batch read on an open breaker emit an ERROR
+    log and a service failure event per call, and the DualCache caller could not tell the
+    refusal from a dead Redis, so it dropped its in-memory hits too.
+    """
     from litellm.constants import REDIS_CIRCUIT_BREAKER_FAILURE_THRESHOLD
 
     for _ in range(REDIS_CIRCUIT_BREAKER_FAILURE_THRESHOLD):
         assert sync_batch_redis_cache.batch_get_cache(key_list=["lit6729"]) == {}
 
-    assert sync_batch_redis_cache.batch_get_cache(key_list=["lit6729"]) == {}
+    caplog.clear()
+    with caplog.at_level("INFO"):
+        with pytest.raises(RedisCircuitBreakerOpenError):
+            sync_batch_redis_cache.batch_get_cache(key_list=["lit6729"])
+    sync_batch_redis_cache.redis_client.mget.assert_called()
+    assert caplog.records == []
+
+
+def test_sync_get_cache_failure_feeds_the_breaker_and_logs_a_well_formed_record(sync_batch_redis_cache, caplog):
+    """The sync get path swallowed its Redis error without recording it, and its log call was malformed.
+
+    `verbose_logger.error("...: ", e)` passes the exception as a format argument to a message
+    with no placeholder, so the record carried no error text. Nothing fed the breaker either,
+    so a dead Redis read through this path never opened it.
+    """
+    from litellm.constants import REDIS_CIRCUIT_BREAKER_FAILURE_THRESHOLD
+
+    sync_batch_redis_cache.redis_client.get.side_effect = OSError("redis unavailable")
+
+    with caplog.at_level("ERROR"):
+        for _ in range(REDIS_CIRCUIT_BREAKER_FAILURE_THRESHOLD):
+            assert sync_batch_redis_cache.get_cache("lit7468") is None
+
+    assert all("redis unavailable" in record.getMessage() for record in caplog.records)
+    assert len(caplog.records) == REDIS_CIRCUIT_BREAKER_FAILURE_THRESHOLD
+    assert sync_batch_redis_cache._circuit_breaker.is_open() is True
+    with pytest.raises(RedisCircuitBreakerOpenError):
+        sync_batch_redis_cache.get_cache("lit7468")
 
 
 def test_batch_get_counts_raises_where_batch_get_cache_reports_a_miss(sync_batch_redis_cache):
@@ -661,7 +694,8 @@ def test_sync_batch_get_cache_survives_a_service_callback_that_raises(
         with ThreadPoolExecutor(max_workers=1) as pool:
             assert pool.submit(cache.batch_get_cache, key_list=["lit6729"]).result() == {}
 
-    assert cache.batch_get_cache(key_list=["lit6729"]) == {}
+    with pytest.raises(RedisCircuitBreakerOpenError):
+        cache.batch_get_cache(key_list=["lit6729"])
 
 
 def test_call_stack_info_skips_breaker_guard_frames():
@@ -1010,6 +1044,161 @@ async def test_breaker_metrics_track_state_and_failure_class():
     assert sample("litellm_redis_circuit_breaker_state", {"state": "open"}) == open_gauge_before + 1
     assert sample("litellm_redis_circuit_breaker_state", {"state": "closed"}) == closed_gauge_before
 
+    breaker._opened_at = time.time() - 9999
+    assert breaker.is_open() is False
     breaker.record_success()
     assert sample("litellm_redis_circuit_breaker_state", {"state": "open"}) == open_gauge_before
     assert sample("litellm_redis_circuit_breaker_state", {"state": "closed"}) == closed_gauge_before + 1
+
+
+def test_sync_guard_counts_a_timeout_as_a_timeout():
+    from redis.exceptions import TimeoutError as RedisTimeoutError
+
+    from litellm.caching.redis_cache import RedisCircuitBreaker, _run_under_circuit_breaker_sync
+
+    breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60, timeout_min_duration=5.0)
+
+    def timing_out_call() -> str:
+        raise RedisTimeoutError("read timed out")
+
+    for _ in range(6):
+        with pytest.raises(RedisTimeoutError):
+            _run_under_circuit_breaker_sync(breaker, "op", timing_out_call)
+
+    assert breaker.is_open() is False
+
+
+def test_success_admitted_before_the_breaker_opened_cannot_close_it():
+    """A stale in-flight success must not close a breaker that opened while it ran.
+
+    Calls admitted while the breaker was still closed finish after later failures opened it.
+    Recording their success unconditionally closed the breaker again, skipping the recovery
+    timeout and the single half-open probe, so the breaker flapped between open and closed
+    on every straggler while Redis was still down.
+    """
+    from litellm.caching.redis_cache import RedisCircuitBreaker
+
+    breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+    for _ in range(3):
+        breaker.record_failure()
+    assert breaker._state == breaker.OPEN
+
+    breaker.record_success()
+
+    assert breaker._state == breaker.OPEN
+    assert breaker.is_open() is True
+
+
+def test_recovery_probe_still_closes_the_breaker():
+    from litellm.caching.redis_cache import RedisCircuitBreaker
+
+    breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+    for _ in range(3):
+        breaker.record_failure()
+    breaker._opened_at = time.time() - 9999
+    assert breaker.is_open() is False
+    assert breaker._state == breaker.HALF_OPEN
+
+    breaker.record_success()
+
+    assert breaker._state == breaker.CLOSED
+    assert breaker.is_open() is False
+
+
+@pytest.mark.asyncio
+async def test_stale_success_during_the_recovery_probe_leaves_the_breaker_to_the_probe():
+    """A call admitted before the trip that finishes while HALF_OPEN must not close the breaker.
+
+    Only the one call designated as the recovery probe has actually reached Redis after the
+    outage, so closing on the straggler's success resumed full Redis traffic before the probe
+    had proven anything.
+    """
+    from litellm.caching.redis_cache import RedisCircuitBreaker, _run_under_circuit_breaker
+
+    breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+    stale_admitted = asyncio.Event()
+    stale_release = asyncio.Event()
+    probe_admitted = asyncio.Event()
+    probe_release = asyncio.Event()
+
+    async def stale_call() -> str:
+        stale_admitted.set()
+        await stale_release.wait()
+        return "stale"
+
+    async def probe_call() -> str:
+        probe_admitted.set()
+        await probe_release.wait()
+        return "probe"
+
+    stale = asyncio.ensure_future(_run_under_circuit_breaker(breaker, "op", stale_call))
+    await stale_admitted.wait()
+    for _ in range(3):
+        breaker.record_failure()
+    assert breaker._state == breaker.OPEN
+    breaker._opened_at = time.time() - 9999
+    probe = asyncio.ensure_future(_run_under_circuit_breaker(breaker, "op", probe_call))
+    await probe_admitted.wait()
+    assert breaker._state == breaker.HALF_OPEN
+
+    stale_release.set()
+    assert await stale == "stale"
+
+    assert breaker._state == breaker.HALF_OPEN, "the straggler must not close the breaker for the probe"
+    assert breaker.is_open() is True
+
+    probe_release.set()
+    assert await probe == "probe"
+
+    assert breaker._state == breaker.CLOSED
+    assert breaker.is_open() is False
+
+
+@pytest.mark.asyncio
+async def test_a_probe_overtaken_by_a_later_outage_leaves_the_breaker_to_the_new_probe():
+    """A probe still in flight when a late failure reopens the breaker must not close it for the next probe.
+
+    Once the breaker has reopened, only the probe admitted after that outage has reached
+    Redis, so the older probe's success no longer says anything about whether Redis recovered.
+    """
+    from litellm.caching.redis_cache import RedisCircuitBreaker, _run_under_circuit_breaker
+
+    breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+    old_probe_admitted = asyncio.Event()
+    old_probe_release = asyncio.Event()
+    new_probe_admitted = asyncio.Event()
+    new_probe_release = asyncio.Event()
+
+    async def old_probe_call() -> str:
+        old_probe_admitted.set()
+        await old_probe_release.wait()
+        return "old probe"
+
+    async def new_probe_call() -> str:
+        new_probe_admitted.set()
+        await new_probe_release.wait()
+        return "new probe"
+
+    for _ in range(3):
+        breaker.record_failure()
+    breaker._opened_at = time.time() - 9999
+    old_probe = asyncio.ensure_future(_run_under_circuit_breaker(breaker, "op", old_probe_call))
+    await old_probe_admitted.wait()
+    assert breaker._state == breaker.HALF_OPEN
+
+    breaker.record_failure()
+    assert breaker._state == breaker.OPEN
+    breaker._opened_at = time.time() - 9999
+    new_probe = asyncio.ensure_future(_run_under_circuit_breaker(breaker, "op", new_probe_call))
+    await new_probe_admitted.wait()
+    assert breaker._state == breaker.HALF_OPEN
+
+    old_probe_release.set()
+    assert await old_probe == "old probe"
+
+    assert breaker._state == breaker.HALF_OPEN, "the overtaken probe must not close the breaker for the new probe"
+    assert breaker.is_open() is True
+
+    new_probe_release.set()
+    assert await new_probe == "new probe"
+    assert breaker._state == breaker.CLOSED
diff --git a/tests/test_litellm/enterprise/proxy/test_managed_files_hook.py b/tests/test_litellm/enterprise/proxy/test_managed_files_hook.py
index 091b958d7c3..48fceb50403 100644
--- a/tests/test_litellm/enterprise/proxy/test_managed_files_hook.py
+++ b/tests/test_litellm/enterprise/proxy/test_managed_files_hook.py
@@ -1095,6 +1095,110 @@ async def test_afile_content_passes_trusted_model_credentials_to_router():
     assert trusted_credentials["s3_bucket_name"] == "my-bucket"
 
 
+def _managed_deletion_file_id(provider_file_id):
+    from litellm.types.utils import SpecialEnums
+
+    value = SpecialEnums.LITELLM_MANAGED_FILE_COMPLETE_STR.value.format(
+        "application/json", "test-file", "batch-model", provider_file_id, "model-123"
+    )
+    return base64.urlsafe_b64encode(value.encode()).decode().rstrip("=")
+
+
+def _managed_files_with_deletion_row(unified_file_id, provider_file_id, file_object):
+    from litellm.caching import DualCache
+    from litellm.models.managed_files import LiteLLM_ManagedFileTable
+    from litellm_enterprise.proxy.hooks.managed_files import _PROXY_LiteLLMManagedFiles
+
+    row = LiteLLM_ManagedFileTable(
+        unified_file_id=unified_file_id,
+        model_mappings={"model-123": provider_file_id},
+        flat_model_file_ids=[provider_file_id],
+        file_object=file_object,
+    )
+    table = MagicMock(
+        find_first=AsyncMock(return_value=row),
+        delete=AsyncMock(),
+    )
+    return _PROXY_LiteLLMManagedFiles(
+        internal_usage_cache=DualCache(),
+        prisma_client=MagicMock(db=MagicMock(litellm_managedfiletable=table)),
+    ), table
+
+
+@pytest.mark.asyncio
+async def test_afile_delete_bedrock_uses_deployment_bucket_and_signed_s3_delete(monkeypatch):
+    import httpx
+    import respx
+
+    from litellm import Router
+
+    monkeypatch.delenv("AWS_S3_BUCKET_NAME", raising=False)
+    monkeypatch.delenv("AWS_S3_OUTPUT_BUCKET_NAME", raising=False)
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    router = Router(
+        model_list=[
+            {
+                "model_name": "bedrock-batch",
+                "litellm_params": {
+                    "model": "bedrock/us.anthropic.claude-haiku-4-5-20251001-v1:0",
+                    "aws_access_key_id": "AKIAEXAMPLE",
+                    "aws_secret_access_key": "secret",
+                    "aws_region_name": "us-west-2",
+                    "s3_bucket_name": "my-bucket",
+                },
+                "model_info": {"id": "model-123"},
+            }
+        ],
+        num_retries=0,
+    )
+    s3_uri = "s3://my-bucket/litellm-bedrock-files/input.jsonl"
+    unified_file_id = _managed_deletion_file_id(s3_uri)
+    managed_files, table = _managed_files_with_deletion_row(unified_file_id, s3_uri, None)
+    with respx.mock:
+        route = respx.delete(
+            "https://s3.us-west-2.amazonaws.com/my-bucket/litellm-bedrock-files/input.jsonl"
+        ).mock(return_value=httpx.Response(204))
+        response = await managed_files.afile_delete(
+            file_id=unified_file_id,
+            litellm_parent_otel_span=None,
+            llm_router=router,
+            _litellm_internal_model_credentials={"s3_bucket_name": "request-bucket"},
+        )
+
+    assert len(route.calls) == 1
+    assert route.calls[0].request.headers["Authorization"].startswith("AWS4-HMAC-SHA256")
+    assert response.id == unified_file_id
+    assert response.deleted is True
+    table.delete.assert_awaited_once_with(where={"unified_file_id": unified_file_id})
+
+
+@pytest.mark.asyncio
+async def test_afile_delete_returns_managed_id_for_stored_provider_output():
+    from openai.types import FileDeleted
+
+    provider_file_id = "file-error-output"
+    unified_file_id = _managed_deletion_file_id(provider_file_id)
+    stored_file = _make_file_object(provider_file_id)
+    managed_files, table = _managed_files_with_deletion_row(unified_file_id, provider_file_id, stored_file)
+    router = MagicMock(
+        get_deployment_credentials_with_provider=MagicMock(return_value=None),
+        afile_delete=AsyncMock(return_value=FileDeleted(id=provider_file_id, object="file", deleted=True)),
+    )
+    response = await managed_files.afile_delete(
+        file_id=unified_file_id,
+        litellm_parent_otel_span=None,
+        llm_router=router,
+        _litellm_internal_model_credentials={"s3_bucket_name": "request-bucket"},
+    )
+
+    assert response.id == unified_file_id
+    assert response.object == "file"
+    assert response.filename == stored_file.filename
+    assert stored_file.id == provider_file_id
+    router.afile_delete.assert_awaited_once_with(model="model-123", file_id=provider_file_id)
+    table.delete.assert_awaited_once_with(where={"unified_file_id": unified_file_id})
+
+
 @pytest.mark.asyncio
 async def test_afile_content_bedrock_unified_id_end_to_end(monkeypatch):
     """
diff --git a/tests/test_litellm/experimental_mcp_client/test_mcp_client.py b/tests/test_litellm/experimental_mcp_client/test_mcp_client.py
index 4db131da62c..713330a8280 100644
--- a/tests/test_litellm/experimental_mcp_client/test_mcp_client.py
+++ b/tests/test_litellm/experimental_mcp_client/test_mcp_client.py
@@ -1,25 +1,33 @@
 import asyncio
 import base64
+import json
 import os
 import sys
+from collections.abc import AsyncIterator
 from importlib import metadata
 from pathlib import Path
+from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import anyio
 import httpx
 import pytest
+import respx
 from litellm.proxy._experimental.mcp_server.outbound_credentials.httpx_auth import StaticHeaderAuth
 from mcp import McpError
+from mcp.client.streamable_http import streamable_http_client
+from pydantic import ValidationError
 from mcp.shared.message import SessionMessage
 from mcp.types import (
     LATEST_PROTOCOL_VERSION,
+    CallToolResult,
     ErrorData,
     Implementation,
     InitializeResult,
     JSONRPCError,
     JSONRPCMessage,
     JSONRPCResponse,
+    LoggingMessageNotificationParams,
     ServerCapabilities,
 )
 
@@ -29,8 +37,9 @@ import litellm.experimental_mcp_client.client as mcp_client_module
 from litellm.experimental_mcp_client.client import (
     MCP_STREAMABLE_HTTP_REQUIREMENT,
     MCPClient,
-    _as_read_timeout,
     _first_non_cancelled_cause,
+    _TransportContext,
+    as_mcp_read_timeout,
     missing_streamable_http_client_error,
     strip_auth_scheme,
 )
@@ -859,25 +868,25 @@ def _raise_mcp_error_while_handling_a_timeout(code: int, message: str) -> McpErr
         return raised
 
 
-def test_as_read_timeout_separates_the_sdk_timeout_from_a_relayed_upstream_error():
+def test_as_mcp_read_timeout_separates_the_sdk_timeout_from_a_relayed_upstream_error():
     """Neither signal alone is enough. The code alone cannot separate the SDK's own timeout from an
     upstream JSON-RPC error that happens to use 408, and the context chain alone cannot separate it
     from any other relayed error that surfaces while a timeout is being handled, so both must hold.
     """
     timeout_code = int(httpx.codes.REQUEST_TIMEOUT)
 
-    translated = _as_read_timeout(_raise_mcp_error_while_handling_a_timeout(timeout_code, "Timed out while waiting"))
+    translated = as_mcp_read_timeout(_raise_mcp_error_while_handling_a_timeout(timeout_code, "Timed out while waiting"))
     assert isinstance(translated, TimeoutError)
     assert str(translated) == "Timed out while waiting"
 
     relayed_408 = McpError(ErrorData(code=timeout_code, message="upstream said 408"))
-    assert _as_read_timeout(relayed_408) is None, "an upstream 408 with no elapsed timeout is not our timeout"
+    assert as_mcp_read_timeout(relayed_408) is None, "an upstream 408 with no elapsed timeout is not our timeout"
 
     relayed_other = _raise_mcp_error_while_handling_a_timeout(-32603, "upstream internal error")
-    assert _as_read_timeout(relayed_other) is None, "a non-timeout code is not our timeout, whatever the chain"
+    assert as_mcp_read_timeout(relayed_other) is None, "a non-timeout code is not our timeout, whatever the chain"
 
-    assert _as_read_timeout(McpError(ErrorData(code=-32603, message="boom"))) is None
-    assert _as_read_timeout(RuntimeError("not an McpError")) is None
+    assert as_mcp_read_timeout(McpError(ErrorData(code=-32603, message="boom"))) is None
+    assert as_mcp_read_timeout(RuntimeError("not an McpError")) is None
 
 
 @pytest.mark.asyncio
@@ -1224,14 +1233,14 @@ def test_without_a_configured_slot_the_existing_precedence_is_unchanged():
 
 
 _REDIRECT_CASES = [
-    ("https://upstream.example.com/mcp", "https://upstream.example.com/other"),      # same origin
+    ("https://upstream.example.com/mcp", "https://upstream.example.com/other"),  # same origin
     ("https://upstream.example.com/mcp", "https://upstream.example.com:443/other"),  # explicit default port
-    ("https://upstream.example.com/mcp", "https://attacker.example.com/collect"),    # different host
-    ("https://upstream.example.com/mcp", "http://upstream.example.com/collect"),     # scheme downgrade
-    ("https://upstream.example.com/mcp", "https://upstream.example.com:8443/other"), # different port
-    ("https://upstream.example.com/mcp", "https://sub.upstream.example.com/x"),      # different host
-    ("http://upstream.example.com/mcp", "https://upstream.example.com/other"),       # http -> https upgrade
-    ("http://upstream.example.com/mcp", "http://upstream.example.com/other"),        # same origin, plain http
+    ("https://upstream.example.com/mcp", "https://attacker.example.com/collect"),  # different host
+    ("https://upstream.example.com/mcp", "http://upstream.example.com/collect"),  # scheme downgrade
+    ("https://upstream.example.com/mcp", "https://upstream.example.com:8443/other"),  # different port
+    ("https://upstream.example.com/mcp", "https://sub.upstream.example.com/x"),  # different host
+    ("http://upstream.example.com/mcp", "https://upstream.example.com/other"),  # http -> https upgrade
+    ("http://upstream.example.com/mcp", "http://upstream.example.com/other"),  # same origin, plain http
 ]
 
 
@@ -1283,3 +1292,606 @@ def test_a_differently_cased_injected_header_cannot_shadow_the_slot() -> None:
     headers = client._get_auth_headers()
     assert [v for k, v in headers.items() if k.lower() == "esb-oauth"] == ["Bearer minted-token"]
     assert headers["X-Trace"] == "keep"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("content_type", "body", "expected_type"),
+    [
+        ("text/html", b"<html>secret-page</html>", ValueError),
+        ("application/json", b"secret-invalid-json", ValidationError),
+        ("application/json", b"", ValidationError),
+        ("application/json", b'{"secret":"invalid-rpc"}', ValidationError),
+        ("application/json", b'{"jsonrpc":"2.0","id":0,"result":{"secret":"invalid-schema"}}', ValidationError),
+    ],
+)
+async def test_invalid_http_response_surfaces_without_waiting_for_timeout(
+    content_type: str, body: bytes, expected_type: type[Exception]
+) -> None:
+    from litellm.proxy._experimental.mcp_server.rest_endpoints import _connection_error_message
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, headers={"Content-Type": content_type}, content=body)
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        client: Final = MCPClient(server_url="https://example.com/mcp", timeout=30)
+        with pytest.raises(expected_type) as caught:
+            await asyncio.wait_for(
+                client._execute_session_operation(
+                    streamable_http_client(client.server_url, http_client=http_client),
+                    lambda session: session.list_tools(),
+                ),
+                timeout=3,
+            )
+
+    message: Final = _connection_error_message(caught.value, client.server_url, 30)
+    assert "unsupported content type" in message or "invalid MCP response" in message
+    assert "secret" not in message
+    assert "timed out" not in message
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("status_code", [200, 401, 503])
+async def test_http_response_handler_preserves_success_and_http_errors(status_code: int) -> None:
+    def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "DELETE":
+            return httpx.Response(200)
+        payload: Final = json.loads(request.content)
+        if "id" not in payload:
+            return httpx.Response(202)
+        result: Final = (
+            {
+                "protocolVersion": LATEST_PROTOCOL_VERSION,
+                "capabilities": {},
+                "serverInfo": {"name": "test", "version": "1"},
+            }
+            if payload["method"] == "initialize"
+            else {"tools": []}
+        )
+        return httpx.Response(status_code, json={"jsonrpc": "2.0", "id": payload["id"], "result": result})
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        client: Final = MCPClient(server_url="https://example.com/mcp", timeout=30)
+        operation: Final = client._execute_session_operation(
+            streamable_http_client(client.server_url, http_client=http_client), lambda session: session.list_tools()
+        )
+        if status_code == 200:
+            result: Final = await asyncio.wait_for(operation, timeout=3)
+            assert result.tools == []
+        else:
+            with pytest.raises(httpx.HTTPStatusError) as caught:
+                await asyncio.wait_for(operation, timeout=3)
+            assert caught.value.response.status_code == status_code
+
+
+@pytest.mark.asyncio
+async def test_http_response_handler_preserves_notifications_and_tool_listing() -> None:
+    notification: Final = {
+        "jsonrpc": "2.0",
+        "method": "notifications/message",
+        "params": {"level": "info", "data": "Listing tools"},
+    }
+    logging_callback: Final = AsyncMock()
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "DELETE":
+            return httpx.Response(200)
+        payload: Final = json.loads(request.content)
+        if "id" not in payload:
+            return httpx.Response(202)
+        if payload["method"] == "initialize":
+            return httpx.Response(
+                200,
+                json={
+                    "jsonrpc": "2.0",
+                    "id": payload["id"],
+                    "result": {
+                        "protocolVersion": LATEST_PROTOCOL_VERSION,
+                        "capabilities": {"logging": {}, "tools": {}},
+                        "serverInfo": {"name": "test", "version": "1"},
+                    },
+                },
+            )
+        response: Final = {
+            "jsonrpc": "2.0",
+            "id": payload["id"],
+            "result": {"tools": [{"name": "search", "inputSchema": {"type": "object"}}]},
+        }
+        return httpx.Response(
+            200,
+            headers={"Content-Type": "text/event-stream"},
+            content="".join(f"event: message\ndata: {json.dumps(message)}\n\n" for message in (notification, response)),
+        )
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        client: Final = MCPClient(server_url="https://example.com/mcp", timeout=30, logging_callback=logging_callback)
+        result: Final = await asyncio.wait_for(
+            client._execute_session_operation(
+                streamable_http_client(client.server_url, http_client=http_client), lambda session: session.list_tools()
+            ),
+            timeout=3,
+        )
+
+    assert [tool.name for tool in result.tools] == ["search"]
+    logging_callback.assert_awaited_once_with(LoggingMessageNotificationParams(level="info", data="Listing tools"))
+
+
+@pytest.mark.asyncio
+async def test_invalid_tool_list_schema_is_identified_as_an_upstream_response() -> None:
+    from litellm.proxy._experimental.mcp_server.rest_endpoints import _connection_error_message
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "DELETE":
+            return httpx.Response(200)
+        payload: Final = json.loads(request.content)
+        if "id" not in payload:
+            return httpx.Response(202)
+        result: Final = (
+            {
+                "protocolVersion": LATEST_PROTOCOL_VERSION,
+                "capabilities": {},
+                "serverInfo": {"name": "test", "version": "1"},
+            }
+            if payload["method"] == "initialize"
+            else {"tools": "secret-invalid-tools"}
+        )
+        return httpx.Response(200, json={"jsonrpc": "2.0", "id": payload["id"], "result": result})
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        client: Final = MCPClient(server_url="https://example.com/mcp", timeout=30)
+        with pytest.raises(ValidationError) as caught:
+            await asyncio.wait_for(
+                client._execute_session_operation(
+                    streamable_http_client(client.server_url, http_client=http_client),
+                    lambda session: session.list_tools(),
+                ),
+                timeout=3,
+            )
+
+    message: Final = _connection_error_message(caught.value, client.server_url, 30)
+    assert "invalid MCP response" in message
+    assert "secret" not in message
+
+
+class _DiagnosticSSEStream(httpx.AsyncByteStream):
+    def __init__(self, messages: asyncio.Queue[bytes | Exception | None]) -> None:
+        self.messages = messages
+
+    async def __aiter__(self) -> AsyncIterator[bytes]:
+        yield b"event: endpoint\ndata: /messages\n\n"
+        while True:
+            message: Final = await self.messages.get()
+            if message is None:
+                return
+            if isinstance(message, Exception):
+                raise message
+            yield b"event: message\ndata: " + message + b"\n\n"
+
+
+_DIAGNOSTIC_STDIO_SERVER: Final = """
+import json, sys
+mode, failure_method = sys.argv[1:]
+for line in sys.stdin:
+    request = json.loads(line)
+    if "method" not in request or "id" not in request:
+        continue
+    if request["method"] == failure_method:
+        if mode == "bad-json":
+            print("secret-invalid-json", flush=True)
+            continue
+        if mode == "closed":
+            sys.exit(0)
+        if mode == "silent":
+            print(json.dumps({"jsonrpc": "2.0", "method": "notifications/message", "params": {"level": "info", "data": "Waiting"}}), flush=True)
+            continue
+    if request["method"] == "initialize":
+        result = {"protocolVersion": request["params"]["protocolVersion"], "capabilities": {"tools": {}, "logging": {}}, "serverInfo": {"name": "diagnostic", "version": "1"}}
+    elif request["method"] == "tools/list":
+        print(json.dumps({"jsonrpc": "2.0", "method": "notifications/message", "params": {"level": "info", "data": "Listing tools"}}), flush=True)
+        print(json.dumps({"jsonrpc": "2.0", "id": "unmatched", "result": {}}), flush=True)
+        print(json.dumps({"jsonrpc": "2.0", "id": "server-ping", "method": "ping"}), flush=True)
+        result = {"tools": [{"name": "ping", "inputSchema": {"type": "object"}}]}
+    else:
+        result = {"content": [{"type": "text", "text": "pong"}], "isError": False}
+    print(json.dumps({"jsonrpc": "2.0", "id": request["id"], "result": result}), flush=True)
+"""
+
+
+def _diagnostic_transport(transport: MCPTransport, mode: str, failure_method: str) -> _TransportContext:
+    from mcp import StdioServerParameters
+    from mcp.client.sse import sse_client
+    from mcp.client.stdio import stdio_client
+
+    if transport == MCPTransport.stdio:
+        return stdio_client(
+            StdioServerParameters(
+                command=sys.executable, args=["-u", "-c", _DIAGNOSTIC_STDIO_SERVER, mode, failure_method]
+            )
+        )
+    messages: Final[asyncio.Queue[bytes | Exception | None]] = asyncio.Queue()
+
+    async def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "GET":
+            return httpx.Response(
+                200, headers={"Content-Type": "text/event-stream"}, stream=_DiagnosticSSEStream(messages)
+            )
+        payload: Final = json.loads(request.content)
+        if "method" not in payload or "id" not in payload:
+            return httpx.Response(202)
+        if payload["method"] == failure_method and mode != "ok":
+            if mode == "bad-json":
+                await messages.put(b"secret-invalid-json")
+            elif mode == "io-error":
+                await messages.put(httpx.ReadError("secret-read-error"))
+            elif mode == "closed":
+                await messages.put(None)
+            elif mode == "silent":
+                await messages.put(
+                    b'{"jsonrpc":"2.0","method":"notifications/message","params":{"level":"info","data":"Waiting"}}'
+                )
+            return httpx.Response(202)
+        if payload["method"] == "tools/list":
+            for message in (
+                {
+                    "jsonrpc": "2.0",
+                    "method": "notifications/message",
+                    "params": {"level": "info", "data": "Listing tools"},
+                },
+                {"jsonrpc": "2.0", "id": "unmatched", "result": {}},
+                {"jsonrpc": "2.0", "id": "server-ping", "method": "ping"},
+            ):
+                await messages.put(json.dumps(message).encode())
+        result: Final = (
+            {
+                "protocolVersion": LATEST_PROTOCOL_VERSION,
+                "capabilities": {"tools": {}, "logging": {}},
+                "serverInfo": {"name": "diagnostic", "version": "1"},
+            }
+            if payload["method"] == "initialize"
+            else {"tools": [{"name": "ping", "inputSchema": {"type": "object"}}]}
+            if payload["method"] == "tools/list"
+            else {"content": [{"type": "text", "text": "pong"}], "isError": False}
+        )
+        await messages.put(json.dumps({"jsonrpc": "2.0", "id": payload["id"], "result": result}).encode())
+        return httpx.Response(202)
+
+    def factory(
+        headers: dict[str, str] | None = None,
+        timeout: httpx.Timeout | None = None,
+        auth: httpx.Auth | None = None,
+    ) -> httpx.AsyncClient:
+        return httpx.AsyncClient(transport=httpx.MockTransport(respond), headers=headers, timeout=timeout, auth=auth)
+
+    return sse_client("https://example.com/sse", httpx_client_factory=factory)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("transport", [MCPTransport.sse, MCPTransport.stdio])
+@pytest.mark.parametrize("failure_method", ["initialize", "tools/list"])
+async def test_transport_parsing_failure_is_preserved(transport: MCPTransport, failure_method: str) -> None:
+    client: Final = MCPClient(server_url="https://example.com/sse", transport_type=transport, timeout=0.2)
+    with pytest.raises(ValidationError):
+        await asyncio.wait_for(
+            client._execute_session_operation(
+                _diagnostic_transport(transport, "bad-json", failure_method), lambda session: session.list_tools()
+            ),
+            timeout=3,
+        )
+
+
+@pytest.mark.asyncio
+async def test_sse_read_failure_is_preserved() -> None:
+    client: Final = MCPClient(server_url="https://example.com/sse", transport_type=MCPTransport.sse, timeout=0.2)
+    with pytest.raises(httpx.ReadError, match="secret-read-error"):
+        await asyncio.wait_for(
+            client._execute_session_operation(
+                _diagnostic_transport(MCPTransport.sse, "io-error", "tools/list"), lambda session: session.list_tools()
+            ),
+            timeout=3,
+        )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("transport", [MCPTransport.sse, MCPTransport.stdio])
+@pytest.mark.parametrize("mode", ["ok", "closed", "silent"])
+async def test_transport_completion_and_normal_messages(transport: MCPTransport, mode: str) -> None:
+    from mcp import ClientSession
+    from litellm.proxy._experimental.mcp_server.rest_endpoints import _connection_error_message
+
+    logging_callback: Final = AsyncMock()
+    client: Final = MCPClient(
+        server_url="https://example.com/sse", transport_type=transport, timeout=0.2, logging_callback=logging_callback
+    )
+
+    async def operation(session: ClientSession) -> CallToolResult:
+        tools: Final = await session.list_tools()
+        assert [tool.name for tool in tools.tools] == ["ping"]
+        return await session.call_tool("ping", {})
+
+    pending: Final = client._execute_session_operation(_diagnostic_transport(transport, mode, "tools/list"), operation)
+    if mode == "ok":
+        result: Final = await asyncio.wait_for(pending, timeout=3)
+        assert result.isError is False
+        assert result.content[0].text == "pong"
+        logging_callback.assert_awaited_once_with(LoggingMessageNotificationParams(level="info", data="Listing tools"))
+    else:
+        with pytest.raises(McpError) as caught:
+            await asyncio.wait_for(pending, timeout=3)
+        if mode == "closed":
+            assert "connection was closed" in _connection_error_message(caught.value, client.server_url, 0.2)
+        else:
+            assert isinstance(as_mcp_read_timeout(caught.value), TimeoutError)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("transport", [MCPTransport.sse, MCPTransport.stdio])
+async def test_transport_cancellation_cleans_up_a_pending_request(transport: MCPTransport) -> None:
+    ready: Final = asyncio.Event()
+
+    async def on_log(message: LoggingMessageNotificationParams) -> None:
+        if message.data == "Waiting":
+            ready.set()
+
+    client: Final = MCPClient(
+        server_url="https://example.com/sse", transport_type=transport, timeout=30, logging_callback=on_log
+    )
+    task: Final = asyncio.create_task(
+        client._execute_session_operation(
+            _diagnostic_transport(transport, "silent", "tools/list"), lambda session: session.list_tools()
+        )
+    )
+    try:
+        await asyncio.wait_for(ready.wait(), timeout=3)
+    finally:
+        task.cancel()
+        with pytest.raises(asyncio.CancelledError):
+            await asyncio.wait_for(task, timeout=3)
+
+
+class _InterruptedHTTPBody(httpx.AsyncByteStream):
+    async def __aiter__(self) -> AsyncIterator[bytes]:
+        yield b'{"jsonrpc":'
+        raise httpx.RemoteProtocolError("secret-incomplete-response")
+
+
+@pytest.mark.asyncio
+async def test_interrupted_http_response_preserves_the_transport_failure() -> None:
+    def respond(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, headers={"Content-Type": "application/json"}, stream=_InterruptedHTTPBody())
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        client: Final = MCPClient(server_url="https://example.com/mcp", timeout=30)
+        with pytest.raises(httpx.RemoteProtocolError, match="secret-incomplete-response"):
+            await asyncio.wait_for(
+                client._execute_session_operation(
+                    streamable_http_client(client.server_url, http_client=http_client),
+                    lambda session: session.list_tools(),
+                ),
+                timeout=3,
+            )
+
+
+@pytest.mark.asyncio
+async def test_empty_http_event_stream_uses_the_existing_request_deadline() -> None:
+    def respond(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, headers={"Content-Type": "text/event-stream"}, content=b"")
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        client: Final = MCPClient(server_url="https://example.com/mcp", timeout=0.2)
+        with pytest.raises(McpError) as caught:
+            await asyncio.wait_for(
+                client._execute_session_operation(
+                    streamable_http_client(client.server_url, http_client=http_client),
+                    lambda session: session.list_tools(),
+                ),
+                timeout=3,
+            )
+    assert isinstance(as_mcp_read_timeout(caught.value), TimeoutError)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("method", ("prompts/list", "resources/list", "resources/templates/list"))
+@pytest.mark.parametrize(
+    "outcome",
+    (
+        "absent",
+        "other_capability",
+        "supported",
+        "method_not_found",
+        "internal_error",
+        "unauthorized",
+        "timeout",
+        "initialize_not_found",
+    ),
+)
+async def test_optional_discovery_capabilities_and_errors(
+    method: str, outcome: str, caplog: pytest.LogCaptureFixture
+) -> None:
+    import logging
+    from unittest.mock import Mock
+
+    from mcp.types import JSONRPCRequest
+
+    capability: Final = "prompts" if method == "prompts/list" else "resources"
+    field: Final = {
+        "prompts/list": "prompts",
+        "resources/list": "resources",
+        "resources/templates/list": "resourceTemplates",
+    }[method]
+    advertised: Final = "resources" if capability == "prompts" else "prompts"
+    entry: Final = {
+        "prompts/list": {"name": "example"},
+        "resources/list": {"name": "example", "uri": "test://example"},
+        "resources/templates/list": {"name": "example", "uriTemplate": "test://{name}"},
+    }[method]
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "DELETE":
+            return httpx.Response(200)
+        payload: Final = JSONRPCMessage.model_validate_json(request.content).root
+        if not isinstance(payload, JSONRPCRequest):
+            return httpx.Response(202)
+        if outcome == "initialize_not_found":
+            return httpx.Response(
+                200,
+                json={
+                    "jsonrpc": "2.0",
+                    "id": payload.id,
+                    "error": {"code": -32601, "message": "Initialization rejected"},
+                },
+            )
+        if payload.method == "initialize":
+            return httpx.Response(
+                200,
+                json={
+                    "jsonrpc": "2.0",
+                    "id": payload.id,
+                    "result": {
+                        "protocolVersion": LATEST_PROTOCOL_VERSION,
+                        "capabilities": {}
+                        if outcome == "absent"
+                        else {advertised if outcome == "other_capability" else capability: {}},
+                        "serverInfo": {"name": "discovery", "version": "1"},
+                    },
+                },
+            )
+        if outcome == "timeout":
+            raise httpx.ReadTimeout("Optional list timed out", request=request)
+        if outcome == "unauthorized":
+            return httpx.Response(401)
+        if outcome in ("method_not_found", "internal_error", "absent", "other_capability"):
+            return httpx.Response(
+                200,
+                json={
+                    "jsonrpc": "2.0",
+                    "id": payload.id,
+                    "error": {
+                        "code": -32603 if outcome == "internal_error" else -32601,
+                        "message": "Optional list rejected",
+                    },
+                },
+            )
+        return httpx.Response(200, json={"jsonrpc": "2.0", "id": payload.id, "result": {field: [entry]}})
+
+    responder: Final = Mock(side_effect=respond)
+    caplog.set_level(logging.DEBUG, logger="LiteLLM")
+    with respx.mock(base_url="https://example.com") as router:
+        router.route().mock(side_effect=responder)
+        client: Final = MCPClient(server_url="https://example.com/mcp")
+        operation: Final = {
+            "prompts/list": client.list_prompts,
+            "resources/list": client.list_resources,
+            "resources/templates/list": client.list_resource_templates,
+        }[method]
+        result: Final = await operation()
+
+    requests: Final = tuple(
+        JSONRPCMessage.model_validate_json(call.args[0].content).root
+        for call in responder.call_args_list
+        if call.args[0].method == "POST"
+    )
+    assert sum(isinstance(request, JSONRPCRequest) and request.method == method for request in requests) == (
+        0 if outcome in ("absent", "other_capability", "initialize_not_found") else 1
+    )
+    assert [item.name for item in result] == (["example"] if outcome == "supported" else [])
+    failures: Final = tuple(
+        record for record in caplog.records if record.name == "LiteLLM" and record.levelno >= logging.WARNING
+    )
+    if outcome in ("internal_error", "unauthorized", "timeout", "initialize_not_found"):
+        assert any(record.levelno == logging.ERROR and "failed" in record.message for record in failures)
+    else:
+        assert failures == ()
+    if outcome == "method_not_found":
+        assert any(
+            record.levelno == logging.DEBUG and "Optional list rejected" in record.message for record in caplog.records
+        )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("supports_first", (True, False))
+async def test_optional_discovery_uses_each_sessions_capabilities(supports_first: bool) -> None:
+    from unittest.mock import Mock
+    from mcp.types import JSONRPCRequest
+
+    capabilities: Final = iter(({"resources": {}}, {}) if supports_first else ({}, {"resources": {}}))
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "DELETE":
+            return httpx.Response(200)
+        payload: Final = JSONRPCMessage.model_validate_json(request.content).root
+        if not isinstance(payload, JSONRPCRequest):
+            return httpx.Response(202)
+        result: Final = (
+            {
+                "protocolVersion": LATEST_PROTOCOL_VERSION,
+                "capabilities": next(capabilities),
+                "serverInfo": {"name": "changing", "version": "1"},
+            }
+            if payload.method == "initialize"
+            else {"resources": [{"name": "example", "uri": "test://example"}]}
+        )
+        return httpx.Response(200, json={"jsonrpc": "2.0", "id": payload.id, "result": result})
+
+    responder: Final = Mock(side_effect=respond)
+    with respx.mock(base_url="https://example.com") as router:
+        router.route().mock(side_effect=responder)
+        client: Final = MCPClient(server_url="https://example.com/mcp")
+        first: Final = await client.list_resources()
+        second: Final = await client.list_resources()
+
+    assert [item.name for item in first] == (["example"] if supports_first else [])
+    assert [item.name for item in second] == ([] if supports_first else ["example"])
+    requests: Final = tuple(
+        JSONRPCMessage.model_validate_json(call.args[0].content).root
+        for call in responder.call_args_list
+        if call.args[0].method == "POST"
+    )
+    assert sum(isinstance(request, JSONRPCRequest) and request.method == "resources/list" for request in requests) == 1
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("method", ("prompts/list", "resources/list", "resources/templates/list"))
+async def test_optional_discovery_preserves_cancellation(method: str) -> None:
+    from mcp.types import JSONRPCRequest
+
+    ready: Final = asyncio.Event()
+    pending: Final = asyncio.Event()
+
+    async def respond(request: httpx.Request) -> httpx.Response:
+        if request.method == "DELETE":
+            return httpx.Response(200)
+        payload: Final = JSONRPCMessage.model_validate_json(request.content).root
+        if not isinstance(payload, JSONRPCRequest):
+            return httpx.Response(202)
+        if payload.method == "initialize":
+            return httpx.Response(
+                200,
+                json={
+                    "jsonrpc": "2.0",
+                    "id": payload.id,
+                    "result": {
+                        "protocolVersion": LATEST_PROTOCOL_VERSION,
+                        "capabilities": {"resources": {}, "prompts": {}},
+                        "serverInfo": {"name": "pending", "version": "1"},
+                    },
+                },
+            )
+        ready.set()
+        await pending.wait()
+        return httpx.Response(202)
+
+    with respx.mock(base_url="https://example.com") as router:
+        router.route().mock(side_effect=respond)
+        client: Final = MCPClient(server_url="https://example.com/mcp")
+        operation: Final = {
+            "prompts/list": client.list_prompts,
+            "resources/list": client.list_resources,
+            "resources/templates/list": client.list_resource_templates,
+        }[method]
+        task: Final = asyncio.create_task(operation())
+        try:
+            await asyncio.wait_for(ready.wait(), timeout=3)
+        finally:
+            task.cancel()
+            with pytest.raises(asyncio.CancelledError):
+                await asyncio.wait_for(task, timeout=3)
diff --git a/tests/test_litellm/integrations/newrelic/test_newrelic_metrics.py b/tests/test_litellm/integrations/newrelic/test_newrelic_metrics.py
index 9c75e0b0a47..a9074e89806 100644
--- a/tests/test_litellm/integrations/newrelic/test_newrelic_metrics.py
+++ b/tests/test_litellm/integrations/newrelic/test_newrelic_metrics.py
@@ -24,6 +24,8 @@ from litellm.types.integrations.newrelic import (
     NEWRELIC_METRIC_PROMPT_TOKENS,
     NEWRELIC_METRIC_REQUEST_DURATION_MS,
     NEWRELIC_METRIC_REQUESTS,
+    NEWRELIC_METRIC_TEAM_MAX_BUDGET,
+    NEWRELIC_METRIC_TEAM_REMAINING_BUDGET,
     NEWRELIC_METRIC_TOTAL_TOKENS,
     NewRelicMetricRecord,
 )
@@ -40,6 +42,8 @@ def _record(
     completion_tokens=20,
     total_tokens=30,
     duration_ms=100.0,
+    team_max_budget=None,
+    team_spend=None,
 ) -> NewRelicMetricRecord:
     return NewRelicMetricRecord(
         team_id=team_id,
@@ -53,12 +57,28 @@ def _record(
         completion_tokens=completion_tokens,
         total_tokens=total_tokens,
         duration_ms=duration_ms,
+        team_max_budget=team_max_budget,
+        team_spend=team_spend,
     )
 
 
-def _standard_logging_object(team_id="team-a", response_cost=0.25) -> dict:
+def _standard_logging_object(
+    team_id="team-a", response_cost=0.25, team_max_budget: float | None = None, team_spend: float | None = None
+) -> dict:
+    budget_metadata = {
+        key: value
+        for key, value in (
+            ("user_api_key_team_max_budget", team_max_budget),
+            ("user_api_key_team_spend", team_spend),
+        )
+        if value is not None
+    }
     return {
-        "metadata": {"user_api_key_team_id": team_id, "user_api_key_team_alias": f"{team_id}-alias"},
+        "metadata": {
+            "user_api_key_team_id": team_id,
+            "user_api_key_team_alias": f"{team_id}-alias",
+            **budget_metadata,
+        },
         "model_group": "gpt-4o-group",
         "model": "gpt-4o",
         "custom_llm_provider": "openai",
@@ -204,6 +224,74 @@ class TestBuildMetricPayload:
         assert "model_group" not in attributes
 
 
+class TestTeamBudgetGauges:
+    def test_latest_record_per_team_drives_one_gauge_pair(self):
+        records = (
+            _record(team_id="team-a", model="gpt-4o", response_cost=0.5, team_max_budget=100.0, team_spend=10.0),
+            _record(team_id="team-a", model="claude-4", response_cost=2.0, team_max_budget=100.0, team_spend=10.5),
+            _record(team_id="team-b", response_cost=1.0, team_max_budget=None, team_spend=3.0),
+            _record(team_id="", team_alias="", response_cost=1.0, team_max_budget=50.0, team_spend=1.0),
+        )
+        payload = build_metric_payload(records, window_start=1_000.0, now=1_005.0)
+
+        max_budget_gauges = _metrics_by_name(payload, NEWRELIC_METRIC_TEAM_MAX_BUDGET)
+        remaining_gauges = _metrics_by_name(payload, NEWRELIC_METRIC_TEAM_REMAINING_BUDGET)
+        assert [(m["type"], m["value"], m["attributes"]) for m in max_budget_gauges] == [
+            ("gauge", 100.0, {"team_id": "team-a", "team_alias": "team-a-alias"})
+        ]
+        assert [(m["type"], m["attributes"]) for m in remaining_gauges] == [
+            ("gauge", {"team_id": "team-a", "team_alias": "team-a-alias"})
+        ]
+        assert remaining_gauges[0]["value"] == pytest.approx(100.0 - 10.5 - 2.0)
+        assert len(_metrics_by_name(payload, NEWRELIC_METRIC_COST_USD)) == 4
+
+    def test_missing_team_spend_counts_only_this_request(self):
+        payload = build_metric_payload(
+            (_record(response_cost=0.25, team_max_budget=10.0, team_spend=None),), window_start=1_000.0, now=1_005.0
+        )
+
+        assert _metrics_by_name(payload, NEWRELIC_METRIC_TEAM_REMAINING_BUDGET)[0]["value"] == pytest.approx(9.75)
+
+    @pytest.mark.asyncio
+    async def test_budget_gauges_reach_the_metric_api_from_standard_logging_metadata(self):
+        logger = _make_logger()
+        logger.async_client.post = AsyncMock(return_value=_response(202))
+        slo = _standard_logging_object(response_cost=0.25, team_max_budget=20.0, team_spend=4.5)
+
+        await logger.async_log_success_event(
+            kwargs={"standard_logging_object": slo}, response_obj={}, start_time=None, end_time=None
+        )
+        await logger.flush_queue()
+
+        body = json.loads(gzip.decompress(logger.async_client.post.await_args.kwargs["data"]).decode("utf-8"))
+        by_name = {m["name"]: m for m in body[0]["metrics"]}
+        assert by_name[NEWRELIC_METRIC_TEAM_MAX_BUDGET] == {
+            "name": NEWRELIC_METRIC_TEAM_MAX_BUDGET,
+            "type": "gauge",
+            "value": 20.0,
+            "attributes": {"team_id": "team-a", "team_alias": "team-a-alias"},
+        }
+        assert by_name[NEWRELIC_METRIC_TEAM_REMAINING_BUDGET]["type"] == "gauge"
+        assert by_name[NEWRELIC_METRIC_TEAM_REMAINING_BUDGET]["value"] == pytest.approx(15.25)
+        assert by_name[NEWRELIC_METRIC_COST_USD]["value"] == 0.25
+
+    @pytest.mark.asyncio
+    async def test_no_budget_metadata_sends_no_gauges(self):
+        logger = _make_logger()
+        logger.async_client.post = AsyncMock(return_value=_response(202))
+
+        await logger.async_log_success_event(
+            kwargs={"standard_logging_object": _standard_logging_object()},
+            response_obj={},
+            start_time=None,
+            end_time=None,
+        )
+        await logger.flush_queue()
+
+        body = json.loads(gzip.decompress(logger.async_client.post.await_args.kwargs["data"]).decode("utf-8"))
+        assert {m["type"] for m in body[0]["metrics"]} == {"count", "summary"}
+
+
 class TestQueueAndFlush:
     @pytest.mark.asyncio
     async def test_log_event_queues_record_from_standard_logging_object(self):
diff --git a/tests/test_litellm/integrations/pointfive/test_logger.py b/tests/test_litellm/integrations/pointfive/test_logger.py
new file mode 100644
index 00000000000..52570751c74
--- /dev/null
+++ b/tests/test_litellm/integrations/pointfive/test_logger.py
@@ -0,0 +1,759 @@
+import asyncio
+import gzip
+import json
+import logging
+from collections.abc import Callable
+
+import pytest
+
+from litellm.integrations.pointfive.logger import PointFiveLogger
+from litellm.integrations.pointfive.upload_client import PointFiveUploadError
+from litellm.types.integrations.pointfive import DEFAULT_API_URL, PointFiveInitParams, PointFiveUploadFailure
+
+OBJECT_KEY = "some/object.ndjson.gz"
+
+
+class FakeUploadClient:
+    """Records the objects a flush produced, so tests can read what would have shipped."""
+
+    def __init__(
+        self,
+        outcomes: list[str | PointFiveUploadFailure] | None = None,
+        ping_failure: PointFiveUploadFailure | None = None,
+    ) -> None:
+        self.outcomes = outcomes or [OBJECT_KEY]
+        self.bodies: list[bytes] = []
+        self.on_upload: Callable[[], None] | None = None
+        self.ping_failure = ping_failure
+        self.pings = 0
+
+    async def ping(self) -> PointFiveUploadFailure | None:
+        self.pings += 1
+        return self.ping_failure
+
+    async def upload(self, body: bytes) -> str | PointFiveUploadFailure:
+        if self.on_upload is not None:
+            self.on_upload()
+        self.bodies.append(body)
+        return self.outcomes.pop(0) if len(self.outcomes) > 1 else self.outcomes[0]
+
+    def records(self) -> list[dict]:
+        return [json.loads(line) for body in self.bodies for line in gzip.decompress(body).decode().splitlines()]
+
+
+def _logger(upload_client: FakeUploadClient, **params) -> PointFiveLogger:
+    return PointFiveLogger(params=PointFiveInitParams(**params), upload_client=upload_client)
+
+
+def _event(request_id: str, size: int = 0) -> dict:
+    return {"standard_logging_object": {"id": request_id, "model": "gpt-4o", "blob": "x" * size}}
+
+
+@pytest.mark.asyncio
+async def test_a_flush_ships_one_object_holding_every_buffered_record():
+    """One object per flush is the whole point: s3_v2 sends one per request."""
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=3)
+
+    for request_id in ("a", "b", "c"):
+        await logger.async_log_success_event(_event(request_id), None, None, None)
+
+    await _settle(logger)
+    assert len(upload_client.bodies) == 1
+    assert [record["id"] for record in upload_client.records()] == ["a", "b", "c"]
+
+
+@pytest.mark.asyncio
+async def test_records_are_held_until_the_batch_is_full():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=3)
+
+    await logger.async_log_success_event(_event("a"), None, None, None)
+
+    assert upload_client.bodies == []
+    assert len(logger.log_queue) == 1
+
+
+@pytest.mark.asyncio
+async def test_failed_requests_are_logged_too():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1)
+
+    await logger.async_log_failure_event(_event("failed"), None, None, None)
+
+    await _settle(logger)
+    assert [record["id"] for record in upload_client.records()] == ["failed"]
+
+
+@pytest.mark.asyncio
+async def test_an_event_without_a_standard_payload_is_skipped():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1)
+
+    await logger.async_log_success_event({"kwargs": "but no payload"}, None, None, None)
+
+    assert upload_client.bodies == []
+    assert logger.log_queue == []
+
+
+@pytest.mark.asyncio
+async def test_a_batch_over_the_byte_cap_ships_as_several_objects():
+    """Record count cannot bound an object: an unredacted payload dwarfs a redacted one."""
+    cap = 600
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=4, max_batch_bytes=cap)
+
+    for request_id in ("a", "b", "c", "d"):
+        await logger.async_log_success_event(_event(request_id, size=200), None, None, None)
+
+    await _settle(logger)
+    assert len(upload_client.bodies) > 1
+    assert [record["id"] for record in upload_client.records()] == ["a", "b", "c", "d"]
+    assert all(len(gzip.decompress(body)) <= cap for body in upload_client.bodies)
+
+
+@pytest.mark.asyncio
+async def test_a_retryable_failure_keeps_the_batch_for_the_next_flush():
+    upload_client = FakeUploadClient([PointFiveUploadFailure("upload target is down", retryable=True)])
+    logger = _logger(upload_client, batch_size=2)
+
+    for request_id in ("a", "b"):
+        await logger.async_log_success_event(_event(request_id), None, None, None)
+
+    assert [record["id"] for record in logger.log_queue] == ["a", "b"]
+
+
+@pytest.mark.asyncio
+async def test_a_retryable_failure_surfaces_so_the_base_logger_can_preserve_it():
+    upload_client = FakeUploadClient([PointFiveUploadFailure("upload target is down", retryable=True)])
+    logger = _logger(upload_client, batch_size=99)
+    logger.log_queue.append(_event("a")["standard_logging_object"])
+
+    with pytest.raises(PointFiveUploadError, match="upload target is down"):
+        await logger.async_send_batch()
+
+
+@pytest.mark.asyncio
+async def test_a_rejected_batch_is_dropped_rather_than_blocking_the_queue():
+    """Retrying a rejection forever would stall every record queued behind it."""
+    upload_client = FakeUploadClient([PointFiveUploadFailure("object too large", retryable=False)])
+    logger = _logger(upload_client, batch_size=2)
+
+    for request_id in ("a", "b"):
+        await logger.async_log_success_event(_event(request_id), None, None, None)
+
+    await _settle(logger)
+    assert logger.log_queue == []
+
+
+@pytest.mark.asyncio
+async def test_records_already_queued_ship_with_the_event_that_triggers_the_flush():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1)
+    logger.log_queue.append(_event("mid-flight")["standard_logging_object"])
+
+    await logger.async_log_success_event(_event("a"), None, None, None)
+
+    await _settle(logger)
+    assert [record["id"] for record in upload_client.records()] == ["mid-flight", "a"]
+    assert logger.log_queue == []
+
+
+@pytest.mark.asyncio
+async def test_a_record_that_arrives_mid_flush_is_kept_for_the_next_one():
+    """The queue is drained by count, so a record appended mid-upload must survive."""
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1)
+    upload_client.on_upload = lambda: logger.log_queue.append(_event("late")["standard_logging_object"])
+
+    await logger.async_log_success_event(_event("first"), None, None, None)
+
+    await _settle(logger)
+    assert [record["id"] for record in upload_client.records()] == ["first"]
+    assert [record["id"] for record in logger.log_queue] == ["late"]
+
+
+def test_defaults_favour_fewer_larger_uploads_over_freshness():
+    upload_client = FakeUploadClient()
+
+    logger = _logger(upload_client)
+
+    assert logger.batch_size == 1_000
+    assert logger.flush_interval == 300
+    assert logger.max_batch_bytes == 8 * 1024 * 1024
+
+
+def test_the_default_api_url_is_the_pointfive_ingress(monkeypatch):
+    """api.pointfive.co is the host the ingress serves; .com does not resolve to it."""
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_env")
+
+    logger = PointFiveLogger()
+
+    assert logger.upload_client.api_url == "https://api.pointfive.co/api/v1/ingestion"
+
+
+def test_the_api_key_can_come_from_the_environment(monkeypatch):
+    """The proxy ui configures a callback by writing environment variables."""
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_from_env")
+
+    logger = PointFiveLogger()
+
+    assert logger.upload_client.api_key == "p5tu_from_env"
+
+
+def test_the_api_url_can_come_from_the_environment(monkeypatch):
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_env")
+    monkeypatch.setenv("POINTFIVE_API_URL", "https://api.staging.pointfive.co/api/v1/ingestion")
+
+    logger = PointFiveLogger()
+
+    assert logger.upload_client.api_url == "https://api.staging.pointfive.co/api/v1/ingestion"
+
+
+def test_config_yaml_wins_over_the_environment(monkeypatch):
+    """A value set in config.yaml is explicit, so it outranks whatever the ui left behind."""
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_from_env")
+    monkeypatch.setenv("POINTFIVE_API_URL", "https://from-env.example/api/v1/ingestion")
+
+    logger = PointFiveLogger(
+        params=PointFiveInitParams(api_key="p5tu_from_config", api_url="https://from-config.example/api/v1/ingestion")
+    )
+
+    assert logger.upload_client.api_key == "p5tu_from_config"
+    assert logger.upload_client.api_url == "https://from-config.example/api/v1/ingestion"
+
+
+def test_a_missing_api_key_fails_at_startup_not_at_the_first_flush(monkeypatch):
+    monkeypatch.delenv("POINTFIVE_API_KEY", raising=False)
+
+    with pytest.raises(ValueError, match="api key"):
+        PointFiveLogger(params=PointFiveInitParams())
+
+
+def test_an_api_key_can_be_an_environment_reference(monkeypatch):
+    """config.yaml spells secrets as `os.environ/NAME`, so the plugin must resolve one."""
+    monkeypatch.setenv("POINTFIVE_TEST_KEY", "p5tu_from_env")
+
+    logger = PointFiveLogger(params=PointFiveInitParams(api_key="os.environ/POINTFIVE_TEST_KEY"))
+
+    assert logger.upload_client.api_key == "p5tu_from_env"
+
+
+def test_params_are_read_from_litellm_settings(monkeypatch):
+    import litellm
+
+    monkeypatch.setattr(litellm, "pointfive_params", {"api_key": "p5tu_configured", "batch_size": 7})
+
+    logger = PointFiveLogger()
+
+    assert logger.upload_client.api_key == "p5tu_configured"
+    assert logger.batch_size == 7
+
+
+def test_an_out_of_range_setting_is_rejected():
+    with pytest.raises(ValueError, match="batch_size"):
+        PointFiveInitParams(api_key="p5tu_k", batch_size=0)
+
+
+@pytest.mark.asyncio
+async def test_an_idle_flush_reports_liveness_instead_of_uploading():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=99)
+
+    await logger.flush_queue()
+
+    assert upload_client.pings == 1
+    assert upload_client.bodies == []
+
+
+@pytest.mark.asyncio
+async def test_a_flush_with_records_uploads_and_does_not_ping():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1)
+
+    await logger.async_log_success_event(_event("a"), None, None, None)
+
+    await _settle(logger)
+    assert upload_client.pings == 0
+    assert len(upload_client.bodies) == 1
+
+
+@pytest.mark.asyncio
+async def test_a_failed_ping_does_not_raise():
+    """Liveness is bookkeeping; a proxy must not see errors from it."""
+    upload_client = FakeUploadClient(ping_failure=PointFiveUploadFailure("api down", retryable=True))
+    logger = _logger(upload_client, batch_size=99)
+
+    await logger.flush_queue()
+
+    assert upload_client.pings == 1
+
+
+@pytest.mark.asyncio
+async def test_health_check_is_healthy_when_the_api_accepts_the_key():
+    upload_client = FakeUploadClient()
+
+    assert await _logger(upload_client).async_health_check() == {"status": "healthy", "error_message": None}
+    assert upload_client.pings == 1
+
+
+@pytest.mark.asyncio
+async def test_health_check_reports_why_the_api_refused():
+    """The ui test button shows this message, so a rejected key has to say so rather than pass."""
+    upload_client = FakeUploadClient(ping_failure=PointFiveUploadFailure("key was revoked", retryable=False))
+
+    outcome = await _logger(upload_client).async_health_check()
+
+    assert outcome == {"status": "unhealthy", "error_message": "key was revoked"}
+
+
+def test_the_client_follows_a_key_and_url_changed_after_startup(monkeypatch):
+    """
+    The proxy ui writes new values into a running proxy's environment.
+
+    Reading them once at construction would leave the logger talking to the old endpoint
+    until someone restarted the proxy.
+    """
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_first")
+    monkeypatch.setenv("POINTFIVE_API_URL", "https://first.example.invalid/api/v1/ingestion")
+    logger = PointFiveLogger(params=PointFiveInitParams())
+
+    assert logger.upload_client.api_key == "p5tu_first"
+    assert logger.upload_client.api_url == "https://first.example.invalid/api/v1/ingestion"
+
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_second")
+    monkeypatch.setenv("POINTFIVE_API_URL", "https://second.example.invalid/api/v1/ingestion")
+
+    assert logger.upload_client.api_key == "p5tu_second"
+    assert logger.upload_client.api_url == "https://second.example.invalid/api/v1/ingestion"
+
+
+def test_a_configured_key_still_wins_over_the_environment(monkeypatch):
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_from_env")
+    logger = PointFiveLogger(params=PointFiveInitParams(api_key="p5tu_from_config"))
+
+    assert logger.upload_client.api_key == "p5tu_from_config"
+
+
+@pytest.mark.asyncio
+async def test_health_check_says_so_when_the_key_was_removed(monkeypatch):
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_present")
+    logger = PointFiveLogger(params=PointFiveInitParams())
+    monkeypatch.delenv("POINTFIVE_API_KEY")
+
+    outcome = await logger.async_health_check()
+
+    assert outcome["status"] == "unhealthy"
+    assert "requires an api key" in (outcome["error_message"] or "")
+
+
+def _pending_flush_tasks() -> tuple[asyncio.Task, ...]:
+    return tuple(task for task in asyncio.all_tasks() if "periodic_flush" in str(task.get_coro()))
+
+
+@pytest.mark.asyncio
+async def test_a_one_shot_logger_leaves_no_flush_task_behind():
+    """
+    A health check builds a logger for a single answer and drops it.
+
+    Without this, every check would leave a flusher running that keeps pinging for the
+    lifetime of the proxy.
+    """
+    before = _pending_flush_tasks()
+
+    logger = PointFiveLogger(params=PointFiveInitParams(), upload_client=FakeUploadClient(), start_periodic_flush=False)
+
+    assert logger._periodic_flush_task is None
+    assert _pending_flush_tasks() == before
+
+
+@pytest.mark.asyncio
+async def test_the_logger_flushes_periodically_by_default():
+    logger = PointFiveLogger(params=PointFiveInitParams(), upload_client=FakeUploadClient())
+
+    assert logger._periodic_flush_task is not None
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_params_already_built_are_used_as_they_are(monkeypatch):
+    """config.yaml is validated once into a params object; a second validation would be wasted."""
+    import litellm
+
+    monkeypatch.setattr(litellm, "pointfive_params", PointFiveInitParams(max_batch_bytes=4096))
+
+    logger = PointFiveLogger(upload_client=FakeUploadClient())
+
+    assert logger.max_batch_bytes == 4096
+
+
+@pytest.mark.asyncio
+async def test_a_dead_flush_task_is_restarted_by_the_next_event():
+    """A cancelled or crashed flusher would otherwise leave the queue growing forever."""
+    logger = _logger(FakeUploadClient())
+    logger._periodic_flush_task.cancel()
+    await asyncio.sleep(0)  # let the cancellation land, so the task reports itself done
+
+    await logger.async_log_success_event(_event("after-cancel"), None, None, None)
+
+    assert logger._periodic_flush_task is not None
+    assert not logger._periodic_flush_task.done()
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_a_failure_while_queueing_never_breaks_the_request():
+    """Logging sits on the request path, so a fault here must not surface to the caller."""
+
+    class ExplodingQueue(list):
+        def append(self, _item):
+            raise RuntimeError("queue is broken")
+
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client)
+    logger.log_queue = ExplodingQueue()
+
+    await logger.async_log_success_event(_event("boom"), None, None, None)
+
+    logger.log_queue = []
+    await logger.async_log_success_event(_event("after-the-fault"), None, None, None)
+    assert [record["id"] for record in logger.log_queue] == ["after-the-fault"]
+
+
+@pytest.mark.asyncio
+async def test_a_flush_with_nothing_queued_uploads_nothing():
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client)
+
+    await logger.async_send_batch()
+
+    assert upload_client.bodies == []
+
+
+@pytest.mark.asyncio
+async def test_the_idle_ping_is_skipped_when_the_key_was_removed(monkeypatch, caplog):
+    """A key pulled mid-flight must not turn the periodic flush into an exception."""
+    monkeypatch.setenv("POINTFIVE_API_KEY", "p5tu_present")
+    logger = PointFiveLogger(params=PointFiveInitParams())
+    monkeypatch.delenv("POINTFIVE_API_KEY")
+
+    with caplog.at_level(logging.WARNING):
+        await logger.flush_queue()
+
+    assert "liveness ping skipped" in caplog.text
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_a_full_batch_stands_down_while_a_flush_is_already_running():
+    """
+    Under load every event landing mid-upload also crosses the batch threshold.
+
+    Letting each one flush turns a single burst into a stream of tiny objects, which is
+    what batching exists to avoid, so a full batch defers to the flush already running.
+    """
+    upload_client = FakeUploadClient()
+    # No periodic task: this test drives the flushes itself, and the loop's opening cycle
+    # would otherwise ship the queue it seeds below.
+    logger = PointFiveLogger(
+        params=PointFiveInitParams(batch_size=2),
+        upload_client=upload_client,
+        start_periodic_flush=False,
+    )
+    release = asyncio.Event()
+    finish_upload = upload_client.upload
+
+    async def held_upload(body: bytes):
+        await release.wait()
+        return await finish_upload(body)
+
+    upload_client.upload = held_upload
+    logger.log_queue.extend(_event(f"first-{index}")["standard_logging_object"] for index in range(2))
+
+    flushing = asyncio.create_task(logger.flush_queue())
+    await asyncio.sleep(0)
+
+    # Bounded: without the guard these block on the flush lock the held upload owns.
+    for index in range(6):
+        await asyncio.wait_for(logger.async_log_success_event(_event(f"mid-{index}"), None, None, None), timeout=2)
+
+    assert upload_client.bodies == []
+
+    release.set()
+    await flushing
+
+    assert len(upload_client.bodies) == 1
+    assert [record["id"] for record in upload_client.records()] == ["first-0", "first-1"]
+    assert [record["id"] for record in logger.log_queue] == [f"mid-{index}" for index in range(6)]
+
+
+async def _settle(logger) -> None:
+    """
+    Wait out the flush a full batch schedules, the way the proxy's loop would.
+
+    The upload runs off the request path now, and either the batch task or the periodic
+    loop can be the one carrying it, so this waits for whichever is in flight to finish.
+    """
+    for _ in range(200):
+        await asyncio.sleep(0.001)
+        task = logger._batch_flush_task
+        if task is not None and not task.done():
+            await task
+        if not logger._flushing:
+            return
+    raise AssertionError("the flush never finished")
+
+
+async def _until(done: Callable[[], bool], ticks: int = 400) -> None:
+    """Wait for a condition the flush path reaches only after gzip finishes on a worker thread."""
+    for _ in range(ticks):
+        if done():
+            return
+        await asyncio.sleep(0.005)
+    raise AssertionError("condition never became true")
+
+
+@pytest.mark.asyncio
+async def test_a_new_logger_announces_itself_without_waiting_for_the_interval():
+    """
+    Configuring the callback must make the integration connect, with no traffic and no test click.
+
+    The inherited loop sleeps a whole interval before its first flush, which left a freshly
+    configured proxy silent for five minutes and the integration looking unconfigured.
+    """
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client)
+
+    await asyncio.sleep(0)  # let the flush task reach its first cycle
+
+    assert upload_client.pings == 1
+    assert upload_client.bodies == []
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_the_first_cycle_ships_records_rather_than_announcing():
+    """Announcing is only for an empty queue: records already waiting must go out as an upload."""
+    upload_client = FakeUploadClient()
+    logger = PointFiveLogger(
+        params=PointFiveInitParams(batch_size=100),
+        upload_client=upload_client,
+        start_periodic_flush=False,
+    )
+    logger.log_queue.append(_event("queued-before-start")["standard_logging_object"])
+
+    logger._periodic_flush_task = logger._start_periodic_flush_task()
+    await _until(lambda: bool(upload_client.bodies))
+
+    assert upload_client.pings == 0
+    assert [record["id"] for record in upload_client.records()] == ["queued-before-start"]
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_a_failed_request_ships_redacted_when_message_logging_is_off():
+    """
+    Failure events skip the framework's redaction, so the callback has to redact what it buffers.
+
+    Without this the prompt of every failed request reaches PointFive in full, even though
+    the integration was configured not to send message content.
+    """
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1, turn_off_message_logging=True)
+    event = _event("failed-request")
+    event["standard_logging_object"]["messages"] = [{"role": "user", "content": "my secret prompt"}]
+    event["standard_logging_object"]["response"] = "the secret answer"
+
+    await logger.async_log_failure_event(event, None, None, None)
+    await _settle(logger)
+
+    shipped = upload_client.records()[0]
+    assert "my secret prompt" not in json.dumps(shipped)
+    assert "the secret answer" not in json.dumps(shipped)
+    assert event["standard_logging_object"]["messages"][0]["content"] == "my secret prompt"
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_a_dead_loop_does_not_strand_the_flusher():
+    """A task whose loop was closed never runs and never reports done, so it must be replaced."""
+    logger = PointFiveLogger(params=PointFiveInitParams(), upload_client=FakeUploadClient(), start_periodic_flush=False)
+    stranded_loop = asyncio.new_event_loop()
+    forever = asyncio.sleep(3600)
+    logger._periodic_flush_task = stranded_loop.create_task(forever)
+    stranded_loop.close()
+    forever.close()
+
+    await logger.async_log_success_event(_event("after-loop-close"), None, None, None)
+
+    assert logger._periodic_flush_task is not None
+    assert logger._periodic_flush_task.get_loop() is asyncio.get_running_loop()
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_a_retry_does_not_resend_objects_that_already_landed():
+    """
+    A failure part way through a multi-object flush used to hand the whole batch back.
+
+    Every record already shipped, and every record already refused for good, went out
+    again on the next flush, so PointFive received duplicates of both.
+    """
+    upload_client = FakeUploadClient(outcomes=[OBJECT_KEY, PointFiveUploadFailure("service busy", retryable=True)])
+    logger = PointFiveLogger(
+        params=PointFiveInitParams(max_batch_bytes=1),  # one record per object
+        upload_client=upload_client,
+        start_periodic_flush=False,
+    )
+    logger.log_queue.extend(_event(request_id)["standard_logging_object"] for request_id in ("first", "second"))
+
+    with pytest.raises(PointFiveUploadError):
+        await logger.async_send_batch()
+
+    assert [record["id"] for record in logger.log_queue] == ["second"]
+
+
+@pytest.mark.asyncio
+async def test_the_queue_stops_growing_at_its_cap_without_waiting_for_a_failure():
+    """The base class trims only after a failed send, so a proxy that keeps flushing never trims."""
+    logger = _logger(FakeUploadClient(), batch_size=10_000)
+    logger.max_queue_size = 3
+
+    for request_id in ("a", "b", "c", "d", "e"):
+        await logger.async_log_success_event(_event(request_id), None, None, None)
+
+    assert [record["id"] for record in logger.log_queue] == ["c", "d", "e"]
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_a_failed_request_honours_the_global_redaction_setting(monkeypatch):
+    """
+    Redaction can be turned on globally or per request, not only on this callback.
+
+    The async failure path hands the payload over untouched, so a tenant could trigger a
+    provider failure and ship prompts that the operator had already asked to be redacted.
+    """
+    import litellm
+
+    monkeypatch.setattr(litellm, "turn_off_message_logging", True)
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1)
+    event = _event("globally-redacted")
+    event["standard_logging_object"]["messages"] = [{"role": "user", "content": "my secret prompt"}]
+
+    await logger.async_log_failure_event(event, None, None, None)
+
+    await _settle(logger)
+    assert "my secret prompt" not in json.dumps(upload_client.records()[0])
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_excluded_fields_are_dropped_from_a_failed_request(monkeypatch):
+    """standard_logging_payload_excluded_fields drops a field entirely; failures skipped it too."""
+    import litellm
+
+    monkeypatch.setattr(litellm, "standard_logging_payload_excluded_fields", ["messages"])
+    upload_client = FakeUploadClient()
+    logger = _logger(upload_client, batch_size=1, turn_off_message_logging=True)
+    event = _event("field-excluded")
+    event["standard_logging_object"]["messages"] = [{"role": "user", "content": "my secret prompt"}]
+
+    await logger.async_log_failure_event(event, None, None, None)
+    await _settle(logger)
+
+    shipped = upload_client.records()[0]
+    assert "messages" not in shipped
+    assert shipped["id"] == "field-excluded"
+    logger._periodic_flush_task.cancel()
+
+
+def _held_upload(upload_client: FakeUploadClient, release: asyncio.Event) -> None:
+    finish = upload_client.upload
+
+    async def held(body: bytes):
+        await release.wait()
+        return await finish(body)
+
+    upload_client.upload = held
+
+
+@pytest.mark.asyncio
+async def test_a_full_batch_does_not_hold_the_request():
+    """
+    The upload belongs off the request path.
+
+    Awaiting it inline meant a hung PointFive api held the caller's response open for as
+    long as the attempts and their backoff took.
+    """
+    upload_client = FakeUploadClient()
+    release = asyncio.Event()
+    _held_upload(upload_client, release)
+    logger = _logger(upload_client, batch_size=1)
+
+    await asyncio.wait_for(logger.async_log_success_event(_event("first"), None, None, None), timeout=2)
+
+    assert upload_client.bodies == []
+    release.set()
+    await _settle(logger)
+    assert [record["id"] for record in upload_client.records()] == ["first"]
+    logger._periodic_flush_task.cancel()
+
+
+@pytest.mark.asyncio
+async def test_records_arriving_during_a_flush_survive_the_queue_cap():
+    """
+    The flush drains by count, so trimming the front underneath it loses records.
+
+    Records that arrived while the upload was in flight would be deleted by that drain
+    without ever being sent.
+    """
+    upload_client = FakeUploadClient()
+    release = asyncio.Event()
+    _held_upload(upload_client, release)
+    logger = PointFiveLogger(
+        params=PointFiveInitParams(batch_size=2),
+        upload_client=upload_client,
+        start_periodic_flush=False,
+    )
+    logger.max_queue_size = 2
+    logger.log_queue.extend(_event(request_id)["standard_logging_object"] for request_id in ("a", "b"))
+
+    flushing = asyncio.create_task(logger.flush_queue())
+    await asyncio.sleep(0.01)
+    for request_id in ("c", "d", "e"):
+        await logger.async_log_success_event(_event(request_id), None, None, None)
+    release.set()
+    await flushing
+
+    assert [record["id"] for record in upload_client.records()] == ["a", "b"]
+    assert [record["id"] for record in logger.log_queue] == ["c", "d", "e"]
+    logger._periodic_flush_task.cancel()
+
+
+def test_an_unset_env_reference_is_never_used_as_the_key(monkeypatch):
+    """
+    A config that names a missing variable has no key, and must say so.
+
+    Falling back to the reference text sent the literal "os.environ/NAME" as the bearer
+    token, so the callback started and every upload was rejected for the wrong reason.
+    """
+    monkeypatch.delenv("POINTFIVE_API_KEY", raising=False)
+    monkeypatch.delenv("POINTFIVE_MISSING_KEY", raising=False)
+
+    with pytest.raises(ValueError, match="requires an api key"):
+        PointFiveLogger(
+            params=PointFiveInitParams(api_key="os.environ/POINTFIVE_MISSING_KEY"),
+            start_periodic_flush=False,
+        )
+
+
+def test_an_unset_url_reference_falls_back_to_the_public_endpoint(monkeypatch):
+    """An unresolved url reference must not become the destination the proxy uploads to."""
+    from litellm.integrations.pointfive.logger import _resolved_api_url
+
+    monkeypatch.delenv("POINTFIVE_API_URL", raising=False)
+    monkeypatch.delenv("POINTFIVE_MISSING_URL", raising=False)
+
+    assert _resolved_api_url(PointFiveInitParams(api_url="os.environ/POINTFIVE_MISSING_URL")) == DEFAULT_API_URL
diff --git a/tests/test_litellm/integrations/pointfive/test_payload.py b/tests/test_litellm/integrations/pointfive/test_payload.py
new file mode 100644
index 00000000000..d310941e396
--- /dev/null
+++ b/tests/test_litellm/integrations/pointfive/test_payload.py
@@ -0,0 +1,80 @@
+import gzip
+import json
+
+import pytest
+
+from litellm.integrations.pointfive.payload import chunk_lines, encode_lines, serialize_records
+
+UNBOUNDED = 10_000_000
+
+
+def test_each_record_becomes_one_json_line():
+    lines = serialize_records([{"id": "a"}, {"id": "b"}, {"id": "c"}])
+
+    assert len(lines) == 3
+    assert [json.loads(line)["id"] for line in lines] == ["a", "b", "c"]
+
+
+def test_non_serializable_values_do_not_raise():
+    """An odd payload must not kill the flush."""
+    lines = serialize_records([{"id": "a", "when": object()}])
+
+    assert json.loads(lines[0])["id"] == "a"
+
+
+def test_records_that_fit_stay_in_one_object():
+    lines = serialize_records([{"id": f"r{i}"} for i in range(50)])
+
+    assert chunk_lines(lines, UNBOUNDED) == (lines,)
+
+
+def test_objects_are_capped_by_uncompressed_size():
+    lines = serialize_records([{"id": f"r{i}", "blob": "x" * 100} for i in range(10)])
+    line_bytes = len(lines[0].encode("utf-8")) + 1
+
+    chunks = chunk_lines(lines, line_bytes * 3)
+
+    assert [len(chunk) for chunk in chunks] == [3, 3, 3, 1]
+
+
+def test_oversized_single_record_is_sent_alone_not_stalled():
+    """A record too big for the cap must still go out, or it blocks everything behind it."""
+    lines = serialize_records([{"id": "small"}, {"id": "huge", "blob": "x" * 5000}, {"id": "small2"}])
+
+    chunks = chunk_lines(lines, 200)
+
+    assert sum(len(chunk) for chunk in chunks) == 3
+    huge = [chunk for chunk in chunks if any("huge" in line for line in chunk)]
+    assert len(huge) == 1
+    assert len(huge[0]) == 1
+
+
+def test_no_records_produces_no_objects():
+    assert chunk_lines((), UNBOUNDED) == ()
+
+
+def test_every_record_appears_exactly_once():
+    lines = serialize_records([{"id": f"r{i}"} for i in range(37)])
+
+    chunks = chunk_lines(lines, len(lines[0]) * 4)
+
+    assert [line for chunk in chunks for line in chunk] == list(lines)
+
+
+@pytest.mark.asyncio
+async def test_encode_lines_round_trips_through_gzip():
+    lines = serialize_records([{"id": f"r{i}"} for i in range(5)])
+
+    encoded = await encode_lines(lines)
+
+    assert encoded[:2] == b"\x1f\x8b"
+    assert gzip.decompress(encoded).decode("utf-8") == "\n".join(lines)
+
+
+@pytest.mark.asyncio
+async def test_encode_lines_compresses_repetitive_records():
+    lines = serialize_records([{"id": f"r{i}", "model": "gpt-4o", "cost": 0.01} for i in range(200)])
+
+    encoded = await encode_lines(lines)
+
+    assert len(encoded) < len(gzip.decompress(encoded)) / 2
diff --git a/tests/test_litellm/integrations/pointfive/test_upload_client.py b/tests/test_litellm/integrations/pointfive/test_upload_client.py
new file mode 100644
index 00000000000..50ef085386d
--- /dev/null
+++ b/tests/test_litellm/integrations/pointfive/test_upload_client.py
@@ -0,0 +1,378 @@
+import json
+from collections.abc import Sequence
+
+import httpx
+import pytest
+
+import litellm
+from litellm.integrations.pointfive.upload_client import PointFiveUploadClient
+from litellm.litellm_core_utils.url_utils import validate_url
+from litellm.types.integrations.pointfive import PointFiveUploadFailure
+
+API_URL = "https://api.pointfive.co/api/v1/ingestion"
+UPLOAD_URL = "https://uploads.example.invalid/some/object.ndjson.gz?signature=sig"
+OBJECT_KEY = "some/object.ndjson.gz"
+BODY = b"gzipped-bytes"
+
+
+def _presigned(status_code: int = 200) -> httpx.Response:
+    return _response(
+        status_code, {"uploadUrl": UPLOAD_URL, "objectKey": OBJECT_KEY, "expiresAt": "2026-08-25T14:35:00Z"}
+    )
+
+
+def _response(status_code: int, payload: object) -> httpx.Response:
+    return httpx.Response(status_code, text=json.dumps(payload))
+
+
+def _refused(status_code: int, error: str) -> httpx.Response:
+    """The body PointFive sends with every refusal."""
+    return _response(status_code, {"success": False, "error": error})
+
+
+def _accepted() -> httpx.Response:
+    return httpx.Response(200, text="")
+
+
+def _no_content() -> httpx.Response:
+    return httpx.Response(204, text="")
+
+
+class FakeHTTPClient:
+    """
+    Stands in for AsyncHTTPHandler, including its habit of raising on error statuses.
+
+    Scripted results are consumed in order, and the last one repeats, so a test that
+    cares about a single behaviour passes a single result.
+    """
+
+    def __init__(
+        self,
+        presign: Sequence[httpx.Response | Exception] | None = None,
+        put: Sequence[httpx.Response | Exception] | None = None,
+    ) -> None:
+        self.presign = list(presign) if presign else [_presigned()]  # mutable-ok: results are consumed by popping
+        self.put_results = list(put) if put else [_accepted()]  # mutable-ok: results are consumed by popping
+        self.presign_calls: list[dict] = []
+        self.put_calls: list[dict] = []
+
+    async def post(self, url, json=None, headers=None, **_):
+        self.presign_calls.append({"url": url, "json": json, "headers": headers or {}})
+        return _next_result(self.presign, url)
+
+    async def put(self, url, data=None, headers=None, follow_redirects=None, **_):
+        self.put_calls.append(
+            {"url": url, "data": data, "headers": headers or {}, "follow_redirects": follow_redirects}
+        )
+        return _next_result(self.put_results, url)
+
+
+def _next_result(results: list, url: str) -> httpx.Response:
+    result = results.pop(0) if len(results) > 1 else results[0]
+    if isinstance(result, Exception):
+        raise result
+    if result.status_code >= 300:
+        request = httpx.Request("POST", url)
+        raise httpx.HTTPStatusError(
+            "boom",
+            request=request,
+            response=httpx.Response(result.status_code, text=result.text, headers=result.headers),
+        )
+    return result
+
+
+async def _no_backoff(_seconds: float) -> None:
+    return None
+
+
+def _trusting_validator(url: str) -> tuple[str, str]:
+    """Stands in for validate_url so the fixture hosts need no DNS; the SSRF tests use the real one."""
+    return url, httpx.URL(url).host
+
+
+def _client(
+    http_client: FakeHTTPClient,
+    max_retries: int = 3,
+    api_url: str = API_URL,
+    validate_upload_url=_trusting_validator,
+) -> PointFiveUploadClient:
+    return PointFiveUploadClient(
+        api_key="p5tu_testkey",
+        api_url=api_url,
+        http_client=http_client,
+        max_retries=max_retries,
+        sleep=_no_backoff,
+        validate_upload_url=validate_upload_url,
+    )
+
+
+def _presigned_for(upload_url: str) -> httpx.Response:
+    return _response(200, {"uploadUrl": upload_url, "objectKey": OBJECT_KEY, "expiresAt": "2026-08-25T14:35:00Z"})
+
+
+@pytest.mark.asyncio
+async def test_uploads_the_body_to_the_url_the_api_returned():
+    http_client = FakeHTTPClient()
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == OBJECT_KEY
+    assert http_client.put_calls[0]["url"] == UPLOAD_URL
+    assert http_client.put_calls[0]["data"] == BODY
+
+
+@pytest.mark.asyncio
+async def test_presign_request_is_authenticated_and_sized():
+    http_client = FakeHTTPClient()
+
+    await _client(http_client).upload(BODY)
+
+    call = http_client.presign_calls[0]
+    assert call["url"] == "https://api.pointfive.co/api/v1/ingestion/upload-url"
+    assert call["headers"]["Authorization"] == "Bearer p5tu_testkey"
+    assert call["json"] == {"kind": "LITELLM", "byteCount": len(BODY)}
+
+
+@pytest.mark.asyncio
+async def test_a_trailing_slash_on_the_api_url_is_tolerated():
+    """A pasted URL often ends in a slash; it must not produce a double slash in the path."""
+    http_client = FakeHTTPClient()
+
+    await _client(http_client, api_url=API_URL + "/").upload(BODY)
+
+    assert http_client.presign_calls[0]["url"] == "https://api.pointfive.co/api/v1/ingestion/upload-url"
+
+
+@pytest.mark.asyncio
+async def test_no_bearer_token_is_sent_to_the_presigned_url():
+    """The URL carries its own authorization, so the api key must not travel with it."""
+    http_client = FakeHTTPClient()
+
+    await _client(http_client).upload(BODY)
+
+    assert "Authorization" not in http_client.put_calls[0]["headers"]
+
+
+@pytest.mark.asyncio
+async def test_the_upload_pins_the_host_and_never_follows_a_redirect():
+    http_client = FakeHTTPClient()
+
+    await _client(http_client).upload(BODY)
+
+    call = http_client.put_calls[0]
+    assert call["headers"]["Host"] == "uploads.example.invalid"
+    assert call["follow_redirects"] is False
+
+
+@pytest.mark.asyncio
+async def test_a_redirected_upload_is_refused_rather_than_followed():
+    """A presigned URL never redirects legitimately; following one is how a bad endpoint reaches inside."""
+    http_client = FakeHTTPClient(put=[httpx.Response(301, headers={"location": "http://169.254.169.254/"})])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure(
+        "presigned upload redirected with 301, refusing to follow", retryable=False
+    )
+    assert len(http_client.put_calls) == 1
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "upload_url",
+    [
+        "http://169.254.169.254/latest/meta-data",
+        "https://10.0.0.7/internal/bucket/object",
+        "http://127.0.0.1:9000/bucket/object",
+    ],
+)
+async def test_an_upload_url_inside_the_network_is_refused_before_any_bytes_leave(upload_url):
+    http_client = FakeHTTPClient(presign=[_presigned_for(upload_url)])
+
+    outcome = await _client(http_client, validate_upload_url=validate_url).upload(BODY)
+
+    assert isinstance(outcome, PointFiveUploadFailure)
+    assert not outcome.retryable
+    assert outcome.detail.startswith("presigned upload url refused: ")
+    assert http_client.put_calls == []
+
+
+@pytest.mark.asyncio
+async def test_an_operator_can_switch_destination_validation_off(monkeypatch):
+    """litellm.user_url_validation is the proxy-wide switch every SSRF guard honours."""
+    monkeypatch.setattr(litellm, "user_url_validation", False)
+    http_client = FakeHTTPClient(presign=[_presigned_for("http://10.0.0.7/bucket/object")])
+
+    outcome = await _client(http_client, validate_upload_url=validate_url).upload(BODY)
+
+    assert outcome == OBJECT_KEY
+    assert http_client.put_calls[0]["url"] == "http://10.0.0.7/bucket/object"
+    assert "Host" not in http_client.put_calls[0]["headers"]
+
+
+@pytest.mark.asyncio
+async def test_the_object_is_declared_as_gzipped_ndjson():
+    http_client = FakeHTTPClient()
+
+    await _client(http_client).upload(BODY)
+
+    assert http_client.put_calls[0]["headers"]["Content-Encoding"] == "gzip"
+    assert http_client.put_calls[0]["headers"]["Content-Type"] == "application/x-ndjson"
+
+
+@pytest.mark.asyncio
+async def test_each_retry_presigns_again():
+    """A retry must never reuse a URL that was consumed or has expired."""
+    http_client = FakeHTTPClient(put=[httpx.Response(503), _accepted()])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == OBJECT_KEY
+    assert len(http_client.presign_calls) == 2
+    assert len(http_client.put_calls) == 2
+
+
+@pytest.mark.asyncio
+async def test_retryable_upload_failure_gives_up_after_max_retries():
+    http_client = FakeHTTPClient(put=[httpx.Response(503)])
+
+    outcome = await _client(http_client, max_retries=2).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure("presigned upload returned 503, gave up after 2 attempts", retryable=True)
+    assert len(http_client.put_calls) == 2
+
+
+@pytest.mark.asyncio
+async def test_rejected_upload_is_not_retried():
+    http_client = FakeHTTPClient(put=[httpx.Response(403)])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure("presigned upload returned 403", retryable=False)
+    assert len(http_client.put_calls) == 1
+
+
+@pytest.mark.asyncio
+async def test_bad_api_key_is_not_retried():
+    http_client = FakeHTTPClient(presign=[httpx.Response(401)])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure("pointfive api returned 401", retryable=False)
+    assert http_client.put_calls == []
+
+
+@pytest.mark.asyncio
+async def test_the_reason_for_a_refusal_is_surfaced():
+    """A 403 means the key no longer maps to an integration; the operator needs to read why."""
+    http_client = FakeHTTPClient(presign=[_refused(403, "no integration accepts uploads from this api key")])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure(
+        "pointfive api returned 403, no integration accepts uploads from this api key", retryable=False
+    )
+    assert http_client.put_calls == []
+
+
+@pytest.mark.asyncio
+async def test_api_server_error_is_retried():
+    http_client = FakeHTTPClient(presign=[httpx.Response(503), _presigned()])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == OBJECT_KEY
+    assert len(http_client.presign_calls) == 2
+
+
+@pytest.mark.asyncio
+async def test_too_many_requests_is_retried():
+    http_client = FakeHTTPClient(presign=[httpx.Response(429), _presigned()])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == OBJECT_KEY
+    assert len(http_client.presign_calls) == 2
+
+
+@pytest.mark.asyncio
+async def test_unreachable_api_is_retried_then_reported_as_retryable():
+    http_client = FakeHTTPClient(presign=(ConnectionError("down"),))
+
+    outcome = await _client(http_client, max_retries=2).upload(BODY)
+
+    assert isinstance(outcome, PointFiveUploadFailure)
+    assert outcome.retryable
+    assert "unreachable" in outcome.detail
+    assert len(http_client.presign_calls) == 2
+
+
+@pytest.mark.asyncio
+async def test_malformed_api_body_is_not_retried():
+    http_client = FakeHTTPClient(presign=[_response(200, {"objectKey": "k"})])
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure("pointfive api returned an unreadable body", retryable=False)
+    assert http_client.put_calls == []
+
+
+@pytest.mark.asyncio
+async def test_a_body_that_is_not_json_is_reported_as_unreadable():
+    http_client = FakeHTTPClient(presign=(httpx.Response(200, text="<html>gateway</html>"),))
+
+    outcome = await _client(http_client).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure("pointfive api returned an unreadable body", retryable=False)
+    assert http_client.put_calls == []
+
+
+@pytest.mark.asyncio
+async def test_ping_reports_a_live_shipper():
+    http_client = FakeHTTPClient(presign=(_no_content(),))
+
+    failure = await _client(http_client).ping()
+
+    assert failure is None
+    assert http_client.presign_calls[0]["url"] == "https://api.pointfive.co/api/v1/ingestion/ping"
+    assert http_client.presign_calls[0]["json"] == {"kind": "LITELLM"}
+
+
+@pytest.mark.asyncio
+async def test_ping_surfaces_a_revoked_key():
+    http_client = FakeHTTPClient(presign=(_refused(403, "no integration accepts uploads from this api key"),))
+
+    failure = await _client(http_client).ping()
+
+    assert failure is not None
+    assert not failure.retryable
+    assert "no integration accepts uploads from this api key" in failure.detail
+
+
+@pytest.mark.asyncio
+async def test_ping_surfaces_an_unreachable_api():
+    http_client = FakeHTTPClient(presign=(ConnectionError("down"),))
+
+    failure = await _client(http_client).ping()
+
+    assert failure is not None
+    assert failure.retryable
+
+
+@pytest.mark.asyncio
+async def test_a_transport_fault_on_the_upload_itself_is_retryable():
+    http_client = FakeHTTPClient(put=(ConnectionError("reset"),))
+
+    outcome = await _client(http_client, max_retries=1).upload(BODY)
+
+    assert isinstance(outcome, PointFiveUploadFailure)
+    assert outcome.retryable
+    assert "presigned upload unreachable" in outcome.detail
+
+
+@pytest.mark.asyncio
+async def test_a_client_that_may_not_try_at_all_says_so():
+    """max_upload_retries is validated as >= 1, so this guards the loop against a future zero."""
+    outcome = await _client(FakeHTTPClient(), max_retries=0).upload(BODY)
+
+    assert outcome == PointFiveUploadFailure("max_upload_retries must be at least 1", retryable=False)
diff --git a/tests/test_litellm/integrations/test_custom_guardrail.py b/tests/test_litellm/integrations/test_custom_guardrail.py
index cd8d609cf71..ddc8439a83a 100644
--- a/tests/test_litellm/integrations/test_custom_guardrail.py
+++ b/tests/test_litellm/integrations/test_custom_guardrail.py
@@ -1842,12 +1842,14 @@ class _ApplyStyleGuardrail(CustomGuardrail):
         self.block = block
         self.apply_called = False
         self.seen_texts = None
+        self.seen_request_data = None
 
     async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
         from fastapi import HTTPException
 
         self.apply_called = True
         self.seen_texts = inputs.get("texts")
+        self.seen_request_data = request_data
         if self.block:
             raise HTTPException(status_code=400, detail={"error": "Violated moderation policy"})
         return inputs
@@ -2646,6 +2648,91 @@ class TestCustomGuardrailPostCallSuccessDeploymentHook:
     which starved every later callback in litellm.callbacks (notably the lazily-appended
     VectorStorePreCallHook that attaches provider_specific_fields["search_results"])."""
 
+    @pytest.mark.asyncio
+    async def test_apply_guardrail_retains_request_identity(self) -> None:
+        from litellm.types.guardrails import GuardrailEventHooks
+        from litellm.types.utils import Choices, Message, ModelResponse
+
+        guardrail: Final = _ApplyStyleGuardrail(block=False)
+        guardrail.event_hook = GuardrailEventHooks.post_call
+        request_data: Final = {"guardrails": ["apply-style-guardrail"]}
+        response: Final = ModelResponse(choices=[Choices(message=Message(content="review me"))])
+
+        await guardrail.async_post_call_success_deployment_hook(
+            request_data=request_data, response=response, call_type=CallTypes.acompletion
+        )
+
+        assert guardrail.seen_request_data is request_data
+        assert guardrail.seen_texts == ["review me"]
+        assert "guardrail_to_apply" not in request_data
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("call_type", (None, CallTypes.acompletion))
+    async def test_apply_guardrail_masks_response_and_records_metadata(self, call_type: CallTypes | None) -> None:
+        from litellm.proxy.guardrails.guardrail_hooks.litellm_content_filter.content_filter import (
+            ContentFilterGuardrail,
+        )
+        from litellm.types.guardrails import BlockedWord, ContentFilterAction, GuardrailEventHooks
+        from litellm.types.utils import Choices, Message, ModelResponse
+
+        guardrail: Final = ContentFilterGuardrail(
+            guardrail_name="response-filter",
+            event_hook=GuardrailEventHooks.post_call,
+            blocked_words=[BlockedWord(keyword="secret", action=ContentFilterAction.MASK)],
+        )
+        request_data: Final = {"guardrails": ["response-filter"]}
+        response: Final = ModelResponse(choices=[Choices(message=Message(content="a secret"))])
+
+        result: Final = await guardrail.async_post_call_success_deployment_hook(
+            request_data=request_data, response=response, call_type=call_type
+        )
+
+        assert isinstance(result, ModelResponse)
+        assert result.choices[0].message.content == f"a {guardrail.keyword_redaction_tag}"
+        entries: Final = _guardrail_entries(request_data)
+        assert len(entries) == 1
+        assert entries[0]["guardrail_name"] == "response-filter"
+        assert entries[0]["guardrail_mode"] == "post_call"
+        assert "guardrail_to_apply" not in request_data
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("error_type", (None, RuntimeError, asyncio.CancelledError))
+    async def test_dispatch_cleans_up_request_on_every_exit(self, error_type: type[BaseException] | None) -> None:
+        from contextlib import nullcontext
+
+        from litellm.integrations.custom_logger import CustomLogger
+        from litellm.types.utils import LLMResponseTypes, ModelResponse
+
+        error: Final = error_type("dispatch interrupted") if error_type is not None else None
+
+        class Dispatch(CustomLogger):
+            request_data: dict[str, object] | None = None
+
+            async def async_post_call_success_hook(
+                self, data: dict[str, object], user_api_key_dict: UserAPIKeyAuth, response: LLMResponseTypes
+            ) -> LLMResponseTypes:
+                self.request_data = data
+                if error is not None:
+                    raise error
+                return response
+
+        dispatch: Final = Dispatch()
+
+        class Guardrail(_ApplyStyleGuardrail):
+            def _deployment_hook_target(self) -> CustomLogger:
+                return dispatch
+
+        guardrail: Final = Guardrail(block=False)
+        guardrail.event_hook = GuardrailEventHooks.post_call
+        request_data: Final = {"guardrails": ["apply-style-guardrail"]}
+        with pytest.raises(error_type) if error_type is not None else nullcontext():
+            await guardrail.async_post_call_success_deployment_hook(
+                request_data=request_data, response=ModelResponse(), call_type=CallTypes.acompletion
+            )
+
+        assert dispatch.request_data is request_data
+        assert "guardrail_to_apply" not in request_data
+
     @pytest.mark.asyncio
     async def test_returns_none_when_request_has_no_guardrails(self):
         from litellm.types.utils import ModelResponse
@@ -2740,4 +2827,5 @@ class TestCustomGuardrailPostCallSuccessDeploymentHook:
 
         assert result is response
         assert response.choices[0].message.content == "filtered response"
-        assert request_data == {"guardrails": ["test-guardrail"]}
+        assert "guardrail_to_apply" not in request_data
+        assert len(_guardrail_entries(request_data)) == 1
diff --git a/tests/test_litellm/integrations/test_langfuse.py b/tests/test_litellm/integrations/test_langfuse.py
index d36878e455f..87e76499b84 100644
--- a/tests/test_litellm/integrations/test_langfuse.py
+++ b/tests/test_litellm/integrations/test_langfuse.py
@@ -1341,6 +1341,257 @@ def _emit(logger: LangFuseLogger, *, metadata=None, headers=None):
     )
 
 
+@pytest.mark.parametrize("level", ["DEFAULT", "ERROR"])
+@pytest.mark.parametrize(
+    "headers,metadata,expected_id",
+    [
+        ({"x-litellm-session-id": "session-7125"}, {}, "call"),
+        ({"X-Claude-Code-Session-Id": "session-7125"}, {}, "call"),
+        ({"x-session-id": "session-7125"}, {}, "call"),
+        ({"session-id": "session-7125", "user-agent": "codex_cli_rs/1.0"}, {}, "call"),
+        ({"thread-id": "session-7125", "user-agent": "codex-tui"}, {}, "call"),
+        ({"session_id": "session-7125", "user-agent": "Codex 1.0"}, {}, "call"),
+        ({"conversation_id": "session-7125", "user-agent": "codex_vscode/1.0"}, {}, "call"),
+        ({"x-litellm-session-id": "short"}, {}, "call"),
+        ({"x-litellm-trace-id": "session-7125"}, {}, "session-7125"),
+        (
+            {"X-LiteLLM-Trace-Id": "session-7125", "x-litellm-session-id": "session-7125"},
+            {},
+            "session-7125",
+        ),
+        (
+            {"x-litellm-session-id": "session-7125", "langfuse_trace_id": "session-7125"},
+            {},
+            "session-7125",
+        ),
+        (
+            {"x-litellm-session-id": "session-7125", "langfuse_trace_id": "explicit-trace"},
+            {},
+            "explicit-trace",
+        ),
+        (
+            {"x-litellm-session-id": "session-7125", "langfuse_existing_trace_id": "existing-trace"},
+            {},
+            "existing-trace",
+        ),
+        (
+            {"x-litellm-session-id": "session-7125", "langfuse_session_id": "custom-session"},
+            {},
+            "call",
+        ),
+        (
+            {"x-litellm-session-id": "short", "langfuse_session_id": "custom-session"},
+            {},
+            "call",
+        ),
+        (
+            {"X-Claude-Code-Session-Id": "session-7125", "langfuse_session_id": "custom-session"},
+            {},
+            "call",
+        ),
+        (
+            {"x-session-id": "session-7125", "langfuse_session_id": "custom-session"},
+            {},
+            "call",
+        ),
+        (
+            {
+                "session-id": "session-7125",
+                "user-agent": "codex_cli_rs/1.0",
+                "langfuse_session_id": "custom-session",
+            },
+            {},
+            "call",
+        ),
+        (
+            {
+                "x-litellm-session-id": "session-7125",
+                "langfuse_session_id": "custom-session",
+                "x-litellm-trace-id": "explicit-trace",
+            },
+            {},
+            "explicit-trace",
+        ),
+        (
+            {
+                "x-litellm-session-id": "session-7125",
+                "langfuse_session_id": "custom-session",
+                "langfuse_trace_id": "explicit-trace",
+            },
+            {},
+            "explicit-trace",
+        ),
+        (
+            {
+                "x-litellm-session-id": "session-7125",
+                "langfuse_session_id": "custom-session",
+                "langfuse_existing_trace_id": "existing-trace",
+            },
+            {},
+            "existing-trace",
+        ),
+        ({}, {"trace_id": "session-7125", "session_id": "session-7125"}, "session-7125"),
+        ({}, {"trace_id": "explicit-trace", "session_id": "session-7125"}, "explicit-trace"),
+        (
+            {"x-vendor-session-id": "short"},
+            {"trace_id": "short", "session_id": "short"},
+            "short",
+        ),
+        (
+            {"x-session-id": "invalid value"},
+            {"trace_id": "invalid value", "session_id": "invalid value"},
+            "invalid value",
+        ),
+        (
+            {"session-id": "session-7125", "user-agent": "codexfoo/1.0"},
+            {"trace_id": "session-7125", "session_id": "session-7125"},
+            "session-7125",
+        ),
+        (
+            {"x-vendor-session-id": "short"},
+            {"trace_id": "session-7125", "session_id": "session-7125"},
+            "session-7125",
+        ),
+        ({}, {}, "call"),
+    ],
+)
+def test_session_header_trace_provenance(headers, metadata, expected_id, level):
+    from starlette.datastructures import Headers
+
+    from litellm.proxy.litellm_pre_call_utils import (
+        LiteLLMProxyRequestSetup,
+        clean_headers,
+        redact_credential_headers,
+    )
+
+    logger: Final = _steering_logger()
+    for turn in range(2):
+        call_id = f"call-{turn}"
+        request_headers = Headers(headers)
+        data = LiteLLMProxyRequestSetup.add_litellm_metadata_from_request_headers(
+            headers=request_headers, data={"metadata": dict(metadata)}, _metadata_variable_name="metadata"
+        )
+        original_metadata = dict(data["metadata"])
+        now = datetime.datetime.now()
+        result = logger.log_event_on_langfuse(
+            kwargs={
+                "call_type": "completion",
+                "litellm_call_id": call_id,
+                "litellm_trace_id": data.get("litellm_trace_id"),
+                "litellm_params": {
+                    "metadata": data["metadata"],
+                    "proxy_server_request": {"headers": redact_credential_headers(clean_headers(request_headers))},
+                },
+                "messages": [{"role": "user", "content": f"turn {turn}"}],
+                "optional_params": {},
+            },
+            response_obj=(
+                None
+                if level == "ERROR"
+                else litellm.ModelResponse(choices=[{"message": {"role": "assistant", "content": "OK"}}])
+            ),
+            start_time=now,
+            end_time=now,
+            level=level,
+            status_message="provider error" if level == "ERROR" else None,
+        )
+        trace_params = logger.Langfuse.trace.call_args.kwargs
+        assert trace_params["id"] == (call_id if expected_id == "call" else expected_id)
+        assert result["trace_id"] == trace_params["id"]
+        if expected_id != "existing-trace":
+            assert trace_params["session_id"] == headers.get("langfuse_session_id", original_metadata.get("session_id"))
+        steering = {key[len("langfuse_") :]: value for key, value in headers.items() if key.startswith("langfuse_")}
+        assert data["metadata"] == {**original_metadata, **steering}
+
+
+def test_session_header_trace_without_call_id_keeps_session_alias():
+    logger: Final = _steering_logger()
+    now: Final = datetime.datetime.now()
+
+    result: Final = logger.log_event_on_langfuse(
+        kwargs={
+            "call_type": "completion",
+            "litellm_call_id": "",
+            "litellm_params": {
+                "metadata": {"trace_id": "session-7125", "session_id": "session-7125"},
+                "proxy_server_request": {"headers": {"x-litellm-session-id": "session-7125"}},
+            },
+            "messages": [{"role": "user", "content": "no call id"}],
+            "optional_params": {},
+        },
+        response_obj=litellm.ModelResponse(choices=[{"message": {"role": "assistant", "content": "OK"}}]),
+        start_time=now,
+        end_time=now,
+    )
+
+    assert logger.Langfuse.trace.call_args.kwargs["id"] == "session-7125"
+    assert result["trace_id"] == "session-7125"
+
+
+def test_every_proxy_session_header_shape_is_classified_as_a_session_alias():
+    """The classifier must cover every header shape the proxy turns into a chain id."""
+    from litellm.integrations.langfuse.langfuse import _is_session_header_trace
+    from litellm.proxy.litellm_pre_call_utils import (
+        _CODEX_SESSION_ID_HEADERS,
+        get_chain_id_from_headers,
+    )
+
+    session: Final = "session-7125-abcdef"
+    session_shapes: Final = (
+        {"x-litellm-session-id": session},
+        {"X-Claude-Code-Session-Id": session},
+        {"x-session-id": session},
+        *({header: session, "user-agent": "codex_cli_rs/1.0"} for header in _CODEX_SESSION_ID_HEADERS),
+    )
+    for headers in session_shapes:
+        assert get_chain_id_from_headers(dict(headers)) == session, headers
+        assert _is_session_header_trace(session, session, {"headers": headers}) is True, headers
+
+    explicit_trace: Final = {"x-litellm-trace-id": session, "x-litellm-session-id": session}
+    assert get_chain_id_from_headers(dict(explicit_trace)) == session
+    assert _is_session_header_trace(session, session, {"headers": explicit_trace}) is False
+
+
+@pytest.mark.parametrize(
+    "proxy_server_request",
+    [None, {}, {"headers": None}],
+    ids=["no-proxy-request", "no-headers-key", "null-headers"],
+)
+def test_sdk_caller_without_request_headers_keeps_its_trace(proxy_server_request):
+    """A direct SDK caller has no request headers, so a session-shaped trace id stays the caller's."""
+    logger: Final = _steering_logger()
+    now: Final = datetime.datetime.now()
+
+    result: Final = logger.log_event_on_langfuse(
+        kwargs={
+            "call_type": "completion",
+            "litellm_call_id": "call-0",
+            "litellm_params": {
+                "metadata": {"trace_id": "session-7125", "session_id": "session-7125"},
+                "proxy_server_request": proxy_server_request,
+            },
+            "messages": [{"role": "user", "content": "sdk turn"}],
+            "optional_params": {},
+        },
+        response_obj=litellm.ModelResponse(choices=[{"message": {"role": "assistant", "content": "OK"}}]),
+        start_time=now,
+        end_time=now,
+    )
+
+    assert logger.Langfuse.trace.call_args.kwargs["id"] == "session-7125"
+    assert result["trace_id"] == "session-7125"
+
+
+def test_session_header_classifier_survives_non_string_header_keys():
+    """A non-string header key must not cost the caller its whole trace."""
+    from litellm.integrations.langfuse.langfuse import _is_session_header_trace
+
+    session: Final = "session-7125-abcdef"
+    headers: Final = {7: "numeric key", "x-litellm-session-id": session}
+    assert _is_session_header_trace(session, session, {"headers": headers}) is True
+    assert _is_session_header_trace(session, session, {"headers": {7: "numeric key"}}) is False
+
+
 def test_mask_input_header_false_keeps_the_prompt():
     logger = _steering_logger()
 
diff --git a/tests/test_litellm/integrations/test_prometheus_client_ip_user_agent.py b/tests/test_litellm/integrations/test_prometheus_client_ip_user_agent.py
index ea661d2ea78..004ac4dbffb 100644
--- a/tests/test_litellm/integrations/test_prometheus_client_ip_user_agent.py
+++ b/tests/test_litellm/integrations/test_prometheus_client_ip_user_agent.py
@@ -84,6 +84,7 @@ async def test_async_post_call_success_hook_includes_client_ip_user_agent():
         "litellm.integrations.prometheus.PrometheusLogger.__init__", return_value=None
     ):
         logger = PrometheusLogger()
+        logger._emit_input_sequence_length_label = False
         logger.litellm_proxy_total_requests_metric = MagicMock()
         logger.get_labels_for_metric = MagicMock(
             return_value=["client_ip", "user_agent"]
diff --git a/tests/test_litellm/integrations/test_prometheus_input_sequence_length_label.py b/tests/test_litellm/integrations/test_prometheus_input_sequence_length_label.py
new file mode 100644
index 00000000000..bc922061544
--- /dev/null
+++ b/tests/test_litellm/integrations/test_prometheus_input_sequence_length_label.py
@@ -0,0 +1,428 @@
+import asyncio
+import datetime
+from collections.abc import Mapping
+from copy import deepcopy
+from typing import Final, cast
+
+import pytest
+from prometheus_client import REGISTRY
+from prometheus_client.samples import Sample
+
+import litellm
+from litellm.integrations.prometheus import PrometheusLogger
+from litellm.types.integrations.prometheus import (
+    PrometheusMetricLabels,
+    UserAPIKeyLabelNames,
+    UserAPIKeyLabelValues,
+    get_input_sequence_length_bucket,
+)
+from litellm.types.utils import StandardLoggingPayload
+
+LATENCY_METRICS: Final = (
+    "litellm_llm_api_latency_metric",
+    "litellm_llm_api_time_to_first_token_metric",
+    "litellm_request_total_latency_metric",
+)
+FLAG: Final = "prometheus_emit_input_sequence_length_label"
+
+
+def _clear_prometheus_registry() -> None:
+    for collector in tuple(REGISTRY._collector_to_names):  # pyright: ignore[reportPrivateUsage]  # test registry reset
+        REGISTRY.unregister(collector)
+
+
+@pytest.fixture(autouse=True)
+def isolated_registry(monkeypatch: pytest.MonkeyPatch):
+    _clear_prometheus_registry()
+    monkeypatch.setattr(litellm, FLAG, False)
+    yield
+    _clear_prometheus_registry()
+
+
+@pytest.mark.parametrize("metric", LATENCY_METRICS)
+def test_input_sequence_length_label_is_opt_in(monkeypatch: pytest.MonkeyPatch, metric: str):
+    assert UserAPIKeyLabelNames.INPUT_SEQUENCE_LENGTH.value not in PrometheusMetricLabels.get_labels(metric)
+
+    monkeypatch.setattr(litellm, FLAG, True)
+    assert UserAPIKeyLabelNames.INPUT_SEQUENCE_LENGTH.value in PrometheusMetricLabels.get_labels(metric)
+
+
+def test_input_sequence_length_label_stays_off_non_latency_metrics(monkeypatch: pytest.MonkeyPatch):
+    monkeypatch.setattr(litellm, FLAG, True)
+    assert UserAPIKeyLabelNames.INPUT_SEQUENCE_LENGTH.value not in PrometheusMetricLabels.get_labels(
+        "litellm_proxy_total_requests_metric"
+    )
+
+
+@pytest.mark.parametrize(
+    "prompt_tokens, expected",
+    [
+        (None, "unknown"),
+        (0, "0-1k"),
+        (999, "0-1k"),
+        (1_000, "1k-4k"),
+        (3_999, "1k-4k"),
+        (4_000, "4k-16k"),
+        (15_999, "4k-16k"),
+        (16_000, "16k-64k"),
+        (63_999, "16k-64k"),
+        (64_000, "64k+"),
+        (10_000_000, "64k+"),
+        (-1, "unknown"),
+    ],
+)
+def test_input_sequence_length_bucket_boundaries(prompt_tokens: int | None, expected: str):
+    assert get_input_sequence_length_bucket(prompt_tokens) == expected
+
+
+def test_user_api_key_label_values_carries_input_sequence_length():
+    values: Final = UserAPIKeyLabelValues(input_sequence_length="4k-16k")
+
+    assert values.input_sequence_length == "4k-16k"
+    assert values.model_dump()["input_sequence_length"] == "4k-16k"
+
+
+def _assert_latency_metrics(expected: str | None, stream: bool = True, queue_time: float = 0) -> None:
+    samples: Final = tuple(sample for metric in REGISTRY.collect() for sample in metric.samples)
+    for metric, duration in zip(LATENCY_METRICS, (2, 1, 3 + queue_time)):
+        counts: Final = tuple(sample for sample in samples if sample.name == f"{metric}_count")
+        sums: Final = tuple(sample for sample in samples if sample.name == f"{metric}_sum")
+        buckets: Final = tuple(sample for sample in samples if sample.name == f"{metric}_bucket")
+        if not stream and metric == "litellm_llm_api_time_to_first_token_metric":
+            assert not counts and not sums and not buckets
+            continue
+        assert len(counts) == len(sums) == 1
+        assert counts[0].value == 1
+        assert sums[0].value == pytest.approx(duration)
+        assert buckets and any(sample.labels["le"] == "+Inf" for sample in buckets)
+        assert all(sample.value == int(float(sample.labels["le"]) >= duration) for sample in buckets)
+        assert all(sample.labels.get("input_sequence_length") == expected for sample in (*counts, *sums, *buckets))
+
+
+def _non_target_samples() -> tuple[Sample, ...]:
+    return tuple(
+        sample
+        for metric in REGISTRY.collect()
+        if metric.name not in LATENCY_METRICS
+        for sample in metric.samples
+        if "input_sequence_length" in sample.labels and not sample.name.endswith("_created")
+    )
+
+
+def _standard_logging_payload(now: datetime.datetime, prompt_tokens: int) -> StandardLoggingPayload:
+    return cast(
+        StandardLoggingPayload,
+        {
+            "id": "t",
+            "call_type": "completion",
+            "response_cost": 0.001,
+            "status": "success",
+            "total_tokens": prompt_tokens + 20,
+            "prompt_tokens": prompt_tokens,
+            "completion_tokens": 20,
+            "startTime": now - datetime.timedelta(seconds=3),
+            "endTime": now,
+            "completionStartTime": now - datetime.timedelta(seconds=1),
+            "model": "gpt-4o-mini",
+            "model_id": "model-123",
+            "model_group": "gpt-4o-mini",
+            "api_base": "https://api.openai.com",
+            "custom_llm_provider": "openai",
+            "request_tags": [],
+            "stream": True,
+            "metadata": {
+                "user_api_key_hash": "h",
+                "user_api_key_alias": "a",
+                "user_api_key_team_id": "t",
+                "user_api_key_team_alias": "ta",
+                "user_api_key_user_id": "u",
+                "user_api_key_user_email": "e@x.com",
+                "user_api_key_org_id": None,
+                "user_api_key_org_alias": None,
+                "requester_metadata": None,
+                "user_api_key_end_user_id": None,
+                "usage_object": None,
+            },
+            "hidden_params": {"litellm_overhead_time_ms": None, "additional_headers": None},
+        },
+    )
+
+
+def _success_kwargs(
+    now: datetime.datetime, prompt_tokens: int, requester_metadata: Mapping[str, object] | None = None
+) -> Mapping[str, object]:
+    payload: Final = _standard_logging_payload(now, prompt_tokens)
+    return {
+        "model": "gpt-4o-mini",
+        "litellm_params": {"metadata": {}},
+        "standard_logging_object": {
+            **payload,
+            "metadata": {**payload["metadata"], "requester_metadata": requester_metadata},
+        },
+        "stream": True,
+        "start_time": now - datetime.timedelta(seconds=3),
+        "api_call_start_time": now - datetime.timedelta(seconds=2),
+        "completion_start_time": now - datetime.timedelta(seconds=1),
+        "end_time": now,
+    }
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("flag_at_request_time", (True, False))
+async def test_logger_emits_bucket_from_its_startup_label_set(
+    monkeypatch: pytest.MonkeyPatch, flag_at_request_time: bool
+):
+    now: Final = datetime.datetime.now()
+    monkeypatch.setattr(litellm, FLAG, True)
+    logger: Final = PrometheusLogger()
+    monkeypatch.setattr(litellm, FLAG, flag_at_request_time)
+
+    await logger.async_log_success_event(dict(_success_kwargs(now, prompt_tokens=4_000)), None, now, now)
+
+    _assert_latency_metrics("4k-16k")
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("response", "combined_usage", "expected"),
+    (
+        ({"id": "moderation", "results": []}, None, "unknown"),
+        ({"usage": None}, None, "unknown"),
+        ({"usage": {}}, None, "unknown"),
+        ({"usage": {"completion_tokens": 3}}, None, "unknown"),
+        ({"usage": {"total_tokens": 5}}, None, "unknown"),
+        ({"usage": {"prompt_tokens": 0}}, None, "0-1k"),
+        ({"usage": {"prompt_tokens": 4_000}}, None, "4k-16k"),
+        ({"usage": {"input_tokens": 0, "output_tokens": 3, "total_tokens": 3}}, None, "0-1k"),
+        ({"usage": {"input_tokens": 4_000, "output_tokens": 3, "total_tokens": 4_003}}, None, "4k-16k"),
+        (litellm.ModelResponse(usage=litellm.Usage(prompt_tokens=0)), None, "0-1k"),
+        (None, litellm.Usage(prompt_tokens=0), "0-1k"),
+    ),
+)
+@pytest.mark.parametrize("include_usage_metadata", (True, False))
+async def test_logger_distinguishes_missing_usage_from_reported_zero(
+    monkeypatch: pytest.MonkeyPatch,
+    response: object,
+    combined_usage: object,
+    expected: str,
+    include_usage_metadata: bool,
+):
+    from litellm.litellm_core_utils.litellm_logging import StandardLoggingPayloadSetup
+
+    now: Final = datetime.datetime.now()
+    monkeypatch.setattr(litellm, FLAG, True)
+    logger: Final = PrometheusLogger()
+    usage: Final = StandardLoggingPayloadSetup.get_usage_as_dict(
+        response_obj=response if isinstance(response, dict) else None
+    )
+
+    payload: Final = _standard_logging_payload(now, usage.get("prompt_tokens", 0))
+    await logger.async_log_success_event(
+        {
+            **_success_kwargs(now, prompt_tokens=usage.get("prompt_tokens", 0)),
+            "combined_usage_object": combined_usage,
+            "standard_logging_object": {
+                **payload,
+                "metadata": {**payload["metadata"], "usage_object": usage if include_usage_metadata else None},
+            },
+        },
+        response,
+        now,
+        now,
+    )
+
+    _assert_latency_metrics(expected)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("total_tokens", (None, 0, 5_000))
+@pytest.mark.parametrize("prompt_tokens", (0, 4_000))
+async def test_upstream_total_only_usage_has_unknown_input_length(
+    monkeypatch: pytest.MonkeyPatch, total_tokens: int | None, prompt_tokens: int
+):
+    import httpx
+
+    from litellm.litellm_core_utils.litellm_logging import Logging, StandardLoggingPayloadSetup
+    from litellm.proxy.pass_through_endpoints.upstream_usage_headers import apply_upstream_reported_usage
+
+    now: Final = datetime.datetime.now()
+    monkeypatch.setattr(litellm, FLAG, True)
+    logger: Final = PrometheusLogger()
+    logging_obj: Final = Logging(
+        model="gpt-4o-mini",
+        messages=[],
+        stream=True,
+        call_type="pass_through_endpoint",
+        start_time=now,
+        litellm_call_id="test-call-id",
+        function_id="1",
+    )
+    headers: Final = httpx.Headers(
+        {
+            "x-litellm-response-cost": "0.001",
+            **({"x-litellm-total-tokens": str(total_tokens)} if total_tokens is not None else {}),
+        }
+    )
+    reported: Final = apply_upstream_reported_usage(logging_obj=logging_obj, headers=headers)
+    assert reported is not None
+    combined_usage: Final = logging_obj.model_call_details.get("combined_usage_object")
+    response: Final = {"usage": {"prompt_tokens": prompt_tokens}}
+    usage: Final = StandardLoggingPayloadSetup.get_usage_as_dict(response, combined_usage)
+    payload: Final = _standard_logging_payload(now, usage.get("prompt_tokens", 0))
+
+    await logger.async_log_success_event(
+        {
+            **logging_obj.model_call_details,
+            **_success_kwargs(now, usage.get("prompt_tokens", 0)),
+            "standard_logging_object": {**payload, "metadata": {**payload["metadata"], "usage_object": usage}},
+        },
+        response,
+        now,
+        now,
+    )
+
+    _assert_latency_metrics("unknown" if total_tokens is not None else get_input_sequence_length_bucket(prompt_tokens))
+
+
+@pytest.mark.asyncio
+async def test_logger_built_with_flag_off_emits_no_bucket_label(monkeypatch: pytest.MonkeyPatch):
+    now: Final = datetime.datetime.now()
+    logger: Final = PrometheusLogger()
+    monkeypatch.setattr(litellm, FLAG, True)
+
+    await logger.async_log_success_event(dict(_success_kwargs(now, prompt_tokens=4_000)), None, now, now)
+
+    _assert_latency_metrics(None)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("flag_at_startup", (True, False))
+@pytest.mark.parametrize("stream", (True, False))
+@pytest.mark.parametrize(
+    "metadata",
+    (
+        None,
+        {},
+        {"input_sequence_length": None},
+        {"input_sequence_length": False},
+        {"input_sequence_length": True},
+        {"input_sequence_length": 0},
+        {"input_sequence_length": []},
+        {"input_sequence_length": {}},
+        {"input_sequence_length": ""},
+        {"input_sequence_length": "from-metadata"},
+    ),
+)
+async def test_custom_input_length_label_is_scoped_to_target_histograms(
+    monkeypatch: pytest.MonkeyPatch, flag_at_startup: bool, stream: bool, metadata: Mapping[str, object] | None
+):
+    now: Final = datetime.datetime.now()
+    monkeypatch.setattr(litellm, "custom_prometheus_metadata_labels", ["input_sequence_length"])
+    kwargs: Final = {
+        **_success_kwargs(now, prompt_tokens=4_000, requester_metadata=metadata),
+        "stream": stream,
+        "litellm_params": {"metadata": {"queue_time_seconds": 0.25}},
+    }
+    original_kwargs: Final = deepcopy(kwargs)
+    baseline_logger: Final = PrometheusLogger()
+    await baseline_logger.async_log_success_event(kwargs, None, now, now)
+    baseline_samples: Final = _non_target_samples()
+    _clear_prometheus_registry()
+    monkeypatch.setattr(litellm, FLAG, flag_at_startup)
+    logger: Final = PrometheusLogger()
+    monkeypatch.setattr(litellm, FLAG, not flag_at_startup)
+
+    await logger.async_log_success_event(kwargs, None, now, now)
+
+    assert kwargs == original_kwargs
+    custom_value: Final = (metadata or {}).get("input_sequence_length")
+    expected: Final = custom_value if isinstance(custom_value, str) else ("4k-16k" if flag_at_startup else "None")
+    _assert_latency_metrics(expected, stream=stream, queue_time=0.25)
+    assert all(logger.get_labels_for_metric(metric).count("input_sequence_length") == 1 for metric in LATENCY_METRICS)
+    non_target_samples: Final = _non_target_samples()
+    assert {
+        "litellm_requests_metric_total",
+        "litellm_spend_metric_total",
+        "litellm_total_tokens_metric_total",
+        "litellm_request_queue_time_seconds_count",
+        "litellm_deployment_success_responses_total",
+    }.issubset({sample.name for sample in non_target_samples})
+    assert non_target_samples == baseline_samples
+    queue_sum: Final = tuple(
+        sample for sample in non_target_samples if sample.name == "litellm_request_queue_time_seconds_sum"
+    )
+    assert len(queue_sum) == 1 and queue_sum[0].value == 0.25
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("enabled", (True, False))
+async def test_concurrent_requests_keep_independent_buckets(monkeypatch: pytest.MonkeyPatch, enabled: bool):
+    now: Final = datetime.datetime.now()
+    monkeypatch.setattr(litellm, FLAG, enabled)
+    logger: Final = PrometheusLogger()
+    cases: Final = (
+        (None, "unknown"),
+        (0, "0-1k"),
+        (1_000, "1k-4k"),
+        (4_000, "4k-16k"),
+        (16_000, "16k-64k"),
+        (64_000, "64k+"),
+    )
+    calls: Final = tuple(
+        (
+            {**_success_kwargs(now, prompt_tokens=tokens or 0), "stream": stream},
+            {"usage": {"prompt_tokens": tokens}} if tokens is not None else None,
+        )
+        for tokens, _ in cases
+        for stream in (True, False)
+        for _ in range(2)
+    )
+    original_calls: Final = deepcopy(calls)
+
+    await asyncio.gather(*(logger.async_log_success_event(kwargs, response, now, now) for kwargs, response in calls))
+
+    assert calls == original_calls
+    samples: Final = tuple(sample for metric in REGISTRY.collect() for sample in metric.samples)
+    for metric, duration in zip(LATENCY_METRICS, (2, 1, 3)):
+        expected_count: Final = 2 if metric == "litellm_llm_api_time_to_first_token_metric" else 4
+        counts: Final = tuple(sample for sample in samples if sample.name == f"{metric}_count")
+        sums: Final = tuple(sample for sample in samples if sample.name == f"{metric}_sum")
+        buckets: Final = tuple(sample for sample in samples if sample.name == f"{metric}_bucket")
+        expected: Final = (
+            {bucket: expected_count for _, bucket in cases} if enabled else {None: expected_count * len(cases)}
+        )
+        assert len(counts) == len(sums) == len(expected)
+        assert {sample.labels.get("input_sequence_length"): sample.value for sample in counts} == expected
+        assert {sample.labels.get("input_sequence_length"): sample.value for sample in sums} == {
+            bucket: count * duration for bucket, count in expected.items()
+        }
+        assert sum(sample.value for sample in buckets if sample.labels["le"] == "+Inf") == expected_count * len(cases)
+        assert all(
+            sample.value
+            == expected[sample.labels.get("input_sequence_length")] * int(float(sample.labels["le"]) >= duration)
+            for sample in buckets
+        )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("enabled", (True, False))
+async def test_failed_request_does_not_observe_latency(monkeypatch: pytest.MonkeyPatch, enabled: bool):
+    now: Final = datetime.datetime.now()
+    monkeypatch.setattr(litellm, FLAG, enabled)
+    monkeypatch.setattr(litellm, "custom_prometheus_metadata_labels", ["input_sequence_length"])
+    logger: Final = PrometheusLogger()
+    kwargs: Final = {
+        **_success_kwargs(now, prompt_tokens=4_000),
+        "standard_logging_object": {**_standard_logging_payload(now, 4_000), "status": "failure"},
+        "exception": RuntimeError("upstream request failed"),
+    }
+
+    await logger.async_log_failure_event(kwargs, None, now, now)
+
+    samples: Final = tuple(sample for metric in REGISTRY.collect() for sample in metric.samples)
+    assert not any(sample.name.startswith(LATENCY_METRICS) for sample in samples)
+    for metric in ("litellm_llm_api_failed_requests_metric_total", "litellm_deployment_failure_responses_total"):
+        counts: Final = tuple(sample for sample in samples if sample.name == metric)
+        assert len(counts) == 1
+        assert counts[0].value == 1
+        assert counts[0].labels["input_sequence_length"] == "None"
diff --git a/tests/test_litellm/integrations/test_s3_v2.py b/tests/test_litellm/integrations/test_s3_v2.py
index a037284d7c1..08d37297ab1 100644
--- a/tests/test_litellm/integrations/test_s3_v2.py
+++ b/tests/test_litellm/integrations/test_s3_v2.py
@@ -1,10 +1,19 @@
 import asyncio
+import re
+import sys
+import textwrap
+import uuid
+from contextlib import asynccontextmanager
 from datetime import datetime
-from unittest.mock import MagicMock, patch
+from pathlib import Path
+from unittest.mock import AsyncMock, MagicMock, call, patch
 
+import httpx
 import pytest
 
 from litellm.integrations.s3_v2 import S3Logger
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
+from litellm.types.integrations.s3_v2 import s3BatchLoggingElement
 from litellm.types.utils import StandardLoggingPayload
 
 
@@ -21,9 +30,7 @@ class TestS3V2UnitTests:
         source_code = inspect.getsource(s3_v2)
 
         # Verify that json.dumps is not used directly in the code
-        assert (
-            "json.dumps(" not in source_code
-        ), "S3 v2 should not use json.dumps directly"
+        assert "json.dumps(" not in source_code, "S3 v2 should not use json.dumps directly"
 
     @patch("asyncio.create_task")
     @patch("litellm.integrations.s3_v2.CustomBatchLogger.periodic_flush")
@@ -86,12 +93,8 @@ class TestS3V2UnitTests:
         call_args_minio = s3_logger_minio.async_httpx_client.put.call_args
         assert call_args_minio is not None
         url_minio = call_args_minio[0][0]
-        expected_minio_url = (
-            "https://minio.example.com:9000/litellm-logs/2025-09-14/test-key.json"
-        )
-        assert (
-            url_minio == expected_minio_url
-        ), f"Expected MinIO URL {expected_minio_url}, got {url_minio}"
+        expected_minio_url = "https://minio.example.com:9000/litellm-logs/2025-09-14/test-key.json"
+        assert url_minio == expected_minio_url, f"Expected MinIO URL {expected_minio_url}, got {url_minio}"
 
         # Test 3: Custom endpoint without bucket name (should fall back to default)
         s3_logger_no_bucket = S3Logger(
@@ -136,12 +139,8 @@ class TestS3V2UnitTests:
             call_args_sync = mock_sync_client.put.call_args
             assert call_args_sync is not None
             url_sync = call_args_sync[0][0]
-            expected_sync_url = (
-                "https://custom.s3.endpoint.com/sync-bucket/2025-09-14/test-key.json"
-            )
-            assert (
-                url_sync == expected_sync_url
-            ), f"Expected sync URL {expected_sync_url}, got {url_sync}"
+            expected_sync_url = "https://custom.s3.endpoint.com/sync-bucket/2025-09-14/test-key.json"
+            assert url_sync == expected_sync_url, f"Expected sync URL {expected_sync_url}, got {url_sync}"
 
         # Test 5: Download method with custom endpoint
         s3_logger_download = S3Logger(
@@ -158,19 +157,15 @@ class TestS3V2UnitTests:
         s3_logger_download.async_httpx_client = AsyncMock()
         s3_logger_download.async_httpx_client.get.return_value = mock_download_response
 
-        result = asyncio.run(
-            s3_logger_download._download_object_from_s3(
-                "2025-09-14/download-test-key.json"
-            )
-        )
+        result = asyncio.run(s3_logger_download._download_object_from_s3("2025-09-14/download-test-key.json"))
 
         call_args_download = s3_logger_download.async_httpx_client.get.call_args
         assert call_args_download is not None
         url_download = call_args_download[0][0]
         expected_download_url = "https://download.s3.endpoint.com/download-bucket/2025-09-14/download-test-key.json"
-        assert (
-            url_download == expected_download_url
-        ), f"Expected download URL {expected_download_url}, got {url_download}"
+        assert url_download == expected_download_url, (
+            f"Expected download URL {expected_download_url}, got {url_download}"
+        )
 
         assert result == {"downloaded": "data"}
 
@@ -216,12 +211,8 @@ class TestS3V2UnitTests:
         call_args = s3_logger_virtual.async_httpx_client.put.call_args
         assert call_args is not None
         url = call_args[0][0]
-        expected_url = (
-            "https://test-bucket.s3.custom-endpoint.com/2025-09-14/test-key.json"
-        )
-        assert (
-            url == expected_url
-        ), f"Expected virtual-hosted-style URL {expected_url}, got {url}"
+        expected_url = "https://test-bucket.s3.custom-endpoint.com/2025-09-14/test-key.json"
+        assert url == expected_url, f"Expected virtual-hosted-style URL {expected_url}, got {url}"
 
         # Test 2: Path-style (default behavior with s3_use_virtual_hosted_style=False)
         s3_logger_path = S3Logger(
@@ -241,12 +232,8 @@ class TestS3V2UnitTests:
         call_args_path = s3_logger_path.async_httpx_client.put.call_args
         assert call_args_path is not None
         url_path = call_args_path[0][0]
-        expected_path_url = (
-            "https://s3.custom-endpoint.com/test-bucket/2025-09-14/test-key.json"
-        )
-        assert (
-            url_path == expected_path_url
-        ), f"Expected path-style URL {expected_path_url}, got {url_path}"
+        expected_path_url = "https://s3.custom-endpoint.com/test-bucket/2025-09-14/test-key.json"
+        assert url_path == expected_path_url, f"Expected path-style URL {expected_path_url}, got {url_path}"
 
         # Test 3: Virtual-hosted-style with http protocol
         s3_logger_http = S3Logger(
@@ -266,12 +253,10 @@ class TestS3V2UnitTests:
         call_args_http = s3_logger_http.async_httpx_client.put.call_args
         assert call_args_http is not None
         url_http = call_args_http[0][0]
-        expected_http_url = (
-            "http://http-bucket.minio.local:9000/2025-09-14/test-key.json"
+        expected_http_url = "http://http-bucket.minio.local:9000/2025-09-14/test-key.json"
+        assert url_http == expected_http_url, (
+            f"Expected virtual-hosted-style URL with http {expected_http_url}, got {url_http}"
         )
-        assert (
-            url_http == expected_http_url
-        ), f"Expected virtual-hosted-style URL with http {expected_http_url}, got {url_http}"
 
         # Test 4: Sync upload method with virtual-hosted-style
         s3_logger_sync_virtual = S3Logger(
@@ -295,12 +280,10 @@ class TestS3V2UnitTests:
             call_args_sync = mock_sync_client.put.call_args
             assert call_args_sync is not None
             url_sync = call_args_sync[0][0]
-            expected_sync_url = (
-                "https://sync-bucket.storage.example.com/2025-09-14/test-key.json"
+            expected_sync_url = "https://sync-bucket.storage.example.com/2025-09-14/test-key.json"
+            assert url_sync == expected_sync_url, (
+                f"Expected virtual-hosted-style sync URL {expected_sync_url}, got {url_sync}"
             )
-            assert (
-                url_sync == expected_sync_url
-            ), f"Expected virtual-hosted-style sync URL {expected_sync_url}, got {url_sync}"
 
         # Test 5: Download method with virtual-hosted-style
         s3_logger_download_virtual = S3Logger(
@@ -316,34 +299,27 @@ class TestS3V2UnitTests:
         mock_download_response.status_code = 200
         mock_download_response.json = MagicMock(return_value={"downloaded": "data"})
         s3_logger_download_virtual.async_httpx_client = AsyncMock()
-        s3_logger_download_virtual.async_httpx_client.get.return_value = (
-            mock_download_response
-        )
+        s3_logger_download_virtual.async_httpx_client.get.return_value = mock_download_response
 
-        result = asyncio.run(
-            s3_logger_download_virtual._download_object_from_s3(
-                "2025-09-14/download-test-key.json"
-            )
-        )
+        result = asyncio.run(s3_logger_download_virtual._download_object_from_s3("2025-09-14/download-test-key.json"))
 
         call_args_download = s3_logger_download_virtual.async_httpx_client.get.call_args
         assert call_args_download is not None
         url_download = call_args_download[0][0]
         expected_download_url = "https://download-bucket.download.endpoint.com/2025-09-14/download-test-key.json"
-        assert (
-            url_download == expected_download_url
-        ), f"Expected virtual-hosted-style download URL {expected_download_url}, got {url_download}"
+        assert url_download == expected_download_url, (
+            f"Expected virtual-hosted-style download URL {expected_download_url}, got {url_download}"
+        )
 
         assert result == {"downloaded": "data"}
 
     @patch("asyncio.create_task")
     @patch("litellm.integrations.s3_v2.CustomBatchLogger.periodic_flush")
-    def test_s3_v2_put_url_encodes_spaces_in_object_key(
-        self, mock_periodic_flush, mock_create_task
-    ):
-        import requests
+    def test_s3_v2_put_url_encodes_spaces_in_object_key(self, mock_periodic_flush, mock_create_task):
         from unittest.mock import AsyncMock
 
+        import requests
+
         from litellm.types.integrations.s3_v2 import s3BatchLoggingElement
 
         mock_periodic_flush.return_value = None
@@ -487,9 +463,7 @@ async def test_async_upload_exhausts_retries_on_persistent_503():
     # All 3 attempts return 503
     response_503 = MagicMock()
     response_503.status_code = 503
-    response_503.raise_for_status = MagicMock(
-        side_effect=Exception("503 Service Unavailable")
-    )
+    response_503.raise_for_status = MagicMock(side_effect=Exception("503 Service Unavailable"))
 
     logger.async_httpx_client = AsyncMock()
     logger.async_httpx_client.put = AsyncMock(return_value=response_503)
@@ -528,12 +502,12 @@ async def test_async_upload_no_retry_on_4xx():
         s3_object_download_filename="test-no-retry.json",
     )
 
-    response_403 = MagicMock()
-    response_403.status_code = 403
-    response_403.raise_for_status = MagicMock(side_effect=Exception("403 Forbidden"))
+    response_400 = MagicMock()
+    response_400.status_code = 400
+    response_400.raise_for_status = MagicMock(side_effect=Exception("400 Bad Request"))
 
     logger.async_httpx_client = AsyncMock()
-    logger.async_httpx_client.put = AsyncMock(return_value=response_403)
+    logger.async_httpx_client.put = AsyncMock(return_value=response_400)
 
     with patch.object(logger, "handle_callback_failure") as mock_failure:
         await logger.async_upload_data_to_s3(test_element)
@@ -543,6 +517,190 @@ async def test_async_upload_no_retry_on_4xx():
     mock_failure.assert_called_once_with(callback_name="S3Logger")
 
 
+_SIGV4_ACCESS_KEY = re.compile(r"Credential=(AKIA\d+)/")
+
+
+@pytest.fixture
+def rotating_profile(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> str:
+    """
+    A real botocore profile whose credential_process hands out a new key generation on every call and
+    expires inside the advisory refresh window, so RefreshableCredentials re-runs it on every property read.
+    """
+    counter = tmp_path / "generation"
+    script = tmp_path / "rotate_credentials.py"
+    script.write_text(
+        textwrap.dedent(
+            f"""
+            import json, sys
+            from datetime import datetime, timedelta, timezone
+            from pathlib import Path
+
+            counter = Path({str(counter)!r})
+            generation = int(counter.read_text()) if counter.exists() else 0
+            counter.write_text(str(generation + 1))
+            expiry = (datetime.now(timezone.utc) + timedelta(minutes=12)).strftime("%Y-%m-%dT%H:%M:%SZ")
+            json.dump(
+                {{
+                    "Version": 1,
+                    "AccessKeyId": f"AKIA{{generation}}",
+                    "SecretAccessKey": f"secret-{{generation}}",
+                    "SessionToken": f"token-{{generation}}",
+                    "Expiration": expiry,
+                }},
+                sys.stdout,
+            )
+            """
+        )
+    )
+    profile = f"rotating-{uuid.uuid4().hex}"
+    (tmp_path / "config").write_text(f"[profile {profile}]\ncredential_process = {sys.executable} {script}\n")
+    monkeypatch.setenv("AWS_CONFIG_FILE", str(tmp_path / "config"))
+    return profile
+
+
+def _generation(request: httpx.Request) -> tuple[str, str]:
+    """(access key generation, session token generation) SigV4 baked into one request."""
+    access_key = _SIGV4_ACCESS_KEY.search(request.headers["Authorization"])
+    assert access_key is not None
+    return access_key.group(1).removeprefix("AKIA"), request.headers["X-Amz-Security-Token"].removeprefix("token-")
+
+
+@asynccontextmanager
+async def _s3_logger_on_production_handler(profile: str, statuses: list[int]):
+    """
+    S3Logger wired to the real AsyncHTTPHandler over an httpx MockTransport that answers with the given
+    statuses in order, so the handler's own raise_for_status behaviour is exercised end to end.
+    """
+    requests: list[httpx.Request] = []
+    replies = iter(statuses)
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        requests.append(request)
+        return httpx.Response(next(replies), request=request, text="<Error><Code>SignatureDoesNotMatch</Code></Error>")
+
+    handler = AsyncHTTPHandler()
+    handler.client = httpx.AsyncClient(transport=httpx.MockTransport(respond))
+    logger = S3Logger(
+        s3_bucket_name="test-bucket",
+        s3_region_name="us-east-1",
+        s3_aws_profile_name=profile,
+        s3_flush_interval=3600,
+    )
+    logger.async_httpx_client = handler
+    with patch("asyncio.sleep", new_callable=AsyncMock) as mock_sleep:
+        yield logger, requests, mock_sleep
+    await handler.client.aclose()
+
+
+@pytest.mark.asyncio
+async def test_async_upload_signs_with_one_frozen_credential_snapshot(rotating_profile: str, caplog):
+    """
+    RefreshableCredentials refreshes on every property read once inside the advisory window, so signing
+    off the live object would mix the access key of one generation with the token of the next.
+    """
+    test_element = s3BatchLoggingElement(
+        s3_object_key="2025-09-14/test-frozen.json",
+        payload={"test": "frozen"},
+        s3_object_download_filename="test-frozen.json",
+    )
+    async with _s3_logger_on_production_handler(rotating_profile, [200]) as (logger, requests, _):
+        await logger.async_upload_data_to_s3(test_element)
+
+    assert len(requests) == 1
+    access_key_generation, token_generation = _generation(requests[0])
+    assert access_key_generation == token_generation
+    assert "Error uploading to s3" not in caplog.text
+
+
+@pytest.mark.asyncio
+async def test_async_upload_retries_403_with_fresh_credentials_and_signature(rotating_profile: str, caplog):
+    """
+    A 403 (SignatureDoesNotMatch after an IMDS rotation) must be retried, and the retry must fetch
+    credentials again and carry a signature computed from that newer generation.
+    """
+    test_element = s3BatchLoggingElement(
+        s3_object_key="2025-09-14/test-403.json",
+        payload={"test": "403"},
+        s3_object_download_filename="test-403.json",
+    )
+    async with _s3_logger_on_production_handler(rotating_profile, [403, 200]) as (logger, requests, mock_sleep):
+        await logger.async_upload_data_to_s3(test_element)
+
+    assert len(requests) == 2
+    first_key, first_token = _generation(requests[0])
+    second_key, second_token = _generation(requests[1])
+    assert first_key == first_token
+    assert second_key == second_token
+    assert int(second_key) > int(first_key)
+    assert requests[1].headers["Authorization"] != requests[0].headers["Authorization"]
+    mock_sleep.assert_awaited_once_with(1)
+    assert "Error uploading to s3" not in caplog.text
+
+
+@pytest.mark.asyncio
+async def test_async_upload_exhausts_403_retries_through_production_http_handler(rotating_profile: str, caplog):
+    test_element = s3BatchLoggingElement(
+        s3_object_key="2025-09-14/test-403-exhausted.json",
+        payload={"test": "403-exhausted"},
+        s3_object_download_filename="test-403-exhausted.json",
+    )
+    async with _s3_logger_on_production_handler(rotating_profile, [403, 403, 403]) as (logger, requests, mock_sleep):
+        await logger.async_upload_data_to_s3(test_element)
+
+    assert len(requests) == 3
+    assert mock_sleep.await_args_list == [call(1), call(2)]
+    assert "Error uploading to s3" in caplog.text
+
+
+@pytest.mark.asyncio
+async def test_async_upload_does_not_retry_404_through_production_http_handler(rotating_profile: str, caplog):
+    test_element = s3BatchLoggingElement(
+        s3_object_key="2025-09-14/test-404.json",
+        payload={"test": "404"},
+        s3_object_download_filename="test-404.json",
+    )
+    async with _s3_logger_on_production_handler(rotating_profile, [404]) as (logger, requests, mock_sleep):
+        await logger.async_upload_data_to_s3(test_element)
+
+    assert len(requests) == 1
+    mock_sleep.assert_not_awaited()
+    assert "Error uploading to s3" in caplog.text
+
+
+def test_sync_upload_retries_403_with_fresh_signature(rotating_profile: str, monkeypatch: pytest.MonkeyPatch):
+    monkeypatch.setenv("AWS_PROFILE", rotating_profile)
+    logger = S3Logger(s3_bucket_name="test-bucket", s3_region_name="us-east-1", s3_flush_interval=3600)
+    test_element = s3BatchLoggingElement(
+        s3_object_key="2025-09-14/test-sync-403.json",
+        payload={"test": "sync-403"},
+        s3_object_download_filename="test-sync-403.json",
+    )
+    requests: list[httpx.Request] = []
+    replies = iter([403, 200])
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        requests.append(request)
+        return httpx.Response(next(replies), request=request)
+
+    handler = HTTPHandler()
+    handler.client = httpx.Client(transport=httpx.MockTransport(respond))
+    with (
+        patch(  # test-quality-ok: sync upload builds its HTTPHandler per call, there is no injection seam for it
+            "litellm.integrations.s3_v2._get_httpx_client", return_value=handler
+        ),
+        patch("time.sleep") as mock_sleep,
+    ):
+        logger.upload_data_to_s3(test_element)
+
+    assert len(requests) == 2
+    first_key, first_token = _generation(requests[0])
+    second_key, second_token = _generation(requests[1])
+    assert first_key == first_token
+    assert second_key == second_token
+    assert int(second_key) > int(first_key)
+    mock_sleep.assert_called_once_with(1)
+
+
 def test_sync_upload_retries_on_s3_503():
     """
     Test that the sync upload_data_to_s3 retries on transient S3 503.
@@ -626,9 +784,7 @@ async def test_async_log_event_skips_when_standard_logging_object_missing():
 
     # Nothing should have been queued (catches the case where code falls
     # through without returning and appends None to the queue)
-    assert (
-        len(logger.log_queue) == 0
-    ), "log_queue should be empty when standard_logging_object is missing"
+    assert len(logger.log_queue) == 0, "log_queue should be empty when standard_logging_object is missing"
 
 
 @pytest.mark.asyncio
@@ -767,20 +923,18 @@ async def test_s3_verify_false_handling(monkeypatch: pytest.MonkeyPatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "test-bucket",
-                "s3_endpoint_url": "https://localhost:443",
-                "s3_aws_access_key_id": "minioadmin",
-                "s3_aws_secret_access_key": "minioadmin",
-                "s3_region_name": "us-east-1",
-                "s3_verify": False,  # This should NOT be ignored
-                "s3_use_ssl": False,  # This should also NOT be ignored
-            },
+            "s3_bucket_name": "test-bucket",
+            "s3_endpoint_url": "https://localhost:443",
+            "s3_aws_access_key_id": "minioadmin",
+            "s3_aws_secret_access_key": "minioadmin",
+            "s3_region_name": "us-east-1",
+            "s3_verify": False,  # This should NOT be ignored
+            "s3_use_ssl": False,  # This should also NOT be ignored
+        },
     )
 
     with patch("asyncio.create_task"):
-        with patch(
-            "litellm.integrations.s3_v2.get_async_httpx_client"
-        ) as mock_get_client:
+        with patch("litellm.integrations.s3_v2.get_async_httpx_client") as mock_get_client:
             mock_client = AsyncMock()
             mock_get_client.return_value = mock_client
 
@@ -788,22 +942,16 @@ async def test_s3_verify_false_handling(monkeypatch: pytest.MonkeyPatch):
             logger = S3Logger()
 
             # Verify s3_verify is False, not None
-            assert (
-                logger.s3_verify is False
-            ), f"Expected s3_verify=False, got {logger.s3_verify}"
-            assert (
-                logger.s3_use_ssl is False
-            ), f"Expected s3_use_ssl=False, got {logger.s3_use_ssl}"
+            assert logger.s3_verify is False, f"Expected s3_verify=False, got {logger.s3_verify}"
+            assert logger.s3_use_ssl is False, f"Expected s3_use_ssl=False, got {logger.s3_use_ssl}"
 
             # Verify that get_async_httpx_client was called with ssl_verify=False
             mock_get_client.assert_called_once()
             call_kwargs = mock_get_client.call_args.kwargs
-            assert (
-                "params" in call_kwargs
-            ), "params should be passed to get_async_httpx_client"
-            assert call_kwargs["params"] == {
-                "ssl_verify": False
-            }, f"Expected ssl_verify=False in params, got {call_kwargs.get('params')}"
+            assert "params" in call_kwargs, "params should be passed to get_async_httpx_client"
+            assert call_kwargs["params"] == {"ssl_verify": False}, (
+                f"Expected ssl_verify=False in params, got {call_kwargs.get('params')}"
+            )
 
 
 @pytest.mark.asyncio
@@ -820,17 +968,15 @@ async def test_s3_verify_none_handling(monkeypatch: pytest.MonkeyPatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "test-bucket",
-                "s3_aws_access_key_id": "test-key",
-                "s3_aws_secret_access_key": "test-secret",
-                "s3_region_name": "us-east-1",
-            },
+            "s3_bucket_name": "test-bucket",
+            "s3_aws_access_key_id": "test-key",
+            "s3_aws_secret_access_key": "test-secret",
+            "s3_region_name": "us-east-1",
+        },
     )
 
     with patch("asyncio.create_task"):
-        with patch(
-            "litellm.integrations.s3_v2.get_async_httpx_client"
-        ) as mock_get_client:
+        with patch("litellm.integrations.s3_v2.get_async_httpx_client") as mock_get_client:
             mock_client = AsyncMock()
             mock_get_client.return_value = mock_client
 
@@ -838,9 +984,7 @@ async def test_s3_verify_none_handling(monkeypatch: pytest.MonkeyPatch):
             logger = S3Logger()
 
             # Verify s3_verify is None (default)
-            assert (
-                logger.s3_verify is None
-            ), f"Expected s3_verify=None, got {logger.s3_verify}"
+            assert logger.s3_verify is None, f"Expected s3_verify=None, got {logger.s3_verify}"
 
             # Verify that get_async_httpx_client was called
             mock_get_client.assert_called_once()
@@ -868,13 +1012,13 @@ async def test_s3_verify_false_creates_httpx_client_with_verify_false(monkeypatc
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "test-bucket",
-                "s3_endpoint_url": "https://localhost:443",
-                "s3_aws_access_key_id": "minioadmin",
-                "s3_aws_secret_access_key": "minioadmin",
-                "s3_region_name": "us-east-1",
-                "s3_verify": False,
-            },
+            "s3_bucket_name": "test-bucket",
+            "s3_endpoint_url": "https://localhost:443",
+            "s3_aws_access_key_id": "minioadmin",
+            "s3_aws_secret_access_key": "minioadmin",
+            "s3_region_name": "us-east-1",
+            "s3_verify": False,
+        },
     )
 
     with patch("asyncio.create_task"):
@@ -890,9 +1034,7 @@ async def test_s3_verify_false_creates_httpx_client_with_verify_false(monkeypatc
             httpx_client = logger.async_httpx_client.client
             # Check the _verify attribute (httpx internal)
             if hasattr(httpx_client, "_verify"):
-                assert (
-                    httpx_client._verify is False
-                ), f"Expected httpx client _verify=False, got {httpx_client._verify}"
+                assert httpx_client._verify is False, f"Expected httpx client _verify=False, got {httpx_client._verify}"
 
 
 @pytest.mark.asyncio
@@ -910,13 +1052,13 @@ async def test_s3_verify_false_async_client(monkeypatch: pytest.MonkeyPatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "test-bucket",
-                "s3_endpoint_url": "https://localhost:443",
-                "s3_aws_access_key_id": "minioadmin",
-                "s3_aws_secret_access_key": "minioadmin",
-                "s3_region_name": "us-east-1",
-                "s3_verify": False,
-            },
+            "s3_bucket_name": "test-bucket",
+            "s3_endpoint_url": "https://localhost:443",
+            "s3_aws_access_key_id": "minioadmin",
+            "s3_aws_secret_access_key": "minioadmin",
+            "s3_region_name": "us-east-1",
+            "s3_verify": False,
+        },
     )
 
     with patch("asyncio.create_task"):
@@ -948,9 +1090,9 @@ async def test_s3_verify_false_async_client(monkeypatch: pytest.MonkeyPatch):
         if hasattr(logger.async_httpx_client, "client"):
             httpx_client = logger.async_httpx_client.client
             if hasattr(httpx_client, "_verify"):
-                assert (
-                    httpx_client._verify is False
-                ), f"Expected async httpx client _verify=False, got {httpx_client._verify}"
+                assert httpx_client._verify is False, (
+                    f"Expected async httpx client _verify=False, got {httpx_client._verify}"
+                )
 
 
 @pytest.mark.asyncio
@@ -1017,9 +1159,7 @@ def patch_asyncio_create_task():
         (True, True, None, None, ""),
     ],
 )
-def test_s3_object_key_prefix_combinations(
-    use_team_prefix, use_key_prefix, team_alias, key_alias, expected_prefix
-):
+def test_s3_object_key_prefix_combinations(use_team_prefix, use_key_prefix, team_alias, key_alias, expected_prefix):
     """
     Validate correct S3 prefix composition for team alias + key alias combinations.
     """
@@ -1490,9 +1630,7 @@ def test_s3_callback_params_override_does_not_mutate_inputs(monkeypatch):
     logger = S3Logger(s3_callback_params_override=override)
     assert logger.s3_bucket_name == "resolved-bucket"
     assert override["s3_bucket_name"] == "os.environ/MY_AUDIT_BUCKET"
-    assert (
-        litellm.s3_callback_params["s3_bucket_name"] == "os.environ/MY_AUDIT_BUCKET"
-    )
+    assert litellm.s3_callback_params["s3_bucket_name"] == "os.environ/MY_AUDIT_BUCKET"
 
 
 def test_s3_callback_params_override_none_falls_back_to_global(monkeypatch):
@@ -1520,9 +1658,7 @@ def _expected_content_md5(payload: dict) -> str:
     from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
 
     json_string = safe_dumps(payload)
-    return base64.b64encode(
-        hashlib.md5(json_string.encode("utf-8"), usedforsecurity=False).digest()
-    ).decode()
+    return base64.b64encode(hashlib.md5(json_string.encode("utf-8"), usedforsecurity=False).digest()).decode()
 
 
 def _require_non_security_md5(monkeypatch):
@@ -1658,9 +1794,9 @@ def test_s3_server_side_encryption_read_from_callback_params(monkeypatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "from-global",
-                "s3_server_side_encryption": "aws:kms",
-            },
+            "s3_bucket_name": "from-global",
+            "s3_server_side_encryption": "aws:kms",
+        },
     )
     logger = S3Logger()
     assert logger.s3_server_side_encryption == "aws:kms"
@@ -1789,10 +1925,10 @@ def test_s3_sse_kms_key_id_read_from_callback_params(monkeypatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "from-global",
-                "s3_server_side_encryption": "aws:kms",
-                "s3_sse_kms_key_id": "arn:aws:kms:us-east-1:111122223333:key/test-key-id",
-            },
+            "s3_bucket_name": "from-global",
+            "s3_server_side_encryption": "aws:kms",
+            "s3_sse_kms_key_id": "arn:aws:kms:us-east-1:111122223333:key/test-key-id",
+        },
     )
     logger = S3Logger()
     assert logger.s3_sse_kms_key_id == ("arn:aws:kms:us-east-1:111122223333:key/test-key-id")
@@ -1863,10 +1999,10 @@ def test_kms_key_id_dropped_when_algorithm_is_not_kms(monkeypatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "from-global",
-                "s3_server_side_encryption": "AES256",
-                "s3_sse_kms_key_id": "arn:aws:kms:us-east-1:111122223333:key/test-key-id",
-            },
+            "s3_bucket_name": "from-global",
+            "s3_server_side_encryption": "AES256",
+            "s3_sse_kms_key_id": "arn:aws:kms:us-east-1:111122223333:key/test-key-id",
+        },
     )
     logger = S3Logger()
     assert logger.s3_server_side_encryption == "AES256"
@@ -1884,10 +2020,10 @@ def test_non_string_algorithm_is_dropped_and_valid_key_id_is_rescued(monkeypatch
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "from-global",
-                "s3_server_side_encryption": True,
-                "s3_sse_kms_key_id": "arn:aws:kms:us-east-1:111122223333:key/test-key-id",
-            },
+            "s3_bucket_name": "from-global",
+            "s3_server_side_encryption": True,
+            "s3_sse_kms_key_id": "arn:aws:kms:us-east-1:111122223333:key/test-key-id",
+        },
     )
     logger = S3Logger()
     assert logger.s3_server_side_encryption == "aws:kms"
@@ -1902,10 +2038,10 @@ def test_non_string_key_id_is_dropped_and_valid_algorithm_is_kept(monkeypatch):
         litellm,
         "s3_callback_params",
         {
-                "s3_bucket_name": "from-global",
-                "s3_server_side_encryption": "aws:kms",
-                "s3_sse_kms_key_id": 12345,
-            },
+            "s3_bucket_name": "from-global",
+            "s3_server_side_encryption": "aws:kms",
+            "s3_sse_kms_key_id": 12345,
+        },
     )
     logger = S3Logger()
     assert logger.s3_server_side_encryption == "aws:kms"
@@ -2045,6 +2181,7 @@ async def test_download_signs_object_key_with_space_the_way_s3_does():
         headers=call.kwargs["headers"],
     )
 
+
 _RESERVED_CHAR_KEYS = (
     "2026-08-21/time-05-29-36_resp_bGl0ZWxsbTpjdXN0b20=.json",
     "session=logs/2026-08-21/time-05-29-36_abc.json",
diff --git a/tests/test_litellm/litellm_core_utils/event_loop_lag.py b/tests/test_litellm/litellm_core_utils/event_loop_lag.py
new file mode 100644
index 00000000000..1cac0365547
--- /dev/null
+++ b/tests/test_litellm/litellm_core_utils/event_loop_lag.py
@@ -0,0 +1,40 @@
+import asyncio
+import time
+from collections.abc import Awaitable, Callable
+from typing import Final, TypeVar
+
+import litellm
+
+T = TypeVar("T")
+
+
+def warm_tokenizer(model: str) -> None:
+    litellm.token_counter(model=model, text="load the tokenizer before anything is timed")
+
+
+async def loop_wake_lags(until: asyncio.Event) -> tuple[float, ...]:
+    async def wake_lag() -> float:
+        started: Final = time.perf_counter()
+        await asyncio.sleep(0.001)
+        return time.perf_counter() - started - 0.001
+
+    return tuple([await wake_lag() for _ in iter(until.is_set, True)])
+
+
+async def timed_with_loop_lags(run: Callable[[], Awaitable[T]]) -> tuple[T, float, tuple[float, ...]]:
+    finished: Final = asyncio.Event()
+
+    async def timed() -> tuple[T, float]:
+        await asyncio.sleep(0)
+        started: Final = time.perf_counter()
+        try:
+            return await run(), time.perf_counter() - started
+        finally:
+            finished.set()
+
+    (result, took), lags = await asyncio.gather(timed(), loop_wake_lags(finished))
+    return result, took, lags
+
+
+def assert_loop_stayed_free(took: float, lags: tuple[float, ...]) -> None:
+    assert max(lags) < took / 4, f"the event loop stalled {max(lags):.3f}s during a {took:.3f}s count"
diff --git a/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_llm_cost_calc_utils.py b/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_llm_cost_calc_utils.py
index 65a6dd2a4ca..fbb9d178390 100644
--- a/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_llm_cost_calc_utils.py
+++ b/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_llm_cost_calc_utils.py
@@ -1,9 +1,11 @@
 import json
+from datetime import datetime, timezone
 
 import pytest
 from fastapi.testclient import TestClient
 
 import litellm
+from litellm._internal_context import pinned_billing_time
 from litellm.litellm_core_utils.llm_cost_calc.tool_call_cost_tracking import (
     StandardBuiltInToolCostTracking,
 )
@@ -27,10 +29,10 @@ from litellm.types.utils import (
 )
 
 from litellm.litellm_core_utils.llm_cost_calc.utils import (
+    BilledTokenRates,
     CostCalculatorUtils,
     PromptTokensDetailsResult,
     TokenRates,
-    TokenTypeCostBreakdown,
     _calculate_input_cost,
     _get_token_base_cost,
     _is_off_peak,
@@ -38,6 +40,7 @@ from litellm.litellm_core_utils.llm_cost_calc.utils import (
     apply_off_peak_pricing,
     calculate_cache_writing_cost,
     generic_cost_per_token,
+    get_billed_token_rates,
     get_token_type_cost_breakdown,
 )
 from litellm.types.utils import CacheCreationTokenDetails, Usage
@@ -3906,6 +3909,200 @@ def test_token_type_cost_breakdown_reconciles_with_generic_total(_local_model_co
     assert text_input_cost + breakdown.cache_read_cost == pytest.approx(prompt_cost)
 
 
+def _custom_priced_usage() -> Usage:
+    return Usage(
+        prompt_tokens=1000,
+        completion_tokens=500,
+        total_tokens=1500,
+        prompt_tokens_details=PromptTokensDetailsWrapper(cached_tokens=800, cache_creation_tokens=100),
+        completion_tokens_details=CompletionTokensDetailsWrapper(reasoning_tokens=200),
+    )
+
+
+def test_token_type_cost_breakdown_prices_custom_pricing_from_its_flat_rates():
+    """
+    A custom-priced deployment, usually absent from the cost map, used to get zero cache and
+    reasoning lines while its total already billed cache tokens at the custom cache rates.
+    The lines must come from the same flat rates: a configured cache rate, else the input
+    rate for cache tokens and the output rate for reasoning tokens.
+    """
+    from litellm.types.utils import CostPerToken
+
+    breakdown = get_token_type_cost_breakdown(
+        model="openai/onprem-model",
+        custom_llm_provider="openai",
+        usage=_custom_priced_usage(),
+        custom_cost_per_token=CostPerToken(
+            input_cost_per_token=1e-6, output_cost_per_token=2e-6, cache_read_input_token_cost=1e-7
+        ),
+    )
+
+    assert breakdown.cache_read_cost == pytest.approx(800 * 1e-7)
+    assert breakdown.cache_creation_cost == pytest.approx(100 * 1e-6)
+    assert breakdown.reasoning_cost == pytest.approx(200 * 2e-6)
+
+
+def test_token_type_cost_breakdown_reconciles_with_custom_pricing_totals():
+    from litellm.cost_calculator import cost_per_token
+    from litellm.types.utils import CostPerToken
+
+    usage = _custom_priced_usage()
+    custom_cost_per_token = CostPerToken(
+        input_cost_per_token=1e-6,
+        output_cost_per_token=2e-6,
+        cache_read_input_token_cost=1e-7,
+        cache_creation_input_token_cost=1.25e-6,
+    )
+
+    prompt_cost, completion_cost = cost_per_token(
+        model="openai/onprem-model",
+        custom_llm_provider="openai",
+        prompt_tokens=1000,
+        completion_tokens=500,
+        usage_object=usage,
+        custom_cost_per_token=custom_cost_per_token,
+    )
+    breakdown = get_token_type_cost_breakdown(
+        model="openai/onprem-model",
+        custom_llm_provider="openai",
+        usage=usage,
+        custom_cost_per_token=custom_cost_per_token,
+    )
+
+    assert 100 * 1e-6 + breakdown.cache_read_cost + breakdown.cache_creation_cost == pytest.approx(prompt_cost)
+    assert 300 * 2e-6 + breakdown.reasoning_cost == pytest.approx(completion_cost)
+
+
+def test_billed_token_rates_follow_the_token_tier_the_breakdown_bills_at(monkeypatch):
+    monkeypatch.setitem(
+        litellm.model_cost,
+        "tiered-cache-model",
+        {
+            "input_cost_per_token": 3e-6,
+            "output_cost_per_token": 15e-6,
+            "cache_read_input_token_cost": 3e-7,
+            "cache_creation_input_token_cost": 3.75e-6,
+            "input_cost_per_token_above_200k_tokens": 6e-6,
+            "output_cost_per_token_above_200k_tokens": 3e-5,
+            "cache_read_input_token_cost_above_200k_tokens": 6e-7,
+            "cache_creation_input_token_cost_above_200k_tokens": 7.5e-6,
+            "litellm_provider": "openai",
+            "mode": "chat",
+        },
+    )
+    usage = Usage(
+        prompt_tokens=250_000,
+        completion_tokens=1_000,
+        total_tokens=251_000,
+        prompt_tokens_details=PromptTokensDetailsWrapper(cached_tokens=200_000, cache_creation_tokens=10_000),
+        completion_tokens_details=CompletionTokensDetailsWrapper(reasoning_tokens=200),
+    )
+
+    rates = get_billed_token_rates(model="tiered-cache-model", custom_llm_provider="openai", usage=usage)
+    breakdown = get_token_type_cost_breakdown(model="tiered-cache-model", custom_llm_provider="openai", usage=usage)
+
+    assert rates == BilledTokenRates(
+        input_cost_per_token=6e-6,
+        output_cost_per_token=3e-5,
+        cache_read_input_token_cost=6e-7,
+        cache_creation_input_token_cost=7.5e-6,
+        cache_creation_input_token_cost_above_1hr=0.0,
+        output_cost_per_reasoning_token=3e-5,
+    )
+    assert breakdown.cache_read_cost == pytest.approx(200_000 * rates.cache_read_input_token_cost)
+    assert breakdown.cache_creation_cost == pytest.approx(10_000 * rates.cache_creation_input_token_cost)
+    assert breakdown.reasoning_cost == pytest.approx(200 * rates.output_cost_per_reasoning_token)
+
+
+def test_a_pinned_billing_time_prices_the_totals_and_the_reported_rates_at_one_moment(monkeypatch):
+    """Totals and reported rates resolve off-peak pricing on separate paths that each read the
+    clock, so a window opening between the two reads used to leave them describing one request
+    at two different prices. Pinned, both must answer for the pinned moment."""
+    monkeypatch.setitem(
+        litellm.model_cost,
+        "off-peak-model",
+        {
+            "input_cost_per_token": 3e-6,
+            "output_cost_per_token": 15e-6,
+            "off_peak_pricing": {
+                "hours_utc": "02:00-03:00",
+                "input_cost_per_token": 1e-6,
+                "output_cost_per_token": 5e-6,
+            },
+            "litellm_provider": "openai",
+            "mode": "chat",
+        },
+    )
+    usage = Usage(prompt_tokens=1000, completion_tokens=500, total_tokens=1500)
+
+    with pinned_billing_time(datetime(2026, 1, 1, 2, 30, tzinfo=timezone.utc)):
+        off_peak_prompt_cost, off_peak_completion_cost = generic_cost_per_token(
+            model="off-peak-model", usage=usage, custom_llm_provider="openai"
+        )
+        off_peak_rates = get_billed_token_rates(model="off-peak-model", custom_llm_provider="openai", usage=usage)
+    with pinned_billing_time(datetime(2026, 1, 1, 12, 30, tzinfo=timezone.utc)):
+        peak_prompt_cost, peak_completion_cost = generic_cost_per_token(
+            model="off-peak-model", usage=usage, custom_llm_provider="openai"
+        )
+        peak_rates = get_billed_token_rates(model="off-peak-model", custom_llm_provider="openai", usage=usage)
+
+    assert off_peak_rates.input_cost_per_token == pytest.approx(1e-6)
+    assert peak_rates.input_cost_per_token == pytest.approx(3e-6)
+    assert off_peak_prompt_cost == pytest.approx(1000 * off_peak_rates.input_cost_per_token)
+    assert off_peak_completion_cost == pytest.approx(500 * off_peak_rates.output_cost_per_token)
+    assert peak_prompt_cost == pytest.approx(1000 * peak_rates.input_cost_per_token)
+    assert peak_completion_cost == pytest.approx(500 * peak_rates.output_cost_per_token)
+
+
+def test_the_token_type_breakdown_carries_the_rates_it_billed_at(monkeypatch):
+    """Callers that report both the lines and the rates read the rates off the breakdown rather than
+    resolving them a second time, so the breakdown has to hand back exactly what it billed at."""
+    monkeypatch.setitem(
+        litellm.model_cost,
+        "xai/tiered-model",
+        {
+            "input_cost_per_token": 3e-6,
+            "output_cost_per_token": 15e-6,
+            "cache_read_input_token_cost": 3e-7,
+            "input_cost_per_token_above_200k_tokens": 6e-6,
+            "output_cost_per_token_above_200k_tokens": 3e-5,
+            "cache_read_input_token_cost_above_200k_tokens": 6e-7,
+            "litellm_provider": "xai",
+            "mode": "chat",
+        },
+    )
+    usage = Usage(
+        prompt_tokens=200_000,
+        completion_tokens=1_000,
+        total_tokens=201_000,
+        prompt_tokens_details=PromptTokensDetailsWrapper(cached_tokens=100_000),
+    )
+
+    breakdown = get_token_type_cost_breakdown(model="xai/tiered-model", custom_llm_provider="xai", usage=usage)
+
+    assert breakdown.rates == get_billed_token_rates(
+        model="xai/tiered-model", custom_llm_provider="xai", usage=usage
+    )
+    assert breakdown.rates.cache_read_input_token_cost == pytest.approx(6e-7)
+    assert breakdown.cache_read_cost == pytest.approx(100_000 * breakdown.rates.cache_read_input_token_cost)
+
+
+def test_the_token_type_breakdown_reports_no_rates_for_an_unpriced_model():
+    usage = Usage(prompt_tokens=10, completion_tokens=5, total_tokens=15)
+
+    breakdown = get_token_type_cost_breakdown(
+        model="no-such-model-anywhere", custom_llm_provider="openai", usage=usage
+    )
+
+    assert breakdown.rates is None
+
+
+def test_billed_token_rates_are_none_for_an_unpriced_model():
+    usage = Usage(prompt_tokens=10, completion_tokens=5, total_tokens=15)
+
+    assert get_billed_token_rates(model="no-such-model-anywhere", custom_llm_provider="openai", usage=usage) is None
+
+
 def test_token_type_cost_breakdown_zero_without_special_tokens(_local_model_cost_map):
 
     usage = Usage(prompt_tokens=100, completion_tokens=50, total_tokens=150)
@@ -3913,9 +4110,7 @@ def test_token_type_cost_breakdown_zero_without_special_tokens(_local_model_cost
         model="gpt-4o", custom_llm_provider="openai", usage=usage
     )
 
-    assert breakdown == TokenTypeCostBreakdown(
-        reasoning_cost=0.0, cache_read_cost=0.0, cache_creation_cost=0.0
-    )
+    assert (breakdown.reasoning_cost, breakdown.cache_read_cost, breakdown.cache_creation_cost) == (0.0, 0.0, 0.0)
 
 
 @pytest.mark.parametrize(
@@ -3987,9 +4182,7 @@ def test_token_type_cost_breakdown_handles_unknown_model_gracefully():
             completion_tokens_details=CompletionTokensDetailsWrapper(reasoning_tokens=5),
         ),
     )
-    assert breakdown == TokenTypeCostBreakdown(
-        reasoning_cost=0.0, cache_read_cost=0.0, cache_creation_cost=0.0
-    )
+    assert (breakdown.reasoning_cost, breakdown.cache_read_cost, breakdown.cache_creation_cost) == (0.0, 0.0, 0.0)
 
 
 def test_token_type_cost_breakdown_applies_regional_uplift(_local_model_cost_map):
diff --git a/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_tool_call_cost_tracking.py b/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_tool_call_cost_tracking.py
index 6cc3dcceebc..bbb7b5f9c35 100644
--- a/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_tool_call_cost_tracking.py
+++ b/tests/test_litellm/litellm_core_utils/llm_cost_calc/test_tool_call_cost_tracking.py
@@ -1,5 +1,6 @@
-import os
+import json
 from collections.abc import Mapping, Sequence
+from pathlib import Path
 
 import pytest
 
@@ -11,8 +12,6 @@ from litellm.types.llms.openai import FileSearchTool, ResponsesAPIResponse, WebS
 from litellm.types.utils import ModelResponse, StandardBuiltInToolsParams
 
 
-
-
 def test_web_search_cost_low():
     web_search_options = WebSearchOptions(search_context_size="low")
     model_info = litellm.get_model_info("gpt-4o-search-preview")
@@ -683,12 +682,13 @@ def test_web_search_provider_prefix_fallback_does_not_misprice_non_gemini_model(
 
 
 def _openai_responses_with_web_search_calls(model, num_calls):
-    from litellm.types.llms.openai import ResponsesAPIResponse
     from openai.types.responses.response_function_web_search import (
         ActionSearch,
         ResponseFunctionWebSearch,
     )
 
+    from litellm.types.llms.openai import ResponsesAPIResponse
+
     output = [
         ResponseFunctionWebSearch(
             id=f"ws_{i}",
@@ -859,11 +859,62 @@ def test_dated_search_preview_entries_carry_search_pricing(local_model_cost_map)
         custom_llm_provider="openai",
         standard_built_in_tools_params=None,
     )
-    assert cost == pytest.approx(0.035), (
-        f"dated search-preview id must bill the $0.035 search fee, got ${cost}"
+    assert cost == pytest.approx(0.025), (
+        f"dated search-preview id must bill the $0.025 search fee, got ${cost}"
     )
 
 
+@pytest.mark.parametrize(
+    "web_search_options",
+    [
+        None,
+        WebSearchOptions(search_context_size="low"),
+        WebSearchOptions(search_context_size="medium"),
+        WebSearchOptions(search_context_size="high"),
+    ],
+)
+def test_gpt_4o_mini_snapshot_bills_web_search_like_its_alias(
+    web_search_options: WebSearchOptions | None, local_model_cost_map: None
+) -> None:
+    alias_info = litellm.get_model_info("gpt-4o-mini")
+    snapshot_info = litellm.get_model_info("gpt-4o-mini-2024-07-18")
+
+    assert not snapshot_info["supports_web_search"]
+    assert not alias_info["supports_web_search"]
+
+    snapshot_cost = StandardBuiltInToolCostTracking.get_cost_for_web_search(
+        web_search_options=web_search_options, model_info=snapshot_info
+    )
+    alias_cost = StandardBuiltInToolCostTracking.get_cost_for_web_search(
+        web_search_options=web_search_options, model_info=alias_info
+    )
+
+    assert snapshot_cost == alias_cost == 0.025
+
+
+def test_gpt_4o_mini_web_search_price_matches_in_both_cost_maps():
+    repo_root = Path(__file__).parents[4]
+    cost_maps = tuple(
+        json.loads((repo_root / path).read_text(encoding="utf-8"))
+        for path in (
+            "model_prices_and_context_window.json",
+            "litellm/model_prices_and_context_window_backup.json",
+        )
+    )
+    canonical, backup = cost_maps
+    expected_search_price = {
+        "search_context_size_low": 0.025,
+        "search_context_size_medium": 0.025,
+        "search_context_size_high": 0.025,
+    }
+    for model_name in ("gpt-4o-mini", "gpt-4o-mini-2024-07-18"):
+        canonical_entry = canonical[model_name]
+        backup_entry = backup[model_name]
+        assert canonical_entry["search_context_cost_per_query"] == expected_search_price
+        assert backup_entry["search_context_cost_per_query"] == expected_search_price
+        assert canonical_entry == backup_entry
+
+
 # Note: File search integration test removed due to complex annotation detection logic
 # The unit tests in test_azure_assistant_cost_tracking.py provide comprehensive coverage
 
diff --git a/tests/test_litellm/litellm_core_utils/llm_response_utils/test_convert_dict_to_response.py b/tests/test_litellm/litellm_core_utils/llm_response_utils/test_convert_dict_to_response.py
index 304d732c518..8e46ae21de6 100644
--- a/tests/test_litellm/litellm_core_utils/llm_response_utils/test_convert_dict_to_response.py
+++ b/tests/test_litellm/litellm_core_utils/llm_response_utils/test_convert_dict_to_response.py
@@ -1,4 +1,6 @@
+from typing import Final
 
+import pytest
 
 from litellm.constants import RESPONSE_FORMAT_TOOL_NAME
 from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response import (
@@ -99,3 +101,97 @@ def test_handle_invalid_parallel_tool_calls_skips_custom_tool_calls():
     )
     result = _handle_invalid_parallel_tool_calls([custom_tool_call, function_tool_call])
     assert result == [custom_tool_call, function_tool_call]
+
+
+def test_convert_empty_choices_response() -> None:
+    from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response import (
+        convert_to_streaming_response,
+    )
+
+    resp: Final = {
+        "id": "x",
+        "created": 1,
+        "model": "gemini-3.5-flash",
+        "object": "chat.completion",
+        "choices": [],
+        "usage": {"prompt_tokens": 10, "completion_tokens": 0, "total_tokens": 10},
+        "vertex_ai_safety_results": ["blocked"],
+    }
+    result: Final = convert_to_model_response_object(
+        response_object=resp,
+        model_response_object=ModelResponse(),
+        response_type="completion",
+    )
+    assert result.choices == []
+    assert getattr(result, "vertex_ai_safety_results") == ["blocked"]
+
+    sync_stream: Final = list(convert_to_streaming_response(response_object=resp))
+    assert len(sync_stream) == 1
+    assert sync_stream[0].choices == []
+
+
+@pytest.mark.asyncio
+async def test_convert_empty_choices_response_async() -> None:
+    from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response import (
+        convert_to_streaming_response_async,
+    )
+
+    resp: Final = {
+        "id": "x",
+        "created": 1,
+        "model": "gemini-3.5-flash",
+        "object": "chat.completion",
+        "choices": [],
+        "usage": {"prompt_tokens": 10, "completion_tokens": 0, "total_tokens": 10},
+    }
+    async_chunks: Final = [chunk async for chunk in convert_to_streaming_response_async(response_object=resp)]
+    assert len(async_chunks) == 1
+    assert async_chunks[0].choices == []
+
+
+def test_convert_missing_choices_raises_api_error() -> None:
+    from litellm.exceptions import APIError
+
+    resp: Final = {
+        "id": "x",
+        "created": 1,
+        "model": "gemini-3.5-flash",
+        "object": "chat.completion",
+    }
+    with pytest.raises(APIError) as exc_info:
+        convert_to_model_response_object(
+            response_object=resp,
+            model_response_object=ModelResponse(),
+            response_type="completion",
+        )
+    assert "no 'choices'" in str(exc_info.value)
+
+
+@pytest.mark.parametrize(("choices", "type_name"), [({}, "dict"), ("", "str"), (None, "NoneType"), (0, "int")])
+@pytest.mark.asyncio
+async def test_convert_non_list_choices_raises_api_error(choices: object, type_name: str) -> None:
+    from litellm.exceptions import APIError
+    from litellm.litellm_core_utils.llm_response_utils.convert_dict_to_response import (
+        convert_to_streaming_response,
+        convert_to_streaming_response_async,
+    )
+
+    resp: Final = {
+        "id": "x",
+        "created": 1,
+        "model": "gemini-3.5-flash",
+        "object": "chat.completion",
+        "choices": choices,
+    }
+    expected: Final = f"'choices' that is not a list \\({type_name}\\)"
+    with pytest.raises(APIError, match=expected):
+        convert_to_model_response_object(
+            response_object=resp,
+            model_response_object=ModelResponse(),
+            response_type="completion",
+        )
+    with pytest.raises(APIError, match=expected):
+        list(convert_to_streaming_response(response_object=resp))
+    with pytest.raises(APIError, match=expected):
+        async for _ in convert_to_streaming_response_async(response_object=resp):
+            pass
diff --git a/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_common_utils.py b/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_common_utils.py
index c037f928593..b5890d1a5b0 100644
--- a/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_common_utils.py
+++ b/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_common_utils.py
@@ -1,23 +1,33 @@
+import copy
 import functools
 import json
 import os
+import sys
+from typing import Final
 from unittest.mock import MagicMock, patch
 
 import pytest
 
-
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    ENCRYPTED_REASONING_SIGNATURE_PREFIX,
     TOOL_RESULT_IMAGE_BOUNDARY,
     TOOL_RESULT_IMAGE_PLACEHOLDER,
     add_system_prompt_to_messages,
+    encrypted_content_from_signature,
+    encrypted_reasoning_signature,
     get_file_ids_from_messages,
     get_format_from_file_id,
     handle_any_messages_to_chat_completion_str_messages_conversion,
     hoist_images_from_tool_messages,
+    is_encrypted_reasoning_block,
+    responses_reasoning_items_from_thinking_blocks,
     split_concatenated_json_objects,
+    strip_encrypted_reasoning_from_messages,
     update_messages_with_model_file_ids,
 )
 
+_ARTIFACT_FIELD_PATTERN: Final = r'^(?!__.*__$)[^\p{Cc}\p{Cf}\p{Zl}\p{Zp}"\\./[\]]{1,200}$'
+
 
 def test_get_format_from_file_id():
     unified_file_id = "litellm_proxy:application/pdf;unified_id,cbbe3534-8bf8-4386-af00-f5f6b7e370bf"
@@ -1435,7 +1445,7 @@ class TestFlattenTopLevelSchemaCombinators:
         assert schema == snapshot
 
 
-class TestToolWithFlattenedParameters:
+class TestToolWithSanitizedParameters:
     def _anyof_tool(self):
         return {
             "type": "function",
@@ -1462,11 +1472,12 @@ class TestToolWithFlattenedParameters:
 
     def test_flattens_anyof_parameters_into_new_tool(self):
         from litellm.litellm_core_utils.prompt_templates.common_utils import (
-            tool_with_flattened_parameters,
+            flatten_combinators_and_drop_non_python_regex_patterns,
+            tool_with_sanitized_parameters,
         )
 
         tool = self._anyof_tool()
-        result = tool_with_flattened_parameters(tool)
+        result = tool_with_sanitized_parameters(tool, flatten_combinators_and_drop_non_python_regex_patterns)
 
         assert result is not tool
         parameters = result["function"]["parameters"]
@@ -1479,7 +1490,8 @@ class TestToolWithFlattenedParameters:
 
     def test_clean_parameters_return_the_same_tool_object(self):
         from litellm.litellm_core_utils.prompt_templates.common_utils import (
-            tool_with_flattened_parameters,
+            flatten_combinators_and_drop_non_python_regex_patterns,
+            tool_with_sanitized_parameters,
         )
 
         tool = {
@@ -1490,7 +1502,23 @@ class TestToolWithFlattenedParameters:
             },
         }
 
-        assert tool_with_flattened_parameters(tool) is tool
+        assert tool_with_sanitized_parameters(tool, flatten_combinators_and_drop_non_python_regex_patterns) is tool
+
+    def test_pattern_only_sanitizer_drops_the_regex_and_keeps_the_union(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+            tool_with_sanitized_parameters,
+        )
+
+        tool = self._anyof_tool()
+        tool["function"]["parameters"]["properties"]["id"]["pattern"] = _ARTIFACT_FIELD_PATTERN
+
+        result = tool_with_sanitized_parameters(tool, drop_non_python_regex_patterns)
+
+        parameters = result["function"]["parameters"]
+        assert parameters["properties"]["id"] == {"type": "string"}
+        assert parameters["anyOf"] == self._anyof_tool()["function"]["parameters"]["anyOf"]
+        assert tool["function"]["parameters"]["properties"]["id"]["pattern"] == _ARTIFACT_FIELD_PATTERN
 
     @pytest.mark.parametrize(
         "tool",
@@ -1503,10 +1531,127 @@ class TestToolWithFlattenedParameters:
     )
     def test_non_dict_function_or_parameters_return_the_same_tool_object(self, tool):
         from litellm.litellm_core_utils.prompt_templates.common_utils import (
-            tool_with_flattened_parameters,
+            flatten_combinators_and_drop_non_python_regex_patterns,
+            tool_with_sanitized_parameters,
         )
 
-        assert tool_with_flattened_parameters(tool) is tool
+        assert tool_with_sanitized_parameters(tool, flatten_combinators_and_drop_non_python_regex_patterns) is tool
+
+
+class TestDropNonPythonRegexPatterns:
+    """Claude Code's Artifact tool declares ECMA-262 ``\\p{..}`` escapes that OpenAI's
+    validator, which compiles ``pattern`` values and ``patternProperties`` keys with
+    Python ``re``, refuses as "not a 'regex'"."""
+
+    def _schema(self, pattern):
+        return {
+            "type": "object",
+            "properties": {
+                "field": {"type": "string", "pattern": pattern},
+                "writes": {
+                    "type": "array",
+                    "items": {"properties": {"doc_id": {"type": "string", "pattern": pattern}}},
+                },
+                "query": {"anyOf": [{"type": "string", "pattern": pattern}, {"type": "null"}]},
+                "pair": {"type": "array", "prefixItems": [{"type": "string", "pattern": pattern}]},
+                "extra": {"type": "object", "additionalProperties": {"type": "string", "pattern": pattern}},
+                "tagged": {
+                    "type": "object",
+                    "patternProperties": {pattern: {"type": "string"}, "^x_": {"type": "integer"}},
+                },
+            },
+            "$defs": {"segment": {"type": "string", "pattern": pattern}},
+            "required": ["field"],
+        }
+
+    def test_drops_every_regex_python_re_rejects_from_every_schema_position(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+        )
+
+        schema = self._schema(_ARTIFACT_FIELD_PATTERN)
+
+        result = drop_non_python_regex_patterns(schema)
+
+        assert '"pattern"' not in json.dumps(result)
+        properties = result["properties"]
+        assert properties["field"] == {"type": "string"}
+        assert properties["writes"]["items"]["properties"]["doc_id"] == {"type": "string"}
+        assert properties["query"]["anyOf"] == [{"type": "string"}, {"type": "null"}]
+        assert properties["pair"]["prefixItems"] == [{"type": "string"}]
+        assert properties["extra"]["additionalProperties"] == {"type": "string"}
+        assert properties["tagged"]["patternProperties"] == {"^x_": {"type": "integer"}}
+        assert result["$defs"]["segment"] == {"type": "string"}
+        assert result["required"] == ["field"]
+        assert schema == self._schema(_ARTIFACT_FIELD_PATTERN)
+
+    def test_keeps_regexes_python_re_compiles_and_returns_the_same_object(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+        )
+
+        schema = self._schema(r'^(?!__.*__$)[^"\\./[\]]{1,200}$')
+
+        assert drop_non_python_regex_patterns(schema) is schema
+
+    def test_pattern_keys_inside_data_positions_are_not_regexes(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+        )
+
+        schema = {
+            "type": "object",
+            "properties": {
+                "pattern": {"type": "string"},
+                "template": {"type": "object", "default": {"pattern": _ARTIFACT_FIELD_PATTERN}},
+                "samples": {"type": "array", "examples": [{"pattern": _ARTIFACT_FIELD_PATTERN}]},
+                "fixed": {"const": {"pattern": _ARTIFACT_FIELD_PATTERN}},
+                "vendor": {"type": "string", "x-litellm": {"pattern": _ARTIFACT_FIELD_PATTERN}},
+            },
+            "required": ["pattern"],
+        }
+
+        assert drop_non_python_regex_patterns(schema) is schema
+
+    def test_regex_nested_past_what_python_re_can_parse_is_dropped_not_raised(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+        )
+
+        schema = {
+            "type": "object",
+            "properties": {"deep": {"type": "string", "pattern": "(" * 2000 + "a" + ")" * 2000}},
+        }
+
+        assert drop_non_python_regex_patterns(schema)["properties"]["deep"] == {"type": "string"}
+
+    def test_walks_schemas_deeper_than_the_interpreter_recursion_limit(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+        )
+
+        depth = sys.getrecursionlimit()
+        leaf = {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN}
+        schema = functools.reduce(
+            lambda inner, _: {"type": "object", "properties": {"child": inner}}, range(depth), leaf
+        )
+
+        result = drop_non_python_regex_patterns(schema)
+
+        assert functools.reduce(lambda node, _: node["properties"]["child"], range(depth), result) == {"type": "string"}
+        assert functools.reduce(lambda node, _: node["properties"]["child"], range(depth), schema) is leaf
+
+    def test_leaves_levels_past_the_json_nesting_limit_alone(self):
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            drop_non_python_regex_patterns,
+        )
+
+        leaf = {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN}
+        schema = functools.reduce(
+            lambda inner, _: {"type": "object", "properties": {"child": inner}}, range(1100), leaf
+        )
+
+        assert drop_non_python_regex_patterns(schema) is schema
 
 
 class TestRequestContainsImageContent:
@@ -1554,3 +1699,117 @@ class TestRequestContainsImageContent:
         for _ in range(50):
             nested = {"type": "tool_result", "content": [nested]}
         assert request_contains_image_content([{"role": "user", "content": [nested]}]) is False
+
+
+class TestEncryptedReasoningReplay:
+    """Regression for https://github.com/BerriAI/litellm/issues/40288."""
+
+    def test_signature_round_trips_the_encrypted_content(self):
+        assert encrypted_content_from_signature(encrypted_reasoning_signature("gAAAA_bytes")) == "gAAAA_bytes"
+
+    @pytest.mark.parametrize(
+        "signature", [None, "", "ErcBCkgIValidAnthropicSignature", "litellm_encrypted_reasoning:", 7]
+    )
+    def test_anything_else_is_not_encrypted_content(self, signature):
+        assert encrypted_content_from_signature(signature) is None
+
+    def test_encrypted_thinking_block_replays_its_own_item(self):
+        items = responses_reasoning_items_from_thinking_blocks(
+            [{"type": "thinking", "thinking": "Plan.", "signature": encrypted_reasoning_signature("gAAAA_1")}]
+        )
+        assert items == (
+            {
+                "type": "reasoning",
+                "summary": [{"type": "summary_text", "text": "Plan."}],
+                "encrypted_content": "gAAAA_1",
+            },
+        )
+
+    def test_encrypted_redacted_block_replays_with_an_empty_summary(self):
+        items = responses_reasoning_items_from_thinking_blocks(
+            [{"type": "redacted_thinking", "data": encrypted_reasoning_signature("gAAAA_1")}]
+        )
+        assert items == ({"type": "reasoning", "summary": [], "encrypted_content": "gAAAA_1"},)
+
+    def test_plain_blocks_collapse_into_one_summary_item_around_encrypted_ones(self):
+        items = responses_reasoning_items_from_thinking_blocks(
+            [
+                {"type": "thinking", "thinking": "A.", "signature": None},
+                {"type": "thinking", "thinking": "B.", "signature": ""},
+                {"type": "thinking", "thinking": "C.", "signature": encrypted_reasoning_signature("gAAAA_c")},
+                {"type": "redacted_thinking", "data": "anthropic-minted-opaque-data"},
+                {"type": "thinking", "thinking": "D."},
+            ]
+        )
+        assert items == (
+            {
+                "type": "reasoning",
+                "summary": [{"type": "summary_text", "text": "A."}, {"type": "summary_text", "text": "B."}],
+            },
+            {"type": "reasoning", "summary": [{"type": "summary_text", "text": "C."}], "encrypted_content": "gAAAA_c"},
+            {"type": "reasoning", "summary": [{"type": "summary_text", "text": "D."}]},
+        )
+        assert all("id" not in item for item in items)
+
+    def test_blocks_without_text_or_encrypted_content_produce_nothing(self):
+        assert responses_reasoning_items_from_thinking_blocks([{"type": "thinking", "thinking": ""}]) == ()
+        assert responses_reasoning_items_from_thinking_blocks([]) == ()
+
+    @pytest.mark.parametrize(
+        ("block", "expected"),
+        [
+            ({"type": "thinking", "thinking": "x", "signature": encrypted_reasoning_signature("g")}, True),
+            ({"type": "redacted_thinking", "data": encrypted_reasoning_signature("g")}, True),
+            ({"type": "thinking", "thinking": "x", "signature": ENCRYPTED_REASONING_SIGNATURE_PREFIX}, True),
+            ({"type": "redacted_thinking", "data": ENCRYPTED_REASONING_SIGNATURE_PREFIX}, True),
+            ({"type": "thinking", "thinking": "x", "signature": "ErcBCkgIValid"}, False),
+            ({"type": "redacted_thinking", "data": "EmwKAhgBEgy"}, False),
+            ({"type": "text", "text": encrypted_reasoning_signature("g")}, False),
+            ("not a block", False),
+        ],
+    )
+    def test_is_encrypted_reasoning_block(self, block, expected):
+        assert is_encrypted_reasoning_block(block) is expected
+
+    def test_strip_drops_every_bridge_tagged_block_and_leaves_no_unsigned_thinking_behind(self):
+        assistant_content = [
+            {"type": "thinking", "thinking": "minted by Anthropic", "signature": "ErcBCkgIValid"},
+            {"type": "thinking", "thinking": "packed by the bridge", "signature": encrypted_reasoning_signature("g1")},
+            {"type": "redacted_thinking", "data": encrypted_reasoning_signature("g2")},
+            {"type": "thinking", "thinking": "", "signature": encrypted_reasoning_signature("g3")},
+            {"type": "text", "text": "answer"},
+        ]
+        messages = [
+            {"role": "user", "content": "question"},
+            {"role": "assistant", "content": assistant_content},
+            {"role": "user", "content": [{"type": "text", "text": "follow-up"}]},
+        ]
+
+        strip_encrypted_reasoning_from_messages(messages)
+
+        assert messages[1]["content"] is assistant_content
+        assert assistant_content == [
+            {"type": "thinking", "thinking": "minted by Anthropic", "signature": "ErcBCkgIValid"},
+            {"type": "text", "text": "answer"},
+        ]
+        assert all(block["signature"] for block in assistant_content if block["type"] == "thinking")
+        assert messages[0] == {"role": "user", "content": "question"}
+        assert messages[2] == {"role": "user", "content": [{"type": "text", "text": "follow-up"}]}
+
+    @pytest.mark.parametrize(
+        "messages",
+        [
+            "not a list",
+            None,
+            [{"role": "user", "content": None}],
+            [{"role": "user", "content": "plain string"}],
+            ["not a message"],
+            [{"role": "assistant", "content": [{"type": "thinking", "thinking": "x", "signature": "ErcBCkgIValid"}]}],
+        ],
+    )
+    def test_strip_leaves_history_without_bridge_reasoning_untouched(self, messages):
+        before = copy.deepcopy(messages)
+
+        strip_encrypted_reasoning_from_messages(messages)
+
+        assert messages == before
diff --git a/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_factory.py b/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_factory.py
index dd2d45f00c6..66d10fd1407 100644
--- a/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_factory.py
+++ b/tests/test_litellm/litellm_core_utils/prompt_templates/test_litellm_core_utils_prompt_templates_factory.py
@@ -191,8 +191,16 @@ def test_bedrock_converse_assistant_with_empty_thinking_block_and_tool_calls():
         {"type": "thinking", "thinking": "oss reasoning", "signature": None},
         {"type": "thinking", "thinking": "oss reasoning", "signature": ""},
         {"type": "thinking", "thinking": "oss reasoning"},
+        {"type": "thinking", "thinking": "openai reasoning", "signature": "litellm_encrypted_reasoning:gAAAA"},
+        {"type": "redacted_thinking", "data": "litellm_encrypted_reasoning:gAAAA"},
+    ],
+    ids=[
+        "null_signature",
+        "empty_signature",
+        "missing_signature",
+        "encrypted_reasoning_signature",
+        "encrypted_reasoning_redacted_data",
     ],
-    ids=["null_signature", "empty_signature", "missing_signature"],
 )
 def test_anthropic_messages_pt_drops_unsignable_thinking_block(thinking_block):
     """Open-source reasoning models (DeepSeek-R1, Qwen, etc.) emit thinking blocks
@@ -219,7 +227,7 @@ def test_anthropic_messages_pt_drops_unsignable_thinking_block(thinking_block):
     assistant = next(m for m in result if m["role"] == "assistant")
     content = assistant["content"]
     assert all(
-        block.get("type") != "thinking" for block in content
+        block.get("type") not in ("thinking", "redacted_thinking") for block in content
     ), f"unsignable thinking block must be dropped, got {content!r}"
     assert any(
         block.get("type") == "text" and block.get("text") == "2+2 equals 4."
diff --git a/tests/test_litellm/litellm_core_utils/test_classifier_logging.py b/tests/test_litellm/litellm_core_utils/test_classifier_logging.py
new file mode 100644
index 00000000000..ccf14ff06c7
--- /dev/null
+++ b/tests/test_litellm/litellm_core_utils/test_classifier_logging.py
@@ -0,0 +1,51 @@
+from typing import Final
+
+import pytest
+
+from litellm.litellm_core_utils.classifier_logging import classifier_input_snapshot, masked_originating_request
+
+
+@pytest.mark.parametrize("encoded", [False, True])
+def test_classifier_snapshot_preserves_provider_shape_and_is_independent(encoded: bool) -> None:
+    import json
+
+    provider_body: Final = {"system": [{"text": "rubric"}], "messages": [{"role": "user", "content": "ask"}]}
+    snapshot: Final = classifier_input_snapshot(json.dumps(provider_body) if encoded else provider_body)
+    assert snapshot == provider_body
+    provider_body["messages"][0]["content"] = "later mutation"
+    assert snapshot == {"system": [{"text": "rubric"}], "messages": [{"role": "user", "content": "ask"}]}
+
+
+def test_originating_snapshot_masks_nested_credentials_without_altering_source() -> None:
+    body: Final = {
+        "model": "router",
+        "input": [{"type": "message", "role": "user", "content": "source-only"}],
+        "api_key": "short",
+        "metadata": {"nested": [{"Authorization": "Bearer secret", "access_token": 123}]},
+    }
+    snapshot: Final = masked_originating_request({"proxy_server_request": {"body": body}})
+    assert snapshot is not None
+    assert snapshot["model"] == "router"
+    assert snapshot["input"] == body["input"]
+    assert snapshot["api_key"] == "REDACTED"
+    assert snapshot["metadata"] == {"nested": [{"Authorization": "REDACTED", "access_token": "REDACTED"}]}
+    assert body["api_key"] == "short"
+    assert body["metadata"]["nested"][0]["Authorization"] == "Bearer secret"
+
+
+@pytest.mark.parametrize("header", ["Cookie", "cookie", "COOKIE", "sEt-CoOkIe"])
+def test_originating_snapshot_redacts_cookie_headers_shared_with_caller_metadata(header: str) -> None:
+    headers: Final = {header: "session=synthetic-session-credential", "content-type": "application/json"}
+    body: Final = {"messages": [{"role": "user", "content": "hello"}], "metadata": {"headers": headers}}
+    snapshot: Final = masked_originating_request({"proxy_server_request": {"body": body, "headers": headers}})
+    assert snapshot == {
+        "messages": [{"role": "user", "content": "hello"}],
+        "metadata": {"headers": {header: "REDACTED", "content-type": "application/json"}},
+    }
+    assert headers[header] == "session=synthetic-session-credential"
+    assert body["metadata"]["headers"][header] == "session=synthetic-session-credential"
+
+
+@pytest.mark.parametrize("value", [None, "not-json", [], {"messages": object()}])
+def test_invalid_provider_payload_is_not_reported_as_captured(value: object) -> None:
+    assert classifier_input_snapshot(value) is None
diff --git a/tests/test_litellm/litellm_core_utils/test_fallback_generalizations.py b/tests/test_litellm/litellm_core_utils/test_fallback_generalizations.py
index b1e8163b91d..b0220a36054 100644
--- a/tests/test_litellm/litellm_core_utils/test_fallback_generalizations.py
+++ b/tests/test_litellm/litellm_core_utils/test_fallback_generalizations.py
@@ -571,3 +571,109 @@ def test_shipped_mid_conversation_gate_on_bedrock_ids(shipped_cost_map):
     ):
         matched = match_capability_generalizations(unflagged)
         assert matched is None or not matched.get("supports_mid_conversation_system"), unflagged
+
+
+def test_shipped_rules_flag_unmapped_wandb_ids_as_reasoning(shipped_cost_map):
+    """W&B ships reasoning models faster than the registry names them, so an unmapped
+    wandb id resolves as reasoning-capable and its reasoning_effort survives instead of
+    being dropped. The rule carries no mode and no pricing, so cost stays on the standard
+    unpriced behavior and the deployment does not read as catalog-mapped."""
+    model = "wandb/zai-org/GLM-6-Turbo"
+    assert model not in litellm.model_cost
+
+    info = litellm.get_model_info(model, custom_llm_provider="wandb")
+    assert info["litellm_provider"] == "wandb"
+    assert info["supports_reasoning"] is True
+    assert info.get("mode") is None
+    assert not info.get("input_cost_per_token")
+    assert not info.get("output_cost_per_token")
+
+    assert litellm.supports_reasoning(model="zai-org/GLM-6-Turbo", custom_llm_provider="wandb") is True
+
+
+def test_shipped_wandb_rule_loses_to_mapped_non_reasoning_entries(shipped_cost_map):
+    """The whole point of a fallback is that it only fills gaps. A wandb model the map
+    describes as non-reasoning must stay non-reasoning, otherwise the rule silently
+    re-introduces the blanket supports_reasoning it exists to avoid."""
+    for model in (
+        "meta-llama/Llama-3.1-8B-Instruct",
+        "microsoft/Phi-4-mini-instruct",
+        "moonshotai/Kimi-K2-Instruct",
+        "Qwen/Qwen3-Coder-480B-A35B-Instruct",
+    ):
+        assert f"wandb/{model}" in litellm.model_cost, model
+        assert litellm.supports_reasoning(model=model, custom_llm_provider="wandb") is False, model
+
+
+def test_shipped_wandb_rule_is_anchored_to_the_wandb_namespace(shipped_cost_map):
+    """``^wandb/`` is anchored, so it cannot leak onto another provider's ids."""
+    assert match_capability_generalizations("wandb/some-new-model") == {"supports_reasoning": True}
+    for foreign in ("openai/some-new-model", "notwandb/some-new-model", "together_ai/wandb/some-new-model"):
+        matched = match_capability_generalizations(foreign)
+        assert matched is None or not matched.get("supports_reasoning"), foreign
+
+
+def test_shipped_wandb_rule_keeps_reasoning_effort_on_an_unmapped_model(shipped_cost_map):
+    """End to end through the provider config: the gate WandbConfig applies reads the
+    rule, so reasoning_effort is advertised and survives get_optional_params rather than
+    raising UnsupportedParamsError."""
+    model = "zai-org/GLM-6-Turbo"
+    assert f"wandb/{model}" not in litellm.model_cost
+
+    supported = litellm.get_supported_openai_params(model=f"wandb/{model}")
+    assert supported is not None
+    assert "reasoning_effort" in supported
+
+    optional_params = litellm.utils.get_optional_params(
+        model=model,
+        custom_llm_provider="wandb",
+        reasoning_effort="medium",
+        drop_params=False,
+    )
+    assert optional_params["reasoning_effort"] == "medium"
+
+
+def test_router_registration_does_not_shadow_shipped_rules(shipped_cost_map):
+    """Regression: Router writes every configured deployment into ``litellm.model_cost``,
+    and an exact entry ends the lookup ladder before the rules are consulted. Registering
+    an unmapped model has to carry the rule defaults forward, or configuring a model on a
+    proxy silently strips the capabilities the same model resolves to off-proxy."""
+    from litellm import Router
+
+    unmapped_wandb = "wandb/zai-org/GLM-6-Turbo"
+    unmapped_claude = "anthropic/claude-opus-9"
+    assert unmapped_wandb not in litellm.model_cost
+    assert unmapped_claude not in litellm.model_cost
+
+    Router(
+        model_list=[
+            {"model_name": name, "litellm_params": {"model": name, "api_key": "fake"}}
+            for name in (unmapped_wandb, unmapped_claude)
+        ]
+    )
+
+    assert unmapped_wandb in litellm.model_cost
+    assert unmapped_claude in litellm.model_cost
+    assert litellm.supports_reasoning(model="zai-org/GLM-6-Turbo", custom_llm_provider="wandb") is True
+    assert litellm.supports_reasoning(model="claude-opus-9", custom_llm_provider="anthropic") is True
+
+
+def test_deployment_model_info_beats_the_seeded_rule_defaults(shipped_cost_map):
+    """Seeding a registration from the rules is a floor, not an override: an explicit
+    model_info on the deployment still wins, so a non-reasoning model can be configured
+    under a reasoning-first namespace."""
+    from litellm import Router
+
+    model = "wandb/some-org/NoThink-1"
+    Router(
+        model_list=[
+            {
+                "model_name": model,
+                "litellm_params": {"model": model, "api_key": "fake"},
+                "model_info": {"supports_reasoning": False},
+            }
+        ]
+    )
+
+    assert litellm.model_cost[model]["supports_reasoning"] is False
+    assert litellm.supports_reasoning(model="some-org/NoThink-1", custom_llm_provider="wandb") is False
diff --git a/tests/test_litellm/litellm_core_utils/test_get_model_cost_map.py b/tests/test_litellm/litellm_core_utils/test_get_model_cost_map.py
index 0495440c51c..c509c8399c9 100644
--- a/tests/test_litellm/litellm_core_utils/test_get_model_cost_map.py
+++ b/tests/test_litellm/litellm_core_utils/test_get_model_cost_map.py
@@ -6,6 +6,8 @@ count actual model entries, not reserved meta keys) and the extraction of the
 
 import json
 import os
+import sys
+import threading
 
 import pytest
 
@@ -26,9 +28,7 @@ from litellm.litellm_core_utils.get_model_cost_map import (
 
 
 def _load_root_cost_map() -> dict:
-    path = os.path.join(
-        os.path.dirname(__file__), "../../../model_prices_and_context_window.json"
-    )
+    path = os.path.join(os.path.dirname(__file__), "../../../model_prices_and_context_window.json")
     with open(path) as f:
         return json.load(f)
 
@@ -44,9 +44,7 @@ def test_git_blob_id_is_what_git_hash_object_prints():
 
 
 def _make_models(n: int) -> dict:
-    return {
-        f"model-{i}": {"litellm_provider": "openai", "mode": "chat"} for i in range(n)
-    }
+    return {f"model-{i}": {"litellm_provider": "openai", "mode": "chat"} for i in range(n)}
 
 
 def test_count_model_entries_excludes_reserved_keys():
@@ -129,9 +127,7 @@ def test_finalize_pops_key_and_installs_rules():
 def test_finalize_with_no_block_clears_rules():
     previous = list(get_fallback_generalization_rules())
     try:
-        set_fallback_generalizations(
-            [{"name": "stale", "pattern": r"^x", "model_info": {"a": 1}}]
-        )
+        set_fallback_generalizations([{"name": "stale", "pattern": r"^x", "model_info": {"a": 1}}])
         _finalize_model_cost_map(_make_models(2))
         assert match_capability_generalizations("x-1") is None
     finally:
@@ -317,9 +313,7 @@ def test_get_model_cost_map_stamps_loaded_at():
 
     from litellm.litellm_core_utils import get_model_cost_map as module
 
-    client, _calls = _mock_client(
-        [httpx.Response(200, content=_real_map_bytes())], client_cls=httpx.Client
-    )
+    client, _calls = _mock_client([httpx.Response(200, content=_real_map_bytes())], client_cls=httpx.Client)
 
     before = datetime.now(timezone.utc)
     module.get_model_cost_map(url="https://example.invalid/cost_map.json", client=client)
@@ -328,6 +322,7 @@ def test_get_model_cost_map_stamps_loaded_at():
     assert loaded_at is not None
     assert before <= loaded_at <= datetime.now(timezone.utc)
 
+
 # ---------------------------------------------------------------------------
 # refetch_model_cost_map: retry/backoff behavior for runtime reloads
 # ---------------------------------------------------------------------------
@@ -394,9 +389,7 @@ async def test_refetch_retries_429_honoring_retry_after():
         ]
     )
     sleeper = _SleepRecorder()
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=sleeper, rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloaded)
     assert len(result.model_cost_map) > 100
     assert calls["count"] == 3
@@ -408,9 +401,7 @@ async def test_refetch_gives_up_after_max_attempts_with_exponential_backoff():
     """All 429 without Retry-After: exponential backoff waits, then a failure value."""
     client, calls = _mock_client([httpx.Response(429)])
     sleeper = _SleepRecorder()
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=sleeper, rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloadUnavailable)
     assert "429" in result.reason
     assert "after 3 attempts" in result.reason
@@ -430,9 +421,7 @@ async def test_refetch_caps_retry_after_wait():
         ]
     )
     sleeper = _SleepRecorder()
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=sleeper, rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloaded)
     assert sleeper.waits == [30.0]
 
@@ -447,9 +436,7 @@ async def test_refetch_retries_transport_errors():
         ]
     )
     sleeper = _SleepRecorder()
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=sleeper, rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloaded)
     assert calls["count"] == 2
     assert len(sleeper.waits) == 1
@@ -460,9 +447,7 @@ async def test_refetch_non_retryable_status_fails_immediately():
     """A 404 is permanent: one attempt, no sleeps, failure value."""
     client, calls = _mock_client([httpx.Response(404)])
     sleeper = _SleepRecorder()
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=sleeper, rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloadUnavailable)
     assert "404" in result.reason
     assert calls["count"] == 1
@@ -473,9 +458,7 @@ async def test_refetch_non_retryable_status_fails_immediately():
 async def test_refetch_invalid_json_fails_immediately():
     client, calls = _mock_client([httpx.Response(200, content=b"not json")])
     sleeper = _SleepRecorder()
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=sleeper, rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloadUnavailable)
     assert "invalid JSON" in result.reason
     assert calls["count"] == 1
@@ -487,9 +470,7 @@ async def test_refetch_shrunk_map_fails_integrity_not_swapped_in():
     """A drastically shrunk upstream file is rejected instead of being adopted."""
     tiny = json.dumps(_make_models(60)).encode()
     client, _calls = _mock_client([httpx.Response(200, content=tiny)])
-    result = await refetch_model_cost_map(
-        url=_URL, sleep=_SleepRecorder(), rng=random.Random(0), client=client
-    )
+    result = await refetch_model_cost_map(url=_URL, sleep=_SleepRecorder(), rng=random.Random(0), client=client)
     assert isinstance(result, ModelCostMapReloadUnavailable)
     assert "integrity validation" in result.reason
 
@@ -586,69 +567,125 @@ from litellm.litellm_core_utils.get_model_cost_map import (
 class _SyncSleepRecorder:
     """Injected in place of time.sleep so the boot path's waits are asserted without delay."""
 
-    def __init__(self):
+    def __init__(self, block=False):
         self.waits = []
+        self.block = block
+        self.started = threading.Event()
+        self.release = threading.Event()
 
     def __call__(self, seconds: float) -> None:
+        if self.block:
+            self.started.set()
+            self.release.wait(timeout=10)
         self.waits.append(seconds)
 
 
-def test_boot_load_retries_transient_failures_instead_of_falling_back():
-    """A refused connection then a 503 at pod boot used to pin the process to the bundled
-    backup for its lifetime; both are transient and must be retried before giving up."""
+def _retry_threads():
+    return [thread for thread in threading.enumerate() if thread.name == "litellm-model-cost-map-retry"]
+
+
+def test_boot_load_success_does_not_start_background_retry():
+    client, calls = _mock_client([httpx.Response(200, content=_real_map_bytes())], client_cls=httpx.Client)
+    sleeper = _SyncSleepRecorder()
+
+    cost_map = get_model_cost_map(
+        url=_URL,
+        sleep=sleeper,
+        rng=random.Random(0),
+        client=client,
+    )
+    assert calls["count"] == 1
+    assert sleeper.waits == []
+    assert _retry_threads() == []
+    assert cost_map.keys() >= _load_root_cost_map().keys() - {"sample_spec", FALLBACK_GENERALIZATIONS_KEY}
+    assert get_model_cost_map_source_info()["source"] == "remote"
+
+
+def test_boot_load_transient_failure_returns_local_then_background_retry_adopts_remote(monkeypatch):
+    import litellm
+    from litellm import utils as litellm_utils
+    from litellm.litellm_core_utils import get_model_cost_map as module
+
+    original_model_cost = litellm.model_cost
+    monkeypatch.setattr(litellm, "model_cost", dict(original_model_cost))
+    for name, provider_models in tuple(vars(litellm).items()):
+        if name.endswith("_models") and isinstance(provider_models, set):
+            monkeypatch.setattr(litellm, name, set(provider_models))
+    monkeypatch.setattr(litellm, "models_by_provider", dict(litellm.models_by_provider))
+    monkeypatch.setattr(
+        litellm_utils,
+        "_runtime_registered_model_cost",
+        dict(litellm_utils._runtime_registered_model_cost),
+    )
+    source_info = module._cost_map_source_info
+    for name in ("source", "url", "is_env_forced", "fallback_reason", "loaded_at", "source_revision", "etag"):
+        monkeypatch.setattr(source_info, name, getattr(source_info, name))
+
+    remote_map = _load_root_cost_map()
+    remote_map["claude-remote-only-test"] = {"litellm_provider": "anthropic", "mode": "chat"}
     client, calls = _mock_client(
         [
             httpx.ConnectError("connection refused"),
-            httpx.Response(503),
-            httpx.Response(200, content=_real_map_bytes()),
+            httpx.Response(200, content=json.dumps(remote_map).encode()),
         ],
         client_cls=httpx.Client,
     )
-    sleeper = _SyncSleepRecorder()
+    sleeper = _SyncSleepRecorder(block=True)
+    litellm.register_model({"my-runtime-model": {"litellm_provider": "custom", "max_input_tokens": 4321}})
 
-    cost_map = get_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
-
-    assert calls["count"] == 3
-    assert len(sleeper.waits) == 2
-    assert 2.0 <= sleeper.waits[0] < 3.0
-    assert 4.0 <= sleeper.waits[1] < 5.0
-    source = get_model_cost_map_source_info()
-    assert source["source"] == "remote"
-    assert source["fallback_reason"] is None
-    assert cost_map.keys() >= _load_root_cost_map().keys() - {"sample_spec", FALLBACK_GENERALIZATIONS_KEY}
-
-
-def test_boot_load_honors_retry_after_then_falls_back_after_max_attempts():
-    """An outage longer than the retry budget still ends on the bundled backup, and the
-    recorded fallback reason says how many attempts were spent so operators can tell."""
-    client, calls = _mock_client(
-        [httpx.Response(429, headers={"Retry-After": "7"})], client_cls=httpx.Client
+    cost_map = get_model_cost_map(
+        url=_URL,
+        max_attempts=3,
+        sleep=sleeper,
+        rng=random.Random(0),
+        client=client,
     )
-    sleeper = _SyncSleepRecorder()
 
-    cost_map = get_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
-
-    assert calls["count"] == 3
-    assert sleeper.waits == [7.0, 7.0]
-    source = get_model_cost_map_source_info()
-    assert source["source"] == "local"
-    assert "after 3 attempts" in source["fallback_reason"]
-    assert len(cost_map) > 100
+    assert calls["count"] == 1
+    assert sleeper.waits == []
+    assert sleeper.started.wait(timeout=10)
+    threads = _retry_threads()
+    try:
+        assert len(threads) == 1
+        assert "claude-remote-only-test" not in cost_map
+        assert cost_map.keys() == _finalize_model_cost_map(GetModelCostMap.load_local_model_cost_map()).keys()
+        source = get_model_cost_map_source_info()
+        assert source["source"] == "local"
+        assert source["fallback_reason"].startswith("Remote fetch failed:")
+        sleeper.release.set()
+        for thread in threads:
+            thread.join(timeout=10)
+        assert all(not thread.is_alive() for thread in threads)
+        assert sleeper.waits and 2.0 <= sleeper.waits[0] < 3.0
+        assert calls["count"] == 2
+        assert "claude-remote-only-test" in litellm.model_cost
+        assert "claude-remote-only-test" in litellm.anthropic_models
+        assert "my-runtime-model" in litellm.model_cost
+        source = get_model_cost_map_source_info()
+        assert source["source"] == "remote"
+        assert source["fallback_reason"] is None
+    finally:
+        sleeper.release.set()
+        for thread in _retry_threads():
+            thread.join(timeout=10)
 
 
-def test_boot_load_does_not_retry_permanent_failures():
-    """A 404 or a malformed URL cannot heal by waiting: one attempt, no sleeps, backup."""
+def test_boot_load_does_not_retry_non_retryable_failure():
     client, calls = _mock_client([httpx.Response(404)], client_cls=httpx.Client)
     sleeper = _SyncSleepRecorder()
 
-    get_model_cost_map(url=_URL, sleep=sleeper, rng=random.Random(0), client=client)
+    get_model_cost_map(
+        url=_URL,
+        sleep=sleeper,
+        rng=random.Random(0),
+        client=client,
+    )
     assert calls["count"] == 1
     assert sleeper.waits == []
-    assert get_model_cost_map_source_info()["source"] == "local"
-
-    get_model_cost_map(url="not a url", sleep=sleeper, rng=random.Random(0))
-    assert sleeper.waits == []
-    assert get_model_cost_map_source_info()["source"] == "local"
+    assert _retry_threads() == []
+    source = get_model_cost_map_source_info()
+    assert source["source"] == "local"
+    assert source["fallback_reason"] is not None
 
 
 def test_boot_load_respects_local_env_override(monkeypatch):
@@ -701,7 +738,9 @@ def test_boot_load_that_fails_the_integrity_check_reports_the_backup_not_the_rej
     )
     get_model_cost_map(url=_URL, sleep=_SyncSleepRecorder(), rng=random.Random(0), client=remote)
     shrunk_body = b'{"gpt-5.4-mini": {"mode": "chat", "input_cost_per_token": 1e-06, "output_cost_per_token": 2e-06}}'
-    shrunk, _ = _mock_client([httpx.Response(200, headers={"ETag": 'W/"shrunk"'}, content=shrunk_body)], client_cls=httpx.Client)
+    shrunk, _ = _mock_client(
+        [httpx.Response(200, headers={"ETag": 'W/"shrunk"'}, content=shrunk_body)], client_cls=httpx.Client
+    )
 
     get_model_cost_map(url=_URL, sleep=_SyncSleepRecorder(), rng=random.Random(0), client=shrunk)
 
@@ -711,3 +750,29 @@ def test_boot_load_that_fails_the_integrity_check_reports_the_backup_not_the_rej
     assert source["etag"] is None
     assert source["source_revision"] == _bundled_blob_id()
     assert source["source_revision"] != git_blob_id(shrunk_body)
+
+
+@pytest.mark.parametrize(
+    ("argv0", "request_count"),
+    [
+        ("/some/venv/bin/lite", 0),
+        ("/some/venv/bin/lite.exe", 0),
+        ("/some/venv/bin/python", 1),
+    ],
+)
+def test_boot_load_skips_remote_fetch_for_cli_processes(
+    monkeypatch: pytest.MonkeyPatch, argv0: str, request_count: int
+) -> None:
+    monkeypatch.setattr(sys, "argv", [argv0, "--version"])
+    monkeypatch.delenv("LITELLM_LOCAL_MODEL_COST_MAP", raising=False)
+    client, calls = _mock_client([httpx.Response(200, content=_real_map_bytes())], client_cls=httpx.Client)
+
+    cost_map = get_model_cost_map(url=_URL, client=client)
+
+    assert calls["count"] == request_count
+    assert cost_map
+    source = get_model_cost_map_source_info()
+    if request_count == 0:
+        assert source["source"] == "local"
+    else:
+        assert source["source"] == "remote"
diff --git a/tests/test_litellm/litellm_core_utils/test_litellm_logging.py b/tests/test_litellm/litellm_core_utils/test_litellm_logging.py
index 6aa77745e3d..2f6339dcdbb 100644
--- a/tests/test_litellm/litellm_core_utils/test_litellm_logging.py
+++ b/tests/test_litellm/litellm_core_utils/test_litellm_logging.py
@@ -3,7 +3,8 @@ import contextlib
 import datetime
 import os
 import sys
-from typing import Literal
+from collections.abc import Callable
+from typing import Final, Literal
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -6801,3 +6802,205 @@ def test_get_error_information_redacts_provider_key_from_upstream_url():
     assert "REDACTED" in result["traceback"]
     assert "REDACTED" in result["error_message"]
     assert result["error_code"] == "400"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("provider", ["openai", "azure", "anthropic", "bedrock", "responses"])
+async def test_classifier_audit_matches_provider_transport(provider: str) -> None:
+    import json
+
+    from openai import AsyncAzureOpenAI, AsyncOpenAI
+
+    from litellm.litellm_core_utils.classifier_logging import classifier_input_snapshot
+    from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
+
+    outbound: Final = asyncio.Queue()
+    logs: Final = asyncio.Queue()
+
+    def respond(request: httpx.Request) -> httpx.Response:
+        outbound.put_nowait(json.loads(request.content))
+        content: Final = '{"tier":"SIMPLE"}'
+        if provider == "responses":
+            from litellm.responses.main import mock_responses_api_response
+
+            return httpx.Response(200, json=mock_responses_api_response(content).model_dump())
+        if provider == "anthropic":
+            return httpx.Response(200, json={
+                "id": "msg-audit", "type": "message", "role": "assistant", "model": "claude-haiku-4-5",
+                "content": [{"type": "text", "text": content}], "stop_reason": "end_turn",
+                "usage": {"input_tokens": 10, "output_tokens": 5},
+            })
+        if provider == "bedrock":
+            return httpx.Response(200, json={
+                "output": {"message": {"role": "assistant", "content": [{"text": content}]}},
+                "stopReason": "end_turn", "usage": {"inputTokens": 10, "outputTokens": 5, "totalTokens": 15},
+                "metrics": {"latencyMs": 1},
+            })
+        return httpx.Response(200, json={
+            "id": "chatcmpl-audit", "object": "chat.completion", "created": 0, "model": "gpt-5.6",
+            "choices": [{"index": 0, "message": {"role": "assistant", "content": content}, "finish_reason": "stop"}],
+            "usage": {"prompt_tokens": 10, "completion_tokens": 5, "total_tokens": 15},
+        })
+
+    async def capture(kwargs, response_obj, start_time, end_time):
+        logs.put_nowait(kwargs["standard_logging_object"])
+
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as http_client:
+        handler: Final = AsyncHTTPHandler()
+        await handler.close()
+        handler.client = http_client
+        client: Final = (
+            AsyncAzureOpenAI(
+                api_key="transport-only", azure_endpoint="https://azure.invalid",
+                api_version="2025-04-01-preview", http_client=http_client,
+            )
+            if provider == "azure" else AsyncOpenAI(api_key="transport-only", http_client=http_client)
+            if provider == "openai" else handler
+        )
+        model: Final = {
+            "openai": "openai/gpt-5.6",
+            "azure": "azure/gpt-5.6",
+            "anthropic": "anthropic/claude-haiku-4-5",
+            "bedrock": "bedrock/anthropic.claude-haiku-4-5-20251001-v1:0",
+            "responses": "openai/gpt-5.6",
+        }[provider]
+
+        async def run(marker: str) -> None:
+            if provider == "responses":
+                await litellm.aresponses(
+                    model=model, api_key="transport-only", client=client, max_output_tokens=128,
+                    instructions="classifier-rubric", input=marker,
+                    metadata={"internal_call_origin": "autorouter_classifier"},
+                    proxy_server_request={"body": {}, "originating_request_masked": {"input": f"source-only-{marker}"}},
+                    success_callback=[capture], num_retries=0,
+                )
+                return
+            await litellm.acompletion(
+                model=model, api_key="transport-only", client=client, max_tokens=128,
+                aws_access_key_id="transport-only", aws_secret_access_key="transport-only", aws_region_name="us-east-1",
+                messages=[{"role": "system", "content": "classifier-rubric"}, {"role": "user", "content": marker}],
+                metadata={"internal_call_origin": "autorouter_classifier"},
+                proxy_server_request={"body": {}, "originating_request_masked": {"input": f"source-only-{marker}"}},
+                success_callback=[capture], num_retries=0,
+                **({"api_base": "https://azure.invalid", "api_version": "2025-04-01-preview"} if provider == "azure" else {}),
+                **({"extra_body": {"audit_context": "provider-extra"}, "extra_headers": {"X-Audit": "header-only-secret"}}
+                   if provider in ("openai", "azure") else {}),
+            )
+
+        await asyncio.gather(run("request-one"), run("request-two"))
+        requests: Final = await asyncio.wait_for(asyncio.gather(outbound.get(), outbound.get()), timeout=10)
+        payloads: Final = await asyncio.wait_for(asyncio.gather(logs.get(), logs.get()), timeout=10)
+        for payload in payloads:
+            snapshot: Final = payload["classifier_input"]
+            assert snapshot in requests
+            assert "source-only" not in json.dumps(snapshot)
+            assert "classifier-rubric" in json.dumps(snapshot)
+            assert "transport-only" not in json.dumps(snapshot)
+            assert "header-only-secret" not in json.dumps(snapshot)
+            assert "SIMPLE" in json.dumps(payload["response"])
+            marker: Final = "request-one" if "request-one" in json.dumps(snapshot) else "request-two"
+            assert payload["originating_request_masked"] == {"input": f"source-only-{marker}"}
+            assert classifier_input_snapshot(snapshot) is not None
+        if provider not in ("openai", "azure", "responses"):
+            assert all("system" in request for request in requests)
+
+
+@pytest.mark.parametrize("redaction", ["none", "global", "request", "header"])
+@pytest.mark.parametrize("status", ["success", "failure"])
+@pytest.mark.parametrize("call_type", ["completion", "acompletion", "responses", "aresponses"])
+def test_classifier_audit_obeys_message_logging_before_payload_emission(logging_obj, monkeypatch, redaction, status, call_type):
+    from litellm.litellm_core_utils.litellm_logging import get_standard_logging_object_payload
+
+    monkeypatch.setattr(litellm, "turn_off_message_logging", redaction == "global")
+    params: Final = {
+        "metadata": {"internal_call_origin": "autorouter_classifier", **(
+            {"headers": {"x-litellm-enable-message-redaction": "true"}} if redaction == "header" else {}
+        )},
+        "proxy_server_request": {"body": {}, "originating_request_masked": {"input": "source-only"}},
+    }
+    logging_obj.call_type = call_type
+    logging_obj.model_call_details["litellm_params"] = params
+    logging_obj.model_call_details["standard_callback_dynamic_params"] = (
+        {"turn_off_message_logging": True} if redaction == "request" else {}
+    )
+    logging_obj.pre_call(
+        input=[], api_key=None, additional_args={"complete_input_dict": {"system": "rubric", "messages": []}}
+    )
+    now: Final = datetime.datetime.now()
+    payload: Final = get_standard_logging_object_payload(
+        kwargs={**logging_obj.model_call_details, "call_type": call_type}, init_response_obj={},
+        start_time=now, end_time=now, logging_obj=logging_obj, status=status,
+    )
+    assert payload is not None
+    if redaction == "none":
+        assert payload["classifier_input"] == {"system": "rubric", "messages": []}
+        assert payload["originating_request_masked"] == {"input": "source-only"}
+    else:
+        assert "classifier_input" not in payload
+        assert "originating_request_masked" not in payload
+
+
+@pytest.mark.parametrize("call_type,origin", [("completion", None), ("aembedding", "autorouter_classifier")])
+def test_classifier_audit_is_not_added_to_other_calls(logging_obj, call_type, origin):
+    logging_obj.call_type = call_type
+    logging_obj.model_call_details["litellm_params"] = {"metadata": {"internal_call_origin": origin}}
+    logging_obj.pre_call(input=[], api_key=None, additional_args={"complete_input_dict": {"input": "embedding"}})
+    assert logging_obj.classifier_input is None
+
+
+def _run_while_a_thread_grows(target: dict, read: Callable[[], None], reads: int) -> None:
+    import itertools
+    import threading
+
+    stop: Final = threading.Event()
+
+    def grow() -> None:
+        for counter in itertools.count():
+            if stop.is_set():
+                return
+            key: Final = f"late_{counter % 64}"
+            if key in target:
+                del target[key]
+            else:
+                target[key] = counter
+
+    writer: Final = threading.Thread(target=grow, daemon=True)
+    previous_interval: Final = sys.getswitchinterval()
+    sys.setswitchinterval(1e-6)
+    writer.start()
+    try:
+        for _ in range(reads):
+            read()
+    finally:
+        stop.set()
+        writer.join(timeout=5)
+        sys.setswitchinterval(previous_interval)
+
+
+def test_merge_litellm_metadata_survives_a_thread_growing_metadata_mid_merge():
+    from litellm.litellm_core_utils.litellm_logging import StandardLoggingPayloadSetup
+
+    metadata: Final = {f"key_{i}": i for i in range(2000)}
+    litellm_params: Final = {"metadata": metadata, "litellm_metadata": {"model_group": "gpt"}}
+
+    def read() -> None:
+        merged: Final = StandardLoggingPayloadSetup.merge_litellm_metadata(litellm_params)
+        assert merged["key_1999"] == 1999
+        assert merged["model_group"] == "gpt"
+
+    _run_while_a_thread_grows(metadata, read, reads=300)
+
+
+def test_get_additional_headers_survives_a_thread_growing_headers_mid_copy():
+    from litellm.litellm_core_utils.litellm_logging import StandardLoggingPayloadSetup
+
+    headers: Final = {f"llm_provider-x-custom-{i}": str(i) for i in range(2000)}
+    headers["x-ratelimit-remaining-requests"] = "7"
+
+    def read() -> None:
+        copied: Final = StandardLoggingPayloadSetup.get_additional_headers(headers)
+        assert copied is not None
+        assert copied["x_ratelimit_remaining_requests"] == 7
+        assert copied["llm_provider-x-custom-1999"] == "1999"
+
+    _run_while_a_thread_grows(headers, read, reads=300)
diff --git a/tests/test_litellm/litellm_core_utils/test_redact_messages.py b/tests/test_litellm/litellm_core_utils/test_redact_messages.py
index 3be0bae4120..76092e96307 100644
--- a/tests/test_litellm/litellm_core_utils/test_redact_messages.py
+++ b/tests/test_litellm/litellm_core_utils/test_redact_messages.py
@@ -6,6 +6,7 @@ but litellm_params["litellm_metadata"] is None.
 """
 
 import threading
+from typing import Final
 from types import SimpleNamespace
 
 import pytest
@@ -16,6 +17,7 @@ from litellm.litellm_core_utils.redact_messages import (
     _redact_responses_api_output,
     perform_redaction,
     redact_streaming_responses_for_custom_logger,
+    redacted_standard_logging_payload,
     should_redact_message_logging,
 )
 from litellm.responses.main import mock_responses_api_response
@@ -858,3 +860,69 @@ class TestRedactStreamingResponsesForCustomLogger:
 
         assert result_details is model_call_details
         assert response_obj.choices[0].message.content == "secret content"
+
+
+@pytest.mark.parametrize("callback_only", [False, True])
+def test_classifier_audit_redaction_removes_both_fields_and_source_carrier(callback_only: bool) -> None:
+    audit: Final = {"classifier_input": {"system": "private rubric"}, "originating_request_masked": {"input": "private source"}}
+    standard_payload: Final = {
+        **audit,
+        "messages": [{"role": "user", "content": "private prompt"}],
+        "response": {"choices": [{"message": {"content": "private answer"}}]},
+        "model": "classifier",
+    }
+    details: Final = {
+        "standard_logging_object": standard_payload,
+        "litellm_params": {"proxy_server_request": {"body": {}, "originating_request_masked": audit["originating_request_masked"]}},
+    }
+    logger: Final = CustomLogger()
+    logger.turn_off_message_logging = True
+    if callback_only:
+        redacted: Final = logger.redact_standard_logging_payload_from_model_call_details(details)
+        assert "classifier_input" not in redacted["standard_logging_object"]
+        assert "originating_request_masked" not in redacted["standard_logging_object"]
+        assert "originating_request_masked" not in redacted["litellm_params"]["proxy_server_request"]
+        assert details["standard_logging_object"]["classifier_input"] == audit["classifier_input"]
+        assert details["litellm_params"]["proxy_server_request"]["originating_request_masked"] == audit["originating_request_masked"]
+    else:
+        perform_redaction(details, result=None)
+        assert "classifier_input" not in details["standard_logging_object"]
+        assert "originating_request_masked" not in details["standard_logging_object"]
+        assert "originating_request_masked" not in details["litellm_params"]["proxy_server_request"]
+
+    assert standard_payload["classifier_input"] == audit["classifier_input"]
+    assert standard_payload["originating_request_masked"] == audit["originating_request_masked"]
+    assert standard_payload["messages"][0]["content"] == "private prompt"
+    assert standard_payload["response"]["choices"][0]["message"]["content"] == "private answer"
+
+
+@pytest.mark.parametrize("excluded", [False, True])
+def test_classifier_callback_redaction_preserves_exclusions(monkeypatch: pytest.MonkeyPatch, excluded: bool) -> None:
+    monkeypatch.setattr(litellm, "standard_logging_payload_excluded_fields", ["messages", "response"] if excluded else [])
+    payload: Final = {
+        "classifier_input": {"system": "private rubric"},
+        "originating_request_masked": {"input": "private source"},
+        "messages": [{"role": "user", "content": "private prompt"}],
+        "response": {"choices": [{"message": {"content": "private answer"}}]},
+        "model": "classifier",
+    }
+    logger: Final = CustomLogger()
+    logger.turn_off_message_logging = True
+    redacted: Final = logger.redact_standard_logging_payload_from_model_call_details({"standard_logging_object": payload})
+    stored: Final = redacted["standard_logging_object"]
+    assert "classifier_input" not in stored
+    assert "originating_request_masked" not in stored
+    assert stored["model"] == "classifier"
+    assert ("messages" not in stored) is excluded
+    assert ("response" not in stored) is excluded
+    if not excluded:
+        assert stored["messages"][0]["content"] == "redacted-by-litellm"
+        assert stored["response"]["choices"][0]["message"]["content"] == "redacted-by-litellm"
+
+    failure_payload: Final = redacted_standard_logging_payload(payload)
+    assert "classifier_input" not in failure_payload
+    assert "originating_request_masked" not in failure_payload
+    assert failure_payload["messages"][0]["content"] == "redacted-by-litellm"
+    assert failure_payload["response"]["choices"][0]["message"]["content"] == "redacted-by-litellm"
+    assert payload["classifier_input"] == {"system": "private rubric"}
+    assert payload["response"]["choices"][0]["message"]["content"] == "private answer"
diff --git a/tests/test_litellm/litellm_core_utils/test_sensitive_data_masker.py b/tests/test_litellm/litellm_core_utils/test_sensitive_data_masker.py
index c8b6772d965..1551c3fd6e6 100644
--- a/tests/test_litellm/litellm_core_utils/test_sensitive_data_masker.py
+++ b/tests/test_litellm/litellm_core_utils/test_sensitive_data_masker.py
@@ -358,7 +358,12 @@ def test_redact_credentials_in_payload_leaves_no_fragment_of_the_secret():
             "azure_ad_token": fake_token,
             "aws_secret_access_key": "fake-aws-secret-0000",
             "vertex_credentials": {"private_key": "fake-pem"},
-            "extra_headers": {"Authorization": "Bearer fake-bearer-0000", "x-request-id": "abc123"},
+            "extra_headers": {
+                "Authorization": "Bearer fake-bearer-0000",
+                "Cookie": "session=fake-session",
+                "Set-Cookie": "session=fake-session; HttpOnly",
+                "x-request-id": "abc123",
+            },
             "model": "gpt-4o-mini",
             "max_tokens": 17,
             "temperature": 0.25,
@@ -373,6 +378,8 @@ def test_redact_credentials_in_payload_leaves_no_fragment_of_the_secret():
     assert "fake-bearer-0000" not in str(result)
     assert result["api_key"] == "REDACTED"
     assert result["extra_headers"]["Authorization"] == "REDACTED"
+    assert result["extra_headers"]["Cookie"] == "REDACTED"
+    assert result["extra_headers"]["Set-Cookie"] == "REDACTED"
     assert result["extra_headers"]["x-request-id"] == "abc123"
     assert result["model"] == "gpt-4o-mini"
     assert result["max_tokens"] == 17
diff --git a/tests/test_litellm/litellm_core_utils/test_streaming_chunk_builder_utils.py b/tests/test_litellm/litellm_core_utils/test_streaming_chunk_builder_utils.py
index bacbcbf132b..efe4209c1c9 100644
--- a/tests/test_litellm/litellm_core_utils/test_streaming_chunk_builder_utils.py
+++ b/tests/test_litellm/litellm_core_utils/test_streaming_chunk_builder_utils.py
@@ -1,4 +1,6 @@
 import json
+from collections.abc import Mapping, Sequence
+from typing import Final
 
 import pytest
 
@@ -1476,3 +1478,128 @@ def test_calculate_usage_fills_unknown_split_from_reasoning_estimate(
     assert usage.completion_tokens == 100
     assert usage.completion_tokens_details.reasoning_tokens == expected_reasoning_tokens
     assert usage.completion_tokens_details.text_tokens == expected_text_tokens
+
+
+def _openai_chunk(
+    choices: Sequence[Mapping[str, object]], usage: Mapping[str, int] | None = None
+) -> dict[str, object]:
+    base: Final = {
+        "id": "chatcmpl-lit6552",
+        "object": "chat.completion.chunk",
+        "created": 1,
+        "model": "gpt-5.4-mini",
+        "choices": list(choices),
+    }
+    return base if usage is None else {**base, "usage": dict(usage)}
+
+
+@pytest.mark.parametrize(
+    "chunks",
+    [
+        pytest.param([_openai_chunk(choices=[]), _openai_chunk(choices=[])], id="all_empty_choices_dicts"),
+        pytest.param(
+            [ModelResponseStream(model="gpt-5.4-mini", choices=[]) for _ in range(2)],
+            id="all_empty_choices_objects",
+        ),
+    ],
+)
+def test_stream_chunk_builder_survives_all_empty_choices(chunks: Sequence[object]) -> None:
+    response: Final = stream_chunk_builder(chunks=list(chunks))
+
+    assert response is not None
+    assert response.choices[0].message.role == "assistant"
+    assert response.choices[0].finish_reason == "stop"
+
+
+def test_stream_chunk_builder_keeps_usage_from_usage_only_frames() -> None:
+    usage_frame: Final = _openai_chunk(
+        choices=[], usage={"prompt_tokens": 10, "completion_tokens": 0, "total_tokens": 10}
+    )
+
+    response: Final = stream_chunk_builder(chunks=[usage_frame])
+
+    assert response is not None
+    assert response.choices[0].message.role == "assistant"
+    assert response.usage.prompt_tokens == 10
+    assert response.usage.total_tokens == 10
+
+
+@pytest.mark.parametrize(
+    "delta",
+    [pytest.param({"content": "Hi"}, id="delta_without_role"), pytest.param({}, id="empty_delta")],
+)
+def test_stream_chunk_builder_defaults_role_when_delta_omits_it(delta: Mapping[str, str]) -> None:
+    chunks: Final = [
+        _openai_chunk(choices=[{"index": 0, "delta": dict(delta), "finish_reason": None}]),
+        _openai_chunk(choices=[{"index": 0, "delta": {"content": "!"}, "finish_reason": "stop"}]),
+    ]
+
+    response: Final = stream_chunk_builder(chunks=chunks)
+
+    assert response is not None
+    assert response.choices[0].message.role == "assistant"
+    assert response.choices[0].message.content == delta.get("content", "") + "!"
+    assert response.choices[0].finish_reason == "stop"
+
+
+def test_stream_chunk_builder_reads_role_from_first_frame_with_choices() -> None:
+    chunks: Final = [
+        _openai_chunk(choices=[]),
+        _openai_chunk(choices=[{"index": 0, "delta": {"role": "user", "content": "Hi"}, "finish_reason": None}]),
+        _openai_chunk(choices=[{"index": 0, "delta": {}, "finish_reason": "stop"}]),
+    ]
+
+    response: Final = stream_chunk_builder(chunks=chunks)
+
+    assert response is not None
+    assert response.choices[0].message.role == "user"
+    assert response.choices[0].message.content == "Hi"
+
+
+def _fail_prompt_token_count() -> int:
+    raise AssertionError("prompt tokens must come from the usage chunk, not the tokenizer")
+
+
+def test_calculate_usage_reads_prompt_tokens_from_mock_stream_usage_chunk_without_tokenizer_fallback() -> None:
+    from litellm.utils import mock_completion_streaming_obj
+
+    chunks: Final = list(
+        mock_completion_streaming_obj(
+            ModelResponseStream(model="gpt-5.4-mini"),
+            mock_response="ok",
+            model="gpt-5.4-mini",
+            prompt_tokens=51234,
+        )
+    )
+    assert chunks[-1].choices == []
+
+    usage: Final = ChunkProcessor(chunks=chunks).calculate_usage(
+        chunks=chunks,
+        model="gpt-5.4-mini",
+        completion_output="ok",
+        count_prompt_tokens=_fail_prompt_token_count,
+    )
+
+    assert usage.prompt_tokens == 51234
+    assert usage.completion_tokens == chunks[-1].usage.completion_tokens
+    assert usage.total_tokens == 51234 + usage.completion_tokens
+
+
+def test_calculate_usage_falls_back_to_prompt_counter_when_mock_stream_has_no_admission_count() -> None:
+    from litellm.utils import mock_completion_streaming_obj
+
+    chunks: Final = list(
+        mock_completion_streaming_obj(
+            ModelResponseStream(model="gpt-5.4-mini"), mock_response="ok", model="gpt-5.4-mini"
+        )
+    )
+    assert all(chunk.choices for chunk in chunks)
+
+    usage: Final = ChunkProcessor(chunks=chunks).calculate_usage(
+        chunks=chunks,
+        model="gpt-5.4-mini",
+        completion_output="ok",
+        count_prompt_tokens=lambda: 77,
+    )
+
+    assert usage.prompt_tokens == 77
diff --git a/tests/test_litellm/litellm_core_utils/test_streaming_handler.py b/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
index 0aa73833677..37e2031fdf4 100644
--- a/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
+++ b/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
@@ -6,7 +6,7 @@ import pytest
 
 import asyncio
 import traceback
-from typing import Optional
+from typing import Final, Optional
 
 import litellm
 from litellm import verbose_logger
@@ -2633,6 +2633,48 @@ def test_dispatch_cached_response_extracts_delta(
     assert initialized_custom_stream_wrapper.response_id == "chatcmpl-cache-1"
 
 
+def test_dispatch_cached_response_without_choices_is_an_empty_chunk(
+    initialized_custom_stream_wrapper: CustomStreamWrapper,
+):
+    """A cached completion with no choices replays as an empty, unfinished chunk
+    instead of raising IndexError on choices[0]."""
+    initialized_custom_stream_wrapper.custom_llm_provider = "cached_response"
+    chunk: Final = ModelResponseStream(id="chatcmpl-cache-empty", choices=[])
+
+    result, model_response, completion_obj = _run_dispatch(
+        initialized_custom_stream_wrapper, chunk
+    )
+
+    assert isinstance(result, _ProviderChunkParsed)
+    assert completion_obj["content"] is None
+    assert initialized_custom_stream_wrapper.received_finish_reason is None
+    assert model_response.id == "chatcmpl-cache-empty"
+
+
+@pytest.mark.asyncio
+async def test_cached_response_without_choices_streams_a_single_stop_chunk(
+    logging_obj: Logging,
+):
+    """A stream cache hit on a completion stored with choices == [] ends with one
+    finish_reason=stop chunk, the same shape the live empty stream produced."""
+
+    async def cached_chunks():
+        yield ModelResponseStream(id="chatcmpl-cache-empty", choices=[])
+
+    wrapper: Final = CustomStreamWrapper(
+        completion_stream=cached_chunks(),
+        model="test-model",
+        logging_obj=logging_obj,
+        custom_llm_provider="cached_response",
+    )
+
+    chunks: Final = tuple([chunk async for chunk in wrapper])
+
+    assert len(chunks) == 1
+    assert tuple(choice.finish_reason for chunk in chunks for choice in chunk.choices) == ("stop",)
+    assert all(choice.delta.content in (None, "") for chunk in chunks for choice in chunk.choices)
+
+
 def test_dispatch_vertex_ai_legacy_text_and_finish_reason(
     initialized_custom_stream_wrapper: CustomStreamWrapper,
 ):
diff --git a/tests/test_litellm/litellm_core_utils/test_token_counter.py b/tests/test_litellm/litellm_core_utils/test_token_counter.py
index 4694fa8fbed..60f25c48443 100644
--- a/tests/test_litellm/litellm_core_utils/test_token_counter.py
+++ b/tests/test_litellm/litellm_core_utils/test_token_counter.py
@@ -1,10 +1,16 @@
 #### What this tests ####
 #    This tests litellm.token_counter.token_counter() function
+import asyncio
+import base64
 import importlib
+import threading
 import time
 import traceback
+from concurrent.futures import Future, wait
+from typing import Final
 from unittest.mock import MagicMock
 
+import anyio.to_thread
 import pytest
 import tiktoken
 
@@ -14,9 +20,23 @@ import litellm
 from litellm import create_pretrained_tokenizer, decode, encode, get_modified_max_tokens
 from litellm import token_counter as token_counter_old
 import litellm.constants
-from litellm.litellm_core_utils.token_counter import _get_tiktoken_count_function
+from litellm.constants import TOKEN_COUNTER_MAX_CONCURRENT_COUNTS
+from litellm.litellm_core_utils.asyncify import asyncify
+from litellm.litellm_core_utils.token_counter import (
+    _get_exact_count_function,
+    _get_extrapolating_count_function,
+    _get_tiktoken_count_function,
+    calculate_img_tokens,
+    high_detail_image_token_upper_bound,
+    offload_token_count,
+)
 from litellm.litellm_core_utils.token_counter import token_counter as token_counter_new
 from tests.large_text import text
+from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+    assert_loop_stayed_free,
+    timed_with_loop_lags,
+    warm_tokenizer,
+)
 from tests.test_litellm.litellm_core_utils.messages_with_counts import (
     MESSAGES_TEXT,
     MESSAGES_WITH_IMAGES,
@@ -120,6 +140,135 @@ def test_valid_chunk_size_config_is_honoured(monkeypatch):
         importlib.reload(litellm.constants)
 
 
+async def test_huggingface_count_in_a_worker_thread_leaves_the_event_loop_free():
+    warm_tokenizer("claude-fable-5")
+
+    tokens, took, lags = await timed_with_loop_lags(
+        lambda: asyncify(token_counter_new)(model="claude-fable-5", text=text * 100)
+    )
+
+    assert tokens > 0
+    assert_loop_stayed_free(took, lags)
+
+
+@pytest.mark.parametrize("max_exact_chars", [64, 1_000, 2_500])
+def test_count_above_the_cap_samples_the_whole_string_and_scales(max_exact_chars: int):
+    count_exactly: Final = MagicMock(side_effect=lambda chunk: chunk.count("a") + len(chunk))
+    front_heavy: Final = "a" * 1_000 + "b" * 4_000
+    exact: Final = 1_000 + len(front_heavy)
+
+    estimate: Final = _get_extrapolating_count_function(count_exactly, max_exact_chars=max_exact_chars)(front_heavy)
+
+    assert abs(estimate - exact) <= exact // 100
+    assert sum(len(call.args[0]) for call in count_exactly.call_args_list) <= max_exact_chars
+
+
+def test_count_at_or_below_the_cap_is_exact():
+    count_exactly: Final = MagicMock(side_effect=len)
+
+    assert _get_extrapolating_count_function(count_exactly, max_exact_chars=5_000)("a" * 5_000) == 5_000
+    assert count_exactly.call_args_list == [(("a" * 5_000,),)]
+
+
+class _SlowEncoder:
+    def __init__(self) -> None:
+        self._lock: Final = threading.Lock()
+        self.in_flight = 0
+        self.peak_in_flight = 0
+
+    def encode_batch_fast(self, texts: list[str]) -> list[list[int]]:
+        with self._lock:
+            self.in_flight += 1
+            self.peak_in_flight = max(self.peak_in_flight, self.in_flight)
+        time.sleep(0.1)
+        with self._lock:
+            self.in_flight -= 1
+        return [[0] * len(text) for text in texts]
+
+
+@pytest.mark.asyncio
+async def test_offloaded_counts_do_not_borrow_from_the_shared_thread_pool():
+    encoder: Final = _SlowEncoder()
+    count: Final = _get_exact_count_function(None, {"type": "huggingface_tokenizer", "tokenizer": encoder})
+    shared_pool: Final = anyio.to_thread.current_default_thread_limiter()
+    burst: Final = 2 * TOKEN_COUNTER_MAX_CONCURRENT_COUNTS
+
+    async def shared_pool_borrowed_until_done(counting: asyncio.Future[list[int]]) -> tuple[int, ...]:
+        if counting.done():
+            return ()
+        await asyncio.sleep(0.01)
+        return (shared_pool.borrowed_tokens, *await shared_pool_borrowed_until_done(counting))
+
+    counting: Final = asyncio.ensure_future(asyncio.gather(*(offload_token_count(count)("abc") for _ in range(burst))))
+    borrowed: Final = await shared_pool_borrowed_until_done(counting)
+
+    assert await counting == [3] * burst
+    assert len(borrowed) > 1 and max(borrowed) == 0
+    assert 1 < encoder.peak_in_flight <= TOKEN_COUNTER_MAX_CONCURRENT_COUNTS
+
+
+def _count_in_a_fresh_event_loop(text: str, result: Future[int]) -> None:
+    def slow_count(counted: str) -> int:
+        time.sleep(0.1)
+        return len(counted)
+
+    result.set_result(asyncio.run(offload_token_count(slow_count)(text)))
+
+
+def test_offloaded_counts_finish_in_every_event_loop_that_shares_the_process():
+    loops: Final = 2 * TOKEN_COUNTER_MAX_CONCURRENT_COUNTS
+    results: Final = tuple(Future[int]() for _ in range(loops))
+    threads: Final = tuple(
+        threading.Thread(target=_count_in_a_fresh_event_loop, args=("a" * size, result), daemon=True)
+        for size, result in enumerate(results, start=1)
+    )
+    for thread in threads:
+        thread.start()
+
+    _, pending = wait(results, timeout=5)
+
+    assert not pending
+    assert tuple(result.result() for result in results) == tuple(range(1, loops + 1))
+
+
+@pytest.mark.parametrize(
+    ("configured", "expected"),
+    [("8", 8), ("0", 4), ("not-an-int", 4)],
+)
+def test_max_concurrent_counts_config_is_honoured(monkeypatch: pytest.MonkeyPatch, configured: str, expected: int):
+    monkeypatch.setenv("TOKEN_COUNTER_MAX_CONCURRENT_COUNTS", configured)
+    try:
+        assert importlib.reload(litellm.constants).TOKEN_COUNTER_MAX_CONCURRENT_COUNTS == expected
+    finally:
+        monkeypatch.delenv("TOKEN_COUNTER_MAX_CONCURRENT_COUNTS")
+        importlib.reload(litellm.constants)
+
+
+def test_token_counter_applies_the_default_cap():
+    max_exact_chars: Final = litellm.constants.TOKEN_COUNTER_MAX_EXACT_CHARS
+    prose: Final = ("The quick brown fox jumps over the lazy dog. " * (max_exact_chars // 45 + 1))[:max_exact_chars]
+    over_the_cap: Final = prose + "a" * 200_000
+    exact: Final = _get_exact_count_function("gpt-5.6")(over_the_cap)
+
+    estimate: Final = token_counter_new(model="gpt-5.6", text=over_the_cap)
+
+    assert estimate != exact
+    assert abs(estimate - exact) <= exact // 100
+
+
+@pytest.mark.parametrize(
+    ("configured", "expected"),
+    [("2048", 2048), ("0", 4_000_000), ("not-an-int", 4_000_000)],
+)
+def test_max_exact_chars_config_is_honoured(monkeypatch: pytest.MonkeyPatch, configured: str, expected: int):
+    monkeypatch.setenv("TOKEN_COUNTER_MAX_EXACT_CHARS", configured)
+    try:
+        assert importlib.reload(litellm.constants).TOKEN_COUNTER_MAX_EXACT_CHARS == expected
+    finally:
+        monkeypatch.delenv("TOKEN_COUNTER_MAX_EXACT_CHARS")
+        importlib.reload(litellm.constants)
+
+
 def test_token_counter_with_prefix():
     messages = [
         {"role": "user", "content": "Who won the world cup in 2022?"},
@@ -1412,3 +1561,18 @@ def test_openai_file_block_without_inline_bytes_counts_what_it_carries():
     assert _count_user_content([prompt, named]) == _count_user_content(
         [prompt, {"type": "text", "text": "report.pdf"}]
     )
+
+
+def _png_data_url(width: int, height: int) -> str:
+    ihdr = b"\x89PNG\r\n\x1a\n" + (13).to_bytes(4, "big") + b"IHDR" + width.to_bytes(4, "big") + height.to_bytes(4, "big")
+    return "data:image/png;base64," + base64.b64encode(ihdr + b"\x08\x06\x00\x00\x00").decode()
+
+
+@pytest.mark.parametrize(("width", "height"), [(1, 1), (768, 768), (2000, 768), (768, 2000), (4096, 4096), (8000, 3072)])
+def test_high_detail_image_token_upper_bound_covers_every_image_size(width: int, height: int) -> None:
+    assert calculate_img_tokens(_png_data_url(width, height), mode="high") <= high_detail_image_token_upper_bound()
+
+
+def test_high_detail_image_token_upper_bound_is_reached_by_the_largest_high_res_image() -> None:
+    assert calculate_img_tokens(_png_data_url(2000, 768), mode="high") == high_detail_image_token_upper_bound()
+    assert calculate_img_tokens(_png_data_url(1, 1), mode="high") < high_detail_image_token_upper_bound()
diff --git a/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py b/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
index bf40f781fa3..9fe56f4dc65 100644
--- a/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
+++ b/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
@@ -315,6 +315,120 @@ class TestAnthropicMessagesHandlerStreamingOutputProcessing:
         assert "event: message_start" in raw and "event: message_stop" in raw
         assert '"stop_reason": "end_turn"' in raw
 
+    @staticmethod
+    def _ended_tool_use_sse_chunks() -> list:
+        events = [
+            ("message_start", {"type": "message_start", "message": {"id": "msg_1", "type": "message", "role": "assistant", "model": "claude-sonnet-4-5", "content": [], "stop_reason": None, "usage": {"input_tokens": 1, "output_tokens": 0}}}),
+            ("content_block_start", {"type": "content_block_start", "index": 0, "content_block": {"type": "tool_use", "id": "toolu_1", "name": "lookup_fruit", "input": {}}}),
+            ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "input_json_delta", "partial_json": ""}}),
+            ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "input_json_delta", "partial_json": '{"fruit": "persim'}}),
+            ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "input_json_delta", "partial_json": 'mon"}'}}),
+            ("content_block_stop", {"type": "content_block_stop", "index": 0}),
+            ("message_delta", {"type": "message_delta", "delta": {"stop_reason": "tool_use", "stop_sequence": None}, "usage": {"output_tokens": 2}}),
+            ("message_stop", {"type": "message_stop"}),
+        ]
+        return [f"event: {name}\ndata: {json.dumps(payload)}\n\n".encode() for name, payload in events]
+
+    @staticmethod
+    def _argument_masking_guardrail() -> CustomGuardrail:
+        class MaskArguments(CustomGuardrail):
+            async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+                for tool_call in inputs.get("tool_calls", []):
+                    tool_call.function.arguments = '{"fruit": "[MASKED]"}'
+                return inputs
+
+        return MaskArguments(guardrail_name="test")
+
+    @staticmethod
+    def _partial_jsons(chunks: list) -> list:
+        return [
+            json.loads(line[len("data:") :].strip())["delta"]["partial_json"]
+            for chunk in chunks
+            for line in chunk.decode().split("\n")
+            if line.startswith("data:") and json.loads(line[len("data:") :].strip()).get("type") == "content_block_delta"
+        ]
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_writes_tool_use_input_back_into_sse_chunks(self):
+        handler = AnthropicMessagesHandler()
+        chunks = self._ended_tool_use_sse_chunks()
+
+        result = await handler.process_output_streaming_response(
+            responses_so_far=chunks,
+            guardrail_to_apply=self._argument_masking_guardrail(),
+            litellm_logging_obj=MagicMock(),
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert result is chunks
+        assert self._partial_jsons(chunks) == ['{"fruit": "[MASKED]"}', "", ""]
+        raw = b"".join(chunks).decode()
+        assert '"name": "lookup_fruit"' in raw and '"id": "toolu_1"' in raw
+        assert '"stop_reason": "tool_use"' in raw
+        assert "persim" not in raw
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_writes_tool_use_name_back_into_sse_chunks(self):
+        class RenameTool(CustomGuardrail):
+            async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+                for tool_call in inputs.get("tool_calls", []):
+                    tool_call.function.name = "lookup_fruit_reviewed"
+                return inputs
+
+        handler = AnthropicMessagesHandler()
+        chunks = self._ended_tool_use_sse_chunks()
+
+        await handler.process_output_streaming_response(
+            responses_so_far=chunks,
+            guardrail_to_apply=RenameTool(guardrail_name="test"),
+            litellm_logging_obj=MagicMock(),
+            deliver_ended_stream_rewrites=True,
+        )
+
+        raw = b"".join(chunks).decode()
+        assert '"name": "lookup_fruit_reviewed"' in raw and '"id": "toolu_1"' in raw
+        assert '"name": "lookup_fruit"' not in raw
+        assert json.loads("".join(self._partial_jsons(chunks))) == {"fruit": "persimmon"}
+
+    @pytest.mark.asyncio
+    async def test_ended_stream_tool_use_rewrite_leaves_chunks_untouched_by_default(self):
+        handler = AnthropicMessagesHandler()
+        chunks = self._ended_tool_use_sse_chunks()
+        original = [bytes(chunk) for chunk in chunks]
+
+        await handler.process_output_streaming_response(
+            responses_so_far=chunks,
+            guardrail_to_apply=self._argument_masking_guardrail(),
+            litellm_logging_obj=MagicMock(),
+        )
+
+        assert chunks == original
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_tool_use_rewrite_with_server_tool_use_block_fails_closed(self):
+        from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+        handler = AnthropicMessagesHandler()
+        server_tool_use = [
+            ("content_block_start", {"type": "content_block_start", "index": 0, "content_block": {"type": "server_tool_use", "id": "srvtoolu_1", "name": "web_search", "input": {}}}),
+            ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "input_json_delta", "partial_json": '{"query": "fruit"}'}}),
+            ("content_block_stop", {"type": "content_block_stop", "index": 0}),
+        ]
+        tool_use = self._ended_tool_use_sse_chunks()
+        chunks = (
+            tool_use[:1]
+            + [f"event: {name}\ndata: {json.dumps(payload)}\n\n".encode() for name, payload in server_tool_use]
+            + [chunk.replace(b'"index": 0', b'"index": 1') for chunk in tool_use[1:]]
+        )
+
+        with pytest.raises(UndeliverableStreamRewrite):
+            await handler.process_output_streaming_response(
+                responses_so_far=chunks,
+                guardrail_to_apply=self._argument_masking_guardrail(),
+                litellm_logging_obj=MagicMock(),
+                deliver_ended_stream_rewrites=True,
+            )
+
     @pytest.mark.asyncio
     async def test_ended_stream_rewrite_leaves_chunks_untouched_by_default(self):
         handler = AnthropicMessagesHandler()
@@ -2156,3 +2270,29 @@ class TestAnthropicMessagesHandlerStreamingScanKey:
         assert open_key == StreamingScanKey(texts=("hi",))
         assert len(ended_key.tool_calls) == 1 and "get_weather" in ended_key.tool_calls[0]
         assert ended_key != open_key
+
+
+class TestAnthropicMessagesHandlerPostCallHookResponse:
+    def test_openai_shaped_stream_assembly_reaches_the_hook_as_a_messages_response(self):
+        from litellm.types.utils import Choices, Message, ModelResponse, Usage
+
+        assembled = ModelResponse(
+            id="msg_1",
+            model="claude",
+            choices=[Choices(message=Message(role="assistant", content="hello world"), finish_reason="stop")],
+            usage=Usage(prompt_tokens=1, completion_tokens=2, total_tokens=3),
+        )
+
+        hook_response = AnthropicMessagesHandler().post_call_hook_response(assembled)
+
+        assert hook_response["type"] == "message"
+        assert hook_response["role"] == "assistant"
+        assert hook_response["content"] == [{"type": "text", "text": "hello world"}]
+        assert hook_response["stop_reason"] == "end_turn"
+        assert hook_response["usage"]["input_tokens"] == 1
+        assert hook_response["usage"]["output_tokens"] == 2
+
+    def test_anything_else_reaches_the_hook_untouched(self):
+        native = {"type": "message", "role": "assistant", "content": [{"type": "text", "text": "hi"}]}
+
+        assert AnthropicMessagesHandler().post_call_hook_response(native) is native
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_anthropic_experimental_pass_through_adapters_transformation.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_anthropic_experimental_pass_through_adapters_transformation.py
index c59ec70b015..f6ee1cd71c0 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_anthropic_experimental_pass_through_adapters_transformation.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_anthropic_experimental_pass_through_adapters_transformation.py
@@ -10,6 +10,7 @@ import litellm
 
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     TOOL_RESULT_IMAGE_PLACEHOLDER,
+    encrypted_reasoning_signature,
 )
 from litellm.litellm_core_utils.prompt_templates.factory import (
     THOUGHT_SIGNATURE_SEPARATOR,
@@ -41,6 +42,21 @@ from litellm.types.utils import (
 )
 
 
+def test_translate_openai_response_to_anthropic_empty_choices() -> None:
+    response: Final = ModelResponse(
+        id="chatcmpl-empty",
+        model="gemini-3.5-flash",
+        choices=[],
+        usage=Usage(prompt_tokens=10, completion_tokens=0, total_tokens=10),
+    )
+
+    result: Final = LiteLLMAnthropicMessagesAdapter().translate_openai_response_to_anthropic(response)
+
+    assert result["content"] == []
+    assert result["stop_reason"] == "end_turn"
+    assert result["usage"]["input_tokens"] == 10
+
+
 def test_translate_chat_refusal_to_anthropic_response():
     response = ModelResponse(
         id="chatcmpl-refusal",
@@ -408,6 +424,43 @@ def test_translate_anthropic_messages_to_openai_thinking_blocks():
     assert result[1]["tool_calls"][0]["id"] == "toolu_01234"
 
 
+def test_translate_anthropic_messages_to_openai_drops_bridge_encrypted_reasoning_blocks():
+    """A session that moves from an OpenAI reasoning model to a chat provider replays reasoning only OpenAI can read.
+
+    Gemini rejects the whole request when such a block reaches it as a thought_signature, so the
+    adapter drops those blocks and keeps the provider-signed ones.
+    """
+
+    anthropic_messages = [
+        AnthropicMessagesUserMessageParam(
+            role="user",
+            content=[{"type": "text", "text": "Who drinks water?"}],
+        ),
+        AnthopicMessagesAssistantMessageParam(
+            role="assistant",
+            content=[
+                {"type": "thinking", "thinking": "plan", "signature": encrypted_reasoning_signature("gAAAA_1")},
+                {"type": "redacted_thinking", "data": encrypted_reasoning_signature("gAAAA_2")},
+                {"type": "text", "text": "The Norwegian."},
+            ],
+        ),
+        AnthopicMessagesAssistantMessageParam(
+            role="assistant",
+            content=[
+                {"type": "thinking", "thinking": "native", "signature": "EqQBCkYIAxgCIkA_signed"},
+                {"type": "text", "text": "Still the Norwegian."},
+            ],
+        ),
+    ]
+
+    result = LiteLLMAnthropicMessagesAdapter().translate_anthropic_messages_to_openai(messages=anthropic_messages)
+
+    assert [m["role"] for m in result] == ["user", "assistant", "assistant"]
+    assert not result[1].get("thinking_blocks")
+    assert result[1]["content"] == "The Norwegian."
+    assert [b["signature"] for b in result[2]["thinking_blocks"]] == ["EqQBCkYIAxgCIkA_signed"]
+
+
 def test_translate_anthropic_messages_to_openai_sets_reasoning_content():
     """Reasoning-aware chat providers read reasoning_content, so thinking text must land there.
 
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_messages_encrypted_reasoning.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_messages_encrypted_reasoning.py
new file mode 100644
index 00000000000..c64e9d392e5
--- /dev/null
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_anthropic_messages_encrypted_reasoning.py
@@ -0,0 +1,50 @@
+from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    encrypted_reasoning_signature,
+)
+from litellm.llms.anthropic.experimental_pass_through.messages.transformation import (
+    AnthropicMessagesConfig,
+)
+
+
+def _transform(messages):
+    return AnthropicMessagesConfig().transform_anthropic_messages_request(
+        model="claude-sonnet-4-5",
+        messages=messages,
+        anthropic_messages_optional_request_params={"max_tokens": 1024},
+        litellm_params={},
+        headers={},
+    )
+
+
+def test_reasoning_replayed_from_the_responses_bridge_never_reaches_anthropic():
+    """Claude Code resumed on a Claude model echoes the thinking blocks a gpt turn produced."""
+    messages = [
+        {"role": "user", "content": "Solve it."},
+        {
+            "role": "assistant",
+            "content": [
+                {"type": "thinking", "thinking": "plan", "signature": encrypted_reasoning_signature("gAAAA_1")},
+                {"type": "redacted_thinking", "data": encrypted_reasoning_signature("gAAAA_2")},
+                {"type": "text", "text": "The answer."},
+            ],
+        },
+        {"role": "user", "content": "And the next one?"},
+    ]
+    request = _transform(messages)
+    assert request["messages"][1]["content"] == [{"type": "text", "text": "The answer."}]
+    assert len(messages[1]["content"]) == 3
+
+
+def test_anthropic_signed_thinking_blocks_are_forwarded_untouched():
+    messages = [
+        {"role": "user", "content": "Solve it."},
+        {
+            "role": "assistant",
+            "content": [
+                {"type": "thinking", "thinking": "plan", "signature": "EqQBCkYIAxgCIkA_anthropic_signed"},
+                {"type": "redacted_thinking", "data": "EmwKAhgBEgy_anthropic_minted"},
+                {"type": "text", "text": "The answer."},
+            ],
+        },
+    ]
+    assert _transform(messages)["messages"] == messages
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_handler.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_handler.py
index 16e8cf0e90e..b66075f691b 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_handler.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_handler.py
@@ -67,6 +67,39 @@ def test_build_responses_kwargs_prefers_explicit_prompt_cache_key_over_derived()
     assert responses_kwargs["prompt_cache_key"] == "explicit-key"
 
 
+def test_build_responses_kwargs_asks_openai_for_encrypted_reasoning_without_thinking():
+    responses_kwargs = _build_responses_kwargs(
+        max_tokens=1024,
+        messages=MESSAGES,
+        model="openai/gpt-5.6-luna",
+        extra_kwargs={"custom_llm_provider": "openai"},
+    )
+    assert responses_kwargs["include"] == ["reasoning.encrypted_content"]
+    assert "reasoning" not in responses_kwargs
+
+
+def test_build_responses_kwargs_skips_include_for_a_responses_provider_that_rejects_it():
+    responses_kwargs = _build_responses_kwargs(
+        max_tokens=1024,
+        messages=MESSAGES,
+        model="perplexity/sonar",
+        thinking={"type": "enabled", "budget_tokens": 4096},
+        extra_kwargs={"custom_llm_provider": "perplexity"},
+    )
+    assert "include" not in responses_kwargs
+    assert "reasoning" in responses_kwargs
+
+
+def test_build_responses_kwargs_keeps_the_deployment_include_next_to_encrypted_reasoning():
+    responses_kwargs = _build_responses_kwargs(
+        max_tokens=1024,
+        messages=MESSAGES,
+        model="openai/gpt-5.6-luna",
+        extra_kwargs={"custom_llm_provider": "openai", "include": ["file_search_call.results"]},
+    )
+    assert responses_kwargs["include"] == ["reasoning.encrypted_content", "file_search_call.results"]
+
+
 def test_build_responses_kwargs_without_metadata_sets_no_prompt_cache_key():
     responses_kwargs = _build_responses_kwargs(
         max_tokens=1024,
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_streaming_iterator.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_streaming_iterator.py
index d9df5df426a..bfe2d6b7cea 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_streaming_iterator.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_streaming_iterator.py
@@ -10,6 +10,9 @@ from types import SimpleNamespace
 
 sys.path.insert(0, os.path.abspath(os.path.join(os.path.dirname(__file__), "../../../../../..")))
 
+from litellm.litellm_core_utils.prompt_templates.common_utils import (
+    encrypted_reasoning_signature,
+)
 from litellm.llms.anthropic.experimental_pass_through.responses_adapters.streaming_iterator import (
     AnthropicResponsesStreamWrapper,
 )
@@ -114,7 +117,7 @@ class TestReasoningItemWithoutSummaryText:
     """
 
     @staticmethod
-    def _gpt_turn(reasoning_summary_deltas: list) -> list:
+    def _gpt_turn(reasoning_summary_deltas: list, encrypted_content: str | None = None) -> list:
         return [
             {"type": "response.created"},
             {"type": "response.output_item.added", "item": {"type": "reasoning", "id": "rs_1"}},
@@ -122,7 +125,10 @@ class TestReasoningItemWithoutSummaryText:
                 {"type": "response.reasoning_summary_text.delta", "item_id": "rs_1", "delta": delta}
                 for delta in reasoning_summary_deltas
             ),
-            {"type": "response.output_item.done", "item": {"type": "reasoning", "id": "rs_1"}},
+            {
+                "type": "response.output_item.done",
+                "item": {"type": "reasoning", "id": "rs_1", "encrypted_content": encrypted_content},
+            },
             {"type": "response.output_item.added", "item": {"type": "message", "id": "msg_1"}},
             {"type": "response.output_text.delta", "item_id": "msg_1", "delta": "Hello"},
             {"type": "response.output_item.done", "item": {"type": "message", "id": "msg_1"}},
@@ -171,6 +177,70 @@ class TestReasoningItemWithoutSummaryText:
         assert not [c for c in chunks if c.get("delta", {}).get("type") == "signature_delta"]
 
 
+_ENCRYPTED_REASONING = "gAAAAABp_encrypted_reasoning_bytes_only_openai_can_read"
+
+
+class TestEncryptedReasoningIsStreamedForReplay:
+    """Regression for https://github.com/BerriAI/litellm/issues/40288.
+
+    The client echoes a thinking block's signature (or a redacted block's data) back on the
+    next turn, so the item's ``encrypted_content`` has to reach it through one of those.
+    """
+
+    def test_encrypted_content_is_streamed_as_the_signature_before_the_block_closes(self):
+        chunks = _drain_async(
+            TestReasoningItemWithoutSummaryText._gpt_turn(
+                reasoning_summary_deltas=["Weighing options"], encrypted_content=_ENCRYPTED_REASONING
+            )
+        )
+
+        assert [(c["type"], c.get("index"), c.get("delta", {}).get("type")) for c in chunks[1:5]] == [
+            ("content_block_start", 0, None),
+            ("content_block_delta", 0, "thinking_delta"),
+            ("content_block_delta", 0, "signature_delta"),
+            ("content_block_stop", 0, None),
+        ]
+        assert chunks[3]["delta"]["signature"] == encrypted_reasoning_signature(_ENCRYPTED_REASONING)
+
+    def test_reasoning_without_summary_streams_a_redacted_thinking_block(self):
+        chunks = _drain_async(
+            TestReasoningItemWithoutSummaryText._gpt_turn(
+                reasoning_summary_deltas=[], encrypted_content=_ENCRYPTED_REASONING
+            )
+        )
+
+        assert [(c["type"], c.get("index")) for c in chunks[1:]] == [
+            ("content_block_start", 0),
+            ("content_block_stop", 0),
+            ("content_block_start", 1),
+            ("content_block_delta", 1),
+            ("content_block_stop", 1),
+        ]
+        assert chunks[1]["content_block"] == {
+            "type": "redacted_thinking",
+            "data": encrypted_reasoning_signature(_ENCRYPTED_REASONING),
+        }
+
+    def test_summary_parts_are_separated_inside_the_one_thinking_block(self):
+        """Two summary parts read as two paragraphs, not as one run-on sentence."""
+        events = [
+            {"type": "response.created"},
+            {"type": "response.output_item.added", "item": {"type": "reasoning", "id": "rs_1"}},
+            {"type": "response.reasoning_summary_part.added", "item_id": "rs_1", "summary_index": 0},
+            {"type": "response.reasoning_summary_text.delta", "item_id": "rs_1", "delta": "First."},
+            {"type": "response.reasoning_summary_part.added", "item_id": "rs_1", "summary_index": 1},
+            {"type": "response.reasoning_summary_text.delta", "item_id": "rs_1", "delta": "Second."},
+            {"type": "response.output_item.done", "item": {"type": "reasoning", "id": "rs_1"}},
+        ]
+        chunks = _process_all(events)
+
+        thinking = "".join(
+            c["delta"]["thinking"] for c in chunks if c.get("delta", {}).get("type") == "thinking_delta"
+        )
+        assert thinking == "First.\n\nSecond."
+        assert [c["type"] for c in chunks].count("content_block_start") == 1
+
+
 class TestToolUseBlockClosedExactlyOnce:
     """Regression for https://github.com/BerriAI/litellm/issues/37273.
 
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_transformation.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_transformation.py
index edcc7adddb7..4ad559aa547 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_transformation.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/responses_adapters/test_responses_adapters_transformation.py
@@ -19,6 +19,7 @@ from litellm.constants import (
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     TOOL_RESULT_IMAGE_BOUNDARY,
     TOOL_RESULT_IMAGE_PLACEHOLDER,
+    encrypted_reasoning_signature,
 )
 from litellm.llms.anthropic.experimental_pass_through.responses_adapters.transformation import (
     LiteLLMAnthropicToResponsesAPIAdapter,
@@ -566,6 +567,66 @@ class TestTranslateMessagesToResponsesInput:
         result = _translate_messages(messages)
         assert "id" not in result[0]
 
+    def test_thinking_block_with_encrypted_signature_replays_the_encrypted_content(self):
+        """Regression for https://github.com/BerriAI/litellm/issues/40288 (inbound fault site)."""
+        messages = [
+            {
+                "role": "assistant",
+                "content": [
+                    {
+                        "type": "thinking",
+                        "thinking": "Private reasoning.",
+                        "signature": encrypted_reasoning_signature("gAAAA_turn_one"),
+                    }
+                ],
+            }
+        ]
+        result = _translate_messages(messages)
+        assert result == [
+            {
+                "type": "reasoning",
+                "summary": [{"type": "summary_text", "text": "Private reasoning."}],
+                "encrypted_content": "gAAAA_turn_one",
+            }
+        ]
+
+    def test_redacted_thinking_with_encrypted_data_replays_the_encrypted_content(self):
+        messages = [
+            {
+                "role": "assistant",
+                "content": [{"type": "redacted_thinking", "data": encrypted_reasoning_signature("gAAAA_turn_one")}],
+            }
+        ]
+        result = _translate_messages(messages)
+        assert result == [{"type": "reasoning", "summary": [], "encrypted_content": "gAAAA_turn_one"}]
+
+    def test_each_encrypted_thinking_block_stays_its_own_reasoning_item(self):
+        """Two upstream items must not be merged into one, or the encrypted content of one is lost."""
+        messages = [
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "thinking", "thinking": "First.", "signature": encrypted_reasoning_signature("gAAAA_1")},
+                    {"type": "thinking", "thinking": "Second.", "signature": encrypted_reasoning_signature("gAAAA_2")},
+                ],
+            }
+        ]
+        result = _translate_messages(messages)
+        assert [item["encrypted_content"] for item in result] == ["gAAAA_1", "gAAAA_2"]
+
+    def test_anthropic_signed_thinking_block_replays_as_a_summary_only_item(self):
+        """A real Anthropic signature is opaque here, so it never masquerades as encrypted content."""
+        messages = [
+            {
+                "role": "assistant",
+                "content": [{"type": "thinking", "thinking": "Private reasoning.", "signature": "ErcBCkgIValid"}],
+            }
+        ]
+        result = _translate_messages(messages)
+        assert result == [
+            {"type": "reasoning", "summary": [{"type": "summary_text", "text": "Private reasoning."}]}
+        ]
+
     def test_consecutive_thinking_blocks_become_one_reasoning_item(self):
         """Summary parts of one upstream reasoning item are regrouped into that item."""
         messages = [
@@ -1102,6 +1163,23 @@ class TestTranslateRequestBroaderCoverage:
         kwargs = _ADAPTER.translate_request(req)
         assert "reasoning" not in kwargs
 
+    def test_thinking_asks_for_the_encrypted_reasoning(self):
+        """The documented way to get reasoning that survives store=false is to ask for it."""
+        req = _make_request(thinking={"type": "enabled", "budget_tokens": 12000})
+        kwargs = _ADAPTER.translate_request(req)
+        assert kwargs["include"] == ["reasoning.encrypted_content"]
+
+    def test_encrypted_reasoning_is_asked_for_without_a_thinking_block(self):
+        """A reasoning model reasons whether or not the client sent `thinking`, so the replay needs it either way."""
+        kwargs = _ADAPTER.translate_request(_make_request())
+        assert kwargs["include"] == ["reasoning.encrypted_content"]
+
+    def test_encrypted_reasoning_is_not_asked_for_when_the_provider_rejects_include(self):
+        req = _make_request(thinking={"type": "enabled", "budget_tokens": 12000})
+        kwargs = _ADAPTER.translate_request(req, include_encrypted_reasoning=False)
+        assert kwargs["reasoning"] == {"effort": "high"}
+        assert "include" not in kwargs
+
     def test_metadata_user_id_mapped_to_user(self):
         req = _make_request(metadata={"user_id": "user-42"})
         kwargs = _ADAPTER.translate_request(req)
@@ -1246,7 +1324,9 @@ def _make_function_call_item(call_id: str, name: str, arguments: str) -> MagicMo
     return item
 
 
-def _make_reasoning_item(summaries: List[str], item_id: str = "rs_test_1") -> MagicMock:
+def _make_reasoning_item(
+    summaries: List[str], item_id: str = "rs_test_1", encrypted_content: str | None = None
+) -> MagicMock:
     """Build a mock ResponseReasoningItem."""
     from openai.types.responses import ResponseReasoningItem  # type: ignore[import]
 
@@ -1259,9 +1339,13 @@ def _make_reasoning_item(summaries: List[str], item_id: str = "rs_test_1") -> Ma
     item = MagicMock(spec=ResponseReasoningItem)
     item.id = item_id
     item.summary = summary_mocks
+    item.encrypted_content = encrypted_content
     return item
 
 
+_ENCRYPTED_REASONING = "gAAAAABp_encrypted_reasoning_bytes_only_openai_can_read"
+
+
 class TestTranslateResponse:
     """Responses API -> AnthropicMessagesResponse conversion."""
 
@@ -1386,7 +1470,81 @@ class TestTranslateResponse:
         reasoning = _make_reasoning_item(["Part one.", "Part two."], item_id="rs_abc123")
         response = _make_mock_response(output=[reasoning])
         result: Any = _ADAPTER.translate_response(response)
-        assert [block["signature"] for block in result["content"]] == [None, None]
+        assert [block["signature"] for block in result["content"]] == [None]
+        assert "rs_abc123" not in json.dumps(result["content"])
+
+    def test_summary_parts_join_into_one_thinking_block(self):
+        """One reasoning item is one block, so its signature is echoed back exactly once."""
+        reasoning = _make_reasoning_item(["Part one.", "Part two."])
+        response = _make_mock_response(output=[reasoning])
+        result: Any = _ADAPTER.translate_response(response)
+        assert [block["thinking"] for block in result["content"]] == ["Part one.\n\nPart two."]
+
+    def test_encrypted_content_rides_the_thinking_signature(self):
+        """Regression for https://github.com/BerriAI/litellm/issues/40288 (outbound fault site)."""
+        reasoning = _make_reasoning_item(["Part one."], item_id="rs_abc123", encrypted_content=_ENCRYPTED_REASONING)
+        response = _make_mock_response(output=[reasoning])
+        result: Any = _ADAPTER.translate_response(response)
+        assert result["content"] == [
+            {
+                "type": "thinking",
+                "thinking": "Part one.",
+                "signature": encrypted_reasoning_signature(_ENCRYPTED_REASONING),
+            }
+        ]
+
+    def test_reasoning_without_summary_becomes_redacted_thinking(self):
+        """With summaries off the encrypted reasoning still has to reach the client to be replayed."""
+        reasoning = _make_reasoning_item([], encrypted_content=_ENCRYPTED_REASONING)
+        response = _make_mock_response(output=[reasoning])
+        result: Any = _ADAPTER.translate_response(response)
+        assert result["content"] == [
+            {"type": "redacted_thinking", "data": encrypted_reasoning_signature(_ENCRYPTED_REASONING)}
+        ]
+
+    def test_dict_reasoning_item_carries_its_encrypted_content(self):
+        response = _make_mock_response(
+            output=[
+                {
+                    "type": "reasoning",
+                    "id": "rs_dict_1",
+                    "encrypted_content": _ENCRYPTED_REASONING,
+                    "summary": [{"type": "summary_text", "text": "Weighing the options."}],
+                }
+            ]
+        )
+        result: Any = _ADAPTER.translate_response(response)
+        assert result["content"][0]["signature"] == encrypted_reasoning_signature(_ENCRYPTED_REASONING)
+
+    def test_reasoning_item_round_trip_is_byte_stable(self):
+        """Regression for https://github.com/BerriAI/litellm/issues/40288.
+
+        The reasoning item the next turn replays must be the one OpenAI produced, with its
+        encrypted reasoning intact, and identical on every later turn so the prompt cache
+        prefix keeps matching.
+        """
+        reasoning = _make_reasoning_item(["Part one.", "Part two."], encrypted_content=_ENCRYPTED_REASONING)
+        turn: Any = _ADAPTER.translate_response(_make_mock_response(output=[reasoning]))
+        history = [{"role": "assistant", "content": turn["content"]}]
+
+        replayed_items = [_translate_messages(history) for _ in range(2)]
+
+        assert replayed_items[0] == replayed_items[1]
+        assert replayed_items[0] == [
+            {
+                "type": "reasoning",
+                "summary": [{"type": "summary_text", "text": "Part one.\n\nPart two."}],
+                "encrypted_content": _ENCRYPTED_REASONING,
+            }
+        ]
+
+    def test_redacted_reasoning_round_trip_replays_the_encrypted_content(self):
+        reasoning = _make_reasoning_item([], encrypted_content=_ENCRYPTED_REASONING)
+        turn: Any = _ADAPTER.translate_response(_make_mock_response(output=[reasoning]))
+
+        replayed = _translate_messages([{"role": "assistant", "content": turn["content"]}])
+
+        assert replayed == [{"type": "reasoning", "summary": [], "encrypted_content": _ENCRYPTED_REASONING}]
 
     def test_dict_reasoning_item_becomes_thinking_block(self):
         """A reasoning item arriving as a plain dict is kept, not dropped."""
@@ -1402,14 +1560,26 @@ class TestTranslateResponse:
         result: Any = _ADAPTER.translate_response(response)
         assert result["content"] == [{"type": "thinking", "thinking": "Weighing the options.", "signature": None}]
 
-    def test_thinking_blocks_are_dropped_when_replayed_to_anthropic(self):
+    @pytest.mark.parametrize(
+        ("summaries", "encrypted_content"),
+        [
+            (["Part one."], None),
+            (["Part one."], _ENCRYPTED_REASONING),
+            ([], _ENCRYPTED_REASONING),
+        ],
+        ids=["unsigned_thinking", "encrypted_thinking", "encrypted_redacted_thinking"],
+    )
+    def test_thinking_blocks_are_dropped_when_replayed_to_anthropic(self, summaries, encrypted_content):
         """Replaying this turn to an Anthropic model must not send a signature it cannot verify."""
         from litellm.litellm_core_utils.prompt_templates.factory import (
             _drop_unsignable_thinking_blocks,
         )
 
-        response = _make_mock_response(output=[_make_reasoning_item(["Part one."], item_id="rs_abc123")])
+        response = _make_mock_response(
+            output=[_make_reasoning_item(summaries, item_id="rs_abc123", encrypted_content=encrypted_content)]
+        )
         result: Any = _ADAPTER.translate_response(response)
+        assert len(result["content"]) == 1
         assert _drop_unsignable_thinking_blocks(result["content"]) == []
 
     def test_usage_mapped_correctly(self):
diff --git a/tests/test_litellm/llms/anthropic/test_anthropic_common_utils.py b/tests/test_litellm/llms/anthropic/test_anthropic_common_utils.py
index ae620fdd6dc..e1b39c4ba13 100644
--- a/tests/test_litellm/llms/anthropic/test_anthropic_common_utils.py
+++ b/tests/test_litellm/llms/anthropic/test_anthropic_common_utils.py
@@ -42,12 +42,15 @@ FAKE_AUTH_TOKEN = "sk-ant-aut01-fake-auth-token-for-testing-123456789"
 def test_is_claude_code_one_shot_subagent_request(messages, system, expected):
     from litellm.llms.anthropic.common_utils import is_claude_code_one_shot_subagent_request
 
-    assert is_claude_code_one_shot_subagent_request(
-        messages=messages,
-        system=system,
-        tools=None,
-        user_agent="claude-cli/2.1.263 (external, cli)",
-    ) is expected
+    assert (
+        is_claude_code_one_shot_subagent_request(
+            messages=messages,
+            system=system,
+            tools=None,
+            user_agent="claude-cli/2.1.263 (external, cli)",
+        )
+        is expected
+    )
 
 
 class TestOptionallyHandleAnthropicOAuth:
@@ -1541,6 +1544,71 @@ class TestAnthropicThinkingSignatureSelfHeal:
         out = strip_empty_content_blocks_from_anthropic_messages(msgs)
         assert [b["type"] for b in out[0]["content"]] == ["thinking"]
 
+    def test_strip_keeps_encrypted_reasoning_blocks_for_the_responses_bridge(self):
+        """The /v1/messages handler runs this before dispatch, so the bridge must still see the replay."""
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            encrypted_reasoning_signature,
+        )
+        from litellm.llms.anthropic.common_utils import (
+            strip_empty_content_blocks_from_anthropic_messages,
+        )
+
+        msgs = [
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "thinking", "thinking": "plan", "signature": encrypted_reasoning_signature("gAAAA_1")},
+                    {"type": "redacted_thinking", "data": encrypted_reasoning_signature("gAAAA_2")},
+                    {"type": "text", "text": "The answer."},
+                ],
+            }
+        ]
+        assert strip_empty_content_blocks_from_anthropic_messages(msgs) == msgs
+
+    def test_strip_encrypted_reasoning_drops_only_the_bridge_tagged_blocks(self):
+        """A session resumed on an Anthropic model replays reasoning only OpenAI can verify."""
+        from litellm.litellm_core_utils.prompt_templates.common_utils import (
+            encrypted_reasoning_signature,
+        )
+        from litellm.llms.anthropic.common_utils import (
+            strip_encrypted_reasoning_blocks_from_anthropic_messages,
+        )
+
+        msgs = [
+            {"role": "user", "content": "Solve it."},
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "thinking", "thinking": "plan", "signature": encrypted_reasoning_signature("gAAAA_1")},
+                    {"type": "redacted_thinking", "data": encrypted_reasoning_signature("gAAAA_2")},
+                ],
+            },
+            {
+                "role": "assistant",
+                "content": [
+                    {"type": "thinking", "thinking": "plan", "signature": encrypted_reasoning_signature("gAAAA_3")},
+                    {"type": "thinking", "thinking": "native", "signature": "EqQBCkYIAxgCIkA_anthropic_signed"},
+                    {"type": "redacted_thinking", "data": "EmwKAhgBEgy_anthropic_minted"},
+                    {"type": "text", "text": "The answer."},
+                ],
+            },
+        ]
+        out = strip_encrypted_reasoning_blocks_from_anthropic_messages(msgs)
+        assert [m["role"] for m in out] == ["user", "assistant"]
+        assert [b["type"] for b in out[1]["content"]] == ["thinking", "redacted_thinking", "text"]
+        assert out[1]["content"][0]["signature"] == "EqQBCkYIAxgCIkA_anthropic_signed"
+        assert len(msgs[1]["content"]) == 2
+        assert len(msgs[2]["content"]) == 4
+
+    def test_strip_encrypted_reasoning_leaves_malformed_messages_for_the_provider_to_reject(self):
+        """A bare string in messages must reach Anthropic as a 400, not die in the stripper as a 500."""
+        from litellm.llms.anthropic.common_utils import (
+            strip_encrypted_reasoning_blocks_from_anthropic_messages,
+        )
+
+        msgs = ["hi", {"role": "user", "content": "hello"}]
+        assert strip_encrypted_reasoning_blocks_from_anthropic_messages(msgs) == msgs
+
     def test_strip_empty_text_blocks_treats_null_text_as_empty(self):
         from litellm.llms.anthropic.common_utils import (
             strip_empty_content_blocks_from_anthropic_messages,
@@ -2199,3 +2267,25 @@ def test_create_anthropic_model_list_response_empty():
     assert response["has_more"] is False
     assert response["first_id"] is None
     assert response["last_id"] is None
+
+
+def test_create_anthropic_model_list_response_lists_ids_as_told():
+    """listed_ids renames an entry for the caller while display_name and every other field stay keyed to the served
+    id, and the envelope's first/last ids follow the renamed entries."""
+    from litellm.llms.anthropic.common_utils import (
+        create_anthropic_model_list_response,
+    )
+
+    response = create_anthropic_model_list_response(
+        [
+            {"id": "gpt-4o", "object": "model", "created": 0, "owned_by": "openai", "max_input_tokens": 1000000},
+            {"id": "claude-haiku-4-5", "object": "model", "created": 0, "owned_by": "openai"},
+        ],
+        display_names={"gpt-4o": "GPT 4o"},
+        listed_ids={"gpt-4o": "claude-router-gpt-4o[1m]"},
+    )
+
+    gpt, haiku = response["data"]
+    assert (gpt["id"], gpt["display_name"], gpt["max_input_tokens"]) == ("claude-router-gpt-4o[1m]", "GPT 4o", 1000000)
+    assert (haiku["id"], haiku["display_name"]) == ("claude-haiku-4-5", "claude-haiku-4-5")
+    assert (response["first_id"], response["last_id"]) == ("claude-router-gpt-4o[1m]", "claude-haiku-4-5")
diff --git a/tests/test_litellm/llms/azure/chat/test_azure_chat_gpt_transformation.py b/tests/test_litellm/llms/azure/chat/test_azure_chat_gpt_transformation.py
index 4e6b9ed0188..bc6cb0c0fed 100644
--- a/tests/test_litellm/llms/azure/chat/test_azure_chat_gpt_transformation.py
+++ b/tests/test_litellm/llms/azure/chat/test_azure_chat_gpt_transformation.py
@@ -198,6 +198,9 @@ def test_azure_gpt_5_takes_the_reasoning_path() -> None:
     assert "reasoning_effort" in supported
 
 
+_ARTIFACT_FIELD_PATTERN: Final = r'^(?!__.*__$)[^\p{Cc}\p{Cf}\p{Zl}\p{Zp}"\\./[\]]{1,200}$'
+
+
 class TestAzureToolSchemaCombinatorFlattening:
     """
     Regression tests for LIT-6510: Azure's chat completions validator rejects
@@ -259,6 +262,26 @@ class TestAzureToolSchemaCombinatorFlattening:
         self._transform(AzureOpenAIConfig(), "gpt-4o", [tool])
         assert tool == self._anyof_tool()
 
+    def test_transform_request_drops_non_python_regex_pattern(self):
+        tool = {
+            "type": "function",
+            "function": {
+                "name": "Artifact",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"field": {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN}},
+                },
+            },
+        }
+
+        request = self._transform(AzureOpenAIConfig(), "gpt-4o", [tool])
+
+        assert request["tools"][0]["function"]["parameters"] == {
+            "type": "object",
+            "properties": {"field": {"type": "string"}},
+        }
+        assert tool["function"]["parameters"]["properties"]["field"]["pattern"] == _ARTIFACT_FIELD_PATTERN
+
     def test_clean_object_schema_passes_through_as_same_object(self):
         tool = {
             "type": "function",
diff --git a/tests/test_litellm/llms/azure/passthrough/test_azure_passthrough_transformation.py b/tests/test_litellm/llms/azure/passthrough/test_azure_passthrough_transformation.py
index 29b74c2ee4a..c7e86616ee2 100644
--- a/tests/test_litellm/llms/azure/passthrough/test_azure_passthrough_transformation.py
+++ b/tests/test_litellm/llms/azure/passthrough/test_azure_passthrough_transformation.py
@@ -1,11 +1,20 @@
 import json
+from datetime import datetime
 from unittest.mock import MagicMock
 
 import httpx
+import pytest
 
-
-from litellm.llms.azure.passthrough.transformation import AzurePassthroughConfig
-from litellm.types.utils import ModelResponse
+import litellm
+from litellm.litellm_core_utils.litellm_logging import Logging
+from litellm.litellm_core_utils.token_counter import high_detail_image_token_upper_bound
+from litellm.llms.azure.passthrough.transformation import (
+    AzurePassthroughConfig,
+    azure_router_model_in_endpoint,
+    foreign_azure_deployment,
+)
+from litellm.types.llms.openai import ResponseCompletedEvent, ResponsesAPIResponse
+from litellm.types.utils import EmbeddingResponse, ModelResponse
 
 
 def _azure_chat_completion_body():
@@ -73,22 +82,408 @@ def test_azure_passthrough_logging_non_streaming_response_chat_completions():
     assert result.usage.total_tokens == 18
 
 
-def test_azure_passthrough_logging_non_streaming_response_unknown_endpoint_returns_none():
-    """
-    Endpoints other than chat/completions (responses, messages, images) fall
-    through to None — matches base-class behavior and Bedrock's "unknown
-    endpoint" handling. Not a regression; just scoping.
-    """
-    config = AzurePassthroughConfig()
-    logging_obj = MagicMock()
-
-    result = config.logging_non_streaming_response(
-        model="gpt-4.1-mini",
+def _relay_logging_obj(model: str) -> Logging:
+    logging_obj = Logging(
+        model=model,
+        messages=[],
+        stream=False,
+        call_type="allm_passthrough_route",
+        start_time=datetime.now(),
+        litellm_call_id="call-1",
+        function_id="fn-1",
+    )
+    logging_obj.update_environment_variables(
+        model=model,
+        litellm_params={"api_base": "https://my-resource.openai.azure.com", "custom_llm_provider": "azure"},
+        optional_params={},
         custom_llm_provider="azure",
-        httpx_response=_make_httpx_response(_azure_chat_completion_body()),
+    )
+    return logging_obj
+
+
+def _relay_logging_result(model: str, endpoint: str, body, status_code: int = 200):
+    logging_obj = _relay_logging_obj(model)
+    response = httpx.Response(
+        status_code=status_code,
+        headers={"content-type": "application/json"},
+        content=json.dumps(body).encode("utf-8"),
+        request=httpx.Request(
+            "POST", f"https://my-resource.openai.azure.com/{endpoint}?api-version=2025-04-01-preview"
+        ),
+    )
+    result = AzurePassthroughConfig().logging_non_streaming_response(
+        model=model,
+        custom_llm_provider="azure",
+        httpx_response=response,
         request_data={},
         logging_obj=logging_obj,
-        endpoint="openai/responses",
+        endpoint=endpoint,
+    )
+    return result, logging_obj
+
+
+EMBEDDINGS_BODY = {
+    "object": "list",
+    "data": [{"object": "embedding", "index": 0, "embedding": [0.1, 0.2]}],
+    "model": "text-embedding-3-small",
+    "usage": {"prompt_tokens": 1000, "total_tokens": 1000},
+}
+
+RESPONSES_BODY = {
+    "id": "resp_1",
+    "object": "response",
+    "created_at": 1,
+    "status": "completed",
+    "model": "gpt-4.1-mini",
+    "output": [
+        {
+            "type": "message",
+            "id": "msg_1",
+            "role": "assistant",
+            "status": "completed",
+            "content": [{"type": "output_text", "text": "hi", "annotations": []}],
+        }
+    ],
+    "usage": {"input_tokens": 1000, "output_tokens": 100, "total_tokens": 1100},
+}
+
+
+def test_azure_passthrough_embeddings_relay_is_costed_per_input_token():
+    result, logging_obj = _relay_logging_result(
+        "text-embedding-3-small", "openai/deployments/text-embedding-3-small/embeddings", EMBEDDINGS_BODY
+    )
+    per_token = litellm.get_model_info("azure/text-embedding-3-small")["input_cost_per_token"]
+
+    assert isinstance(result, EmbeddingResponse)
+    assert logging_obj.call_type == "aembedding"
+    assert per_token > 0
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(1000 * per_token)
+
+
+def test_azure_passthrough_responses_relay_is_costed_per_token():
+    result, logging_obj = _relay_logging_result("gpt-4.1-mini", "openai/responses", RESPONSES_BODY)
+    info = litellm.get_model_info("azure/gpt-4.1-mini")
+
+    assert isinstance(result, ResponsesAPIResponse)
+    assert logging_obj.call_type == "aresponses"
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(
+        1000 * info["input_cost_per_token"] + 100 * info["output_cost_per_token"]
+    )
+
+
+def test_azure_passthrough_failed_embeddings_relay_is_not_costed():
+    result, logging_obj = _relay_logging_result(
+        "text-embedding-3-small",
+        "openai/deployments/text-embedding-3-small/embeddings",
+        {"error": {"code": "429", "message": "rate limited"}},
+        status_code=429,
     )
 
     assert result is None
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+def test_azure_passthrough_logging_non_streaming_response_unknown_endpoint_returns_none():
+    result, logging_obj = _relay_logging_result(
+        "gpt-4o-mini-tts", "openai/deployments/gpt-4o-mini-tts/audio/speech", {"audio": "..."}
+    )
+
+    assert result is None
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+def _sse_line(payload: dict) -> str:
+    return "data: " + json.dumps(payload)
+
+
+def _azure_chat_completion_chunks() -> list[str]:
+    head = {"id": "chatcmpl-abc123", "object": "chat.completion.chunk", "created": 1700000000, "model": "gpt-4.1-mini"}
+    return [
+        _sse_line(
+            {
+                **head,
+                "choices": [{"index": 0, "delta": {"role": "assistant", "content": "Hello!"}, "finish_reason": None}],
+            }
+        ),
+        _sse_line(
+            {**head, "choices": [{"index": 0, "delta": {"content": " How can I assist?"}, "finish_reason": None}]}
+        ),
+        _sse_line({**head, "choices": [{"index": 0, "delta": {}, "finish_reason": "stop"}]}),
+        _sse_line({**head, "choices": [], "usage": {"prompt_tokens": 10, "completion_tokens": 8, "total_tokens": 18}}),
+        "data: [DONE]",
+    ]
+
+
+def test_azure_passthrough_streaming_chat_chunks_build_the_complete_response():
+    response = AzurePassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=_azure_chat_completion_chunks(),
+        litellm_logging_obj=MagicMock(),
+        model="gpt-4.1-mini",
+        custom_llm_provider="azure",
+        endpoint="openai/deployments/gpt-4.1-mini/chat/completions",
+    )
+
+    assert isinstance(response, ModelResponse)
+    assert response.choices[0].message.content == "Hello! How can I assist?"
+    assert response.usage.prompt_tokens == 10
+    assert response.usage.completion_tokens == 8
+
+
+def test_azure_passthrough_streaming_chunks_without_usage_count_prompt_tokens_from_the_relayed_request():
+    messages = [{"role": "user", "content": "Say hi in three words"}]
+    logging_obj = MagicMock()
+    logging_obj.model_call_details = {"request_data": {"messages": messages, "stream": True}}
+
+    response = AzurePassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=[chunk for chunk in _azure_chat_completion_chunks() if '"usage"' not in chunk],
+        litellm_logging_obj=logging_obj,
+        model="gpt-4.1-mini",
+        custom_llm_provider="azure",
+        endpoint="openai/deployments/gpt-4.1-mini/chat/completions",
+    )
+
+    assert isinstance(response, ModelResponse)
+    assert response.choices[0].message.content == "Hello! How can I assist?"
+    assert response.usage.prompt_tokens > 0
+    assert response.usage.prompt_tokens == litellm.token_counter(model="gpt-4.1-mini", messages=messages)
+    assert response.usage.completion_tokens > 0
+
+
+def test_azure_passthrough_streaming_chunks_count_remote_image_prompt_tokens_without_fetching_the_image():
+    messages = [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Describe this"},
+                {"type": "image_url", "image_url": {"url": "http://127.0.0.1:9/doc.png", "detail": "high"}},
+            ],
+        }
+    ]
+    logging_obj = MagicMock()
+    logging_obj.model_call_details = {"request_data": {"messages": messages, "stream": True}}
+
+    response = AzurePassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=[chunk for chunk in _azure_chat_completion_chunks() if '"usage"' not in chunk],
+        litellm_logging_obj=logging_obj,
+        model="gpt-4.1-mini",
+        custom_llm_provider="azure",
+        endpoint="openai/deployments/gpt-4.1-mini/chat/completions",
+    )
+
+    text_only_messages = [{"role": "user", "content": [{"type": "text", "text": "Describe this"}]}]
+    assert isinstance(response, ModelResponse)
+    assert response.usage.prompt_tokens == (
+        litellm.token_counter(model="gpt-4.1-mini", messages=text_only_messages) + high_detail_image_token_upper_bound()
+    )
+
+
+def test_azure_passthrough_streaming_chunks_for_unknown_endpoint_return_none():
+    response = AzurePassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=_azure_chat_completion_chunks(),
+        litellm_logging_obj=MagicMock(),
+        model="gpt-4.1-mini",
+        custom_llm_provider="azure",
+        endpoint="openai/deployments/gpt-4.1-mini/embeddings",
+    )
+
+    assert response is None
+
+
+def _azure_responses_stream_chunks(terminal_event: str | None = "response.completed") -> list[str]:
+    in_progress = {**RESPONSES_BODY, "status": "in_progress", "output": [], "usage": None}
+    events = [
+        ("response.created", {"type": "response.created", "sequence_number": 0, "response": in_progress}),
+        (
+            "response.output_text.delta",
+            {"type": "response.output_text.delta", "sequence_number": 1, "item_id": "msg_1", "delta": "hi"},
+        ),
+    ] + (
+        [(terminal_event, {"type": terminal_event, "sequence_number": 2, "response": RESPONSES_BODY})]
+        if terminal_event
+        else []
+    )
+    return [line for name, payload in events for line in (f"event: {name}", _sse_line(payload))]
+
+
+def test_azure_passthrough_streaming_responses_chunks_are_costed_per_token():
+    logging_obj = _relay_logging_obj("gpt-4.1-mini")
+
+    response = AzurePassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=_azure_responses_stream_chunks(),
+        litellm_logging_obj=logging_obj,
+        model="gpt-4.1-mini",
+        custom_llm_provider="azure",
+        endpoint="openai/responses",
+    )
+    info = litellm.get_model_info("azure/gpt-4.1-mini")
+
+    assert isinstance(response, ResponseCompletedEvent)
+    assert response.response.usage.input_tokens == 1000
+    assert logging_obj.call_type == "aresponses"
+    assert logging_obj._response_cost_calculator(result=response.response) == pytest.approx(
+        1000 * info["input_cost_per_token"] + 100 * info["output_cost_per_token"]
+    )
+
+
+def test_azure_passthrough_streaming_responses_without_a_terminal_event_are_not_costed():
+    logging_obj = _relay_logging_obj("gpt-4.1-mini")
+
+    response = AzurePassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=_azure_responses_stream_chunks(terminal_event=None),
+        litellm_logging_obj=logging_obj,
+        model="gpt-4.1-mini",
+        custom_llm_provider="azure",
+        endpoint="openai/responses",
+    )
+
+    assert response is None
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+def _complete_url(request_query_params: dict, litellm_params: dict) -> httpx.URL:
+    url, _ = AzurePassthroughConfig().get_complete_url(
+        api_base="https://my-resource.openai.azure.com",
+        api_key="key",
+        model="gpt-4.1-mini",
+        endpoint="openai/deployments/gpt-4.1-mini/chat/completions",
+        request_query_params=request_query_params,
+        litellm_params=litellm_params,
+    )
+    return url
+
+
+def test_azure_passthrough_url_forwards_the_callers_api_version():
+    url = _complete_url(request_query_params={"api-version": "2025-04-01-preview"}, litellm_params={})
+
+    assert url.path == "/openai/deployments/gpt-4.1-mini/chat/completions"
+    assert url.params["api-version"] == "2025-04-01-preview"
+
+
+def test_azure_passthrough_url_prefers_the_callers_api_version_over_the_deployments():
+    url = _complete_url(
+        request_query_params={"api-version": "2025-04-01-preview"}, litellm_params={"api_version": "2024-10-21"}
+    )
+
+    assert url.params["api-version"] == "2025-04-01-preview"
+
+
+def test_azure_passthrough_url_fills_in_the_deployments_api_version_when_the_caller_sends_none():
+    url = _complete_url(request_query_params={}, litellm_params={"api_version": "2024-10-21"})
+
+    assert url.params["api-version"] == "2024-10-21"
+
+
+FULL_URL_API_BASE = (
+    "https://my-resource.openai.azure.com/openai/deployments/gpt-4.1-mini/chat/completions?api-version=2024-10-21"
+)
+
+
+def _full_url_complete_url(request_query_params: dict) -> httpx.URL:
+    url, _ = AzurePassthroughConfig().get_complete_url(
+        api_base=FULL_URL_API_BASE,
+        api_key="key",
+        model="gpt-4.1-mini",
+        endpoint="chat/completions",
+        request_query_params=request_query_params,
+        litellm_params={},
+    )
+    return url
+
+
+def test_azure_passthrough_url_prefers_the_callers_api_version_over_a_full_url_api_bases():
+    url = _full_url_complete_url(request_query_params={"api-version": "2025-04-01-preview"})
+
+    assert str(url) == (
+        "https://my-resource.openai.azure.com/openai/deployments/gpt-4.1-mini/chat/completions"
+        "?api-version=2025-04-01-preview"
+    )
+
+
+def test_azure_passthrough_url_keeps_a_full_url_api_bases_api_version_when_the_caller_sends_none():
+    url = _full_url_complete_url(request_query_params={})
+
+    assert url.params["api-version"] == "2024-10-21"
+
+
+def test_azure_passthrough_url_strips_the_leading_router_model_segment():
+    url, _ = AzurePassthroughConfig().get_complete_url(
+        api_base="https://my-resource.openai.azure.com",
+        api_key="key",
+        model="gpt-4.1-mini",
+        endpoint="gpt-4.1-mini/openai/deployments/gpt-4.1-mini/chat/completions",
+        request_query_params={"api-version": "2024-10-21"},
+        litellm_params={},
+    )
+
+    assert (
+        str(url)
+        == "https://my-resource.openai.azure.com/openai/deployments/gpt-4.1-mini/chat/completions?api-version=2024-10-21"
+    )
+
+
+def test_azure_passthrough_url_rewrites_the_model_group_only_as_a_whole_segment():
+    url, _ = AzurePassthroughConfig().get_complete_url(
+        api_base="https://my-resource.openai.azure.com",
+        api_key="key",
+        model="gpt-4.1-mini",
+        endpoint="gpt/openai/deployments/gpt-4.1-mini/chat/completions",
+        request_query_params={"api-version": "2024-10-21"},
+        litellm_params={"litellm_metadata": {"model_group": "gpt"}},
+    )
+
+    assert (
+        str(url)
+        == "https://my-resource.openai.azure.com/openai/deployments/gpt-4.1-mini/chat/completions?api-version=2024-10-21"
+    )
+
+
+@pytest.mark.parametrize(
+    "request_data, expected",
+    [({"stream": True}, True), ({"stream": 1}, True), ({"stream": False}, False), ({}, False)],
+)
+def test_azure_passthrough_is_streaming_request_reads_the_stream_flag(request_data, expected):
+    assert (
+        AzurePassthroughConfig().is_streaming_request(
+            endpoint="openai/deployments/x/chat/completions", request_data=request_data
+        )
+        is expected
+    )
+
+
+@pytest.mark.parametrize(
+    "endpoint, expected",
+    [
+        ("gpt/openai/deployments/gpt/chat/completions", None),
+        ("openai/deployments/gpt/chat/completions", None),
+        ("gpt/openai/deployments/gpt-5.4-mini/chat/completions", None),
+        ("gpt/openai/deployments/GPT-5.4-MINI/chat/completions", None),
+        ("gpt/openai/deployments/Gpt/chat/completions", "Gpt"),
+        ("gpt/models/chat/completions", None),
+        ("gpt/openai/deployments/gpt-5.4/chat/completions", "gpt-5.4"),
+        ("gpt/openai/deployments/other-group/chat/completions", "other-group"),
+        ("openai/deployments/victim/gpt/chat/completions", "victim"),
+        ("gpt/openai/deployments/GPT-5.4/chat/completions", "GPT-5.4"),
+    ],
+)
+def test_foreign_azure_deployment_names_a_segment_outside_the_group(endpoint, expected):
+    assert foreign_azure_deployment(endpoint, "gpt", lambda: frozenset({"gpt-5.4-mini"})) == expected
+
+
+def test_foreign_azure_deployment_skips_the_router_when_the_segment_is_the_group_itself():
+    def served_models():
+        raise AssertionError("the router must not be consulted for the group's own name")
+
+    assert foreign_azure_deployment("gpt/openai/deployments/gpt/chat/completions", "gpt", served_models) is None
+
+
+@pytest.mark.parametrize(
+    "endpoint, expected",
+    [
+        ("other-group/openai/deployments/other-group/chat/completions", "other-group"),
+        ("openai/deployments/gpt/chat/completions", "gpt"),
+        ("openai/deployments/my-azure-deployment/chat/completions", None),
+        ("gpt", None),
+    ],
+)
+def test_azure_router_model_in_endpoint_picks_the_first_router_model_segment(endpoint, expected):
+    assert azure_router_model_in_endpoint(endpoint, frozenset({"gpt", "other-group"})) == expected
diff --git a/tests/test_litellm/llms/azure/response/test_azure_transformation.py b/tests/test_litellm/llms/azure/response/test_azure_transformation.py
index 0cac2705ab0..726c9f65681 100644
--- a/tests/test_litellm/llms/azure/response/test_azure_transformation.py
+++ b/tests/test_litellm/llms/azure/response/test_azure_transformation.py
@@ -1,4 +1,5 @@
 from copy import deepcopy
+from typing import Final
 from unittest.mock import MagicMock, patch
 
 import pytest
@@ -243,6 +244,9 @@ def test_provider_config_manager_o_series_selection():
     assert not isinstance(default_config, AzureOpenAIOSeriesResponsesAPIConfig)
 
 
+_ARTIFACT_FIELD_PATTERN: Final = r'^(?!__.*__$)[^\p{Cc}\p{Cf}\p{Zl}\p{Zp}"\\./[\]]{1,200}$'
+
+
 class TestAzureResponsesAPIConfig:
     def setup_method(self):
         self.config = AzureOpenAIResponsesAPIConfig()
@@ -599,6 +603,31 @@ class TestAzureResponsesAPIConfig:
         assert result["tools"][0] is tool
         assert "anyOf" in result["tools"][0]["parameters"]
 
+    def test_azure_drops_non_python_regex_pattern_while_keeping_gpt5_combinators(self):
+        tool = {
+            "type": "function",
+            "name": "Artifact",
+            "parameters": {
+                "type": "object",
+                "anyOf": [{"properties": {"field": {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN}}}],
+                "properties": {"field": {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN}},
+            },
+        }
+
+        result = self.config.transform_responses_api_request(
+            model="my-eastus-deployment",
+            input="hi",
+            response_api_optional_request_params={"tools": [tool]},
+            litellm_params=GenericLiteLLMParams(model_info={"base_model": "azure/gpt-5.4-mini"}),
+            headers={},
+        )
+
+        assert result["tools"][0]["parameters"] == {
+            "type": "object",
+            "anyOf": [{"properties": {"field": {"type": "string"}}}],
+            "properties": {"field": {"type": "string"}},
+        }
+
     def test_azure_keeps_combinators_for_unrecognized_deployment_without_base_model(self):
         tool = self._anyof_tool()
 
diff --git a/tests/test_litellm/llms/azure/test_audio_transcriptions.py b/tests/test_litellm/llms/azure/test_audio_transcriptions.py
new file mode 100644
index 00000000000..cd5fcbd85a9
--- /dev/null
+++ b/tests/test_litellm/llms/azure/test_audio_transcriptions.py
@@ -0,0 +1,61 @@
+import json
+from pathlib import Path
+from typing import Final
+
+import httpx
+import pytest
+from openai import AzureOpenAI
+
+import litellm
+from litellm.cost_calculator import completion_cost
+from litellm.litellm_core_utils.audio_utils.utils import calculate_request_duration
+
+AUDIO_FILE: Final = Path(__file__).parents[3] / "gettysburg.wav"
+WHISPER_COST_PER_SECOND: Final = 0.0001
+
+
+def _transcription_client() -> AzureOpenAI:
+    def handler(request: httpx.Request) -> httpx.Response:
+        return httpx.Response(200, json={"text": "Four score and seven years ago"})
+
+    return AzureOpenAI(
+        api_key="test-key",
+        api_version="2024-06-01",
+        azure_endpoint="https://example.cognitiveservices.azure.com",
+        http_client=httpx.Client(transport=httpx.MockTransport(handler)),
+    )
+
+
+def test_azure_ai_transcription_is_priced_at_the_azure_ai_entry():
+    with AUDIO_FILE.open("rb") as audio:
+        response = litellm.transcription(
+            model="azure_ai/whisper",
+            file=audio,
+            api_base="https://example.cognitiveservices.azure.com",
+            api_key="test-key",
+            api_version="2024-06-01",
+            client=_transcription_client(),
+        )
+    with AUDIO_FILE.open("rb") as audio:
+        duration = calculate_request_duration(audio)
+
+    assert duration is not None and duration > 0
+    assert response._hidden_params["custom_llm_provider"] == "azure_ai"
+    assert completion_cost(completion_response=response, call_type="transcription") == pytest.approx(
+        WHISPER_COST_PER_SECOND * duration
+    )
+
+
+def test_azure_transcription_keeps_the_azure_provider():
+    with AUDIO_FILE.open("rb") as audio:
+        response = litellm.transcription(
+            model="azure/whisper-1",
+            file=audio,
+            api_base="https://example.openai.azure.com",
+            api_key="test-key",
+            api_version="2024-06-01",
+            client=_transcription_client(),
+        )
+
+    assert response._hidden_params["custom_llm_provider"] == "azure"
+    assert json.loads(response.model_dump_json())["text"] == "Four score and seven years ago"
diff --git a/tests/test_litellm/llms/azure/test_azure_common_utils.py b/tests/test_litellm/llms/azure/test_azure_common_utils.py
index f000abb4c9a..c959c201ccb 100644
--- a/tests/test_litellm/llms/azure/test_azure_common_utils.py
+++ b/tests/test_litellm/llms/azure/test_azure_common_utils.py
@@ -385,6 +385,58 @@ def test_select_azure_base_url_called(setup_mocks):
     setup_mocks["select_url"].assert_called_once()
 
 
+def test_initialize_defaults_max_retries_to_litellm_default(setup_mocks):
+    result = BaseAzureLLM().initialize_azure_sdk_client(
+        litellm_params={},
+        api_key="test-api-key",
+        api_base="https://test.openai.azure.com",
+        model_name="gpt-4",
+        api_version="2023-06-01",
+        is_async=False,
+    )
+
+    assert result["max_retries"] == litellm.constants.DEFAULT_MAX_RETRIES
+
+
+@pytest.mark.parametrize(
+    "configured, expected",
+    [(0, 0), (5, 5), (None, litellm.constants.DEFAULT_MAX_RETRIES)],
+)
+def test_initialize_honors_explicit_max_retries(setup_mocks, configured, expected):
+    result = BaseAzureLLM().initialize_azure_sdk_client(
+        litellm_params={"max_retries": configured},
+        api_key="test-api-key",
+        api_base="https://test.openai.azure.com",
+        model_name="gpt-4",
+        api_version="2023-06-01",
+        is_async=False,
+    )
+
+    assert result["max_retries"] == expected
+
+
+def test_default_max_retries_env_var_reaches_azure_sdk_client():
+    import subprocess
+    import sys
+
+    code = (
+        "from litellm.llms.azure.common_utils import BaseAzureLLM\n"
+        "client = BaseAzureLLM().get_azure_openai_client("
+        "api_key='test-api-key', api_base='https://test.openai.azure.com', api_version='2024-02-01',"
+        " client=None, _is_async=True, litellm_params={}, model='gpt-4')\n"
+        "print(client.max_retries)"
+    )
+    completed = subprocess.run(
+        [sys.executable, "-c", code],
+        env={**os.environ, "DEFAULT_MAX_RETRIES": "0"},
+        capture_output=True,
+        text=True,
+        check=True,
+    )
+
+    assert completed.stdout.strip() == "0"
+
+
 @pytest.mark.parametrize(
     "call_type",
     [
diff --git a/tests/test_litellm/llms/azure_ai/image_edit/test_mai_image_edit_transformation.py b/tests/test_litellm/llms/azure_ai/image_edit/test_mai_image_edit_transformation.py
index 284a912d9a4..75e046825a3 100644
--- a/tests/test_litellm/llms/azure_ai/image_edit/test_mai_image_edit_transformation.py
+++ b/tests/test_litellm/llms/azure_ai/image_edit/test_mai_image_edit_transformation.py
@@ -6,6 +6,7 @@ import pytest
 
 
 import litellm
+from litellm.images.utils import ImageEditRequestUtils
 from litellm.llms.azure_ai.image_edit import (
     AzureFoundryMAIImageEditConfig,
     get_azure_ai_image_edit_config,
@@ -70,44 +71,48 @@ class TestAzureMAIImageEdit:
         assert "/mai/v1/images/edits" in url
         assert "api-version=preview" in url
 
-    def test_map_openai_params_keeps_size(self):
-        config = AzureFoundryMAIImageEditConfig()
-        optional_params = config.map_openai_params(
-            image_edit_optional_params={"size": "1792x1024", "n": 1},
+    def test_get_optional_params_image_edit_size_raises_400(self, monkeypatch):
+        monkeypatch.setattr(litellm, "drop_params", False)
+        with pytest.raises(litellm.UnsupportedParamsError, match="size") as exc_info:
+            ImageEditRequestUtils.get_optional_params_image_edit(
+                model="MAI-Image-2.5",
+                image_edit_provider_config=AzureFoundryMAIImageEditConfig(),
+                image_edit_optional_params={"size": "1024x1024", "n": 1},
+            )
+        assert exc_info.value.status_code == 400
+
+    def test_get_optional_params_image_edit_size_dropped_with_drop_params(self, monkeypatch):
+        monkeypatch.setattr(litellm, "drop_params", False)
+        optional_params = ImageEditRequestUtils.get_optional_params_image_edit(
             model="MAI-Image-2.5",
+            image_edit_provider_config=AzureFoundryMAIImageEditConfig(),
+            image_edit_optional_params={"size": "1024x1024", "n": 1},
             drop_params=True,
         )
-        assert optional_params["size"] == "1792x1024"
+        assert "size" not in optional_params
         assert optional_params["n"] == 1
-        assert "width" not in optional_params
-        assert "height" not in optional_params
 
-    def test_map_openai_params_defaults_size(self):
-        config = AzureFoundryMAIImageEditConfig()
-        optional_params = config.map_openai_params(
-            image_edit_optional_params={},
+    def test_get_optional_params_image_edit_without_size_forwards_nothing_extra(self, monkeypatch):
+        monkeypatch.setattr(litellm, "drop_params", False)
+        optional_params = ImageEditRequestUtils.get_optional_params_image_edit(
             model="MAI-Image-2.5",
-            drop_params=True,
+            image_edit_provider_config=AzureFoundryMAIImageEditConfig(),
+            image_edit_optional_params={},
         )
-        assert optional_params["size"] == "1024x1024"
+        assert optional_params == {}
 
-    def test_map_openai_params_unsupported_size_raises(self):
-        config = AzureFoundryMAIImageEditConfig()
-        with pytest.raises(ValueError, match="Unsupported size value: 'auto'"):
-            config.map_openai_params(
-                image_edit_optional_params={"size": "auto"},
-                model="MAI-Image-2.5",
-                drop_params=True,
-            )
-
-    def test_map_openai_params_invalid_size_format_raises(self):
-        config = AzureFoundryMAIImageEditConfig()
-        with pytest.raises(ValueError, match="Invalid size format: '1024xabc'"):
-            config.map_openai_params(
-                image_edit_optional_params={"size": "1024xabc"},
-                model="MAI-Image-2.5",
-                drop_params=True,
+    def test_image_edit_size_surfaces_as_400(self, monkeypatch):
+        monkeypatch.setattr(litellm, "drop_params", False)
+        with pytest.raises(litellm.BadRequestError) as exc_info:
+            litellm.image_edit(
+                model="azure_ai/MAI-Image-2.5",
+                image=io.BytesIO(b"fake-image-bytes"),
+                prompt="Turn this into a studio product shot",
+                size="1024x1024",
+                api_key="test-key",
+                api_base="https://my-resource.services.ai.azure.com",
             )
+        assert exc_info.value.status_code == 400
 
     def test_transform_image_edit_request_uses_image_field(self):
         config = AzureFoundryMAIImageEditConfig()
@@ -117,14 +122,14 @@ class TestAzureMAIImageEdit:
             model="MAI-Image-2.5",
             prompt="Turn this into a studio product shot",
             image=image_bytes,
-            image_edit_optional_request_params={"size": "1024x1024", "n": 1},
+            image_edit_optional_request_params={"n": 1},
             litellm_params={},
             headers={},
         )
 
         assert data["model"] == "MAI-Image-2.5"
         assert data["prompt"] == "Turn this into a studio product shot"
-        assert data["size"] == "1024x1024"
+        assert "size" not in data
         assert data["n"] == 1
         assert len(files) == 1
         assert files[0][0] == "image"
diff --git a/tests/test_litellm/llms/azure_ai/image_generation/test_mai_image_generation.py b/tests/test_litellm/llms/azure_ai/image_generation/test_mai_image_generation.py
index 9bdc79919d2..55656b97c57 100644
--- a/tests/test_litellm/llms/azure_ai/image_generation/test_mai_image_generation.py
+++ b/tests/test_litellm/llms/azure_ai/image_generation/test_mai_image_generation.py
@@ -3,8 +3,8 @@ from unittest.mock import MagicMock
 import httpx
 import pytest
 
-
 import litellm
+from litellm.exceptions import UnsupportedParamsError
 from litellm.llms.azure.azure import AzureChatCompletion
 from litellm.llms.azure.image_generation import get_azure_image_generation_config
 from litellm.llms.azure.image_generation.http_utils import (
@@ -29,9 +29,7 @@ from litellm.utils import get_optional_params_image_gen
 class TestAzureMAIImageGeneration:
     def test_is_mai_model(self):
         assert AzureFoundryMAIImageGenerationConfig.is_mai_model("MAI-Image-2.5")
-        assert AzureFoundryMAIImageGenerationConfig.is_mai_model(
-            "azure_ai/MAI-Image-2.5"
-        )
+        assert AzureFoundryMAIImageGenerationConfig.is_mai_model("azure_ai/MAI-Image-2.5")
         assert AzureFoundryMAIImageGenerationConfig.is_mai_model("MAI-Image-2.5-Flash")
         assert AzureFoundryMAIImageGenerationConfig.is_mai_model("MAI-Image-2e")
         assert not AzureFoundryMAIImageGenerationConfig.is_mai_model("flux.2-pro")
@@ -42,16 +40,10 @@ class TestAzureMAIImageGeneration:
             api_base="https://my-resource.services.ai.azure.com",
             api_version="preview",
         )
-        assert (
-            url
-            == "https://my-resource.services.ai.azure.com/mai/v1/images/generations?api-version=preview"
-        )
+        assert url == "https://my-resource.services.ai.azure.com/mai/v1/images/generations?api-version=preview"
 
     def test_get_mai_image_generation_url_preserves_full_path(self):
-        api = (
-            "https://my-resource.services.ai.azure.com/mai/v1/images/generations"
-            "?api-version=preview"
-        )
+        api = "https://my-resource.services.ai.azure.com/mai/v1/images/generations?api-version=preview"
         url = AzureFoundryMAIImageGenerationConfig.get_mai_image_generation_url(
             api_base=api,
             api_version="preview",
@@ -63,10 +55,7 @@ class TestAzureMAIImageGeneration:
             api_base="https://my-resource.services.ai.azure.com/mai/v1",
             api_version="preview",
         )
-        assert (
-            url
-            == "https://my-resource.services.ai.azure.com/mai/v1/images/generations?api-version=preview"
-        )
+        assert url == "https://my-resource.services.ai.azure.com/mai/v1/images/generations?api-version=preview"
 
     def test_get_azure_ai_image_generation_config_returns_mai(self):
         config = get_azure_ai_image_generation_config("MAI-Image-2.5")
@@ -104,13 +93,13 @@ class TestAzureMAIImageGeneration:
         config = AzureFoundryMAIImageGenerationConfig()
         optional_params = get_optional_params_image_gen(
             model="MAI-Image-2.5",
-            size="1792x1024",
+            size="1024x1024",
             n=1,
             custom_llm_provider="azure_ai",
             provider_config=config,
             drop_params=True,
         )
-        assert optional_params["width"] == 1792
+        assert optional_params["width"] == 1024
         assert optional_params["height"] == 1024
         assert "size" not in optional_params
 
@@ -127,10 +116,7 @@ class TestAzureMAIImageGeneration:
         assert "api-version=preview" in url
 
     def test_mai_json_body_keeps_model(self):
-        api = (
-            "https://my-resource.services.ai.azure.com/mai/v1/images/generations"
-            "?api-version=preview"
-        )
+        api = "https://my-resource.services.ai.azure.com/mai/v1/images/generations?api-version=preview"
         data = {
             "model": "MAI-Image-2.5",
             "prompt": "A photograph of a red fox",
@@ -176,7 +162,7 @@ class TestAzureMAIImageGeneration:
 
     def test_map_openai_params_unsupported_size_raises(self):
         config = AzureFoundryMAIImageGenerationConfig()
-        with pytest.raises(ValueError, match="Unsupported size value: 'auto'"):
+        with pytest.raises(UnsupportedParamsError, match="Unsupported size value: 'auto'"):
             config.map_openai_params(
                 non_default_params={"size": "auto"},
                 optional_params={},
@@ -186,7 +172,7 @@ class TestAzureMAIImageGeneration:
 
     def test_map_openai_params_invalid_custom_size_raises(self):
         config = AzureFoundryMAIImageGenerationConfig()
-        with pytest.raises(ValueError, match="Invalid size format: '1024xabc'"):
+        with pytest.raises(UnsupportedParamsError, match="Invalid size format: '1024xabc'"):
             config.map_openai_params(
                 non_default_params={"size": "1024xabc"},
                 optional_params={},
@@ -194,9 +180,138 @@ class TestAzureMAIImageGeneration:
                 drop_params=True,
             )
 
+    @pytest.mark.parametrize("size", ["512x512", "256x256", "700x1400"])
+    def test_map_openai_params_size_below_minimum_dimension_raises(self, size):
+        config = AzureFoundryMAIImageGenerationConfig()
+        with pytest.raises(UnsupportedParamsError, match="at least 768 pixels"):
+            config.map_openai_params(
+                non_default_params={"size": size},
+                optional_params={},
+                model="MAI-Image-2.5",
+                drop_params=True,
+            )
+
+    @pytest.mark.parametrize("size", ["1792x1024", "1024x1792"])
+    def test_map_openai_params_size_over_total_pixel_budget_raises(self, size):
+        config = AzureFoundryMAIImageGenerationConfig()
+        with pytest.raises(UnsupportedParamsError, match="at most 1056768 total pixels"):
+            config.map_openai_params(
+                non_default_params={"size": size},
+                optional_params={},
+                model="MAI-Image-2.5",
+                drop_params=True,
+            )
+
+    @pytest.mark.parametrize("size", ["1032x1024", "1376x768"])
+    def test_map_openai_params_size_at_live_pixel_cap_passes_through(self, size):
+        config = AzureFoundryMAIImageGenerationConfig()
+        optional_params = config.map_openai_params(
+            non_default_params={"size": size},
+            optional_params={},
+            model="MAI-Image-2.5",
+            drop_params=False,
+        )
+        assert optional_params["width"] * optional_params["height"] == 1_056_768
+
+    def test_map_openai_params_size_one_pixel_over_live_cap_raises(self):
+        config = AzureFoundryMAIImageGenerationConfig()
+        with pytest.raises(UnsupportedParamsError, match="at most 1056768 total pixels"):
+            config.map_openai_params(
+                non_default_params={"size": "1033x1024"},
+                optional_params={},
+                model="MAI-Image-2.5",
+                drop_params=False,
+            )
+
+    def test_map_openai_params_explicit_width_height_not_range_checked(self):
+        config = AzureFoundryMAIImageGenerationConfig()
+        optional_params = config.map_openai_params(
+            non_default_params={"width": 1792, "height": 1024},
+            optional_params={},
+            model="MAI-Image-2.5",
+            drop_params=True,
+        )
+        assert optional_params["width"] == 1792
+        assert optional_params["height"] == 1024
+
+    @pytest.mark.parametrize("n", [2, 4, "2", 0, -1])
+    def test_map_openai_params_n_other_than_one_raises(self, n):
+        config = AzureFoundryMAIImageGenerationConfig()
+        with pytest.raises(UnsupportedParamsError, match="returns exactly 1 image per request"):
+            config.map_openai_params(
+                non_default_params={"n": n},
+                optional_params={},
+                model="MAI-Image-2.5",
+                drop_params=False,
+            )
+
+    def test_map_openai_params_non_numeric_n_raises_400(self):
+        config = AzureFoundryMAIImageGenerationConfig()
+        with pytest.raises(UnsupportedParamsError, match="not a whole number of images") as exc_info:
+            config.map_openai_params(
+                non_default_params={"n": "abc"},
+                optional_params={},
+                model="MAI-Image-2.5",
+                drop_params=False,
+            )
+        assert exc_info.value.status_code == 400
+
+    def test_get_optional_params_image_gen_global_drop_params_drops_multi_image_n(self, monkeypatch):
+        monkeypatch.setattr(litellm, "drop_params", True)
+        optional_params = get_optional_params_image_gen(
+            model="MAI-Image-2.5",
+            n=4,
+            custom_llm_provider="azure_ai",
+            provider_config=AzureFoundryMAIImageGenerationConfig(),
+        )
+        assert "n" not in optional_params
+        assert optional_params["width"] == 1024
+
+    def test_get_optional_params_image_gen_without_any_drop_params_still_raises(self, monkeypatch):
+        monkeypatch.setattr(litellm, "drop_params", False)
+        with pytest.raises(UnsupportedParamsError, match="returns exactly 1 image per request"):
+            get_optional_params_image_gen(
+                model="MAI-Image-2.5",
+                n=4,
+                custom_llm_provider="azure_ai",
+                provider_config=AzureFoundryMAIImageGenerationConfig(),
+            )
+
+    def test_map_openai_params_multi_image_n_dropped_with_drop_params(self):
+        config = AzureFoundryMAIImageGenerationConfig()
+        optional_params = config.map_openai_params(
+            non_default_params={"n": 4},
+            optional_params={},
+            model="MAI-Image-2.5",
+            drop_params=True,
+        )
+        assert "n" not in optional_params
+
+    def test_map_openai_params_single_image_n_still_passes_through(self):
+        config = AzureFoundryMAIImageGenerationConfig()
+        optional_params = config.map_openai_params(
+            non_default_params={"n": 1},
+            optional_params={},
+            model="MAI-Image-2.5",
+            drop_params=False,
+        )
+        assert optional_params["n"] == 1
+
+    @pytest.mark.parametrize("params", [{"n": 2}, {"n": "abc"}, {"size": "512x512"}, {"size": "1792x1024"}])
+    def test_image_generation_rejected_params_surface_as_400(self, params):
+        with pytest.raises(litellm.BadRequestError) as exc_info:
+            litellm.image_generation(
+                model="azure_ai/MAI-Image-2.5",
+                prompt="A photograph of a red fox",
+                api_key="test-key",
+                api_base="https://my-resource.services.ai.azure.com",
+                **params,
+            )
+        assert exc_info.value.status_code == 400
+
     def test_map_openai_params_unsupported_param_raises(self):
         config = AzureFoundryMAIImageGenerationConfig()
-        with pytest.raises(ValueError, match="Parameter quality is not supported"):
+        with pytest.raises(UnsupportedParamsError, match="Parameter quality is not supported"):
             config.map_openai_params(
                 non_default_params={"quality": "hd"},
                 optional_params={},
@@ -343,16 +458,12 @@ class TestAzureMAIImageGeneration:
         litellm.model_cost = litellm.get_model_cost_map(url="")
         model = "azure_ai/MAI-Image-2.5"
         model_info = litellm.get_model_info(model=model, custom_llm_provider="azure_ai")
-        image_response = ImageResponse(
-            data=[ImageObject(b64_json="img1"), ImageObject(b64_json="img2")]
-        )
+        image_response = ImageResponse(data=[ImageObject(b64_json="img1"), ImageObject(b64_json="img2")])
 
         cost = azure_ai_image_cost_calculator(
             model=model,
             image_response=image_response,
         )
 
-        assert (
-            cost == len(image_response.data or []) * model_info["output_cost_per_image"]
-        )
+        assert cost == len(image_response.data or []) * model_info["output_cost_per_image"]
         assert cost > 0
diff --git a/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py b/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py
new file mode 100644
index 00000000000..c8007acf70f
--- /dev/null
+++ b/tests/test_litellm/llms/azure_ai/passthrough/test_azure_ai_passthrough_transformation.py
@@ -0,0 +1,617 @@
+import json
+from datetime import datetime
+from unittest.mock import MagicMock
+
+import httpx
+import pytest
+
+import litellm
+from litellm.integrations.custom_logger import CustomLogger
+from litellm.litellm_core_utils.litellm_logging import Logging
+from litellm.llms.azure_ai.passthrough.transformation import AzureAIPassthroughConfig
+from litellm.llms.base_llm.ocr.transformation import OCRResponse
+from litellm.types.rerank import RerankResponse
+from litellm.types.utils import EmbeddingResponse, ImageResponse, LlmProviders, ModelResponse
+from litellm.utils import ProviderConfigManager
+
+FOUNDRY_BASE = "https://my-resource.services.ai.azure.com"
+RESPONSES_COMPLETED_EVENT = {
+    "type": "response.completed",
+    "sequence_number": 2,
+    "response": {
+        "id": "resp_1",
+        "object": "response",
+        "created_at": 1,
+        "status": "completed",
+        "model": "gpt-5.4-mini",
+        "output": [
+            {
+                "type": "message",
+                "id": "msg_1",
+                "role": "assistant",
+                "status": "completed",
+                "content": [{"type": "output_text", "text": "hi", "annotations": []}],
+            }
+        ],
+        "usage": {"input_tokens": 1000, "output_tokens": 100, "total_tokens": 1100},
+    },
+}
+
+
+class _SpendProbe(CustomLogger):
+    logged_call_type: str | None = None
+    logged_cost: float | None = None
+
+    async def async_log_success_event(self, kwargs, response_obj, start_time, end_time):
+        self.logged_call_type = kwargs["call_type"]
+        self.logged_cost = kwargs["response_cost"]
+
+
+@pytest.fixture(autouse=True)
+def clear_azure_ai_env(monkeypatch):
+    for env_var in ("AZURE_AI_API_BASE", "AZURE_AI_API_KEY", "AZURE_AD_TOKEN", "AZURE_API_KEY"):
+        monkeypatch.delenv(env_var, raising=False)
+    monkeypatch.setattr(litellm, "api_base", None)
+    monkeypatch.setattr(litellm, "api_key", None)
+
+
+def test_provider_config_manager_resolves_azure_ai_passthrough_config():
+    config = ProviderConfigManager.get_provider_passthrough_config(
+        model="Cohere-parse-v5", provider=LlmProviders.AZURE_AI
+    )
+
+    assert isinstance(config, AzureAIPassthroughConfig)
+
+
+def test_router_model_prefix_is_stripped_and_native_path_kept_verbatim():
+    url, base = AzureAIPassthroughConfig().get_complete_url(
+        api_base=FOUNDRY_BASE,
+        api_key=None,
+        model="Cohere-parse-v5",
+        endpoint="Cohere-parse-v5/providers/cohere/v2/parse",
+        request_query_params=None,
+        litellm_params={},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/providers/cohere/v2/parse"
+    assert base == FOUNDRY_BASE
+
+
+def test_model_group_prefix_is_stripped_when_router_metadata_names_it():
+    url, _ = AzureAIPassthroughConfig().get_complete_url(
+        api_base=FOUNDRY_BASE,
+        api_key=None,
+        model="Cohere-parse-v5",
+        endpoint="/parse-alias/providers/cohere/v2/parse",
+        request_query_params=None,
+        litellm_params={"litellm_metadata": {"model_group": "parse-alias"}},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/providers/cohere/v2/parse"
+
+
+def test_model_inside_the_path_stays_and_query_params_are_forwarded():
+    url, _ = AzureAIPassthroughConfig().get_complete_url(
+        api_base=f"{FOUNDRY_BASE}/",
+        api_key=None,
+        model="gpt-5.4-mini",
+        endpoint="openai/deployments/gpt-5.4-mini/chat/completions",
+        request_query_params={"api-version": "2024-10-21"},
+        litellm_params={},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/openai/deployments/gpt-5.4-mini/chat/completions?api-version=2024-10-21"
+
+
+def test_api_base_that_already_ends_in_models_is_cut_back_to_the_foundry_root():
+    url, base = AzureAIPassthroughConfig().get_complete_url(
+        api_base=f"{FOUNDRY_BASE}/models",
+        api_key="key",
+        model="gpt-5.4-mini",
+        endpoint="gpt-5.4-mini/models/chat/completions",
+        request_query_params={"api-version": "2024-05-01-preview"},
+        litellm_params={},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/models/chat/completions?api-version=2024-05-01-preview"
+    assert base == FOUNDRY_BASE
+
+
+def test_full_url_api_base_that_already_ends_with_the_native_path_is_not_doubled():
+    model_router_url = (
+        "https://my-resource.cognitiveservices.azure.com/openai/deployments/model-router/chat/completions"
+    )
+
+    url, base = AzureAIPassthroughConfig().get_complete_url(
+        api_base=f"{model_router_url}?api-version=2025-01-01-preview",
+        api_key="key",
+        model="model_router/model-router",
+        endpoint="model-router/chat/completions",
+        request_query_params=None,
+        litellm_params={"litellm_metadata": {"model_group": "model-router"}},
+    )
+
+    assert str(url) == f"{model_router_url}?api-version=2025-01-01-preview"
+    assert base == "https://my-resource.cognitiveservices.azure.com/openai/deployments/model-router"
+
+
+@pytest.mark.parametrize("relayed_deployment", ["gpt-4o", "GPT-4o"])
+def test_deployment_root_api_base_is_not_repeated_when_the_relay_carries_the_deployment_path(relayed_deployment):
+    url, base = AzureAIPassthroughConfig().get_complete_url(
+        api_base="https://my-resource.openai.azure.com/openai/deployments/gpt-4o",
+        api_key="key",
+        model="gpt-4o",
+        endpoint=f"aoai-gpt-4o/openai/deployments/{relayed_deployment}/chat/completions",
+        request_query_params={"api-version": "2024-10-21"},
+        litellm_params={"litellm_metadata": {"model_group": "aoai-gpt-4o"}},
+    )
+
+    assert str(url) == (
+        f"https://my-resource.openai.azure.com/openai/deployments/{relayed_deployment}/chat/completions"
+        "?api-version=2024-10-21"
+    )
+    assert base == "https://my-resource.openai.azure.com"
+
+
+def test_deployment_named_like_the_first_native_segment_keeps_its_deployment_root():
+    url, base = AzureAIPassthroughConfig().get_complete_url(
+        api_base="https://my-resource.openai.azure.com/openai/deployments/chat",
+        api_key="key",
+        model="chat",
+        endpoint="aoai-chat/chat/completions",
+        request_query_params={"api-version": "2024-10-21"},
+        litellm_params={"litellm_metadata": {"model_group": "aoai-chat"}},
+    )
+
+    assert str(url) == "https://my-resource.openai.azure.com/openai/deployments/chat/chat/completions?api-version=2024-10-21"
+    assert base == "https://my-resource.openai.azure.com/openai/deployments/chat"
+
+
+def test_parse_relay_under_a_models_api_base_targets_the_foundry_root():
+    url, _ = AzureAIPassthroughConfig().get_complete_url(
+        api_base=f"{FOUNDRY_BASE}/models",
+        api_key="key",
+        model="Cohere-parse-v5",
+        endpoint="Cohere-parse-v5/providers/cohere/v2/parse",
+        request_query_params=None,
+        litellm_params={},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/providers/cohere/v2/parse"
+
+
+def test_deployment_api_version_fills_in_when_the_caller_sends_none():
+    url, _ = AzureAIPassthroughConfig().get_complete_url(
+        api_base=FOUNDRY_BASE,
+        api_key="key",
+        model="gpt-5.4-mini",
+        endpoint="gpt-5.4-mini/models/chat/completions",
+        request_query_params=None,
+        litellm_params={"api_version": "2024-05-01-preview"},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/models/chat/completions?api-version=2024-05-01-preview"
+
+
+def test_callers_api_version_beats_the_deployments():
+    url, _ = AzureAIPassthroughConfig().get_complete_url(
+        api_base=FOUNDRY_BASE,
+        api_key="key",
+        model="gpt-5.4-mini",
+        endpoint="gpt-5.4-mini/models/chat/completions",
+        request_query_params={"api-version": "2025-04-01-preview"},
+        litellm_params={"api_version": "2024-05-01-preview"},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/models/chat/completions?api-version=2025-04-01-preview"
+
+
+def test_api_version_on_the_configured_api_base_is_the_last_fallback():
+    url, _ = AzureAIPassthroughConfig().get_complete_url(
+        api_base=f"{FOUNDRY_BASE}/models/chat/completions?api-version=2024-05-01-preview",
+        api_key="key",
+        model="gpt-5.4-mini",
+        endpoint="gpt-5.4-mini/models/chat/completions",
+        request_query_params=None,
+        litellm_params={},
+    )
+
+    assert str(url) == f"{FOUNDRY_BASE}/models/chat/completions?api-version=2024-05-01-preview"
+
+
+def test_missing_api_base_raises_instead_of_building_a_relative_url():
+    with pytest.raises(ValueError, match="AZURE_AI_API_BASE"):
+        AzureAIPassthroughConfig().get_complete_url(
+            api_base=None,
+            api_key=None,
+            model="Cohere-parse-v5",
+            endpoint="Cohere-parse-v5/providers/cohere/v2/parse",
+            request_query_params=None,
+            litellm_params={},
+        )
+
+
+def _auth_headers(api_key: str | None, api_base: str, litellm_params: dict | None = None) -> dict:
+    return AzureAIPassthroughConfig().validate_environment(
+        headers={"content-type": "application/json"},
+        model="Cohere-parse-v5",
+        messages=[],
+        optional_params={},
+        litellm_params=litellm_params or {},
+        api_key=api_key,
+        api_base=api_base,
+    )
+
+
+def test_foundry_host_gets_the_api_key_header():
+    headers = _auth_headers(api_key="deployment-key", api_base=FOUNDRY_BASE)
+
+    assert headers == {"content-type": "application/json", "api-key": "deployment-key"}
+
+
+def test_serverless_host_gets_a_bearer_token():
+    headers = _auth_headers(api_key="deployment-key", api_base="https://cohere-parse.eastus.models.ai.azure.com")
+
+    assert headers["Authorization"] == "Bearer deployment-key"
+    assert "api-key" not in headers
+
+
+def test_entra_token_is_used_when_the_deployment_has_no_api_key():
+    headers = _auth_headers(api_key=None, api_base=FOUNDRY_BASE, litellm_params={"azure_ad_token": "entra-token"})
+
+    assert headers["Authorization"] == "Bearer entra-token"
+
+
+def test_no_credentials_at_all_raises():
+    with pytest.raises(ValueError, match="Missing Azure AI credentials"):
+        _auth_headers(api_key=None, api_base=FOUNDRY_BASE)
+
+
+@pytest.mark.parametrize(
+    "request_data, expected",
+    [({"stream": True}, True), ({"stream": 1}, True), ({"stream": False}, False), ({}, False)],
+)
+def test_is_streaming_request_reads_the_stream_flag(request_data, expected):
+    assert (
+        AzureAIPassthroughConfig().is_streaming_request(endpoint="models/chat/completions", request_data=request_data)
+        is expected
+    )
+
+
+def _chat_completion_response() -> httpx.Response:
+    body = {
+        "id": "chatcmpl-1",
+        "object": "chat.completion",
+        "created": 1700000000,
+        "model": "gpt-5.4-mini",
+        "choices": [{"index": 0, "message": {"role": "assistant", "content": "hi"}, "finish_reason": "stop"}],
+        "usage": {"prompt_tokens": 10, "completion_tokens": 8, "total_tokens": 18},
+    }
+    return httpx.Response(
+        status_code=200,
+        headers={"content-type": "application/json"},
+        content=json.dumps(body).encode("utf-8"),
+        request=httpx.Request("POST", f"{FOUNDRY_BASE}/models/chat/completions"),
+    )
+
+
+def test_chat_completions_relay_yields_a_model_response_for_cost_tracking():
+    result = AzureAIPassthroughConfig().logging_non_streaming_response(
+        model="gpt-5.4-mini",
+        custom_llm_provider="azure_ai",
+        httpx_response=_chat_completion_response(),
+        request_data={"model": "gpt-5.4-mini", "messages": [{"role": "user", "content": "hi"}]},
+        logging_obj=MagicMock(),
+        endpoint="models/chat/completions",
+    )
+
+    assert isinstance(result, ModelResponse)
+    assert result.choices[0].message.content == "hi"
+    assert result.usage.prompt_tokens == 10
+    assert result.usage.completion_tokens == 8
+
+
+def _non_chat_logging_result(content: bytes, content_type: str):
+    parse_response = httpx.Response(
+        status_code=200,
+        headers={"content-type": content_type},
+        content=content,
+        request=httpx.Request("POST", f"{FOUNDRY_BASE}/providers/cohere/v2/parse"),
+    )
+    return AzureAIPassthroughConfig().logging_non_streaming_response(
+        model="Cohere-parse-v5",
+        custom_llm_provider="azure_ai",
+        httpx_response=parse_response,
+        request_data={"model": "Cohere-parse-v5"},
+        logging_obj=MagicMock(),
+        endpoint="providers/cohere/v2/parse",
+    )
+
+
+def test_non_chat_relay_with_a_non_json_body_logs_the_raw_text():
+    assert _non_chat_logging_result(b"page one", "text/plain") == {"response": "page one"}
+
+
+def _relay_logging_obj(
+    model: str,
+    api_base: str,
+    stream: bool = False,
+    callbacks: list[CustomLogger] | None = None,
+    endpoint: str = "",
+) -> Logging:
+    logging_obj = Logging(
+        model=model,
+        messages=[],
+        stream=stream,
+        call_type="allm_passthrough_route",
+        start_time=datetime.now(),
+        litellm_call_id="call-1",
+        function_id="fn-1",
+        dynamic_async_success_callbacks=callbacks,
+    )
+    logging_obj.update_environment_variables(
+        model=model,
+        litellm_params={"api_base": api_base, "custom_llm_provider": "azure_ai"},
+        optional_params={},
+        custom_llm_provider="azure_ai",
+        endpoint=endpoint,
+    )
+    return logging_obj
+
+
+def _relay_logging_result(
+    config: AzureAIPassthroughConfig,
+    model: str,
+    native_path: str,
+    body,
+    api_base: str = FOUNDRY_BASE,
+    status_code: int = 200,
+):
+    relayed_url = f"{FOUNDRY_BASE}/{native_path}?api-version=2024-05-01-preview"
+    logging_obj = _relay_logging_obj(model, api_base)
+    response = httpx.Response(
+        status_code=status_code,
+        headers={"content-type": "application/json"},
+        content=json.dumps(body).encode("utf-8"),
+        request=httpx.Request("POST", relayed_url),
+    )
+    result = config.logging_non_streaming_response(
+        model=model,
+        custom_llm_provider="azure_ai",
+        httpx_response=response,
+        request_data={"model": model},
+        logging_obj=logging_obj,
+        endpoint=f"{model}/{native_path}",
+    )
+    return result, logging_obj
+
+
+MISTRAL_OCR_BODY = {
+    "pages": [{"index": 0, "markdown": "page one"}, {"index": 1, "markdown": "page two"}],
+    "model": "mistral-document-ai-2512",
+    "usage_info": {"pages_processed": 2, "doc_size_bytes": 4321},
+}
+
+
+def test_mistral_document_ai_relay_is_costed_per_page():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "mistral-document-ai-2512", "providers/mistral/azure/ocr", MISTRAL_OCR_BODY
+    )
+    per_page = litellm.get_model_info("azure_ai/mistral-document-ai-2512")["ocr_cost_per_page"]
+
+    assert isinstance(result, OCRResponse)
+    assert result.usage_info.pages_processed == 2
+    assert per_page > 0
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(2 * per_page)
+
+
+def test_ocr_route_under_a_models_api_base_is_still_recognised():
+    result, _ = _relay_logging_result(
+        AzureAIPassthroughConfig(),
+        "mistral-document-ai-2512",
+        "providers/mistral/azure/ocr",
+        MISTRAL_OCR_BODY,
+        api_base=f"{FOUNDRY_BASE}/models",
+    )
+
+    assert isinstance(result, OCRResponse)
+
+
+def test_relay_to_a_non_ocr_route_keeps_the_passthrough_object_and_call_type():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "mistral-document-ai-2512", "models/info", {"name": "mistral-document-ai-2512"}
+    )
+
+    assert result == {"response": {"name": "mistral-document-ai-2512"}}
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+COHERE_PARSE_BODY = {"id": "parse-1", "pages": [], "meta": {"billed_units": {"pages": 3}}}
+
+
+def test_cohere_parse_relay_is_costed_per_billed_page():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "Cohere-parse-v5", "providers/cohere/v2/parse", COHERE_PARSE_BODY
+    )
+    per_page = litellm.get_model_info("azure_ai/Cohere-parse-v5")["ocr_cost_per_page"]
+
+    assert isinstance(result, OCRResponse)
+    assert result.usage_info.pages_processed == 3
+    assert logging_obj.call_type == "aocr"
+    assert per_page > 0
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(3 * per_page)
+
+
+def test_deployment_without_an_ocr_config_is_never_costed_as_ocr():
+    config = AzureAIPassthroughConfig(ocr_config_for=lambda model: None)
+    result, logging_obj = _relay_logging_result(
+        config, "mistral-document-ai-2512", "providers/mistral/azure/ocr", MISTRAL_OCR_BODY
+    )
+
+    assert result == {"response": MISTRAL_OCR_BODY}
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+def test_accepted_ocr_job_without_a_result_body_is_not_costed():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(),
+        "mistral-document-ai-2512",
+        "providers/mistral/azure/ocr",
+        {"status": "running"},
+        status_code=202,
+    )
+
+    assert result == {"response": {"status": "running"}}
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+def test_unparseable_ocr_body_falls_back_to_the_passthrough_object():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(),
+        "mistral-document-ai-2512",
+        "providers/mistral/azure/ocr",
+        ["not", "an", "ocr", "body"],
+    )
+
+    assert result == {"response": '["not", "an", "ocr", "body"]'}
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+EMBEDDINGS_BODY = {
+    "object": "list",
+    "data": [{"object": "embedding", "index": 0, "embedding": [0.1, 0.2]}],
+    "model": "embed-v-4-0",
+    "usage": {"prompt_tokens": 1200, "total_tokens": 1200},
+}
+
+RERANK_BODY = {
+    "id": "rerank-1",
+    "results": [{"index": 1, "relevance_score": 0.9}, {"index": 0, "relevance_score": 0.2}],
+    "meta": {"api_version": {"version": "2"}, "billed_units": {"search_units": 2}},
+}
+
+IMAGE_BODY = {"created": 1, "data": [{"b64_json": "AAAA"}]}
+
+
+def test_foundry_embeddings_relay_is_costed_per_input_token():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "embed-v-4-0", "models/embeddings", EMBEDDINGS_BODY
+    )
+    per_token = litellm.get_model_info("azure_ai/embed-v-4-0")["input_cost_per_token"]
+
+    assert isinstance(result, EmbeddingResponse)
+    assert logging_obj.call_type == "aembedding"
+    assert per_token > 0
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(1200 * per_token)
+
+
+def test_cohere_rerank_relay_is_costed_per_search_unit():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "cohere-rerank-v4.0-fast", "providers/cohere/v2/rerank", RERANK_BODY
+    )
+    per_query = litellm.get_model_info("azure_ai/cohere-rerank-v4.0-fast")["input_cost_per_query"]
+
+    assert isinstance(result, RerankResponse)
+    assert logging_obj.call_type == "arerank"
+    assert per_query > 0
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(2 * per_query)
+
+
+def test_image_generation_relay_is_costed_per_image():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "FLUX.2-pro", "openai/deployments/FLUX.2-pro/images/generations", IMAGE_BODY
+    )
+    per_image = litellm.get_model_info("azure_ai/FLUX.2-pro")["output_cost_per_image"]
+
+    assert isinstance(result, ImageResponse)
+    assert logging_obj.call_type == "aimage_generation"
+    assert per_image > 0
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(per_image)
+
+
+def test_flux_2_relay_through_the_provider_route_is_costed_per_image():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(), "FLUX.2-pro", "providers/blackforestlabs/v1/flux-2-pro", IMAGE_BODY
+    )
+    per_image = litellm.get_model_info("azure_ai/FLUX.2-pro")["output_cost_per_image"]
+
+    assert isinstance(result, ImageResponse)
+    assert logging_obj.call_type == "aimage_generation"
+    assert logging_obj._response_cost_calculator(result=result) == pytest.approx(per_image)
+
+
+def test_rejected_rerank_relay_keeps_the_passthrough_object_and_call_type():
+    result, logging_obj = _relay_logging_result(
+        AzureAIPassthroughConfig(),
+        "cohere-rerank-v4.0-fast",
+        "providers/cohere/v2/rerank",
+        {"message": "invalid request"},
+        status_code=400,
+    )
+
+    assert result == {"response": {"message": "invalid request"}}
+    assert logging_obj.call_type == "allm_passthrough_route"
+
+
+def test_streaming_chat_completion_chunks_are_costed_like_azure():
+    head = {"id": "chatcmpl-1", "object": "chat.completion.chunk", "created": 1, "model": "gpt-5.4-mini"}
+    chunks = [
+        "data: "
+        + json.dumps(
+            {
+                **head,
+                "choices": [{"index": 0, "delta": {"role": "assistant", "content": "hi"}, "finish_reason": "stop"}],
+            }
+        ),
+        "data: "
+        + json.dumps({**head, "choices": [], "usage": {"prompt_tokens": 3, "completion_tokens": 1, "total_tokens": 4}}),
+        "data: [DONE]",
+    ]
+
+    response = AzureAIPassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=chunks,
+        litellm_logging_obj=MagicMock(),
+        model="gpt-5.4-mini",
+        custom_llm_provider="azure_ai",
+        endpoint="chat/completions",
+    )
+
+    assert isinstance(response, ModelResponse)
+    assert response.choices[0].message.content == "hi"
+    assert response.usage.total_tokens == 4
+
+
+def test_streaming_responses_chunks_through_a_router_relay_are_costed_like_azure():
+    logging_obj = _relay_logging_obj("gpt-5.4-mini", FOUNDRY_BASE)
+
+    response = AzureAIPassthroughConfig().handle_logging_collected_chunks(
+        all_chunks=["event: response.completed", "data: " + json.dumps(RESPONSES_COMPLETED_EVENT)],
+        litellm_logging_obj=logging_obj,
+        model="gpt-5.4-mini",
+        custom_llm_provider="azure_ai",
+        endpoint="gpt/openai/responses",
+    )
+    info = litellm.get_model_info("azure_ai/gpt-5.4-mini")
+
+    assert response is not None
+    assert response.response.usage.output_tokens == 100
+    assert logging_obj.call_type == "aresponses"
+    assert logging_obj._response_cost_calculator(result=response.response) == pytest.approx(
+        1000 * info["input_cost_per_token"] + 100 * info["output_cost_per_token"]
+    )
+
+
+async def test_streaming_responses_relay_flush_reaches_the_success_callbacks_with_a_price():
+    probe = _SpendProbe()
+    logging_obj = _relay_logging_obj(
+        "gpt-5.4-mini", FOUNDRY_BASE, stream=True, callbacks=[probe], endpoint="gpt/openai/responses"
+    )
+    stream = "event: response.completed\ndata: " + json.dumps(RESPONSES_COMPLETED_EVENT) + "\n\n"
+
+    await logging_obj.async_flush_passthrough_collected_chunks(
+        raw_bytes=[stream.encode()], provider_config=AzureAIPassthroughConfig()
+    )
+    info = litellm.get_model_info("azure_ai/gpt-5.4-mini")
+
+    assert probe.logged_call_type == "allm_passthrough_route"
+    assert probe.logged_cost == pytest.approx(1000 * info["input_cost_per_token"] + 100 * info["output_cost_per_token"])
diff --git a/tests/test_litellm/llms/azure_ai/test_azure_ai_cost_calculator.py b/tests/test_litellm/llms/azure_ai/test_azure_ai_cost_calculator.py
index 9612d97d946..a43fc3332af 100644
--- a/tests/test_litellm/llms/azure_ai/test_azure_ai_cost_calculator.py
+++ b/tests/test_litellm/llms/azure_ai/test_azure_ai_cost_calculator.py
@@ -2,20 +2,25 @@
 Test Azure AI cost calculator, especially Model Router flat cost.
 """
 
+from datetime import datetime
+from typing import Final
+
 import pytest
 
+import litellm
+from litellm.cost_calculator import completion_cost
+from litellm.litellm_core_utils.litellm_logging import Logging
 from litellm.llms.azure_ai.cost_calculator import (
-    _is_azure_model_router,
+    calculate_azure_model_router_flat_cost,
     cost_per_token,
+    is_azure_model_router,
 )
-from litellm.types.utils import Usage
+from litellm.types.utils import Choices, Message, ModelResponse, Usage
 from litellm.utils import get_model_info
 
 # Get the flat cost from model_prices_and_context_window.json
 _model_info = get_model_info(model="model_router", custom_llm_provider="azure_ai")
-AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS = (
-    _model_info.get("input_cost_per_token", 0) * 1_000_000
-)
+AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS = _model_info.get("input_cost_per_token", 0) * 1_000_000
 
 
 class TestAzureModelRouterDetection:
@@ -49,7 +54,7 @@ class TestAzureModelRouterDetection:
     )
     def test_is_azure_model_router(self, model: str, expected: bool):
         """Test Azure Model Router detection."""
-        assert _is_azure_model_router(model) == expected
+        assert is_azure_model_router(model) == expected
 
 
 class TestAzureModelRouterPrefix:
@@ -80,108 +85,60 @@ class TestAzureModelRouterPrefix:
         assert result == expected
 
 
+ROUTER_FEE_PER_TOKEN: Final = AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS / 1_000_000
+ROUTED_MODEL: Final = "gpt-4.1-nano-2025-04-14"
+ROUTED_USAGE: Final = Usage(prompt_tokens=5000, completion_tokens=2000, total_tokens=7000)
+ROUTED_FEE: Final = 5000 * ROUTER_FEE_PER_TOKEN
+
+
+def _router_logging(request_model: str) -> Logging:
+    return Logging(
+        model=request_model,
+        messages=[{"role": "user", "content": "Hello"}],
+        stream=False,
+        call_type="completion",
+        start_time=datetime.now(),
+        litellm_call_id="test-123",
+        function_id="test-function",
+    )
+
+
+def _azure_ai_response(response_model: str, litellm_model_name: str | None = None) -> ModelResponse:
+    response: Final = ModelResponse(
+        id="test-123",
+        choices=[Choices(finish_reason="stop", index=0, message=Message(role="assistant", content="Hello"))],
+        created=1234567890,
+        model=response_model,
+        object="chat.completion",
+        usage=ROUTED_USAGE,
+    )
+    response._hidden_params = (
+        {"custom_llm_provider": "azure_ai"}
+        if litellm_model_name is None
+        else {"custom_llm_provider": "azure_ai", "litellm_model_name": litellm_model_name}
+    )
+    return response
+
+
+def _routed_model_cost() -> tuple[float, float]:
+    routed_info: Final = get_model_info(model=ROUTED_MODEL, custom_llm_provider="azure_ai")
+    return (
+        ROUTED_USAGE.prompt_tokens * (routed_info["input_cost_per_token"] or 0.0),
+        ROUTED_USAGE.completion_tokens * (routed_info["output_cost_per_token"] or 0.0),
+    )
+
+
+@pytest.mark.usefixtures("local_model_cost_map")
 class TestAzureModelRouterFlatCost:
-    """Test Azure AI Foundry Model Router flat cost calculation."""
+    """cost_per_token charges the router fee once, for whichever router name the caller gives it."""
 
-    def test_model_router_flat_cost_basic(self):
-        """Test that flat cost is added for Model Router requests."""
-        model = "azure-model-router"
-        usage = Usage(
-            prompt_tokens=1000,
-            completion_tokens=500,
-            total_tokens=1500,
-        )
+    def test_unmapped_router_deployment_name_prices_the_fee(self) -> None:
+        usage = Usage(prompt_tokens=1000, completion_tokens=500, total_tokens=1500)
+        prompt_cost, completion_cost_usd = cost_per_token(model="azure-model-router", usage=usage)
+        assert prompt_cost == pytest.approx(1000 * ROUTER_FEE_PER_TOKEN, rel=1e-9)
+        assert completion_cost_usd == 0.0
 
-        prompt_cost, completion_cost = cost_per_token(model=model, usage=usage)
-
-        # Calculate expected flat cost
-        expected_flat_cost = (
-            usage.prompt_tokens
-            * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS
-            / 1_000_000
-        )
-
-        # Flat cost should be $0.00014 (1000 tokens × $0.14 / 1M tokens)
-        assert expected_flat_cost == pytest.approx(0.00014, rel=1e-9)
-
-        # Prompt cost should include the flat cost
-        # (plus any base cost from the actual model used, which might be 0 if not in model_cost)
-        assert prompt_cost >= expected_flat_cost
-        print(
-            f"Model Router flat cost for {usage.prompt_tokens} tokens: ${expected_flat_cost:.6f}"
-        )
-        print(f"Total prompt cost: ${prompt_cost:.6f}")
-
-    def test_model_router_flat_cost_large_request(self):
-        """Test flat cost calculation for larger requests."""
-        model = "model-router"
-        usage = Usage(
-            prompt_tokens=100_000,
-            completion_tokens=50_000,
-            total_tokens=150_000,
-        )
-
-        prompt_cost, completion_cost = cost_per_token(model=model, usage=usage)
-
-        # Calculate expected flat cost
-        expected_flat_cost = (
-            usage.prompt_tokens
-            * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS
-            / 1_000_000
-        )
-
-        # Flat cost should be $0.014 (100k tokens × $0.14 / 1M tokens)
-        assert expected_flat_cost == pytest.approx(0.014, rel=1e-9)
-        # Use approx for floating-point comparison
-        assert prompt_cost >= expected_flat_cost or prompt_cost == pytest.approx(
-            expected_flat_cost, rel=1e-9
-        )
-        print(
-            f"Model Router flat cost for {usage.prompt_tokens} tokens: ${expected_flat_cost:.6f}"
-        )
-        print(f"Total prompt cost: ${prompt_cost:.6f}")
-
-    def test_model_router_flat_cost_1m_tokens(self):
-        """Test flat cost for exactly 1 million input tokens."""
-        model = "azure-model-router"
-        usage = Usage(
-            prompt_tokens=1_000_000,
-            completion_tokens=100_000,
-            total_tokens=1_100_000,
-        )
-
-        prompt_cost, completion_cost = cost_per_token(model=model, usage=usage)
-
-        # Calculate expected flat cost
-        expected_flat_cost = AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS
-
-        # Flat cost should be exactly $0.14 for 1M tokens
-        assert expected_flat_cost == pytest.approx(0.14, rel=1e-9)
-        assert prompt_cost >= expected_flat_cost
-        print(f"Model Router flat cost for 1M tokens: ${expected_flat_cost:.6f}")
-        print(f"Total prompt cost: ${prompt_cost:.6f}")
-
-    def test_non_model_router_no_flat_cost(self):
-        """Test that non-Model Router models don't get the flat cost."""
-        model = "gpt-4o"
-        usage = Usage(
-            prompt_tokens=1000,
-            completion_tokens=500,
-            total_tokens=1500,
-        )
-
-        prompt_cost, completion_cost = cost_per_token(model=model, usage=usage)
-
-        # No flat cost should be added for non-Model Router models
-        # The cost might be 0 or based on the model's pricing
-        print(f"Non-Model Router prompt cost: ${prompt_cost:.6f}")
-        # We just ensure it doesn't crash and returns valid values
-        assert prompt_cost >= 0
-        assert completion_cost >= 0
-
-    def test_model_router_with_cached_tokens(self):
-        """Test Model Router flat cost with cached tokens."""
-        model = "azure-model-router"
+    def test_unmapped_router_deployment_name_charges_the_fee_over_cached_prompt_tokens_too(self) -> None:
         usage = Usage(
             prompt_tokens=2000,
             completion_tokens=800,
@@ -189,268 +146,165 @@ class TestAzureModelRouterFlatCost:
             cache_read_input_tokens=500,
             cache_creation_input_tokens=200,
         )
+        prompt_cost, completion_cost_usd = cost_per_token(model="azure-model-router", usage=usage)
+        assert prompt_cost == pytest.approx(2000 * ROUTER_FEE_PER_TOKEN, rel=1e-9)
+        assert completion_cost_usd == 0.0
 
-        prompt_cost, completion_cost = cost_per_token(model=model, usage=usage)
-
-        # Flat cost is based on ALL prompt tokens (including cached)
-        expected_flat_cost = (
-            usage.prompt_tokens
-            * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS
-            / 1_000_000
+    def test_router_deployment_name_as_both_names_charges_the_fee_once(self) -> None:
+        usage = Usage(prompt_tokens=1000, completion_tokens=500, total_tokens=1500)
+        prompt_cost, completion_cost_usd = cost_per_token(
+            model="model_router/my-deployment", usage=usage, request_model="azure_ai/model_router/my-deployment"
         )
+        assert prompt_cost == pytest.approx(1000 * ROUTER_FEE_PER_TOKEN, rel=1e-9)
+        assert completion_cost_usd == 0.0
 
-        assert expected_flat_cost == pytest.approx(0.00028, rel=1e-9)
-        assert prompt_cost >= expected_flat_cost
-        print(
-            f"Model Router flat cost with caching for {usage.prompt_tokens} tokens: ${expected_flat_cost:.6f}"
+    @pytest.mark.parametrize("router_entry_name", ["model_router", "model-router"])
+    def test_router_entry_prices_its_own_fee(self, router_entry_name: str) -> None:
+        usage = Usage(prompt_tokens=1_000_000, completion_tokens=0, total_tokens=1_000_000)
+        prompt_cost, completion_cost_usd = cost_per_token(model=router_entry_name, usage=usage)
+        assert prompt_cost == pytest.approx(0.14, rel=1e-9)
+        assert completion_cost_usd == 0.0
+
+    def test_routed_model_is_priced_as_itself(self) -> None:
+        routed_prompt_cost, routed_completion_cost = _routed_model_cost()
+        prompt_cost, completion_cost_usd = cost_per_token(model=ROUTED_MODEL, usage=ROUTED_USAGE)
+        assert routed_prompt_cost > 0
+        assert prompt_cost == pytest.approx(routed_prompt_cost, rel=1e-9)
+        assert completion_cost_usd == pytest.approx(routed_completion_cost, rel=1e-9)
+
+    def test_unmapped_model_that_is_not_a_router_name_raises(self) -> None:
+        usage = Usage(prompt_tokens=10, completion_tokens=10, total_tokens=20)
+        with pytest.raises(Exception, match="no-such-azure-ai-model"):
+            cost_per_token(model="no-such-azure-ai-model", usage=usage)
+
+    def test_request_model_through_the_router_adds_the_fee_once(self) -> None:
+        routed_prompt_cost, routed_completion_cost = _routed_model_cost()
+        prompt_cost, completion_cost_usd = cost_per_token(
+            model=ROUTED_MODEL, usage=ROUTED_USAGE, request_model="azure_ai/model-router"
         )
-        print(f"Total prompt cost: ${prompt_cost:.6f}")
+        assert prompt_cost == pytest.approx(routed_prompt_cost + ROUTED_FEE, rel=1e-9)
+        assert completion_cost_usd == pytest.approx(routed_completion_cost, rel=1e-9)
 
-    def test_router_flat_cost_when_response_has_actual_model(self):
-        """
-        Test that router flat cost is added when request was via router but response
-        contains the actual model (e.g., gpt-5-nano).
+    def test_request_model_that_is_not_the_router_adds_nothing(self) -> None:
+        routed_prompt_cost, routed_completion_cost = _routed_model_cost()
+        assert cost_per_token(
+            model=ROUTED_MODEL, usage=ROUTED_USAGE, request_model=f"azure_ai/{ROUTED_MODEL}"
+        ) == pytest.approx((routed_prompt_cost, routed_completion_cost), rel=1e-9)
 
-        This is the key fix: Azure returns the actual model in the response, but we
-        must still add the router flat cost because the request was made via model router.
-        """
-        usage = Usage(
-            prompt_tokens=10000,
-            completion_tokens=5000,
-            total_tokens=15000,
+    @pytest.mark.parametrize("router_entry_name", ["model_router", "model-router"])
+    def test_request_model_does_not_double_the_router_entry(self, router_entry_name: str) -> None:
+        prompt_cost, completion_cost_usd = cost_per_token(
+            model=router_entry_name, usage=ROUTED_USAGE, request_model=f"azure_ai/{router_entry_name}"
         )
+        assert prompt_cost == pytest.approx(ROUTED_FEE, rel=1e-9)
+        assert completion_cost_usd == 0.0
 
-        # Response model is the actual model Azure used (not a router name)
-        response_model = "gpt-5-nano-2025-08-07"
-        # Request model is the router - user called azure_ai/model_router/model-router
-        request_model = "azure_ai/model_router/model-router"
-
-        prompt_cost, completion_cost = cost_per_token(
-            model=response_model,
-            usage=usage,
-            request_model=request_model,
+    def test_public_cost_per_token_keeps_the_request_model_keyword(self) -> None:
+        routed_prompt_cost, routed_completion_cost = _routed_model_cost()
+        prompt_cost, completion_cost_usd = litellm.cost_per_token(
+            model=ROUTED_MODEL,
+            custom_llm_provider="azure_ai",
+            usage_object=ROUTED_USAGE,
+            request_model="azure_ai/model-router",
         )
+        assert prompt_cost == pytest.approx(routed_prompt_cost + ROUTED_FEE, rel=1e-9)
+        assert completion_cost_usd == pytest.approx(routed_completion_cost, rel=1e-9)
 
-        # Expected: model cost (from gpt-5-nano) + router flat cost
-        expected_flat_cost = (
-            usage.prompt_tokens
-            * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS
-            / 1_000_000
+    def test_flat_cost_helper(self) -> None:
+        assert calculate_azure_model_router_flat_cost(
+            model="azure-model-router", prompt_tokens=10_000
+        ) == pytest.approx(0.0014, rel=1e-9)
+        assert calculate_azure_model_router_flat_cost(model="gpt-5-nano", prompt_tokens=10_000) == 0.0
+
+    def test_flat_cost_reads_the_fee_from_the_deployment_named_entry(self) -> None:
+        litellm.register_model(
+            {"azure_ai/model-router": {"input_cost_per_token": 2e-07, "litellm_provider": "azure_ai", "mode": "chat"}}
         )
-        assert expected_flat_cost == pytest.approx(0.0014, rel=1e-9)
-
-        # Total cost should be model cost + flat cost
-        total_cost = prompt_cost + completion_cost
-        assert total_cost >= expected_flat_cost
-
-        # Prompt cost should include both model prompt cost and router flat cost
-        assert prompt_cost >= expected_flat_cost
+        litellm.get_model_info.cache_clear()
+        assert calculate_azure_model_router_flat_cost(model="model-router", prompt_tokens=1_000_000) == pytest.approx(
+            0.2, rel=1e-9
+        )
+        assert calculate_azure_model_router_flat_cost(
+            model="azure-model-router", prompt_tokens=1_000_000
+        ) == pytest.approx(0.14, rel=1e-9)
 
 
+@pytest.mark.usefixtures("local_model_cost_map")
 class TestAzureModelRouterCostBreakdown:
-    """Test that Azure Model Router flat cost is tracked in cost breakdown."""
+    """completion_cost charges the router fee exactly once: as the breakdown's additional cost line when a routed
+    model is priced as itself, inside the input cost when the priced name is the router."""
 
-    def test_flat_cost_calculation_helper(self):
-        """Test that flat cost can be calculated using the helper function."""
-        from litellm.llms.azure_ai.cost_calculator import (
-            calculate_azure_model_router_flat_cost,
-        )
-
-        model = "azure-model-router"
-        prompt_tokens = 10000
-
-        # Calculate flat cost using helper function
-        flat_cost = calculate_azure_model_router_flat_cost(
-            model=model, prompt_tokens=prompt_tokens
-        )
-
-        # Expected flat cost
-        expected_flat_cost = (
-            prompt_tokens * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS / 1_000_000
-        )
-
-        assert flat_cost > 0
-        assert flat_cost == pytest.approx(expected_flat_cost, rel=1e-9)
-        print(f"Flat cost calculated: ${flat_cost:.6f}")
-
-    def test_flat_cost_integration_with_completion_cost(self):
-        """Test that flat cost is properly integrated into completion_cost calculation."""
-        import litellm
-        from litellm.cost_calculator import completion_cost
-        from litellm.types.utils import Choices, Message, ModelResponse, Usage
-
-        # Create a mock response for azure_ai model router
-        response = ModelResponse(
-            id="test-123",
-            choices=[
-                Choices(
-                    finish_reason="stop",
-                    index=0,
-                    message=Message(
-                        role="assistant",
-                        content="Test response",
-                    ),
-                )
-            ],
-            created=1234567890,
-            model="azure-model-router",
-            object="chat.completion",
-            usage=Usage(
-                prompt_tokens=5000,
-                completion_tokens=2000,
-                total_tokens=7000,
-            ),
-        )
-
-        # Set hidden params for provider
-        response._hidden_params = {"custom_llm_provider": "azure_ai"}
-
-        # Calculate cost
+    def test_unmapped_router_deployment_name_costs_only_the_fee(self) -> None:
         cost = completion_cost(
-            completion_response=response,
+            completion_response=_azure_ai_response("azure-model-router"),
             model="azure-model-router",
             custom_llm_provider="azure_ai",
         )
+        assert cost == pytest.approx(ROUTED_FEE, rel=1e-9)
 
-        # Expected flat cost
-        expected_flat_cost = (
-            5000 * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS / 1_000_000
-        )
-
-        # Cost should include the flat cost (use approx for floating-point comparison)
-        assert cost >= expected_flat_cost or cost == pytest.approx(
-            expected_flat_cost, rel=1e-9
-        )
-        print(f"Total cost with flat fee: ${cost:.6f}")
-        print(f"Expected minimum flat cost: ${expected_flat_cost:.6f}")
-
-    def test_additional_costs_in_cost_breakdown(self):
-        """Test that Azure Model Router flat cost appears in additional_costs dict."""
-        from datetime import datetime
-
-        from litellm.cost_calculator import completion_cost
-        from litellm.litellm_core_utils.litellm_logging import Logging
-        from litellm.types.utils import Choices, Message, ModelResponse, Usage
-
-        # Create logging object with required parameters
-        logging_obj = Logging(
-            model="azure-model-router",
-            messages=[{"role": "user", "content": "Hello"}],
-            stream=False,
-            call_type="completion",
-            start_time=datetime.now(),
-            litellm_call_id="test-123",
-            function_id="test-function",
-        )
-
-        # Create a mock response for azure_ai model router
-        response = ModelResponse(
-            id="test-123",
-            choices=[
-                Choices(
-                    finish_reason="stop",
-                    index=0,
-                    message=Message(
-                        role="assistant",
-                        content="Test response",
-                    ),
-                )
-            ],
-            created=1234567890,
-            model="azure-model-router",
-            object="chat.completion",
-            usage=Usage(
-                prompt_tokens=5000,
-                completion_tokens=2000,
-                total_tokens=7000,
-            ),
-        )
-
-        # Set hidden params for provider
-        response._hidden_params = {"custom_llm_provider": "azure_ai"}
-
-        # Calculate cost with logging object
+    def test_unmapped_router_name_carries_the_fee_as_its_input_cost(self) -> None:
+        logging_obj = _router_logging("azure-model-router")
         cost = completion_cost(
-            completion_response=response,
+            completion_response=_azure_ai_response("azure-model-router"),
             model="azure-model-router",
             custom_llm_provider="azure_ai",
             litellm_logging_obj=logging_obj,
         )
+        breakdown = logging_obj.cost_breakdown
+        assert breakdown is not None
+        assert breakdown["input_cost"] == pytest.approx(ROUTED_FEE, rel=1e-9)
+        assert "additional_costs" not in breakdown
+        assert cost == pytest.approx(ROUTED_FEE, rel=1e-9)
 
-        # Check that cost breakdown contains additional_costs
-        assert hasattr(logging_obj, "cost_breakdown")
-        assert logging_obj.cost_breakdown is not None
-        assert "additional_costs" in logging_obj.cost_breakdown
-        assert isinstance(logging_obj.cost_breakdown["additional_costs"], dict)
-
-        # Check that the Azure Model Router flat cost is in additional_costs
-        additional_costs = logging_obj.cost_breakdown["additional_costs"]
-        assert "Azure Model Router Flat Cost" in additional_costs
-
-        # Verify the flat cost value
-        expected_flat_cost = (
-            5000 * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS / 1_000_000
-        )
-        actual_flat_cost = additional_costs["Azure Model Router Flat Cost"]
-        assert actual_flat_cost == pytest.approx(expected_flat_cost, rel=1e-9)
-
-        print(f"Additional costs in breakdown: {additional_costs}")
-        print(f"Azure Model Router Flat Cost: ${actual_flat_cost:.6f}")
-
-    def test_additional_costs_when_response_has_actual_model_via_hidden_params(self):
-        """additional_costs populated when response has actual model but request was via model router (hidden_params)."""
-        from datetime import datetime
-
-        from litellm.cost_calculator import completion_cost
-        from litellm.litellm_core_utils.litellm_logging import Logging
-        from litellm.types.utils import Choices, Message, ModelResponse, Usage
-
-        logging_obj = Logging(
-            model="gpt-4.1-nano-2025-04-14",
-            messages=[{"role": "user", "content": "Hello"}],
-            stream=False,
-            call_type="completion",
-            start_time=datetime.now(),
-            litellm_call_id="test-123",
-            function_id="test-function",
-        )
-        response = ModelResponse(
-            id="test-123",
-            choices=[
-                Choices(
-                    finish_reason="stop",
-                    index=0,
-                    message=Message(role="assistant", content="Hello"),
-                )
-            ],
-            created=1234567890,
-            model="gpt-4.1-nano-2025-04-14",
-            object="chat.completion",
-            usage=Usage(prompt_tokens=5000, completion_tokens=2000, total_tokens=7000),
-        )
-        response._hidden_params = {
-            "custom_llm_provider": "azure_ai",
-            "litellm_model_name": "azure_ai/model-router",
-        }
+    def test_router_request_with_routed_response_charges_the_fee_once(self) -> None:
+        routed_prompt_cost, routed_completion_cost = _routed_model_cost()
+        logging_obj = _router_logging("model-router")
         cost = completion_cost(
-            completion_response=response,
-            model="gpt-4.1-nano-2025-04-14",
+            completion_response=_azure_ai_response(ROUTED_MODEL),
+            model=ROUTED_MODEL,
             custom_llm_provider="azure_ai",
             litellm_logging_obj=logging_obj,
         )
-        expected_flat_cost = (
-            5000 * AZURE_MODEL_ROUTER_FLAT_COST_PER_M_INPUT_TOKENS / 1_000_000
+        breakdown = logging_obj.cost_breakdown
+        assert breakdown is not None
+        assert breakdown["input_cost"] == pytest.approx(routed_prompt_cost, rel=1e-9)
+        assert breakdown["output_cost"] == pytest.approx(routed_completion_cost, rel=1e-9)
+        assert breakdown.get("additional_costs") == pytest.approx(
+            {"Azure Model Router Flat Cost": ROUTED_FEE}, rel=1e-9
         )
-        assert cost >= expected_flat_cost
-        assert logging_obj.cost_breakdown is not None
-        assert "additional_costs" in logging_obj.cost_breakdown
-        assert (
-            "Azure Model Router Flat Cost"
-            in logging_obj.cost_breakdown["additional_costs"]
+        assert cost == pytest.approx(routed_prompt_cost + routed_completion_cost + ROUTED_FEE, rel=1e-9)
+
+    def test_routed_response_named_by_hidden_params_charges_the_fee_once(self) -> None:
+        routed_prompt_cost, routed_completion_cost = _routed_model_cost()
+        logging_obj = _router_logging(ROUTED_MODEL)
+        cost = completion_cost(
+            completion_response=_azure_ai_response(ROUTED_MODEL, litellm_model_name="azure_ai/model-router"),
+            model=ROUTED_MODEL,
+            custom_llm_provider="azure_ai",
+            litellm_logging_obj=logging_obj,
         )
-        assert logging_obj.cost_breakdown["additional_costs"][
-            "Azure Model Router Flat Cost"
-        ] == pytest.approx(expected_flat_cost, rel=1e-9)
+        breakdown = logging_obj.cost_breakdown
+        assert breakdown is not None
+        assert breakdown["input_cost"] == pytest.approx(routed_prompt_cost, rel=1e-9)
+        assert breakdown.get("additional_costs") == pytest.approx(
+            {"Azure Model Router Flat Cost": ROUTED_FEE}, rel=1e-9
+        )
+        assert cost == pytest.approx(routed_prompt_cost + routed_completion_cost + ROUTED_FEE, rel=1e-9)
+
+    @pytest.mark.parametrize("router_entry_name", ["model_router", "model-router"])
+    def test_response_priced_as_the_router_entry_charges_the_fee_once(self, router_entry_name: str) -> None:
+        logging_obj = _router_logging(router_entry_name)
+        cost = completion_cost(
+            completion_response=_azure_ai_response(router_entry_name),
+            model=router_entry_name,
+            custom_llm_provider="azure_ai",
+            litellm_logging_obj=logging_obj,
+        )
+        breakdown = logging_obj.cost_breakdown
+        assert breakdown is not None
+        assert "additional_costs" not in breakdown
+        assert breakdown["input_cost"] == pytest.approx(ROUTED_FEE, rel=1e-9)
+        assert cost == pytest.approx(ROUTED_FEE, rel=1e-9)
 
 
 class TestAzureAIServiceTierCostCalculation:
@@ -459,26 +313,27 @@ class TestAzureAIServiceTierCostCalculation:
     @pytest.fixture(autouse=True)
     def register_test_model(self):
         import litellm
-        litellm.register_model(model_cost={
-            "test-azure-ai-model": {
-                "input_cost_per_token": 0.001,
-                "output_cost_per_token": 0.002,
-                "input_cost_per_token_priority": 0.01,
-                "output_cost_per_token_priority": 0.02,
-                "input_cost_per_token_flex": 0.0005,
-                "output_cost_per_token_flex": 0.001,
-                "litellm_provider": "azure_ai",
-                "max_tokens": 8192,
+
+        litellm.register_model(
+            model_cost={
+                "test-azure-ai-model": {
+                    "input_cost_per_token": 0.001,
+                    "output_cost_per_token": 0.002,
+                    "input_cost_per_token_priority": 0.01,
+                    "output_cost_per_token_priority": 0.02,
+                    "input_cost_per_token_flex": 0.0005,
+                    "output_cost_per_token_flex": 0.001,
+                    "litellm_provider": "azure_ai",
+                    "max_tokens": 8192,
+                }
             }
-        })
+        )
 
     def test_service_tier_priority_higher_cost(self):
         """Priority tier should cost more than standard for azure_ai."""
         usage = Usage(prompt_tokens=1000, completion_tokens=500, total_tokens=1500)
 
-        standard_prompt, standard_completion = cost_per_token(
-            model="test-azure-ai-model", usage=usage
-        )
+        standard_prompt, standard_completion = cost_per_token(model="test-azure-ai-model", usage=usage)
         priority_prompt, priority_completion = cost_per_token(
             model="test-azure-ai-model", usage=usage, service_tier="priority"
         )
@@ -490,12 +345,8 @@ class TestAzureAIServiceTierCostCalculation:
         """Flex tier should cost less than standard for azure_ai."""
         usage = Usage(prompt_tokens=1000, completion_tokens=500, total_tokens=1500)
 
-        standard_prompt, standard_completion = cost_per_token(
-            model="test-azure-ai-model", usage=usage
-        )
-        flex_prompt, flex_completion = cost_per_token(
-            model="test-azure-ai-model", usage=usage, service_tier="flex"
-        )
+        standard_prompt, standard_completion = cost_per_token(model="test-azure-ai-model", usage=usage)
+        flex_prompt, flex_completion = cost_per_token(model="test-azure-ai-model", usage=usage, service_tier="flex")
 
         assert flex_prompt < standard_prompt
         assert flex_completion < standard_completion
diff --git a/tests/test_litellm/llms/azure_ai/test_azure_ai_foundry_catalog_model_metadata.py b/tests/test_litellm/llms/azure_ai/test_azure_ai_foundry_catalog_model_metadata.py
new file mode 100644
index 00000000000..84d5cd2a7d4
--- /dev/null
+++ b/tests/test_litellm/llms/azure_ai/test_azure_ai_foundry_catalog_model_metadata.py
@@ -0,0 +1,113 @@
+from pathlib import Path
+from typing import Final
+
+import pytest
+from pydantic import TypeAdapter
+
+from litellm import completion_cost, cost_per_token, get_model_info
+from litellm.litellm_core_utils.get_llm_provider_logic import get_llm_provider
+from litellm.types.utils import TranscriptionResponse
+
+REPO_ROOT: Final = Path(__file__).parents[4]
+MAIN_COST_MAP: Final = REPO_ROOT / "model_prices_and_context_window.json"
+BACKUP_COST_MAP: Final = REPO_ROOT / "litellm" / "model_prices_and_context_window_backup.json"
+COST_MAP_ADAPTER: Final = TypeAdapter(dict[str, dict[str, object]])
+AZURE_PRICING_PREFIX: Final = "https://azure.microsoft.com/en-us/pricing/details/"
+A_MILLION: Final = 1_000_000
+AN_HOUR_IN_SECONDS: Final = 3600
+
+TOKEN_PRICED_NAMES: Final = (
+    "gpt-chat-latest",
+    "codex-mini",
+    "model-router",
+    "cohere-command-a",
+    "grok-4-20-reasoning",
+    "grok-4-20-non-reasoning",
+)
+GROK_4_20_NAMES: Final = ("grok-4-20-reasoning", "grok-4-20-non-reasoning")
+CATALOG_NAMES: Final = TOKEN_PRICED_NAMES + ("whisper",)
+
+
+def _cost_map_entry(path: Path, catalog_name: str) -> dict[str, object]:
+    return COST_MAP_ADAPTER.validate_json(path.read_bytes())[f"azure_ai/{catalog_name}"]
+
+
+def _whisper_transcription_cost(duration_seconds: int) -> float:
+    transcription: Final = TranscriptionResponse(text="hello")
+    transcription._hidden_params = {  # pyright: ignore[reportPrivateUsage]  # TranscriptionResponse exposes no public hidden-params setter
+        "custom_llm_provider": "azure_ai",
+        "model": "azure_ai/whisper",
+        "audio_transcription_duration": duration_seconds,
+    }
+    return completion_cost(
+        completion_response=transcription,
+        model="azure_ai/whisper",
+        custom_llm_provider="azure_ai",
+        call_type="atranscription",
+    )
+
+
+@pytest.mark.parametrize("catalog_name", CATALOG_NAMES)
+def test_azure_ai_catalog_name_routes_to_azure_ai(catalog_name: str) -> None:
+    routed_model, provider, _, _ = get_llm_provider(model=f"azure_ai/{catalog_name}")
+    assert (routed_model, provider) == (catalog_name, "azure_ai")
+
+
+@pytest.mark.usefixtures("local_model_cost_map")
+@pytest.mark.parametrize("catalog_name", TOKEN_PRICED_NAMES)
+def test_azure_ai_catalog_name_charges_its_own_entry_per_token(catalog_name: str) -> None:
+    entry: Final = get_model_info(f"azure_ai/{catalog_name}")
+    prompt_cost, completion_cost_usd = cost_per_token(
+        model=f"azure_ai/{catalog_name}", prompt_tokens=A_MILLION, completion_tokens=A_MILLION
+    )
+    assert prompt_cost > 0
+    assert prompt_cost == pytest.approx(A_MILLION * entry["input_cost_per_token"])
+    assert completion_cost_usd == pytest.approx(A_MILLION * entry["output_cost_per_token"])
+
+
+@pytest.mark.usefixtures("local_model_cost_map")
+@pytest.mark.parametrize("catalog_name", TOKEN_PRICED_NAMES)
+def test_azure_ai_catalog_name_prices_the_same_in_any_casing(catalog_name: str) -> None:
+    lowercase_cost = cost_per_token(model=f"azure_ai/{catalog_name}", prompt_tokens=A_MILLION, completion_tokens=0)
+    upper_cost = cost_per_token(model=f"azure_ai/{catalog_name.upper()}", prompt_tokens=A_MILLION, completion_tokens=0)
+    assert upper_cost == lowercase_cost
+
+
+@pytest.mark.usefixtures("local_model_cost_map")
+@pytest.mark.parametrize("catalog_name", GROK_4_20_NAMES)
+def test_azure_ai_grok_4_20_bills_cached_prompt_tokens_at_the_input_price(catalog_name: str) -> None:
+    uncached_prompt_cost, _ = cost_per_token(model=f"azure_ai/{catalog_name}", prompt_tokens=A_MILLION, completion_tokens=0)
+    cached_prompt_cost, _ = cost_per_token(
+        model=f"azure_ai/{catalog_name}",
+        prompt_tokens=A_MILLION,
+        completion_tokens=0,
+        cache_read_input_tokens=A_MILLION,
+    )
+    assert uncached_prompt_cost > 0
+    assert cached_prompt_cost == pytest.approx(uncached_prompt_cost)
+
+
+@pytest.mark.usefixtures("local_model_cost_map")
+def test_azure_ai_whisper_catalog_name_is_priced_per_second() -> None:
+    one_second_cost: Final = _whisper_transcription_cost(1)
+    one_hour_cost: Final = _whisper_transcription_cost(AN_HOUR_IN_SECONDS)
+    assert one_second_cost > 0
+    assert one_hour_cost == pytest.approx(AN_HOUR_IN_SECONDS * one_second_cost)
+
+
+@pytest.mark.parametrize("catalog_name", CATALOG_NAMES)
+def test_azure_ai_catalog_entry_source_and_backup_match(catalog_name: str) -> None:
+    main_entry = _cost_map_entry(MAIN_COST_MAP, catalog_name)
+    backup_entry = _cost_map_entry(BACKUP_COST_MAP, catalog_name)
+
+    assert str(main_entry["source"]).startswith(AZURE_PRICING_PREFIX)
+    assert backup_entry == main_entry
+
+
+def test_azure_ai_model_router_spellings_share_one_entry() -> None:
+    underscore_entry = _cost_map_entry(MAIN_COST_MAP, "model_router")
+    hyphen_entry = _cost_map_entry(MAIN_COST_MAP, "model-router")
+
+    assert {k: v for k, v in underscore_entry.items() if k != "comment"} == {
+        k: v for k, v in hyphen_entry.items() if k != "comment"
+    }
diff --git a/tests/test_litellm/llms/bedrock/batches/test_handler.py b/tests/test_litellm/llms/bedrock/batches/test_handler.py
index 2a9b7a6d138..03daafcad72 100644
--- a/tests/test_litellm/llms/bedrock/batches/test_handler.py
+++ b/tests/test_litellm/llms/bedrock/batches/test_handler.py
@@ -8,7 +8,7 @@ the tests don't hit AWS.
 
 from __future__ import annotations
 
-from datetime import datetime, timezone
+from datetime import datetime, timedelta, timezone
 from unittest.mock import MagicMock, patch
 
 import pytest
@@ -480,3 +480,93 @@ def test_litellm_cancel_batch_dispatches_to_bedrock(patched_boto3):
 
     fake_client.stop_model_invocation_job.assert_called_once_with(jobIdentifier=JOB_ARN)
     assert batch.status == "cancelled"
+
+
+class _TagGatedSTSClient:
+    """Stands in for STS behind a trust policy that only admits sessions carrying ``tags``."""
+
+    def __init__(self, tags: list[dict[str, str]], access_key_id: str) -> None:
+        self._tags = tags
+        self._access_key_id = access_key_id
+
+    def get_caller_identity(self):
+        return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+    def assume_role(self, **params):
+        from botocore.exceptions import ClientError
+
+        if list(params.get("Tags", ())) != self._tags:
+            raise ClientError(
+                {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                "AssumeRole",
+            )
+        return {
+            "Credentials": {
+                "AccessKeyId": self._access_key_id,
+                "SecretAccessKey": "assumed-secret",
+                "SessionToken": "assumed-session-token",
+                "Expiration": datetime.now(timezone.utc) + timedelta(minutes=30),
+            }
+        }
+
+
+def test_handle_model_invocation_job_status_builds_the_client_from_the_tagged_session(monkeypatch):
+    """Status polling must assume the role with the deployment's session tags, like every other call."""
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+    bedrock_client_kwargs: list[dict] = []
+    fake_bedrock = MagicMock()
+    fake_bedrock.get_model_invocation_job.return_value = _fake_boto3_response()
+
+    def boto3_client(service_name, **kwargs):
+        if service_name == "sts":
+            return _TagGatedSTSClient(tags, "ASIABATCHSTATUSTAGGED")
+        bedrock_client_kwargs.append(kwargs)
+        return fake_bedrock
+
+    with patch("boto3.client", side_effect=boto3_client):
+        batch = BedrockBatchesHandler._handle_model_invocation_job_status(
+            batch_id=JOB_ARN,
+            aws_access_key_id="AKIABATCHSTATUSCALLER",
+            aws_secret_access_key="pod-caller-secret",
+            aws_role_name="arn:aws:iam::999999999999:role/litellm-batch-role",
+            aws_session_name="litellm-batch-session",
+            aws_session_tags=tags,
+        )
+
+    assert batch.status == "completed"
+    assert [kwargs["aws_access_key_id"] for kwargs in bedrock_client_kwargs] == ["ASIABATCHSTATUSTAGGED"]
+
+
+def test_cancel_batch_stops_and_polls_the_job_with_the_tagged_session(monkeypatch):
+    """Cancelling on a tag-gated role must forward the deployment's session tags to both the stop and status calls."""
+    import litellm
+
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+    bedrock_client_kwargs: list[dict] = []
+    fake_bedrock = MagicMock()
+    fake_bedrock.get_model_invocation_job.return_value = _fake_boto3_response(status="Stopped")
+
+    def boto3_client(service_name, **kwargs):
+        if service_name == "sts":
+            return _TagGatedSTSClient(tags, "ASIABATCHCANCELTAGGED")
+        bedrock_client_kwargs.append(kwargs)
+        return fake_bedrock
+
+    with patch("boto3.client", side_effect=boto3_client):
+        batch = litellm.cancel_batch(
+            batch_id=JOB_ARN,
+            custom_llm_provider="bedrock",
+            aws_access_key_id="AKIABATCHCANCELCALLER",
+            aws_secret_access_key="pod-caller-secret",
+            aws_role_name="arn:aws:iam::999999999999:role/litellm-batch-role",
+            aws_session_name="litellm-batch-session",
+            aws_session_tags=tags,
+        )
+
+    fake_bedrock.stop_model_invocation_job.assert_called_once_with(jobIdentifier=JOB_ARN)
+    assert batch.status == "cancelled"
+    assert [kwargs["aws_access_key_id"] for kwargs in bedrock_client_kwargs] == ["ASIABATCHCANCELTAGGED"] * 2
diff --git a/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_amazon_moonshot_transformation.py b/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_amazon_moonshot_transformation.py
index 531f334e460..bcd1df26020 100644
--- a/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_amazon_moonshot_transformation.py
+++ b/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_amazon_moonshot_transformation.py
@@ -15,6 +15,7 @@ AWS_AUTH_PARAMS = {
     "aws_sts_endpoint": "https://sts.us-west-2.amazonaws.com",
     "aws_bedrock_runtime_endpoint": "https://bedrock-runtime.us-west-2.amazonaws.com",
     "aws_external_id": "external",
+    "aws_session_tags": [{"Key": "team", "Value": "genai"}],
 }
 
 
diff --git a/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_base_invoke_transformation.py b/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_base_invoke_transformation.py
index c2c448cd7e2..96a2fa6ec67 100644
--- a/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_base_invoke_transformation.py
+++ b/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_base_invoke_transformation.py
@@ -1,5 +1,7 @@
 import json
+from unittest.mock import MagicMock
 
+import httpx
 import pytest
 
 
@@ -190,3 +192,45 @@ def test_get_error_class_preserves_provider_headers():
     assert isinstance(error, BedrockError)
     assert error.headers == {"x-amzn-RequestId": "req-invoke-500"}
     assert error.response.headers["x-amzn-requestid"] == "req-invoke-500"
+
+
+def test_transform_response_hands_json_mode_to_nova():
+    """The invoke dispatcher forwards its json_mode argument to Nova instead of dropping it."""
+    from litellm.types.utils import ModelResponse
+
+    response_json = {
+        "output": {
+            "message": {
+                "role": "assistant",
+                "content": [
+                    {
+                        "toolUse": {
+                            "toolUseId": "tooluse_nova_json",
+                            "name": "json_tool_call",
+                            "input": {"city": "Paris", "temperature": 21},
+                        }
+                    }
+                ],
+            }
+        },
+        "stopReason": "tool_use",
+        "usage": {"inputTokens": 5, "outputTokens": 4, "totalTokens": 9},
+    }
+    raw_response = httpx.Response(200, json=response_json, request=httpx.Request("POST", "https://bedrock"))
+
+    result = AmazonInvokeConfig().transform_response(
+        model="invoke/amazon.nova-lite-v1:0",
+        raw_response=raw_response,
+        model_response=ModelResponse(),
+        logging_obj=MagicMock(),
+        request_data={},
+        messages=[{"role": "user", "content": "weather"}],
+        optional_params={},
+        litellm_params={},
+        encoding=None,
+        api_key=None,
+        json_mode=True,
+    )
+
+    assert result.choices[0].message.tool_calls is None
+    assert json.loads(result.choices[0].message.content) == {"city": "Paris", "temperature": 21}
diff --git a/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude3_transformation.py b/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude3_transformation.py
index cbf160c451f..bcba4bf7711 100644
--- a/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude3_transformation.py
+++ b/tests/test_litellm/llms/bedrock/chat/invoke_transformations/test_bedrock_chat_invoke_transformations_anthropic_claude3_transformation.py
@@ -57,6 +57,7 @@ def test_aws_params_filtered_from_request_body():
         "aws_sts_endpoint": "https://sts.amazonaws.com",
         "aws_bedrock_runtime_endpoint": "https://bedrock-runtime.us-west-2.amazonaws.com",
         "aws_external_id": "external-id-123",
+        "aws_session_tags": [{"Key": "team", "Value": "genai"}],
     }
 
     # Transform the request
@@ -105,6 +106,9 @@ def test_aws_params_filtered_from_request_body():
     assert (
         "aws_external_id" not in result_json
     ), "AWS external ID should not be in request body"
+    assert (
+        "aws_session_tags" not in result_json
+    ), "AWS session tags should not be in request body"
 
     # Also check that the sensitive values themselves are not in the response
     assert (
diff --git a/tests/test_litellm/llms/bedrock/chat/test_bedrock_converse_handler.py b/tests/test_litellm/llms/bedrock/chat/test_bedrock_converse_handler.py
index f34b8eb1fb9..4c2aa4ec4cf 100644
--- a/tests/test_litellm/llms/bedrock/chat/test_bedrock_converse_handler.py
+++ b/tests/test_litellm/llms/bedrock/chat/test_bedrock_converse_handler.py
@@ -6,16 +6,21 @@ extension, and AWS credential resolution is stubbed so nothing reaches STS.
 
 from __future__ import annotations
 
+import asyncio
+from datetime import datetime, timedelta, timezone
 from unittest.mock import MagicMock, patch
 
+import boto3
 import httpx
 import pytest
 
 from botocore.credentials import Credentials
+from botocore.exceptions import ClientError
 from litellm.llms.bedrock.chat.converse_handler import BedrockConverseLLM
 from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
 from litellm.rust_bridge import chat_completions as bridge
 from litellm.types.utils import ModelResponse
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 RUST_RESPONSE = {
     "created": 1_700_000_000,
@@ -308,7 +313,9 @@ CONVERSE_RESPONSE = {
 }
 
 
-async def _drive_async_completion(*, skip_pre_call_logging: bool, logging_obj):
+async def _drive_async_completion(
+    *, skip_pre_call_logging: bool, logging_obj, credentials: Credentials = RESOLVED_CREDENTIALS
+):
     """Run the real `async_completion` with a stubbed transport."""
     import httpx as _httpx
 
@@ -335,7 +342,7 @@ async def _drive_async_completion(*, skip_pre_call_logging: bool, logging_obj):
         stream=None,
         optional_params={"maxTokens": 16},
         litellm_params={"aws_region_name": "us-west-2"},
-        credentials=RESOLVED_CREDENTIALS,
+        credentials=credentials,
         headers={},
         client=client,
         skip_pre_call_logging=skip_pre_call_logging,
@@ -357,6 +364,23 @@ async def test_async_completion_logs_pre_call_by_default():
     assert logging_obj.pre_call.call_count == 1
 
 
+@pytest.mark.asyncio
+async def test_async_completion_signs_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: botocore refreshes expiring credentials inside SigV4 signing with a
+    blocking HTTP call, so `async_completion` must sign on a worker thread to keep the loop serving."""
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    probe = EventLoopProbe()
+    release = asyncio.create_task(probe.release_refresh_from_the_loop())
+
+    response = await _drive_async_completion(
+        skip_pre_call_logging=False, logging_obj=MagicMock(), credentials=probe.credentials()
+    )
+    await release
+
+    assert response.choices[0].message.content == "hi"
+    assert probe.served_during_refresh is True
+
+
 def _sync_client_returning_converse_response():
     client = MagicMock()
     client.post.side_effect = lambda **_kwargs: httpx.Response(
@@ -541,3 +565,54 @@ def test_bearer_token_auth_never_runs_the_sigv4_credential_chain(monkeypatch, co
 
     assert response.choices[0].message.content == "hi"
     assert client.post.call_args.kwargs["headers"]["Authorization"] == "Bearer bedrock-bearer-token"
+
+
+def test_session_tags_sign_the_request_and_stay_out_of_the_body(monkeypatch):
+    """The tagged STS session signs the Converse call and the tags never reach the request body (#34069)."""
+    monkeypatch.setenv("LITELLM_RUST", "0")
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+
+    class FakeSTSClient:
+        def get_caller_identity(self):
+            return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+        def assume_role(self, **params):
+            if list(params.get("Tags", ())) != tags:
+                raise ClientError(
+                    {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                    "AssumeRole",
+                )
+            return {
+                "Credentials": {
+                    "AccessKeyId": "ASIACONVERSETAGGED",
+                    "SecretAccessKey": "assumed-secret",
+                    "SessionToken": "assumed-session-token",
+                    "Expiration": datetime.now(timezone.utc) + timedelta(minutes=30),
+                }
+            }
+
+    client = _sync_client_returning_converse_response()
+    with patch.object(boto3, "client", return_value=FakeSTSClient()):
+        response = BedrockConverseLLM().completion(
+            **_completion_kwargs(
+                optional_params={
+                    "maxTokens": 16,
+                    "aws_region_name": "us-east-1",
+                    "aws_access_key_id": "AKIACONVERSECALLER",
+                    "aws_secret_access_key": "pod-caller-secret",
+                    "aws_role_name": "arn:aws:iam::999999999999:role/litellm-converse-role",
+                    "aws_session_name": "litellm-converse-session",
+                    "aws_session_tags": tags,
+                },
+                litellm_params={},
+                client=client,
+            )
+        )
+
+    assert response.choices[0].message.content == "hi"
+    sent = client.post.call_args.kwargs
+    assert "Credential=ASIACONVERSETAGGED/" in sent["headers"]["Authorization"]
+    assert "aws_session_tags" not in sent["data"]
diff --git a/tests/test_litellm/llms/bedrock/chat/test_converse_transformation.py b/tests/test_litellm/llms/bedrock/chat/test_converse_transformation.py
index f0e361ceb88..2e9ea90f3b8 100644
--- a/tests/test_litellm/llms/bedrock/chat/test_converse_transformation.py
+++ b/tests/test_litellm/llms/bedrock/chat/test_converse_transformation.py
@@ -382,6 +382,8 @@ def test_reasoning_with_forced_tool_choice_switches_to_auto():
         "us.openai.gpt-5.6-sol",
         "global.openai.gpt-5.6-terra",
         "bedrock/converse/us.openai.gpt-5.6-luna",
+        "us.openai.gpt-6-astra",
+        "bedrock/converse/global.openai.gpt-6-astra",
     ],
 )
 def test_reasoning_effort_maps_to_reasoning_effort_for_openai_gpt5_converse(model, local_model_cost_map):
@@ -412,6 +414,7 @@ def test_reasoning_effort_maps_to_reasoning_effort_for_openai_gpt5_converse(mode
     [
         "us.openai.gpt-5.6-sol",
         "bedrock/converse/global.openai.gpt-5.6-luna",
+        "us.openai.gpt-6-astra",
     ],
 )
 def test_openai_gpt5_converse_never_forwards_thinking(model, local_model_cost_map):
@@ -863,6 +866,191 @@ def test_get_supported_openai_params():
     assert "reasoning_effort" in supported_params
 
 
+@pytest.mark.parametrize(
+    "model",
+    [
+        "bedrock/us.deepseek.r1-v1:0",
+        "bedrock/converse/us.deepseek.r1-v1:0",
+        "bedrock/deepseek.v3-v1:0",
+        "bedrock/deepseek.v3.2",
+    ],
+)
+def test_bedrock_deepseek_does_not_advertise_thinking(model):
+    """DeepSeek reasons natively on Bedrock and does not take the Anthropic-shaped `thinking`
+    field (R1 400s on it, V3 ignores it), so it must not be advertised as supported."""
+    config = AmazonConverseConfig()
+    supported_params = config.get_supported_openai_params(model=model)
+    assert "thinking" not in supported_params
+    assert "output_config" not in supported_params
+
+
+@pytest.mark.parametrize("model", ["bedrock/us.deepseek.r1-v1:0", "bedrock/converse/us.deepseek.r1-v1:0"])
+def test_bedrock_deepseek_r1_does_not_advertise_reasoning_effort(model):
+    """DeepSeek R1 always reasons and returns a 400 for any reasoning_effort shape."""
+    config = AmazonConverseConfig()
+    assert "reasoning_effort" not in config.get_supported_openai_params(model=model)
+
+
+@pytest.mark.parametrize("model", ["bedrock/deepseek.v3-v1:0", "bedrock/deepseek.v3.2", "bedrock/us.deepseek.v3.2"])
+def test_bedrock_deepseek_v3_advertises_reasoning_effort(model):
+    """DeepSeek V3 on Bedrock accepts a raw reasoning_effort in additionalModelRequestFields."""
+    config = AmazonConverseConfig()
+    assert "reasoning_effort" in config.get_supported_openai_params(model=model)
+
+
+@pytest.mark.parametrize("model", ["us.deepseek.r1-v1:0", "deepseek.v3.2"])
+def test_bedrock_deepseek_thinking_raises_without_drop_params(model):
+    """Passing `thinking` to Bedrock DeepSeek must fail client-side with a clear
+    UnsupportedParamsError instead of leaking through to Bedrock."""
+    with pytest.raises(litellm.UnsupportedParamsError):
+        litellm.utils.get_optional_params(
+            model=model,
+            custom_llm_provider="bedrock",
+            thinking={"type": "enabled", "budget_tokens": 1024},
+        )
+
+
+def test_bedrock_deepseek_r1_reasoning_effort_raises_without_drop_params():
+    with pytest.raises(litellm.UnsupportedParamsError):
+        litellm.utils.get_optional_params(
+            model="us.deepseek.r1-v1:0",
+            custom_llm_provider="bedrock",
+            reasoning_effort="high",
+        )
+
+
+@pytest.mark.parametrize("model", ["us.deepseek.r1-v1:0", "deepseek.v3.2"])
+def test_bedrock_deepseek_thinking_dropped_does_not_leak_into_request(model):
+    """With drop_params, `thinking` is dropped rather than forwarded into
+    additionalModelRequestFields for Bedrock DeepSeek."""
+    optional_params = litellm.utils.get_optional_params(
+        model=model,
+        custom_llm_provider="bedrock",
+        thinking={"type": "enabled", "budget_tokens": 1024},
+        drop_params=True,
+    )
+    assert "thinking" not in optional_params
+
+    config = AmazonConverseConfig()
+    request = config._transform_request(
+        model=f"bedrock/converse/{model}",
+        messages=[{"role": "user", "content": "Say hi in one word."}],
+        optional_params=optional_params,
+        litellm_params={},
+        headers={},
+    )
+    assert "thinking" not in (request.get("additionalModelRequestFields") or {})
+
+
+@pytest.mark.parametrize("param", ["thinking", "reasoning_effort"])
+def test_bedrock_deepseek_r1_reasoning_params_not_forwarded_by_map(param):
+    """Even when map_openai_params is called directly (bypassing the supported-params
+    gate), DeepSeek R1 must not forward thinking/reasoning_effort into
+    additionalModelRequestFields, since Bedrock rejects both with a 400."""
+    config = AmazonConverseConfig()
+    model = "bedrock/converse/us.deepseek.r1-v1:0"
+    value = {"type": "enabled", "budget_tokens": 1024} if param == "thinking" else "high"
+
+    optional_params = config.map_openai_params(
+        non_default_params={param: value, "max_tokens": 100},
+        optional_params={},
+        model=model,
+        drop_params=False,
+    )
+    assert "thinking" not in optional_params
+    assert "reasoning_effort" not in optional_params
+
+    request = config._transform_request(
+        model=model,
+        messages=[{"role": "user", "content": "Say hi in one word."}],
+        optional_params=optional_params,
+        litellm_params={},
+        headers={},
+    )
+    assert request.get("additionalModelRequestFields") is None
+
+
+def test_bedrock_deepseek_v3_reasoning_effort_forwarded_raw():
+    """DeepSeek V3 takes reasoning_effort verbatim in additionalModelRequestFields, never
+    converted into the Anthropic `thinking` block that Claude models get."""
+    config = AmazonConverseConfig()
+    model = "bedrock/deepseek.v3.2"
+    optional_params = config.map_openai_params(
+        non_default_params={"reasoning_effort": "high", "max_tokens": 100},
+        optional_params={},
+        model=model,
+        drop_params=False,
+    )
+    assert "thinking" not in optional_params
+
+    request = config._transform_request(
+        model=model,
+        messages=[{"role": "user", "content": "Say hi in one word."}],
+        optional_params=optional_params,
+        litellm_params={},
+        headers={},
+    )
+    assert request["additionalModelRequestFields"] == {"reasoning_effort": "high"}
+
+
+def test_bedrock_deepseek_v3_thinking_dropped_by_map():
+    config = AmazonConverseConfig()
+    optional_params = config.map_openai_params(
+        non_default_params={"thinking": {"type": "enabled", "budget_tokens": 1024}, "max_tokens": 100},
+        optional_params={},
+        model="bedrock/deepseek.v3.2",
+        drop_params=False,
+    )
+    assert "thinking" not in optional_params
+    assert "reasoning_effort" not in optional_params
+
+
+@pytest.mark.parametrize(
+    "model, param, value, kept_key",
+    [
+        (
+            "bedrock/us.anthropic.claude-opus-4-20250514-v1:0",
+            "thinking",
+            {"type": "enabled", "budget_tokens": 1024},
+            "thinking",
+        ),
+        (
+            "bedrock/arn:aws:bedrock:us-east-1:123456789012:application-inference-profile/abc123",
+            "thinking",
+            {"type": "enabled", "budget_tokens": 1024},
+            "thinking",
+        ),
+        (
+            "bedrock/openai.gpt-oss-safeguard-20b-1:0",
+            "reasoning_effort",
+            "high",
+            "reasoning_effort",
+        ),
+        (
+            "bedrock/us.amazon.nova-2-lite-v1:0",
+            "reasoning_effort",
+            "high",
+            "reasoningConfig",
+        ),
+    ],
+)
+def test_bedrock_non_deepseek_reasoning_params_preserved(model, param, value, kept_key):
+    """The DeepSeek leak fix must only drop reasoning request params for DeepSeek.
+
+    Claude behind an application-inference-profile ARN, gpt-oss-safeguard (absent from the
+    cost map so `supports_reasoning` is False), and Nova 2 all reason via a request param and
+    must keep it. Regression guard against gating the drop on a positive allowlist, which
+    silently degraded reasoning for anything the allowlist/ARN introspection missed."""
+    config = AmazonConverseConfig()
+    optional_params = config.map_openai_params(
+        non_default_params={param: value, "max_tokens": 100},
+        optional_params={},
+        model=model,
+        drop_params=False,
+    )
+    assert kept_key in optional_params
+
+
 def test_get_supported_openai_params_bedrock_converse():
     """
     Test that all documented bedrock converse models have the same set of supported openai params when using
@@ -6727,3 +6915,41 @@ def test_forced_tool_choice_forwarded_on_converse_models_that_support_it(
     )
 
     assert result == {"any": {}}
+
+
+def test_transform_response_honors_json_mode_kwarg_when_optional_params_lack_it():
+    response_json = {
+        "metrics": {"latencyMs": 900},
+        "output": {
+            "message": {
+                "content": [
+                    {
+                        "toolUse": {
+                            "input": {"city": "Paris", "population": 2100000},
+                            "name": "json_tool_call",
+                            "toolUseId": "tooluse_invoke_nova_json",
+                        }
+                    }
+                ],
+                "role": "assistant",
+            }
+        },
+        "stopReason": "tool_use",
+        "usage": {"inputTokens": 40, "outputTokens": 20, "totalTokens": 60},
+    }
+    raw_response = httpx.Response(200, json=response_json, request=httpx.Request("POST", "https://bedrock.test"))
+    logging_obj = MagicMock()
+    result = AmazonConverseConfig().transform_response(
+        model="bedrock/invoke/us.amazon.nova-micro-v1:0",
+        raw_response=raw_response,
+        model_response=ModelResponse(),
+        logging_obj=logging_obj,
+        request_data={},
+        messages=[],
+        optional_params={"tools": [{"type": "function", "function": {"name": "json_tool_call", "parameters": {}}}]},
+        litellm_params={},
+        encoding=None,
+        json_mode=True,
+    )
+    assert result.choices[0].message.tool_calls is None
+    assert json.loads(result.choices[0].message.content) == {"city": "Paris", "population": 2100000}
diff --git a/tests/test_litellm/llms/bedrock/count_tokens/test_bedrock_count_tokens_handler.py b/tests/test_litellm/llms/bedrock/count_tokens/test_bedrock_count_tokens_handler.py
new file mode 100644
index 00000000000..3622ce7f212
--- /dev/null
+++ b/tests/test_litellm/llms/bedrock/count_tokens/test_bedrock_count_tokens_handler.py
@@ -0,0 +1,54 @@
+import asyncio
+from unittest.mock import AsyncMock
+
+import httpx
+import pytest
+from botocore.credentials import RefreshableCredentials
+
+from litellm.llms.bedrock.count_tokens.handler import BedrockCountTokensHandler
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
+
+
+class _ProbedCountTokensHandler(BedrockCountTokensHandler):
+    def __init__(self, probe: EventLoopProbe) -> None:
+        super().__init__()
+        self._probe = probe
+
+    def get_credentials(
+        self,
+        **kwargs: object,  # kwargs-ok: mirrors the base resolver's keyword contract, which the probe ignores
+    ) -> RefreshableCredentials:
+        return self._probe.credentials()
+
+
+@pytest.mark.asyncio
+async def test_handle_count_tokens_request_signs_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: the count_tokens handler signed on the loop, so botocore's blocking
+    credential refresh inside SigV4 stalled every other request on the worker."""
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    probe = EventLoopProbe()
+    client = AsyncMock(spec=AsyncHTTPHandler)
+    client.post = AsyncMock(
+        return_value=httpx.Response(
+            200,
+            json={"inputTokens": 7},
+            request=httpx.Request("POST", "https://bedrock-runtime.us-west-2.amazonaws.com/"),
+        )
+    )
+    release = asyncio.create_task(probe.release_refresh_from_the_loop())
+
+    result = await _ProbedCountTokensHandler(probe).handle_count_tokens_request(
+        request_data={
+            "model": "us.anthropic.claude-haiku-4-5-20251001-v1:0",
+            "messages": [{"role": "user", "content": "hi"}],
+        },
+        litellm_params={"aws_region_name": "us-west-2"},
+        resolved_model="us.anthropic.claude-haiku-4-5-20251001-v1:0",
+        client=client,
+    )
+    await release
+
+    assert result == {"input_tokens": 7}
+    assert client.post.call_args.kwargs["headers"]["Authorization"].startswith("AWS4-HMAC-SHA256")
+    assert probe.served_during_refresh is True
diff --git a/tests/test_litellm/llms/bedrock/embed/test_bedrock_async_invoke_embedding.py b/tests/test_litellm/llms/bedrock/embed/test_bedrock_async_invoke_embedding.py
index ddbd3a2e9ba..18f4b0f6ced 100644
--- a/tests/test_litellm/llms/bedrock/embed/test_bedrock_async_invoke_embedding.py
+++ b/tests/test_litellm/llms/bedrock/embed/test_bedrock_async_invoke_embedding.py
@@ -1,11 +1,15 @@
 import json
+import asyncio
 from unittest.mock import Mock, patch
 
+import httpx
 import pytest
+import respx
 
 import litellm
 from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
 from litellm.types.llms.base import HiddenParams
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 # Mock async invoke responses
 async_invoke_response = {
@@ -422,3 +426,34 @@ class TestBedrockAsyncInvokeEmbedding:
                 async_endpoint
                 == "https://bedrock-runtime.us-east-1.amazonaws.com/async-invoke"
             )
+
+
+@pytest.mark.asyncio
+async def test_async_invoke_status_signs_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: the GetAsyncInvoke poll is a signed GET, and botocore refreshes
+    expiring credentials inside that signing with a blocking HTTP call, so it must run on a worker
+    thread to keep the loop serving other requests."""
+    from litellm.llms.bedrock.embed.embedding import BedrockEmbedding
+
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    litellm.in_memory_llm_clients_cache.flush_cache()
+    embedder = BedrockEmbedding()
+    probe = EventLoopProbe()
+
+    with (
+        patch.object(embedder, "_load_credentials", return_value=(probe.credentials(), "us-east-1")),
+        respx.mock,
+    ):
+        route = respx.get(url__regex=r"https://bedrock-runtime\.us-east-1\.amazonaws\.com/async-invoke/.*").mock(
+            return_value=httpx.Response(200, json=async_invoke_status_response)
+        )
+        release = asyncio.create_task(probe.release_refresh_from_the_loop())
+        status = await embedder._get_async_invoke_status(
+            invocation_arn=async_invoke_status_response["invocationArn"], aws_region_name="us-east-1"
+        )
+        await release
+
+    assert status["status"] == "InProgress"
+    assert "Authorization" in route.calls.last.request.headers
+    assert probe.served_during_refresh is True
diff --git a/tests/test_litellm/llms/bedrock/embed/test_bedrock_embedding.py b/tests/test_litellm/llms/bedrock/embed/test_bedrock_embedding.py
index bcd1a29d0e8..e5a460e2f1a 100644
--- a/tests/test_litellm/llms/bedrock/embed/test_bedrock_embedding.py
+++ b/tests/test_litellm/llms/bedrock/embed/test_bedrock_embedding.py
@@ -1,12 +1,17 @@
 import json
+import asyncio
 import os
 from unittest.mock import Mock, patch
+from unittest.mock import AsyncMock, MagicMock
 
 import pytest
+import httpx
 
 import litellm
 from litellm.llms.bedrock.embed.twelvelabs_marengo_transformation import TwelveLabsMarengoEmbeddingConfig
 from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
+from litellm.llms.bedrock.embed.embedding import BedrockEmbedding
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 # Mock responses for different embedding models
 titan_embedding_response = {"embedding": [0.1, 0.2, 0.3], "inputTextTokenCount": 10}
@@ -1036,6 +1041,63 @@ def test_load_credentials_assumes_role_with_external_id(monkeypatch):
     assert "aws_external_id" not in optional_params
 
 
+def test_embedding_session_tags_sign_the_request_and_stay_out_of_the_body(monkeypatch):
+    """The tagged STS session signs the InvokeModel call and the tags never reach the body (#34069)."""
+    import datetime
+
+    import boto3
+    from botocore.exceptions import ClientError
+
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+
+    class FakeSTSClient:
+        def get_caller_identity(self):
+            return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+        def assume_role(self, **params):
+            if list(params.get("Tags", ())) != tags:
+                raise ClientError(
+                    {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                    "AssumeRole",
+                )
+            return {
+                "Credentials": {
+                    "AccessKeyId": "ASIAEMBEDTAGGED",
+                    "SecretAccessKey": "assumed-secret",
+                    "SessionToken": "assumed-session-token",
+                    "Expiration": datetime.datetime.now(datetime.timezone.utc) + datetime.timedelta(minutes=30),
+                }
+            }
+
+    client = HTTPHandler()
+    with patch.object(boto3, "client", return_value=FakeSTSClient()), patch.object(client, "post") as mock_post:
+        mock_response = Mock()
+        mock_response.status_code = 200
+        mock_response.text = json.dumps(titan_embedding_response)
+        mock_response.json = lambda: json.loads(mock_response.text)
+        mock_post.return_value = mock_response
+
+        response = litellm.embedding(
+            model="bedrock/amazon.titan-embed-text-v1",
+            input=test_input,
+            client=client,
+            aws_region_name="us-east-1",
+            aws_access_key_id="AKIAEMBEDCALLERKEY",
+            aws_secret_access_key="pod-caller-secret",
+            aws_role_name="arn:aws:iam::999999999999:role/litellm-embed-role",
+            aws_session_name="litellm-embed-session",
+            aws_session_tags=tags,
+        )
+
+    assert response.data[0]["embedding"] == titan_embedding_response["embedding"]
+    sent = mock_post.call_args.kwargs
+    assert "Credential=ASIAEMBEDTAGGED/" in sent["headers"]["Authorization"]
+    assert "aws_session_tags" not in sent["data"]
+
+
 def test_bedrock_embedding_bearer_token_never_runs_the_sigv4_credential_chain(monkeypatch):
     """The deployment's AWS profile does not exist, so resolving SigV4 credentials
     raises; a bearer-token deployment must still serve the request, since the
@@ -1062,6 +1124,41 @@ def test_bedrock_embedding_bearer_token_never_runs_the_sigv4_credential_chain(mo
     assert mock_post.call_args.kwargs["headers"]["Authorization"] == "Bearer env-bearer-token-12345"
 
 
+@pytest.mark.asyncio
+async def test_async_single_func_embeddings_signs_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: Titan, Nova, and TwelveLabs embeddings sign one SigV4 request per
+    input, and botocore refreshes expiring credentials inside that signing with a blocking HTTP call,
+    so each signing must run on a worker thread to keep the loop serving other requests."""
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    probe = EventLoopProbe()
+    client = MagicMock()
+    client.__class__ = AsyncHTTPHandler
+    client.post = AsyncMock(
+        return_value=httpx.Response(
+            200,
+            json=titan_embedding_response,
+            request=httpx.Request("POST", "https://bedrock-runtime.us-west-2.amazonaws.com"),
+        )
+    )
+
+    release = asyncio.create_task(probe.release_refresh_from_the_loop())
+    response = await BedrockEmbedding()._async_single_func_embeddings(
+        client=client,
+        timeout=None,
+        batch_data=[{"inputText": test_input}],
+        credentials=probe.credentials(),
+        extra_headers=None,
+        endpoint_url="https://bedrock-runtime.us-west-2.amazonaws.com/model/amazon.titan-embed-text-v1/invoke",
+        aws_region_name="us-west-2",
+        model="amazon.titan-embed-text-v1",
+        logging_obj=MagicMock(),
+        provider="amazon",
+    )
+    await release
+
+    assert response.data[0]["embedding"] == titan_embedding_response["embedding"]
+    assert "Authorization" in client.post.call_args.kwargs["headers"]
+    assert probe.served_during_refresh is True
 marengo_3_embedding_response = {"data": [{"embedding": [0.01 * i for i in range(512)]}]}
 MARENGO_3_DUCK = "data:image/png;base64,ZHVjaw=="
 
diff --git a/tests/test_litellm/llms/bedrock/event_loop_probe.py b/tests/test_litellm/llms/bedrock/event_loop_probe.py
new file mode 100644
index 00000000000..c347247ec32
--- /dev/null
+++ b/tests/test_litellm/llms/bedrock/event_loop_probe.py
@@ -0,0 +1,57 @@
+"""Refreshable credentials whose refresh only completes while the event loop keeps serving."""
+
+from __future__ import annotations
+
+import asyncio
+import threading
+import time
+from datetime import datetime, timedelta, timezone
+from typing import Final
+
+from botocore.credentials import RefreshableCredentials
+
+REFRESH_RELEASE_TIMEOUT_SECONDS: Final = 2.0
+REFRESH_START_TIMEOUT_SECONDS: Final = 10.0
+
+
+class EventLoopProbe:
+    """Blocks inside botocore's credential refresh until a coroutine on the loop releases it.
+
+    Signing on the event loop thread can never be released, so `served_during_refresh` reads False there
+    and True only when the refresh ran on another thread while the loop stayed responsive.
+    """
+
+    def __init__(self) -> None:
+        self.refresh_started: Final = threading.Event()
+        self.loop_served: Final = threading.Event()
+        self.served_during_refresh: bool | None = None
+
+    def refresh(self) -> dict[str, str | None]:
+        self.refresh_started.set()
+        served: Final = self.loop_served.wait(timeout=REFRESH_RELEASE_TIMEOUT_SECONDS)
+        if self.served_during_refresh is None:
+            self.served_during_refresh = served
+        return {
+            "access_key": "AKIAREFRESHED",
+            "secret_key": "refreshed-secret",
+            "token": None,
+            "expiry_time": (datetime.now(timezone.utc) + timedelta(hours=1)).isoformat(),
+        }
+
+    def credentials(self) -> RefreshableCredentials:
+        return RefreshableCredentials(
+            access_key="AKIASTALE",
+            secret_key="stale-secret",
+            token=None,
+            expiry_time=datetime.now(timezone.utc) + timedelta(seconds=60),
+            refresh_using=self.refresh,
+            method="event-loop-probe",
+        )
+
+    async def release_refresh_from_the_loop(self) -> None:
+        deadline: Final = time.monotonic() + REFRESH_START_TIMEOUT_SECONDS
+        while not self.refresh_started.is_set():
+            if time.monotonic() > deadline:
+                raise TimeoutError("signing finished without ever starting a credential refresh")
+            await asyncio.sleep(0.005)
+        self.loop_served.set()
diff --git a/tests/test_litellm/llms/bedrock/files/test_bedrock_files_transformation.py b/tests/test_litellm/llms/bedrock/files/test_bedrock_files_transformation.py
index 541c0db15d8..3b01a4f2054 100644
--- a/tests/test_litellm/llms/bedrock/files/test_bedrock_files_transformation.py
+++ b/tests/test_litellm/llms/bedrock/files/test_bedrock_files_transformation.py
@@ -5,6 +5,8 @@ Test bedrock files transformation functionality
 import json
 import os
 from collections.abc import Mapping
+from contextlib import AsyncExitStack, closing
+from typing import Final
 from unittest.mock import MagicMock
 from urllib.parse import unquote, urlparse
 
@@ -1855,6 +1857,104 @@ class TestBedrockBatchNonChatEndpointRecords:
         ]
 
 
+class TestBedrockFileDeletion:
+    S3_URI: Final = "s3://my-bucket/litellm-bedrock-files-model-abc.jsonl"
+    URL: Final = "https://s3.us-west-2.amazonaws.com/my-bucket/litellm-bedrock-files-model-abc.jsonl"
+
+    def test_interleaved_deletions_keep_their_own_file_ids(self, monkeypatch: pytest.MonkeyPatch) -> None:
+        import httpx
+
+        from litellm.llms.bedrock.files.transformation import BedrockFilesConfig
+
+        monkeypatch.setenv("AWS_S3_BUCKET_NAME", "my-bucket")
+        config: Final = BedrockFilesConfig()
+        params: Final = {
+            "aws_access_key_id": "AKIAEXAMPLE",
+            "aws_secret_access_key": "test-secret",
+            "aws_region_name": "us-west-2",
+        }
+        file_ids: Final = (self.S3_URI, "s3://my-bucket/litellm-bedrock-files-model-second.jsonl")
+        for file_id in file_ids:
+            config.transform_delete_file_request(file_id=file_id, optional_params={}, litellm_params=params)
+
+        deleted: Final = tuple(
+            config.transform_delete_file_response(
+                raw_response=httpx.Response(204),
+                logging_obj=MagicMock(model_call_details={"additional_args": {"file_id": file_id}}),
+                litellm_params=params,
+            ).id
+            for file_id in file_ids
+        )
+
+        assert deleted == file_ids
+
+    def test_delete_file_sends_signed_delete_and_returns_matching_id(self, monkeypatch: pytest.MonkeyPatch) -> None:
+        import httpx
+        import respx
+
+        import litellm
+        from litellm.llms.custom_httpx.http_handler import HTTPHandler
+
+        monkeypatch.setenv("AWS_S3_BUCKET_NAME", "my-bucket")
+        with respx.mock, closing(HTTPHandler()) as client:
+            route: Final = respx.delete(self.URL).mock(return_value=httpx.Response(204))
+            deleted: Final = litellm.file_delete(
+                file_id=self.S3_URI, custom_llm_provider="bedrock", client=client,
+                aws_access_key_id="AKIAEXAMPLE", aws_secret_access_key="test-secret", aws_region_name="us-west-2",
+            )
+        assert route.call_count == 1
+        request: Final = route.calls[0].request
+        assert request.content == b""
+        signed: Final = AWSRequest(method="DELETE", url=self.URL, headers={
+            "X-Amz-Date": request.headers["X-Amz-Date"],
+            "X-Amz-Content-SHA256": request.headers["X-Amz-Content-SHA256"],
+        })
+        signed.context["timestamp"] = request.headers["X-Amz-Date"]
+        auth: Final = S3SigV4Auth(Credentials("AKIAEXAMPLE", "test-secret"), "s3", "us-west-2")
+        signature: Final = auth.signature(auth.string_to_sign(signed, auth.canonical_request(signed)), signed)
+        assert request.headers["Authorization"].endswith(f"Signature={signature}")
+        assert deleted.id == self.S3_URI and deleted.deleted is True
+
+    @pytest.mark.asyncio
+    async def test_adelete_file_propagates_s3_errors(self, monkeypatch: pytest.MonkeyPatch) -> None:
+        import httpx
+        import respx
+
+        import litellm
+        from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
+
+        monkeypatch.setenv("AWS_S3_BUCKET_NAME", "my-bucket")
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        async with AsyncExitStack() as stack:
+            client: Final = AsyncHTTPHandler()
+            stack.push_async_callback(client.close)
+            with respx.mock:
+                route: Final = respx.delete(self.URL).mock(
+                    return_value=httpx.Response(403, content=b"<Error><Code>AccessDenied</Code></Error>")
+                )
+                from litellm.llms.bedrock.common_utils import BedrockError
+
+                with pytest.raises(BedrockError, match="AccessDenied"):
+                    await litellm.afile_delete(
+                        file_id=self.S3_URI, custom_llm_provider="bedrock", client=client,
+                        aws_access_key_id="AKIAEXAMPLE", aws_secret_access_key="test-secret", aws_region_name="us-west-2",
+                    )
+        assert route.call_count == 1
+
+    @pytest.mark.parametrize("file_id, message", [
+        ("s3://other-bucket/litellm-bedrock-files-model-abc.jsonl", "configured storage bucket"),
+        ("s3://my-bucket/private/data.jsonl", "LiteLLM-managed"),
+    ])
+    def test_delete_rejects_untrusted_objects_before_signing(
+        self, file_id: str, message: str, monkeypatch: pytest.MonkeyPatch
+    ) -> None:
+        from litellm.llms.bedrock.files.transformation import BedrockFilesConfig
+
+        monkeypatch.setenv("AWS_S3_BUCKET_NAME", "my-bucket")
+        with pytest.raises(ValueError, match=message):
+            BedrockFilesConfig().transform_delete_file_request(file_id=file_id, optional_params={}, litellm_params={})
+
+
 class TestBedrockFileContentTransformation:
     """SigV4-signed S3 GetObject retrieval of Bedrock batch output files."""
 
@@ -1873,7 +1973,7 @@ class TestBedrockFileContentTransformation:
         import hashlib
 
         from litellm.llms.bedrock.files.transformation import (
-            S3_SIGNED_GET_HEADERS_PARAM,
+            S3_SIGNED_REQUEST_HEADERS_PARAM,
             BedrockFilesConfig,
         )
 
@@ -1889,7 +1989,7 @@ class TestBedrockFileContentTransformation:
         assert url == self.EXPECTED_URL
         assert params == {}
 
-        signed_headers = litellm_params[S3_SIGNED_GET_HEADERS_PARAM]
+        signed_headers = litellm_params[S3_SIGNED_REQUEST_HEADERS_PARAM]
         content_hashes = {
             value
             for name, value in signed_headers.items()
@@ -2139,7 +2239,7 @@ class TestBedrockFileContentTransformation:
     def test_s3_region_name_wins_for_content_signing(self, monkeypatch):
         """s3_region_name must override aws_region_name for both the URL and the signature."""
         from litellm.llms.bedrock.files.transformation import (
-            S3_SIGNED_GET_HEADERS_PARAM,
+            S3_SIGNED_REQUEST_HEADERS_PARAM,
             BedrockFilesConfig,
         )
 
@@ -2154,17 +2254,17 @@ class TestBedrockFileContentTransformation:
         )
 
         assert url.startswith("https://s3.eu-west-1.amazonaws.com/")
-        authorization = litellm_params[S3_SIGNED_GET_HEADERS_PARAM]["Authorization"]
+        authorization = litellm_params[S3_SIGNED_REQUEST_HEADERS_PARAM]["Authorization"]
         assert "/eu-west-1/s3/aws4_request" in authorization
 
     def test_validate_environment_merges_and_pops_signed_get_headers(self):
         from litellm.llms.bedrock.files.transformation import (
-            S3_SIGNED_GET_HEADERS_PARAM,
+            S3_SIGNED_REQUEST_HEADERS_PARAM,
             BedrockFilesConfig,
         )
 
         litellm_params = {
-            S3_SIGNED_GET_HEADERS_PARAM: {"Authorization": "AWS4-HMAC-SHA256 test"}
+            S3_SIGNED_REQUEST_HEADERS_PARAM: {"Authorization": "AWS4-HMAC-SHA256 test"}
         }
 
         headers = BedrockFilesConfig().validate_environment(
@@ -2179,7 +2279,7 @@ class TestBedrockFileContentTransformation:
             "x-custom": "kept",
             "Authorization": "AWS4-HMAC-SHA256 test",
         }
-        assert S3_SIGNED_GET_HEADERS_PARAM not in litellm_params
+        assert S3_SIGNED_REQUEST_HEADERS_PARAM not in litellm_params
 
     def test_transform_file_content_response_wraps_binary_content(self):
         import httpx
@@ -2379,7 +2479,7 @@ class TestBedrockFilesS3SignatureEncoding:
         self, monkeypatch: pytest.MonkeyPatch
     ) -> None:
         from litellm.llms.bedrock.files.transformation import (
-            S3_SIGNED_GET_HEADERS_PARAM,
+            S3_SIGNED_REQUEST_HEADERS_PARAM,
             BedrockFilesConfig,
         )
 
@@ -2402,7 +2502,7 @@ class TestBedrockFilesS3SignatureEncoding:
             method="GET",
             url=url,
             body=None,
-            headers=litellm_params[S3_SIGNED_GET_HEADERS_PARAM],
+            headers=litellm_params[S3_SIGNED_REQUEST_HEADERS_PARAM],
         )
 
 
@@ -2457,7 +2557,7 @@ def test_sign_s3_request_assumes_role_with_external_id(monkeypatch):
     assert "ASIAFILESPUTROLE" in authorization
 
 
-def test_sign_s3_get_request_assumes_role_with_external_id(monkeypatch):
+def test_sign_s3_request_without_body_assumes_role_with_external_id(monkeypatch):
     """A trust policy requiring sts:ExternalId must be satisfied when signing the S3 download request."""
     import datetime
     from unittest.mock import patch
@@ -2504,7 +2604,7 @@ def test_sign_s3_get_request_assumes_role_with_external_id(monkeypatch):
     assert request_params.aws_external_id == "external-id-files-get"
 
     with patch.object(boto3, "client", return_value=FakeSTSClient()):
-        signed_headers = BedrockFilesConfig()._sign_s3_get_request(
+        signed_headers = BedrockFilesConfig()._sign_s3_request_without_body(
             api_base="https://s3.us-east-1.amazonaws.com/safe-bucket/litellm-bedrock-files-model-id-abc.jsonl",
             aws_region_name="us-east-1",
             request_params=request_params,
diff --git a/tests/test_litellm/llms/bedrock/test_base_aws_llm.py b/tests/test_litellm/llms/bedrock/test_base_aws_llm.py
index f854d806bdc..c5b8e7ecc9d 100644
--- a/tests/test_litellm/llms/bedrock/test_base_aws_llm.py
+++ b/tests/test_litellm/llms/bedrock/test_base_aws_llm.py
@@ -1,4 +1,6 @@
+import asyncio
 import json
+from concurrent.futures import ThreadPoolExecutor
 import os
 import threading
 import time
@@ -15,14 +17,17 @@ from unittest.mock import MagicMock, patch
 from botocore.awsrequest import AWSPreparedRequest, AWSRequest
 from botocore.auth import SigV4Auth
 from botocore.credentials import Credentials
-from botocore.exceptions import NoCredentialsError
+from botocore.exceptions import ClientError, NoCredentialsError
 
 import litellm
 from litellm.llms.bedrock.base_aws_llm import (
     AwsAuthError,
     BaseAWSLLM,
     Boto3CredentialsInfo,
+    run_aws_signing,
+    sign_request_off_loop_if_aws,
 )
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 # Global variable for the base_aws_llm.py file path
 
@@ -38,6 +43,14 @@ def flush_shared_bedrock_iam_cache():
     yield
 
 
+@pytest.fixture(autouse=True)
+def _clean_ssl_env(monkeypatch):
+    """get_ssl_verify reads these, so the sts client's verify= would otherwise depend on
+    the ambient environment. The published images set SSL_CERT_FILE."""
+    for env_var in ("SSL_CERT_FILE", "SSL_VERIFY"):
+        monkeypatch.delenv(env_var, raising=False)
+
+
 def test_base_aws_llm_instances_share_process_wide_iam_cache():
     """Regression LIT-2662: new instances must reuse iam_cache (Bedrock passthrough is per-request)."""
     first = BaseAWSLLM()
@@ -2395,6 +2408,283 @@ def test_assume_role_without_external_id():
         )
 
 
+_SESSION_TAGS = ({"Key": "team", "Value": "genai"}, {"Key": "env", "Value": "prod"})
+_SORTED_SESSION_TAGS = ({"Key": "env", "Value": "prod"}, {"Key": "team", "Value": "genai"})
+_TAGGED_ROLE_ARN = "arn:aws:iam::123456789012:role/TaggedRole"
+
+
+class _TagAwareSTSClient:
+    """STS stand-in for a trust policy that only admits sessions carrying exactly the expected tags."""
+
+    def __init__(self, expected_tags: tuple = (), access_key: str = "ASIATAGGEDSESSION") -> None:
+        self.expected_tags = expected_tags
+        self.access_key = access_key
+        self.assume_role_calls: list = []
+
+    def get_caller_identity(self):
+        return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+    def assume_role_with_web_identity(self, **params):
+        return {
+            "Credentials": {
+                "AccessKeyId": "ASIAIRSATEMP",
+                "SecretAccessKey": "irsa-temp-secret-key",
+                "SessionToken": "irsa-temp-session-token",
+                "Expiration": datetime.now(timezone.utc) + timedelta(hours=1),
+            }
+        }
+
+    def assume_role(self, **params):
+        self.assume_role_calls.append(params)
+        if tuple(params.get("Tags", ())) != self.expected_tags:
+            raise ClientError(
+                {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                "AssumeRole",
+            )
+        return {
+            "Credentials": {
+                "AccessKeyId": self.access_key,
+                "SecretAccessKey": "assumed-secret-key",
+                "SessionToken": "assumed-session-token",
+                "Expiration": datetime.now(timezone.utc) + timedelta(hours=1),
+            }
+        }
+
+
+def _irsa_env(tmp_path, irsa_role_arn: str) -> dict:
+    token_file = tmp_path / "web-identity-token"
+    token_file.write_text("test-web-identity-token")
+    return {
+        "AWS_WEB_IDENTITY_TOKEN_FILE": str(token_file),
+        "AWS_ROLE_ARN": irsa_role_arn,
+        "AWS_REGION": "us-east-1",
+    }
+
+
+def test_assume_role_sends_session_tags():
+    """The STS session carries the configured tags, so a trust policy gated on sts:TagSession admits it."""
+    sts = _TagAwareSTSClient(expected_tags=_SESSION_TAGS)
+
+    with patch("boto3.client", return_value=sts):
+        credentials, _ttl = BaseAWSLLM()._auth_with_aws_role(
+            aws_access_key_id=None,
+            aws_secret_access_key=None,
+            aws_session_token=None,
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="test-session",
+            aws_session_tags=list(_SESSION_TAGS),
+        )
+
+    assert credentials.access_key == "ASIATAGGEDSESSION"
+    assert sts.assume_role_calls == [
+        {"RoleArn": _TAGGED_ROLE_ARN, "RoleSessionName": "test-session", "Tags": _SESSION_TAGS}
+    ]
+
+
+def test_assume_role_sends_session_tags_alongside_external_id():
+    sts = _TagAwareSTSClient(expected_tags=_SESSION_TAGS)
+
+    with patch("boto3.client", return_value=sts):
+        credentials, _ttl = BaseAWSLLM()._auth_with_aws_role(
+            aws_access_key_id=None,
+            aws_secret_access_key=None,
+            aws_session_token=None,
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="test-session",
+            aws_external_id="UniqueExternalID123",
+            aws_session_tags=_SESSION_TAGS,
+        )
+
+    assert credentials.access_key == "ASIATAGGEDSESSION"
+    assert sts.assume_role_calls == [
+        {
+            "RoleArn": _TAGGED_ROLE_ARN,
+            "RoleSessionName": "test-session",
+            "ExternalId": "UniqueExternalID123",
+            "Tags": _SESSION_TAGS,
+        }
+    ]
+
+
+@pytest.mark.parametrize("aws_session_tags", [None, [], ()], ids=["none", "empty-list", "empty-tuple"])
+def test_assume_role_omits_the_tags_key_without_session_tags(aws_session_tags):
+    """Nothing configured means the AssumeRole request looks exactly as it did before tags existed."""
+    sts = _TagAwareSTSClient(expected_tags=())
+
+    with patch("boto3.client", return_value=sts):
+        credentials, _ttl = BaseAWSLLM()._auth_with_aws_role(
+            aws_access_key_id=None,
+            aws_secret_access_key=None,
+            aws_session_token=None,
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="test-session",
+            aws_session_tags=aws_session_tags,
+        )
+
+    assert credentials.access_key == "ASIATAGGEDSESSION"
+    assert sts.assume_role_calls == [{"RoleArn": _TAGGED_ROLE_ARN, "RoleSessionName": "test-session"}]
+
+
+def test_irsa_cross_account_assume_role_sends_session_tags(tmp_path):
+    irsa_role_arn = "arn:aws:iam::111111111111:role/eks-service-account-role"
+    sts = _TagAwareSTSClient(expected_tags=_SESSION_TAGS)
+
+    with patch.dict(os.environ, _irsa_env(tmp_path, irsa_role_arn)), patch("boto3.client", return_value=sts):
+        credentials, _ttl = BaseAWSLLM()._auth_with_aws_role(
+            aws_access_key_id=None,
+            aws_secret_access_key=None,
+            aws_session_token=None,
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="test-session",
+            aws_session_tags=_SESSION_TAGS,
+        )
+
+    assert credentials.access_key == "ASIATAGGEDSESSION"
+    assert sts.assume_role_calls == [
+        {"RoleArn": _TAGGED_ROLE_ARN, "RoleSessionName": "test-session", "Tags": _SESSION_TAGS}
+    ]
+
+
+def test_irsa_same_account_assume_role_sends_session_tags(tmp_path):
+    sts = _TagAwareSTSClient(expected_tags=_SESSION_TAGS)
+
+    with patch.dict(os.environ, _irsa_env(tmp_path, _TAGGED_ROLE_ARN)), patch("boto3.client", return_value=sts):
+        credentials, _ttl = BaseAWSLLM()._auth_with_aws_role(
+            aws_access_key_id=None,
+            aws_secret_access_key=None,
+            aws_session_token=None,
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="test-session",
+            aws_session_tags=_SESSION_TAGS,
+        )
+
+    assert credentials.access_key == "ASIATAGGEDSESSION"
+    assert sts.assume_role_calls == [
+        {"RoleArn": _TAGGED_ROLE_ARN, "RoleSessionName": "test-session", "Tags": _SESSION_TAGS}
+    ]
+
+
+def test_get_credentials_canonicalizes_session_tag_order_for_the_cache():
+    """Two deployments listing the same tags in a different order share one STS session."""
+    base_aws_llm = BaseAWSLLM()
+    sts = _TagAwareSTSClient(expected_tags=_SORTED_SESSION_TAGS)
+
+    with patch.dict(os.environ, _os_environ_without_aws_keys(), clear=True), patch("boto3.client", return_value=sts):
+        first = base_aws_llm.get_credentials(
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="team-session",
+            aws_session_tags=list(_SESSION_TAGS),
+        )
+        second = base_aws_llm.get_credentials(
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="team-session",
+            aws_session_tags=list(reversed(_SESSION_TAGS)),
+        )
+
+    assert first.access_key == second.access_key == "ASIATAGGEDSESSION"
+    assert sts.assume_role_calls == [
+        {"RoleArn": _TAGGED_ROLE_ARN, "RoleSessionName": "team-session", "Tags": _SORTED_SESSION_TAGS}
+    ]
+
+
+def test_get_credentials_scopes_the_cache_per_session_tag_set():
+    """Different tag sets are different principals to AWS, so each gets its own STS session."""
+    base_aws_llm = BaseAWSLLM()
+    mock_sts_client = _assume_role_sts_mock()
+    mock_sts_client.assume_role.side_effect = [
+        {
+            "Credentials": {
+                "AccessKeyId": f"assumed-access-key-{team}",
+                "SecretAccessKey": "assumed-secret-key",
+                "SessionToken": f"assumed-session-token-{team}",
+                "Expiration": datetime.now(timezone.utc) + timedelta(hours=1),
+            }
+        }
+        for team in ("genai", "platform")
+    ]
+
+    with (
+        patch.dict(os.environ, _os_environ_without_aws_keys(), clear=True),
+        patch("boto3.client", return_value=mock_sts_client),
+    ):
+        genai = base_aws_llm.get_credentials(
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="team-session",
+            aws_session_tags=[{"Key": "team", "Value": "genai"}],
+        )
+        platform = base_aws_llm.get_credentials(
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="team-session",
+            aws_session_tags=[{"Key": "team", "Value": "platform"}],
+        )
+
+    assert genai.access_key == "assumed-access-key-genai"
+    assert platform.access_key == "assumed-access-key-platform"
+    assert [call.kwargs["Tags"] for call in mock_sts_client.assume_role.call_args_list] == [
+        ({"Key": "team", "Value": "genai"},),
+        ({"Key": "team", "Value": "platform"},),
+    ]
+
+
+@pytest.mark.parametrize(
+    "aws_session_tags",
+    [
+        "team=genai",
+        {"team": "genai"},
+        [["team", "genai"]],
+        [{"key": "team", "value": "genai"}],
+        [{"Key": "team"}],
+        [{"Key": 1, "Value": "genai"}],
+    ],
+    ids=["string", "flat-dict", "pair-list", "lowercase-keys", "missing-value", "non-string-key"],
+)
+def test_get_credentials_rejects_malformed_session_tags(aws_session_tags):
+    with pytest.raises(ValueError, match="Invalid 'aws_session_tags' value"):
+        BaseAWSLLM().get_credentials(
+            aws_role_name=_TAGGED_ROLE_ARN,
+            aws_session_name="team-session",
+            aws_session_tags=aws_session_tags,
+        )
+
+
+def test_get_boto_credentials_from_optional_params_consumes_session_tags():
+    """Tags feed the STS call and must not linger in optional_params to be serialized into the body."""
+    sts = _TagAwareSTSClient(expected_tags=_SORTED_SESSION_TAGS)
+    optional_params = {
+        "aws_region_name": "us-east-1",
+        "aws_role_name": _TAGGED_ROLE_ARN,
+        "aws_session_name": "team-session",
+        "aws_session_tags": list(_SESSION_TAGS),
+    }
+
+    with patch.dict(os.environ, _os_environ_without_aws_keys(), clear=True), patch("boto3.client", return_value=sts):
+        target = BaseAWSLLM()._get_boto_credentials_from_optional_params(optional_params)
+
+    assert target.credentials.access_key == "ASIATAGGEDSESSION"
+    assert "aws_session_tags" not in optional_params
+
+
+def test_sign_request_signs_with_the_tagged_sts_session():
+    sts = _TagAwareSTSClient(expected_tags=_SORTED_SESSION_TAGS)
+    optional_params = {
+        "aws_region_name": "us-east-1",
+        "aws_role_name": _TAGGED_ROLE_ARN,
+        "aws_session_name": "team-session",
+        "aws_session_tags": list(_SESSION_TAGS),
+    }
+
+    with patch.dict(os.environ, _os_environ_without_aws_keys(), clear=True), patch("boto3.client", return_value=sts):
+        headers, _body = BaseAWSLLM()._sign_request(
+            service_name="bedrock",
+            headers={},
+            optional_params=optional_params,
+            request_data={"prompt": "hi"},
+            api_base="https://bedrock-runtime.us-east-1.amazonaws.com/model/anthropic.claude-opus-5/invoke",
+        )
+
+    assert "Credential=ASIATAGGEDSESSION/" in headers["Authorization"]
+
+
 def test_converse_handler_external_id_extraction():
     """Test that BedrockConverseLLM properly extracts and passes aws_external_id parameter"""
     from litellm.llms.bedrock.chat.converse_handler import BedrockConverseLLM
@@ -3215,3 +3505,53 @@ class TestGetRequestHeadersResign:
             extra_headers={"Authorization": "Bearer foo"},
         )
         assert prepped.headers["Authorization"] == "Bearer foo"
+
+
+@pytest.mark.asyncio
+async def test_sign_request_off_loop_if_aws_keeps_the_loop_serving_while_credentials_refresh():
+    """Regression for issue #40165: an AWS provider's signing (and the botocore credential refresh
+    inside it) must run off the event loop, so other requests keep being served meanwhile."""
+    probe = EventLoopProbe()
+
+    def sign(headers: dict[str, str]) -> dict[str, str]:
+        request = AWSRequest(
+            method="POST", url="https://bedrock-runtime.us-west-2.amazonaws.com/", data="{}", headers=headers
+        )
+        SigV4Auth(probe.credentials(), "bedrock", "us-west-2").add_auth(request)
+        return dict(request.headers)
+
+    release = asyncio.create_task(probe.release_refresh_from_the_loop())
+    signed = await sign_request_off_loop_if_aws(BaseAWSLLM(), sign, headers={"Content-Type": "application/json"})
+    await release
+
+    assert "Authorization" in signed
+    assert probe.served_during_refresh is True
+
+
+def test_run_aws_signing_leaves_the_default_executor_free_for_other_providers():
+    """A signing parked on botocore's refresh lock must not hold a default-executor thread, since every
+    other provider's async entry point hops through that same executor. The scenario runs on its own loop
+    so the one-thread default executor it pins never leaks into the session loop."""
+
+    async def scenario() -> tuple[str, str]:
+        loop = asyncio.get_running_loop()
+        loop.set_default_executor(ThreadPoolExecutor(max_workers=1))
+        signing_parked = asyncio.Event()
+        refresh_done = threading.Event()
+
+        def sign() -> str:
+            loop.call_soon_threadsafe(signing_parked.set)
+            refresh_done.wait()
+            return threading.current_thread().name
+
+        signing = asyncio.create_task(run_aws_signing(sign))
+        try:
+            await asyncio.wait_for(signing_parked.wait(), timeout=5)
+            other_provider = await asyncio.wait_for(loop.run_in_executor(None, threading.current_thread), timeout=5)
+        finally:
+            refresh_done.set()
+        return other_provider.name, await signing
+
+    other_provider, signing_thread = asyncio.run(scenario())
+    assert other_provider != signing_thread
+    assert signing_thread.startswith("aws-signing")
diff --git a/tests/test_litellm/llms/bedrock/test_bedrock_common_utils.py b/tests/test_litellm/llms/bedrock/test_bedrock_common_utils.py
index 3f03305423a..a8a21e2cd37 100644
--- a/tests/test_litellm/llms/bedrock/test_bedrock_common_utils.py
+++ b/tests/test_litellm/llms/bedrock/test_bedrock_common_utils.py
@@ -486,6 +486,7 @@ def test_merge_bedrock_aws_request_params_strips_caller_identity_when_deployment
             "aws_role_name": "arn:aws:iam::123456789012:role/caller",
             "aws_session_token": "caller-token",
             "aws_web_identity_token": "caller-web-identity",
+            "aws_session_tags": [{"Key": "team", "Value": "caller-chosen"}],
             "timeout": 600,
         },
     )
@@ -500,6 +501,7 @@ def test_merge_bedrock_aws_request_params_strips_caller_identity_when_deployment
         "aws_role_name",
         "aws_session_token",
         "aws_web_identity_token",
+        "aws_session_tags",
     ):
         assert stripped not in merged
 
@@ -616,6 +618,60 @@ def test_sign_aws_request_assumes_role_with_external_id(monkeypatch):
     assert signed_data == b'{"jobName": "litellm-batch-job"}'
 
 
+def test_sign_aws_request_assumes_role_with_session_tags(monkeypatch):
+    """Batch and file signing must carry the deployment's session tags into the AssumeRole call too."""
+    import datetime
+    from unittest.mock import patch
+
+    import boto3
+    from botocore.exceptions import ClientError
+
+    from litellm.llms.bedrock.common_utils import CommonBatchFilesUtils
+
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+
+    class FakeSTSClient:
+        def get_caller_identity(self):
+            return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+        def assume_role(self, **params):
+            if list(params.get("Tags", ())) != tags:
+                raise ClientError(
+                    {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                    "AssumeRole",
+                )
+            return {
+                "Credentials": {
+                    "AccessKeyId": "ASIABATCHSIGNTAGGED",
+                    "SecretAccessKey": "assumed-secret",
+                    "SessionToken": "assumed-session-token",
+                    "Expiration": datetime.datetime.now(datetime.timezone.utc) + datetime.timedelta(minutes=30),
+                }
+            }
+
+    optional_params = {
+        "aws_region_name": "us-east-1",
+        "aws_access_key_id": "AKIABATCHSIGNCALLER",
+        "aws_secret_access_key": "pod-caller-secret",
+        "aws_role_name": "arn:aws:iam::999999999999:role/litellm-batch-sign-role",
+        "aws_session_name": "litellm-batch-sign-session",
+        "aws_session_tags": tags,
+    }
+
+    with patch.object(boto3, "client", return_value=FakeSTSClient()):
+        signed_headers, _signed_data = CommonBatchFilesUtils().sign_aws_request(
+            service_name="bedrock",
+            data={"jobName": "litellm-batch-job"},
+            endpoint_url="https://bedrock.us-east-1.amazonaws.com/model-invocation-job",
+            optional_params=optional_params,
+        )
+
+    authorization = {key.lower(): value for key, value in signed_headers.items()}["authorization"]
+    assert "Credential=ASIABATCHSIGNTAGGED/" in authorization
+
+
 # --------------------------------------------------------------------------- #
 # Provider error headers (LIT-5428)                                            #
 # --------------------------------------------------------------------------- #
diff --git a/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_transformation.py b/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_transformation.py
index 1be94d4daa2..e83a844c87e 100644
--- a/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_transformation.py
+++ b/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_transformation.py
@@ -6,15 +6,20 @@ API docs: https://docs.aws.amazon.com/bedrock/latest/userguide/bedrock-mantle.ht
 """
 
 import json
+import asyncio
 from unittest.mock import patch
 
 
 import httpx
 import pytest
+from botocore.auth import SigV4Auth
+from botocore.awsrequest import AWSRequest
 
 import litellm
 from litellm.llms.bedrock_mantle.chat.transformation import BedrockMantleChatConfig
+from litellm.llms.bedrock.base_aws_llm import sign_request_off_loop_if_aws
 from litellm.types.utils import LlmProviders
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 
 @pytest.fixture
@@ -710,3 +715,26 @@ def test_gemma_4_models_register_under_bedrock_mantle(local_cost_map, model_id):
     resolved_model, provider, _, _ = litellm.get_llm_provider(full_model_name)
     assert provider == "bedrock_mantle"
     assert resolved_model == model_id
+
+
+@pytest.mark.asyncio
+async def test_mantle_signing_runs_off_the_event_loop():
+    """Regression for issue #40165: Mantle signs with SigV4 through a composed BaseAWSLLM, so the
+    off-loop gate must recognise it too, or its credential refresh blocks the loop like Bedrock's did."""
+    probe = EventLoopProbe()
+
+    def sign(headers: dict[str, str]) -> dict[str, str]:
+        request = AWSRequest(
+            method="POST", url="https://bedrock-mantle.us-east-1.api.aws/v1/responses", data="{}", headers=headers
+        )
+        SigV4Auth(probe.credentials(), "bedrock", "us-east-1").add_auth(request)
+        return dict(request.headers)
+
+    release = asyncio.create_task(probe.release_refresh_from_the_loop())
+    signed = await sign_request_off_loop_if_aws(
+        BedrockMantleChatConfig(), sign, headers={"Content-Type": "application/json"}
+    )
+    await release
+
+    assert "Authorization" in signed
+    assert probe.served_during_refresh is True
diff --git a/tests/test_litellm/llms/chatgpt/responses/test_chatgpt_responses_transformation.py b/tests/test_litellm/llms/chatgpt/responses/test_chatgpt_responses_transformation.py
index 8e0415d50de..a7520bd5955 100644
--- a/tests/test_litellm/llms/chatgpt/responses/test_chatgpt_responses_transformation.py
+++ b/tests/test_litellm/llms/chatgpt/responses/test_chatgpt_responses_transformation.py
@@ -10,18 +10,23 @@ from unittest.mock import MagicMock, patch
 import httpx
 import pytest
 
-
+import litellm
+from litellm.llms.chatgpt.responses.transformation import ChatGPTResponsesAPIConfig
 from litellm.llms.openai.common_utils import OpenAIError
+from litellm.main import responses_api_bridge_check
 from litellm.types.router import GenericLiteLLMParams
 from litellm.types.utils import LlmProviders
 from litellm.utils import ProviderConfigManager
-from litellm.llms.chatgpt.responses.transformation import ChatGPTResponsesAPIConfig
 
 
 class TestChatGPTResponsesAPITransformation:
     @pytest.mark.parametrize(
         "model_name",
         [
+            "chatgpt/gpt-5.5",
+            "chatgpt/gpt-5.6-luna",
+            "chatgpt/gpt-5.6-sol",
+            "chatgpt/gpt-5.6-terra",
             "chatgpt/gpt-5.4",
             "chatgpt/gpt-5.4-pro",
             "chatgpt/gpt-5.3-chat-latest",
@@ -40,6 +45,52 @@ class TestChatGPTResponsesAPITransformation:
         assert isinstance(config, ChatGPTResponsesAPIConfig)
         assert config.custom_llm_provider == LlmProviders.CHATGPT
 
+    @pytest.mark.parametrize(
+        "model_name",
+        [
+            "chatgpt/gpt-5.5",
+            "chatgpt/gpt-5.6-luna",
+            "chatgpt/gpt-5.6-sol",
+            "chatgpt/gpt-5.6-terra",
+        ],
+    )
+    def test_chatgpt_responses_model_metadata(self, model_name: str, local_model_cost_map: None) -> None:
+        model_info = litellm.get_model_info(model_name)
+
+        assert model_info["litellm_provider"] == "chatgpt"
+        assert model_info["mode"] == "responses"
+        assert model_info["supported_endpoints"] == [
+            "/v1/chat/completions",
+            "/v1/responses",
+        ]
+        assert model_info["max_input_tokens"] == 1050000
+        assert model_info["max_output_tokens"] == 128000
+
+    @pytest.mark.parametrize(
+        "model_name",
+        [
+            "gpt-5.5",
+            "gpt-5.6-luna",
+            "gpt-5.6-sol",
+            "gpt-5.6-terra",
+        ],
+    )
+    def test_chatgpt_models_bridge_chat_completions_to_responses(
+        self, model_name: str, local_model_cost_map: None
+    ) -> None:
+        """A chat completions request for these models must take the Responses bridge.
+
+        `gpt-5.6-*` also exists as an openai chat model, so an unregistered
+        chatgpt model resolves to mode "chat" here and never reaches the bridge.
+        """
+        model_info, resolved_model = responses_api_bridge_check(
+            model=model_name,
+            custom_llm_provider="chatgpt",
+        )
+
+        assert model_info["mode"] == "responses"
+        assert resolved_model == model_name
+
     @patch("litellm.llms.chatgpt.responses.transformation.Authenticator")
     def test_chatgpt_responses_endpoint_url(self, mock_authenticator_class):
         mock_auth_instance = MagicMock()
diff --git a/tests/test_litellm/llms/custom_httpx/test_http_handler.py b/tests/test_litellm/llms/custom_httpx/test_http_handler.py
index 9e64bfafa54..f8868cfaf83 100644
--- a/tests/test_litellm/llms/custom_httpx/test_http_handler.py
+++ b/tests/test_litellm/llms/custom_httpx/test_http_handler.py
@@ -1547,3 +1547,131 @@ def test_sync_force_ipv4_https_proxy_mount_uses_handler_ca_bundle(
         handler.close()
 
     assert response.text == "ok-tls"
+
+
+@pytest.mark.asyncio
+async def test_put_can_refuse_to_follow_a_redirect():
+    """The client follows redirects by default; a caller uploading to a URL it did not choose must be able to opt out."""
+    hops: list[str] = []  # mutable-ok: the fake transport records the paths it was asked for
+
+    async def mock_handler(request: httpx.Request) -> httpx.Response:
+        hops.append(request.url.path)
+        if request.url.path == "/first":
+            return httpx.Response(302, request=request, headers={"location": "/second"})
+        return httpx.Response(200, request=request)
+
+    handler = AsyncHTTPHandler()
+    await handler.client.aclose()
+    handler.client = httpx.AsyncClient(transport=httpx.MockTransport(mock_handler), follow_redirects=True)
+    try:
+        followed = await handler.put("https://uploads.example/first", data=b"x")
+        assert followed.status_code == 200
+        assert hops == ["/first", "/second"]
+
+        hops.clear()
+        with pytest.raises(MaskedHTTPStatusError) as refused:
+            await handler.put("https://uploads.example/first", data=b"x", follow_redirects=False)
+        assert refused.value.status_code == 302
+        assert hops == ["/first"]
+    finally:
+        await handler.close()
+
+
+@pytest.mark.asyncio
+async def test_a_retried_put_stays_a_put_and_still_refuses_redirects():
+    """
+    The connection-error retry used to resend as POST through a client that follows redirects.
+
+    Storage answers a POST to a presigned PUT url with 403 or 405, so the batch looked
+    permanently rejected, and the redirect refusal the caller asked for was silently lost.
+    """
+    attempts: list[tuple[str, str]] = []  # mutable-ok: the fake transports record what they were asked for
+
+    async def refusing_transport(request: httpx.Request) -> httpx.Response:
+        attempts.append((request.method, request.url.path))
+        raise httpx.ConnectError("connection reset", request=request)
+
+    async def retry_transport(request: httpx.Request) -> httpx.Response:
+        attempts.append((request.method, request.url.path))
+        if request.url.path == "/first":
+            return httpx.Response(302, request=request, headers={"location": "/second"})
+        return httpx.Response(200, request=request)
+
+    class HandlerWithFakeRetryClient(AsyncHTTPHandler):
+        def create_client(self, *args, **kwargs) -> httpx.AsyncClient:
+            return httpx.AsyncClient(transport=httpx.MockTransport(retry_transport), follow_redirects=True)
+
+    handler = HandlerWithFakeRetryClient()
+    await handler.client.aclose()
+    handler.client = httpx.AsyncClient(transport=httpx.MockTransport(refusing_transport))
+    try:
+        with pytest.raises(MaskedHTTPStatusError) as refused:
+            await handler.put("https://uploads.example/first", data=b"x", follow_redirects=False)
+
+        assert refused.value.status_code == 302
+        assert attempts == [("PUT", "/first"), ("PUT", "/first")]
+    finally:
+        await handler.client.aclose()
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("target", ["https://example.com/final.json?next=1", "https://other.example/final.json?next=1"])
+async def test_bounded_get_preserves_sdk_redirect_auth_and_query_handling(respx_mock, monkeypatch, target):
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    respx_mock.get("https://example.com/spec.json?original=1").respond(302, headers={"location": target})
+    destination = respx_mock.get(target).respond(200, json={"paths": {}})
+    handler = AsyncHTTPHandler()
+    try:
+        response = await handler.get(
+            "https://example.com/spec.json?original=1", max_response_bytes=100, follow_redirects=True,
+            headers={"Authorization": "Bearer sentinel", "Accept-Encoding": "gzip"}, timeout=2.0,
+        )
+    finally:
+        await handler.close()
+    assert response.json() == {"paths": {}}
+    request = destination.calls[0].request
+    assert request.headers.get("authorization") == (None if "other.example" in target else "Bearer sentinel")
+    assert request.headers["accept-encoding"] == "identity"
+    assert str(request.url) == target
+    assert request.extensions["timeout"]["read"] == 2.0
+
+
+@pytest.mark.asyncio
+async def test_bounded_get_stops_redirect_loops(respx_mock, monkeypatch):
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    route = respx_mock.get("https://example.com/spec.json").respond(302, headers={"location": "/spec.json"})
+    handler = AsyncHTTPHandler()
+    try:
+        with pytest.raises(ValueError, match="Too many redirects"):
+            await handler.get("https://example.com/spec.json", max_response_bytes=100, follow_redirects=True)
+    finally:
+        await handler.close()
+    assert route.call_count == 11
+
+
+@pytest.mark.asyncio
+async def test_bounded_get_closes_stream_on_cancellation(respx_mock, monkeypatch):
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    started = asyncio.Event()
+    closed = asyncio.Event()
+
+    class SlowStream(httpx.AsyncByteStream):
+        async def __aiter__(self):
+            yield b"x"
+            started.set()
+            await asyncio.Event().wait()
+
+        async def aclose(self):
+            closed.set()
+
+    respx_mock.get("https://example.com/slow.json").respond(200, stream=SlowStream())
+    handler = AsyncHTTPHandler()
+    try:
+        task = asyncio.create_task(handler.get("https://example.com/slow.json", max_response_bytes=100))
+        await asyncio.wait_for(started.wait(), timeout=1)
+        task.cancel()
+        with pytest.raises(asyncio.CancelledError):
+            await task
+    finally:
+        await handler.close()
+    assert closed.is_set()
diff --git a/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py b/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py
index 98a5f4b2db5..cea2d439198 100644
--- a/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py
+++ b/tests/test_litellm/llms/custom_httpx/test_llm_http_handler.py
@@ -7,6 +7,7 @@ from unittest.mock import AsyncMock, Mock, patch
 
 import httpx
 import pytest
+from botocore.credentials import RefreshableCredentials
 
 import litellm
 from litellm._logging import verbose_logger
@@ -19,6 +20,7 @@ from litellm.llms.base_llm.audio_transcription.transformation import (
     BaseAudioTranscriptionConfig,
 )
 from litellm.llms.base_llm.chat.transformation import BaseConfig, BaseLLMException
+from litellm.llms.bedrock.base_aws_llm import SignsRequestsWithAWS
 from litellm.llms.base_llm.image_edit.transformation import BaseImageEditConfig
 from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
 from litellm.llms.custom_httpx.llm_http_handler import (
@@ -29,11 +31,15 @@ from litellm.llms.custom_httpx.llm_http_handler import (
     _rust_responses_websocket_enabled,
 )
 from litellm.llms.azure.videos.transformation import AzureVideoConfig
+from litellm.llms.bedrock.messages.invoke_transformations.anthropic_claude3_transformation import (
+    AmazonAnthropicClaudeMessagesConfig,
+)
 from litellm.llms.mistral.ocr.transformation import MistralOCRConfig
 from litellm.llms.openai.videos.transformation import OpenAIVideoConfig
 from litellm.types.llms.openai import ResponsesAPIResponse
 from litellm.types.router import GenericLiteLLMParams
 from litellm.types.utils import ImageObject, ImageResponse, ModelResponse, TranscriptionResponse
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 _ACTIVE_KEY = "_code_interpreter_interception_active"
 _SANDBOX_KEY = "_code_interpreter_interception_sandbox_key"
@@ -813,6 +819,65 @@ async def test_anthropic_messages_streaming_response_aclose_closes_agentic_upstr
     assert tracker.closed is True
 
 
+class _ProbedBedrockMessagesConfig(AmazonAnthropicClaudeMessagesConfig):
+    def __init__(self, probe: EventLoopProbe) -> None:
+        super().__init__()
+        self._probe = probe
+
+    def get_credentials(
+        self,
+        **kwargs: object,  # kwargs-ok: mirrors the base resolver's keyword contract, which the probe ignores
+    ) -> RefreshableCredentials:
+        return self._probe.credentials()
+
+
+@pytest.mark.asyncio
+async def test_async_anthropic_messages_handler_signs_bedrock_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: /v1/messages on Bedrock signed on the loop, so botocore's blocking
+    credential refresh inside SigV4 stalled every other request on the worker."""
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    probe = EventLoopProbe()
+    handler = BaseLLMHTTPHandler()
+    upstream_response = httpx.Response(
+        200,
+        json={
+            "id": "msg_123",
+            "type": "message",
+            "role": "assistant",
+            "content": [{"type": "text", "text": "hi"}],
+            "model": "claude-haiku-4-5-20251001",
+            "stop_reason": "end_turn",
+            "stop_sequence": None,
+            "usage": {"input_tokens": 1, "output_tokens": 1},
+        },
+        request=httpx.Request("POST", "https://bedrock-runtime.us-west-2.amazonaws.com/"),
+    )
+    mock_client = AsyncMock(spec=AsyncHTTPHandler)
+    mock_client.post = AsyncMock(return_value=upstream_response)
+    mock_logging_obj = Mock()
+    mock_logging_obj.model_call_details = {}
+    mock_logging_obj.dynamic_success_callbacks = None
+    release = asyncio.create_task(probe.release_refresh_from_the_loop())
+
+    await handler.async_anthropic_messages_handler(
+        model="us.anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        anthropic_messages_provider_config=_ProbedBedrockMessagesConfig(probe),
+        anthropic_messages_optional_request_params={"max_tokens": 16},
+        custom_llm_provider="bedrock",
+        litellm_params=GenericLiteLLMParams(aws_region_name="us-west-2"),
+        logging_obj=mock_logging_obj,
+        client=mock_client,
+        stream=False,
+        kwargs={},
+    )
+    await release
+
+    sent_headers = mock_client.post.call_args.kwargs["headers"]
+    assert sent_headers["Authorization"].startswith("AWS4-HMAC-SHA256")
+    assert probe.served_during_refresh is True
+
+
 @pytest.mark.asyncio
 async def test_async_anthropic_messages_handler_passes_litellm_metadata():
     """Ensure litellm_metadata from kwargs is forwarded via update_from_kwargs.
@@ -3367,6 +3432,26 @@ async def test_completion_signs_and_logs_off_the_event_loop_after_the_async_tran
     assert captured["body"] == {"transformed_by": "async"}
     assert config.sign_threads and all(thread is not loop_thread for thread in config.sign_threads)
     assert pre_call_threads and all(thread is not loop_thread for thread in pre_call_threads)
+    assert not any(thread.name.startswith("aws-signing") for thread in config.sign_threads + pre_call_threads)
+
+
+class _AWSTransformRecordingConfig(SignsRequestsWithAWS, _TransformRecordingConfig):
+    pass
+
+
+async def test_completion_signs_aws_configs_on_the_aws_signing_pool_after_the_async_transform():
+    config = _AWSTransformRecordingConfig(transform_async=True)
+    pre_call_threads = []
+    logging_obj = Mock(dynamic_success_callbacks=None, model_call_details={})
+    logging_obj.pre_call.side_effect = lambda **kwargs: pre_call_threads.append(threading.current_thread())
+
+    pending, captured = _start_async_completion(config, logging_obj)
+    response = await pending
+
+    assert response.choices[0].message.content == "async"
+    assert captured["body"] == {"transformed_by": "async"}
+    assert config.sign_threads and all(thread.name.startswith("aws-signing") for thread in config.sign_threads)
+    assert pre_call_threads and all(thread.name.startswith("aws-signing") for thread in pre_call_threads)
 
 
 async def test_completion_keeps_sync_transform_request_before_returning_by_default():
diff --git a/tests/test_litellm/llms/dashscope/test_dashscope_rerank_transformation.py b/tests/test_litellm/llms/dashscope/test_dashscope_rerank_transformation.py
index 936de812bc6..4466e5b8767 100644
--- a/tests/test_litellm/llms/dashscope/test_dashscope_rerank_transformation.py
+++ b/tests/test_litellm/llms/dashscope/test_dashscope_rerank_transformation.py
@@ -25,19 +25,43 @@ class TestDashScopeRerankURL:
         url = self.config.get_complete_url(api_base=None, model="qwen3-rerank")
         assert url == DEFAULT_RERANK_URL
 
-    def test_explicit_v1_base_appends_reranks(self):
+    def test_chat_shaped_base_remaps_to_rerank_route(self):
         url = self.config.get_complete_url(
             api_base="https://dashscope.aliyuncs.com/compatible-mode/v1",
             model="qwen3-rerank",
         )
-        assert url == "https://dashscope.aliyuncs.com/compatible-mode/v1/reranks"
+        assert url == "https://dashscope.aliyuncs.com/compatible-api/v1/reranks"
 
-    def test_intl_v1_base_appends_reranks(self):
+    def test_intl_chat_shaped_base_remaps_to_intl_rerank_route(self):
         url = self.config.get_complete_url(
             api_base="https://dashscope-intl.aliyuncs.com/compatible-mode/v1",
             model="qwen3-rerank",
         )
-        assert url == "https://dashscope-intl.aliyuncs.com/compatible-mode/v1/reranks"
+        assert url == "https://dashscope-intl.aliyuncs.com/compatible-api/v1/reranks"
+
+    def test_chat_shaped_base_with_trailing_slash_remaps(self):
+        url = self.config.get_complete_url(
+            api_base="https://dashscope-intl.aliyuncs.com/compatible-mode/v1/",
+            model="qwen3-rerank",
+        )
+        assert url == "https://dashscope-intl.aliyuncs.com/compatible-api/v1/reranks"
+
+    def test_rerank_env_var_wins_over_chat_shaped_base(self, monkeypatch):
+        monkeypatch.setenv(
+            "DASHSCOPE_API_BASE_RERANK", "https://rerank.example.com/v1/reranks"
+        )
+        url = self.config.get_complete_url(
+            api_base="https://dashscope-intl.aliyuncs.com/compatible-mode/v1",
+            model="qwen3-rerank",
+        )
+        assert url == "https://rerank.example.com/v1/reranks"
+
+    def test_non_aliyun_chat_path_base_not_remapped(self):
+        url = self.config.get_complete_url(
+            api_base="https://gateway.example.com/compatible-mode/v1",
+            model="qwen3-rerank",
+        )
+        assert url == "https://gateway.example.com/compatible-mode/v1/reranks"
 
     def test_already_complete_url_passthrough(self):
         full = "https://dashscope.aliyuncs.com/compatible-api/v1/reranks"
diff --git a/tests/test_litellm/llms/dashscope/test_qwen_brand_aliases.py b/tests/test_litellm/llms/dashscope/test_qwen_brand_aliases.py
index 064d9d58f0c..7862297bcd5 100644
--- a/tests/test_litellm/llms/dashscope/test_qwen_brand_aliases.py
+++ b/tests/test_litellm/llms/dashscope/test_qwen_brand_aliases.py
@@ -209,6 +209,11 @@ class TestQwenBrandDefaultUrls:
         url = brand["rerank_config"]().get_complete_url(api_base=None, model="gte-rerank-v2")
         assert url == "https://rerank.example.com/v1/reranks"
 
+    @pytest.mark.parametrize("brand", BRAND_CASES)
+    def test_rerank_remaps_chat_shaped_default_base(self, brand):
+        url = brand["rerank_config"]().get_complete_url(api_base=brand["default_base"], model="gte-rerank-v2")
+        assert url == brand["default_rerank_base"]
+
     @pytest.mark.parametrize("brand", BRAND_CASES)
     def test_image_generation_complete_url(self, brand):
         url = brand["image_config"]().get_complete_url(
diff --git a/tests/test_litellm/llms/databricks/chat/test_databricks_chat_transformation.py b/tests/test_litellm/llms/databricks/chat/test_databricks_chat_transformation.py
index 02655fb7f77..caf7bed7385 100644
--- a/tests/test_litellm/llms/databricks/chat/test_databricks_chat_transformation.py
+++ b/tests/test_litellm/llms/databricks/chat/test_databricks_chat_transformation.py
@@ -255,6 +255,19 @@ def test_transform_messages_sanitizes_empty_content():
     assert result[1]["content"] == "Hi"
 
 
+def test_transform_request_preserves_unity_model_service_name():
+    config = DatabricksConfig()
+    result = config.transform_request(
+        model="system.ai.kimi-k3",
+        messages=[{"role": "user", "content": "hello"}],
+        optional_params={},
+        litellm_params={},
+        headers={},
+    )
+
+    assert result["model"] == "system.ai.kimi-k3"
+
+
 def test_transform_request_strips_thinking_blocks_and_reasoning_content():
     """Regression for LIT-6762: replaying an assistant turn that litellm decorated with
     `thinking_blocks` / `reasoning_content` made Databricks 400 with
@@ -590,3 +603,87 @@ def test_chunk_parser_without_usage_still_parses_content():
     assert result.id == "chatcmpl-test"
     assert result.model == "databricks-claude-sonnet-5"
     assert result.choices[0]["delta"]["content"] == "hi"
+
+
+@pytest.mark.parametrize("reasoning_key", ["reasoning_content", "reasoning"])
+def test_transform_choices_surfaces_top_level_reasoning_content(reasoning_key: str) -> None:
+    config = DatabricksConfig()
+    databricks_choices = [
+        {
+            "message": {
+                "role": "assistant",
+                "content": "391",
+                reasoning_key: "We need answer just number. 17*23=391.",
+            },
+            "index": 0,
+            "finish_reason": "stop",
+        }
+    ]
+
+    choices = config._transform_dbrx_choices(choices=databricks_choices)
+
+    assert choices[0].message.content == "391"
+    assert choices[0].message.reasoning_content == "We need answer just number. 17*23=391."
+    assert getattr(choices[0].message, "thinking_blocks", None) is None
+
+
+def test_transform_choices_parses_think_tags_in_string_content():
+    config = DatabricksConfig()
+    databricks_choices = [
+        {
+            "message": {"role": "assistant", "content": "<think>17 times 23</think>391"},
+            "index": 0,
+            "finish_reason": "stop",
+        }
+    ]
+
+    choices = config._transform_dbrx_choices(choices=databricks_choices)
+
+    assert choices[0].message.content == "391"
+    assert choices[0].message.reasoning_content == "17 times 23"
+
+
+def test_transform_choices_prefers_reasoning_blocks_over_top_level_field():
+    config = DatabricksConfig()
+    databricks_choices = [
+        {
+            "message": {
+                "role": "assistant",
+                "content": [
+                    {"type": "reasoning", "summary": [{"type": "summary_text", "text": "from block"}]},
+                    {"type": "text", "text": "391"},
+                ],
+                "reasoning_content": "from field",
+            },
+            "index": 0,
+            "finish_reason": "stop",
+        }
+    ]
+
+    choices = config._transform_dbrx_choices(choices=databricks_choices)
+
+    assert choices[0].message.reasoning_content == "from block"
+    assert choices[0].message.content == "391"
+
+
+@pytest.mark.parametrize("reasoning_key", ["reasoning_content", "reasoning"])
+def test_chunk_parser_surfaces_top_level_reasoning_delta(reasoning_key: str) -> None:
+    iterator = DatabricksChatResponseIterator(None, sync_stream=True)
+    chunk = {
+        "id": "1",
+        "object": "chat.completion.chunk",
+        "created": 0,
+        "model": "lit-qa-deepseek-v4-flash",
+        "choices": [
+            {
+                "delta": {"role": "assistant", "content": None, reasoning_key: "We need answer"},
+                "index": 0,
+                "finish_reason": None,
+            }
+        ],
+    }
+
+    parsed = iterator.chunk_parser(chunk)
+
+    assert parsed.choices[0].delta.reasoning_content == "We need answer"
+    assert parsed.choices[0].delta.content is None
diff --git a/tests/test_litellm/llms/databricks/test_databricks_partner_integration.py b/tests/test_litellm/llms/databricks/test_databricks_partner_integration.py
index 39198bb20f3..c6ad78366f7 100644
--- a/tests/test_litellm/llms/databricks/test_databricks_partner_integration.py
+++ b/tests/test_litellm/llms/databricks/test_databricks_partner_integration.py
@@ -657,6 +657,77 @@ class TestEndpointURLConstruction:
 
         assert api_base.endswith("/chat/completions")
 
+    def test_chat_gateway_endpoint_for_unity_model_on_legacy_base(self, monkeypatch):
+        from litellm.llms.databricks.chat.transformation import DatabricksConfig
+
+        monkeypatch.delenv("DATABRICKS_CLIENT_ID", raising=False)
+        monkeypatch.delenv("DATABRICKS_CLIENT_SECRET", raising=False)
+
+        url = DatabricksConfig().get_complete_url(
+            api_base="https://test.net/serving-endpoints",
+            api_key="test-key",
+            model="system.ai.kimi-k3",
+            optional_params={},
+            litellm_params={},
+        )
+
+        assert url == "https://test.net/ai-gateway/mlflow/v1/chat/completions"
+
+    def test_chat_gateway_endpoint_preserves_explicit_gateway_base(self, monkeypatch):
+        from litellm.llms.databricks.chat.transformation import DatabricksConfig
+
+        monkeypatch.delenv("DATABRICKS_CLIENT_ID", raising=False)
+        monkeypatch.delenv("DATABRICKS_CLIENT_SECRET", raising=False)
+
+        url = DatabricksConfig().get_complete_url(
+            api_base="https://test.net/ai-gateway/mlflow/v1/",
+            api_key="test-key",
+            model="system.ai.kimi-k3",
+            optional_params={},
+            litellm_params={},
+        )
+
+        assert url == "https://test.net/ai-gateway/mlflow/v1/chat/completions"
+
+    def test_chat_gateway_preserves_unity_model_service_name_with_explicit_base(self, monkeypatch):
+        from litellm.llms.databricks.chat.transformation import DatabricksConfig
+
+        monkeypatch.delenv("DATABRICKS_CLIENT_ID", raising=False)
+        monkeypatch.delenv("DATABRICKS_CLIENT_SECRET", raising=False)
+        config = DatabricksConfig()
+        request = config.transform_request(
+            model="catalog.schema.kimi-k3",
+            messages=[{"role": "user", "content": "hello"}],
+            optional_params={},
+            litellm_params={},
+            headers={},
+        )
+
+        assert config.get_complete_url(
+            api_base="https://test.net/ai-gateway/mlflow/v1",
+            api_key="test-key",
+            model="catalog.schema.kimi-k3",
+            optional_params={},
+            litellm_params={},
+        ) == "https://test.net/ai-gateway/mlflow/v1/chat/completions"
+        assert request["model"] == "catalog.schema.kimi-k3"
+
+    def test_chat_legacy_endpoint_remains_default(self, monkeypatch):
+        from litellm.llms.databricks.chat.transformation import DatabricksConfig
+
+        monkeypatch.delenv("DATABRICKS_CLIENT_ID", raising=False)
+        monkeypatch.delenv("DATABRICKS_CLIENT_SECRET", raising=False)
+
+        url = DatabricksConfig().get_complete_url(
+            api_base="https://test.net/serving-endpoints",
+            api_key="test-key",
+            model="databricks-kimi-k3",
+            optional_params={},
+            litellm_params={},
+        )
+
+        assert url == "https://test.net/serving-endpoints/chat/completions"
+
     def test_embeddings_endpoint(self, monkeypatch):
         """Embeddings endpoint is correctly appended."""
         monkeypatch.delenv("DATABRICKS_CLIENT_ID", raising=False)
diff --git a/tests/test_litellm/llms/hosted_vllm/image_edit/test_hosted_vllm_image_edit_transformation.py b/tests/test_litellm/llms/hosted_vllm/image_edit/test_hosted_vllm_image_edit_transformation.py
new file mode 100644
index 00000000000..bc0ea23e249
--- /dev/null
+++ b/tests/test_litellm/llms/hosted_vllm/image_edit/test_hosted_vllm_image_edit_transformation.py
@@ -0,0 +1,155 @@
+import httpx
+import pytest
+
+import litellm
+from litellm.llms.custom_httpx.http_handler import HTTPHandler
+from litellm.llms.hosted_vllm.image_edit import get_hosted_vllm_image_edit_config
+from litellm.llms.hosted_vllm.image_edit.transformation import HostedVLLMImageEditConfig
+from litellm.types.utils import LlmProviders
+from litellm.utils import ProviderConfigManager
+
+PNG_BYTES = b"\x89PNG\r\n\x1a\nfakepng"
+MODEL = "Qwen/Qwen-Image-Edit-2511"
+
+
+@pytest.fixture(autouse=True)
+def _clear_hosted_vllm_env(monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.delenv("HOSTED_VLLM_API_KEY", raising=False)
+    monkeypatch.delenv("HOSTED_VLLM_API_BASE", raising=False)
+
+
+def test_provider_config_registration():
+    config = ProviderConfigManager.get_provider_image_edit_config(
+        model=f"hosted_vllm/{MODEL}",
+        provider=LlmProviders.HOSTED_VLLM,
+    )
+
+    assert isinstance(config, HostedVLLMImageEditConfig)
+    assert isinstance(get_hosted_vllm_image_edit_config(MODEL), HostedVLLMImageEditConfig)
+
+
+@pytest.mark.parametrize(
+    "api_base",
+    ["http://localhost:8091", "http://localhost:8091/", "http://localhost:8091/v1", "http://localhost:8091/v1/"],
+)
+def test_get_complete_url_appends_images_edits(api_base: str):
+    config = HostedVLLMImageEditConfig()
+
+    assert (
+        config.get_complete_url(model=MODEL, api_base=api_base, litellm_params={})
+        == "http://localhost:8091/v1/images/edits"
+    )
+
+
+def test_get_complete_url_falls_back_to_env(monkeypatch: pytest.MonkeyPatch):
+    monkeypatch.setenv("HOSTED_VLLM_API_BASE", "http://vllm-omni:8000/v1")
+    config = HostedVLLMImageEditConfig()
+
+    assert (
+        config.get_complete_url(model=MODEL, api_base=None, litellm_params={})
+        == "http://vllm-omni:8000/v1/images/edits"
+    )
+
+
+def test_get_complete_url_requires_api_base():
+    config = HostedVLLMImageEditConfig()
+
+    with pytest.raises(ValueError, match="api_base not set"):
+        config.get_complete_url(model=MODEL, api_base=None, litellm_params={})
+
+
+def test_validate_environment_defaults_to_fake_api_key():
+    headers = HostedVLLMImageEditConfig().validate_environment(headers={}, model=MODEL)
+
+    assert headers == {"Authorization": "Bearer fake-api-key"}
+
+
+def test_validate_environment_uses_provided_api_key_and_keeps_headers():
+    headers = HostedVLLMImageEditConfig().validate_environment(
+        headers={"X-Test": "1"},
+        model=MODEL,
+        api_key="my-custom-key",
+    )
+
+    assert headers == {"X-Test": "1", "Authorization": "Bearer my-custom-key"}
+
+
+def test_validate_environment_falls_back_to_env_api_key(monkeypatch: pytest.MonkeyPatch):
+    monkeypatch.setenv("HOSTED_VLLM_API_KEY", "env-key")
+
+    headers = HostedVLLMImageEditConfig().validate_environment(headers={}, model=MODEL)
+
+    assert headers["Authorization"] == "Bearer env-key"
+
+
+def test_image_edit_posts_multipart_to_vllm_omni():
+    captured: list[httpx.Request] = []
+
+    def handler(request: httpx.Request) -> httpx.Response:
+        captured.append(request)
+        return httpx.Response(200, json={"created": 1712697600, "data": [{"b64_json": "aW1n"}]})
+
+    response = litellm.image_edit(
+        model=f"hosted_vllm/{MODEL}",
+        image=PNG_BYTES,
+        prompt="add a hat",
+        api_base="http://localhost:8091",
+        api_key="test-key",
+        client=HTTPHandler(client=httpx.Client(transport=httpx.MockTransport(handler))),
+        seed=42,
+    )
+
+    assert response.data
+    assert len(captured) == 1
+    request = captured[0]
+    assert str(request.url) == "http://localhost:8091/v1/images/edits"
+    assert request.headers["authorization"] == "Bearer test-key"
+    assert request.headers["content-type"].startswith("multipart/form-data")
+    assert b'name="image[]"' in request.content
+    assert PNG_BYTES in request.content
+    assert f'name="model"\r\n\r\n{MODEL}'.encode() in request.content
+    assert b'name="prompt"\r\n\r\nadd a hat' in request.content
+    assert b'name="seed"\r\n\r\n42' in request.content
+
+
+@pytest.mark.parametrize("param", ["mask", "quality", "input_fidelity"])
+def test_params_vllm_omni_ignores_are_not_advertised(param: str):
+    supported = HostedVLLMImageEditConfig().get_supported_openai_params(MODEL)
+
+    assert param not in supported
+    assert {"image", "prompt", "n", "size", "response_format", "background", "user"} <= set(supported)
+
+
+def test_image_edit_rejects_quality_unless_dropped():
+    captured: list[httpx.Request] = []
+
+    def handler(request: httpx.Request) -> httpx.Response:
+        captured.append(request)
+        return httpx.Response(200, json={"created": 1712697600, "data": [{"b64_json": "aW1n"}]})
+
+    client = HTTPHandler(client=httpx.Client(transport=httpx.MockTransport(handler)))
+
+    with pytest.raises(litellm.UnsupportedParamsError, match="quality"):
+        litellm.image_edit(
+            model=f"hosted_vllm/{MODEL}",
+            image=PNG_BYTES,
+            prompt="add a hat",
+            api_base="http://localhost:8091",
+            client=client,
+            quality="low",
+        )
+    assert captured == []
+
+    litellm.image_edit(
+        model=f"hosted_vllm/{MODEL}",
+        image=PNG_BYTES,
+        prompt="add a hat",
+        api_base="http://localhost:8091",
+        client=client,
+        quality="low",
+        drop_params=True,
+    )
+
+    assert len(captured) == 1
+    assert b'name="quality"' not in captured[0].content
+    assert b'name="prompt"\r\n\r\nadd a hat' in captured[0].content
diff --git a/tests/test_litellm/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py b/tests/test_litellm/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py
index aff0530ee8b..5a29a96829f 100644
--- a/tests/test_litellm/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py
+++ b/tests/test_litellm/llms/openai/chat/guardrail_translation/test_openai_guardrail_handler.py
@@ -1113,6 +1113,102 @@ class TestOpenAIChatCompletionsHandlerStreamingOutput:
         assert chunks[1].choices[0].delta.content in (None, "")
         assert chunks[1].choices[0].finish_reason == "stop"
 
+    @staticmethod
+    def _ended_tool_call_stream_chunks() -> list:
+        from litellm.types.utils import (
+            ChatCompletionDeltaToolCall,
+            Delta,
+            Function,
+            ModelResponseStream,
+            StreamingChoices,
+        )
+
+        def chunk(tool_call: ChatCompletionDeltaToolCall | None, finish_reason: Optional[str] = None):
+            return ModelResponseStream(
+                id="chatcmpl-123",
+                created=1234567890,
+                model="gpt-4",
+                object="chat.completion.chunk",
+                choices=[
+                    StreamingChoices(
+                        index=0,
+                        delta=Delta(tool_calls=[tool_call] if tool_call else None),
+                        finish_reason=finish_reason,
+                    )
+                ],
+            )
+
+        def fragment(arguments: str, name: Optional[str] = None, call_id: Optional[str] = None):
+            return ChatCompletionDeltaToolCall(
+                id=call_id, index=0, type="function", function=Function(name=name, arguments=arguments)
+            )
+
+        return [
+            chunk(fragment("", name="lookup_fruit", call_id="call_1")),
+            chunk(fragment('{"fruit":')),
+            chunk(fragment(' "persimmon"}')),
+            chunk(None, finish_reason="tool_calls"),
+        ]
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_writes_tool_call_arguments_back_into_chunks(self):
+        handler = OpenAIChatCompletionsHandler()
+        guardrail = MockGuardrail(guardrail_name="test")
+        chunks = self._ended_tool_call_stream_chunks()
+
+        result = await handler.process_output_streaming_response(
+            responses_so_far=chunks,
+            guardrail_to_apply=guardrail,
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert result is chunks
+        fragments = [chunk.choices[0].delta.tool_calls for chunk in chunks[:3]]
+        assert [fragment[0].function.arguments for fragment in fragments] == ['{"fruit": "PERSIMMON"}', "", ""]
+        assert fragments[0][0].function.name == "lookup_fruit"
+        assert fragments[0][0].id == "call_1"
+        assert chunks[3].choices[0].delta.tool_calls is None
+        assert chunks[3].choices[0].finish_reason == "tool_calls"
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_writes_tool_call_name_back_into_chunks(self):
+        class RenameTool(CustomGuardrail):
+            async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+                for tool_call in inputs.get("tool_calls", []):
+                    tool_call["function"]["name"] = "lookup_fruit_reviewed"
+                return inputs
+
+        handler = OpenAIChatCompletionsHandler()
+        chunks = self._ended_tool_call_stream_chunks()
+
+        await handler.process_output_streaming_response(
+            responses_so_far=chunks,
+            guardrail_to_apply=RenameTool(guardrail_name="test"),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        fragments = [chunk.choices[0].delta.tool_calls[0] for chunk in chunks[:3]]
+        assert [fragment.function.name for fragment in fragments] == ["lookup_fruit_reviewed", None, None]
+        assert json.loads("".join(fragment.function.arguments for fragment in fragments)) == {"fruit": "persimmon"}
+        assert fragments[0].id == "call_1"
+
+    @pytest.mark.asyncio
+    async def test_ended_stream_tool_call_rewrite_leaves_chunks_untouched_by_default(self):
+        handler = OpenAIChatCompletionsHandler()
+        guardrail = MockGuardrail(guardrail_name="test")
+        chunks = self._ended_tool_call_stream_chunks()
+
+        await handler.process_output_streaming_response(
+            responses_so_far=chunks,
+            guardrail_to_apply=guardrail,
+            litellm_logging_obj=None,
+        )
+
+        fragments = [chunk.choices[0].delta.tool_calls for chunk in chunks[:3]]
+        assert [fragment[0].function.arguments for fragment in fragments] == ["", '{"fruit":', ' "persimmon"}']
+
     @pytest.mark.asyncio
     async def test_ended_stream_rewrite_leaves_chunks_untouched_by_default(self):
         handler = OpenAIChatCompletionsHandler()
@@ -1179,6 +1275,62 @@ class TestOpenAIChatCompletionsHandlerStreamingOutput:
                 deliver_ended_stream_rewrites=True,
             )
 
+    @staticmethod
+    def _two_choice_tool_call_stream_chunks() -> list:
+        from litellm.types.utils import (
+            ChatCompletionDeltaToolCall,
+            Delta,
+            Function,
+            ModelResponseStream,
+            StreamingChoices,
+        )
+
+        def chunk(
+            choice_index: int, tool_call: ChatCompletionDeltaToolCall | None, finish_reason: Optional[str] = None
+        ) -> ModelResponseStream:
+            return ModelResponseStream(
+                id="chatcmpl-123",
+                created=1234567890,
+                model="gpt-4",
+                object="chat.completion.chunk",
+                choices=[
+                    StreamingChoices(
+                        index=choice_index,
+                        delta=Delta(tool_calls=[tool_call] if tool_call else None),
+                        finish_reason=finish_reason,
+                    )
+                ],
+            )
+
+        def fragment(arguments: str, name: Optional[str] = None, call_id: Optional[str] = None):
+            return ChatCompletionDeltaToolCall(
+                id=call_id, index=0, type="function", function=Function(name=name, arguments=arguments)
+            )
+
+        return [
+            chunk(0, fragment("", name="lookup_fruit", call_id="call_1")),
+            chunk(1, fragment("", name="lookup_fruit", call_id="call_2")),
+            chunk(0, fragment('{"fruit": "persimmon"}')),
+            chunk(1, fragment('{"fruit": "durian"}')),
+            chunk(0, None, finish_reason="tool_calls"),
+            chunk(1, None, finish_reason="tool_calls"),
+        ]
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_tool_call_rewrite_on_multi_choice_stream_fails_closed(self):
+        from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+        handler = OpenAIChatCompletionsHandler()
+        chunks = self._two_choice_tool_call_stream_chunks()
+
+        with pytest.raises(UndeliverableStreamRewrite):
+            await handler.process_output_streaming_response(
+                responses_so_far=chunks,
+                guardrail_to_apply=MockGuardrail(guardrail_name="test"),
+                litellm_logging_obj=None,
+                deliver_ended_stream_rewrites=True,
+            )
+
     @pytest.mark.asyncio
     async def test_deliver_ended_stream_clean_multi_choice_stream_released_untouched(self):
         handler = OpenAIChatCompletionsHandler()
diff --git a/tests/test_litellm/llms/openai/chat/test_openai_gpt_transformation.py b/tests/test_litellm/llms/openai/chat/test_openai_gpt_transformation.py
index 9737d63cc26..b110586ae5b 100644
--- a/tests/test_litellm/llms/openai/chat/test_openai_gpt_transformation.py
+++ b/tests/test_litellm/llms/openai/chat/test_openai_gpt_transformation.py
@@ -4,6 +4,7 @@ Tests for OpenAI GPT transformation (litellm/llms/openai/chat/gpt_transformation
 
 
 import pytest
+from typing import Final
 
 
 import litellm
@@ -1168,6 +1169,9 @@ class TestOpenAIPromptCacheBreakpointChatPath:
         assert "prompt_cache_options" not in request
 
 
+_ARTIFACT_FIELD_PATTERN: Final = r'^(?!__.*__$)[^\p{Cc}\p{Cf}\p{Zl}\p{Zp}"\\./[\]]{1,200}$'
+
+
 class TestToolSchemaCombinatorFlatteningForOpenAI:
     """
     Regression tests for LIT-6488: OpenAI's chat completions validator rejects
@@ -1281,3 +1285,50 @@ class TestToolSchemaCombinatorFlatteningForOpenAI:
         parameters = request["tools"][0]["function"]["parameters"]
         assert "anyOf" not in parameters
         assert set(parameters["properties"]) == {"id", "enabled", "schedule"}
+
+    @staticmethod
+    def _artifact_tool():
+        return {
+            "type": "function",
+            "function": {
+                "name": "Artifact",
+                "parameters": {
+                    "type": "object",
+                    "properties": {"field": {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN}},
+                    "required": ["field"],
+                },
+            },
+        }
+
+    def test_drops_non_python_regex_pattern_for_hosted_openai(self):
+        tool = self._artifact_tool()
+
+        request = self._transform(self.config, "gpt-4o", {"custom_llm_provider": "openai", "api_base": None}, [tool])
+
+        assert request["tools"][0]["function"]["parameters"] == {
+            "type": "object",
+            "properties": {"field": {"type": "string"}},
+            "required": ["field"],
+        }
+        assert tool == self._artifact_tool()
+
+    def test_custom_api_base_drops_non_python_regex_pattern_but_keeps_union(self):
+        tool = self._anyof_tool()
+        tool["function"]["parameters"]["properties"]["id"]["pattern"] = _ARTIFACT_FIELD_PATTERN
+
+        request = self._transform(
+            self.config, "gpt-4o", {"custom_llm_provider": "openai", "api_base": "http://localhost:8000/v1"}, [tool]
+        )
+
+        parameters = request["tools"][0]["function"]["parameters"]
+        assert parameters["properties"]["id"] == {"type": "string"}
+        assert parameters["anyOf"] == self._anyof_tool()["function"]["parameters"]["anyOf"]
+
+    def test_non_openai_provider_keeps_non_python_regex_pattern(self):
+        tool = self._artifact_tool()
+
+        request = self._transform(
+            self.config, "some-oss-model", {"custom_llm_provider": "groq", "api_base": None}, [tool]
+        )
+
+        assert request["tools"][0] is tool
diff --git a/tests/test_litellm/llms/openai/responses/test_openai_responses_guardrail_handler.py b/tests/test_litellm/llms/openai/responses/test_openai_responses_guardrail_handler.py
index 33c8c97fea7..a4f0a77a9b6 100644
--- a/tests/test_litellm/llms/openai/responses/test_openai_responses_guardrail_handler.py
+++ b/tests/test_litellm/llms/openai/responses/test_openai_responses_guardrail_handler.py
@@ -10,23 +10,33 @@ from collections.abc import Callable
 from typing import Any, List, Literal, Optional, Tuple
 from unittest.mock import AsyncMock, MagicMock
 
+import logging
+
 import pytest
 
 
 from fastapi import HTTPException
-from openai.types.responses import ResponseFunctionToolCall
+from pydantic import BaseModel
+from openai.types.responses import (
+    ResponseCustomToolCall,
+    ResponseCustomToolCallInputDeltaEvent,
+    ResponseCustomToolCallInputDoneEvent,
+    ResponseFunctionToolCall,
+)
 
 from litellm.integrations.custom_guardrail import CustomGuardrail
+from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
 from litellm.llms import get_guardrail_translation_mapping
 from litellm.llms.openai.responses.guardrail_translation.handler import (
     OpenAIResponsesHandler,
 )
 from litellm.llms.openai.responses.guardrail_translation.tool_merge import merge_guardrailed_tools
+from litellm.types.llms.openai import ChatCompletionToolCallChunk
 from litellm.responses.litellm_completion_transformation.transformation import (
     LiteLLMCompletionResponsesConfig,
 )
 from litellm.types.llms.openai import ResponsesAPIResponse
-from litellm.types.responses.main import GenericResponseOutputItem, OutputText
+from litellm.types.responses.main import CustomToolCallOutputItem, GenericResponseOutputItem, OutputText
 from litellm.types.utils import CallTypes, GenericGuardrailAPIInputs
 
 
@@ -56,6 +66,60 @@ class MockGuardrail(CustomGuardrail):
         return inputs
 
 
+class PersimmonMaskingGuardrail(CustomGuardrail):
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict,
+        input_type: Literal["request", "response"],
+        logging_obj: Optional[LiteLLMLoggingObj] = None,
+    ) -> GenericGuardrailAPIInputs:
+        tool_calls = [
+            {
+                **tool_call,
+                "function": {
+                    **tool_call["function"],
+                    "arguments": tool_call["function"]["arguments"].replace("persimmon", "[MASKED]"),
+                },
+            }
+            for tool_call in inputs.get("tool_calls", [])
+        ]
+        return {**inputs, "tool_calls": tool_calls}
+
+
+class FlatShapeGuardrail(CustomGuardrail):
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict,
+        input_type: Literal["request", "response"],
+        logging_obj: Optional[LiteLLMLoggingObj] = None,
+    ) -> GenericGuardrailAPIInputs:
+        flat_tool_calls = [{"name": "exec", "input": "rm -rf /"} for _ in inputs.get("tool_calls", [])]
+        return {**inputs, "tool_calls": flat_tool_calls}
+
+
+class DroppingGuardrail(CustomGuardrail):
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict,
+        input_type: Literal["request", "response"],
+        logging_obj: Optional[LiteLLMLoggingObj] = None,
+    ) -> GenericGuardrailAPIInputs:
+        return {**inputs, "tool_calls": []}
+
+
+CUSTOM_TOOL_CALL_ITEM = {
+    "type": "custom_tool_call",
+    "id": "ctc_1",
+    "call_id": "call_exec_1",
+    "name": "exec",
+    "input": "echo persimmon",
+    "status": "completed",
+}
+
+
 class TestOpenAIResponsesHandlerDiscovery:
     """Test that the handler is properly discovered by the guardrail system"""
 
@@ -556,7 +620,7 @@ class TestOpenAIResponsesHandlerToolCallExtraction:
 
         texts_to_check: List[str] = []
         images_to_check: List[str] = []
-        tool_calls_to_check: List[Any] = []
+        tool_calls_to_check: List[ChatCompletionToolCallChunk] = []
         task_mappings: List[Tuple[int, int]] = []
 
         # Extract tool calls
@@ -627,6 +691,123 @@ class TestOpenAIResponsesHandlerToolCallExtraction:
             == '{"location":"Boston, MA","unit":"celsius"}'
         )
 
+    @pytest.mark.parametrize(
+        "output_item",
+        [
+            dict(CUSTOM_TOOL_CALL_ITEM),
+            CustomToolCallOutputItem(**CUSTOM_TOOL_CALL_ITEM),
+            ResponseCustomToolCall(**{key: value for key, value in CUSTOM_TOOL_CALL_ITEM.items() if key != "status"}),
+        ],
+        ids=["dict", "litellm_typed", "openai_typed"],
+    )
+    def test_extract_custom_tool_call_input_as_arguments(self, output_item):
+        handler = OpenAIResponsesHandler()
+        texts_to_check: List[str] = []
+        tool_calls_to_check: List[Any] = []
+
+        handler._extract_output_text_and_images(
+            output_item=output_item,
+            output_idx=2,
+            texts_to_check=texts_to_check,
+            images_to_check=[],
+            task_mappings=[],
+            tool_calls_to_check=tool_calls_to_check,
+        )
+
+        assert texts_to_check == []
+        assert tool_calls_to_check == [
+            {
+                "id": "call_exec_1",
+                "type": "function",
+                "function": {"name": "exec", "arguments": "echo persimmon"},
+                "index": 2,
+            }
+        ]
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("typed", [False, True], ids=["dict", "typed"])
+    async def test_process_output_response_writes_tool_call_rewrites_back(self, typed):
+        handler = OpenAIResponsesHandler()
+        function_call = {
+            "type": "function_call",
+            "id": "fc_1",
+            "call_id": "call_fn_1",
+            "name": "lookup_fruit",
+            "arguments": '{"fruit": "persimmon"}',
+            "status": "completed",
+        }
+        message = {
+            "type": "message",
+            "id": "msg_1",
+            "role": "assistant",
+            "status": "completed",
+            "content": [{"type": "output_text", "text": "running persimmon", "annotations": []}],
+        }
+        payload = {
+            "id": "resp_1",
+            "created_at": 1,
+            "model": "gpt-5.6",
+            "object": "response",
+            "status": "completed",
+            "output": [message, function_call, dict(CUSTOM_TOOL_CALL_ITEM)],
+        }
+        response = ResponsesAPIResponse.model_validate(payload) if typed else payload
+
+        result = await handler.process_output_response(response, PersimmonMaskingGuardrail(guardrail_name="mask"))
+
+        output = result.output if typed else result["output"]
+        function_item, custom_item = output[1], output[2]
+        assert (function_item.arguments if typed else function_item["arguments"]) == '{"fruit": "[MASKED]"}'
+        assert (custom_item.input if typed else custom_item["input"]) == "echo [MASKED]"
+        assert (custom_item.name if typed else custom_item["name"]) == "exec"
+        assert (output[0].content[0].text if typed else output[0]["content"][0]["text"]) == "running persimmon"
+
+    @staticmethod
+    def _custom_tool_call_response(item: dict) -> dict:
+        return {
+            "id": "resp_1",
+            "created_at": 1,
+            "model": "gpt-5.6",
+            "object": "response",
+            "status": "completed",
+            "output": [item],
+        }
+
+    @pytest.mark.asyncio
+    async def test_process_output_response_ignores_tool_call_rewrites_in_another_shape(self):
+        handler = OpenAIResponsesHandler()
+        response = self._custom_tool_call_response(dict(CUSTOM_TOOL_CALL_ITEM))
+
+        result = await handler.process_output_response(response, FlatShapeGuardrail(guardrail_name="flat"))
+
+        assert result["output"][0]["input"] == "echo persimmon"
+        assert result["output"][0]["name"] == "exec"
+
+    @pytest.mark.asyncio
+    async def test_process_output_response_warns_when_guardrail_drops_tool_calls(self, caplog):
+        handler = OpenAIResponsesHandler()
+        response = self._custom_tool_call_response(dict(CUSTOM_TOOL_CALL_ITEM))
+
+        with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+            result = await handler.process_output_response(response, DroppingGuardrail(guardrail_name="dropper"))
+
+        assert result["output"][0]["input"] == "echo persimmon"
+        assert any(
+            "dropper" in record.getMessage() and "0 tool calls for the 1 scanned" in record.getMessage()
+            for record in caplog.records
+        )
+
+    @pytest.mark.asyncio
+    async def test_process_output_response_keeps_a_nameless_custom_tool_call_nameless(self):
+        handler = OpenAIResponsesHandler()
+        nameless_item = {key: value for key, value in CUSTOM_TOOL_CALL_ITEM.items() if key != "name"}
+        response = self._custom_tool_call_response(nameless_item)
+
+        result = await handler.process_output_response(response, PersimmonMaskingGuardrail(guardrail_name="mask"))
+
+        assert result["output"][0]["input"] == "echo [MASKED]"
+        assert "name" not in result["output"][0]
+
     @pytest.mark.asyncio
     async def test_process_output_response_with_tool_calls(self):
         """Test processing output response containing function tool calls"""
@@ -1195,6 +1376,352 @@ class TestOpenAIResponsesHandlerStreamingOutputProcessing:
         assert events[4]["item"]["content"][0]["text"] == "hello [MASKED]"
         assert events[5]["response"]["output"][0]["content"][0]["text"] == "hello [MASKED]"
 
+    @staticmethod
+    def _ended_function_call_stream_events() -> List[dict]:
+        def item(arguments: str, status: str) -> dict:
+            return {
+                "type": "function_call",
+                "id": "fc_123",
+                "call_id": "call_123",
+                "name": "lookup_fruit",
+                "arguments": arguments,
+                "status": status,
+            }
+
+        return [
+            {"type": "response.output_item.added", "output_index": 0, "item": item("", "in_progress")},
+            {"type": "response.function_call_arguments.delta", "item_id": "fc_123", "output_index": 0, "delta": '{"fruit":'},
+            {"type": "response.function_call_arguments.delta", "item_id": "fc_123", "output_index": 0, "delta": ' "persimmon"}'},
+            {
+                "type": "response.function_call_arguments.done",
+                "item_id": "fc_123",
+                "output_index": 0,
+                "arguments": '{"fruit": "persimmon"}',
+            },
+            {"type": "response.output_item.done", "output_index": 0, "item": item('{"fruit": "persimmon"}', "completed")},
+            {
+                "type": "response.completed",
+                "response": {
+                    "id": "resp_123",
+                    "created_at": 1,
+                    "model": "gpt-4o",
+                    "output": [item('{"fruit": "persimmon"}', "completed")],
+                    "status": "completed",
+                },
+            },
+        ]
+
+    @staticmethod
+    def _argument_masking_guardrail() -> CustomGuardrail:
+        class MaskArguments(CustomGuardrail):
+            async def apply_guardrail(
+                self,
+                inputs: GenericGuardrailAPIInputs,
+                request_data: dict,
+                input_type: Literal["request", "response"],
+                logging_obj: LiteLLMLoggingObj | None = None,
+            ) -> GenericGuardrailAPIInputs:
+                tool_calls = [
+                    {**tool_call, "function": {**tool_call["function"], "arguments": '{"fruit": "[MASKED]"}'}}
+                    for tool_call in inputs.get("tool_calls", [])
+                ]
+                return {**inputs, "tool_calls": tool_calls}
+
+        return MaskArguments(guardrail_name="test-mask-arguments")
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_syncs_function_call_events(self):
+        handler = OpenAIResponsesHandler()
+        events = self._ended_function_call_stream_events()
+
+        result = await handler.process_output_streaming_response(
+            responses_so_far=events,
+            guardrail_to_apply=self._argument_masking_guardrail(),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert result is events
+        assert events[0]["item"]["arguments"] == ""
+        assert events[1]["delta"] == '{"fruit": "[MASKED]"}'
+        assert events[2]["delta"] == ""
+        assert events[3]["arguments"] == '{"fruit": "[MASKED]"}'
+        assert events[4]["item"]["arguments"] == '{"fruit": "[MASKED]"}'
+        assert events[5]["response"]["output"][0]["arguments"] == '{"fruit": "[MASKED]"}'
+        assert events[5]["response"]["output"][0]["name"] == "lookup_fruit"
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_syncs_typed_function_call_events(self):
+        from litellm.types.llms.openai import (
+            FunctionCallArgumentsDeltaEvent,
+            FunctionCallArgumentsDoneEvent,
+            OutputItemAddedEvent,
+            OutputItemDoneEvent,
+            ResponseCompletedEvent,
+            ResponsesAPIResponse,
+        )
+
+        handler = OpenAIResponsesHandler()
+        typed_events: List[Any] = [
+            model.model_validate(event)
+            for model, event in zip(
+                (
+                    OutputItemAddedEvent,
+                    FunctionCallArgumentsDeltaEvent,
+                    FunctionCallArgumentsDeltaEvent,
+                    FunctionCallArgumentsDoneEvent,
+                    OutputItemDoneEvent,
+                    ResponseCompletedEvent,
+                ),
+                self._ended_function_call_stream_events(),
+            )
+        ]
+        completed_event = typed_events[5]
+        assert isinstance(completed_event, ResponseCompletedEvent)
+        assert isinstance(completed_event.response, ResponsesAPIResponse)
+        assert isinstance(completed_event.response.output[0], ResponseFunctionToolCall)
+
+        await handler.process_output_streaming_response(
+            responses_so_far=typed_events,
+            guardrail_to_apply=self._argument_masking_guardrail(),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert typed_events[1].delta == '{"fruit": "[MASKED]"}'
+        assert typed_events[2].delta == ""
+        assert typed_events[3].arguments == '{"fruit": "[MASKED]"}'
+        assert typed_events[4].item.arguments == '{"fruit": "[MASKED]"}'
+        assert completed_event.response.output[0].arguments == '{"fruit": "[MASKED]"}'
+        assert completed_event.response.output[0].name == "lookup_fruit"
+
+    @staticmethod
+    def _ended_custom_tool_call_stream_events() -> List[dict]:
+        def item(input_text: str, status: str) -> dict:
+            return {**CUSTOM_TOOL_CALL_ITEM, "input": input_text, "status": status}
+
+        return [
+            {"type": "response.output_item.added", "output_index": 0, "item": item("", "in_progress")},
+            {"type": "response.custom_tool_call_input.delta", "item_id": "ctc_1", "output_index": 0, "delta": "echo "},
+            {"type": "response.custom_tool_call_input.delta", "item_id": "ctc_1", "output_index": 0, "delta": "persimmon"},
+            {"type": "response.custom_tool_call_input.done", "item_id": "ctc_1", "output_index": 0, "input": "echo persimmon"},
+            {"type": "response.output_item.done", "output_index": 0, "item": item("echo persimmon", "completed")},
+            {
+                "type": "response.completed",
+                "response": {
+                    "id": "resp_123",
+                    "created_at": 1,
+                    "model": "gpt-5.6",
+                    "output": [item("echo persimmon", "completed")],
+                    "status": "completed",
+                },
+            },
+        ]
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_syncs_custom_tool_call_events(self):
+        handler = OpenAIResponsesHandler()
+        events = self._ended_custom_tool_call_stream_events()
+
+        result = await handler.process_output_streaming_response(
+            responses_so_far=events,
+            guardrail_to_apply=PersimmonMaskingGuardrail(guardrail_name="mask"),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert result is events
+        assert events[0]["item"]["input"] == ""
+        assert events[1]["delta"] == "echo [MASKED]"
+        assert events[2]["delta"] == ""
+        assert events[3]["input"] == "echo [MASKED]"
+        assert events[4]["item"]["input"] == "echo [MASKED]"
+        assert events[5]["response"]["output"][0]["input"] == "echo [MASKED]"
+        assert events[5]["response"]["output"][0]["name"] == "exec"
+        assert "arguments" not in events[5]["response"]["output"][0]
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_keep_a_nameless_custom_tool_call_nameless(self):
+        handler = OpenAIResponsesHandler()
+        events = self._ended_custom_tool_call_stream_events()
+        items = [events[0]["item"], events[4]["item"], events[5]["response"]["output"][0]]
+        for item in items:
+            del item["name"]
+
+        await handler.process_output_streaming_response(
+            responses_so_far=events,
+            guardrail_to_apply=PersimmonMaskingGuardrail(guardrail_name="mask"),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert events[3]["input"] == "echo [MASKED]"
+        assert events[5]["response"]["output"][0]["input"] == "echo [MASKED]"
+        assert all("name" not in item for item in items)
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_syncs_typed_custom_tool_call_events(self):
+        from litellm.types.llms.openai import (
+            OutputItemAddedEvent,
+            OutputItemDoneEvent,
+            ResponseCompletedEvent,
+        )
+
+        handler = OpenAIResponsesHandler()
+        typed_events: List[BaseModel] = [
+            model.model_validate({**event, "sequence_number": sequence_number})
+            for sequence_number, (model, event) in enumerate(
+                zip(
+                    (
+                        OutputItemAddedEvent,
+                        ResponseCustomToolCallInputDeltaEvent,
+                        ResponseCustomToolCallInputDeltaEvent,
+                        ResponseCustomToolCallInputDoneEvent,
+                        OutputItemDoneEvent,
+                        ResponseCompletedEvent,
+                    ),
+                    self._ended_custom_tool_call_stream_events(),
+                )
+            )
+        ]
+        completed_event = typed_events[5]
+        assert isinstance(completed_event.response.output[0], CustomToolCallOutputItem)
+
+        await handler.process_output_streaming_response(
+            responses_so_far=typed_events,
+            guardrail_to_apply=PersimmonMaskingGuardrail(guardrail_name="mask"),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert typed_events[1].delta == "echo [MASKED]"
+        assert typed_events[2].delta == ""
+        assert typed_events[3].input == "echo [MASKED]"
+        assert typed_events[4].item.input == "echo [MASKED]"
+        assert completed_event.response.output[0].input == "echo [MASKED]"
+        assert completed_event.response.output[0].name == "exec"
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_custom_tool_call_rewrite_without_matching_events_fails_closed(self):
+        from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+        handler = OpenAIResponsesHandler()
+        events = self._ended_custom_tool_call_stream_events()
+        events[5]["response"]["output"] = [{**events[5]["response"]["output"][0], "call_id": "call_999"}]
+
+        with pytest.raises(UndeliverableStreamRewrite):
+            await handler.process_output_streaming_response(
+                responses_so_far=events,
+                guardrail_to_apply=PersimmonMaskingGuardrail(guardrail_name="mask"),
+                litellm_logging_obj=None,
+                deliver_ended_stream_rewrites=True,
+            )
+
+    @staticmethod
+    def _bridged_function_call_stream_events() -> List[dict]:
+        reasoning = {"type": "reasoning", "id": "rs_1", "summary": []}
+        text = {"type": "output_text", "text": "Looking that up", "annotations": []}
+        message = {"type": "message", "id": "msg_1", "role": "assistant", "status": "completed", "content": [text]}
+
+        def function_call(arguments: str, status: str) -> dict:
+            return {
+                "type": "function_call",
+                "id": "fc_1",
+                "call_id": "call_1",
+                "name": "lookup_fruit",
+                "arguments": arguments,
+                "status": status,
+            }
+
+        return [
+            {"type": "response.output_item.added", "output_index": 0, "item": dict(reasoning)},
+            {"type": "response.output_item.done", "output_index": 0, "item": dict(reasoning)},
+            {"type": "response.output_item.added", "output_index": 0, "item": {**message, "status": "in_progress", "content": []}},
+            {"type": "response.output_text.delta", "item_id": "msg_1", "output_index": 0, "content_index": 0, "delta": "Looking that up"},
+            {"type": "response.output_item.done", "output_index": 0, "item": {**message, "content": [dict(text)]}},
+            {"type": "response.output_item.added", "output_index": 1, "item": function_call("", "in_progress")},
+            {"type": "response.function_call_arguments.delta", "item_id": "fc_1", "output_index": 1, "delta": '{"fruit":'},
+            {"type": "response.function_call_arguments.delta", "item_id": "fc_1", "output_index": 1, "delta": ' "persimmon"}'},
+            {
+                "type": "response.function_call_arguments.done",
+                "item_id": "fc_1",
+                "output_index": 1,
+                "arguments": '{"fruit": "persimmon"}',
+            },
+            {"type": "response.output_item.done", "output_index": 1, "item": function_call('{"fruit": "persimmon"}', "completed")},
+            {
+                "type": "response.completed",
+                "response": {
+                    "id": "resp_1",
+                    "model": "claude-haiku-4-5",
+                    "output": [
+                        dict(reasoning),
+                        {**message, "content": [dict(text)]},
+                        function_call('{"fruit": "persimmon"}', "completed"),
+                    ],
+                },
+            },
+        ]
+
+    @pytest.mark.asyncio
+    async def test_deliver_ended_stream_rewrites_keys_bridged_function_call_events_by_call_id(self):
+        handler = OpenAIResponsesHandler()
+        events = self._bridged_function_call_stream_events()
+
+        await handler.process_output_streaming_response(
+            responses_so_far=events,
+            guardrail_to_apply=self._argument_masking_guardrail(),
+            litellm_logging_obj=None,
+            deliver_ended_stream_rewrites=True,
+        )
+
+        assert events[6]["delta"] == '{"fruit": "[MASKED]"}'
+        assert events[7]["delta"] == ""
+        assert events[8]["arguments"] == '{"fruit": "[MASKED]"}'
+        assert events[5]["item"]["name"] == "lookup_fruit"
+        assert events[9]["item"]["arguments"] == '{"fruit": "[MASKED]"}'
+        assert events[10]["response"]["output"][2]["arguments"] == '{"fruit": "[MASKED]"}'
+        assert events[3]["delta"] == "Looking that up"
+        assert events[4]["item"]["content"][0]["text"] == "Looking that up"
+        assert events[10]["response"]["output"][1]["content"][0]["text"] == "Looking that up"
+        assert events[1]["item"] == {"type": "reasoning", "id": "rs_1", "summary": []}
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("mismatch", ["orphan_call_id", "duplicate_call_id"])
+    async def test_deliver_ended_stream_function_call_rewrite_without_matching_events_fails_closed(self, mismatch):
+        from litellm.proxy.policy_engine.pipeline_executor import UndeliverableStreamRewrite
+
+        handler = OpenAIResponsesHandler()
+        events = self._ended_function_call_stream_events()
+        envelope_item = events[5]["response"]["output"][0]
+        if mismatch == "orphan_call_id":
+            events[5]["response"]["output"] = [{**envelope_item, "call_id": "call_999"}]
+        else:
+            events[5]["response"]["output"] = [dict(envelope_item), dict(envelope_item)]
+
+        with pytest.raises(UndeliverableStreamRewrite):
+            await handler.process_output_streaming_response(
+                responses_so_far=events,
+                guardrail_to_apply=self._argument_masking_guardrail(),
+                litellm_logging_obj=None,
+                deliver_ended_stream_rewrites=True,
+            )
+
+    @pytest.mark.asyncio
+    async def test_ended_stream_function_call_rewrite_leaves_events_untouched_by_default(self):
+        handler = OpenAIResponsesHandler()
+        events = self._ended_function_call_stream_events()
+
+        await handler.process_output_streaming_response(
+            responses_so_far=events,
+            guardrail_to_apply=self._argument_masking_guardrail(),
+            litellm_logging_obj=None,
+        )
+
+        assert events[1]["delta"] == '{"fruit":'
+        assert events[3]["arguments"] == '{"fruit": "persimmon"}'
+        assert events[5]["response"]["output"][0]["arguments"] == '{"fruit": "persimmon"}'
+
     @pytest.mark.asyncio
     @pytest.mark.parametrize("terminal_type", ["response.incomplete", "response.failed"])
     async def test_deliver_ended_stream_rewrites_syncs_non_completed_terminals(self, terminal_type):
@@ -2522,8 +3049,21 @@ class TestOpenAIResponsesHandlerStreamingScanKey:
         assert len(ended_key.tool_calls) == 1 and "get_weather" in ended_key.tool_calls[0]
         assert ended_key != open_key
 
+    def test_completed_event_with_a_custom_tool_call_changes_the_key(self):
+        handler = OpenAIResponsesHandler()
+        message = {"type": "message", "content": [{"type": "output_text", "text": "hi"}]}
+        ended_key = handler.get_streaming_scan_key(
+            [self._delta(0, "hi"), self._completed(1, [message, dict(CUSTOM_TOOL_CALL_ITEM)])]
+        )
+        rewritten_key = handler.get_streaming_scan_key(
+            [self._delta(0, "hi"), self._completed(1, [message, {**CUSTOM_TOOL_CALL_ITEM, "input": "echo kumquat"}])]
+        )
+        assert ended_key.texts == ("hi",)
+        assert len(ended_key.tool_calls) == 1 and "echo persimmon" in ended_key.tool_calls[0]
+        assert rewritten_key != ended_key
+
     def test_completed_event_reads_every_output_text_part(self):
-        from litellm.types.responses.main import GenericResponseOutputItem, OutputText
+        from litellm.types.responses.main import CustomToolCallOutputItem, GenericResponseOutputItem, OutputText
 
         item = GenericResponseOutputItem(
             type="message",
diff --git a/tests/test_litellm/llms/openai/responses/test_openai_responses_transformation.py b/tests/test_litellm/llms/openai/responses/test_openai_responses_transformation.py
index c5902b32a06..4cf8767764b 100644
--- a/tests/test_litellm/llms/openai/responses/test_openai_responses_transformation.py
+++ b/tests/test_litellm/llms/openai/responses/test_openai_responses_transformation.py
@@ -1,5 +1,6 @@
 import json
 from types import SimpleNamespace
+from typing import Final
 from unittest.mock import AsyncMock, MagicMock, Mock, patch
 
 import httpx
@@ -20,6 +21,8 @@ from litellm.types.llms.openai import (
 )
 from litellm.types.router import GenericLiteLLMParams
 
+_ARTIFACT_FIELD_PATTERN: Final = r'^(?!__.*__$)[^\p{Cc}\p{Cf}\p{Zl}\p{Zp}"\\./[\]]{1,200}$'
+
 
 class TestOpenAIResponsesAPIConfig:
     def setup_method(self):
@@ -2022,6 +2025,86 @@ class TestFlattenToolSchemaCombinatorsWiring:
         assert "anyOf" not in result["tools"][1]["parameters"]
 
 
+class TestToolSchemaRegexPatternWiring:
+    """Claude Code's Artifact tool reaches /v1/responses (the /v1/messages bridge) with an
+    ECMA-262 ``pattern``; OpenAI compiles patterns with Python ``re`` and 400s
+    "'...' is not a 'regex'" for every model family, so the keyword is dropped.
+    """
+
+    def _artifact_tool(self):
+        return {
+            "type": "function",
+            "name": "Artifact",
+            "parameters": {
+                "type": "object",
+                "properties": {
+                    "field": {"type": "string", "pattern": _ARTIFACT_FIELD_PATTERN},
+                    "doc_id": {"type": "string", "pattern": r"^(?!\.\.?(?:/|$))[A-Za-z0-9_\-.~:@+]{1,200}$"},
+                },
+                "required": ["field"],
+            },
+        }
+
+    @pytest.mark.parametrize("model", ["gpt-5.6", "gpt-4o", "o3"])
+    def test_openai_drops_only_the_pattern_python_re_rejects_for_every_family(self, model):
+        tool = self._artifact_tool()
+
+        result = OpenAIResponsesAPIConfig().transform_responses_api_request(
+            model=model,
+            input="hi",
+            response_api_optional_request_params={"tools": [tool]},
+            litellm_params=GenericLiteLLMParams(),
+            headers={},
+        )
+
+        properties = result["tools"][0]["parameters"]["properties"]
+        assert properties["field"] == {"type": "string"}
+        assert properties["doc_id"] == tool["parameters"]["properties"]["doc_id"]
+        assert result["tools"][0]["parameters"]["required"] == ["field"]
+        assert tool["parameters"]["properties"]["field"]["pattern"] == _ARTIFACT_FIELD_PATTERN
+        assert json.loads(json.dumps(result["tools"])) == result["tools"]
+
+    def test_openai_drops_patterns_inside_codex_namespace_tools(self):
+        namespace = {"type": "namespace", "name": "mcp__claude", "tools": [self._artifact_tool()]}
+
+        result = OpenAIResponsesAPIConfig().transform_responses_api_request(
+            model="gpt-5.6",
+            input="hi",
+            response_api_optional_request_params={"tools": [namespace]},
+            litellm_params=GenericLiteLLMParams(),
+            headers={},
+        )
+
+        assert result["tools"][0]["tools"][0]["parameters"]["properties"]["field"] == {"type": "string"}
+
+    def test_openai_compact_request_drops_patterns(self):
+        _, data = OpenAIResponsesAPIConfig().transform_compact_response_api_request(
+            model="gpt-5.6",
+            input="hi",
+            response_api_optional_request_params={"tools": [self._artifact_tool()]},
+            api_base="https://api.openai.com/v1/responses",
+            litellm_params=GenericLiteLLMParams(),
+            headers={},
+        )
+
+        assert data["tools"][0]["parameters"]["properties"]["field"] == {"type": "string"}
+
+    def test_non_openai_subclass_keeps_patterns(self):
+        from litellm.llms.hosted_vllm.responses.transformation import HostedVLLMResponsesAPIConfig
+
+        tool = self._artifact_tool()
+
+        result = HostedVLLMResponsesAPIConfig().transform_responses_api_request(
+            model="hosted_vllm/qwen",
+            input="hi",
+            response_api_optional_request_params={"tools": [tool]},
+            litellm_params=GenericLiteLLMParams(),
+            headers={},
+        )
+
+        assert result["tools"][0] is tool
+
+
 class TestReasoningFollowsModelSupport:
     """Responses API clients like Codex send `reasoning` on every request, and OpenAI 400s it
     on non-reasoning models like gpt-4o. drop_params must strip it there, the same way the
diff --git a/tests/test_litellm/llms/openai/test_gpt5_transformation.py b/tests/test_litellm/llms/openai/test_gpt5_transformation.py
index c86ce4df2ac..b538fad71a2 100644
--- a/tests/test_litellm/llms/openai/test_gpt5_transformation.py
+++ b/tests/test_litellm/llms/openai/test_gpt5_transformation.py
@@ -276,6 +276,17 @@ def test_gpt5_drops_reasoning_effort_xhigh_when_requested(config: OpenAIConfig):
     assert "reasoning_effort" not in params
 
 
+def test_gpt5_1_gpt5_2_gpt5_4_drop_minimal_reasoning_effort(config: OpenAIConfig):
+    for model in ("gpt-5.1", "gpt-5.2", "gpt-5.4", "gpt-5.4-pro"):
+        params = config.map_openai_params(
+            non_default_params={"reasoning_effort": "minimal"},
+            optional_params={},
+            model=model,
+            drop_params=True,
+        )
+        assert "reasoning_effort" not in params
+
+
 # GPT-5.1 temperature handling tests
 def test_gpt5_1_model_detection(gpt5_config: OpenAIGPT5Config):
     """Test that models supporting reasoning_effort='none' are correctly detected via model map."""
@@ -388,26 +399,26 @@ def test_gpt5_4_mini_allows_reasoning_effort_none(config: OpenAIConfig):
     assert params["reasoning_effort"] == "none"
 
 
-def test_gpt5_4_allows_reasoning_effort_minimal(config: OpenAIConfig):
-    """gpt-5.4 supports reasoning_effort='minimal'."""
-    params = config.map_openai_params(
-        non_default_params={"reasoning_effort": "minimal"},
-        optional_params={},
-        model="gpt-5.4",
-        drop_params=False,
-    )
-    assert params["reasoning_effort"] == "minimal"
+def test_gpt5_4_rejects_reasoning_effort_minimal(config: OpenAIConfig):
+    """gpt-5.4 rejects reasoning_effort='minimal'."""
+    with pytest.raises(litellm.utils.UnsupportedParamsError):
+        config.map_openai_params(
+            non_default_params={"reasoning_effort": "minimal"},
+            optional_params={},
+            model="gpt-5.4",
+            drop_params=False,
+        )
 
 
-def test_gpt5_4_pro_allows_reasoning_effort_minimal(config: OpenAIConfig):
-    """gpt-5.4-pro supports reasoning_effort='minimal'."""
-    params = config.map_openai_params(
-        non_default_params={"reasoning_effort": "minimal"},
-        optional_params={},
-        model="gpt-5.4-pro",
-        drop_params=False,
-    )
-    assert params["reasoning_effort"] == "minimal"
+def test_gpt5_4_pro_rejects_reasoning_effort_minimal(config: OpenAIConfig):
+    """gpt-5.4-pro rejects reasoning_effort='minimal'."""
+    with pytest.raises(litellm.utils.UnsupportedParamsError):
+        config.map_openai_params(
+            non_default_params={"reasoning_effort": "minimal"},
+            optional_params={},
+            model="gpt-5.4-pro",
+            drop_params=False,
+        )
 
 
 def test_gpt5_4_mini_rejects_reasoning_effort_minimal(config: OpenAIConfig):
@@ -468,13 +479,13 @@ def test_gpt5_minimal_dict_triggers_validation(config: OpenAIConfig):
 
 
 def test_gpt5_minimal_dict_accepted_for_supported_model(config: OpenAIConfig):
-    """Dict with effort='minimal' passes through for gpt-5.4+."""
+    """Dict with effort='minimal' passes through for gpt-5."""
     params = config.map_openai_params(
         non_default_params={
             "reasoning_effort": {"effort": "minimal", "summary": "detailed"}
         },
         optional_params={},
-        model="gpt-5.4",
+        model="gpt-5",
         drop_params=False,
     )
     assert params["reasoning_effort"] == "minimal"
@@ -482,8 +493,8 @@ def test_gpt5_minimal_dict_accepted_for_supported_model(config: OpenAIConfig):
 
 def test_gpt5_supports_reasoning_effort_level_minimal(gpt5_config: OpenAIGPT5Config):
     """Test that _supports_reasoning_effort_level correctly identifies minimal support."""
-    assert gpt5_config._supports_reasoning_effort_level("gpt-5.4", "minimal")
-    assert gpt5_config._supports_reasoning_effort_level("gpt-5.4-pro", "minimal")
+    assert not gpt5_config._supports_reasoning_effort_level("gpt-5.4", "minimal")
+    assert not gpt5_config._supports_reasoning_effort_level("gpt-5.4-pro", "minimal")
     assert not gpt5_config._supports_reasoning_effort_level("gpt-5.4-mini", "minimal")
     assert not gpt5_config._supports_reasoning_effort_level("gpt-5.4-nano", "minimal")
 
@@ -504,10 +515,10 @@ def test_gpt5_minimal_explicitly_disabled_check(gpt5_config: OpenAIGPT5Config):
     assert gpt5_config._is_reasoning_effort_level_explicitly_disabled(
         "openai/gpt-5.4-mini", "minimal"
     )
-    assert not gpt5_config._is_reasoning_effort_level_explicitly_disabled(
+    assert gpt5_config._is_reasoning_effort_level_explicitly_disabled(
         "gpt-5.4", "minimal"
     )
-    assert not gpt5_config._is_reasoning_effort_level_explicitly_disabled(
+    assert gpt5_config._is_reasoning_effort_level_explicitly_disabled(
         "gpt-5.4-pro", "minimal"
     )
 
@@ -523,8 +534,8 @@ def test_is_explicitly_disabled_factory_minimal():
     assert _is_explicitly_disabled_factory("gpt-5.4-mini", None, key)
     assert _is_explicitly_disabled_factory("gpt-5.4-nano", None, key)
     assert _is_explicitly_disabled_factory("openai/gpt-5.4-mini", None, key)
-    assert not _is_explicitly_disabled_factory("gpt-5.4", None, key)
-    assert not _is_explicitly_disabled_factory("gpt-5.4-pro", None, key)
+    assert _is_explicitly_disabled_factory("gpt-5.4", None, key)
+    assert _is_explicitly_disabled_factory("gpt-5.4-pro", None, key)
     assert not _is_explicitly_disabled_factory("gpt-5.4-turbo-preview", None, key)
 
 
diff --git a/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_handler.py b/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_handler.py
index aa1a59d0e5c..bb891c06fa2 100644
--- a/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_handler.py
+++ b/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_handler.py
@@ -46,3 +46,45 @@ def test_load_credentials_assumes_role_with_external_id(monkeypatch):
     assert credentials.token == "assumed-session-token"
     assert aws_region_name == "us-east-1"
     assert "aws_external_id" not in optional_params
+
+
+def test_load_credentials_assumes_role_with_session_tags(monkeypatch):
+    """A trust policy gated on sts:TagSession only admits the session when the deployment's tags are sent."""
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+
+    class FakeSTSClient:
+        def get_caller_identity(self):
+            return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+        def assume_role(self, **params):
+            if list(params.get("Tags", ())) != tags:
+                raise ClientError(
+                    {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                    "AssumeRole",
+                )
+            return {
+                "Credentials": {
+                    "AccessKeyId": "ASIASMCHATTAGGED",
+                    "SecretAccessKey": "assumed-secret",
+                    "SessionToken": "assumed-session-token",
+                    "Expiration": datetime.datetime.now(datetime.timezone.utc) + datetime.timedelta(minutes=30),
+                }
+            }
+
+    optional_params = {
+        "aws_access_key_id": "AKIASMCHATCALLERKEY",
+        "aws_secret_access_key": "pod-caller-secret",
+        "aws_region_name": "us-east-1",
+        "aws_role_name": "arn:aws:iam::999999999999:role/litellm-sm-chat-role",
+        "aws_session_name": "litellm-sm-chat-session",
+        "aws_session_tags": tags,
+    }
+
+    with patch.object(boto3, "client", return_value=FakeSTSClient()):
+        credentials, aws_region_name = SagemakerChatHandler()._load_credentials(optional_params)
+
+    assert credentials.access_key == "ASIASMCHATTAGGED"
+    assert aws_region_name == "us-east-1"
+    assert "aws_session_tags" not in optional_params
diff --git a/tests/test_litellm/llms/sagemaker/test_sagemaker_completion_handler.py b/tests/test_litellm/llms/sagemaker/test_sagemaker_completion_handler.py
index 881bac096b1..9a5f36e2081 100644
--- a/tests/test_litellm/llms/sagemaker/test_sagemaker_completion_handler.py
+++ b/tests/test_litellm/llms/sagemaker/test_sagemaker_completion_handler.py
@@ -219,3 +219,51 @@ def test_load_credentials_assumes_role_with_external_id(monkeypatch):
     assert credentials.token == "assumed-session-token"
     assert aws_region_name == "us-east-1"
     assert "aws_external_id" not in optional_params
+
+
+def test_load_credentials_assumes_role_with_session_tags(monkeypatch):
+    """A trust policy gated on sts:TagSession only admits the session when the deployment's tags are sent."""
+    import datetime
+
+    import boto3
+    from botocore.exceptions import ClientError
+    from unittest.mock import patch
+
+    monkeypatch.delenv("AWS_WEB_IDENTITY_TOKEN_FILE", raising=False)
+    monkeypatch.delenv("AWS_ROLE_ARN", raising=False)
+    tags = [{"Key": "team", "Value": "genai"}]
+
+    class FakeSTSClient:
+        def get_caller_identity(self):
+            return {"Arn": "arn:aws:iam::111111111111:user/litellm-proxy-pod"}
+
+        def assume_role(self, **params):
+            if list(params.get("Tags", ())) != tags:
+                raise ClientError(
+                    {"Error": {"Code": "AccessDenied", "Message": "is not authorized to perform: sts:TagSession"}},
+                    "AssumeRole",
+                )
+            return {
+                "Credentials": {
+                    "AccessKeyId": "ASIASMCOMPTAGGED",
+                    "SecretAccessKey": "assumed-secret",
+                    "SessionToken": "assumed-session-token",
+                    "Expiration": datetime.datetime.now(datetime.timezone.utc) + datetime.timedelta(minutes=30),
+                }
+            }
+
+    optional_params = {
+        "aws_access_key_id": "AKIASMCOMPCALLERKEY",
+        "aws_secret_access_key": "pod-caller-secret",
+        "aws_region_name": "us-east-1",
+        "aws_role_name": "arn:aws:iam::999999999999:role/litellm-sm-completion-role",
+        "aws_session_name": "litellm-sm-completion-session",
+        "aws_session_tags": tags,
+    }
+
+    with patch.object(boto3, "client", return_value=FakeSTSClient()):
+        credentials, aws_region_name = SagemakerLLM()._load_credentials(optional_params)
+
+    assert credentials.access_key == "ASIASMCOMPTAGGED"
+    assert aws_region_name == "us-east-1"
+    assert "aws_session_tags" not in optional_params
diff --git a/tests/test_litellm/llms/vertex_ai/audio_transcription/test_vertex_ai_gemini_transcribe_transformation.py b/tests/test_litellm/llms/vertex_ai/audio_transcription/test_vertex_ai_gemini_transcribe_transformation.py
index eadd87d9c92..08e46b1ffac 100644
--- a/tests/test_litellm/llms/vertex_ai/audio_transcription/test_vertex_ai_gemini_transcribe_transformation.py
+++ b/tests/test_litellm/llms/vertex_ai/audio_transcription/test_vertex_ai_gemini_transcribe_transformation.py
@@ -322,8 +322,8 @@ class TestModelCostEntry:
             entry = json.load(f)["vertex_ai/gemini-3.5-transcribe-preview"]
         assert entry["mode"] == "audio_transcription"
         assert entry["litellm_provider"] == "vertex_ai"
-        assert entry["input_cost_per_audio_token"] == pytest.approx(2.5e-06)
-        assert entry["input_cost_per_token"] == pytest.approx(2.5e-06)
+        assert entry["input_cost_per_audio_token"] == pytest.approx(2e-06)
+        assert entry["input_cost_per_token"] == pytest.approx(2e-06)
         assert entry["output_cost_per_token"] == pytest.approx(1.2e-05)
         assert entry["supported_endpoints"] == ["/v1/audio/transcriptions"]
 
diff --git a/tests/test_litellm/llms/voyage/test_voyage_contextual_embedding.py b/tests/test_litellm/llms/voyage/test_voyage_contextual_embedding.py
new file mode 100644
index 00000000000..d3e912ce6af
--- /dev/null
+++ b/tests/test_litellm/llms/voyage/test_voyage_contextual_embedding.py
@@ -0,0 +1,263 @@
+import json
+from unittest.mock import MagicMock
+
+import pytest
+
+
+class TestVoyageContextualEmbeddings:
+    def test_contextual_model_detection(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        assert VoyageContextualEmbeddingConfig.is_contextualized_embeddings("voyage-context-3")
+        assert VoyageContextualEmbeddingConfig.is_contextualized_embeddings("voyage-context-4")
+        assert not VoyageContextualEmbeddingConfig.is_contextualized_embeddings("voyage-3-lite")
+
+    def test_url_generation(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        assert (
+            config.get_complete_url(None, None, "voyage-context-4", {}, {})
+            == "https://api.voyageai.com/v1/contextualizedembeddings"
+        )
+        assert (
+            config.get_complete_url("https://custom.api.com", None, "voyage-context-4", {}, {})
+            == "https://custom.api.com/contextualizedembeddings"
+        )
+        assert (
+            config.get_complete_url(
+                "https://custom.api.com/contextualizedembeddings",
+                None,
+                "voyage-context-4",
+                {},
+                {},
+            )
+            == "https://custom.api.com/contextualizedembeddings"
+        )
+
+    def test_get_supported_openai_params(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        assert config.get_supported_openai_params("voyage-context-4") == [
+            "encoding_format",
+            "dimensions",
+        ]
+
+    def test_map_openai_params(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        result = config.map_openai_params(
+            {"encoding_format": "float", "dimensions": 512}, {}, "voyage-context-4", False
+        )
+        assert result["encoding_format"] == "float"
+        assert result["output_dimension"] == 512
+
+    def test_validate_environment_with_api_key(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        headers = config.validate_environment(
+            {}, "voyage-context-4", [], {}, {}, api_key="test-key"
+        )
+        assert headers == {"Authorization": "Bearer test-key"}
+
+    def test_validate_environment_secret_fallback(self, monkeypatch):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        monkeypatch.setenv("VOYAGE_API_KEY", "secret-key")
+        config = VoyageContextualEmbeddingConfig()
+        headers = config.validate_environment(
+            {}, "voyage-context-4", [], {}, {}, api_key=None
+        )
+        assert headers == {"Authorization": "Bearer secret-key"}
+
+    def test_nested_list_passthrough(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        nested = [["Hello", "world"], ["Test"]]
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", nested, {}, {}
+        )
+        assert transformed["inputs"] == nested
+        assert transformed["model"] == "voyage-context-4"
+        assert "enable_auto_chunking" not in transformed
+
+    def test_flat_list_str_auto_chunked(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", ["Hello", "world"], {}, {}
+        )
+        assert transformed["inputs"] == ["Hello", "world"]
+        assert transformed["enable_auto_chunking"] is True
+        assert transformed["chunk_size"] == 32000
+        assert transformed["input_type"] == "document"
+
+    def test_flat_list_str_query_no_auto_chunk(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", ["Hello", "world"], {"input_type": "query"}, {}
+        )
+        assert transformed["inputs"] == ["Hello", "world"]
+        assert transformed["input_type"] == "query"
+        assert "enable_auto_chunking" not in transformed
+
+    def test_flat_list_str_document_preserves_input_type(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", ["Hello"], {"input_type": "document"}, {}
+        )
+        assert transformed["input_type"] == "document"
+        assert transformed["enable_auto_chunking"] is True
+
+    def test_flat_list_str_caller_chunk_params_win(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4",
+            ["Hello", "world"],
+            {"input_type": "document", "chunk_size": 512, "chunk_overlap": 32},
+            {},
+        )
+        assert transformed["enable_auto_chunking"] is True
+        assert transformed["chunk_size"] == 512
+        assert transformed["chunk_overlap"] == 32
+        assert transformed["input_type"] == "document"
+
+    def test_flat_list_str_caller_can_disable_auto_chunking(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", ["Hello"], {"enable_auto_chunking": False}, {}
+        )
+        assert transformed["enable_auto_chunking"] is False
+        assert transformed["input_type"] == "document"
+
+    def test_nested_list_keeps_caller_params(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", [["Hello", "world"]], {"input_type": "document", "output_dimension": 512}, {}
+        )
+        assert transformed == {
+            "inputs": [["Hello", "world"]],
+            "model": "voyage-context-4",
+            "input_type": "document",
+            "output_dimension": 512,
+        }
+
+    def test_single_string_auto_chunked(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", "Hello", {}, {}
+        )
+        assert transformed["inputs"] == ["Hello"]
+        assert transformed["enable_auto_chunking"] is True
+        assert transformed["input_type"] == "document"
+
+    def test_single_string_query_no_auto_chunk(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+
+        config = VoyageContextualEmbeddingConfig()
+        transformed = config.transform_embedding_request(
+            "voyage-context-4", "Hello", {"input_type": "query"}, {}
+        )
+        assert transformed["inputs"] == ["Hello"]
+        assert transformed["input_type"] == "query"
+        assert "enable_auto_chunking" not in transformed
+
+    def test_response_transformation(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+        )
+        from litellm.types.utils import EmbeddingResponse
+
+        config = VoyageContextualEmbeddingConfig()
+        response_payload = {
+            "object": "list",
+            "data": [{"object": "embedding", "embedding": [0.1, 0.2], "index": 0}],
+            "model": "voyage-context-4",
+            "usage": {"total_tokens": 24},
+        }
+        raw_response = MagicMock()
+        raw_response.json.return_value = response_payload
+        raw_response.status_code = 200
+        raw_response.text = json.dumps(response_payload)
+
+        model_response = EmbeddingResponse()
+        transformed = config.transform_embedding_response(
+            "voyage-context-4", raw_response, model_response, MagicMock()
+        )
+        assert transformed.model == "voyage-context-4"
+        assert transformed.object == "list"
+        assert transformed.data == response_payload["data"]
+        assert transformed.usage.prompt_tokens == 24
+        assert transformed.usage.total_tokens == 24
+
+    def test_error_response_and_error_class(self):
+        from litellm.llms.voyage.embedding.transformation_contextual import (
+            VoyageContextualEmbeddingConfig,
+            VoyageError,
+        )
+        from litellm.types.utils import EmbeddingResponse
+
+        config = VoyageContextualEmbeddingConfig()
+        raw_response = MagicMock()
+        raw_response.json.side_effect = ValueError("not json")
+        raw_response.status_code = 400
+        raw_response.text = "bad request"
+
+        with pytest.raises(VoyageError) as exc_info:
+            config.transform_embedding_response(
+                "voyage-context-4", raw_response, EmbeddingResponse(), MagicMock()
+            )
+        assert exc_info.value.status_code == 400
+        assert exc_info.value.message == "bad request"
+
+        error = config.get_error_class("rate limited", 429, {"x-test": "1"})
+        assert isinstance(error, VoyageError)
+        assert error.status_code == 429
+        assert error.message == "rate limited"
diff --git a/tests/test_litellm/llms/wandb/test_wandb_chat_transformation.py b/tests/test_litellm/llms/wandb/test_wandb_chat_transformation.py
index a5d1eccebe0..dd0d1bdbb9d 100644
--- a/tests/test_litellm/llms/wandb/test_wandb_chat_transformation.py
+++ b/tests/test_litellm/llms/wandb/test_wandb_chat_transformation.py
@@ -5,18 +5,92 @@ These tests validate the WandbInferenceConfig class which extends OpenAIGPTConfi
 Nebius AI Studio is an OpenAI-compatible provider with minor customizations.
 """
 
-
+import json
+from typing import Final
 
 import pytest
+import respx
 
 import litellm
 from litellm import completion
 from litellm.llms.wandb.chat.transformation import WandbConfig
 
 
+WANDB_REASONING_MODELS: Final = (
+    "deepseek-ai/DeepSeek-V4-Flash",
+    "deepseek-ai/DeepSeek-V4-Flash-0731",
+    "deepseek-ai/DeepSeek-V4-Pro",
+    "deepseek-ai/DeepSeek-V4-Pro-0813",
+    "deepseek-ai/DeepSeek-V3.1",
+    "google/gemma-4-31B-it",
+    "ibm-granite/granite-4.2-8b",
+    "MiniMaxAI/MiniMax-M3",
+    "moonshotai/Kimi-K2.7-Code",
+    "moonshotai/Kimi-K2.6",
+    "nvidia/NVIDIA-Nemotron-3.5-Lightning-30B-A3B",
+    "nvidia/NVIDIA-Nemotron-3-Ultra-550B-A55B",
+    "openai/gpt-oss-120b",
+    "openai/gpt-oss-20b",
+    "Qwen/Qwen3.8-27B",
+    "Qwen/Qwen3.6-35B-A3B",
+    "Qwen/Qwen3.6-27B",
+    "Qwen/Qwen3.5-35B-A3B",
+    "zai-org/GLM-5.2",
+    "moonshotai/Kimi-K2.5",
+    "MiniMaxAI/MiniMax-M2.5",
+    "zai-org/GLM-4.5",
+    "Qwen/Qwen3-235B-A22B-Thinking-2507",
+    "deepseek-ai/DeepSeek-R1-0528",
+)
+
+
+@pytest.fixture
+def wandb_test_config(local_model_cost_map, monkeypatch: pytest.MonkeyPatch) -> None:
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    monkeypatch.setattr(litellm, "telemetry", False)
+    monkeypatch.setattr(litellm, "drop_params", False)
+
+
+@pytest.fixture
+def wandb_request_mock(respx_mock: respx.MockRouter) -> respx.Route:
+    return respx_mock.post("https://api.inference.wandb.ai/v1/chat/completions").respond(
+        json={
+            "id": "chatcmpl-123",
+            "object": "chat.completion",
+            "created": 1677652288,
+            "model": "test-model",
+            "choices": [
+                {
+                    "index": 0,
+                    "message": {"role": "assistant", "content": "Done"},
+                    "finish_reason": "stop",
+                }
+            ],
+            "usage": {"prompt_tokens": 1, "completion_tokens": 1, "total_tokens": 2},
+        },
+        status_code=200,
+    )
+
+
 class TestWandbConfig:
     """Test class for WandB Inference functionality"""
 
+    @pytest.mark.parametrize("model", WANDB_REASONING_MODELS)
+    def test_map_openai_params_preserves_reasoning_effort(self, wandb_test_config, model: str):
+        assert litellm.model_cost[f"wandb/{model}"].get("supports_reasoning") is True
+        supported_params = litellm.get_supported_openai_params(model=f"wandb/{model}")
+        assert supported_params is not None
+        assert "reasoning_effort" in supported_params
+
+        result = WandbConfig().map_openai_params(
+            non_default_params={"reasoning_effort": "medium", "max_completion_tokens": 64},
+            optional_params={},
+            model=model,
+            drop_params=True,
+        )
+
+        assert result == {"reasoning_effort": "medium", "max_tokens": 64}
+
     def test_default_api_base(self):
         """Test that default API base is used when none is provided"""
         config = WandbConfig()
@@ -139,3 +213,104 @@ class TestWandbConfig:
             # Check for specific content in the response
             assert "```python" in content
             assert "Hey from LiteLLM" in content
+
+    @pytest.mark.respx()
+    @pytest.mark.parametrize(
+        "model,effort",
+        tuple((model, "medium") for model in WANDB_REASONING_MODELS)
+        + (
+            ("Qwen/Qwen3.8-27B", "low"),
+            ("Qwen/Qwen3.8-27B", "xhigh"),
+        ),
+    )
+    def test_wandb_completion_preserves_reasoning_effort_with_drop_params(
+        self, wandb_test_config, wandb_request_mock: respx.Route, model: str, effort: str
+    ):
+        completion(
+            model=f"wandb/{model}",
+            messages=[{"role": "user", "content": "Hello"}],
+            api_key="fake-wandb-key",
+            api_base="https://api.inference.wandb.ai/v1",
+            reasoning_effort=effort,
+            max_completion_tokens=64,
+            drop_params=True,
+        )
+
+        assert wandb_request_mock.call_count == 1
+        request_body = json.loads(wandb_request_mock.calls[0].request.content)
+        assert request_body["model"] == model
+        assert request_body["reasoning_effort"] == effort
+        assert request_body["max_tokens"] == 64
+        assert "max_completion_tokens" not in request_body
+
+    @pytest.mark.respx(assert_all_called=False)
+    @pytest.mark.parametrize("drop_params", [True, False])
+    @pytest.mark.parametrize(
+        "model,explicit_false",
+        [
+            ("meta-llama/Llama-3.1-8B-Instruct", False),
+            ("openai/gpt-oss-20b", True),
+        ],
+    )
+    def test_wandb_completion_without_reasoning_support(
+        self,
+        wandb_test_config,
+        wandb_request_mock: respx.Route,
+        respx_mock: respx.MockRouter,
+        monkeypatch: pytest.MonkeyPatch,
+        model: str,
+        explicit_false: bool,
+        drop_params: bool,
+    ):
+        with monkeypatch.context() as context:
+            if explicit_false:
+                context.setitem(litellm.model_cost[f"wandb/{model}"], "supports_reasoning", False)
+
+            kwargs = {
+                "model": f"wandb/{model}",
+                "messages": [{"role": "user", "content": "Hello"}],
+                "api_key": "fake-wandb-key",
+                "api_base": "https://api.inference.wandb.ai/v1",
+                "reasoning_effort": "medium",
+                "drop_params": drop_params,
+            }
+            if not drop_params:
+                with pytest.raises(litellm.UnsupportedParamsError, match="reasoning_effort"):
+                    completion(**kwargs)
+                assert len(respx_mock.calls) == 0
+                return
+
+            completion(**kwargs)
+            assert wandb_request_mock.call_count == 1
+            request_body = json.loads(wandb_request_mock.calls[0].request.content)
+            assert request_body["model"] == model
+            assert "reasoning_effort" not in request_body
+
+            supported_params = litellm.get_supported_openai_params(model=f"wandb/{model}")
+            assert supported_params is not None
+            assert "reasoning_effort" not in supported_params
+
+    @pytest.mark.respx()
+    def test_wandb_completion_keeps_reasoning_effort_for_an_unregistered_model(
+        self, wandb_test_config, wandb_request_mock: respx.Route
+    ):
+        """A wandb id the registry has not named yet resolves through the
+        wandb-reasoning-baseline fallback generalization, so its reasoning_effort reaches
+        the provider instead of raising. W&B adds reasoning models faster than this
+        registry names them, and an exact entry still wins wherever one exists."""
+        model: Final = "zai-org/GLM-6-Turbo"
+        assert f"wandb/{model}" not in litellm.model_cost
+
+        completion(
+            model=f"wandb/{model}",
+            messages=[{"role": "user", "content": "Hello"}],
+            api_key="fake-wandb-key",
+            api_base="https://api.inference.wandb.ai/v1",
+            reasoning_effort="medium",
+            drop_params=False,
+        )
+
+        assert wandb_request_mock.call_count == 1
+        request_body = json.loads(wandb_request_mock.calls[0].request.content)
+        assert request_body["model"] == model
+        assert request_body["reasoning_effort"] == "medium"
diff --git a/tests/test_litellm/passthrough/test_passthrough_main.py b/tests/test_litellm/passthrough/test_passthrough_main.py
index 1950c37a12e..546cff18b5d 100644
--- a/tests/test_litellm/passthrough/test_passthrough_main.py
+++ b/tests/test_litellm/passthrough/test_passthrough_main.py
@@ -873,3 +873,118 @@ def test_llm_passthrough_route_propagates_allm_passthrough_route_to_logging_obj(
 
     assert captured_litellm_params.get("allm_passthrough_route") is True
     assert LitellmLogging._is_sync_litellm_request(captured_litellm_params) is False
+
+
+FOUNDRY_BASE = "https://my-resource.services.ai.azure.com"
+
+
+def _foundry_parse_response() -> httpx.Response:
+    return httpx.Response(
+        status_code=200,
+        headers={"content-type": "application/json"},
+        content=b'{"id":"parse-1","pages":[]}',
+        request=httpx.Request("POST", f"{FOUNDRY_BASE}/providers/cohere/v2/parse"),
+    )
+
+
+def test_azure_ai_relay_reaches_the_deployment_with_its_own_credential():
+    """
+    Regression for LIT-7022: azure_ai had no passthrough config, so every
+    /azure_ai/<router-model>/<native-path> relay raised "Provider azure_ai not found"
+    before a request was built.
+    """
+    client = HTTPHandler()
+
+    with patch.object(client.client, "send", return_value=_foundry_parse_response()) as mock_send:
+        response = llm_passthrough_route(
+            model="azure_ai/Cohere-parse-v5",
+            endpoint="Cohere-parse-v5/providers/cohere/v2/parse",
+            method="POST",
+            custom_llm_provider="azure_ai",
+            api_base=FOUNDRY_BASE,
+            api_key="deployment-key",
+            json={"model": "Cohere-parse-v5", "document": {"type": "image_url", "image_url": "https://x/y.png"}},
+            client=client,
+            litellm_logging_obj=MagicMock(),
+        )
+
+    sent = mock_send.call_args.kwargs["request"]
+    assert str(sent.url) == f"{FOUNDRY_BASE}/providers/cohere/v2/parse"
+    assert sent.headers["api-key"] == "deployment-key"
+    assert json.loads(sent.content)["model"] == "Cohere-parse-v5"
+    assert response.status_code == 200
+
+
+@pytest.mark.asyncio
+async def test_router_relays_azure_ai_model_through_the_deployment_api_base():
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "foundry-parse",
+                "litellm_params": {
+                    "model": "azure_ai/Cohere-parse-v5",
+                    "api_base": FOUNDRY_BASE,
+                    "api_key": "deployment-key",
+                },
+            }
+        ]
+    )
+    async_client = AsyncHTTPHandler()
+
+    with patch.object(async_client.client, "send", AsyncMock(return_value=_foundry_parse_response())) as mock_send:
+        response = await router.allm_passthrough_route(
+            model="foundry-parse",
+            method="POST",
+            endpoint="foundry-parse/providers/cohere/v2/parse",
+            json={"model": "foundry-parse", "document": {"type": "image_url", "image_url": "https://x/y.png"}},
+            client=async_client,
+        )
+
+    sent = mock_send.call_args.kwargs["request"]
+    assert str(sent.url) == f"{FOUNDRY_BASE}/providers/cohere/v2/parse"
+    assert sent.headers["api-key"] == "deployment-key"
+    assert json.loads(sent.content)["model"] == "Cohere-parse-v5"
+    assert response.status_code == 200
+
+
+@pytest.mark.asyncio
+async def test_router_relays_an_openai_model_on_a_foundry_base_as_azure_ai(monkeypatch):
+    monkeypatch.setenv("AZURE_AI_API_BASE", "https://unrelated.openai.azure.com")
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "foundry-gpt",
+                "litellm_params": {
+                    "model": "azure_ai/gpt-5.4-mini",
+                    "api_base": FOUNDRY_BASE,
+                    "api_key": "deployment-key",
+                },
+            }
+        ]
+    )
+    async_client = AsyncHTTPHandler()
+    upstream = httpx.Response(
+        status_code=200,
+        headers={"content-type": "application/json"},
+        content=(
+            b'{"id":"chatcmpl-1","object":"chat.completion","model":"gpt-5.4-mini",'
+            b'"choices":[{"index":0,"finish_reason":"stop","message":{"role":"assistant","content":"hi"}}],'
+            b'"usage":{"prompt_tokens":1,"completion_tokens":1,"total_tokens":2}}'
+        ),
+        request=httpx.Request("POST", f"{FOUNDRY_BASE}/models/chat/completions"),
+    )
+
+    with patch.object(async_client.client, "send", AsyncMock(return_value=upstream)) as mock_send:
+        await router.allm_passthrough_route(
+            model="foundry-gpt",
+            method="POST",
+            endpoint="foundry-gpt/models/chat/completions",
+            request_query_params={"api-version": "2024-05-01-preview"},
+            json={"model": "foundry-gpt", "messages": [{"role": "user", "content": "hi"}]},
+            client=async_client,
+        )
+
+    sent = mock_send.call_args.kwargs["request"]
+    assert str(sent.url) == f"{FOUNDRY_BASE}/models/chat/completions?api-version=2024-05-01-preview"
+    assert sent.headers["api-key"] == "deployment-key"
+    assert json.loads(sent.content)["model"] == "gpt-5.4-mini"
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/auth/test_user_api_key_auth_mcp.py b/tests/test_litellm/proxy/_experimental/mcp_server/auth/test_user_api_key_auth_mcp.py
index 20f4719e4bf..e6c8d4ee039 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/auth/test_user_api_key_auth_mcp.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/auth/test_user_api_key_auth_mcp.py
@@ -7193,14 +7193,13 @@ class TestAggregateGatewayDcrChallenge:
         www_authenticate = (exc_info.value.headers or {})["WWW-Authenticate"]
         assert www_authenticate == f"Bearer {self._EXPECTED_RESOURCE_METADATA}"
 
-    async def test_per_server_challenge_for_gateway_managed_oauth2(self):
-        """Anonymous request to a per-server path whose single target is a gateway-managed
-        oauth2 server: 401 plus the RFC 9728 challenge advertising the PER-SERVER
-        protected-resource metadata in the same URL spelling the request used, so a keyless
-        DCR client configured with either per-server spelling discovers the gateway as the
-        authorization server (LIT-4864). Covers interactive and M2M, which the gateway can
-        both serve end to end."""
-        from litellm.types.mcp import MCPAuth
+    @pytest.mark.parametrize(
+        "auth_type",
+        (None, "none", "api_key", "bearer_token", "basic", "aws_sigv4", "authorization", "token", "oauth2"),
+    )
+    @pytest.mark.parametrize("bearer_presented", (False, True))
+    async def test_per_server_challenge_for_gateway_owned_auth(self, auth_type, bearer_presented):
+        """Gateway admission challenges are independent of upstream authentication."""
         from litellm.types.mcp_server.mcp_server_manager import MCPServer
 
         server = MCPServer(
@@ -7209,7 +7208,7 @@ class TestAggregateGatewayDcrChallenge:
             server_name="github",
             url="https://upstream.example/mcp",
             transport="http",
-            auth_type=MCPAuth.oauth2,
+            auth_type=auth_type,
         )
         for path, expected_metadata_path in (
             ("/mcp/github", "/.well-known/oauth-protected-resource/mcp/github"),
@@ -7223,10 +7222,16 @@ class TestAggregateGatewayDcrChallenge:
             ):
                 mock_mgr.get_mcp_server_by_name.return_value = server
                 with pytest.raises(HTTPException) as exc_info:
-                    await MCPRequestHandler.process_mcp_request(self._scope(path=path))
+                    await MCPRequestHandler.process_mcp_request(
+                        self._scope(
+                            path=path,
+                            extra_headers=((b"authorization", b"Bearer invalid-key"),) if bearer_presented else (),
+                        )
+                    )
             assert exc_info.value.status_code == 401
             www_authenticate = (exc_info.value.headers or {})["WWW-Authenticate"]
-            assert www_authenticate == f'Bearer resource_metadata="http://testserver{expected_metadata_path}"'
+            error = 'error="invalid_token", ' if bearer_presented else ""
+            assert www_authenticate == f'Bearer {error}resource_metadata="http://testserver{expected_metadata_path}"'
 
     async def test_per_server_challenge_keeps_spelling_under_server_root_path(self):
         """On a sub-path deployment the challenge must still advertise the spelling the client
@@ -7303,10 +7308,7 @@ class TestAggregateGatewayDcrChallenge:
                     )
 
     def test_challenge_target_excludes_every_non_gateway_managed_mode(self):
-        """Unit pin of the challenge-target owner: only a resolved gateway-managed oauth2
-        target (interactive or M2M) yields a per-server challenge; delegate-auth oauth2
-        (whose keyless flow is upstream PKCE via the relay), every client-forwarded auth
-        type, OBO, api_key, unknown names, and CSV paths yield None (LIT-4864)."""
+        """Gateway challenges exclude unresolved, delegated, and client-forwarded targets."""
         from litellm.proxy._experimental.mcp_server.auth.user_api_key_auth_mcp import (
             _gateway_dcr_challenge_target,
         )
@@ -7333,7 +7335,11 @@ class TestAggregateGatewayDcrChallenge:
             (_server(MCPAuth.true_passthrough), None),
             (_server(MCPAuth.oauth_delegate), None),
             (_server(MCPAuth.oauth_delegate, dcr_bridge=True), None),
-            (_server(MCPAuth.api_key), None),
+            (_server(MCPAuth.api_key), "srv"),
+            (_server(MCPAuth.none, extra_headers=["Authorization"]), None),
+            (_server(None, extra_headers=["X-API-Key"]), None),
+            (_server(MCPAuth.none, extra_headers=["Authorization"], oauth_passthrough=True), None),
+            (_server(MCPAuth.oauth2_id_jag), None),
             (None, None),
         ]
         for resolved, expected in cases:
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_authz_code_refresher.py b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_authz_code_refresher.py
index bb2f2ff8b02..df068b60338 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_authz_code_refresher.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_authz_code_refresher.py
@@ -22,6 +22,7 @@ class _Server:
         server_id="srv",
         configured_token_url=None,
     ):
+        self.oauth_identity_binding = None
         self.token_url = token_url
         self.configured_token_url = configured_token_url
         self.client_id = client_id
@@ -287,3 +288,40 @@ async def test_refresh_uses_admin_entered_token_url_when_issuer_yield_empties_re
     assert token is not None
     assert token.access_token == "new-at"
     assert posted[0][0] == "https://idp.example.com/token"
+
+
+@pytest.mark.asyncio
+async def test_identity_rejection_never_persists_or_returns_refreshed_token():
+    from unittest.mock import AsyncMock
+
+    from fastapi import HTTPException
+
+    validator = AsyncMock(side_effect=HTTPException(status_code=403, detail="oauth_principal_mismatch"))
+    persist = AsyncMock()
+    refresher = AuthorizationCodeRefresher(
+        _lookup(_Server()),
+        _endpoint({"access_token": "foreign-token", "id_token": "foreign-identity"}),
+        persist,
+        identity_validator=validator,
+    )
+    assert await refresher.refresh("alice", "srv", OAuthToken(access_token="old", refresh_token="old-rt")) is None
+    persist.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_verified_refresh_preserves_binding_proof_in_storage():
+    from unittest.mock import AsyncMock
+
+    validator = AsyncMock(return_value="verified-binding")
+    persist = AsyncMock()
+    refresher = AuthorizationCodeRefresher(
+        _lookup(_Server()),
+        _endpoint({"access_token": "new", "refresh_token": "rotated"}),
+        persist,
+        identity_validator=validator,
+    )
+    token = await refresher.refresh("alice", "srv", OAuthToken(access_token="old", refresh_token="old-rt"))
+    assert token.access_token == "new"
+    assert token.refresh_token == "rotated"
+    assert token.identity_binding_proof == "verified-binding"
+    assert persist.await_args.kwargs["identity_binding_proof"] == "verified-binding"
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_per_user_oauth_store.py b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_per_user_oauth_store.py
index ca32cf2bb8d..e7308884060 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_per_user_oauth_store.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_per_user_oauth_store.py
@@ -246,3 +246,94 @@ async def test_lazy_store_invalidate_works_after_redis_chain_is_built() -> None:
 
     assert build_calls == 1
     assert redis_store.invalidations == [("u", "s")]
+
+
+@pytest.mark.asyncio
+async def test_enforcement_invalidates_cached_legacy_credentials_before_use():
+    from litellm.types.mcp import MCPAuth, MCPTransport
+    from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+    server = MCPServer(
+        server_id="srv",
+        name="srv",
+        transport=MCPTransport.http,
+        auth_type=MCPAuth.oauth2,
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode="enforce",
+            issuer="https://idp.example.com",
+            audiences=["client"],
+        ),
+    )
+    cached = _RecordingStore("belongs-to-bob")
+
+    store = LazyPerUserOAuthTokenStore(
+        lambda server_id: server,
+        store_builder=lambda lookup: (cached, False),
+        redis_available=lambda: False,
+    )
+    assert await store.fetch("alice", "srv") is None
+    assert cached.calls == [("alice", "srv")]
+    assert cached.invalidations == [("alice", "srv")]
+
+
+@pytest.mark.asyncio
+async def test_enforced_cache_hit_avoids_credential_read_and_rejects_changed_policy(monkeypatch):
+    from unittest.mock import AsyncMock
+
+    from litellm.proxy._experimental.mcp_server.oauth_identity_binding import current_binding_proof
+    from litellm.proxy._experimental.mcp_server.outbound_credentials import per_user_oauth_store as module
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    server = MCPServer(
+        server_id="srv",
+        name="srv",
+        transport="http",
+        auth_type="oauth2",
+        oauth_identity_binding={
+            "mode": "enforce",
+            "issuer": "https://idp.example",
+            "audiences": ["client"],
+            "caller_field": "user_id",
+            "principal_claim": "sub",
+        },
+    )
+    proof = await current_binding_proof(server.oauth_identity_binding, "alice", "srv")
+    read = AsyncMock(return_value={"access_token": "alice-token", "identity_binding_proof": proof})
+    monkeypatch.setattr(module, "_read_credential", read)
+    monkeypatch.setattr(module, "_runtime_backend_and_coordinator", lambda: (None, None, False))
+    store = LazyPerUserOAuthTokenStore(lambda _: server, redis_available=lambda: False)
+    assert (await store.fetch("alice", "srv")).access_token == "alice-token"
+    assert (await store.fetch("alice", "srv")).access_token == "alice-token"
+    read.assert_awaited_once_with("alice", "srv")
+    server.oauth_identity_binding = server.oauth_identity_binding.model_copy(update={"audiences": ["changed"]})
+    assert await store.fetch("alice", "srv") is None
+    read.assert_awaited_once()
+    assert await store.fetch("alice", "srv") is None
+    assert read.await_count == 2
+
+
+@pytest.mark.asyncio
+async def test_expired_unverified_credential_never_reaches_refresh(monkeypatch):
+    from unittest.mock import AsyncMock
+
+    from litellm.proxy._experimental.mcp_server.outbound_credentials import per_user_oauth_store as module
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    server = MCPServer(
+        server_id="srv",
+        name="srv",
+        transport="http",
+        auth_type="oauth2",
+        token_url="https://idp.example/token",
+        oauth_identity_binding={"mode": "enforce", "issuer": "https://idp.example", "audiences": ["client"]},
+    )
+    read = AsyncMock(
+        return_value={"access_token": "bob", "refresh_token": "bob-refresh", "expires_at": "2000-01-01T00:00:00Z"}
+    )
+    post = AsyncMock()
+    monkeypatch.setattr(module, "_read_credential", read)
+    monkeypatch.setattr(module, "_post_token_endpoint", post)
+    monkeypatch.setattr(module, "_runtime_backend_and_coordinator", lambda: (None, None, False))
+    store = LazyPerUserOAuthTokenStore(lambda _: server, redis_available=lambda: False)
+    assert await store.fetch("alice", "srv") is None
+    post.assert_not_awaited()
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_resolver.py b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_resolver.py
index 6b3098d9e60..5fab4ceec72 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_resolver.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_resolver.py
@@ -19,6 +19,7 @@ from pydantic import SecretStr
 
 from litellm.proxy._experimental.mcp_server.outbound_credentials import (
     ApiKeyConfig,
+    AuthConfig,
     AuthorizationCodeConfig,
     AwsSigV4Config,
     Byok,
@@ -1203,3 +1204,71 @@ async def test_passthrough_ignores_the_carrier_and_keeps_the_callers_slot():
     assert isinstance(result, Ok)
     headers, _ = await _emitted_async(result.ok)
     assert headers["Authorization"] == "caller-token"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("config", "subject", "expected_source", "expected_header"),
+    [
+        (NoneConfig(), _SUBJECT, "no-auth", None),
+        (PassthroughConfig(), _SUBJECT, "no-auth", None),
+        (PassthroughConfig(), _with_inbound("Bearer caller-token"), "oauth2-passthrough", "Bearer caller-token"),
+        (ApiKeyConfig(key_source=SharedKey(value=SecretStr("static-key"))), _SUBJECT, "static-token", "Bearer static-key"),
+        (AuthorizationCodeConfig(), Subject(tenant_id="", subject_id="alice"), "stored-user-token", "Bearer stored-alice"),
+    ],
+)
+async def test_resolved_source_matches_the_credential_sent_upstream(
+    config: AuthConfig, subject: Subject, expected_source: str, expected_header: str | None
+) -> None:
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.resolver import resolve_credentials_with_source
+
+    store = _FakeTokenStore({("alice", "s"): OAuthToken(access_token="stored-alice")})
+    provider = UpstreamCredentialProvider(oauth_token_store=store)
+    result = await resolve_credentials_with_source(provider, subject, _spec(config))
+    assert isinstance(result, Ok)
+    assert result.ok.source.value == expected_source
+    assert _emitted(result.ok.auth).get("Authorization") == expected_header
+    assert "stored-alice" not in repr(result.ok)
+    assert "static-key" not in repr(result.ok)
+
+
+@pytest.mark.asyncio
+async def test_resolved_source_preserves_missing_user_token_error() -> None:
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.resolver import resolve_credentials_with_source
+
+    result = await resolve_credentials_with_source(UpstreamCredentialProvider(), _SUBJECT, _spec(AuthorizationCodeConfig()))
+    assert isinstance(result, Error)
+    assert result.error.tag == "unauthorized"
+
+
+@pytest.mark.asyncio
+async def test_minted_token_sources_match_egress_and_do_not_fetch_twice() -> None:
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.resolver import resolve_credentials_with_source
+
+    source = _FakeM2MSource(Ok(OAuthToken(access_token="m2m-at")))
+    m2m = await resolve_credentials_with_source(UpstreamCredentialProvider(client_credentials_source=source), _SUBJECT, _spec(_M2M))
+    assert isinstance(m2m, Ok)
+    headers, _ = await _emitted_async(m2m.ok.auth)
+    assert headers["Authorization"] == "Bearer m2m-at"
+    assert m2m.ok.source.value == "m2m-client-credentials"
+    assert source.gets == ["s"]
+
+    exchanger = _FakeExchanger(Ok(OAuthToken(access_token="exchanged-at")))
+    exchanged = await resolve_credentials_with_source(UpstreamCredentialProvider(token_exchanger=exchanger), _with_inbound("subject"), _spec(_OBO))
+    assert isinstance(exchanged, Ok)
+    assert _emitted(exchanged.ok.auth)["Authorization"] == "Bearer exchanged-at"
+    assert exchanged.ok.source.value == "token-exchange"
+    assert len(exchanger.calls) == 1
+
+
+@pytest.mark.asyncio
+async def test_id_jag_source_describes_final_token_after_both_exchanges() -> None:
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.resolver import resolve_credentials_with_source
+
+    endpoint = _FakeTokenEndpoint(_two_leg_ok("resource-token"))
+    provider = UpstreamCredentialProvider(token_endpoint=endpoint)
+    result = await resolve_credentials_with_source(provider, _with_inbound("identity-token"), _spec(_id_jag_config()))
+    assert isinstance(result, Ok)
+    assert result.ok.source.value == "id-jag"
+    assert _emitted(result.ok.auth)["Authorization"] == "Bearer resource-token"
+    assert len(endpoint.calls) == 2
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_token_cache_codec.py b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_token_cache_codec.py
index 17a7e13af03..12a04c4b4dc 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_token_cache_codec.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/outbound_credentials/test_token_cache_codec.py
@@ -52,3 +52,17 @@ def test_undecryptable_blob_is_a_miss():
 def test_empty_plaintext_is_a_miss():
     codec = OAuthTokenCacheCodec(encrypt=lambda s: s, decrypt=lambda b: b)
     assert codec.decode("") is None
+
+
+def test_bound_token_round_trip_preserves_proof_without_refresh_secret():
+    codec = _wrapping_codec()
+    blob = codec.encode(OAuthToken("alice-token", refresh_token="private-refresh", identity_binding_proof="proof"))
+    assert "private-refresh" not in blob
+    decoded = codec.decode(blob)
+    assert decoded == OAuthToken("alice-token", identity_binding_proof="proof")
+
+
+def test_malformed_bound_entries_fail_closed():
+    codec = _wrapping_codec()
+    for payload in ("not-json", "{}", '{"access_token":"at"}', '{"access_token":1,"identity_binding_proof":"p"}'):
+        assert codec.decode("enc:litellm-bound-oauth-v1:" + payload) is None
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_db_credentials.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_db_credentials.py
index 355b3bfd30e..60a5e1a22bb 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_db_credentials.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_db_credentials.py
@@ -628,6 +628,7 @@ async def test_oauth_round_trip_returns_payload():
         access_token,
         refresh_token="rfr-xyz",
         scopes=["a", "b"],
+        identity_binding_proof="verified-proof",
     )
 
     stored = _stored_value(prisma)
@@ -642,6 +643,7 @@ async def test_oauth_round_trip_returns_payload():
     assert result["access_token"] == access_token
     assert result["refresh_token"] == "rfr-xyz"
     assert result["scopes"] == ["a", "b"]
+    assert result["identity_binding_proof"] == "verified-proof"
 
 
 @pytest.mark.asyncio
@@ -1184,6 +1186,7 @@ class _RefreshResponse:
 
 def _refresh_server(**overrides):
     base = dict(
+        oauth_identity_binding=None,
         token_url="https://idp.example.com/token",
         server_id="srv-1",
         client_id="cid",
@@ -1309,7 +1312,7 @@ async def test_refresh_user_oauth_token_uses_client_secret_basic(monkeypatch):
     sends HTTP Basic and keeps the secret out of the body."""
     import litellm.proxy._experimental.mcp_server.db as db_mod
 
-    server = MagicMock()
+    server = MagicMock(oauth_identity_binding=None)
     server.token_url = "https://idp.example.com/oauth2/token"
     server.server_id = "srv"
     server.client_id = "cid"
@@ -1348,7 +1351,7 @@ async def test_refresh_user_oauth_token_defaults_to_client_secret_post(monkeypat
     the body (client_secret_post) and sends no Authorization header."""
     import litellm.proxy._experimental.mcp_server.db as db_mod
 
-    server = MagicMock()
+    server = MagicMock(oauth_identity_binding=None)
     server.token_url = "https://idp.example.com/oauth2/token"
     server.server_id = "srv"
     server.client_id = "cid"
@@ -1609,3 +1612,95 @@ def test_partial_update_defers_omitted_eligibility_fields_to_the_stored_row():
     request = UpdateMCPServerRequest(server_id="relay-update", per_server_oauth_discovery=True)
 
     assert request.per_server_oauth_discovery is True
+
+
+@pytest.mark.asyncio
+async def test_enforcement_rejects_preexisting_unverified_credential():
+    from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+    server = MCPServer(
+        server_id="srv-1", name="srv-1", url="https://mcp.example.com", transport=MCPTransport.http, auth_type=MCPAuth.oauth2,
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode="enforce", issuer="https://idp.example.com", audiences=["client"],
+        ),
+    )
+    result = await resolve_valid_user_oauth_token(
+        user_id="alice", server=server,
+        cred={"access_token": "belongs-to-bob", "refresh_token": "bobs-refresh-token"},
+    )
+    assert result is None
+
+
+@pytest.mark.asyncio
+async def test_refresh_identity_rejection_returns_reauthentication_without_persisting(monkeypatch):
+    from fastapi import HTTPException
+    from litellm.proxy._experimental.mcp_server import db as module
+
+    validator = AsyncMock(side_effect=HTTPException(status_code=403, detail="oauth_principal_mismatch"))
+    monkeypatch.setattr(module, "enforce_oauth_identity_binding", validator)
+    result, captured = await _run_refresh(
+        monkeypatch, _refresh_server(), {"access_token": "bob", "refresh_token": "rotated"}
+    )
+    assert result is None
+    assert captured["data"]["grant_type"] == "refresh_token"
+    module.store_user_oauth_credential.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_verified_legacy_cache_reads_avoid_database_and_reject_policy_changes(monkeypatch):
+    from litellm.caching.caching import DualCache
+    from litellm.proxy import proxy_server
+    from litellm.proxy._experimental.mcp_server import db as module
+    from litellm.proxy._experimental.mcp_server.oauth2_token_cache import mcp_per_user_token_cache
+    from litellm.proxy._experimental.mcp_server.oauth_identity_binding import current_binding_proof
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    server = MCPServer(
+        server_id="srv",
+        name="srv",
+        transport="http",
+        auth_type="oauth2",
+        oauth_identity_binding={
+            "mode": "enforce",
+            "issuer": "https://idp.example",
+            "audiences": ["client"],
+            "caller_field": "user_id",
+            "principal_claim": "sub",
+        },
+    )
+    proof = await current_binding_proof(server.oauth_identity_binding, "alice", "srv")
+    monkeypatch.setattr(proxy_server, "user_api_key_cache", DualCache())
+    read = AsyncMock(return_value=None)
+    monkeypatch.setattr(module, "get_user_oauth_credential", read)
+    monkeypatch.setattr(proxy_server, "prisma_client", MagicMock())
+    await mcp_per_user_token_cache.set("alice", "srv", "alice-token", 60, identity_binding_proof=proof)
+    assert await module.resolve_user_oauth_access_token("alice", server) == "alice-token"
+    assert await module.resolve_user_oauth_access_token("alice", server) == "alice-token"
+    read.assert_not_awaited()
+    server.oauth_identity_binding = server.oauth_identity_binding.model_copy(update={"audiences": ["changed"]})
+    assert await module.resolve_user_oauth_access_token("alice", server) is None
+    read.assert_awaited_once()
+    assert await mcp_per_user_token_cache.get_token("alice", "srv") is None
+
+
+@pytest.mark.asyncio
+async def test_unverified_legacy_cache_cannot_bypass_enforcement(monkeypatch):
+    from litellm.caching.caching import DualCache
+    from litellm.proxy import proxy_server
+    from litellm.proxy._experimental.mcp_server import db as module
+    from litellm.proxy._experimental.mcp_server.oauth2_token_cache import mcp_per_user_token_cache
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    server = MCPServer(
+        server_id="srv",
+        name="srv",
+        transport="http",
+        auth_type="oauth2",
+        oauth_identity_binding={"mode": "enforce", "issuer": "https://idp.example", "audiences": ["client"]},
+    )
+    monkeypatch.setattr(proxy_server, "user_api_key_cache", DualCache())
+    monkeypatch.setattr(proxy_server, "prisma_client", MagicMock())
+    monkeypatch.setattr(module, "get_user_oauth_credential", AsyncMock(return_value={"access_token": "bob"}))
+    await mcp_per_user_token_cache.set("alice", "srv", "bob", 60)
+    assert await module.resolve_user_oauth_access_token("alice", server) is None
+    assert await mcp_per_user_token_cache.get("alice", "srv") is None
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_discoverable_endpoints.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_discoverable_endpoints.py
index 763200c3709..5a99139a67f 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_discoverable_endpoints.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_discoverable_endpoints.py
@@ -7651,12 +7651,6 @@ async def test_token_endpoint_client_secret_basic_without_secret_returns_400():
     assert exc_info.value.status_code == 400
 
 
-# -------------------------------------------------------------------
-# Non-oauth2 (auth_type=none, access-group gated) servers must not be
-# driven through the gateway OAuth authorize/token/register/discovery
-# flow, and must not be advertised as OAuth-protected in discovery docs.
-# -------------------------------------------------------------------
-
 
 def _access_group_none_server(server_name="access_group_server"):
     """A non-oauth2, access-group gated MCP server: no client_id, no OAuth."""
@@ -7794,35 +7788,38 @@ async def test_register_client_rejects_non_oauth2_server():
 
 
 @pytest.mark.asyncio
-async def test_oauth_protected_resource_404_for_non_oauth2_server():
-    """Discovery must not advertise a none-auth server as an OAuth-protected resource."""
-    try:
-        from litellm.proxy._experimental.mcp_server.discoverable_endpoints import (
-            _build_oauth_protected_resource_response,
-        )
-        from litellm.proxy._experimental.mcp_server.mcp_server_manager import (
-            global_mcp_server_manager,
-        )
-    except ImportError:
-        pytest.skip("MCP discoverable endpoints not available")
+@pytest.mark.parametrize(
+    "auth_type", (None, "none", "api_key", "bearer_token", "basic", "aws_sigv4", "authorization", "token")
+)
+@pytest.mark.parametrize("use_standard_pattern", (False, True))
+async def test_oauth_protected_resource_for_gateway_owned_auth(auth_type, use_standard_pattern):
+    from starlette.requests import Request
 
+    from litellm.proxy._experimental.mcp_server.discoverable_endpoints import (
+        _build_oauth_protected_resource_response,
+    )
+    from litellm.proxy._experimental.mcp_server.mcp_server_manager import (
+        global_mcp_server_manager,
+    )
+
+    server = _access_group_none_server().model_copy(update={"auth_type": auth_type})
+    request = Request(
+        {"type": "http", "scheme": "https", "path": "/", "headers": [(b"host", b"litellm.example.com")]}
+    )
     global_mcp_server_manager.registry.clear()
-    server = _access_group_none_server()
     global_mcp_server_manager.registry[server.server_id] = server
-
-    mock_request = MagicMock()
-    mock_request.base_url = "https://litellm.example.com/"
-    mock_request.headers = {}
-
     try:
-        with pytest.raises(HTTPException) as exc_info:
-            await _build_oauth_protected_resource_response(
-                request=mock_request,
-                mcp_server_name="access_group_server",
-                use_standard_pattern=False,
-            )
-        assert exc_info.value.status_code == 404
-        assert "not an OAuth-protected resource" in str(exc_info.value.detail)
+        response = await _build_oauth_protected_resource_response(
+            request=request,
+            mcp_server_name="access_group_server",
+            use_standard_pattern=use_standard_pattern,
+        )
+        resource_path = "/mcp/access_group_server" if use_standard_pattern else "/access_group_server/mcp"
+        assert response == {
+            "resource": f"https://litellm.example.com{resource_path}",
+            "authorization_servers": ["https://litellm.example.com/mcp"],
+            "scopes_supported": [],
+        }
     finally:
         global_mcp_server_manager.registry.clear()
 
@@ -7914,9 +7911,7 @@ async def test_oauth_protected_resource_passthrough_none_auth_not_404():
 
 @pytest.mark.asyncio
 async def test_oauth_protected_resource_404_for_unknown_server_name():
-    """A discovery request for an unknown server name returns the same 404 as a non-oauth2
-    server (not a 200 metadata doc with broken URLs), so the well-known paths cannot be used
-    to enumerate non-OAuth server names."""
+    """Unknown server names must not produce metadata advertising nonexistent resources."""
     try:
         from litellm.proxy._experimental.mcp_server.discoverable_endpoints import (
             _build_oauth_protected_resource_response,
@@ -8128,6 +8123,137 @@ async def test_token_exchange_pairs_client_secret_with_server_client_id():
     assert "client_secret" not in sent
 
 
+@pytest.mark.asyncio
+async def test_token_exchange_refresh_passes_presented_refresh_ownership():
+    from fastapi import Request
+
+    from litellm.proxy._experimental.mcp_server.discoverable_endpoints import (
+        exchange_token_with_server,
+    )
+    from litellm.proxy._experimental.mcp_server.oauth_identity_binding import RefreshTokenPresented
+    from litellm.proxy._types import MCPTransport
+    from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+    server = MCPServer(
+        server_id="srv-1",
+        name="srv-1",
+        transport=MCPTransport.http,
+        auth_type=MCPAuth.oauth2,
+        client_id="cid",
+        token_url="https://provider.example/token",
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode="enforce",
+            issuer="https://provider.example",
+            audiences=["cid"],
+        ),
+    )
+    request = MagicMock(spec=Request)
+    request.base_url = "https://litellm.example.com/"
+    request.headers = {}
+    response = MagicMock()
+    response.json.return_value = {"access_token": "at"}
+    response.raise_for_status = MagicMock()
+    client = MagicMock()
+    client.post = AsyncMock(return_value=response)
+    enforce = AsyncMock()
+
+    with (
+        patch(  # test-quality-ok: no injection seam exists for the exchange's HTTP and identity collaborators
+            "litellm.proxy._experimental.mcp_server.discoverable_endpoints.get_async_httpx_client",
+            return_value=client,
+        ),
+        patch(  # test-quality-ok: no injection seam exists for request identity extraction
+            "litellm.proxy._experimental.mcp_server.discoverable_endpoints._extract_user_id_from_request",
+            new=AsyncMock(return_value="user-a"),
+        ),
+        patch(  # test-quality-ok: captures the ownership value at the exchange boundary
+            "litellm.proxy._experimental.mcp_server.discoverable_endpoints.enforce_oauth_identity_binding",
+            new=enforce,
+        ),
+    ):
+        await exchange_token_with_server(
+            request=request,
+            mcp_server=server,
+            grant_type="refresh_token",
+            code=None,
+            redirect_uri=None,
+            client_id="cid",
+            client_secret=None,
+            code_verifier=None,
+            refresh_token="rt-1",
+        )
+
+    ownership = enforce.await_args.kwargs["refresh_ownership"]
+    assert isinstance(ownership, RefreshTokenPresented)
+    assert ownership.refresh_token == "rt-1"
+
+
+@pytest.mark.asyncio
+async def test_token_exchange_authorization_code_passes_no_refresh_ownership(monkeypatch):
+    from fastapi import Request
+
+    from litellm.proxy._experimental.mcp_server.discoverable_endpoints import (
+        exchange_token_with_server,
+        seal_bridge_authorization_code,
+    )
+    from litellm.proxy._types import MCPTransport
+    from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+    monkeypatch.setenv("LITELLM_SALT_KEY", "identity-binding-test-salt")
+    server = MCPServer(
+        server_id="srv-1",
+        name="srv-1",
+        transport=MCPTransport.http,
+        auth_type=MCPAuth.oauth2,
+        client_id="cid",
+        token_url="https://provider.example/token",
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode="enforce",
+            issuer="https://provider.example",
+            audiences=["cid"],
+        ),
+    )
+    request = MagicMock(spec=Request)
+    request.base_url = "https://litellm.example.com/"
+    request.headers = {}
+    response = MagicMock()
+    response.json.return_value = {"access_token": "at"}
+    response.raise_for_status = MagicMock()
+    client = MagicMock()
+    client.post = AsyncMock(return_value=response)
+    enforce = AsyncMock()
+
+    with (
+        patch(  # test-quality-ok: no injection seam exists for the exchange's HTTP and identity collaborators
+            "litellm.proxy._experimental.mcp_server.discoverable_endpoints.get_async_httpx_client",
+            return_value=client,
+        ),
+        patch(  # test-quality-ok: no injection seam exists for request identity extraction
+            "litellm.proxy._experimental.mcp_server.discoverable_endpoints._extract_user_id_from_request",
+            new=AsyncMock(return_value="user-a"),
+        ),
+        patch(  # test-quality-ok: captures the ownership value at the exchange boundary
+            "litellm.proxy._experimental.mcp_server.discoverable_endpoints.enforce_oauth_identity_binding",
+            new=enforce,
+        ),
+    ):
+        result = await exchange_token_with_server(
+            request=request,
+            mcp_server=server,
+            grant_type="authorization_code",
+            code=seal_bridge_authorization_code("auth-code", "user-a", "srv-1", "login-nonce"),
+            redirect_uri="https://litellm.example.com/callback",
+            client_id="cid",
+            client_secret=None,
+            code_verifier="test-verifier",
+        )
+
+    assert result.status_code == 200
+    assert json.loads(result.body)["access_token"] == "at"
+    assert enforce.await_args.kwargs["refresh_ownership"] is None
+    assert enforce.await_args.kwargs["expected_nonce"] == "login-nonce"
+
+
 def _upstream_token_response(status_code: int, *, json_body: object = None, text_body: str = "") -> "httpx.Response":
     import httpx
 
@@ -10921,3 +11047,97 @@ def test_introspect_route_answers_for_authenticated_caller(monkeypatch):
     assert active.status_code == 200
     assert active.json()["active"] is True
     assert active.json()["sub"] == "u1"
+
+
+@pytest.mark.asyncio
+async def test_identity_bound_authorization_carries_nonce_and_caller_through_callback(monkeypatch):
+    from http.cookies import SimpleCookie
+    from urllib.parse import parse_qs, urlparse
+    from fastapi import Request
+    from litellm.proxy._experimental.mcp_server.discoverable_endpoints import (
+        _oauth_state_cookie_name, authorize_with_server, callback, open_bridge_authorization_code,
+    )
+    from litellm.types.mcp import MCPTransport
+    from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+    monkeypatch.setenv("LITELLM_SALT_KEY", "identity-binding-test-salt")
+    server = MCPServer(
+        server_id="srv", name="srv", transport=MCPTransport.http, auth_type=MCPAuth.oauth2,
+        client_id="client", authorization_url="https://idp.example.com/authorize",
+        token_url="https://idp.example.com/token",
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode="enforce", issuer="https://idp.example.com", audiences=["client"],
+        ),
+    )
+    request = Request({"type": "http", "scheme": "https", "server": ("proxy.example.com", 443),
+                       "path": "/authorize", "query_string": b"", "headers": []})
+    with (
+        patch(  # test-quality-ok: isolate authenticated request resolution from the real encrypted OAuth round trip
+              "litellm.proxy._experimental.mcp_server.discoverable_endpoints._extract_user_id_from_request",
+              new=AsyncMock(return_value="alice")),
+        patch(  # test-quality-ok: isolate user access lookup while testing nonce and caller preservation
+              "litellm.proxy._experimental.mcp_server.discoverable_endpoints._bridge_authorize_access_denial",
+              new=AsyncMock(return_value=None)),
+    ):
+        authorized = await authorize_with_server(
+            request, server, "client", "http://127.0.0.1:6274/callback", state="client-state",
+            code_challenge="pkce-challenge", code_challenge_method="S256",
+        )
+    query = parse_qs(urlparse(authorized.headers["location"]).query)
+    assert len(query["nonce"][0]) >= 32
+    cookies = SimpleCookie()
+    cookies.load(authorized.headers["set-cookie"])
+    name = _oauth_state_cookie_name(query["state"][0])
+    callback_request = Request({**request.scope, "path": "/callback",
+                               "headers": [(b"cookie", f"{name}={cookies[name].value}".encode())]})
+    completed = await callback(callback_request, code="upstream-code", state=query["state"][0])
+    returned = parse_qs(urlparse(completed.headers["location"]).query)
+    sealed = open_bridge_authorization_code(returned["code"][0])
+    assert sealed.litellm_user_id == "alice"
+    assert sealed.mcp_server_id == "srv"
+    assert sealed.upstream_code == "upstream-code"
+    assert sealed.oauth_nonce == query["nonce"][0]
+    assert returned["state"] == ["client-state"]
+
+
+@pytest.mark.asyncio
+async def test_enforced_login_warms_verified_token_readable_without_database_lookup(monkeypatch):
+    from types import SimpleNamespace
+    from litellm.caching.caching import DualCache
+    from litellm.proxy import proxy_server
+    from litellm.proxy._experimental.mcp_server import db, mcp_server_manager
+    from litellm.proxy._experimental.mcp_server.discoverable_endpoints import _store_per_user_token_server_side
+    from litellm.proxy._experimental.mcp_server.oauth2_token_cache import mcp_per_user_token_cache
+    from litellm.proxy._experimental.mcp_server.oauth_identity_binding import current_binding_proof
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.dual_cache_token_backend import DualCacheTokenCacheBackend
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.oauth_token_store import CachedOAuthTokenStore
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.per_user_oauth_store import LazyPerUserOAuthTokenStore
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.v2_token_store import V2PerUserTokenStore
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    server = MCPServer(
+        server_id="srv", name="srv", transport="http", auth_type="oauth2",
+        oauth_identity_binding={"mode": "enforce", "issuer": "https://idp.example", "audiences": ["client"],
+                                "caller_field": "user_id", "principal_claim": "sub"},
+    )
+    proof = await current_binding_proof(server.oauth_identity_binding, "alice", "srv")
+    cache = DualCache()
+    monkeypatch.setenv("LITELLM_SALT_KEY", "test-cache-warm-encryption-salt")
+    monkeypatch.setattr(proxy_server, "user_api_key_cache", cache)
+    monkeypatch.setattr(proxy_server, "prisma_client", MagicMock())
+    monkeypatch.setattr(mcp_server_manager, "global_mcp_server_manager", SimpleNamespace(invalidate_user_oauth_token_cache=AsyncMock()))
+    monkeypatch.setattr(db, "store_user_oauth_credential", AsyncMock())
+    await _store_per_user_token_server_side(
+        server=server, user_id="alice", token_response={"access_token": "alice-token", "refresh_token": "private", "expires_in": 3600},
+        identity_binding_proof=proof,
+    )
+    read = AsyncMock(return_value=None)
+    cached = CachedOAuthTokenStore(
+        V2PerUserTokenStore(read), default_ttl_seconds=300, backend=DualCacheTokenCacheBackend(cache, mcp_per_user_token_cache._codec()),
+    )
+    store = LazyPerUserOAuthTokenStore(lambda _: server, store_builder=lambda _: (cached, True), redis_available=lambda: True)
+    token = await store.fetch("alice", "srv")
+    assert token is not None and token.access_token == "alice-token"
+    assert token.identity_binding_proof == proof
+    assert token.refresh_token is None
+    read.assert_not_awaited()
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_gateway_dcr_flow.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_gateway_dcr_flow.py
index 73a52a8d2e8..7c80ee77cd7 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_gateway_dcr_flow.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_gateway_dcr_flow.py
@@ -6,6 +6,7 @@ import re
 from base64 import urlsafe_b64encode
 from datetime import datetime, timedelta, timezone
 from http.cookies import SimpleCookie
+from typing import Final
 from urllib.parse import parse_qs, urlparse
 
 import pytest
@@ -18,6 +19,7 @@ from litellm.proxy._experimental.mcp_server.gateway_dcr_flow import (
     GATEWAY_AUTH_CODE_PREFIX,
     GATEWAY_AUTH_CODE_TTL_SECONDS,
     MANUAL_DELIVERY_AUTH_CODE_TTL_SECONDS,
+    MAX_CLIENT_ID_LENGTH,
     ConsentTeam,
     MintedProxyCredential,
     _GatewayAuthCode,
@@ -53,6 +55,13 @@ from litellm.proxy._experimental.mcp_server.outbound_credentials.session_token i
 
 MASTER_KEY = "sk-gateway-dcr-flow-tests"
 REDIRECT_URI = "https://claude.ai/api/mcp/auth_callback"
+VSCODE_REDIRECT_URIS: Final = (
+    "https://insiders.vscode.dev/redirect",
+    "https://vscode.dev/redirect",
+    "http://127.0.0.1/",
+    "http://127.0.0.1:33418/",
+)
+MAX_LENGTH_REDIRECT_URIS: Final = tuple(f"https://client.example/{index}/".ljust(256, "a") for index in range(4))
 CODE_VERIFIER = "verifier-" + "v" * 43
 CODE_CHALLENGE = urlsafe_b64encode(hashlib.sha256(CODE_VERIFIER.encode("ascii")).digest()).rstrip(b"=").decode("ascii")
 
@@ -104,6 +113,58 @@ async def test_register_mints_stateless_public_client():
     assert record.redirect_uris == (REDIRECT_URI,)
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize("redirect_uris", [VSCODE_REDIRECT_URIS, MAX_LENGTH_REDIRECT_URIS])
+async def test_register_four_callbacks_preserves_metadata(redirect_uris: tuple[str, ...]) -> None:
+    response: Final = await register_aggregate_client(
+        request=_request(path="/register", method="POST"),
+        request_body={
+            "client_name": "Visual Studio Code",
+            "client_uri": "https://code.visualstudio.com",
+            "grant_types": ["authorization_code", "refresh_token"],
+            "response_types": ["code"],
+            "redirect_uris": list(redirect_uris),
+            "token_endpoint_auth_method": "none",
+            "application_type": "native",
+        },
+    )
+    assert response.status_code == 201
+    body: Final = json.loads(response.body)
+    assert body["redirect_uris"] == list(redirect_uris)
+    assert body["token_endpoint_auth_method"] == "none"
+    assert "client_secret" not in body
+    assert len(body["client_id"]) <= MAX_CLIENT_ID_LENGTH
+    record: Final = open_gateway_dcr_client(body["client_id"])
+    assert record is not None
+    assert record.redirect_uris == redirect_uris
+
+
+@pytest.mark.asyncio
+async def test_register_rejects_five_valid_callbacks() -> None:
+    response: Final = await register_aggregate_client(
+        request=_request(path="/register", method="POST"),
+        request_body={"redirect_uris": [*VSCODE_REDIRECT_URIS, "http://127.0.0.1:33419/"]},
+    )
+    assert response.status_code == 400
+    assert json.loads(response.body) == {
+        "error": "invalid_redirect_uri",
+        "error_description": "redirect_uris must be a list of 1 to 4 URIs",
+    }
+
+
+@pytest.mark.asyncio
+async def test_register_four_callbacks_preserves_encoded_size_guard() -> None:
+    response: Final = await register_aggregate_client(
+        request=_request(path="/register", method="POST"),
+        request_body={"redirect_uris": [f"https://client.example/{index}/".ljust(256, "é") for index in range(4)]},
+    )
+    assert response.status_code == 400
+    assert json.loads(response.body) == {
+        "error": "invalid_client_metadata",
+        "error_description": "registered metadata is too large",
+    }
+
+
 @pytest.mark.asyncio
 async def test_register_allows_loopback_http_for_dev_clients():
     body = await _register(["http://localhost:6274/oauth/callback"])
@@ -162,7 +223,6 @@ async def test_register_rejects_userinfo_spoofed_origin():
         ["https://claude.ai/cb#fragment"],
         ["ftp://claude.ai/cb"],
         ["https://a.example.com/" + "p" * 300],
-        ["https://a.example.com/1", "https://a.example.com/2", "https://a.example.com/3", "https://a.example.com/4"],
         [12345],
     ],
 )
@@ -248,12 +308,14 @@ def _flow_cookie_from(response) -> tuple:
 
 
 @pytest.mark.asyncio
-async def test_full_walk_register_authorize_complete_token_and_replay():
+@pytest.mark.parametrize("redirect_uris", [(REDIRECT_URI,), VSCODE_REDIRECT_URIS, MAX_LENGTH_REDIRECT_URIS])
+async def test_full_walk_register_authorize_complete_token_and_replay(redirect_uris: tuple[str, ...]):
     """The whole front door on one deterministic walk: register -> authorize ->
     complete -> token, then the security edges on the same artifacts (user mismatch,
     PKCE mismatch, single-use replay, refresh rotation, cross-client refresh)."""
-    client_id = (await _register([REDIRECT_URI]))["client_id"]
-    authorize_response = _authorize(client_id, session_user_id="u1")
+    redirect_uri: Final = redirect_uris[-1]
+    client_id = (await _register(list(redirect_uris)))["client_id"]
+    authorize_response = _authorize(client_id, session_user_id="u1", redirect_uri=redirect_uri)
     handle, cookies = _flow_cookie_from(authorize_response)
 
     denied = await complete_connect_flow(
@@ -280,7 +342,7 @@ async def test_full_walk_register_authorize_complete_token_and_replay():
     )
     assert completed.status_code == 303
     redirect = urlparse(completed.headers["location"])
-    assert f"{redirect.scheme}://{redirect.netloc}{redirect.path}" == REDIRECT_URI
+    assert f"{redirect.scheme}://{redirect.netloc}{redirect.path}" == redirect_uri
     params = parse_qs(redirect.query)
     assert params["state"] == ["client-state-123"]
     code = params["code"][0]
@@ -293,7 +355,7 @@ async def test_full_walk_register_authorize_complete_token_and_replay():
             "request": _request("/token", method="POST"),
             "grant_type": "authorization_code",
             "code": code,
-            "redirect_uri": REDIRECT_URI,
+            "redirect_uri": redirect_uri,
             "client_id": client_id,
             "code_verifier": CODE_VERIFIER,
             "refresh_token": None,
@@ -833,7 +895,7 @@ async def test_manual_delivery_page_renders_the_url_as_data_never_as_a_shell_com
     assert 'value="' in body
 
 
-def _scoped_mcp_server(name="github", **kw):
+def _scoped_mcp_server(name="github", auth_type="oauth2", **kw):
     from litellm.types.mcp import MCPAuth
     from litellm.types.mcp_server.mcp_server_manager import MCPServer
 
@@ -844,7 +906,7 @@ def _scoped_mcp_server(name="github", **kw):
         alias=name,
         url="https://upstream.example/mcp",
         transport="http",
-        auth_type=MCPAuth.oauth2,
+        auth_type=MCPAuth(auth_type) if auth_type is not None else None,
         **kw,
     )
 
@@ -2044,3 +2106,45 @@ async def test_introspect_fails_closed_on_dead_user_and_503s_on_outage():
 
     status, body = await _introspect(minted.token.get_secret_value(), master_key=None)
     assert (status, body["error"]) == (500, "server_error")
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "auth_type", [None, "none", "api_key", "bearer_token", "basic", "authorization", "token", "aws_sigv4"]
+)
+@pytest.mark.parametrize("resource", ["https://llm.example.com/mcp/github", "https://llm.example.com/github/mcp"])
+async def test_gateway_owned_resource_stays_scoped_through_consent_and_refresh(auth_type, resource):
+    from unittest.mock import patch
+
+    client_id = (await _register([REDIRECT_URI]))["client_id"]
+    server = _scoped_mcp_server(auth_type=auth_type)
+    vendor = _VendorCredential("absent")
+    with patch(_MANAGER_PATCH) as manager:
+        manager.get_mcp_server_by_name.return_value = server
+        response = _scoped_authorize(client_id, resource)
+    described = await _describe_page(response, scoped_server=server, vendor=vendor)
+    assert json.loads(described.body) == {
+        "state": "m2m",
+        "client_origin": "https://claude.ai",
+        "server_id": "github-id",
+        "server_name": "github",
+        "connected": True,
+    }
+    unreachable = await _complete_page(response, scoped_server=server, reachable=_ServerReachability(False))
+    assert unreachable.status_code == 400
+    cache = DualCache()
+    completed = await _complete_page(response, scoped_server=server, vendor=vendor, cache=cache)
+    assert completed.status_code == 303
+    assert vendor.calls == []
+    code = parse_qs(urlparse(completed.headers["location"]).query)["code"][0]
+    with patch(_MANAGER_PATCH) as manager:
+        manager.get_mcp_server_by_name.return_value = server
+        redeemed = await _redeem(code, client_id, cache=cache, resource=resource)
+    assert redeemed.status_code == 200
+    payload = json.loads(redeemed.body)
+    assert _opened_principal(payload).resource_server_id == "github-id"
+    renewed = await _redeem(
+        None, client_id, cache=cache, grant_type="refresh_token", refresh_token=payload["refresh_token"]
+    )
+    assert renewed.status_code == 200
+    assert _opened_principal(json.loads(renewed.body)).resource_server_id == "github-id"
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_debug.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_debug.py
index 8ca9edc1ff9..0ed78fcfc9d 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_debug.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_debug.py
@@ -3,15 +3,21 @@ Tests for MCPDebug — MCP OAuth2 debug response headers.
 """
 
 import asyncio
-from unittest.mock import MagicMock
+from typing import Final
+
+import pytest
+from starlette.types import Message
+
+from litellm.proxy._experimental.mcp_server.outbound_credentials.types import AuthResolution
 
 import httpx
-import pytest
 
 from litellm.proxy._experimental.mcp_server.mcp_debug import (
     MCP_DEBUG_REQUEST_HEADER,
     MCPDebug,
     describe_upstream_http_failure,
+
+    MCPAuthDiagnostics,
 )
 
 
@@ -170,77 +176,6 @@ class TestBuildDebugHeaders:
         assert set(headers.keys()) == expected_keys
 
 
-class TestResolveAuthResolution:
-    def _make_server(self, **kwargs):
-        server = MagicMock()
-        server.alias = kwargs.get("alias", "test")
-        server.server_name = kwargs.get("server_name", "test")
-        server.has_client_credentials = kwargs.get("has_client_credentials", False)
-        server.authentication_token = kwargs.get("authentication_token", None)
-        server.auth_type = kwargs.get("auth_type", None)
-        return server
-
-    def test_per_request_header(self):
-        server = self._make_server()
-        result = MCPDebug.resolve_auth_resolution(
-            server,
-            mcp_auth_header="Bearer xxx",
-            mcp_server_auth_headers=None,
-            oauth2_headers=None,
-        )
-        assert result == "per-request-header"
-
-    def test_server_specific_header(self):
-        server = self._make_server(alias="atlas")
-        result = MCPDebug.resolve_auth_resolution(
-            server,
-            mcp_auth_header=None,
-            mcp_server_auth_headers={"atlas": {"Authorization": "Bearer xxx"}},
-            oauth2_headers=None,
-        )
-        assert result == "per-request-header"
-
-    def test_m2m(self):
-        server = self._make_server(has_client_credentials=True)
-        result = MCPDebug.resolve_auth_resolution(
-            server,
-            mcp_auth_header=None,
-            mcp_server_auth_headers=None,
-            oauth2_headers=None,
-        )
-        assert result == "m2m-client-credentials"
-
-    def test_static_token(self):
-        server = self._make_server(authentication_token="static-tok")
-        result = MCPDebug.resolve_auth_resolution(
-            server,
-            mcp_auth_header=None,
-            mcp_server_auth_headers=None,
-            oauth2_headers=None,
-        )
-        assert result == "static-token"
-
-    def test_oauth2_passthrough(self):
-        server = self._make_server(auth_type="oauth2")
-        result = MCPDebug.resolve_auth_resolution(
-            server,
-            mcp_auth_header=None,
-            mcp_server_auth_headers=None,
-            oauth2_headers={"Authorization": "Bearer eyJ..."},
-        )
-        assert result == "oauth2-passthrough"
-
-    def test_no_auth(self):
-        server = self._make_server()
-        result = MCPDebug.resolve_auth_resolution(
-            server,
-            mcp_auth_header=None,
-            mcp_server_auth_headers=None,
-            oauth2_headers=None,
-        )
-        assert result == "no-auth"
-
-
 class TestWrapSendWithDebugHeaders:
     def test_injects_headers(self):
         captured = []
@@ -464,3 +399,89 @@ def test_encoded_form_credentials_are_decoded_before_redaction(body):
     detail = describe_upstream_http_failure(httpx.HTTPStatusError("failure", request=request, response=response))
     assert detail is not None and "client_id=visible" in detail
     assert "first" not in detail and "second" not in detail
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("source", tuple(AuthResolution))
+@pytest.mark.parametrize("method", ("GET", "DELETE", "POST"))
+async def test_debug_defers_resolution_until_first_frame_only_for_post(source: AuthResolution, method: str) -> None:
+    captured: Final[list[Message]] = []
+    diagnostics: Final = MCPAuthDiagnostics()
+
+    async def send(message: Message) -> None:
+        captured.append(message)
+
+    wrapped: Final = MCPDebug.wrap_send_with_debug_headers(
+        send, diagnostics.headers(), diagnostics.headers, request_method=method
+    )
+    await wrapped({"type": "http.response.start", "status": 200, "headers": []})
+    assert len(captured) == (0 if method == "POST" else 1)
+    diagnostics.record("s1", source)
+    body: Final[Message] = {"type": "http.response.body", "body": b"data: pong\n\n", "more_body": True}
+    await wrapped(body)
+    assert dict(captured[0]["headers"])[b"x-mcp-debug-auth-resolution"] == (
+        source.value.encode() if method == "POST" else b"unresolved"
+    )
+    assert captured[1] == body
+
+
+@pytest.mark.asyncio
+async def test_early_stream_frame_reports_unresolved_without_waiting() -> None:
+    captured: Final[list[Message]] = []
+    diagnostics: Final = MCPAuthDiagnostics()
+
+    async def send(message: Message) -> None:
+        captured.append(message)
+
+    wrapped: Final = MCPDebug.wrap_send_with_debug_headers(send, {}, diagnostics.headers, request_method="POST")
+    await wrapped({"type": "http.response.start", "status": 200, "headers": []})
+    await wrapped({"type": "http.response.body", "body": b": ping\n\n", "more_body": True})
+    diagnostics.record("s1", AuthResolution.stored_user_token)
+    await wrapped({"type": "http.response.body", "body": b"data: pong\n\n", "more_body": False})
+    assert len(captured) == 3
+    assert dict(captured[0]["headers"])[b"x-mcp-debug-auth-resolution"] == b"unresolved"
+
+
+def test_diagnostics_keep_requests_separate_and_do_not_collapse_multiple_servers() -> None:
+    alice: Final = MCPAuthDiagnostics()
+    bob: Final = MCPAuthDiagnostics()
+    alice.record("s1", AuthResolution.stored_user_token)
+    assert bob.resolution() == "unresolved"
+    alice.record("s1", AuthResolution.token_exchange)
+    assert alice.resolution() == "token-exchange"
+    alice.record("s2", AuthResolution.static_token)
+    assert alice.resolution() == "multiple"
+    assert alice.headers()["x-mcp-debug-auth-resolutions"] == '{"s1":"token-exchange","s2":"static-token"}'
+
+
+@pytest.mark.asyncio
+async def test_concurrent_mcp_messages_record_on_their_own_http_scope() -> None:
+    from unittest.mock import MagicMock
+
+    from mcp.server.lowlevel.server import request_ctx
+    from mcp.shared.context import RequestContext
+    from starlette.requests import Request
+
+    from litellm.proxy._experimental.mcp_server.mcp_debug import (
+        MCP_AUTH_DIAGNOSTICS_SCOPE_KEY,
+        record_auth_resolution,
+    )
+
+    session: Final = MagicMock()
+    first: Final = MCPAuthDiagnostics()
+    second: Final = MCPAuthDiagnostics()
+
+    async def record(diagnostics: MCPAuthDiagnostics, source: AuthResolution) -> None:
+        context: Final = RequestContext(
+            request_id=1, meta=None, session=session, lifespan_context=None,
+            request=Request({"type": "http", MCP_AUTH_DIAGNOSTICS_SCOPE_KEY: diagnostics}),
+        )
+        token: Final = request_ctx.set(context)
+        try:
+            await asyncio.sleep(0)
+            record_auth_resolution("same-server", source)
+        finally:
+            request_ctx.reset(token)
+
+    await asyncio.gather(record(first, AuthResolution.stored_user_token), record(second, AuthResolution.per_request_header))
+    assert first.resolution() == "stored-user-token"
+    assert second.resolution() == "per-request-header"
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_partial_update.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_partial_update.py
index c0d055edb7f..669e094fee4 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_partial_update.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_partial_update.py
@@ -1,10 +1,11 @@
 """
-Tests for partial-update semantics of PUT /v1/mcp/server.
+Tests for partial-update semantics of PUT /v1/mcp/server and PUT /v1/mcp/toolset.
 
 A partial update must only write the fields the caller explicitly provided.
 Omitting a field must NOT reset it to its Pydantic schema default (e.g.
 ``transport=sse``, ``mcp_access_groups=[]``, ``allow_all_keys=False``), which
-would silently overwrite the existing DB row.
+would silently overwrite the existing DB row, and a field the caller sent as null
+must be cleared rather than left at its stored value.
 """
 
 import json
@@ -850,3 +851,69 @@ async def test_cf_pair_switch_does_not_clear_dcr_bridge():
     data = UpdateMCPServerRequest(server_id="s", auth_type="oauth_delegate")
     data_dict = await _run_update_with_existing(data, existing_auth_type="true_passthrough")
     assert "dcr_bridge" not in data_dict
+
+
+def _mock_toolset_prisma():
+    """A prisma double whose update answers with a row the reader can expand, so the
+    call under test returns instead of failing inside the row mapper."""
+    updated_row = MagicMock()
+    updated_row.model_dump.return_value = {
+        "toolset_id": "ts-1",
+        "toolset_name": "ops",
+        "description": None,
+        "tools": "[]",
+    }
+    mock_prisma = MagicMock()
+    mock_prisma.db.litellm_mcptoolsettable = AsyncMock()
+    mock_prisma.db.litellm_mcptoolsettable.update = AsyncMock(return_value=updated_row)
+    return mock_prisma
+
+
+async def _run_toolset_update(payload: dict) -> dict:
+    """The columns PUT /v1/mcp/toolset writes for this payload, minus the audit stamp
+    every write carries. The prisma double is injected, so nothing is patched."""
+    from litellm.proxy._experimental.mcp_server.toolset_db import update_mcp_toolset
+    from litellm.types.mcp_server.mcp_toolset import UpdateMCPToolsetRequest
+
+    mock_prisma = _mock_toolset_prisma()
+    await update_mcp_toolset(mock_prisma, UpdateMCPToolsetRequest.model_validate(payload), "test-user")
+    written = dict(mock_prisma.db.litellm_mcptoolsettable.update.call_args[1]["data"])
+    assert written["updated_by"] == "test-user"
+    return {name: value for name, value in written.items() if name != "updated_by"}
+
+
+@pytest.mark.asyncio
+async def test_toolset_partial_update_clears_description_on_explicit_null():
+    """The dump used to drop None, so a null description could never clear the stored
+    one: the toolset kept a description its owner had deleted."""
+    assert await _run_toolset_update({"toolset_id": "ts-1", "description": None}) == {"description": None}
+
+
+@pytest.mark.asyncio
+async def test_toolset_partial_update_omits_the_fields_the_caller_left_out():
+    tools = [{"server_id": "s1", "tool_name": "alpha"}]
+    assert await _run_toolset_update({"toolset_id": "ts-1", "tools": tools}) == {"tools": json.dumps(tools)}
+
+
+@pytest.mark.asyncio
+async def test_toolset_partial_update_ignores_null_tools_rather_than_revoking_them():
+    """A client that sends tools=null means "leave the selection alone", so the grants
+    survive. Clearing them is an explicit [], which cannot be confused with an omitted
+    field; treating null as a clear would silently revoke every tool the toolset grants."""
+    assert await _run_toolset_update({"toolset_id": "ts-1", "tools": None, "description": "kept"}) == {
+        "description": "kept"
+    }
+
+
+@pytest.mark.asyncio
+async def test_toolset_partial_update_empties_the_selection_on_an_explicit_empty_list():
+    assert await _run_toolset_update({"toolset_id": "ts-1", "tools": []}) == {"tools": "[]"}
+
+
+@pytest.mark.asyncio
+async def test_toolset_partial_update_ignores_a_null_name():
+    """A toolset always has a name, so a null toolset_name is a no-op, not a clear
+    that would write a NOT NULL column to null."""
+    assert await _run_toolset_update({"toolset_id": "ts-1", "toolset_name": None, "description": "kept"}) == {
+        "description": "kept"
+    }
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_proxy_mode.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_proxy_mode.py
index 413785529d5..67b7c5a3414 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_proxy_mode.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_proxy_mode.py
@@ -1,355 +1,118 @@
 import json
-from collections.abc import Iterator
-from unittest.mock import AsyncMock, patch
+from datetime import datetime
 
 import pytest
-from mcp.types import CallToolResult, TextContent, Tool
+from fastapi import HTTPException
+from mcp.shared.exceptions import McpError
+from pydantic import AnyUrl
 
+import litellm
+from litellm.integrations.custom_logger import CustomLogger
 from litellm.proxy._experimental.mcp_server import server
-from litellm.proxy._experimental.mcp_server.faults.list_outcomes import AggregateToolListing
-from litellm.proxy._experimental.mcp_server.tool_search import (
-    MCP_PROXY_CALL_TOOL_NAME,
-    MCP_PROXY_SCHEMA_TOOL_NAME,
-    MCP_PROXY_SEARCH_TOOL_NAME,
-    handle_mcp_proxy_tool,
-    mcp_proxy_tool_id,
-    with_mcp_proxy_identity,
-)
+from litellm.proxy._experimental.mcp_server.mcp_context import _mcp_proxy_mode
 from litellm.proxy._types import LiteLLM_ObjectPermissionTable, UserAPIKeyAuth
-from litellm.types.mcp import MCPTransport
-from litellm.types.mcp_server.mcp_server_manager import MCPServer
 
-TOOL = Tool.model_validate(
-    {
-        "name": "math_stdio-add",
-        "description": "Add two numbers",
-        "inputSchema": {
-            "type": "object",
-            "properties": {"a": {"type": "integer"}, "b": {"type": "integer"}},
-            "required": ["a", "b"],
-        },
-        "outputSchema": {"type": "object"},
-        "_meta": {"litellm.ai/proxy_tool_identity": {"server_id": "server-1", "tool_name": "math_stdio-add"}},
-    }
-)
 AUTH = UserAPIKeyAuth(api_key="key")
 
 
-def _text(result: CallToolResult) -> object:
-    return json.loads(result.content[0].text)
-
-
-@pytest.mark.asyncio
-async def test_proxy_search_returns_opaque_id_and_schema() -> None:
-    with (
-        patch(  # test-quality-ok: isolate authorized catalog owner
-            "litellm.proxy._experimental.mcp_server.server._list_mcp_tools",
-            new_callable=AsyncMock,
-            return_value=AggregateToolListing(tools=[TOOL], outcomes={}),
-        ),
-    ):
-        result = await handle_mcp_proxy_tool(MCP_PROXY_SEARCH_TOOL_NAME, {"query": "add"}, AUTH)
-
-    item = _text(result)[0]
-    assert item["tool_id"] == mcp_proxy_tool_id(TOOL)
-    assert item["name"] == TOOL.name
-    assert "inputSchema" not in item
-    assert "outputSchema" not in item
-    assert len(item["tool_id"]) == 32
-
-
-@pytest.mark.asyncio
-async def test_proxy_schema_and_call_resolve_current_authorized_catalog() -> None:
-    executed = CallToolResult(content=[TextContent(type="text", text="3")], isError=False)
-    with (
-        patch(  # test-quality-ok: isolate authorized catalog owner
-            "litellm.proxy._experimental.mcp_server.server._list_mcp_tools",
-            new_callable=AsyncMock,
-            return_value=AggregateToolListing(tools=[TOOL], outcomes={}),
-        ),
-        patch(  # test-quality-ok: isolate execution delegate seam
-            "litellm.proxy._experimental.mcp_server.tool_search.handle_mcp_tool_call",
-            new_callable=AsyncMock,
-            return_value=executed,
-        ) as call,
-    ):
-        schema = await handle_mcp_proxy_tool(
-            MCP_PROXY_SCHEMA_TOOL_NAME,
-            {"tool_id": mcp_proxy_tool_id(TOOL)},
-            AUTH,
-        )
-        result = await handle_mcp_proxy_tool(
-            MCP_PROXY_CALL_TOOL_NAME,
-            {"tool_id": mcp_proxy_tool_id(TOOL), "arguments": {"a": 1, "b": 2}},
-            AUTH,
-        )
-
-    assert _text(schema)["inputSchema"] == TOOL.inputSchema
-    assert result is executed
-    assert call.await_args.kwargs["tool_name"] == TOOL.name
-    assert call.await_args.kwargs["arguments"] == {"a": 1, "b": 2}
-    assert call.await_args.kwargs["requested_server_id"] == "server-1"
-
-
-@pytest.mark.asyncio
-async def test_proxy_rejects_stale_id_and_invalid_arguments_before_dispatch() -> None:
-    with (
-        patch(  # test-quality-ok: isolate authorized catalog owner
-            "litellm.proxy._experimental.mcp_server.server._list_mcp_tools",
-            new_callable=AsyncMock,
-            return_value=AggregateToolListing(tools=[TOOL], outcomes={}),
-        ),
-        patch(  # test-quality-ok: isolate execution delegate seam
-            "litellm.proxy._experimental.mcp_server.tool_search.handle_mcp_tool_call", new_callable=AsyncMock
-        ) as call,
-    ):
-        stale = await handle_mcp_proxy_tool(MCP_PROXY_SCHEMA_TOOL_NAME, {"tool_id": "stale"}, AUTH)
-        invalid = await handle_mcp_proxy_tool(
-            MCP_PROXY_CALL_TOOL_NAME,
-            {"tool_id": mcp_proxy_tool_id(TOOL), "arguments": "wrong"},
-            AUTH,
-        )
-        falsy = await handle_mcp_proxy_tool(
-            MCP_PROXY_CALL_TOOL_NAME,
-            {"tool_id": mcp_proxy_tool_id(TOOL), "arguments": False},
-            AUTH,
-        )
-        invalid_schema = await handle_mcp_proxy_tool(
-            MCP_PROXY_CALL_TOOL_NAME,
-            {"tool_id": mcp_proxy_tool_id(TOOL), "arguments": {"a": "wrong"}},
-            AUTH,
-        )
-
-    assert stale.isError is True
-    assert invalid.isError is True
-    assert falsy.isError is True
-    assert invalid_schema.isError is True
-    call.assert_not_awaited()
-
-
-@pytest.mark.asyncio
-async def test_proxy_call_builds_logging_object() -> None:
-    from litellm.proxy._experimental.mcp_server.mcp_context import _mcp_proxy_mode
-
-    sentinel = object()
-    result = CallToolResult(content=[TextContent(type="text", text="ok")], isError=False)
+@pytest.fixture
+def proxy_mode():
     token = _mcp_proxy_mode.set(True)
     try:
-        with (
-            patch.object(  # test-quality-ok: isolate logging pipeline seam
-                server, "_build_virtual_call_logging_obj", new_callable=AsyncMock, return_value=sentinel
-            ) as build,
-            patch(  # test-quality-ok: isolate proxy dispatch seam
-                "litellm.proxy._experimental.mcp_server.tool_search.handle_mcp_proxy_tool",
-                new_callable=AsyncMock,
-                return_value=result,
-            ) as handle,
-        ):
-            actual = await server._dispatch_virtual_mcp_tool(
-                name=MCP_PROXY_CALL_TOOL_NAME,
-                arguments={"tool_id": "id", "arguments": {}},
-                user_api_key_auth=AUTH,
-                client_ip=None,
-            )
+        yield
     finally:
         _mcp_proxy_mode.reset(token)
 
-    assert actual is result
-    build.assert_awaited_once()
-    assert handle.await_args.kwargs["litellm_logging_obj"] is sentinel
-
 
 @pytest.mark.asyncio
+@pytest.mark.usefixtures("proxy_mode")
 async def test_proxy_call_rejects_non_proxy_tool_names() -> None:
-    from litellm.proxy._experimental.mcp_server.mcp_context import _mcp_proxy_mode
-
-    token = _mcp_proxy_mode.set(True)
-    try:
-        result = await server._dispatch_virtual_mcp_tool(
-            name="math_stdio-add",
-            arguments={"a": 1, "b": 2},
-            user_api_key_auth=AUTH,
-            client_ip=None,
-        )
-    finally:
-        _mcp_proxy_mode.reset(token)
+    result = await server._dispatch_virtual_mcp_tool(
+        name="math_stdio-add", arguments={"a": 1, "b": 2}, user_api_key_auth=AUTH, client_ip=None
+    )
 
     assert result is not None
     assert result.isError is True
-    assert "unavailable" in result.content[0].text
+    assert "unavailable on /mcp/proxy" in result.content[0].text
 
 
 @pytest.mark.asyncio
+@pytest.mark.usefixtures("proxy_mode")
 async def test_proxy_rejects_non_tool_protocol_operations() -> None:
-    from mcp.shared.exceptions import McpError
-    from pydantic import AnyUrl
-
-    from litellm.proxy._experimental.mcp_server.mcp_context import _mcp_proxy_mode
-
-    token = _mcp_proxy_mode.set(True)
-    try:
-        with pytest.raises(McpError):
-            await server.list_prompts()
-        with pytest.raises(McpError):
-            await server.get_prompt("prompt", {})
-        with pytest.raises(McpError):
-            await server.list_resources()
-        with pytest.raises(McpError):
-            await server.list_resource_templates()
-        with pytest.raises(McpError):
-            await server.read_resource(AnyUrl("https://example.com/resource"))
-    finally:
-        _mcp_proxy_mode.reset(token)
-
-
-@pytest.mark.asyncio
-async def test_proxy_list_mode_has_fixed_definitions_without_search_flag() -> None:
-    from litellm.proxy._experimental.mcp_server.mcp_context import _mcp_proxy_mode
-
-    token = _mcp_proxy_mode.set(True)
-    try:
-        with patch(  # test-quality-ok: isolate authenticated MCP context seam
-            "litellm.proxy._experimental.mcp_server.server.get_or_extract_auth_context",
-            new_callable=AsyncMock,
-            return_value=(AUTH, None, None, None, None, None, None),
-        ):
-            tools = await server.handle_list_tools()
-            options = server.server.create_initialization_options()
-    finally:
-        _mcp_proxy_mode.reset(token)
-
-    assert {tool.name for tool in tools} == {
-        MCP_PROXY_SEARCH_TOOL_NAME,
-        MCP_PROXY_SCHEMA_TOOL_NAME,
-        MCP_PROXY_CALL_TOOL_NAME,
-    }
+    options = server.server.create_initialization_options()
     assert options.capabilities.prompts is None
     assert options.capabilities.resources is None
     assert options.capabilities.tools is not None
 
+    with pytest.raises(McpError):
+        await server.list_prompts()
+    with pytest.raises(McpError):
+        await server.get_prompt("prompt", {})
+    with pytest.raises(McpError):
+        await server.list_resources()
+    with pytest.raises(McpError):
+        await server.list_resource_templates()
+    with pytest.raises(McpError):
+        await server.read_resource(AnyUrl("https://example.com/resource"))
 
-def _server(server_id: str, name: str, **overrides: object) -> MCPServer:
-    return MCPServer(
-        server_id=server_id,
-        name=name,
-        server_name=name,
-        url=f"http://{name}.test",
-        transport=MCPTransport.http,
-        **overrides,
+
+class FailureRecorder(CustomLogger):
+    def __init__(self) -> None:
+        super().__init__()
+        self.events: list[tuple[str, str]] = []
+
+    async def async_log_failure_event(
+        self, kwargs: dict[str, object], response_obj: object, start_time: datetime, end_time: datetime
+    ) -> None:
+        self.events.append(("failure", json.dumps(kwargs.get("standard_logging_object"), default=str)))
+
+    async def async_log_success_event(
+        self, kwargs: dict[str, object], response_obj: object, start_time: datetime, end_time: datetime
+    ) -> None:
+        self.events.append(("success", json.dumps(kwargs.get("standard_logging_object"), default=str)))
+
+    async def async_post_call_failure_hook(
+        self,
+        request_data: dict[str, object],
+        original_exception: Exception,
+        user_api_key_dict: UserAPIKeyAuth,
+        traceback_str: str | None = None,
+    ) -> None:
+        self.events.append(("post_failure", json.dumps(request_data, default=str)))
+
+
+@pytest.mark.asyncio
+@pytest.mark.usefixtures("proxy_mode")
+async def test_proxy_scope_exception_emits_failure_log(monkeypatch: pytest.MonkeyPatch) -> None:
+    recorder = FailureRecorder()
+    monkeypatch.setattr(litellm, "callbacks", [recorder])
+    auth = UserAPIKeyAuth(
+        api_key="scope-denial-key-hash",
+        object_permission=LiteLLM_ObjectPermissionTable(object_permission_id="denied", mcp_servers=["no-mcp-servers"]),
     )
+    arguments = {"tool_id": "denied-scope", "arguments": {}}
 
-
-def _upstream_tool(prefix: str, name: str) -> Tool:
-    return Tool(
-        name=f"{prefix}-{name}",
-        description=f"{name} numbers",
-        inputSchema={"type": "object", "properties": {"a": {"type": "integer"}}, "required": ["a"]},
-    )
-
-
-def _auth(**object_permission: object) -> UserAPIKeyAuth:
-    return UserAPIKeyAuth(
-        api_key="sk-scope",
-        object_permission=LiteLLM_ObjectPermissionTable(object_permission_id="scope", **object_permission),
-    )
-
-
-def _ids(result: CallToolResult) -> dict[str, str]:
-    return {item["name"]: item["tool_id"] for item in _text(result)}
-
-
-class TestMcpProxyAuthorizationScope:
-    """The real catalog resolver runs (server grants, tool grants, scope header, sentinel); only the
-    upstream tools/list fetch and the final upstream dispatch are faked."""
-
-    ALPHA = _server("srv-alpha", "alpha", tool_name_to_display_name={"add": "Add Numbers"})
-    BETA = _server("srv-beta", "beta")
-    ALPHA_ADD = with_mcp_proxy_identity(_upstream_tool("alpha", "add"), "srv-alpha")
-    ALPHA_MULTIPLY = with_mcp_proxy_identity(_upstream_tool("alpha", "multiply"), "srv-alpha")
-    BETA_ADD = with_mcp_proxy_identity(_upstream_tool("beta", "add"), "srv-beta")
-
-    @pytest.fixture
-    def rig(self) -> Iterator[AsyncMock]:
-        from litellm.proxy._experimental.mcp_server.mcp_server_manager import global_mcp_server_manager
-
-        upstream = {
-            "srv-alpha": [_upstream_tool("alpha", "add"), _upstream_tool("alpha", "multiply")],
-            "srv-beta": [_upstream_tool("beta", "add")],
-        }
-
-        async def fetch(server: MCPServer, **_: object) -> list[Tool]:
-            return list(upstream[server.server_id])
-
-        dispatched = AsyncMock(
-            return_value=CallToolResult(content=[TextContent(type="text", text="ok")], isError=False)
+    with pytest.raises(HTTPException) as denied:
+        await server._dispatch_virtual_mcp_tool(
+            name="call_tool",
+            arguments=arguments,
+            user_api_key_auth=auth,
+            client_ip=None,
+            mcp_servers=["ungranted"],
+            raw_headers={"authorization": "Bearer raw-scope-secret", "x-litellm-call-id": "scope-denial"},
         )
-        global_mcp_server_manager.registry.update({"srv-alpha": self.ALPHA, "srv-beta": self.BETA})
-        with (
-            patch.object(  # test-quality-ok: the upstream MCP server is the only faked collaborator
-                global_mcp_server_manager, "_get_tools_from_server", new=AsyncMock(side_effect=fetch)
-            ),
-            patch.object(global_mcp_server_manager, "call_tool", new=dispatched),  # test-quality-ok: dispatch seam
-        ):
-            yield dispatched
 
-    async def _proxy(
-        self, name: str, arguments: dict[str, object], auth: UserAPIKeyAuth, **kwargs: object
-    ) -> CallToolResult:
-        return await handle_mcp_proxy_tool(name, arguments, auth, **kwargs)
-
-    @pytest.mark.asyncio
-    async def test_search_and_schema_are_bounded_by_the_key_server_grant(self, rig: AsyncMock) -> None:
-        granted = _auth(mcp_servers=["srv-alpha"])
-
-        assert _ids(await self._proxy(MCP_PROXY_SEARCH_TOOL_NAME, {"query": "numbers"}, granted)) == {
-            "alpha-add": mcp_proxy_tool_id(self.ALPHA_ADD),
-            "alpha-multiply": mcp_proxy_tool_id(self.ALPHA_MULTIPLY),
-        }
-        denied_schema = await self._proxy(
-            MCP_PROXY_SCHEMA_TOOL_NAME, {"tool_id": mcp_proxy_tool_id(self.BETA_ADD)}, granted
-        )
-        denied_call = await self._proxy(
-            MCP_PROXY_CALL_TOOL_NAME, {"tool_id": mcp_proxy_tool_id(self.BETA_ADD), "arguments": {"a": 1}}, granted
-        )
-        assert denied_schema.isError is True and denied_call.isError is True
-        rig.assert_not_awaited()
-
-    @pytest.mark.asyncio
-    async def test_no_mcp_servers_sentinel_hides_every_tool(self, rig: AsyncMock) -> None:
-        result = await self._proxy(
-            MCP_PROXY_SEARCH_TOOL_NAME, {"query": "numbers"}, _auth(mcp_servers=["no-mcp-servers"])
-        )
-        assert _text(result) == []
-        rig.assert_not_awaited()
-
-    @pytest.mark.asyncio
-    async def test_tool_grant_hides_ungranted_tools_and_blocks_their_ids(self, rig: AsyncMock) -> None:
-        scoped = _auth(mcp_servers=["srv-alpha"], mcp_tool_permissions={"srv-alpha": ["add"]})
-
-        assert set(_ids(await self._proxy(MCP_PROXY_SEARCH_TOOL_NAME, {"query": "numbers"}, scoped))) == {"alpha-add"}
-        blocked = await self._proxy(
-            MCP_PROXY_CALL_TOOL_NAME, {"tool_id": mcp_proxy_tool_id(self.ALPHA_MULTIPLY), "arguments": {"a": 1}}, scoped
-        )
-        assert blocked.isError is True
-        rig.assert_not_awaited()
-
-    @pytest.mark.asyncio
-    async def test_same_named_tools_keep_distinct_ids_and_dispatch_to_their_own_server(self, rig: AsyncMock) -> None:
-        both = _auth(mcp_servers=["srv-alpha", "srv-beta"])
-
-        ids = _ids(await self._proxy(MCP_PROXY_SEARCH_TOOL_NAME, {"query": "add"}, both))
-        assert set(ids) == {"alpha-add", "beta-add"}, "display-name overrides must not rename proxy identities"
-        assert ids["alpha-add"] != ids["beta-add"]
-
-        result = await self._proxy(MCP_PROXY_CALL_TOOL_NAME, {"tool_id": ids["beta-add"], "arguments": {"a": 1}}, both)
-        assert result.isError is False
-        rig.assert_awaited_once()
-        assert rig.await_args.kwargs["server_name"] == "beta"
-        assert rig.await_args.kwargs["name"] == "add"
-
-    @pytest.mark.asyncio
-    async def test_server_scope_header_narrows_search_within_the_grant(self, rig: AsyncMock) -> None:
-        both = _auth(mcp_servers=["srv-alpha", "srv-beta"])
-        scoped = await self._proxy(MCP_PROXY_SEARCH_TOOL_NAME, {"query": "add"}, both, mcp_servers=["beta"])
-        assert set(_ids(scoped)) == {"beta-add"}
-        rig.assert_not_awaited()
+    assert denied.value.status_code == 403
+    assert denied.value.detail == {"error": "The key is not allowed to access the requested MCP servers: ungranted"}
+    assert [kind for kind, _ in recorder.events] == ["failure", "post_failure"]
+    payload = json.loads(recorder.events[0][1])
+    assert payload["id"] == "scope-denial"
+    assert payload["call_type"] == "call_mcp_tool"
+    assert payload["status"] == "failure"
+    assert payload["response_cost"] == 0
+    assert "ungranted" in payload["error_str"]
+    hook_payload = json.loads(recorder.events[1][1])
+    assert hook_payload["standard_logging_object"] == payload
+    assert hook_payload["arguments"] == arguments
+    assert "raw_headers" not in hook_payload
+    assert "raw-scope-secret" not in recorder.events[1][1]
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py
index 9b6eaba3177..7eb4396e60d 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server.py
@@ -3,6 +3,7 @@ import contextvars
 import os
 from datetime import datetime, timedelta
 from types import SimpleNamespace
+from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -1866,96 +1867,85 @@ async def test_streamable_http_session_manager_is_stateless():
 
 
 @pytest.mark.asyncio
-async def test_mcp_routing_initialize_to_stateful_no_session_to_stateless():
-    """
-    Test that routing correctly sends:
-    - initialize (no mcp-session-id) → stateful manager (so client gets mcp-session-id)
-    - tools/list (no mcp-session-id) → stateless manager (curl, Inspector)
-    """
-    try:
-        from litellm.proxy._experimental.mcp_server.server import (
-            handle_streamable_http_mcp,
-            session_manager_stateful,
-            session_manager_stateless,
+@pytest.mark.parametrize("debug", (False, True))
+@pytest.mark.parametrize(
+    ("method", "request_body", "stateful"),
+    (
+        ("POST", b'{"jsonrpc":"2.0","id":1,"method":"initialize","params":{}}', True),
+        ("POST", b'{"jsonrpc":"2.0","id":2,"method":"tools/list","params":{}}', False),
+        ("GET", b"", False),
+        ("DELETE", b"", False),
+    ),
+)
+async def test_mcp_routing_initialize_to_stateful_no_session_to_stateless(
+    debug: bool, method: str, request_body: bytes, stateful: bool
+) -> None:
+    from mcp.server.lowlevel.server import request_ctx
+    from mcp.shared.context import RequestContext
+    from starlette.requests import Request
+    from starlette.types import Message, Receive, Scope, Send
+
+    from litellm.proxy._experimental.mcp_server import server as mcp_module
+    from litellm.proxy._experimental.mcp_server.mcp_debug import record_auth_resolution
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.types import AuthResolution
+
+    scope: Final[Scope] = {"type": "http", "method": method, "path": "/mcp", "headers": []}
+    receive: Final = AsyncMock(return_value={"type": "http.request", "body": request_body, "more_body": False})
+    send: Final = AsyncMock()
+    observe_start: Final = AsyncMock()
+    body: Final[Message] = {"type": "http.response.body", "body": b"data: pong\n\n", "more_body": True}
+
+    async def handle_request(request_scope: Scope, receive: Receive, outgoing: Send) -> None:
+        await outgoing({"type": "http.response.start", "status": 200, "headers": []})
+        await observe_start(send.await_count)
+        context: Final = RequestContext(
+            request_id=1, meta=None, session=MagicMock(), lifespan_context=None, request=Request(request_scope)
         )
-    except ImportError:
-        pytest.skip("MCP server not available")
+        token: Final = request_ctx.set(context)
+        try:
+            record_auth_resolution("s1", AuthResolution.stored_user_token)
+        finally:
+            request_ctx.reset(token)
+        await outgoing(body)
 
-    async def make_request(method_body: bytes, path: str = "/mcp/progress_test"):
-        scope = {
-            "type": "http",
-            "method": "POST",
-            "path": path,
-            "headers": [
-                (b"content-type", b"application/json"),
-                (b"authorization", b"Bearer test-key"),
-            ],
-        }
-        receive = AsyncMock(
-            return_value={
-                "type": "http.request",
-                "body": method_body,
-                "more_body": False,
-            }
-        )
-        send = AsyncMock()
-
-        stateless_called = []
-        stateful_called = []
-
-        async def stateless_handle(s, r, se):
-            stateless_called.append(1)
-
-        async def stateful_handle(s, r, se):
-            stateful_called.append(1)
-
-        with (
-            patch(
-                "litellm.proxy._experimental.mcp_server.server.extract_mcp_auth_context",
-                new_callable=AsyncMock,
-                return_value=(MagicMock(), None, ["progress_test"], None, None, None),
+    stateless_handle: Final = AsyncMock(side_effect=handle_request)
+    stateful_handle: Final = AsyncMock(side_effect=handle_request)
+    with (
+        patch(
+            "litellm.proxy._experimental.mcp_server.server.extract_mcp_auth_context",
+            new_callable=AsyncMock,
+            return_value=(
+                UserAPIKeyAuth(user_id="debug-user"),
+                None,
+                None,
+                None,
+                None,
+                {"x-litellm-mcp-debug": "true"} if debug else {},
             ),
-            patch(
-                "litellm.proxy._experimental.mcp_server.server.set_auth_context",
-            ),
-            patch(
-                "litellm.proxy._experimental.mcp_server.server._SESSION_MANAGERS_INITIALIZED",
-                True,
-            ),
-            patch.object(
-                session_manager_stateless,
-                "handle_request",
-                side_effect=stateless_handle,
-            ),
-            patch.object(
-                session_manager_stateful,
-                "handle_request",
-                side_effect=stateful_handle,
-            ),
-            patch.object(
-                session_manager_stateless,
-                "_server_instances",
-                {},
-            ),
-            patch.object(
-                session_manager_stateful,
-                "_server_instances",
-                {},
-            ),
-        ):
-            await handle_streamable_http_mcp(scope, receive, send)
+        ),
+        patch("litellm.proxy._experimental.mcp_server.server._SESSION_MANAGERS_INITIALIZED", True),
+        patch(
+            "litellm.proxy._experimental.mcp_server.server.session_manager_stateless",
+            SimpleNamespace(handle_request=stateless_handle),
+        ),
+        patch(
+            "litellm.proxy._experimental.mcp_server.server.session_manager_stateful",
+            SimpleNamespace(handle_request=stateful_handle),
+        ),
+    ):
+        await mcp_module.handle_streamable_http_mcp(scope, receive, send)
 
-        return bool(stateless_called), bool(stateful_called)
-
-    # initialize → stateful
-    init_body = b'{"jsonrpc":"2.0","id":1,"method":"initialize","params":{"protocolVersion":"2024-11-05"}}'
-    stateless_called, stateful_called = await make_request(init_body)
-    assert stateful_called and not stateless_called, "initialize (no session) should route to stateful, not stateless"
-
-    # tools/list → stateless
-    tools_body = b'{"jsonrpc":"2.0","id":2,"method":"tools/list","params":{}}'
-    stateless_called, stateful_called = await make_request(tools_body)
-    assert stateless_called and not stateful_called, "tools/list (no session) should route to stateless, not stateful"
+    assert stateful_handle.await_count == (1 if stateful else 0)
+    assert stateless_handle.await_count == (0 if stateful else 1)
+    observe_start.assert_awaited_once_with(0 if debug and method == "POST" else 1)
+    assert send.await_count == 2
+    assert send.call_args_list[0].args[0]["status"] == 200
+    assert send.call_args_list[1].args[0] == body
+    headers: Final = dict(send.call_args_list[0].args[0]["headers"])
+    if debug:
+        assert headers[b"x-mcp-debug-auth-resolution"] == (b"stored-user-token" if method == "POST" else b"unresolved")
+    else:
+        assert not any(name.startswith(b"x-mcp-debug") for name in headers)
 
 
 @pytest.mark.asyncio
@@ -2013,6 +2003,11 @@ async def test_mcp_routing_chunked_initialize_to_stateful():
         patch(
             "litellm.proxy._experimental.mcp_server.server.set_auth_context",
         ),
+        patch(  # test-quality-ok: registry is empty in unit tests; key owns one server
+            "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+            new_callable=AsyncMock,
+            return_value=[MagicMock()],
+        ),
         patch(
             "litellm.proxy._experimental.mcp_server.server._SESSION_MANAGERS_INITIALIZED",
             True,
@@ -2498,6 +2493,11 @@ async def test_initialize_request_tracks_active_session_after_response_header():
                 new_callable=AsyncMock,
                 return_value=(owner_auth, None, None, None, None, None),
             ),
+            patch(  # test-quality-ok: registry is empty in unit tests; key owns one server
+                "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+                new_callable=AsyncMock,
+                return_value=[MagicMock()],
+            ),
             patch(
                 "litellm.proxy._experimental.mcp_server.server._SESSION_MANAGERS_INITIALIZED",
                 True,
@@ -2610,6 +2610,11 @@ async def test_initialize_request_with_existing_session_tracks_new_session():
                     {"x-new-header": "new"},
                 ),
             ),
+            patch(  # test-quality-ok: registry is empty in unit tests; key owns one server
+                "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+                new_callable=AsyncMock,
+                return_value=[MagicMock()],
+            ),
             patch(
                 "litellm.proxy._experimental.mcp_server.server._SESSION_MANAGERS_INITIALIZED",
                 True,
@@ -5624,6 +5629,78 @@ class TestGatewayCreateInitializationOptions:
 
         assert server.create_initialization_options().server_name == "litellm-mcp-server"
 
+    @pytest.mark.asyncio
+    async def test_initialize_with_no_granted_servers_returns_403(self):
+        from fastapi import HTTPException
+
+        from litellm.proxy._experimental.mcp_server.server import (
+            _gateway_initialize_instructions_request_scope,
+        )
+        from litellm.proxy._types import UserAPIKeyAuth
+
+        with patch(  # test-quality-ok: grant resolution is the input under test
+            "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+            new_callable=AsyncMock,
+            return_value=[],
+        ):
+            with pytest.raises(HTTPException) as exc_info:
+                async with _gateway_initialize_instructions_request_scope(
+                    user_api_key_auth=UserAPIKeyAuth(api_key="sk-no-mcp"),
+                    mcp_servers=None,
+                    client_ip=None,
+                    is_initialize=True,
+                ):
+                    pytest.fail("initialize must not proceed when the key grants no MCP servers")
+
+            assert exc_info.value.status_code == 403
+            assert "no MCP servers granted" in exc_info.value.detail["error"]
+
+    @pytest.mark.asyncio
+    async def test_initialize_with_no_granted_scoped_servers_returns_scoped_denial(self):
+        from fastapi import HTTPException
+
+        from litellm.proxy._experimental.mcp_server.server import (
+            _gateway_initialize_instructions_request_scope,
+        )
+        from litellm.proxy._types import UserAPIKeyAuth
+
+        with patch(  # test-quality-ok: grant resolution is the input under test
+            "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+            new_callable=AsyncMock,
+            return_value=[],
+        ):
+            with pytest.raises(HTTPException) as exc_info:
+                async with _gateway_initialize_instructions_request_scope(
+                    user_api_key_auth=UserAPIKeyAuth(api_key="sk-no-mcp"),
+                    mcp_servers=["grafana"],
+                    client_ip=None,
+                    is_initialize=True,
+                ):
+                    pytest.fail("scoped initialize must not proceed when nothing resolves")
+
+            assert exc_info.value.status_code == 403
+            assert "grafana" in exc_info.value.detail["error"]
+
+    @pytest.mark.asyncio
+    async def test_non_initialize_request_with_no_granted_servers_is_not_rejected_here(self):
+        from litellm.proxy._experimental.mcp_server.server import (
+            _gateway_initialize_instructions_request_scope,
+            _mcp_gateway_initialize_instructions,
+        )
+        from litellm.proxy._types import UserAPIKeyAuth
+
+        with patch(  # test-quality-ok: grant resolution is the input under test
+            "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+            new_callable=AsyncMock,
+            return_value=[],
+        ):
+            async with _gateway_initialize_instructions_request_scope(
+                user_api_key_auth=UserAPIKeyAuth(api_key="sk-no-mcp"),
+                mcp_servers=None,
+                client_ip=None,
+            ):
+                assert _mcp_gateway_initialize_instructions.get() is None
+
     @pytest.mark.asyncio
     async def test_sse_handler_scopes_server_name_from_single_server_path(self):
         try:
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server_manager.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server_manager.py
index 46fef83092d..a6e43686e2c 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server_manager.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_server_manager.py
@@ -5,7 +5,7 @@ import logging
 import os
 import sys
 from datetime import datetime
-from typing import Any, Dict, Final, Optional
+from typing import Any, Dict, Final, Literal, Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -4473,6 +4473,116 @@ class TestMCPServerManager:
         assert len(result) == 1
         assert result[0].name == "github_tool_1"
 
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("auth_type", [MCPAuth.none, MCPAuth.bearer_token, MCPAuth.api_key, MCPAuth.oauth2])
+    @pytest.mark.parametrize("is_byok", [False, True])
+    @pytest.mark.parametrize("scheme", ["http", "https"])
+    async def test_openapi_health_loads_spec_without_mcp_handshake(self, respx_mock, monkeypatch, auth_type, is_byok, scheme):
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        manager = MCPServerManager()
+        server = MCPServer(
+            server_id="openapi-health",
+            name="openapi-health",
+            transport=MCPTransport.http,
+            url="https://rest.example.com",
+            spec_path=f"{scheme}://93.184.216.34/openapi.json",
+            auth_type=auth_type,
+            is_byok=is_byok,
+            authentication_token=None if is_byok else "shared-secret",
+            static_headers={"Authorization": "Bearer static-secret"},
+        )
+        manager.registry = {server.server_id: server}
+        route = respx_mock.get(server.spec_path).respond(200, json={"openapi": "3.0.0", "paths": {}})
+        result = await manager.health_check_server(server.server_id, mcp_auth_header="caller-secret")
+        assert result.status == "healthy"
+        assert result.health_check_error is None
+        assert result.last_health_check is not None
+        assert result.spec_path == server.spec_path
+        assert route.call_count == 1
+        assert "authorization" not in route.calls[0].request.headers
+        assert "x-api-key" not in route.calls[0].request.headers
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("auth_type", [MCPAuth.none, MCPAuth.bearer_token])
+    @pytest.mark.parametrize("spec_path", ["/config/openapi.json", "relative/openapi.json"])
+    async def test_openapi_local_spec_health_is_unknown(self, respx_mock, auth_type, spec_path):
+        manager = MCPServerManager()
+        server = MCPServer(
+            server_id="local-openapi-health",
+            name="local-openapi-health",
+            transport=MCPTransport.http,
+            url="https://rest.example.com",
+            spec_path=spec_path,
+            auth_type=auth_type,
+            is_byok=True,
+        )
+        manager.registry = {server.server_id: server}
+        result = await manager.health_check_server(server.server_id)
+        assert result.status == "unknown"
+        assert result.health_check_error == "OpenAPI servers have no protocol-level health probe"
+        assert result.last_health_check is not None
+        assert not respx_mock.calls
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        ("failure", "expected_status", "expected_error"),
+        [
+            (httpx.Response(401, text="secret response content"), "unhealthy", "OpenAPI specification request failed (HTTP 401)"),
+            (httpx.Response(404), "unhealthy", "OpenAPI specification request failed (HTTP 404)"),
+            (httpx.Response(500), "unhealthy", "OpenAPI specification request failed (HTTP 500)"),
+            (httpx.ConnectError("secret network details"), "unhealthy", "OpenAPI specification could not be loaded (ConnectError)"),
+            (httpx.Response(200, text="secret invalid JSON body"), "unhealthy", "OpenAPI specification could not be loaded (JSONDecodeError)"),
+        ],
+    )
+    async def test_openapi_health_reports_safe_failures(self, respx_mock, monkeypatch, failure, expected_status, expected_error):
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        manager = MCPServerManager()
+        server = MCPServer(
+            server_id="failed-openapi-health",
+            name="failed-openapi-health",
+            transport=MCPTransport.http,
+            url="https://rest.example.com",
+            spec_path="https://93.184.216.34/key-secret?token=query-secret",
+            auth_type=MCPAuth.bearer_token,
+            is_byok=True,
+        )
+        manager.registry = {server.server_id: server}
+        route = respx_mock.get(server.spec_path).mock(side_effect=[failure])
+        result = await manager.health_check_server(server.server_id)
+        assert result.status == expected_status
+        assert result.health_check_error == expected_error
+        assert result.last_health_check is not None
+        assert route.call_count == 1
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("cancel", [False, True])
+    async def test_openapi_health_timeout_and_cancellation_cleanup(self, respx_mock, monkeypatch, cancel):
+        from litellm.proxy._experimental.mcp_server.mcp_server_manager import _openapi_spec_health
+
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        started = asyncio.Event()
+        cancelled = asyncio.Event()
+
+        async def slow_load(request):
+            started.set()
+            try:
+                await asyncio.Event().wait()
+            finally:
+                cancelled.set()
+
+        respx_mock.get("https://93.184.216.34/slow.json").mock(side_effect=slow_load)
+        task = asyncio.create_task(_openapi_spec_health("https://93.184.216.34/slow.json", timeout=0.1))
+        await asyncio.wait_for(started.wait(), timeout=1)
+        if cancel:
+            task.cancel()
+            with pytest.raises(asyncio.CancelledError):
+                await task
+        else:
+            status, error = await task
+            assert status == "unhealthy"
+            assert error == "OpenAPI specification check timed out after 0.1 seconds"
+        assert cancelled.is_set()
+
     @pytest.mark.asyncio
     async def test_health_check_server_healthy(self):
         """Test health check for a healthy server"""
@@ -12567,3 +12677,227 @@ async def test_pre_call_tool_check_honors_guardrail_attached_to_key(monkeypatch,
     with pytest.raises(HTTPException) as exc_info:
         await call
     assert exc_info.value.status_code == 400
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("config", "extra_headers", "expected_source", "expected_authorization"),
+    [
+        ("stored", None, "stored-user-token", "Bearer stored-token"),
+        ("stored", {"aUtHoRiZaTiOn": "Bearer injected"}, "stored-user-token", "Bearer stored-token"),
+        ("static", None, "static-token", "Bearer static-token"),
+        ("static", {"authorization": "Bearer injected"}, "extra-headers", "Bearer injected"),
+        ("none", None, "no-auth", None),
+        ("none", {"Authorization": "Bearer injected"}, "extra-headers", "Bearer injected"),
+    ],
+)
+async def test_debug_resolution_matches_final_header_conflict_winner(
+    config: Literal["stored", "static", "none"],
+    extra_headers: dict[str, str] | None,
+    expected_source: str,
+    expected_authorization: str | None,
+) -> None:
+    from mcp.server.lowlevel.server import request_ctx
+    from mcp.shared.context import RequestContext
+    from starlette.requests import Request
+    from pydantic import SecretStr
+
+    from litellm.proxy._experimental.mcp_server.auth.litellm_auth_handler import MCPAuthenticatedUser
+    from litellm.proxy._experimental.mcp_server.mcp_debug import MCP_AUTH_DIAGNOSTICS_SCOPE_KEY, MCPAuthDiagnostics
+    from litellm.proxy._experimental.mcp_server.outbound_credentials import (
+        ApiKeyConfig, AuthorizationCodeConfig, NoneConfig, ServerSpec, SharedKey, UpstreamCredentialProvider,
+    )
+    from litellm.proxy._experimental.mcp_server.outbound_credentials.oauth_token_store import OAuthToken
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    class Store:
+        def __init__(self) -> None:
+            self.calls = 0
+
+        async def fetch(self, user_id: str, server_id: str) -> OAuthToken | None:
+            self.calls += 1
+            return OAuthToken(access_token="stored-token") if user_id == "alice" else None
+
+    store = Store()
+    context = MCPAuthenticatedUser(UserAPIKeyAuth(user_id="alice"))
+    diagnostics = MCPAuthDiagnostics()
+    token = request_ctx.set(RequestContext(
+        request_id=1, meta=None, session=MagicMock(), lifespan_context=None,
+        request=Request({"type": "http", MCP_AUTH_DIAGNOSTICS_SCOPE_KEY: diagnostics}),
+    ))
+    selected = {
+        "stored": AuthorizationCodeConfig(),
+        "static": ApiKeyConfig(key_source=SharedKey(value=SecretStr("static-token"))),
+        "none": NoneConfig(),
+    }[config]
+    try:
+        auth, remaining = await MCPServerManager()._resolve_v2_auth(
+            server=MCPServer(
+                server_id="s", name="s", transport="http", url="https://up.example/mcp",
+                static_headers={"Authorization": "Bearer configured"},
+            ),
+            spec=ServerSpec(server_id="s", resource="https://up.example/mcp", config=selected),
+            provider=UpstreamCredentialProvider(oauth_token_store=store),
+            subject_token=None,
+            user_api_key_auth=context.user_api_key_auth,
+            extra_headers=extra_headers,
+        )
+        request = httpx.Request("GET", "https://up.example/mcp", headers=remaining)
+        if auth is not None:
+            next(auth.auth_flow(request))
+        assert diagnostics.resolution() == expected_source
+        assert request.headers.get("Authorization") == expected_authorization
+        assert store.calls == (1 if config == "stored" else 0)
+    finally:
+        request_ctx.reset(token)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("transport", ["http", "stdio"])
+async def test_debug_reports_legacy_signing_and_non_http_transport(transport: Literal["http", "stdio"]) -> None:
+    from mcp.server.lowlevel.server import request_ctx
+    from mcp.shared.context import RequestContext
+    from starlette.requests import Request
+
+    from litellm.proxy._experimental.mcp_server.mcp_debug import MCP_AUTH_DIAGNOSTICS_SCOPE_KEY, MCPAuthDiagnostics
+    from litellm.types.mcp_server.mcp_server_manager import MCPServer
+
+    diagnostics = MCPAuthDiagnostics()
+    token = request_ctx.set(RequestContext(
+        request_id=1, meta=None, session=MagicMock(), lifespan_context=None,
+        request=Request({"type": "http", MCP_AUTH_DIAGNOSTICS_SCOPE_KEY: diagnostics}),
+    ))
+    try:
+        server = MCPServer(
+            server_id="signed", name="signed", transport=transport,
+            url="https://up.example/mcp", auth_type="aws_sigv4",
+            aws_access_key_id="AKIDEXAMPLE", aws_secret_access_key="test-signing-secret",
+            aws_region_name="us-east-1", aws_service_name="execute-api",
+            command="python", args=["-c", "pass"],
+        )
+        client = await MCPServerManager()._create_mcp_client(server)
+        if transport == "stdio":
+            assert diagnostics.resolution() == "not-applicable"
+        else:
+            assert diagnostics.resolution() == "aws-sigv4"
+            request = httpx.Request("POST", "https://up.example/mcp", content=b"{}")
+            next(client._aws_auth.auth_flow(request))
+            assert request.headers["Authorization"].startswith("AWS4-HMAC-SHA256 ")
+            assert "Credential=AKIDEXAMPLE/" in request.headers["Authorization"]
+    finally:
+        request_ctx.reset(token)
+
+@pytest.mark.asyncio
+async def test_openapi_health_coalesces_concurrent_checks_and_reuses_results(respx_mock, monkeypatch):
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    manager = MCPServerManager()
+    server = MCPServer(
+        server_id="coalesced",
+        name="coalesced",
+        transport=MCPTransport.http,
+        spec_path="https://93.184.216.34/coalesced.json",
+        auth_type=MCPAuth.none,
+    )
+    manager.registry = {server.server_id: server}
+    started = asyncio.Event()
+    release = asyncio.Event()
+
+    async def serve(request):
+        started.set()
+        await release.wait()
+        return httpx.Response(200, json={"paths": {}})
+
+    route = respx_mock.get(server.spec_path).mock(side_effect=serve)
+    tasks = [asyncio.create_task(manager.health_check_server(server.server_id)) for _ in range(4)]
+    await asyncio.wait_for(started.wait(), timeout=1)
+    release.set()
+    results = await asyncio.gather(*tasks)
+    cached = await manager.health_check_server(server.server_id)
+    assert [result.status for result in results] == ["healthy"] * 4
+    assert cached.status == "healthy"
+    assert {result.last_health_check for result in [*results, cached]} == {results[0].last_health_check}
+    assert route.call_count == 1
+
+
+@pytest.mark.asyncio
+async def test_openapi_health_cache_expires_at_thirty_seconds(respx_mock, monkeypatch):
+    from litellm.proxy._experimental.mcp_server.mcp_server_manager import _OpenAPIHealthProbe
+
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    clock = iter([0.0, 29.0, 30.0, 30.0])
+    probe = _OpenAPIHealthProbe("https://93.184.216.34/expiry.json", clock=clock.__next__)
+    route = respx_mock.get(probe.spec_path).mock(
+        side_effect=[
+            httpx.Response(200, json={"paths": {}}),
+            httpx.Response(503),
+        ]
+    )
+    first = await probe.check()
+    assert first[0] == "healthy"
+    assert await probe.check() == first
+    refreshed = await probe.check()
+    assert refreshed[0] == "unhealthy"
+    assert refreshed[1] == "OpenAPI specification request failed (HTTP 503)"
+    assert refreshed[2] >= first[2]
+    assert route.call_count == 2
+
+
+@pytest.mark.asyncio
+async def test_openapi_health_reports_size_limit_as_unknown_and_caches_failure(respx_mock, monkeypatch):
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    manager = MCPServerManager()
+    server = MCPServer(
+        server_id="oversized",
+        name="oversized",
+        transport=MCPTransport.http,
+        spec_path="https://93.184.216.34/large.json",
+        auth_type=MCPAuth.none,
+    )
+    manager.registry = {server.server_id: server}
+    route = respx_mock.get(server.spec_path).respond(200, headers={"content-length": str(12 * 1024 * 1024)})
+    result = await manager.health_check_server(server.server_id)
+    cached = await manager.health_check_server(server.server_id)
+    assert result.status == "unknown"
+    assert result.health_check_error == "OpenAPI specification probe refused: Response exceeds the configured size limit"
+    assert cached.health_check_error == result.health_check_error
+    assert cached.last_health_check == result.last_health_check
+    assert route.call_count == 1
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("already_waiting", [False, True])
+async def test_openapi_health_cancellation_does_not_poison_cache(respx_mock, monkeypatch, already_waiting):
+    monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+    manager = MCPServerManager()
+    server = MCPServer(
+        server_id="cancelled-cache", name="cancelled-cache", transport=MCPTransport.http,
+        spec_path="https://93.184.216.34/cancelled-cache.json", auth_type=MCPAuth.none,
+    )
+    manager.registry = {server.server_id: server}
+    started = asyncio.Event()
+    attempts = []
+
+    async def serve(request):
+        attempts.append(request.url)
+        if not started.is_set():
+            started.set()
+            await asyncio.Event().wait()
+        return httpx.Response(200, json={"paths": {}})
+
+    route = respx_mock.get(server.spec_path).mock(side_effect=serve)
+    leader = asyncio.create_task(manager.health_check_server(server.server_id))
+    await asyncio.wait_for(started.wait(), timeout=1)
+    follower = asyncio.create_task(manager.health_check_server(server.server_id)) if already_waiting else None
+    await asyncio.sleep(0)
+    leader.cancel()
+    cancelled = await leader
+    assert cancelled.status == "unknown"
+    assert cancelled.health_check_error == "OpenAPI specification check was cancelled"
+    recovered = await follower if follower is not None else await manager.health_check_server(server.server_id)
+    assert recovered.status == "healthy"
+    assert recovered.health_check_error is None
+    cached = await manager.health_check_server(server.server_id)
+    assert cached.last_health_check == recovered.last_health_check
+    assert cached.status == "healthy"
+    assert len(attempts) == 2
+    assert route.call_count == 1
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_stale_session.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_stale_session.py
index feab179570b..9420eecd222 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_stale_session.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_mcp_stale_session.py
@@ -750,8 +750,7 @@ async def test_admitted_subject_missing_stored_token_challenged_with_resource_me
     challenge = exc_info.value.headers["www-authenticate"]
     assert "authorization_uri=" not in challenge
     assert challenge == (
-        'Bearer resource_metadata="http://localhost:8000'
-        '/.well-known/oauth-protected-resource/mcp/repro_oauth_server"'
+        'Bearer resource_metadata="http://localhost:8000/.well-known/oauth-protected-resource/mcp/repro_oauth_server"'
     )
 
 
@@ -938,6 +937,11 @@ async def test_handle_streamable_http_mcp_delegated_server_surfaces_upstream_cha
             "litellm.proxy._experimental.mcp_server.server.global_mcp_server_manager.get_mcp_server_by_name",
             return_value=delegated_server,
         ),
+        patch(  # test-quality-ok: registry is empty in unit tests; key owns the delegated server
+            "litellm.proxy._experimental.mcp_server.server._get_allowed_mcp_servers",
+            new_callable=AsyncMock,
+            return_value=[delegated_server],
+        ),
         patch.object(
             session_manager_stateful,
             "handle_request",
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_oauth_identity_binding.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_oauth_identity_binding.py
new file mode 100644
index 00000000000..0036035f448
--- /dev/null
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_oauth_identity_binding.py
@@ -0,0 +1,667 @@
+import time
+from collections.abc import Mapping
+from types import SimpleNamespace
+from typing import Final
+from unittest.mock import AsyncMock, MagicMock, patch
+
+import jwt
+import pytest
+from cryptography.hazmat.primitives import serialization
+from cryptography.hazmat.primitives.asymmetric import rsa
+from fastapi import HTTPException
+from pydantic import ValidationError
+
+from litellm.proxy._experimental.mcp_server.oauth_identity_binding import (
+    RefreshOwnershipProven,
+    RefreshTokenPresented,
+    VerifiedRefreshToken,
+    _discover_jwks_url,
+    _fetch_issuer_jwks,
+    _load_caller_principal,
+    _load_stored_refresh_token,
+    _select_signing_key,
+    current_binding_proof,
+    enforce_oauth_identity_binding,
+)
+from litellm.types.mcp import MCPAuth, MCPTransport
+from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+ISSUER: Final = "https://idp.example.com"
+AUDIENCE: Final = "litellm-client"
+KID: Final = "test-key"
+
+_PRIVATE_KEY: Final = rsa.generate_private_key(public_exponent=65537, key_size=2048)
+_PRIVATE_PEM: Final = _PRIVATE_KEY.private_bytes(
+    encoding=serialization.Encoding.PEM,
+    format=serialization.PrivateFormat.PKCS8,
+    encryption_algorithm=serialization.NoEncryption(),
+)
+_PUBLIC_JWK: Final = {
+    **jwt.algorithms.RSAAlgorithm.to_jwk(_PRIVATE_KEY.public_key(), as_dict=True),
+    "kid": KID,
+    "alg": "RS256",
+    "use": "sig",
+}
+
+
+def _sign_id_token(claims: Mapping[str, object]) -> str:
+    payload: Final = {
+        "iss": ISSUER,
+        "aud": AUDIENCE,
+        "exp": int(time.time()) + 300,
+        "iat": int(time.time()),
+        "nonce": "test-nonce",
+        "sub": "upstream-user",
+        **claims,
+    }
+    return jwt.encode(payload, _PRIVATE_PEM, algorithm="RS256", headers={"kid": KID})
+
+
+async def _jwks_fetcher(_binding: MCPOAuthIdentityBinding) -> list[Mapping[str, object]]:
+    return [_PUBLIC_JWK]
+
+
+def _caller_loader(email: str | None):
+    async def load(_user_id: str, _binding: MCPOAuthIdentityBinding) -> str | None:
+        return email
+
+    return load
+
+
+def _stored_refresh_token_loader(refresh_token: str | None):
+    async def load(_user_id: str, _server_id: str, _binding: MCPOAuthIdentityBinding) -> VerifiedRefreshToken | None:
+        return VerifiedRefreshToken(refresh_token, "verified-binding") if refresh_token else None
+
+    return load
+
+
+def _server(mode: str = "enforce", **binding_overrides: object) -> MCPServer:
+    return MCPServer(
+        server_id="srv-1",
+        name="srv-1",
+        url="https://mcp.example.com",
+        transport=MCPTransport.http,
+        auth_type=MCPAuth.oauth2,
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode=mode,
+            issuer=ISSUER,
+            audiences=[AUDIENCE],
+            **binding_overrides,
+        ),
+    )
+
+
+@pytest.mark.asyncio
+async def test_fetch_issuer_jwks_fetches_and_caches_keys():
+    binding: Final = _server(jwks_url="https://idp.example.com/jwks-cache").oauth_identity_binding
+    assert binding is not None
+    response: Final = MagicMock()
+    response.json.return_value = {"keys": [_PUBLIC_JWK]}
+    client: Final = MagicMock()
+    client.get = AsyncMock(return_value=response)
+
+    with patch(  # test-quality-ok: no HTTP dependency injection seam exists for JWKS fetching
+        "litellm.proxy._experimental.mcp_server.oauth_identity_binding.get_async_httpx_client",
+        return_value=client,
+    ):
+        first: Final = await _fetch_issuer_jwks(binding)
+        second: Final = await _fetch_issuer_jwks(binding)
+
+    assert first == second == [_PUBLIC_JWK]
+    client.get.assert_awaited_once_with("https://idp.example.com/jwks-cache")
+
+
+@pytest.mark.asyncio
+async def test_fetch_issuer_jwks_rejects_malformed_document():
+    binding: Final = _server(jwks_url="https://idp.example.com/jwks-invalid").oauth_identity_binding
+    assert binding is not None
+    response: Final = MagicMock()
+    response.json.return_value = {}
+    client: Final = MagicMock()
+    client.get = AsyncMock(return_value=response)
+
+    with patch(  # test-quality-ok: no HTTP dependency injection seam exists for JWKS fetching
+        "litellm.proxy._experimental.mcp_server.oauth_identity_binding.get_async_httpx_client",
+        return_value=client,
+    ):
+        with pytest.raises(TypeError, match="has no 'keys' array"):
+            await _fetch_issuer_jwks(binding)
+
+
+@pytest.mark.asyncio
+async def test_discover_jwks_url_returns_provider_uri():
+    response: Final = MagicMock()
+    response.json.return_value = {"jwks_uri": "https://idp.example.com/jwks"}
+    client: Final = MagicMock()
+    client.get = AsyncMock(return_value=response)
+
+    with patch(  # test-quality-ok: no HTTP dependency injection seam exists for OIDC discovery
+        "litellm.proxy._experimental.mcp_server.oauth_identity_binding.get_async_httpx_client",
+        return_value=client,
+    ):
+        result: Final = await _discover_jwks_url("https://idp.example.com/")
+
+    assert result == "https://idp.example.com/jwks"
+    client.get.assert_awaited_once_with("https://idp.example.com/.well-known/openid-configuration")
+
+
+@pytest.mark.asyncio
+async def test_discover_jwks_url_rejects_missing_provider_uri():
+    response: Final = MagicMock()
+    response.json.return_value = {}
+    client: Final = MagicMock()
+    client.get = AsyncMock(return_value=response)
+
+    with patch(  # test-quality-ok: no HTTP dependency injection seam exists for OIDC discovery
+        "litellm.proxy._experimental.mcp_server.oauth_identity_binding.get_async_httpx_client",
+        return_value=client,
+    ):
+        with pytest.raises(ValueError, match="returned no jwks_uri"):
+            await _discover_jwks_url("https://idp.example.com")
+
+
+def test_select_signing_key_returns_matching_key_or_rejection():
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": True})
+
+    selected: Final = _select_signing_key(token, [_PUBLIC_JWK])
+    rejected: Final = _select_signing_key(token, [])
+
+    assert selected.__class__.__name__ == "PyJWK"
+    assert rejected.code == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_load_caller_principal_supports_user_id_and_database_email():
+    user_id_binding: Final = _server(caller_field="user_id").oauth_identity_binding
+    assert user_id_binding is not None
+    assert await _load_caller_principal("user-a", user_id_binding) == "user-a"
+
+    with patch(  # test-quality-ok: caller loading is a lazy database boundary without injection
+        "litellm.proxy._experimental.mcp_server.bridge_token_flow.load_active_user_by_id",
+        new=AsyncMock(side_effect=["no_active_key", SimpleNamespace(user_email="alice@example.com")]),
+    ):
+        assert await _load_caller_principal("user-a", _server().oauth_identity_binding) is None
+        assert await _load_caller_principal("user-a", _server().oauth_identity_binding) == "alice@example.com"
+
+
+@pytest.mark.asyncio
+async def test_load_stored_refresh_token_returns_credential_and_fails_closed():
+    binding: Final = _server(caller_field="user_id", principal_claim="sub").oauth_identity_binding
+    proof: Final = await current_binding_proof(binding, "user-a", "srv-1")
+    get_credential: Final = AsyncMock(return_value={"refresh_token": "rt-1", "identity_binding_proof": proof})
+    with (
+        patch(  # test-quality-ok: stored-token loading is a lazy database boundary without injection
+            "litellm.proxy._experimental.mcp_server.db.get_user_oauth_credential",
+            new=get_credential,
+        ),
+        patch(  # test-quality-ok: stored-token loading is a lazy database boundary without injection
+            "litellm.proxy.utils.get_prisma_client_or_throw",
+            return_value="prisma",
+        ),
+    ):
+        assert await _load_stored_refresh_token("user-a", "srv-1", binding) == VerifiedRefreshToken("rt-1", proof)
+        get_credential.return_value = {"refresh_token": "rt-1"}
+        assert await _load_stored_refresh_token("user-a", "srv-1", binding) is None
+
+    with patch(  # test-quality-ok: stored-token loading is a lazy database boundary without injection
+        "litellm.proxy.utils.get_prisma_client_or_throw",
+        side_effect=RuntimeError("database unavailable"),
+    ):
+        assert await _load_stored_refresh_token("user-a", "srv-1", binding) is None
+
+
+@pytest.mark.asyncio
+async def test_matching_principal_passes():
+    token: Final = _sign_id_token({"email": "Alice@Example.com", "email_verified": True})
+    result: Final = await enforce_oauth_identity_binding(
+        server=_server(),
+        token_response={"access_token": "at", "id_token": token},
+        litellm_user_id="user-a",
+        grant_type="authorization_code",
+        expected_nonce="test-nonce",
+        refresh_ownership=None,
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader("alice@example.com"),
+    )
+    assert result is not None
+
+
+@pytest.mark.asyncio
+async def test_mismatched_principal_rejected():
+    token: Final = _sign_id_token({"email": "mallory@example.com", "email_verified": True})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_principal_mismatch"
+    assert exc_info.value.detail["credential_stored"] is False
+
+
+@pytest.mark.asyncio
+async def test_missing_upstream_principal_rejected():
+    token: Final = _sign_id_token({"email_verified": True})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+    assert "no usable" in exc_info.value.detail["error_description"]
+
+
+@pytest.mark.asyncio
+async def test_jwks_fetch_failure_is_rejected():
+    async def fail(_binding: MCPOAuthIdentityBinding) -> list[Mapping[str, object]]:
+        raise RuntimeError("jwks unavailable")
+
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": True})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=fail,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+    assert "jwks unavailable" in exc_info.value.detail["error_description"]
+
+
+@pytest.mark.asyncio
+async def test_missing_signing_key_is_rejected():
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": True})
+
+    async def no_keys(_binding: MCPOAuthIdentityBinding) -> tuple[Mapping[str, object], ...]:
+        return ()
+
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=no_keys,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+    assert "signing key" in exc_info.value.detail["error_description"]
+
+
+@pytest.mark.asyncio
+async def test_missing_caller_principal_is_rejected():
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": True})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader(None),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+    assert "has no" in exc_info.value.detail["error_description"]
+
+
+@pytest.mark.asyncio
+async def test_refresh_without_id_token_requires_litellm_identity_for_presented_token():
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at"},
+            litellm_user_id=None,
+            grant_type="refresh_token",
+            refresh_ownership=RefreshTokenPresented("rt-1"),
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+            stored_refresh_token_loader=_stored_refresh_token_loader("rt-1"),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+    assert "no resolvable LiteLLM user identity" in exc_info.value.detail["error_description"]
+
+
+@pytest.mark.asyncio
+async def test_user_id_principal_matching_uses_exact_comparison():
+    token: Final = _sign_id_token({"sub": "user-a"})
+    result: Final = await enforce_oauth_identity_binding(
+        server=_server(principal_claim="sub", caller_field="user_id"),
+        token_response={"access_token": "at", "id_token": token},
+        litellm_user_id="user-a",
+        grant_type="authorization_code",
+        expected_nonce="test-nonce",
+        refresh_ownership=None,
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader("user-a"),
+    )
+    assert result is not None
+
+
+@pytest.mark.asyncio
+async def test_missing_id_token_rejected_on_authorization_code():
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at"},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_refresh_without_id_token_allowed_when_presented_token_matches_stored_credential():
+    result: Final = await enforce_oauth_identity_binding(
+        server=_server(),
+        token_response={"access_token": "at"},
+        litellm_user_id="user-a",
+        grant_type="refresh_token",
+        refresh_ownership=RefreshTokenPresented("rt-1"),
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader("alice@example.com"),
+        stored_refresh_token_loader=_stored_refresh_token_loader("rt-1"),
+    )
+    assert result is not None
+
+
+@pytest.mark.asyncio
+async def test_refresh_without_id_token_rejects_different_presented_token():
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at"},
+            litellm_user_id="user-a",
+            grant_type="refresh_token",
+            refresh_ownership=RefreshTokenPresented("rt-stolen"),
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+            stored_refresh_token_loader=_stored_refresh_token_loader("rt-1"),
+        )
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_refresh_without_id_token_rejects_missing_stored_token():
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at"},
+            litellm_user_id="user-a",
+            grant_type="refresh_token",
+            refresh_ownership=RefreshTokenPresented("rt-1"),
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+            stored_refresh_token_loader=_stored_refresh_token_loader(None),
+        )
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_identity_envelope_does_not_prove_upstream_binding():
+    with pytest.raises(HTTPException) as error:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at"},
+            litellm_user_id="user-a",
+            grant_type="refresh_token",
+            refresh_ownership=RefreshOwnershipProven(),
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert error.value.status_code == 403
+
+
+@pytest.mark.asyncio
+async def test_refresh_without_id_token_rejects_without_ownership_proof():
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at"},
+            litellm_user_id="user-a",
+            grant_type="refresh_token",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+            stored_refresh_token_loader=_stored_refresh_token_loader("rt-1"),
+        )
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_refresh_with_mismatched_id_token_rejected():
+    token: Final = _sign_id_token({"email": "mallory@example.com", "email_verified": True})
+    with pytest.raises(HTTPException):
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="refresh_token",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+
+
+@pytest.mark.asyncio
+async def test_audit_mode_logs_but_does_not_reject(caplog):
+    token: Final = _sign_id_token({"email": "mallory@example.com", "email_verified": True})
+    result: Final = await enforce_oauth_identity_binding(
+        server=_server(mode="audit"),
+        token_response={"access_token": "at", "id_token": token},
+        litellm_user_id="user-a",
+        grant_type="authorization_code",
+        refresh_ownership=None,
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader("alice@example.com"),
+    )
+    assert result is None
+    assert "oauth_principal_mismatch" in caplog.text
+    assert "nonce" not in caplog.text
+
+
+@pytest.mark.asyncio
+async def test_unverified_email_rejected():
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": False})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_wrong_issuer_rejected():
+    payload: Final = {
+        "iss": "https://evil.example.com",
+        "aud": AUDIENCE,
+        "exp": int(time.time()) + 300,
+        "email": "alice@example.com",
+        "email_verified": True,
+    }
+    token: Final = jwt.encode(payload, _PRIVATE_PEM, algorithm="RS256", headers={"kid": KID})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_no_litellm_identity_rejected():
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": True})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id=None,
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.status_code == 403
+
+
+@pytest.mark.asyncio
+async def test_disabled_binding_is_noop():
+    result: Final = await enforce_oauth_identity_binding(
+        server=_server(mode="disabled"),
+        token_response={"access_token": "at"},
+        litellm_user_id=None,
+        grant_type="authorization_code",
+        expected_nonce="test-nonce",
+        refresh_ownership=None,
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader(None),
+    )
+    assert result is None
+
+
+@pytest.mark.asyncio
+async def test_no_binding_is_noop():
+    server: Final = MCPServer(
+        server_id="srv-2",
+        name="srv-2",
+        url="https://mcp.example.com",
+        transport=MCPTransport.http,
+    )
+    result: Final = await enforce_oauth_identity_binding(
+        server=server,
+        token_response={"access_token": "at"},
+        litellm_user_id=None,
+        grant_type="authorization_code",
+        expected_nonce="test-nonce",
+        refresh_ownership=None,
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader(None),
+    )
+    assert result is None
+
+
+def test_identity_binding_requires_non_empty_audiences():
+    with pytest.raises(ValidationError):
+        MCPOAuthIdentityBinding(mode="enforce", issuer=ISSUER, audiences=[])
+    with pytest.raises(ValidationError):
+        MCPOAuthIdentityBinding(mode="enforce", issuer=ISSUER)
+
+
+@pytest.mark.asyncio
+async def test_wrong_audience_rejected():
+    token: Final = _sign_id_token({"aud": "other-client", "email": "alice@example.com", "email_verified": True})
+    with pytest.raises(HTTPException) as exc_info:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            expected_nonce="test-nonce",
+            refresh_ownership=None,
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("nonce", [None, "another-login"])
+async def test_authorization_code_rejects_missing_or_foreign_nonce(nonce):
+    token = _sign_id_token({"email": "alice@example.com", "email_verified": True, "nonce": nonce})
+    with pytest.raises(HTTPException) as error:
+        await enforce_oauth_identity_binding(
+            server=_server(),
+            token_response={"access_token": "at", "id_token": token},
+            litellm_user_id="user-a",
+            grant_type="authorization_code",
+            refresh_ownership=None,
+            expected_nonce="this-login",
+            jwks_fetcher=_jwks_fetcher,
+            caller_principal_loader=_caller_loader("alice@example.com"),
+        )
+    assert error.value.status_code == 403
+    assert error.value.detail["error"] == "oauth_identity_binding_failed"
+
+
+@pytest.mark.asyncio
+async def test_binding_proof_rejects_changed_user_or_policy():
+    from litellm.proxy._experimental.mcp_server.oauth_identity_binding import credential_binding_matches
+
+    binding = _server(caller_field="user_id", principal_claim="sub").oauth_identity_binding
+    proof = await current_binding_proof(binding, "alice", "srv-1")
+    credential = {"identity_binding_proof": proof}
+    assert await credential_binding_matches(binding, "alice", "srv-1", credential)
+    assert not await credential_binding_matches(binding, "bob", "srv-1", credential)
+    assert not await credential_binding_matches(binding, "alice", "other-server", credential)
+    changed = binding.model_copy(update={"audiences": ["different-client"]})
+    assert not await credential_binding_matches(changed, "alice", "srv-1", credential)
+
+
+@pytest.mark.parametrize("auth_type", [MCPAuth.oauth_delegate, MCPAuth.true_passthrough])
+def test_identity_binding_rejects_modes_without_gateway_credential_custody(auth_type):
+    with pytest.raises(ValidationError, match="gateway-managed per-user"):
+        MCPServer(
+            server_id="srv",
+            name="srv",
+            transport=MCPTransport.http,
+            auth_type=auth_type,
+            oauth_identity_binding=_server().oauth_identity_binding,
+        )
+
+
+@pytest.mark.asyncio
+async def test_audit_matching_login_without_nonce_does_not_report_failure(caplog):
+    token: Final = _sign_id_token({"email": "alice@example.com", "email_verified": True})
+    result: Final = await enforce_oauth_identity_binding(
+        server=_server(mode="audit"),
+        token_response={"access_token": "at", "id_token": token},
+        litellm_user_id="user-a",
+        grant_type="authorization_code",
+        refresh_ownership=None,
+        jwks_fetcher=_jwks_fetcher,
+        caller_principal_loader=_caller_loader("alice@example.com"),
+    )
+    assert result is None
+    assert "oauth_identity_binding audit" not in caplog.text
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_openapi_to_mcp_generator.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_openapi_to_mcp_generator.py
index e59616e53c1..5fa202224e3 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_openapi_to_mcp_generator.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_openapi_to_mcp_generator.py
@@ -1378,3 +1378,83 @@ class TestUpstreamStatusIsClassified:
         assert exc.value.status_code == status_code
         assert secret_body not in str(exc.value)
         assert str(exc.value) == f"upstream returned HTTP {status_code}"
+
+class TestBoundedOpenAPISpecLoading:
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("max_bytes", [12, 13])
+    async def test_exact_size_and_smaller_specs_load(self, respx_mock, monkeypatch, max_bytes):
+        from litellm.proxy._experimental.mcp_server.openapi_to_mcp_generator import load_openapi_spec_async
+
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        route = respx_mock.get("https://93.184.216.34/spec.json").respond(200, content=b'{"paths":{}}')
+        assert await load_openapi_spec_async("https://93.184.216.34/spec.json", max_bytes=max_bytes) == {"paths": {}}
+        assert route.calls[0].request.headers["accept-encoding"] == "identity"
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("headers", [{"content-length": "1000000"}, {"content-encoding": "gzip"}])
+    async def test_unsafe_response_headers_reject_before_reading(self, respx_mock, monkeypatch, headers):
+        import httpx
+        from litellm.llms.custom_httpx.http_handler import HTTPResponseLimitError
+        from litellm.proxy._experimental.mcp_server.openapi_to_mcp_generator import (
+            load_openapi_spec_async,
+        )
+
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        closed = []
+
+        class UnreadableStream(httpx.AsyncByteStream):
+            async def __aiter__(self):
+                pytest.fail("Oversized or compressed response must not be consumed")
+                yield b""
+
+            async def aclose(self):
+                closed.append(True)
+
+        respx_mock.get("https://93.184.216.34/spec.json").respond(200, headers=headers, stream=UnreadableStream())
+        with pytest.raises(HTTPResponseLimitError):
+            await load_openapi_spec_async("https://93.184.216.34/spec.json", max_bytes=12)
+        assert closed == [True]
+
+    @pytest.mark.asyncio
+    async def test_chunked_response_is_bounded_and_closed(self, respx_mock, monkeypatch):
+        import httpx
+        from litellm.llms.custom_httpx.http_handler import HTTPResponseLimitError
+        from litellm.proxy._experimental.mcp_server.openapi_to_mcp_generator import (
+            load_openapi_spec_async,
+        )
+
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        consumed = []
+        closed = []
+
+        class ChunkedStream(httpx.AsyncByteStream):
+            async def __aiter__(self):
+                for index in range(10):
+                    consumed.append(index)
+                    yield b"x" * 65536
+
+            async def aclose(self):
+                closed.append(True)
+
+        respx_mock.get("https://93.184.216.34/spec.json").respond(200, stream=ChunkedStream())
+        with pytest.raises(HTTPResponseLimitError, match="size limit"):
+            await load_openapi_spec_async("https://93.184.216.34/spec.json", max_bytes=65536)
+        assert consumed == [0, 1]
+        assert closed == [True]
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("target", ["https://93.184.216.35/final.json", "http://127.0.0.1/private.json"])
+    async def test_bounded_spec_redirects_preserve_ssrf_protection(self, respx_mock, monkeypatch, target):
+        from litellm.litellm_core_utils.url_utils import SSRFError
+        from litellm.proxy._experimental.mcp_server.openapi_to_mcp_generator import load_openapi_spec_async
+
+        monkeypatch.setenv("DISABLE_AIOHTTP_TRANSPORT", "True")
+        respx_mock.get("https://93.184.216.34/spec.json").respond(302, headers={"location": target})
+        destination = respx_mock.get(target).respond(200, json={"paths": {}})
+        if "127.0.0.1" in target:
+            with pytest.raises(SSRFError):
+                await load_openapi_spec_async("https://93.184.216.34/spec.json", max_bytes=100)
+            assert not destination.called
+        else:
+            assert await load_openapi_spec_async("https://93.184.216.34/spec.json", max_bytes=100) == {"paths": {}}
+            assert destination.call_count == 1
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_rest_endpoints.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_rest_endpoints.py
index bd692776c82..16c6aa128d0 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_rest_endpoints.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_rest_endpoints.py
@@ -3,7 +3,7 @@ import inspect
 import json
 import sys
 from datetime import datetime
-from typing import Any, Dict, Optional
+from typing import Any, Dict, Final, Optional
 from unittest.mock import AsyncMock, MagicMock
 
 if sys.version_info < (3, 11):  # BaseExceptionGroup is a builtin only from 3.11
@@ -87,6 +87,125 @@ def _route_has_dependency(route, dependency) -> bool:
 
 
 class TestExecuteWithMcpClient:
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        ("auth_type", "auth_value", "expected_auth"),
+        (
+            (MCPAuth.none, None, {}),
+            (MCPAuth.basic, "preview:correct", {"Authorization": "Basic cHJldmlldzpjb3JyZWN0"}),
+            (MCPAuth.basic, None, {"Authorization": "Basic cHJldmlldzpzdG9yZWQ="}),
+            (MCPAuth.bearer_token, "edited", {"Authorization": "Bearer edited"}),
+            (MCPAuth.api_key, "edited", {"X-API-Key": "edited"}),
+            (MCPAuth.token, "edited", {"Authorization": "token edited"}),
+            (MCPAuth.authorization, "Custom edited", {"Authorization": "Custom edited"}),
+        ),
+    )
+    async def test_static_preview_uses_edited_connection_instead_of_registered_server(
+        self,
+        monkeypatch: pytest.MonkeyPatch,
+        auth_type: MCPAuth,
+        auth_value: str | None,
+        expected_auth: dict[str, str],
+    ) -> None:
+        from starlette.datastructures import Headers
+
+        from litellm.experimental_mcp_client.client import MCPClient
+        from litellm.proxy._experimental.mcp_server.mcp_server_manager import MCPServerManager
+        from litellm.proxy.management_endpoints import mcp_management_endpoints
+
+        saved: Final = MCPServer(
+            server_id="saved-preview-server",
+            name="saved",
+            url="https://stored.example/mcp",
+            transport=MCPTransport.http,
+            auth_type=MCPAuth.basic,
+            authentication_token="preview:stored",
+        )
+        manager: Final = MCPServerManager()
+        manager.registry = {saved.server_id: saved}
+        monkeypatch.setattr(rest_endpoints, "global_mcp_server_manager", manager)
+        monkeypatch.setattr(mcp_management_endpoints, "global_mcp_server_manager", manager)
+        payload: Final = NewMCPServerRequest(
+            server_id=saved.server_id,
+            server_name="edited",
+            url="https://stored.example/corrected-mcp",
+            transport=MCPTransport.sse,
+            auth_type=auth_type,
+            credentials={"auth_value": auth_value} if auth_value is not None else None,
+            static_headers={"X-Preview": "edited"},
+        )
+        staged: Final = rest_endpoints._stage_server_test(payload, Headers())
+
+        async def inspect_connection(client: MCPClient) -> dict[str, object]:
+            return {"url": client.server_url, "transport": client.transport_type, "headers": client._get_auth_headers()}
+
+        result: Final = await rest_endpoints._execute_with_mcp_client(
+            staged.request,
+            inspect_connection,
+            mcp_auth_header=staged.mcp_auth_header,
+            oauth2_headers=staged.oauth2_headers,
+        )
+        assert result == {
+            "url": "https://stored.example/corrected-mcp",
+            "transport": MCPTransport.sse,
+            "headers": {"X-Preview": "edited", **expected_auth},
+        }
+        assert manager.get_mcp_server_by_id(saved.server_id) is saved
+        assert saved.url == "https://stored.example/mcp"
+
+    @pytest.mark.parametrize(
+        ("saved_url", "url", "same_origin"),
+        (
+            ("https://stored.example/mcp", "https://other.example/mcp", False),
+            ("https://stored.example/mcp", "http://stored.example/mcp", False),
+            ("https://stored.example/mcp", "https://stored.example:8443/mcp", False),
+            ("https://stored.example/mcp", "https://stored.example:443/mcp", True),
+            ("http://stored.example/mcp", "http://stored.example:80/edited", True),
+            ("https://stored.example/mcp", "HTTPS://STORED.EXAMPLE/edited", True),
+            ("https://[::1]/mcp", "https://[::1]/edited", True),
+            ("https://[::1]/mcp", "https://[::1]:443/edited", True),
+            ("https://[::1]/mcp", "https://[::2]/edited", False),
+            ("https://stored.example/mcp", "https://stored.example:invalid/mcp", False),
+        ),
+    )
+    @pytest.mark.parametrize("explicit_credential", (None, "preview:explicit"))
+    def test_static_preview_respects_origin_when_inheriting_credentials(
+        self,
+        monkeypatch: pytest.MonkeyPatch,
+        saved_url: str,
+        url: str,
+        same_origin: bool,
+        explicit_credential: str | None,
+    ) -> None:
+        from starlette.datastructures import Headers
+
+        from litellm.proxy._experimental.mcp_server.mcp_server_manager import MCPServerManager
+        from litellm.proxy.management_endpoints import mcp_management_endpoints
+
+        saved: Final = MCPServer(
+            server_id="saved-preview-server",
+            name="saved",
+            url=saved_url,
+            transport=MCPTransport.http,
+            auth_type=MCPAuth.basic,
+            authentication_token="preview:stored",
+        )
+        manager: Final = MCPServerManager()
+        manager.registry = {saved.server_id: saved}
+        monkeypatch.setattr(rest_endpoints, "global_mcp_server_manager", manager)
+        monkeypatch.setattr(mcp_management_endpoints, "global_mcp_server_manager", manager)
+        payload: Final = NewMCPServerRequest(
+            server_id=saved.server_id,
+            url=url,
+            transport=MCPTransport.http,
+            auth_type=MCPAuth.basic,
+            credentials={"auth_value": explicit_credential} if explicit_credential else None,
+        )
+        staged: Final = rest_endpoints._stage_server_test(payload, Headers())
+        expected: Final = explicit_credential or ("preview:stored" if same_origin else None)
+        assert staged.mcp_auth_header == expected
+        assert staged.request.credentials == ({"auth_value": expected} if expected else None)
+
     @pytest.mark.asyncio
     async def test_redacts_stack_trace(self, monkeypatch):
         async def fake_create_client(*args, **kwargs):
@@ -113,7 +232,7 @@ class TestExecuteWithMcpClient:
         assert "stack_trace" not in result
 
     @pytest.mark.asyncio
-    async def test_timeout_caps_hanging_operation_and_names_url(self, monkeypatch):
+    async def test_timeout_caps_hanging_operation_and_names_origin(self, monkeypatch):
         async def fake_create_client(*args, **kwargs):
             return object()
 
@@ -138,7 +257,7 @@ class TestExecuteWithMcpClient:
         )
 
         assert result["error"] is True
-        assert "https://mcp.example.com/mcp/" in result["message"]
+        assert "https://mcp.example.com" in result["message"]
 
     @pytest.mark.asyncio
     async def test_timeout_covers_client_creation(self, monkeypatch):
@@ -166,15 +285,15 @@ class TestExecuteWithMcpClient:
         )
 
         assert result["error"] is True
-        assert "https://mcp.example.com/mcp/" in result["message"]
+        assert "https://mcp.example.com" in result["message"]
 
     def test_timeout_defaults_to_tool_listing_timeout(self):
         default = inspect.signature(rest_endpoints._execute_with_mcp_client).parameters["timeout_seconds"].default
         assert default == MCP_TOOL_LISTING_TIMEOUT
 
-    def test_connection_error_message_timeout_names_url_and_budget(self):
+    def test_connection_error_message_timeout_names_origin_and_budget(self):
         message = rest_endpoints._connection_error_message(TimeoutError(), "https://api.example.com/mcp/", 30.0)
-        assert "https://api.example.com/mcp/" in message
+        assert "https://api.example.com" in message
         assert "30s" in message
 
     def test_connection_error_message_hides_arbitrary_http_exception_detail(self):
@@ -592,7 +711,7 @@ class TestExecuteWithMcpClient:
 
         assert result["status"] == "error"
         assert result["error"] is True
-        assert "Failed to connect to MCP server" in result["message"]
+        assert "reference" in result["message"]
         # Error message must not leak raw exception details
         assert "cancel scope" not in result["message"]
 
@@ -3427,10 +3546,191 @@ class TestConnectionErrorMessage:
         message = rest_endpoints._connection_error_message(exc, "https://example.com", 30.0)
         assert "503" in message
 
+    @pytest.mark.parametrize(
+        "error_type", [httpx.ReadError, httpx.WriteError, httpx.RemoteProtocolError, ConnectionResetError]
+    )
+    def test_interrupted_connection_message_is_safe(self, error_type: type[Exception]) -> None:
+        message: Final = rest_endpoints._connection_error_message(
+            error_type("secret-transport-detail"), "https://example.com/?token=secret-query", 30
+        )
+        assert "connection was interrupted" in message
+        assert "secret" not in message
+
+    def test_closed_connection_explains_incomplete_request(self) -> None:
+        from mcp import McpError
+        from mcp.types import ErrorData
+
+        message: Final = rest_endpoints._connection_error_message(
+            McpError(ErrorData(code=-32000, message="Connection closed", data="secret-data")), None, 30
+        )
+        assert "connection was closed before the request completed" in message
+        assert "secret" not in message
+
+    def test_timeout_does_not_claim_the_server_sent_nothing(self) -> None:
+        message: Final = rest_endpoints._connection_error_message(TimeoutError(), None, 30)
+        assert "no valid MCP response received" in message
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("sdk_timeout", [True, False])
+    @pytest.mark.parametrize("read_timeout", [0, 1])
+    async def test_timeout_message_uses_the_deadline_that_expired(self, sdk_timeout: bool, read_timeout: int) -> None:
+        from mcp import McpError
+        from mcp.types import ErrorData
+
+        async def operation(client: rest_endpoints.MCPClient) -> dict[str, object]:
+            try:
+                raise TimeoutError("secret-timeout")
+            except TimeoutError as elapsed:
+                if not sdk_timeout:
+                    raise
+                try:
+                    raise McpError(ErrorData(code=408, message="secret-sdk-timeout")) from elapsed
+                except McpError as sdk_error:
+                    raise TimeoutError() from sdk_error
+
+        payload: Final = NewMCPServerRequest(
+            server_name="timeout", url="https://example.com", auth_type=MCPAuth.none, timeout=read_timeout
+        )
+        result: Final = await rest_endpoints._execute_with_mcp_client(payload, operation, timeout_seconds=30)
+        assert (f"within {read_timeout}s" if sdk_timeout else "within 30s") in result["message"]
+        assert "secret" not in result["message"]
+
     def test_unknown_error_falls_back_to_generic(self):
         message = rest_endpoints._connection_error_message(RuntimeError("weird"), "https://example.com", 30.0)
         assert "weird" not in message
-        assert "proxy logs" in message.lower()
+        assert "reference" in message.lower()
+
+    def test_sdk_session_terminated_explains_endpoint_and_retry(self) -> None:
+        from mcp.shared.exceptions import McpError
+        from mcp.types import ErrorData
+
+        message: Final = rest_endpoints._connection_error_message(
+            McpError(ErrorData(code=32600, message="Session terminated")), "https://example.com/mcp", 30.0
+        )
+
+        assert "session was terminated" in message
+        assert "MCP endpoint" in message
+        assert "transport" in message
+        assert "retry" in message
+        assert "404" not in message
+
+    @pytest.mark.parametrize("code", [-32700, -32601, -32602, -32603, -32000, 32600, 408])
+    def test_rpc_errors_include_code_without_echoing_upstream_data(self, code: int) -> None:
+        from mcp.shared.exceptions import McpError
+        from mcp.types import ErrorData
+
+        message: Final = rest_endpoints._connection_error_message(
+            McpError(ErrorData(code=code, message="secret-message", data={"token": "secret-data"})),
+            "https://example.com/secret-path?token=secret-query",
+            30.0,
+        )
+
+        assert f"JSON-RPC code {code}" in message
+        assert "secret" not in message
+        assert "timed out" not in message
+        assert "session was terminated" not in message
+
+    @pytest.mark.parametrize("status_code", [401, 403, 404, 405, 429, 503])
+    def test_wrapped_http_failures_preserve_status(self, status_code: int) -> None:
+        response: Final = httpx.Response(status_code, text="secret-body")
+        upstream: Final = httpx.HTTPStatusError(
+            "secret-exception",
+            request=httpx.Request("POST", "https://example.com/?token=secret-query"),
+            response=response,
+        )
+        wrapped: Final = BaseExceptionGroup(
+            "secret-group", [asyncio.CancelledError(), BaseExceptionGroup("nested", [upstream])]
+        )
+
+        message: Final = rest_endpoints._connection_error_message(wrapped, "https://example.com", 30.0)
+
+        assert f"HTTP {status_code}" in message
+        assert "secret" not in message
+
+    def test_explicit_cause_is_classified_before_incidental_context(self) -> None:
+        wrapped: Final = RuntimeError("secret-wrapper")
+        wrapped.__cause__ = httpx.ConnectError("secret-cause")
+        wrapped.__context__ = TimeoutError("secret-context")
+
+        message: Final = rest_endpoints._connection_error_message(wrapped, "https://example.com", 30.0)
+
+        assert "unreachable" in message
+        assert "secret" not in message
+
+    def test_timeout_url_redacts_credentials_path_query_and_fragment(self) -> None:
+        message: Final = rest_endpoints._connection_error_message(
+            TimeoutError("secret-error"),
+            "https://secret-user:secret-pass@example.com:8443/secret-path?token=secret-query#secret-fragment",
+            30.0,
+        )
+
+        assert "https://example.com:8443" in message
+        assert "30s" in message
+        assert "secret" not in message
+
+    def test_unknown_failure_reference_matches_safe_diagnostics(self, caplog: pytest.LogCaptureFixture) -> None:
+        import re
+
+        try:
+            raise RuntimeError("secret-exception-body")
+        except RuntimeError as exc:
+            message: Final = rest_endpoints._connection_error_message(
+                exc, "https://secret-user:secret-password@example.com/secret-path?token=secret-query", 30.0
+            )
+
+        reference: Final = re.search(r"reference ([a-f0-9]{32})", message)
+        assert reference is not None
+        diagnostics: Final = tuple(
+            record for record in caplog.records if "MCP connection test failed" in record.message
+        )
+        assert len(diagnostics) == 1
+        assert reference.group(1) in diagnostics[0].message
+        assert "RuntimeError" in diagnostics[0].message
+        assert "test_unknown_failure_reference_matches_safe_diagnostics" in diagnostics[0].message
+        assert diagnostics[0].exc_info is None
+        assert "secret" not in message + diagnostics[0].message
+
+    @pytest.mark.parametrize("exc", [ValueError("secret-config"), HTTPException(500, "secret-detail")])
+    def test_unrelated_errors_are_not_misreported_as_invalid_mcp(self, exc: Exception) -> None:
+        message: Final = rest_endpoints._connection_error_message(exc, "https://example.com", 30.0)
+
+        assert "reference" in message
+        assert "invalid MCP response" not in message
+        assert "secret" not in message
+
+    def test_configuration_validation_error_uses_unknown_fallback(self) -> None:
+        from pydantic import ValidationError
+
+        with pytest.raises(ValidationError) as caught:
+            NewMCPServerRequest.model_validate({"server_name": "example", "transport": "secret-invalid-transport"})
+
+        message: Final = rest_endpoints._connection_error_message(caught.value, "https://example.com", 30.0)
+        assert "reference" in message
+        assert "invalid MCP response" not in message
+        assert "secret" not in message
+
+    @pytest.mark.asyncio
+    async def test_connection_test_preserves_cancellation(self) -> None:
+        async def cancelled_operation(client: rest_endpoints.MCPClient) -> dict[str, object]:
+            raise asyncio.CancelledError
+
+        payload: Final = NewMCPServerRequest(server_name="cancelled", url="https://example.com", auth_type=MCPAuth.none)
+        with pytest.raises(asyncio.CancelledError):
+            await rest_endpoints._execute_with_mcp_client(payload, cancelled_operation)
+
+    @pytest.mark.asyncio
+    async def test_unknown_failure_preserves_response_contract(self) -> None:
+        async def failing_operation(client: rest_endpoints.MCPClient) -> dict[str, object]:
+            raise RuntimeError("secret-operation")
+
+        payload: Final = NewMCPServerRequest(server_name="unknown", url="https://example.com", auth_type=MCPAuth.none)
+        result: Final = await rest_endpoints._execute_with_mcp_client(payload, failing_operation)
+
+        assert result["error"] is True
+        assert result["status"] == "error"
+        assert "reference" in result["message"]
+        assert "secret" not in result["message"]
+        assert "stack_trace" not in result
 
 
 class TestGetServerAuthHeaderGroupDefault:
diff --git a/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_marketplace.py b/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_marketplace.py
index 99b09f48fe5..a585666743f 100644
--- a/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_marketplace.py
+++ b/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_marketplace.py
@@ -1,7 +1,7 @@
 """
 Unit tests for claude_code_marketplace.py source validation.
 
-Covers the git-subdir source type added alongside the existing github and url types.
+Covers the git-subdir and archive source types added alongside the existing github and url types.
 """
 
 import json
@@ -11,17 +11,20 @@ from fastapi import HTTPException
 from unittest.mock import AsyncMock, MagicMock
 
 import litellm
-from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy._types import LiteLLM_ObjectPermissionTable, ProxyException, UserAPIKeyAuth
 from litellm.proxy.proxy_server import LitellmUserRoles
 from litellm.types.proxy.claude_code_endpoints import (
     RegisterPluginRequest,
     UpdatePluginRequest,
 )
+from litellm.proxy.anthropic_endpoints.claude_code_endpoints import claude_code_marketplace
 from litellm.proxy.anthropic_endpoints.claude_code_endpoints.claude_code_marketplace import (
     delete_plugin,
     disable_plugin,
     enable_plugin,
     get_marketplace,
+    get_plugin,
+    list_plugins,
     register_plugin,
     update_plugin,
 )
@@ -38,11 +41,15 @@ def _make_mock_prisma():
     async def _find_unique(where):
         return store.get(where.get("name"))
 
+    def _matches(record, where) -> bool:
+        if "OR" in where:
+            return any(_matches(record, clause) for clause in where["OR"])
+        if "enabled" in where and record.enabled != where["enabled"]:
+            return False
+        return "name" not in where or record.name in where["name"]["in"]
+
     async def _find_many(where=None):
-        records = list(store.values())
-        if where and "enabled" in where:
-            return [r for r in records if r.enabled == where["enabled"]]
-        return records
+        return [r for r in store.values() if _matches(r, where or {})]
 
     async def _create(data):
         record = MagicMock()
@@ -52,6 +59,8 @@ def _make_mock_prisma():
         record.description = data.get("description")
         record.manifest_json = data.get("manifest_json", "{}")
         record.enabled = data.get("enabled", True)
+        record.created_at = data.get("created_at")
+        record.updated_at = data.get("updated_at")
         store[data["name"]] = record
         return record
 
@@ -87,6 +96,12 @@ _GIT_SUBDIR_SOURCE = {
     "path": "plugins/my-plugin",
 }
 
+_ARCHIVE_SOURCE = {
+    "source": "archive",
+    "url": "https://skills-bucket.s3.us-east-1.amazonaws.com/plugins/s3-skill-1.0.0.zip",
+    "sha256": "e3b0c44298fc1c149afbf4c8996fb92427ae41e4649b934ca495991b7852b855",
+}
+
 
 @pytest.fixture(autouse=True)
 def _patch_proxy_globals(monkeypatch):
@@ -265,13 +280,89 @@ async def test_get_marketplace_skips_plugin_with_null_manifest():
     table = litellm.proxy.proxy_server.prisma_client.db.litellm_claudecodeplugintable
     await table.create(data={"name": "null-manifest-plugin", "manifest_json": None, "enabled": True})
 
-    response = await get_marketplace()
+    response = await get_marketplace(request=MagicMock())
 
     assert response.status_code == 200
     body = json.loads(response.body)
     assert [plugin["name"] for plugin in body["plugins"]] == ["good-plugin"]
 
 
+def _granted_user(skills: list[str]) -> UserAPIKeyAuth:
+    return UserAPIKeyAuth(
+        user_role=LitellmUserRoles.INTERNAL_USER,
+        api_key="sk-granted",
+        user_id="granted-user",
+        object_permission=LiteLLM_ObjectPermissionTable(object_permission_id="perm-1", skills=skills),
+    )
+
+
+async def _register_public_and_private_plugins() -> None:
+    for name, enabled in (("public-skill", True), ("private-skill", False)):
+        await register_plugin(
+            request=RegisterPluginRequest(name=name, source=_GIT_SUBDIR_SOURCE, version="1.0.0"),
+            user_api_key_dict=_USER,
+        )
+        if not enabled:
+            await disable_plugin(plugin_name=name, user_api_key_dict=_USER)
+
+
+async def _listed_names(user: UserAPIKeyAuth) -> set[str]:
+    response = await list_plugins(user_api_key_dict=user)
+    return {plugin.name for plugin in response.plugins}
+
+
+@pytest.mark.asyncio
+async def test_list_plugins_shows_disabled_plugin_only_to_granted_key_or_admin():
+    await _register_public_and_private_plugins()
+
+    assert await _listed_names(_NON_ADMIN_USER) == {"public-skill"}
+    assert await _listed_names(_granted_user(["other-skill"])) == {"public-skill"}
+    assert await _listed_names(_granted_user(["private-skill"])) == {"public-skill", "private-skill"}
+    assert await _listed_names(_USER) == {"public-skill", "private-skill"}
+
+
+@pytest.mark.asyncio
+async def test_get_plugin_returns_403_for_disabled_plugin_the_key_is_not_granted():
+    await _register_public_and_private_plugins()
+
+    with pytest.raises(HTTPException) as exc_info:
+        await get_plugin(plugin_name="private-skill", user_api_key_dict=_NON_ADMIN_USER)
+    assert exc_info.value.status_code == 403
+
+    assert (await get_plugin(plugin_name="public-skill", user_api_key_dict=_NON_ADMIN_USER))["name"] == "public-skill"
+    granted = await get_plugin(plugin_name="private-skill", user_api_key_dict=_granted_user(["private-skill"]))
+    assert granted["name"] == "private-skill"
+    assert granted["enabled"] is False
+
+
+async def _marketplace_names(key: str | None) -> list[str]:
+    response = await get_marketplace(request=MagicMock(), key=key)
+    assert response.status_code == 200
+    return sorted(plugin["name"] for plugin in json.loads(response.body)["plugins"])
+
+
+@pytest.mark.asyncio
+async def test_get_marketplace_key_query_param_adds_granted_disabled_plugins(monkeypatch):
+    await _register_public_and_private_plugins()
+    keys = {"sk-granted": _granted_user(["private-skill"]), "sk-plain": _NON_ADMIN_USER}
+
+    async def _fake_auth(request, api_key: str) -> UserAPIKeyAuth:
+        token = api_key.removeprefix("Bearer ")
+        if token not in keys:
+            raise ProxyException(message="invalid key", type="auth_error", param="key", code=401)
+        return keys[token]
+
+    monkeypatch.setattr(claude_code_marketplace, "user_api_key_auth", _fake_auth)
+
+    assert await _marketplace_names(None) == ["public-skill"]
+    assert await _marketplace_names("sk-plain") == ["public-skill"]
+    assert await _marketplace_names("sk-granted") == ["private-skill", "public-skill"]
+
+    with pytest.raises(ProxyException) as exc_info:
+        await get_marketplace(request=MagicMock(), key="sk-bogus")
+    assert exc_info.value.code == "401"
+
+
 @pytest.mark.asyncio
 async def test_register_plugin_git_subdir_missing_url():
     """git-subdir without url field raises HTTP 400."""
@@ -377,6 +468,75 @@ async def test_register_plugin_unknown_source_type():
 
     assert exc_info.value.status_code == 400
     assert "git-subdir" in exc_info.value.detail["error"]
+    assert "archive" in exc_info.value.detail["error"]
+
+
+@pytest.mark.asyncio
+async def test_archive_source_registers_and_is_served_verbatim_in_marketplace():
+    response = await register_plugin(
+        request=RegisterPluginRequest(name="s3-skill", source=_ARCHIVE_SOURCE),
+        user_api_key_dict=_USER,
+    )
+
+    assert response.action == "created"
+    assert response.plugin.source == _ARCHIVE_SOURCE
+
+    marketplace = json.loads((await get_marketplace(request=MagicMock())).body)
+    assert marketplace["plugins"] == [{"name": "s3-skill", "source": _ARCHIVE_SOURCE, "version": "1.0.0"}]
+
+
+@pytest.mark.asyncio
+async def test_archive_source_without_sha256_is_accepted():
+    source = {"source": "archive", "url": "https://artifacts.example.com/plugin.zip"}
+
+    response = await register_plugin(
+        request=RegisterPluginRequest(name="unpinned-skill", source=source),
+        user_api_key_dict=_USER,
+    )
+
+    assert response.plugin.source == source
+
+
+@pytest.mark.asyncio
+async def test_update_plugin_to_archive_source():
+    name = "my-monorepo-plugin"
+    await register_plugin(
+        request=RegisterPluginRequest(name=name, source=_GIT_SUBDIR_SOURCE),
+        user_api_key_dict=_USER,
+    )
+
+    response = await update_plugin(
+        plugin_name=name,
+        request=UpdatePluginRequest(source=_ARCHIVE_SOURCE),
+        user_api_key_dict=_USER,
+    )
+
+    assert response.action == "updated"
+    assert (await _read_stored_manifest(name))["source"] == _ARCHIVE_SOURCE
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "source, expected_fragment",
+    [
+        ({"source": "archive"}, "url"),
+        ({"source": "archive", "url": ""}, "url"),
+        ({"source": "archive", "url": "http://artifacts.example.com/plugin.zip"}, "https"),
+        ({"source": "archive", "url": "s3://skills-bucket/plugin.zip"}, "https"),
+        ({"source": "archive", "url": "https://"}, "https"),
+        ({"source": "archive", "url": "https:///plugin.zip"}, "https"),
+        ({"source": "archive", "url": "https://[::1/plugin.zip"}, "https"),
+        ({"source": "archive", "url": "https://artifacts.example.com/plugin.zip", "sha256": "a" * 63}, "sha256"),
+        ({"source": "archive", "url": "https://artifacts.example.com/plugin.zip", "sha256": "a" * 65}, "sha256"),
+        ({"source": "archive", "url": "https://artifacts.example.com/plugin.zip", "sha256": "g" * 64}, "sha256"),
+    ],
+)
+async def test_register_plugin_archive_rejects_malformed_source(source, expected_fragment):
+    with pytest.raises(HTTPException) as exc_info:
+        await register_plugin(request=RegisterPluginRequest(name="bad-plugin", source=source), user_api_key_dict=_USER)
+
+    assert exc_info.value.status_code == 400
+    assert expected_fragment in exc_info.value.detail["error"]
 
 
 @pytest.mark.asyncio
diff --git a/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_skill_access.py b/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_skill_access.py
new file mode 100644
index 00000000000..dc4016d6db0
--- /dev/null
+++ b/tests/test_litellm/proxy/anthropic_endpoints/test_claude_code_skill_access.py
@@ -0,0 +1,79 @@
+"""Unit tests for claude_code_skill_access.py: key/team grant resolution."""
+
+from unittest.mock import MagicMock
+
+import pytest
+
+from litellm.proxy._types import LiteLLM_ObjectPermissionTable, LitellmUserRoles, UserAPIKeyAuth
+from litellm.proxy.anthropic_endpoints.claude_code_endpoints.claude_code_skill_access import (
+    granted_skills,
+    skill_visibility,
+)
+
+
+def _perm(skills: list[str] | None) -> LiteLLM_ObjectPermissionTable:
+    return LiteLLM_ObjectPermissionTable(object_permission_id="perm", skills=skills)
+
+
+def _key(key_skills: list[str] | None, team_skills: list[str] | None) -> UserAPIKeyAuth:
+    return UserAPIKeyAuth(
+        api_key="sk-user",
+        user_role=LitellmUserRoles.INTERNAL_USER,
+        object_permission=_perm(key_skills) if key_skills is not None else None,
+        team_object_permission=_perm(team_skills) if team_skills is not None else None,
+    )
+
+
+def _plugin(name: str, enabled: bool) -> MagicMock:
+    record = MagicMock()
+    record.name = name
+    record.enabled = enabled
+    return record
+
+
+@pytest.mark.parametrize(
+    ("key_skills", "team_skills", "expected"),
+    [
+        (None, None, frozenset()),
+        ([], [], frozenset()),
+        (["a", "b"], None, frozenset({"a", "b"})),
+        (None, ["a", "b"], frozenset({"a", "b"})),
+        (["a", "b"], ["b", "c"], frozenset({"b"})),
+        (["a"], ["c"], frozenset()),
+        (["a", "b"], [], frozenset({"a", "b"})),
+        ([], ["a", "b"], frozenset({"a", "b"})),
+    ],
+)
+def test_granted_skills_intersects_key_with_team(key_skills, team_skills, expected):
+    assert granted_skills(_key(key_skills, team_skills)) == expected
+
+
+def test_visibility_enabled_plugin_is_public_for_everyone():
+    public = _plugin("public-skill", enabled=True)
+
+    assert skill_visibility(None).allows(public)
+    assert skill_visibility(_key(None, None)).allows(public)
+    assert skill_visibility(_key([], ["other"])).allows(public)
+
+
+def test_visibility_disabled_plugin_needs_grant_or_admin():
+    private = _plugin("private-skill", enabled=False)
+    admin = UserAPIKeyAuth(api_key="sk-1234", user_role=LitellmUserRoles.PROXY_ADMIN)
+
+    assert not skill_visibility(None).allows(private)
+    assert not skill_visibility(_key(None, None)).allows(private)
+    assert not skill_visibility(_key(["other-skill"], None)).allows(private)
+    assert not skill_visibility(_key(["private-skill"], ["other-skill"])).allows(private)
+    assert skill_visibility(_key(["private-skill"], None)).allows(private)
+    assert skill_visibility(_key(None, ["private-skill"])).allows(private)
+    assert skill_visibility(admin).allows(private)
+
+
+def test_where_clause_bounds_the_plugin_query_to_what_the_caller_may_see():
+    admin = UserAPIKeyAuth(api_key="sk-1234", user_role=LitellmUserRoles.PROXY_ADMIN)
+
+    assert skill_visibility(None).where() == {"enabled": True}
+    assert skill_visibility(_key(None, None)).where() == {"enabled": True}
+    assert skill_visibility(_key(["b", "a"], None)).where() == {"OR": [{"enabled": True}, {"name": {"in": ["a", "b"]}}]}
+    assert skill_visibility(_key(["a", "b"], ["b"])).where() == {"OR": [{"enabled": True}, {"name": {"in": ["b"]}}]}
+    assert skill_visibility(admin).where() == {}
diff --git a/tests/test_litellm/proxy/auth/test_auth_checks.py b/tests/test_litellm/proxy/auth/test_auth_checks.py
index 2284a05b2e9..8777e24e209 100644
--- a/tests/test_litellm/proxy/auth/test_auth_checks.py
+++ b/tests/test_litellm/proxy/auth/test_auth_checks.py
@@ -1,7 +1,7 @@
 import asyncio
 import json
 from types import SimpleNamespace
-from typing import TYPE_CHECKING, Optional
+from typing import TYPE_CHECKING, Final, Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 if TYPE_CHECKING:
@@ -37,6 +37,7 @@ from litellm.proxy.auth.auth_checks import (
     _can_object_call_vector_stores,
     _check_end_user_budget,
     _check_team_member_budget,
+    _fetch_key_object_from_db_with_reconnect,
     _get_fuzzy_user_object,
     _get_team_db_check,
     _log_budget_lookup_failure,
@@ -55,6 +56,7 @@ from litellm.caching.redis_cache import RedisCache
 from litellm.constants import (
     DEFAULT_MANAGEMENT_OBJECT_IN_MEMORY_CACHE_TTL,
     END_USER_RESTRICTED_REGISTRY_MAX_SIZE,
+    PROXY_DB_LOOKUP_MAX_CONCURRENCY,
     REGISTRY_ERROR_NEGATIVE_CACHE_TTL,
     TAG_REGISTRY_MAX_SIZE,
 )
@@ -564,6 +566,43 @@ async def test_get_key_object_should_raise_if_reconnect_fails_on_db_connection_e
     assert mock_prisma_client.get_data.await_count == 1
 
 
+class _InFlightCountingPrisma:
+    def __init__(self) -> None:
+        self.in_flight = 0
+        self.max_in_flight = 0
+
+    async def get_data(
+        self, token: str, table_name: str, parent_otel_span: None, proxy_logging_obj: None
+    ) -> UserAPIKeyAuth:
+        self.in_flight += 1
+        self.max_in_flight = max(self.max_in_flight, self.in_flight)
+        await asyncio.sleep(0.001)
+        self.in_flight -= 1
+        return UserAPIKeyAuth(token=token)
+
+
+@pytest.mark.asyncio
+async def test_fetch_key_object_from_db_bounds_in_flight_prisma_requests():
+    prisma: Final = _InFlightCountingPrisma()
+    burst: Final = PROXY_DB_LOOKUP_MAX_CONCURRENCY * 5
+
+    results: Final = await asyncio.gather(
+        *(
+            _fetch_key_object_from_db_with_reconnect(
+                hashed_token=f"hashed-token-{i}",
+                prisma_client=prisma,  # pyright: ignore[reportArgumentType]  # fake stands in for PrismaClient
+                parent_otel_span=None,
+                proxy_logging_obj=None,
+            )
+            for i in range(burst)
+        )
+    )
+
+    assert len(results) == burst
+    assert {r.token for r in results if r is not None} == {f"hashed-token-{i}" for i in range(burst)}
+    assert prisma.max_in_flight == PROXY_DB_LOOKUP_MAX_CONCURRENCY
+
+
 def _fake_redis_cache():
     fake_redis = MagicMock()
     fake_redis.async_get_cache = AsyncMock(return_value=None)
@@ -2374,6 +2413,44 @@ def _mock_prisma_for_team_lookup(find_unique):
     return mock_prisma_client
 
 
+_TEAM_ALIAS_TABLE_ROW = {"id": 1, "model_aliases": '{"fast": "gpt-4o"}', "created_by": "admin", "updated_by": "admin"}
+
+
+def _prisma_team_row(include):
+    """Mimics Prisma: the `litellm_model_table` relation rides on the row only when the query `include`s it."""
+    columns = {"team_id": "team-aliases", "team_alias": "aliases", "models": ["gpt-4o"]}
+    row = (
+        {**columns, "litellm_model_table": _TEAM_ALIAS_TABLE_ROW}
+        if (include or {}).get("litellm_model_table")
+        else columns
+    )
+    return SimpleNamespace(dict=lambda: row, model_dump=lambda: row)
+
+
+@pytest.mark.asyncio
+async def test_get_team_object_loads_model_aliases_relation():
+    """LIT-5858: the auth path read teams without `include`ing `litellm_model_table`, so every JWT
+    team came back with `model_aliases=None` and alias requests 403'd."""
+    from litellm.proxy.auth.auth_checks import get_team_object
+    from litellm.proxy.auth.team_grants import team_model_aliases
+
+    async def find_unique(where, include=None):
+        return _prisma_team_row(include)
+
+    mock_cache = MagicMock()
+    mock_cache.async_get_cache = AsyncMock(return_value=None)
+    mock_cache.async_set_cache = AsyncMock()
+
+    team = await get_team_object(
+        team_id="team-aliases",
+        prisma_client=_mock_prisma_for_team_lookup(AsyncMock(side_effect=find_unique)),
+        user_api_key_cache=mock_cache,
+        check_db_only=True,
+    )
+
+    assert team_model_aliases(team) == {"fast": "gpt-4o"}
+
+
 @pytest.mark.asyncio
 async def test_get_team_object_distinguishes_absent_team_from_unreadable_row():
     """A deleted team and a database that would not answer both surface as a 404,
@@ -6195,6 +6272,32 @@ async def test_get_team_object_by_alias_db_fetch_returns_cached_obj():
     assert result.models == ["gpt-4"]
 
 
+@pytest.mark.asyncio
+async def test_get_team_object_by_alias_loads_model_aliases_relation():
+    """LIT-5858: same regression as `test_get_team_object_loads_model_aliases_relation`, for the
+    `team_alias_jwt_field` lookup."""
+    from litellm.proxy.auth.auth_checks import get_team_object_by_alias
+    from litellm.proxy.auth.team_grants import team_model_aliases
+
+    async def find_many(where, include=None):
+        return [_prisma_team_row(include)]
+
+    mock_prisma_client = MagicMock()
+    mock_prisma_client.db.litellm_teamtable.find_many = AsyncMock(side_effect=find_many)
+
+    mock_cache = MagicMock()
+    mock_cache.async_get_cache = AsyncMock(return_value=None)
+    mock_cache.async_set_cache = AsyncMock()
+
+    team = await get_team_object_by_alias(
+        team_alias="aliases",
+        prisma_client=mock_prisma_client,
+        user_api_key_cache=mock_cache,
+    )
+
+    assert team_model_aliases(team) == {"fast": "gpt-4o"}
+
+
 @pytest.mark.asyncio
 async def test_get_org_object_by_alias_db_fetch_returns_validated_org():
     from litellm.proxy._types import LiteLLM_OrganizationTable
diff --git a/tests/test_litellm/proxy/auth/test_auth_utils.py b/tests/test_litellm/proxy/auth/test_auth_utils.py
index aaf630ad29b..cdf1f897707 100644
--- a/tests/test_litellm/proxy/auth/test_auth_utils.py
+++ b/tests/test_litellm/proxy/auth/test_auth_utils.py
@@ -565,6 +565,38 @@ def test_get_model_from_request_bedrock_unparseable_endpoint_keeps_body_model():
     )
 
 
+def _azure_relay_router():
+    from litellm.router import Router
+
+    return Router(
+        model_list=[
+            {
+                "model_name": "gpt",
+                "litellm_params": {"model": "azure_ai/gpt-5.4-mini", "api_base": "https://a.services.ai.azure.com", "api_key": "k"},
+            },
+            {
+                "model_name": "other-group",
+                "litellm_params": {"model": "azure/gpt-5.4", "api_base": "https://b.openai.azure.com", "api_key": "k"},
+            },
+        ]
+    )
+
+
+@pytest.mark.parametrize(
+    "route, request_data, expected",
+    [
+        ("/azure_ai/other-group/openai/deployments/other-group/chat/completions", {"model": "gpt"}, "other-group"),
+        ("/azure_ai/other-group/models/chat/completions", {}, "other-group"),
+        ("/azure/openai/deployments/gpt/chat/completions", {"model": "other-group"}, "gpt"),
+        ("/azure/openai/deployments/gpt/chat/completions", {}, "gpt"),
+        ("/azure/openai/deployments/my-azure-deployment/chat/completions", {"model": "gpt"}, "gpt"),
+        ("/azure_ai/gpt", {"model": "other-group"}, "other-group"),
+    ],
+)
+def test_get_model_from_request_azure_relay_routes_use_the_model_group_in_the_path(route, request_data, expected):
+    assert get_model_from_request(request_data=request_data, route=route, llm_router=_azure_relay_router()) == expected
+
+
 def test_get_model_from_request_includes_file_endpoint_header_model():
     assert (
         get_model_from_request(
@@ -3497,7 +3529,7 @@ class TestIsRequestBodySafeBlocksAwsIdentitySelectors:
 
     @pytest.mark.parametrize(
         "selector",
-        ["aws_profile_name", "aws_session_name", "aws_external_id"],
+        ["aws_profile_name", "aws_session_name", "aws_external_id", "aws_session_tags"],
     )
     def test_aws_identity_selector_in_batch_body_is_rejected(self, selector):
         with pytest.raises(ValueError, match=selector):
@@ -3516,7 +3548,7 @@ class TestIsRequestBodySafeBlocksAwsIdentitySelectors:
 
     @pytest.mark.parametrize(
         "selector",
-        ["aws_profile_name", "aws_session_name", "aws_external_id"],
+        ["aws_profile_name", "aws_session_name", "aws_external_id", "aws_session_tags"],
     )
     def test_aws_identity_selector_under_extra_body_is_rejected(self, selector):
         with pytest.raises(ValueError, match=selector):
diff --git a/tests/test_litellm/proxy/auth/test_handle_jwt.py b/tests/test_litellm/proxy/auth/test_handle_jwt.py
index 99a0a4c0a8b..94226b5404d 100644
--- a/tests/test_litellm/proxy/auth/test_handle_jwt.py
+++ b/tests/test_litellm/proxy/auth/test_handle_jwt.py
@@ -13,6 +13,7 @@ from litellm.proxy._types import (
     DEFAULT_JWKS_STALE_TTL,
     JWTLiteLLMRoleMap,
     LiteLLM_JWTAuth,
+    LiteLLM_ModelTable,
     LiteLLM_TeamMembership,
     LiteLLM_TeamTable,
     LiteLLM_UserTable,
@@ -1255,6 +1256,57 @@ async def test_find_team_with_model_access_model_group(monkeypatch):
     assert team_obj.team_id == "team-1"
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "model_aliases",
+    ['{"fast": "gpt-4o"}', {"fast": "gpt-4o"}],
+    ids=["json-string", "dict"],
+)
+async def test_find_team_with_model_access_resolves_team_model_alias(monkeypatch, model_aliases):
+    """LIT-5858: a JWT team that grants `gpt-4o` under the alias `fast` must resolve a request
+    for `fast`. The JWT path used to pass `team_model_aliases=None`, so every alias request 403'd."""
+    import sys
+    import types
+
+    from litellm.caching import DualCache
+    from litellm.proxy.utils import ProxyLogging
+    from litellm.router import Router
+
+    router = Router(model_list=[{"model_name": "gpt-4o", "litellm_params": {"model": "gpt-4o"}}])
+    proxy_server_module = types.ModuleType("proxy_server")
+    proxy_server_module.llm_router = router
+    monkeypatch.setitem(sys.modules, "litellm.proxy.proxy_server", proxy_server_module)
+
+    team = LiteLLM_TeamTable(
+        team_id="team-aliases",
+        models=["gpt-4o"],
+        litellm_model_table=LiteLLM_ModelTable(model_aliases=model_aliases, created_by="admin", updated_by="admin"),
+    )
+
+    async def mock_get_team_object(*args, **kwargs):
+        return team
+
+    monkeypatch.setattr("litellm.proxy.auth.handle_jwt.get_team_object", mock_get_team_object)
+
+    jwt_handler = JWTHandler()
+    jwt_handler.litellm_jwtauth = LiteLLM_JWTAuth()
+    user_api_key_cache = DualCache()
+
+    team_id, team_obj = await JWTAuthManager.find_team_with_model_access(
+        team_ids={"team-aliases"},
+        requested_model="fast",
+        route="/chat/completions",
+        jwt_handler=jwt_handler,
+        prisma_client=None,
+        user_api_key_cache=user_api_key_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=ProxyLogging(user_api_key_cache=user_api_key_cache),
+    )
+
+    assert team_id == "team-aliases"
+    assert team_obj is team
+
+
 @pytest.mark.asyncio
 async def test_find_team_with_model_access_v1_messages_default_routes(monkeypatch):
     """Regression for #31189: a single-team JWT that grants the requested model
diff --git a/tests/test_litellm/proxy/auth/test_login_utils.py b/tests/test_litellm/proxy/auth/test_login_utils.py
index 8d93d801bfd..e209a491b0a 100644
--- a/tests/test_litellm/proxy/auth/test_login_utils.py
+++ b/tests/test_litellm/proxy/auth/test_login_utils.py
@@ -23,6 +23,7 @@ from litellm.proxy.auth.login_utils import (
     LoginResult,
     authenticate_user,
     get_ui_credentials,
+    is_env_credential_login_enabled,
 )
 
 
@@ -185,6 +186,7 @@ async def test_authenticate_user_invalid_credentials():
         assert exc_info.value.type == ProxyErrorTypes.auth_error
         assert exc_info.value.code == "401"
         assert "Invalid credentials" in exc_info.value.message
+        assert "UI_USERNAME" in exc_info.value.message
 
 
 @pytest.mark.asyncio
@@ -799,3 +801,158 @@ class TestDisablePasswordLoginWhenSSOEnabled:
 
         assert isinstance(result, LoginResult)
         assert result.user_id == LITELLM_PROXY_ADMIN_NAME
+
+
+class TestDisableEnvCredentialLogin:
+    """`disable_env_credential_login` must reject a login with the env
+    credentials (UI_USERNAME/UI_PASSWORD, or the master-key fallback when
+    UI_PASSWORD is unset) while leaving database-user password logins
+    untouched, so admins with real accounts keep a way in."""
+
+    @pytest.mark.asyncio
+    async def test_rejects_correct_env_credentials_when_disabled(self):
+        master_key = "sk-1234"
+        ui_username = "admin"
+        ui_password = "env-only-password"
+
+        mock_prisma_client = MagicMock()
+        mock_prisma_client.db.litellm_usertable.find_first = AsyncMock(return_value=None)
+
+        with patch.dict(os.environ, {"UI_USERNAME": ui_username, "UI_PASSWORD": ui_password}):
+            with pytest.raises(ProxyException) as exc_info:
+                await authenticate_user(
+                    username=ui_username,
+                    password=ui_password,
+                    master_key=master_key,
+                    prisma_client=mock_prisma_client,
+                    general_settings={"disable_env_credential_login": True},
+                )
+
+        assert exc_info.value.type == ProxyErrorTypes.auth_error
+        assert exc_info.value.code == "401"
+        assert "UI_USERNAME" not in exc_info.value.message
+        assert "UI_PASSWORD" not in exc_info.value.message
+
+    @pytest.mark.asyncio
+    async def test_rejects_master_key_fallback_when_disabled(self):
+        """With UI_PASSWORD unset, the master key IS the env password, so the
+        setting must reject it too or it protects nothing by default."""
+        master_key = "sk-1234"
+
+        mock_prisma_client = MagicMock()
+        mock_prisma_client.db.litellm_usertable.find_first = AsyncMock(return_value=None)
+
+        with patch.dict(os.environ, {"UI_USERNAME": "admin"}, clear=True):
+            with pytest.raises(ProxyException) as exc_info:
+                await authenticate_user(
+                    username="admin",
+                    password=master_key,
+                    master_key=master_key,
+                    prisma_client=mock_prisma_client,
+                    general_settings={"disable_env_credential_login": True},
+                )
+
+        assert exc_info.value.code == "401"
+
+    @pytest.mark.asyncio
+    async def test_db_user_login_still_works_when_disabled(self):
+        master_key = "sk-1234"
+        user_email = "admin@example.com"
+        password = "Str0ng!Passw0rd"
+
+        mock_user = LiteLLM_UserTable(
+            user_id="db-admin-1",
+            user_email=user_email,
+            password=hash_token(token=password),
+            user_role=LitellmUserRoles.PROXY_ADMIN,
+        )
+        mock_prisma_client = MagicMock()
+        mock_prisma_client.db.litellm_usertable.find_first = AsyncMock(return_value=mock_user)
+
+        with patch.dict(
+            os.environ,
+            {
+                "UI_USERNAME": "admin",
+                "UI_PASSWORD": "env-password",
+                "DATABASE_URL": "postgresql://test:test@localhost/test",
+            },
+            clear=True,
+        ):
+            with ExitStack() as stack:
+                stack.enter_context(
+                    patch(  # test-quality-ok: internal orchestration, no HTTP boundary; matches pre-existing tests
+                        "litellm.proxy.auth.login_utils.generate_key_helper_fn",
+                        new_callable=AsyncMock,
+                        return_value={"token": "db-user-token"},
+                    )
+                )
+                result = await authenticate_user(
+                    username=user_email,
+                    password=password,
+                    master_key=master_key,
+                    prisma_client=mock_prisma_client,
+                    general_settings={"disable_env_credential_login": True},
+                )
+
+        assert isinstance(result, LoginResult)
+        assert result.user_id == "db-admin-1"
+        assert result.user_role == LitellmUserRoles.PROXY_ADMIN
+
+    @pytest.mark.asyncio
+    async def test_env_login_still_works_when_setting_absent(self):
+        """Env-credential login is the bootstrap path on a fresh install and
+        must stay on by default."""
+        master_key = "sk-1234"
+        ui_username = "admin"
+
+        mock_prisma_client = MagicMock()
+        mock_prisma_client.db.litellm_usertable.find_first = AsyncMock(return_value=None)
+
+        with patch.dict(
+            os.environ,
+            {
+                "UI_USERNAME": ui_username,
+                "UI_PASSWORD": master_key,
+                "DATABASE_URL": "postgresql://test:test@localhost/test",
+            },
+            clear=True,
+        ):
+            with ExitStack() as stack:
+                _patch_successful_admin_login_deps(stack)
+                result = await authenticate_user(
+                    username=ui_username,
+                    password=master_key,
+                    master_key=master_key,
+                    prisma_client=mock_prisma_client,
+                    general_settings={},
+                )
+
+        assert isinstance(result, LoginResult)
+        assert result.user_id == LITELLM_PROXY_ADMIN_NAME
+
+
+class TestIsEnvCredentialLoginEnabled:
+    """Drives the Admin UI warning banner: it must be True exactly when a
+    login with the env credentials could actually succeed."""
+
+    def test_enabled_by_default(self):
+        assert is_env_credential_login_enabled({}) is True
+
+    def test_disabled_by_dedicated_setting(self):
+        assert is_env_credential_login_enabled({"disable_env_credential_login": True}) is False
+
+    def test_explicit_false_keeps_it_enabled(self):
+        assert is_env_credential_login_enabled({"disable_env_credential_login": False}) is True
+
+    def test_disabled_when_sso_gate_blocks_all_password_logins(self):
+        """`disable_password_login_when_sso_enabled` with SSO configured
+        rejects every username/password login before the env comparison runs,
+        so the banner must not nag about an already-unreachable path."""
+        with ExitStack() as stack:
+            _patch_sso_configured(stack, configured=True)
+            assert is_env_credential_login_enabled({"disable_password_login_when_sso_enabled": True}) is False
+
+    def test_enabled_when_sso_gate_is_set_but_sso_not_configured(self):
+        with ExitStack() as stack:
+            _patch_sso_configured(stack, configured=False)
+            assert is_env_credential_login_enabled({"disable_password_login_when_sso_enabled": True}) is True
diff --git a/tests/test_litellm/proxy/auth/test_route_checks.py b/tests/test_litellm/proxy/auth/test_route_checks.py
index 0fd19f518d9..38a0e85c1ea 100644
--- a/tests/test_litellm/proxy/auth/test_route_checks.py
+++ b/tests/test_litellm/proxy/auth/test_route_checks.py
@@ -2033,6 +2033,82 @@ def test_proxy_admin_viewer_can_access_logs_page_endpoints(route):
         )
 
 
+@pytest.mark.parametrize(
+    "user_role",
+    [LitellmUserRoles.INTERNAL_USER, LitellmUserRoles.INTERNAL_USER_VIEW_ONLY],
+)
+def test_internal_user_can_access_logs_drawer_detail_route(user_role):
+    """
+    The Logs drawer detail fetch (GET /spend/logs/ui/{request_id}) must pass
+    route_checks for plain internal users, not just admins — the handler
+    itself already self-authorizes row ownership via
+    _assert_user_can_view_request_id.
+    """
+    route = "/spend/logs/ui/abc-request-id"
+    user_obj = LiteLLM_UserTable(
+        user_id="internal_user",
+        user_email="user@example.com",
+        user_role=user_role.value,
+    )
+    valid_token = UserAPIKeyAuth(
+        user_id="internal_user",
+        user_role=user_role.value,
+    )
+    request = MagicMock(spec=Request)
+    request.query_params = {}
+
+    try:
+        RouteChecks.non_proxy_admin_allowed_routes_check(
+            user_obj=user_obj,
+            _user_role=user_role.value,
+            route=route,
+            request=request,
+            valid_token=valid_token,
+            request_data={},
+        )
+    except Exception as e:
+        pytest.fail(f"{user_role.value} should be able to access {route}. Got error: {str(e)}")
+
+
+@pytest.mark.parametrize(
+    "route_group_name",
+    [
+        "spend_tracking_routes",
+        "internal_user_routes",
+        "internal_user_view_only_routes",
+        "admin_viewer_routes",
+        "org_admin_allowed_routes",
+    ],
+)
+def test_logs_drawer_detail_route_in_every_route_group(route_group_name):
+    """
+    /spend/logs/ui/{request_id} must be reachable through
+    RouteChecks.check_route_access under each role's own route group, so a
+    partial revert (removing the route from `spend_tracking_routes` while
+    leaving `non_proxy_admin_allowed_routes_check` alone) is also caught.
+    """
+    from litellm.proxy._types import LiteLLMRoutes
+
+    allowed_routes = getattr(LiteLLMRoutes, route_group_name).value
+    assert RouteChecks.check_route_access(
+        route="/spend/logs/ui/req-34099", allowed_routes=allowed_routes
+    )
+
+
+def test_logs_drawer_detail_route_allowed_for_scoped_virtual_key():
+    """
+    A virtual key scoped to `allowed_routes=["spend_tracking_routes"]` must be
+    able to reach the Logs drawer detail route.
+    """
+    valid_token = UserAPIKeyAuth(
+        user_id="scoped_key_user",
+        allowed_routes=["spend_tracking_routes"],
+    )
+    assert RouteChecks.is_virtual_key_allowed_to_call_route(
+        route="/spend/logs/ui/req-34099", valid_token=valid_token
+    )
+
+
 @pytest.mark.parametrize("route", ADMIN_VIEWER_LOGS_PAGE_ROUTES)
 def test_internal_user_blocked_from_admin_viewer_logs_routes(route):
     """
@@ -3826,3 +3902,17 @@ def test_team_disable_logging_stays_proxy_admin_only():
 def test_neighbouring_team_routes_stay_closed(route):
     """The grant is the callback paths and nothing else on the team namespace."""
     assert "Only proxy admin" in _gate(route, LitellmUserRoles.INTERNAL_USER.value)
+
+
+@pytest.mark.parametrize(
+    "route",
+    [
+        "/claude-code/marketplace.json",
+        "/claude-code/plugins",
+        "/claude-code/plugins/my-skill",
+    ],
+)
+def test_claude_code_marketplace_routes_open_to_internal_users(route):
+    """Per-skill visibility is enforced inside the handler, so the route gate must let non-admins through."""
+    assert RouteChecks.is_llm_api_route(route) is True
+    assert _gate(route, LitellmUserRoles.INTERNAL_USER.value) == "allowed"
diff --git a/tests/test_litellm/proxy/auth/test_team_grants.py b/tests/test_litellm/proxy/auth/test_team_grants.py
new file mode 100644
index 00000000000..447fc1c93a1
--- /dev/null
+++ b/tests/test_litellm/proxy/auth/test_team_grants.py
@@ -0,0 +1,129 @@
+import pytest
+
+from litellm.proxy._types import (
+    LiteLLM_BudgetTable,
+    LiteLLM_ObjectPermissionTable,
+    LiteLLM_TeamMembership,
+    LiteLLM_TeamTable,
+    LiteLLM_VerificationTokenView,
+    Member,
+    UserAPIKeyAuth,
+)
+from litellm.models.team import LiteLLM_ModelTable
+from litellm.proxy.auth.team_grants import team_grants, team_model_aliases
+
+TEAM_ID = "team-grants"
+USER_ID = "user-in-team"
+ALIASES = {"fast": "gpt-4o-mini", "smart": "gpt-4o"}
+
+
+def _alias_table(model_aliases) -> LiteLLM_ModelTable:
+    return LiteLLM_ModelTable(model_aliases=model_aliases, created_by="admin", updated_by="admin")
+
+
+def _full_team(model_aliases=ALIASES) -> LiteLLM_TeamTable:
+    return LiteLLM_TeamTable(
+        team_id=TEAM_ID,
+        team_alias="grants-team",
+        tpm_limit=1000,
+        rpm_limit=10,
+        max_budget=50.0,
+        soft_budget=25.0,
+        spend=12.5,
+        models=["gpt-4o", "gpt-4o-mini"],
+        blocked=True,
+        metadata={"tier": "gold"},
+        litellm_model_table=_alias_table(model_aliases),
+        object_permission_id="op-1",
+        object_permission=LiteLLM_ObjectPermissionTable(object_permission_id="op-1", mcp_servers=["mcp-a"]),
+        members_with_roles=[
+            Member(user_id="someone-else", role="user"),
+            Member(user_id=USER_ID, role="admin"),
+        ],
+    )
+
+
+def _membership() -> LiteLLM_TeamMembership:
+    return LiteLLM_TeamMembership(
+        user_id=USER_ID,
+        team_id=TEAM_ID,
+        spend=3.25,
+        litellm_budget_table=LiteLLM_BudgetTable(tpm_limit=500, rpm_limit=5),
+    )
+
+
+def test_team_grants_cover_every_team_field_the_key_path_gets():
+    """Class guard for LIT-5858 and its siblings: every ``team_*`` column the combined-view SQL hands the
+    virtual-key path must come out of the projection too, with the team's actual value, so adding a column
+    to ``LiteLLM_VerificationTokenView`` without teaching ``team_grants`` fails here instead of in prod."""
+    team = _full_team()
+    grants = team_grants(team_object=team, team_membership=_membership(), user_id=USER_ID)
+    token = UserAPIKeyAuth(team_id=TEAM_ID, **grants)
+
+    view_team_fields = {name for name in LiteLLM_VerificationTokenView.model_fields if name.startswith("team_")}
+    assert view_team_fields - {"team_id"} <= set(grants)
+    assert all(grants[name] is not None for name in view_team_fields - {"team_id"})
+
+    assert token.team_alias == "grants-team"
+    assert token.team_tpm_limit == 1000
+    assert token.team_rpm_limit == 10
+    assert token.team_max_budget == 50.0
+    assert token.team_soft_budget == 25.0
+    assert token.team_spend == 12.5
+    assert token.team_models == ["gpt-4o", "gpt-4o-mini"]
+    assert token.team_blocked is True
+    assert token.team_metadata == {"tier": "gold"}
+    assert token.team_model_aliases == ALIASES
+    assert token.team_object_permission_id == "op-1"
+    assert token.team_object_permission is not None
+    assert token.team_object_permission.mcp_servers == ["mcp-a"]
+    assert token.team_member == Member(user_id=USER_ID, role="admin")
+    assert token.team_member_spend == 3.25
+    assert token.team_member_tpm_limit == 500
+    assert token.team_member_rpm_limit == 5
+
+
+def test_team_grants_without_team_leave_token_defaults():
+    token = UserAPIKeyAuth(**team_grants(team_object=None, team_membership=None, user_id=USER_ID))
+    assert token == UserAPIKeyAuth()
+
+
+@pytest.mark.parametrize(
+    "stored_aliases",
+    [ALIASES, '{"fast": "gpt-4o-mini", "smart": "gpt-4o"}'],
+    ids=["json-object", "json-string-as-written-by-team-new"],
+)
+def test_team_model_aliases_decode_both_storage_shapes(stored_aliases):
+    team = _full_team(model_aliases=stored_aliases)
+    assert team_model_aliases(team) == ALIASES
+    assert team_grants(team_object=team, team_membership=None, user_id=None)["team_model_aliases"] == ALIASES
+
+
+@pytest.mark.parametrize("stored_aliases", [None, "not json", '["a", "b"]', {"fast": 3}], ids=str)
+def test_team_model_aliases_treat_unusable_column_as_no_aliases(stored_aliases):
+    team = _full_team(model_aliases=stored_aliases)
+    assert team_model_aliases(team) is None
+    assert team_grants(team_object=team, team_membership=None, user_id=None)["team_model_aliases"] is None
+
+
+def test_team_model_aliases_none_without_relation_loaded():
+    team = _full_team()
+    team.litellm_model_table = None
+    assert team_model_aliases(team) is None
+    assert team_model_aliases(None) is None
+
+
+def test_team_member_is_the_callers_row_only():
+    team = _full_team()
+    assert team_grants(team_object=team, team_membership=None, user_id="someone-else")["team_member"] == Member(
+        user_id="someone-else", role="user"
+    )
+    assert team_grants(team_object=team, team_membership=None, user_id="stranger")["team_member"] is None
+    assert team_grants(team_object=team, team_membership=None, user_id=None)["team_member"] is None
+
+
+def test_membership_limits_absent_without_membership_row():
+    grants = team_grants(team_object=_full_team(), team_membership=None, user_id=USER_ID)
+    assert grants["team_member_spend"] is None
+    assert grants["team_member_tpm_limit"] is None
+    assert grants["team_member_rpm_limit"] is None
diff --git a/tests/test_litellm/proxy/auth/test_user_api_key_auth.py b/tests/test_litellm/proxy/auth/test_user_api_key_auth.py
index fd289e33ea6..6cce6d0316b 100644
--- a/tests/test_litellm/proxy/auth/test_user_api_key_auth.py
+++ b/tests/test_litellm/proxy/auth/test_user_api_key_auth.py
@@ -7133,3 +7133,162 @@ def test_user_api_key_auth_opens_a_datadog_span_for_accepted_and_rejected_keys(t
     assert report["outcomes"] == ["accepted", "rejected"]
     auth_span = "litellm.proxy.auth.user_api_key_auth.user_api_key_auth"
     assert [span for span in report["spans"] if span == auth_span] == [auth_span, auth_span]
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("is_proxy_admin", [False, True], ids=["standard-return", "proxy-admin-return"])
+async def test_jwt_builder_returns_every_team_grant_the_key_path_gets(is_proxy_admin):
+    """LIT-5858: the team-based JWT path hand-built ``UserAPIKeyAuth`` from a short list of team fields, so the
+    team's model aliases (and on the admin return, its object permission) never reached the token and alias
+    requests 403'd. Both returns now go through ``team_grants``; pin the fields that used to be dropped."""
+    import litellm.proxy.proxy_server as _proxy_server_mod
+    from fastapi import Request
+    from starlette.datastructures import URL
+
+    from litellm.models.team import LiteLLM_ModelTable
+    from litellm.proxy._types import (
+        LiteLLM_ObjectPermissionTable,
+        LiteLLM_TeamMembership,
+        LiteLLM_TeamTable,
+        Member,
+    )
+
+    class _AcceptEveryJwt(JWTHandler):
+        def is_jwt(self, token: str) -> bool:
+            return True
+
+    jwt_handler = _AcceptEveryJwt()
+    jwt_handler.litellm_jwtauth = LiteLLM_JWTAuth()
+
+    team = LiteLLM_TeamTable(
+        team_id="team-jwt-aliases",
+        team_alias="jwt-aliases",
+        models=["gpt-4o"],
+        max_budget=40.0,
+        spend=4.0,
+        blocked=False,
+        metadata={"tier": "gold"},
+        litellm_model_table=LiteLLM_ModelTable(
+            model_aliases='{"fast": "gpt-4o"}', created_by="admin", updated_by="admin"
+        ),
+        object_permission_id="op-jwt",
+        object_permission=LiteLLM_ObjectPermissionTable(object_permission_id="op-jwt", mcp_servers=["mcp-a"]),
+        members_with_roles=[Member(user_id="jwt-user", role="admin")],
+    )
+    membership = LiteLLM_TeamMembership(user_id="jwt-user", team_id="team-jwt-aliases", spend=1.5)
+    builder_result = {
+        "is_proxy_admin": is_proxy_admin,
+        "team_object": team,
+        "user_object": None,
+        "end_user_object": None,
+        "org_object": None,
+        "token": "jwt",
+        "team_id": "team-jwt-aliases",
+        "user_id": "jwt-user",
+        "user_email": "jwt-user@example.com",
+        "end_user_id": None,
+        "org_id": None,
+        "team_membership": membership,
+        "jwt_claims": {"sub": "jwt-user"},
+    }
+
+    mock_proxy_logging_obj = MagicMock()
+    mock_proxy_logging_obj.internal_usage_cache = MagicMock()
+    mock_proxy_logging_obj.internal_usage_cache.dual_cache = AsyncMock()
+    mock_proxy_logging_obj.post_call_failure_hook = AsyncMock(return_value=None)
+    attrs = {
+        "prisma_client": MagicMock(),
+        "user_api_key_cache": DualCache(),
+        "proxy_logging_obj": mock_proxy_logging_obj,
+        "master_key": "sk-master-key",
+        "general_settings": {"enable_jwt_auth": True},
+        "llm_model_list": [],
+        "llm_router": None,
+        "open_telemetry_logger": None,
+        "model_max_budget_limiter": MagicMock(),
+        "user_custom_auth": None,
+        "jwt_handler": jwt_handler,
+        "premium_user": True,
+        "litellm_proxy_admin_name": "admin",
+    }
+    originals = {a: getattr(_proxy_server_mod, a, None) for a in attrs}
+    try:
+        for k, v in attrs.items():
+            setattr(_proxy_server_mod, k, v)
+        request = Request(scope={"type": "http", "headers": [], "method": "POST"})
+        request._url = URL(url="/chat/completions")
+        with patch(  # test-quality-ok: auth_builder is the claim-resolution seam; the regression is how its result is projected onto the token
+            "litellm.proxy.auth.user_api_key_auth.JWTAuthManager.auth_builder",
+            new_callable=AsyncMock,
+            return_value=builder_result,
+        ):
+            token = await _user_api_key_auth_builder(
+                request=request,
+                api_key="Bearer header.payload.signature",
+                azure_api_key_header="",
+                anthropic_api_key_header=None,
+                google_ai_studio_api_key_header=None,
+                azure_apim_header=None,
+                request_data={},
+            )
+    finally:
+        for k, v in originals.items():
+            setattr(_proxy_server_mod, k, v)
+
+    assert token.team_id == "team-jwt-aliases"
+    assert token.user_role == (LitellmUserRoles.PROXY_ADMIN if is_proxy_admin else LitellmUserRoles.INTERNAL_USER)
+    assert token.team_model_aliases == {"fast": "gpt-4o"}
+    assert token.team_object_permission is not None
+    assert token.team_object_permission.mcp_servers == ["mcp-a"]
+    assert token.team_object_permission_id == "op-jwt"
+    assert token.team_alias == "jwt-aliases"
+    assert token.team_models == ["gpt-4o"]
+    assert token.team_max_budget == 40.0
+    assert token.team_spend == 4.0
+    assert token.team_metadata == {"tier": "gold"}
+    assert token.team_member == Member(user_id="jwt-user", role="admin")
+    assert token.team_member_spend == 1.5
+    assert token.jwt_claims == {"sub": "jwt-user"}
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("route", ["/v1/messages", "/messages", "/v1/chat/completions", "/chat/completions", "/v1/responses", "/responses"])
+async def test_claude_view_normalizes_before_model_access(monkeypatch, route):
+    from starlette.requests import Request
+    from litellm.proxy.auth.user_api_key_auth import _enforce_key_and_fallback_model_access
+
+    source = "foo[1m]"
+    encoded = "claude-router-" + source.encode().hex() + "[1m]"
+    router = litellm.Router(model_list=[{"model_name": source, "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-fake"}}])
+    monkeypatch.setattr(litellm.proxy.proxy_server, "llm_router", router)
+    data = {"model": encoded, "messages": [{"role": "user", "content": "hi"}]}
+    request = Request({"type": "http", "method": "POST", "path": route, "headers": [], "query_string": b""})
+    token = UserAPIKeyAuth(models=[source])
+    await _enforce_key_and_fallback_model_access(valid_token=token, request_data=data, route=route, request=request, llm_model_list=router.model_list, llm_router=router)
+    assert data["model"] == source
+    assert (await request.json())["model"] == source
+    assert json.loads(await request.body())["model"] == source
+    assert request.scope["parsed_body"][1]["model"] == source
+    with pytest.raises(ProxyException):
+        await _enforce_key_and_fallback_model_access(valid_token=UserAPIKeyAuth(models=["other"]), request_data=data, route=route, request=request, llm_model_list=router.model_list, llm_router=router)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("layer", ["literal", "global", "router", "key", "hierarchical", "unclaimed"])
+async def test_claude_view_never_reinterprets_explicit_names(monkeypatch, layer):
+    from starlette.requests import Request
+    from litellm.proxy.auth.user_api_key_auth import _normalize_claude_model
+
+    encoded = "claude-router-666f6f"
+    names = ("foo", "other", encoded) if layer == "literal" else ("foo", "other")
+    alias = {encoded: "other"}
+    router = litellm.Router(model_list=[{"model_name": name, "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-fake"}} for name in names], model_group_alias=alias if layer == "router" else None)
+    monkeypatch.setattr(litellm.proxy.proxy_server, "llm_router", router)
+    monkeypatch.setattr(litellm, "model_alias_map", alias if layer == "global" else {})
+    token = UserAPIKeyAuth(aliases=alias if layer == "key" else {}, router_settings={"model_group_alias": alias} if layer == "hierarchical" else None)
+    data = {"model": encoded}
+    request = Request({"type": "http", "method": "POST", "path": "/v1/messages", "headers": [], "query_string": b""})
+    await _normalize_claude_model(data, token, request, "/v1/messages")
+    assert data["model"] == ("foo" if layer == "unclaimed" else encoded)
+    await _normalize_claude_model(data, token, request, "/v1/messages")
+    assert data["model"] == ("foo" if layer == "unclaimed" else encoded)
diff --git a/tests/test_litellm/proxy/client/cli/autoroute/test_commands.py b/tests/test_litellm/proxy/client/cli/autoroute/test_commands.py
index 4a3b3ef22c4..77742ea9f9f 100644
--- a/tests/test_litellm/proxy/client/cli/autoroute/test_commands.py
+++ b/tests/test_litellm/proxy/client/cli/autoroute/test_commands.py
@@ -159,6 +159,10 @@ class TestUpCommand:
         assert captured["settings"]["env"]["ANTHROPIC_AUTH_TOKEN"] == "fixed-master-key"
         assert captured["settings"]["env"]["ENABLE_TOOL_SEARCH"] == "true"
         assert "apiKeyHelper" not in captured["settings"]
+        # The ephemeral proxy serves only the autorouter, so a starting model left by
+        # `lite configure claude --model` or a user pin would 400 on the first message.
+        assert captured["settings"]["model"] == "autorouter"
+        assert captured["settings"]["env"]["ANTHROPIC_DEFAULT_SONNET_MODEL"] == "autorouter"
         assert captured["settings_mode"] == 0o600
 
         assert terminate_calls == [99999]
diff --git a/tests/test_litellm/proxy/client/cli/autoroute/test_settings.py b/tests/test_litellm/proxy/client/cli/autoroute/test_settings.py
deleted file mode 100644
index 87a33c79a79..00000000000
--- a/tests/test_litellm/proxy/client/cli/autoroute/test_settings.py
+++ /dev/null
@@ -1,63 +0,0 @@
-from litellm.proxy.client.cli.commands.autoroute.settings import (
-    ANTHROPIC_DEFAULT_MODEL_ENV_KEYS,
-    merge_claude_settings_static_token,
-)
-
-
-def test_preserves_unrelated_top_level_keys():
-    merged = merge_claude_settings_static_token({"theme": "dark"}, "http://127.0.0.1:4000", "token-abc")
-    assert merged["theme"] == "dark"
-
-
-def test_preserves_unrelated_env_keys():
-    settings = {"env": {"SOME_OTHER_VAR": "value"}}
-    merged = merge_claude_settings_static_token(settings, "http://127.0.0.1:4000", "token-abc")
-    assert merged["env"]["SOME_OTHER_VAR"] == "value"
-
-
-def test_sets_base_url_and_auth_token():
-    merged = merge_claude_settings_static_token({}, "http://127.0.0.1:4000/", "token-abc")
-    assert merged["env"]["ANTHROPIC_BASE_URL"] == "http://127.0.0.1:4000"
-    assert merged["env"]["ANTHROPIC_AUTH_TOKEN"] == "token-abc"
-    assert merged["env"]["ENABLE_TOOL_SEARCH"] == "true"
-
-
-def test_preserves_existing_tool_search():
-    settings = {"env": {"ENABLE_TOOL_SEARCH": "false"}}
-    merged = merge_claude_settings_static_token(settings, "http://127.0.0.1:4000", "token-abc")
-    assert merged["env"]["ENABLE_TOOL_SEARCH"] == "false"
-
-
-def test_drops_stray_api_key():
-    settings = {"env": {"ANTHROPIC_API_KEY": "leaked-key"}}
-    merged = merge_claude_settings_static_token(settings, "http://127.0.0.1:4000", "token-abc")
-    assert "ANTHROPIC_API_KEY" not in merged["env"]
-
-
-def test_removes_existing_api_key_helper():
-    settings = {"apiKeyHelper": "/usr/local/bin/lite auth print-token"}
-    merged = merge_claude_settings_static_token(settings, "http://127.0.0.1:4000", "token-abc")
-    assert "apiKeyHelper" not in merged
-
-
-def test_does_not_mutate_input():
-    settings = {"env": {"FOO": "bar"}, "apiKeyHelper": "old-helper"}
-    merge_claude_settings_static_token(settings, "http://127.0.0.1:4000", "token-abc")
-    assert settings == {"env": {"FOO": "bar"}, "apiKeyHelper": "old-helper"}
-
-
-def test_forces_all_claude_code_default_model_tiers_to_the_autorouter():
-    # A bare "*" model_name deployment looks like the obvious way to catch every request
-    # regardless of which model Claude Code thinks it's using, but Router's auto-router
-    # registry is keyed by the literal requested model string with no wildcard resolution
-    # (litellm/router.py:10711-10717) -- so the only reliable way to make every one of Claude
-    # Code's own tiers hit the auto-router is to override the env vars it reads per tier.
-    merged = merge_claude_settings_static_token({}, "http://127.0.0.1:4000", "token-abc")
-    for key in ANTHROPIC_DEFAULT_MODEL_ENV_KEYS:
-        assert merged["env"][key] == "autorouter"
-
-
-def test_overrides_a_preexisting_default_model_env_var():
-    settings = {"env": {"ANTHROPIC_DEFAULT_SONNET_MODEL": "claude-opus-4-8"}}
-    merged = merge_claude_settings_static_token(settings, "http://127.0.0.1:4000", "token-abc")
-    assert merged["env"]["ANTHROPIC_DEFAULT_SONNET_MODEL"] == "autorouter"
diff --git a/tests/test_litellm/proxy/client/cli/conftest.py b/tests/test_litellm/proxy/client/cli/conftest.py
new file mode 100644
index 00000000000..50c76d3f125
--- /dev/null
+++ b/tests/test_litellm/proxy/client/cli/conftest.py
@@ -0,0 +1,32 @@
+import os
+from collections.abc import Iterator
+from pathlib import Path
+from typing import Final
+
+import pytest
+
+REAL_CLAUDE_SETTINGS: Final = Path(os.path.expanduser("~")) / ".claude" / "settings.json"
+
+
+def _current_bytes() -> bytes | None:
+    return REAL_CLAUDE_SETTINGS.read_bytes() if REAL_CLAUDE_SETTINGS.exists() else None
+
+
+@pytest.fixture(autouse=True)
+def isolated_claude_home(tmp_path: Path, monkeypatch: pytest.MonkeyPatch) -> Iterator[Path]:
+    before: Final = _current_bytes()
+    monkeypatch.setenv("HOME", str(tmp_path))
+    monkeypatch.setenv("USERPROFILE", str(tmp_path))
+    monkeypatch.setenv("CLAUDE_CONFIG_DIR", str(tmp_path / ".claude"))
+    yield tmp_path
+    after: Final = _current_bytes()
+    if after == before:
+        return
+    if before is None:
+        REAL_CLAUDE_SETTINGS.unlink()
+    else:
+        REAL_CLAUDE_SETTINGS.write_bytes(before)
+    pytest.fail(
+        f"this test wrote the developer's real {REAL_CLAUDE_SETTINGS}; the original bytes were restored. "
+        "Resolve the Claude settings path at call time (never Path.home() at import) and point the test at tmp_path"
+    )
diff --git a/tests/test_litellm/proxy/client/cli/test_agents.py b/tests/test_litellm/proxy/client/cli/test_agents.py
index a8a6659fe9a..bebea285edc 100644
--- a/tests/test_litellm/proxy/client/cli/test_agents.py
+++ b/tests/test_litellm/proxy/client/cli/test_agents.py
@@ -28,6 +28,7 @@ from litellm.proxy.client.cli.commands.agents import (
 )
 
 AGENTS_MODULE = "litellm.proxy.client.cli.commands.agents"
+CLAUDE_SETTINGS_MODULE = "litellm.proxy.client.cli.commands.claude_settings"
 
 
 def _agent_command(name):
@@ -163,6 +164,27 @@ class TestBuildAgentEnv:
         assert env["PATH"] == "/usr/bin"
         assert base == {"PATH": "/usr/bin", "ANTHROPIC_API_KEY": "real-key"}
 
+    def test_anthropic_profile_leaves_the_bearer_to_the_api_key_helper(self):
+        env = build_agent_env(
+            {"ANTHROPIC_AUTH_TOKEN": "stale-token", "ANTHROPIC_API_KEY": "real-key"},
+            "http://localhost:4000/",
+            "sk-key",
+            frozenset({"anthropic"}),
+            export_anthropic_token=False,
+        )
+        assert "ANTHROPIC_AUTH_TOKEN" not in env
+        assert "ANTHROPIC_API_KEY" not in env
+        assert env["ANTHROPIC_BASE_URL"] == "http://localhost:4000"
+        assert env["ENABLE_TOOL_SEARCH"] == "true"
+        assert env["CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"] == "1"
+
+    def test_helper_mode_still_exports_the_openai_key(self):
+        env = build_agent_env(
+            {}, "http://localhost:4000", "sk-key", frozenset({"anthropic", "openai"}), export_anthropic_token=False
+        )
+        assert "ANTHROPIC_AUTH_TOKEN" not in env
+        assert env["OPENAI_API_KEY"] == "sk-key"
+
 
 class TestAgentLaunchArgs:
     def test_claude_and_opencode_get_no_extra_args(self):
@@ -509,6 +531,25 @@ class TestRunAgent:
         assert "ANTHROPIC_API_KEY" not in env
         assert "OPENAI_BASE_URL" not in env
 
+    def test_helper_supplied_token_never_reaches_the_launch_env(self):
+        calls = {}
+        verified = []
+
+        run_agent(
+            "http://localhost:4000",
+            "sk-key",
+            ["claude"],
+            base_env={"PATH": "/usr/bin", "ANTHROPIC_AUTH_TOKEN": "stale-token"},
+            which=lambda name: "/usr/local/bin/claude",
+            verify=lambda base_url, api_key: verified.append(api_key),
+            launcher=lambda p, a, e: calls.update(env=dict(e)),
+            export_anthropic_token=False,
+        )
+
+        assert verified == ["sk-key"]
+        assert "ANTHROPIC_AUTH_TOKEN" not in calls["env"]
+        assert calls["env"]["ANTHROPIC_BASE_URL"] == "http://localhost:4000"
+
     def test_codex_gets_openai_env(self):
         calls = {}
         run_agent(
@@ -1052,6 +1093,101 @@ class TestAgentCommands:
             in result.output
         )
 
+    def _invoke_claude_with_settings(self, tmp_path, settings, obj, *, default_settings=None):
+        config_dir = tmp_path / "claude-config"
+        config_dir.mkdir()
+        if settings is not None:
+            (config_dir / "settings.json").write_text(json.dumps(settings))
+        default_path = tmp_path / "home-claude" / "settings.json"
+        default_path.parent.mkdir()
+        if default_settings is not None:
+            default_path.write_text(json.dumps(default_settings))
+        captured = {}
+        with (
+            patch(f"{CLAUDE_SETTINGS_MODULE}.CLAUDE_SETTINGS_PATH", default_path),
+            patch(f"{CLAUDE_SETTINGS_MODULE}.shutil.which", return_value="/usr/local/bin/lite"),
+            patch(f"{AGENTS_MODULE}.run_agent", side_effect=lambda b, k, c, **kw: captured.update(kw)),
+        ):
+            result = self.runner.invoke(
+                _agent_command("claude"), [], obj=obj, env={"CLAUDE_CONFIG_DIR": str(config_dir)}
+            )
+        assert result.exit_code == 0, result.output
+        return captured, result.output
+
+    def test_helper_is_read_from_the_config_dir_claude_code_uses(self, tmp_path):
+        captured, output = self._invoke_claude_with_settings(
+            tmp_path,
+            {"apiKeyHelper": "/usr/local/bin/lite --base-url http://localhost:4000 auth print-token"},
+            {"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": True},
+        )
+
+        assert captured["export_anthropic_token"] is False
+        assert str(tmp_path / "claude-config" / "settings.json") in output
+
+    def test_helper_only_in_the_default_file_keeps_the_env_token_when_config_dir_points_elsewhere(self, tmp_path):
+        captured, output = self._invoke_claude_with_settings(
+            tmp_path,
+            None,
+            {"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": True},
+            default_settings={"apiKeyHelper": "/usr/local/bin/lite --base-url http://localhost:4000 auth print-token"},
+        )
+
+        assert captured["export_anthropic_token"] is True
+        assert "apiKeyHelper" not in output
+
+    def test_stored_login_with_a_matching_helper_leaves_the_token_to_the_helper(self, tmp_path):
+        captured, output = self._invoke_claude_with_settings(
+            tmp_path,
+            {"apiKeyHelper": "/usr/local/bin/lite --base-url http://localhost:4000 auth print-token"},
+            {"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": True},
+        )
+
+        assert captured["export_anthropic_token"] is False
+        assert "reads its key from the apiKeyHelper" in output
+
+    def test_explicit_key_is_exported_even_when_a_helper_matches(self, tmp_path):
+        captured, output = self._invoke_claude_with_settings(
+            tmp_path,
+            {"apiKeyHelper": "/usr/local/bin/lite --base-url http://localhost:4000 auth print-token"},
+            {"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": False},
+        )
+
+        assert captured["export_anthropic_token"] is True
+        assert "apiKeyHelper" not in output
+
+    def test_helper_for_another_proxy_keeps_the_env_token(self, tmp_path):
+        captured, _ = self._invoke_claude_with_settings(
+            tmp_path,
+            {"apiKeyHelper": "/usr/local/bin/lite --base-url https://other.example.com auth print-token"},
+            {"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": True},
+        )
+
+        assert captured["export_anthropic_token"] is True
+
+    def test_no_claude_settings_keeps_the_env_token(self, tmp_path):
+        captured, _ = self._invoke_claude_with_settings(
+            tmp_path,
+            None,
+            {"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": True},
+        )
+
+        assert captured["export_anthropic_token"] is True
+
+    def test_codex_never_consults_claude_settings(self):
+        captured = {}
+        with (
+            patch(f"{AGENTS_MODULE}.lite_api_key_helper_configured", side_effect=AssertionError("consulted")),
+            patch(f"{AGENTS_MODULE}.run_agent", side_effect=lambda b, k, c, **kw: captured.update(kw)),
+        ):
+            result = self.runner.invoke(
+                _agent_command("codex"),
+                [],
+                obj={"base_url": "http://localhost:4000", "api_key": "sk-key", "api_key_from_token_file": True},
+            )
+
+        assert result.exit_code == 0, result.output
+        assert captured["export_anthropic_token"] is True
+
     def test_codex_shows_friendly_name(self):
         captured = {}
         with patch(
diff --git a/tests/test_litellm/proxy/client/cli/test_auth_commands.py b/tests/test_litellm/proxy/client/cli/test_auth_commands.py
index 821323e722c..1f314e0c9d8 100644
--- a/tests/test_litellm/proxy/client/cli/test_auth_commands.py
+++ b/tests/test_litellm/proxy/client/cli/test_auth_commands.py
@@ -6,7 +6,6 @@ from pathlib import Path
 from unittest.mock import Mock, patch
 
 
-
 import pytest
 from click.testing import CliRunner
 
@@ -27,6 +26,7 @@ from litellm.proxy.client.cli.commands.auth import (
     print_token,
     whoami,
 )
+from litellm.proxy.client.cli.commands import claude_settings as claude_settings_module
 from litellm.proxy.client.cli.commands.claude_settings import SettingsFileOwner
 
 
@@ -84,7 +84,7 @@ class TestPollingErrorSurfacing:
         }
 
         with patch("requests.get", return_value=mock_response) as mock_get, patch("time.sleep"):
-            with pytest.raises(ValueError, match='Your litellm CLI is out of date and uses a login flow') as exc_info:
+            with pytest.raises(ValueError, match="Your litellm CLI is out of date and uses a login flow") as exc_info:
                 _poll_for_ready_data("http://test/sso/cli/poll/sk-legacy")
 
         assert mock_get.call_count == 1
@@ -151,7 +151,7 @@ class TestStartCliSsoFlowErrors:
         mock_response.status_code = 404
 
         with patch("requests.post", return_value=mock_response):
-            with pytest.raises(ValueError, match='Either --base-url is wrong, or the proxy is older than') as exc_info:
+            with pytest.raises(ValueError, match="Either --base-url is wrong, or the proxy is older than") as exc_info:
                 _start_cli_sso_flow("https://old-proxy.example.com")
 
         message = str(exc_info.value)
@@ -167,7 +167,7 @@ class TestStartCliSsoFlowErrors:
         mock_response.json.return_value = {"detail": "Too many CLI login attempts. Try again later."}
 
         with patch("requests.post", return_value=mock_response):
-            with pytest.raises(ValueError, match='Too many CLI login attempts\\. Try again later\\.') as exc_info:
+            with pytest.raises(ValueError, match="Too many CLI login attempts\\. Try again later\\.") as exc_info:
                 _start_cli_sso_flow("https://test.example.com")
 
         assert "HTTP 429" in str(exc_info.value)
@@ -183,7 +183,7 @@ class TestStartCliSsoFlowErrors:
         mock_response.text = "<html>Sign in to corporate VPN</html>"
 
         with patch("requests.post", return_value=mock_response):
-            with pytest.raises(ValueError, match='A proxy, load balancer, or auth gateway in front of') as exc_info:
+            with pytest.raises(ValueError, match="A proxy, load balancer, or auth gateway in front of") as exc_info:
                 _start_cli_sso_flow("https://test.example.com")
 
         message = str(exc_info.value)
@@ -197,7 +197,7 @@ class TestStartCliSsoFlowErrors:
         from litellm.proxy.client.cli.commands.auth import _start_cli_sso_flow
 
         with patch("requests.post", side_effect=requests.ConnectionError("Connection refused")):
-            with pytest.raises(ValueError, match='Connection refused\\. Check that the proxy is running') as exc_info:
+            with pytest.raises(ValueError, match="Connection refused\\. Check that the proxy is running") as exc_info:
                 _start_cli_sso_flow("https://unreachable.example.com")
 
         message = str(exc_info.value)
@@ -584,13 +584,9 @@ class TestLogoutCommand:
         assert "could not be checked" in result.output
         assert DISABLE_KEYRING_ENV_VAR in result.output
 
-    def test_logout_warns_when_the_keychain_refuses_to_release_the_entry(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_logout_warns_when_the_keychain_refuses_to_release_the_entry(self, isolated_home, secret_vault_factory):
         """A locked keychain leaves a live credential behind that the user believes is gone."""
-        vault = secret_vault_factory(
-            blob=_secret_blob("https://test.example.com", "sk-stored"), erasable=False
-        )
+        vault = secret_vault_factory(blob=_secret_blob("https://test.example.com", "sk-stored"), erasable=False)
         _write_token_file(isolated_home, key=None)
 
         result = self.runner.invoke(logout, obj={"secret_vault": vault})
@@ -1210,9 +1206,7 @@ class TestKeychainBackedCommands:
         assert str(token_file) in result.output
         assert json.loads(token_file.read_text())["key"] == "sk-minted"
 
-    def test_login_points_a_user_missing_the_keyring_package_at_the_install(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_login_points_a_user_missing_the_keyring_package_at_the_install(self, isolated_home, secret_vault_factory):
         """`lite` ships with every install, the keyring package only with the cli extra. Telling
         that user their machine has no keychain sends them looking for a problem they do not have."""
         result = self._login(secret_vault_factory(available=False, failure=KeyringNotInstalled()))
@@ -1223,9 +1217,7 @@ class TestKeychainBackedCommands:
         assert "No OS keychain available" not in result.output
         assert json.loads(token_file.read_text())["key"] == "sk-minted"
 
-    def test_login_keeps_the_credential_when_the_backend_keeps_nothing(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_login_keeps_the_credential_when_the_backend_keeps_nothing(self, isolated_home, secret_vault_factory):
         """A backend that accepts writes and stores nothing must not be reported as keychain
         storage, because the file is then told to drop the only remaining copy."""
         result = self._login(secret_vault_factory(discards=True))
@@ -1236,9 +1228,7 @@ class TestKeychainBackedCommands:
         assert "keyring --enable" in result.output
         assert json.loads(token_file.read_text())["key"] == "sk-minted"
 
-    def test_login_names_the_kill_switch_instead_of_blaming_the_machine(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_login_names_the_kill_switch_instead_of_blaming_the_machine(self, isolated_home, secret_vault_factory):
         result = self._login(secret_vault_factory(available=False, failure=KeyringDisabled()))
 
         assert result.exit_code == 0
@@ -1297,9 +1287,7 @@ class TestKeychainBackedCommands:
         assert "could not be read" in result.output
         assert "lite login" in result.output
 
-    def test_whoami_does_not_call_a_credential_it_cannot_read_authenticated(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_whoami_does_not_call_a_credential_it_cannot_read_authenticated(self, isolated_home, secret_vault_factory):
         """A login whose secret is stuck in an unreachable keychain authenticates nothing. Leading
         with "Authenticated" and a token age reads as a working session, and sends the user looking
         for the problem somewhere other than the keychain the notice underneath names."""
@@ -1316,9 +1304,7 @@ class TestKeychainBackedCommands:
         assert "the credential cannot be read" in result.output
         assert "could not be read" in result.output
 
-    def test_whoami_names_the_kill_switch_rather_than_a_missing_package(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_whoami_names_the_kill_switch_rather_than_a_missing_package(self, isolated_home, secret_vault_factory):
         """Every unreachable keychain used to be described as a locked one needing the keyring
         package installed. Someone who set the kill switch has the package and an unlocked keychain,
         so that advice sends them to fix two things that were never wrong."""
@@ -1330,9 +1316,7 @@ class TestKeychainBackedCommands:
         assert DISABLE_KEYRING_ENV_VAR in result.output
         assert "pip install" not in result.output
 
-    def test_print_token_points_an_install_without_keyring_at_the_package(
-        self, isolated_home, secret_vault_factory
-    ):
+    def test_print_token_points_an_install_without_keyring_at_the_package(self, isolated_home, secret_vault_factory):
         _write_token_file(isolated_home, key=None)
         vault = secret_vault_factory(available=False, failure=KeyringNotInstalled())
         obj = {"base_url": "https://test.example.com", "secret_vault": vault}
@@ -1398,9 +1382,22 @@ class TestLoginConfigClaude:
     def setup_method(self):
         self.runner = CliRunner()
 
-    def _run_login(self, tmp_path, args, base_url="https://test.example.com"):
-        settings_path = tmp_path / "claude" / "settings.json"
+    def _isolate_default_settings(self, tmp_path, monkeypatch):
+        """The default file, its `lite up` backup and its configure receipt all live under tmp_path."""
         backup_path = tmp_path / "claude_settings_backup.json"
+        monkeypatch.setattr(
+            claude_settings_module, "SETTINGS_FILE_OWNERS", (SettingsFileOwner(backup_path, "lite up", "lite down"),)
+        )
+        monkeypatch.setattr(
+            claude_settings_module, "CLAUDE_SETTINGS_PATH", tmp_path / "default-home" / ".claude" / "settings.json"
+        )
+        monkeypatch.setattr(claude_settings_module, "CONFIGURE_STATE_PATH", tmp_path / "claude_configure_state.json")
+        return backup_path
+
+    def _run_login(self, tmp_path, monkeypatch, args, base_url="https://test.example.com", *, config_dir_env=None):
+        settings_path = tmp_path / "claude" / "settings.json"
+        backup_path = self._isolate_default_settings(tmp_path, monkeypatch)
+        env = {"CLAUDE_CONFIG_DIR": str(settings_path.parent)} if config_dir_env is None else config_dir_env
         poll_response = Mock()
         poll_response.status_code = 200
         poll_response.json.return_value = {
@@ -1416,55 +1413,102 @@ class TestLoginConfigClaude:
             patch("requests.get", return_value=poll_response),
             patch("litellm.proxy.client.cli.commands.auth.save_cli_token"),
             patch("litellm.proxy.client.cli.interface.show_commands"),
-            patch("litellm.proxy.client.cli.commands.auth.CLAUDE_SETTINGS_PATH", settings_path),
-            patch(
-                "litellm.proxy.client.cli.commands.auth.SETTINGS_FILE_OWNERS",
-                (SettingsFileOwner(backup_path, "lite up", "lite down"),),
-            ),
             patch(
                 "litellm.proxy.client.cli.commands.claude_settings.shutil.which",
                 return_value="/usr/local/bin/lite",
             ),
         ):
-            result = self.runner.invoke(login, args, obj={"base_url": base_url})
+            result = self.runner.invoke(login, args, obj={"base_url": base_url}, env=env)
         return result, settings_path, backup_path
 
-    def test_default_login_does_not_touch_claude_settings(self, tmp_path):
-        result, settings_path, _backup_path = self._run_login(tmp_path, [])
+    def test_default_login_does_not_touch_claude_settings(self, tmp_path, monkeypatch):
+        result, settings_path, _backup_path = self._run_login(tmp_path, monkeypatch, [])
 
         assert result.exit_code == 0
         assert "Login successful!" in result.output
         assert not settings_path.exists()
         assert "Configured Claude Code" not in result.output
 
-    def test_flag_writes_the_settings_file_and_reports_success(self, tmp_path):
-        result, settings_path, _backup_path = self._run_login(tmp_path, ["--config-claude"])
+    def test_flag_writes_the_settings_file_and_reports_success(self, tmp_path, monkeypatch):
+        result, settings_path, _backup_path = self._run_login(tmp_path, monkeypatch, ["--config-claude"])
 
         assert result.exit_code == 0
         written = json.loads(settings_path.read_text())
         assert written["env"]["ANTHROPIC_BASE_URL"] == "https://test.example.com"
         assert written["env"]["ENABLE_TOOL_SEARCH"] == "true"
         assert written["apiKeyHelper"] == "/usr/local/bin/lite --base-url https://test.example.com auth print-token"
-        assert "Configured Claude Code" in result.output
+        assert f"Configured Claude Code: {settings_path} now routes through https://test.example.com." in result.output
+        assert "pins a proxy model for every tier" not in result.output
+        assert "the model Claude Code starts on" in result.output
 
-    def test_flag_preserves_unrelated_settings_on_an_existing_file(self, tmp_path):
+    def test_flag_preserves_unrelated_settings_on_an_existing_file(self, tmp_path, monkeypatch):
         settings_path = tmp_path / "claude" / "settings.json"
         settings_path.parent.mkdir(parents=True)
         settings_path.write_text(json.dumps({"theme": "dark", "env": {"KEEP": "me"}}))
 
-        result, _settings_path, _backup_path = self._run_login(tmp_path, ["--config-claude"])
+        result, _settings_path, _backup_path = self._run_login(tmp_path, monkeypatch, ["--config-claude"])
 
         assert result.exit_code == 0
         written = json.loads(settings_path.read_text())
         assert written["theme"] == "dark"
         assert written["env"]["KEEP"] == "me"
 
-    def test_settings_failure_is_reported_without_claiming_login_failed(self, tmp_path):
+    def _run_login_refused_before_the_sso_flow(self, tmp_path, monkeypatch, config_dir):
+        self._isolate_default_settings(tmp_path, monkeypatch).write_text("{}")
+        with patch("requests.post") as post, patch("webbrowser.open") as browser:
+            result = self.runner.invoke(
+                login,
+                ["--config-claude"],
+                obj={"base_url": "https://test.example.com"},
+                env={"CLAUDE_CONFIG_DIR": config_dir},
+            )
+        assert result.exit_code != 0
+        assert "not logging in" in result.output and "lite down" in result.output
+        assert "`lite up` is currently managing" in result.output
+        assert "Login successful!" not in result.output
+        post.assert_not_called()
+        browser.assert_not_called()
+        assert not (tmp_path / "default-home" / ".claude" / "settings.json").exists()
+
+    def test_refuses_before_logging_in_while_lite_up_holds_the_default_settings_file(self, tmp_path, monkeypatch):
+        self._run_login_refused_before_the_sso_flow(tmp_path, monkeypatch, config_dir="")
+
+    def test_refuses_before_logging_in_while_lite_up_holds_the_default_file_reached_through_a_symlink(
+        self, tmp_path, monkeypatch
+    ):
+        default_config_dir = tmp_path / "default-home" / ".claude"
+        default_config_dir.mkdir(parents=True)
+        alias = tmp_path / "claude-alias"
+        alias.symlink_to(default_config_dir, target_is_directory=True)
+
+        self._run_login_refused_before_the_sso_flow(tmp_path, monkeypatch, config_dir=str(alias))
+
+    def test_flag_writes_an_alternate_config_dir_even_while_lite_up_holds_the_default_file(self, tmp_path, monkeypatch):
+        (tmp_path / "claude_settings_backup.json").write_text("{}")
+
+        result, settings_path, _backup_path = self._run_login(tmp_path, monkeypatch, ["--config-claude"])
+
+        assert result.exit_code == 0, result.output
+        written = json.loads(settings_path.read_text())
+        assert written["apiKeyHelper"] == "/usr/local/bin/lite --base-url https://test.example.com auth print-token"
+        assert f"Configured Claude Code: {settings_path} now routes through https://test.example.com." in result.output
+
+    def test_flag_keeps_a_config_dir_receipt_apart_from_the_default_file_receipt(self, tmp_path, monkeypatch):
+        result, settings_path, _backup_path = self._run_login(tmp_path, monkeypatch, ["--config-claude"])
+
+        assert result.exit_code == 0, result.output
+        default_receipt = tmp_path / "claude_configure_state.json"
+        assert not default_receipt.exists()
+        receipts = list((tmp_path / "claude_configure_state").glob("*.json"))
+        assert len(receipts) == 1
+        assert json.loads(receipts[0].read_text())["file_existed"] is False
+
+    def test_settings_failure_is_reported_without_claiming_login_failed(self, tmp_path, monkeypatch):
         settings_path = tmp_path / "claude" / "settings.json"
         settings_path.parent.mkdir(parents=True)
         settings_path.write_text("not json at all {{{")
 
-        result, _settings_path, _backup_path = self._run_login(tmp_path, ["--config-claude"])
+        result, _settings_path, _backup_path = self._run_login(tmp_path, monkeypatch, ["--config-claude"])
 
         assert result.exit_code != 0
         assert "Login successful!" in result.output
@@ -1853,7 +1897,10 @@ class TestPkcePrintToken:
         assert result.stdout == ""
         assert sum(len(session.posts) for session in _FakeSession.instances) == 1
         assert result.output.count("Could not renew the key") == 1
-        assert "Could not renew the key: token request failed with 400: the refresh token was already used" in result.output
+        assert (
+            "Could not renew the key: token request failed with 400: the refresh token was already used"
+            in result.output
+        )
         assert "Key expired. Run 'lite login --pkce' again." in result.output
         save.assert_not_called()
 
diff --git a/tests/test_litellm/proxy/client/cli/test_claude_settings.py b/tests/test_litellm/proxy/client/cli/test_claude_settings.py
index e5f2a9d95bd..fc2d98f2264 100644
--- a/tests/test_litellm/proxy/client/cli/test_claude_settings.py
+++ b/tests/test_litellm/proxy/client/cli/test_claude_settings.py
@@ -1,7 +1,9 @@
 import json
+import os
 import shlex
 import stat
 import time
+from pathlib import Path
 from unittest.mock import patch
 
 import pytest
@@ -9,14 +11,30 @@ from click.testing import CliRunner
 
 from litellm.litellm_core_utils.cli_token_utils import CliTokenRecord
 from litellm.proxy.client.cli import cli
+from litellm.litellm_core_utils.private_json import commit_staged_json
 from litellm.proxy.client.cli.commands.claude_settings import (
+    ANTHROPIC_DEFAULT_MODEL_ENV_KEYS,
     AUTOROUTE_BACKUP_PATH,
     BACKUP_PATH,
+    CLAUDE_SETTINGS_PATH,
+    CONFIGURE_STATE_PATH,
+    OWNED_ENV_KEYS,
+    OWNED_TOP_LEVEL_KEYS,
     SETTINGS_FILE_OWNERS,
+    ApiKeyHelper,
     ClaudeSettingsError,
+    KeepModel,
     SettingsFileOwner,
+    StartOn,
+    StaticToken,
+    UnpinModel,
+    claude_settings_path,
+    configure_claude_settings,
+    configure_state_path,
+    lite_api_key_helper_configured,
+    merge_claude_settings,
     resolve_api_key_helper,
-    write_claude_settings,
+    unconfigure_claude_settings,
 )
 
 
@@ -24,6 +42,7 @@ def _owners(*backup_paths):
     """Stand-in owners for the real `lite up` / `lite autoroute up` registry."""
     return tuple(SettingsFileOwner(path, "lite up", "lite down") for path in backup_paths)
 
+
 CLAUDE_SETTINGS_MODULE = "litellm.proxy.client.cli.commands.claude_settings"
 AUTH_MODULE = "litellm.proxy.client.cli.commands.auth"
 WINDOWS_LITE_EXE = "C:\\Users\\u\\AppData\\Local\\Programs\\Python\\Python313\\Scripts\\lite.EXE"
@@ -97,17 +116,28 @@ def lite_on_path():
         yield
 
 
-class TestWriteClaudeSettings:
+def _helper_configure(base_url, settings_path, owners, state_path=None):
+    """`lite login --config-claude`'s shape: the login credential behind apiKeyHelper, no pinned model."""
+    state = state_path if state_path is not None else settings_path.parent.parent / "state.json"
+    root = base_url.rstrip("/")
+    configure_claude_settings(
+        root, ApiKeyHelper(resolve_api_key_helper(root)), KeepModel(), settings_path, state, owners
+    )
+
+
+class TestConfigureWithTheLoginHelper:
     def test_creates_the_file_and_its_parent_when_missing(self, paths, lite_on_path):
         settings_path, backup_path = paths
         assert not settings_path.parent.exists()
 
-        write_claude_settings("https://proxy.example.com/", settings_path, _owners(backup_path))
+        _helper_configure("https://proxy.example.com/", settings_path, _owners(backup_path))
 
         written = json.loads(settings_path.read_text())
         assert written["env"]["ANTHROPIC_BASE_URL"] == "https://proxy.example.com"
         assert written["env"]["ENABLE_TOOL_SEARCH"] == "true"
+        assert written["env"]["CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"] == "1"
         assert written["apiKeyHelper"] == "/usr/local/bin/lite --base-url https://proxy.example.com auth print-token"
+        assert "model" not in written
 
     def test_updates_an_existing_file_preserving_unrelated_settings(self, paths, lite_on_path):
         settings_path, backup_path = paths
@@ -123,7 +153,7 @@ class TestWriteClaudeSettings:
             )
         )
 
-        write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+        _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
         written = json.loads(settings_path.read_text())
         assert written["theme"] == "dark"
@@ -135,26 +165,31 @@ class TestWriteClaudeSettings:
     def test_rerunning_against_a_new_proxy_refreshes_both_base_url_and_helper(self, paths, lite_on_path):
         settings_path, backup_path = paths
 
-        write_claude_settings("https://first.example.com", settings_path, _owners(backup_path))
-        write_claude_settings("https://second.example.com", settings_path, _owners(backup_path))
+        _helper_configure("https://first.example.com", settings_path, _owners(backup_path))
+        _helper_configure("https://second.example.com", settings_path, _owners(backup_path))
 
         written = json.loads(settings_path.read_text())
         assert written["env"]["ANTHROPIC_BASE_URL"] == "https://second.example.com"
         assert "second.example.com" in written["apiKeyHelper"]
         assert "first.example.com" not in written["apiKeyHelper"]
 
-    def test_drops_a_stray_static_api_key_so_the_helper_token_wins(self, paths, lite_on_path):
+    def test_drops_stray_static_credentials_so_the_helper_token_wins(self, paths, lite_on_path):
+        # Claude Code prefers ANTHROPIC_AUTH_TOKEN over apiKeyHelper, so a virtual key left behind
+        # by an earlier `lite configure claude --api-key` would silently keep winning.
         settings_path, backup_path = paths
         settings_path.parent.mkdir(parents=True)
-        settings_path.write_text(json.dumps({"env": {"ANTHROPIC_API_KEY": "sk-leaked"}}))
+        settings_path.write_text(
+            json.dumps({"env": {"ANTHROPIC_API_KEY": "sk-leaked", "ANTHROPIC_AUTH_TOKEN": "sk-old"}})
+        )
 
-        write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+        _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
-        assert "ANTHROPIC_API_KEY" not in json.loads(settings_path.read_text())["env"]
+        env = json.loads(settings_path.read_text())["env"]
+        assert "ANTHROPIC_API_KEY" not in env and "ANTHROPIC_AUTH_TOKEN" not in env
 
     def test_written_file_is_owner_only(self, paths, lite_on_path):
         settings_path, backup_path = paths
-        write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+        _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
         assert stat.S_IMODE(settings_path.stat().st_mode) == 0o600
 
     def test_refuses_while_lite_up_holds_a_backup(self, paths, lite_on_path):
@@ -162,7 +197,7 @@ class TestWriteClaudeSettings:
         backup_path.write_text("{}")
 
         with pytest.raises(ClaudeSettingsError, match="lite down"):
-            write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+            _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
         assert not settings_path.exists()
 
@@ -172,7 +207,7 @@ class TestWriteClaudeSettings:
         settings_path.write_text("not json at all {{{")
 
         with pytest.raises(ClaudeSettingsError, match="invalid JSON"):
-            write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+            _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
         assert settings_path.read_text() == "not json at all {{{"
 
@@ -180,7 +215,7 @@ class TestWriteClaudeSettings:
         settings_path, backup_path = paths
         with patch(f"{CLAUDE_SETTINGS_MODULE}.shutil.which", return_value=None):
             with pytest.raises(ClaudeSettingsError, match="Could not find `lite`"):
-                write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+                _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
         assert not settings_path.exists()
 
@@ -196,7 +231,7 @@ class TestWriteClaudeSettings:
         settings_path.write_bytes(b'{"theme": "\xff\xfe"}')
 
         with pytest.raises(ClaudeSettingsError, match="invalid JSON"):
-            write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+            _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
     def test_reports_an_actionable_error_when_the_file_cannot_be_read(self, paths, lite_on_path):
         """An unreadable settings file must not surface as "Authentication failed".
@@ -210,16 +245,18 @@ class TestWriteClaudeSettings:
         settings_path.mkdir()
 
         with pytest.raises(ClaudeSettingsError, match="Could not read"):
-            write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+            _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
     def test_reports_an_actionable_error_when_the_file_cannot_be_written(self, paths, lite_on_path):
         settings_path, backup_path = paths
-        with patch(
-            f"{CLAUDE_SETTINGS_MODULE}.write_private_json",
-            side_effect=OSError("Read-only file system"),
-        ):
-            with pytest.raises(ClaudeSettingsError, match="Read-only file system"):
-                write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+        settings_path.parent.mkdir(parents=True)
+        settings_path.parent.chmod(0o500)
+        try:
+            with pytest.raises(ClaudeSettingsError, match="Could not write"):
+                _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
+        finally:
+            settings_path.parent.chmod(0o700)
+        assert not settings_path.exists()
 
 
 class TestApiKeyHelperIsActuallyInvocable:
@@ -303,7 +340,7 @@ class TestConflictingOwnersOfTheSettingsFile:
             backup.write_text("{}")
             stand_in = SettingsFileOwner(backup, owner.start_command, owner.stop_command)
             with pytest.raises(ClaudeSettingsError, match="currently managing"):
-                write_claude_settings("https://proxy.example.com", settings_path, (stand_in,))
+                _helper_configure("https://proxy.example.com", settings_path, (stand_in,))
             backup.unlink()
             assert not settings_path.exists()
 
@@ -314,9 +351,9 @@ class TestConflictingOwnersOfTheSettingsFile:
         autoroute = SettingsFileOwner(backup, "lite autoroute up", "lite autoroute down")
 
         with pytest.raises(ClaudeSettingsError, match="`lite autoroute up` is currently managing"):
-            write_claude_settings("https://proxy.example.com", settings_path, (autoroute,))
+            _helper_configure("https://proxy.example.com", settings_path, (autoroute,))
         with pytest.raises(ClaudeSettingsError, match="Run `lite autoroute down` first"):
-            write_claude_settings("https://proxy.example.com", settings_path, (autoroute,))
+            _helper_configure("https://proxy.example.com", settings_path, (autoroute,))
 
     def test_the_registry_matches_the_paths_the_commands_actually_use(self):
         """A second definition of the autoroute dir must not drift from this one."""
@@ -341,7 +378,7 @@ class TestDoesNotDestroyUserOwnedStructure:
         link.parent.mkdir()
         link.symlink_to(real)
 
-        write_claude_settings("https://proxy.example.com", link, ())
+        _helper_configure("https://proxy.example.com", link, ())
 
         assert link.is_symlink()
         assert json.loads(real.read_text())["env"]["ANTHROPIC_BASE_URL"] == "https://proxy.example.com"
@@ -354,6 +391,567 @@ class TestDoesNotDestroyUserOwnedStructure:
         settings_path.write_text(json.dumps({"theme": "dark", "env": "not-an-object"}))
 
         with pytest.raises(ClaudeSettingsError, match="non-object"):
-            write_claude_settings("https://proxy.example.com", settings_path, _owners(backup_path))
+            _helper_configure("https://proxy.example.com", settings_path, _owners(backup_path))
 
         assert json.loads(settings_path.read_text())["env"] == "not-an-object"
+
+
+class TestClaudeSettingsPath:
+    def test_defaults_to_the_home_settings_file(self):
+        assert claude_settings_path({}) == CLAUDE_SETTINGS_PATH
+        assert claude_settings_path({"CLAUDE_CONFIG_DIR": ""}) == CLAUDE_SETTINGS_PATH
+
+    def test_follows_claude_config_dir_like_claude_code_does(self, tmp_path):
+        assert claude_settings_path({"CLAUDE_CONFIG_DIR": str(tmp_path)}) == tmp_path / "settings.json"
+
+    def test_expands_a_tilde_in_claude_config_dir(self):
+        assert claude_settings_path({"CLAUDE_CONFIG_DIR": "~/.claude-work"}) == (
+            Path.home() / ".claude-work" / "settings.json"
+        )
+
+
+class TestConfigureStatePath:
+    """Each settings file gets its own undo receipt: the default file keeps the long-standing path, and
+    a CLAUDE_CONFIG_DIR file gets one keyed by its resolved location, so `lite unconfigure claude`
+    under one config dir never restores the other file's history."""
+
+    @pytest.fixture
+    def default_paths(self, tmp_path):
+        default_settings = tmp_path / "home" / ".claude" / "settings.json"
+        default_state = tmp_path / "home" / ".litellm" / "claude_configure_state.json"
+        with (
+            patch(f"{CLAUDE_SETTINGS_MODULE}.CLAUDE_SETTINGS_PATH", default_settings),
+            patch(f"{CLAUDE_SETTINGS_MODULE}.CONFIGURE_STATE_PATH", default_state),
+        ):
+            yield default_settings, default_state
+
+    def test_the_default_file_keeps_the_default_receipt(self, default_paths):
+        default_settings, default_state = default_paths
+        assert configure_state_path(default_settings) == default_state
+
+    def test_a_symlink_alias_of_the_default_file_shares_its_receipt(self, default_paths):
+        default_settings, default_state = default_paths
+        default_settings.parent.mkdir(parents=True)
+        alias = default_settings.parent.parent / "claude-alias"
+        alias.symlink_to(default_settings.parent, target_is_directory=True)
+        assert configure_state_path(alias / "settings.json") == default_state
+
+    def test_another_settings_file_gets_a_receipt_of_its_own_beside_the_default_one(self, default_paths, tmp_path):
+        _default_settings, default_state = default_paths
+        work_state = configure_state_path(tmp_path / "work" / "settings.json")
+        play_state = configure_state_path(tmp_path / "play" / "settings.json")
+        assert work_state != default_state and play_state != default_state
+        assert work_state != play_state
+        assert work_state.parent == play_state.parent == default_state.parent / "claude_configure_state"
+        assert work_state == configure_state_path(tmp_path / "work" / "settings.json")
+
+    def test_configure_and_unconfigure_under_a_config_dir_leave_the_default_receipt_alone(
+        self, default_paths, tmp_path, lite_on_path
+    ):
+        _default_settings, default_state = default_paths
+        work_settings = tmp_path / "work" / "settings.json"
+        work_state = configure_state_path(work_settings)
+        configure_claude_settings(
+            "https://proxy.example.com",
+            ApiKeyHelper(resolve_api_key_helper("https://proxy.example.com")),
+            KeepModel(),
+            work_settings,
+            work_state,
+            (),
+        )
+        assert work_state.exists() and not default_state.exists()
+        outcome = unconfigure_claude_settings(work_settings, work_state, ())
+        assert outcome.file_removed and not work_settings.exists()
+        assert not work_state.exists()
+
+
+class TestLiteApiKeyHelperConfigured:
+    def _settings(self, tmp_path, payload):
+        settings_path = tmp_path / "settings.json"
+        settings_path.write_text(payload)
+        return settings_path
+
+    def test_recognises_the_helper_lite_login_wrote_for_this_proxy(self, tmp_path, lite_on_path):
+        settings_path = tmp_path / "settings.json"
+        _helper_configure("https://proxy.example.com/", settings_path, (), tmp_path / "state.json")
+
+        assert lite_api_key_helper_configured("https://proxy.example.com/", settings_path) is True
+        assert lite_api_key_helper_configured("https://proxy.example.com", settings_path) is True
+
+    def test_a_helper_for_another_proxy_does_not_count(self, tmp_path, lite_on_path):
+        settings_path = tmp_path / "settings.json"
+        _helper_configure("https://other.example.com", settings_path, (), tmp_path / "state.json")
+
+        assert lite_api_key_helper_configured("https://proxy.example.com", settings_path) is False
+
+    def test_a_hand_written_helper_does_not_count(self, tmp_path, lite_on_path):
+        settings_path = self._settings(tmp_path, json.dumps({"apiKeyHelper": "cat ~/.my-proxy-key"}))
+
+        assert lite_api_key_helper_configured("https://proxy.example.com", settings_path) is False
+
+    def test_missing_or_helperless_settings_do_not_count(self, tmp_path, lite_on_path):
+        assert lite_api_key_helper_configured("https://proxy.example.com", tmp_path / "absent.json") is False
+        helperless = json.dumps({"env": {"ANTHROPIC_BASE_URL": "https://proxy.example.com"}})
+        settings_path = self._settings(tmp_path, helperless)
+        assert lite_api_key_helper_configured("https://proxy.example.com", settings_path) is False
+
+    def test_unreadable_settings_fall_back_to_false(self, tmp_path, lite_on_path):
+        settings_path = self._settings(tmp_path, "{not json")
+
+        assert lite_api_key_helper_configured("https://proxy.example.com", settings_path) is False
+
+    def test_lite_missing_from_path_falls_back_to_false(self, tmp_path):
+        helper = "/usr/local/bin/lite --base-url https://proxy.example.com auth print-token"
+        settings_path = self._settings(tmp_path, json.dumps({"apiKeyHelper": helper}))
+        with patch(f"{CLAUDE_SETTINGS_MODULE}.shutil.which", return_value=None):
+            assert lite_api_key_helper_configured("https://proxy.example.com", settings_path) is False
+
+
+class TestMergeClaudeSettings:
+    """One merge for every way Claude Code gets wired: `lite up`, `lite login --config-claude`,
+    `lite configure claude` and `lite autoroute up`."""
+
+    def test_a_static_token_lands_in_env_and_the_helper_slot_is_cleared(self):
+        settings = {"apiKeyHelper": "/usr/local/bin/lite auth print-token", "env": {"ANTHROPIC_API_KEY": "leaked"}}
+        merged = merge_claude_settings(settings, "http://127.0.0.1:4000/", StaticToken("token-abc"))
+        assert merged["env"]["ANTHROPIC_BASE_URL"] == "http://127.0.0.1:4000"
+        assert merged["env"]["ANTHROPIC_AUTH_TOKEN"] == "token-abc"
+        assert merged["env"]["ENABLE_TOOL_SEARCH"] == "true"
+        assert merged["env"]["CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"] == "1"
+        assert "ANTHROPIC_API_KEY" not in merged["env"]
+        assert "apiKeyHelper" not in merged
+        assert "model" not in merged
+        assert not any(key in merged["env"] for key in ANTHROPIC_DEFAULT_MODEL_ENV_KEYS)
+
+    def test_a_helper_lands_top_level_and_the_static_slots_are_cleared(self):
+        settings = {"env": {"ANTHROPIC_AUTH_TOKEN": "sk-old", "ANTHROPIC_API_KEY": "leaked"}}
+        merged = merge_claude_settings(settings, "http://127.0.0.1:4000", ApiKeyHelper("lite auth print-token"))
+        assert merged["apiKeyHelper"] == "lite auth print-token"
+        assert "ANTHROPIC_AUTH_TOKEN" not in merged["env"] and "ANTHROPIC_API_KEY" not in merged["env"]
+
+    def test_keeps_existing_switch_values_and_unrelated_keys_without_mutating_the_input(self):
+        settings = {"theme": "dark", "env": {"SOME_OTHER_VAR": "value", "ENABLE_TOOL_SEARCH": "false"}}
+        merged = merge_claude_settings(settings, "http://127.0.0.1:4000", StaticToken("token-abc"))
+        assert merged["theme"] == "dark"
+        assert merged["env"]["SOME_OTHER_VAR"] == "value"
+        assert merged["env"]["ENABLE_TOOL_SEARCH"] == "false"
+        assert settings == {"theme": "dark", "env": {"SOME_OTHER_VAR": "value", "ENABLE_TOOL_SEARCH": "false"}}
+
+    def test_a_default_model_sets_only_the_row_claude_code_starts_on(self):
+        merged = merge_claude_settings(
+            {}, "http://127.0.0.1:4000", StaticToken("token-abc"), default_model="claude-auto"
+        )
+        assert merged["model"] == "claude-auto"
+        assert not any(key in merged["env"] for key in ANTHROPIC_DEFAULT_MODEL_ENV_KEYS)
+
+    def test_a_tier_model_forces_every_claude_code_tier_as_autoroute_needs(self):
+        # Router's auto-router registry is keyed by the literal requested model string with no
+        # wildcard resolution, so `lite autoroute up` overrides the env var each tier reads.
+        settings = {"env": {"ANTHROPIC_DEFAULT_SONNET_MODEL": "claude-opus-4-8"}}
+        merged = merge_claude_settings(
+            settings, "http://127.0.0.1:4000", StaticToken("token-abc"), tier_model="autorouter"
+        )
+        assert {merged["env"][key] for key in ANTHROPIC_DEFAULT_MODEL_ENV_KEYS} == {"autorouter"}
+        assert "model" not in merged
+
+    def test_touches_exactly_the_declared_owned_keys(self):
+        # The receipt and unconfigure restore exactly OWNED_*_KEYS, so a key the merge writes outside
+        # that table would be written by configure and never undone.
+        settings = {
+            "theme": "dark",
+            "permissions": {"allow": ["Bash"]},
+            "env": {"KEEP_ME": "1", "ANTHROPIC_API_KEY": "old", "ENABLE_TOOL_SEARCH": "false"},
+            "apiKeyHelper": "old-helper",
+            "model": "old-model",
+        }
+        for credential in (StaticToken("token-abc"), ApiKeyHelper("helper")):
+            merged = merge_claude_settings(settings, "http://127.0.0.1:4000", credential, default_model="claude-auto")
+            changed_top_level = {key for key in set(settings) | set(merged) if settings.get(key) != merged.get(key)}
+            assert changed_top_level - {"env"} <= set(OWNED_TOP_LEVEL_KEYS)
+            changed_env = {
+                key
+                for key in set(settings["env"]) | set(merged["env"])
+                if settings["env"].get(key) != merged["env"].get(key)
+            }
+            assert changed_env <= set(OWNED_ENV_KEYS)
+            assert merged["permissions"] == {"allow": ["Bash"]}
+            assert merged["env"]["KEEP_ME"] == "1"
+
+
+PROXY = "http://127.0.0.1:4000"
+ANTHROPIC = "https://api.anthropic.com"
+HELPER = ApiKeyHelper("lite auth print-token")
+ORIGINAL = {
+    "theme": "dark",
+    "permissions": {"allow": ["Bash"]},
+    "env": {"KEEP_ME": "1", "ANTHROPIC_API_KEY": "sk-ant-mine", "ANTHROPIC_BASE_URL": ANTHROPIC},
+    "apiKeyHelper": "/usr/local/bin/lite auth print-token",
+    "model": "claude-opus-5",
+}
+
+
+def _set(path, value):
+    """A user edit: set (or with `_ABSENT`, remove) the key at a dotted path in the settings file."""
+
+    def edit(settings):
+        section, _, key = path.rpartition(".")
+        container = settings.setdefault(section, {}) if section else settings
+        if value is _ABSENT:
+            container.pop(key, None)
+        else:
+            container[key] = value
+        return settings
+
+    return edit
+
+
+_ABSENT = object()
+
+
+class _Rig:
+    """One settings file plus receipt under tmp_path, driven through the public functions only."""
+
+    def __init__(self, tmp_path, initial):
+        self.settings = tmp_path / "claude" / "settings.json"
+        self.state = tmp_path / "state" / "claude_configure_state.json"
+        if initial is not None:
+            self.settings.parent.mkdir(parents=True)
+            self.settings.write_text(json.dumps(initial))
+
+    def read(self):
+        return json.loads(self.settings.read_text()) if self.settings.exists() else None
+
+    def configure(self, credential=StaticToken("sk-virtual-key"), model=StartOn("claude-auto"), **kwargs):
+        configure_claude_settings(PROXY, credential, model, self.settings, self.state, (), **kwargs)
+
+    def edit(self, *edits):
+        settings = self.read()
+        for apply in edits:
+            settings = apply(settings)
+        self.settings.write_text(json.dumps(settings))
+
+    def unconfigure(self):
+        return unconfigure_claude_settings(self.settings, self.state, ())
+
+
+# Each row: initial file, steps (configure kwargs dicts or edit callables) between the first configure
+# and unconfigure, the expected file afterwards, and the expected outcome fields. Sequences that used
+# to be one test each; the receipt's rules are what make them all come out right.
+UNDO_SCENARIOS = {
+    "plain round trip": (ORIGINAL, [], ORIGINAL, {"kept": ()}),
+    "no file before": (None, [], None, {"file_removed": True}),
+    "no env before": ({"theme": "dark"}, [], {"theme": "dark"}, {}),
+    "null env before": ({"theme": "dark", "env": None}, [], {"theme": "dark", "env": None}, {}),
+    "empty env before": ({"theme": "dark", "env": {}}, [], {"theme": "dark", "env": {}}, {}),
+    "user edits stay and are named": (
+        ORIGINAL,
+        [_set("env.ENABLE_TOOL_SEARCH", "false"), _set("model", "claude-sonnet-4-6")],
+        {**ORIGINAL, "env": {**ORIGINAL["env"], "ENABLE_TOOL_SEARCH": "false"}, "model": "claude-sonnet-4-6"},
+        {"kept": {"env.ENABLE_TOOL_SEARCH", "model"}, "withheld": ()},
+    ),
+    "user filled an env configure created": (None, [_set("env.MY_VAR", "mine")], {"env": {"MY_VAR": "mine"}}, {}),
+    "user deleted the file": (None, [lambda s: None], None, {"file_removed": True, "restored": (), "kept": ()}),
+    "user removed our key: neither restored nor kept": (
+        ORIGINAL,
+        [_set("env.ANTHROPIC_AUTH_TOKEN", _ABSENT)],
+        ORIGINAL,
+        {"not_restored": {"env.ANTHROPIC_AUTH_TOKEN"}, "kept": ()},
+    ),
+    "restored names only what changed": (
+        {"model": "claude-opus-5"},
+        [],
+        {"model": "claude-opus-5"},
+        {
+            "restored": {
+                "env.ANTHROPIC_BASE_URL",
+                "env.ENABLE_TOOL_SEARCH",
+                "env.CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY",
+                "apiKeyHelper",
+            },
+            "kept": (),
+        },
+        {"credential": HELPER, "model": KeepModel()},
+    ),
+    "repeat across credential kinds keeps the first snapshot": (
+        ORIGINAL,
+        [
+            {"credential": HELPER, "model": UnpinModel()},
+            {"credential": StaticToken("sk-rotated"), "model": StartOn("claude-sonnet-4-6")},
+        ],
+        ORIGINAL,
+        {},
+    ),
+    "repeat without a model lets go of our pin, user had none": ({}, [{"model": UnpinModel()}], {}, {}),
+    "repeat without a model lets go of our pin, user had one": (
+        {"model": "claude-opus-5"},
+        [{"model": UnpinModel()}],
+        {"model": "claude-opus-5"},
+        {},
+    ),
+    "re-login keeps our pin": (None, [{"credential": HELPER, "model": KeepModel()}], None, {"file_removed": True}),
+    "edit between configures survives an unpin repeat": (
+        ORIGINAL,
+        [
+            _set("model", "my-favourite"),
+            _set("env.ENABLE_TOOL_SEARCH", "false"),
+            {"credential": HELPER, "model": UnpinModel()},
+        ],
+        {**ORIGINAL, "env": {**ORIGINAL["env"], "ENABLE_TOOL_SEARCH": "false"}, "model": "my-favourite"},
+        {"kept": {"env.ENABLE_TOOL_SEARCH", "model"}},
+    ),
+    "edit between configures survives a re-login": (
+        ORIGINAL,
+        [
+            _set("model", "my-favourite"),
+            _set("env.ENABLE_TOOL_SEARCH", "false"),
+            {"credential": HELPER, "model": KeepModel()},
+        ],
+        {**ORIGINAL, "env": {**ORIGINAL["env"], "ENABLE_TOOL_SEARCH": "false"}, "model": "my-favourite"},
+        {"kept": {"env.ENABLE_TOOL_SEARCH", "model"}},
+    ),
+    "edit between configures: a same-model repeat displaces it, so it is what comes back": (
+        ORIGINAL,
+        [_set("model", "my-favourite"), _set("env.ENABLE_TOOL_SEARCH", "false"), {"credential": HELPER}],
+        {**ORIGINAL, "env": {**ORIGINAL["env"], "ENABLE_TOOL_SEARCH": "false"}, "model": "my-favourite"},
+        {"kept": {"env.ENABLE_TOOL_SEARCH"}, "restored_includes": {"model"}},
+    ),
+    "base URL changed since: credentials withheld, receipt kept": (
+        ORIGINAL,
+        [_set("env.ANTHROPIC_BASE_URL", "http://other-proxy:4000")],
+        {**ORIGINAL, "env": {"KEEP_ME": "1", "ANTHROPIC_BASE_URL": "http://other-proxy:4000"}, "apiKeyHelper": _ABSENT},
+        {
+            "withheld": {("env.ANTHROPIC_API_KEY", ANTHROPIC), ("apiKeyHelper", ANTHROPIC)},
+            "kept": {"env.ANTHROPIC_BASE_URL"},
+            "receipt_kept": True,
+        },
+    ),
+    "base URL changed and back: judged against the URL the restored file holds": (
+        ORIGINAL,
+        [_set("env.ANTHROPIC_BASE_URL", ANTHROPIC)],
+        ORIGINAL,
+        {"withheld": ()},
+    ),
+    "credential captured beside no URL goes back only beside no URL": (
+        {"env": {"ANTHROPIC_API_KEY": "sk-default-endpoint"}},
+        [_set("env.ANTHROPIC_BASE_URL", "http://other-proxy:4000")],
+        {"env": {"ANTHROPIC_BASE_URL": "http://other-proxy:4000"}},
+        {
+            "withheld": {("env.ANTHROPIC_API_KEY", "no ANTHROPIC_BASE_URL (Anthropic's default endpoint)")},
+            "receipt_kept": True,
+        },
+    ),
+    "restored document empty while a credential is withheld: file goes, receipt stays": (
+        None,
+        [
+            _set("env.ANTHROPIC_API_KEY", "sk-user"),
+            {"credential": HELPER, "model": KeepModel()},
+            _set("env.ANTHROPIC_BASE_URL", _ABSENT),
+        ],
+        None,
+        {"withheld": {("env.ANTHROPIC_API_KEY", PROXY)}, "file_removed": True, "receipt_kept": True},
+        {"credential": HELPER, "model": KeepModel()},
+    ),
+    "a credential the user changed is kept, never also withheld": (
+        ORIGINAL,
+        [_set("env.ANTHROPIC_BASE_URL", "http://other-proxy:4000"), _set("apiKeyHelper", "/opt/mine/helper")],
+        {
+            **ORIGINAL,
+            "env": {"KEEP_ME": "1", "ANTHROPIC_BASE_URL": "http://other-proxy:4000"},
+            "apiKeyHelper": "/opt/mine/helper",
+        },
+        {
+            "withheld": {("env.ANTHROPIC_API_KEY", ANTHROPIC)},
+            "kept": {"env.ANTHROPIC_BASE_URL", "apiKeyHelper"},
+            "receipt_kept": True,
+        },
+    ),
+}
+
+
+def _expected_file(expected):
+    if expected is None:
+        return None
+    return {k: v for k, v in expected.items() if v is not _ABSENT}
+
+
+class TestConfigureAndUnconfigure:
+    """`configure_claude_settings` records how to undo itself; `unconfigure_claude_settings` undoes only that."""
+
+    @pytest.mark.parametrize("scenario", UNDO_SCENARIOS.values(), ids=UNDO_SCENARIOS.keys())
+    def test_undo_matrix(self, tmp_path, scenario):
+        initial, steps, expected, outcome_expectations, *first = scenario
+        rig = _Rig(tmp_path, initial)
+        rig.configure(**(first[0] if first else {}))
+        for step in steps:
+            if isinstance(step, dict):
+                rig.configure(**step)
+            elif rig.settings.exists() and step(json.loads(rig.settings.read_text())) is None:
+                rig.settings.unlink()
+            else:
+                rig.edit(step)
+
+        outcome = rig.unconfigure()
+
+        assert rig.read() == _expected_file(expected)
+        assert rig.state.exists() == outcome_expectations.get("receipt_kept", False)
+        for field, want in outcome_expectations.items():
+            if field == "withheld":
+                assert {(item.key, item.endpoint) for item in outcome.withheld} == set(want)
+            elif field == "not_restored":
+                assert not set(want) & set(outcome.restored) and not set(want) & set(outcome.kept)
+            elif field == "restored_includes":
+                assert set(want) <= set(outcome.restored)
+            elif field in ("restored", "kept"):
+                assert set(getattr(outcome, field)) == set(want)
+            elif field != "receipt_kept":
+                assert getattr(outcome, field) == want
+        assert not {item.key for item in outcome.withheld} & set(outcome.kept)
+
+    def test_configure_writes_owner_only_and_the_receipt_never_holds_the_key(self, tmp_path):
+        rig = _Rig(tmp_path, ORIGINAL)
+        rig.configure(credential=StaticToken("sk-virtual-key-never-on-disk-twice"))
+        configured = rig.read()
+        assert configured["env"]["ANTHROPIC_AUTH_TOKEN"] == "sk-virtual-key-never-on-disk-twice"
+        assert configured["env"]["ANTHROPIC_BASE_URL"] == PROXY and configured["model"] == "claude-auto"
+        assert "ANTHROPIC_API_KEY" not in configured["env"] and "apiKeyHelper" not in configured
+        assert stat.S_IMODE(rig.settings.stat().st_mode) == 0o600 == stat.S_IMODE(rig.state.stat().st_mode)
+        assert "sk-virtual-key-never-on-disk-twice" not in rig.state.read_text()
+
+    def test_withheld_credentials_come_back_once_the_url_points_at_their_server_again(self, tmp_path):
+        # The kept receipt owns only the withheld slots: the second unconfigure restores exactly those.
+        rig = _Rig(tmp_path, ORIGINAL)
+        rig.configure()
+        rig.edit(_set("env.ANTHROPIC_BASE_URL", "http://other-proxy:4000"))
+        rig.unconfigure()
+        rig.edit(_set("env.ANTHROPIC_BASE_URL", ANTHROPIC), _set("theme", "light"))
+        outcome = rig.unconfigure()
+        assert rig.read() == {**ORIGINAL, "theme": "light"}
+        assert set(outcome.restored) == {"env.ANTHROPIC_API_KEY", "apiKeyHelper"}
+        assert outcome.kept == () and outcome.withheld == () and not rig.state.exists()
+
+    @pytest.mark.parametrize(
+        ("path", "value", "repeat_credential"),
+        [
+            ("env.ANTHROPIC_API_KEY", "sk-user-added-later", HELPER),
+            ("env.ANTHROPIC_AUTH_TOKEN", "sk-users-own-token", HELPER),
+            ("apiKeyHelper", "/opt/mine/helper", StaticToken("sk-rotated")),
+        ],
+        ids=["user-adds-api-key", "user-replaces-our-token", "user-sets-own-helper"],
+    )
+    def test_a_credential_the_user_set_between_two_configures_is_what_comes_back(
+        self, tmp_path, path, value, repeat_credential
+    ):
+        # The repeat's merge clears the slot, so the displaced value is snapshotted and is what returns;
+        # it was set while the file pointed at the proxy, so it returns once the file points there again.
+        rig = _Rig(tmp_path, {"theme": "dark"})
+        rig.configure(credential=HELPER, model=KeepModel())
+        rig.edit(_set(path, value))
+        rig.configure(credential=repeat_credential, model=KeepModel())
+        assert not _lookup(rig.read(), path)
+
+        outcome = rig.unconfigure()
+        assert [(item.key, item.endpoint) for item in outcome.withheld] == [(path, PROXY)]
+        assert rig.read() == {"theme": "dark"} and rig.state.exists()
+        rig.settings.write_text(json.dumps({"theme": "dark", "env": {"ANTHROPIC_BASE_URL": PROXY}}))
+        outcome = rig.unconfigure()
+        assert _lookup(rig.read(), path) == value
+        assert outcome.restored == (path,) and outcome.withheld == () and not rig.state.exists()
+
+    def test_a_receipt_commit_that_fails_leaves_no_staged_token_behind(self, tmp_path):
+        rig = _Rig(tmp_path, {})
+
+        def commit_receipt_fails(staged, path):
+            if path == str(rig.state):
+                os.unlink(staged)
+                raise OSError("receipt rename failed")
+            commit_staged_json(staged, path)
+
+        with pytest.raises(ClaudeSettingsError, match=r"Could not write .*receipt rename failed"):
+            rig.configure(credential=StaticToken("sk-never-left-in-a-temp-file"), commit=commit_receipt_fails)
+        assert not list(rig.settings.parent.glob(".tmp-*")) and not list(rig.state.parent.glob(".tmp-*"))
+        assert rig.read() == {} and not rig.state.exists()
+
+    @pytest.mark.parametrize("configured_before", [False, True], ids=["first-configure", "repeat-configure"])
+    def test_a_settings_commit_that_fails_after_the_receipt_landed_puts_the_receipt_back(
+        self, tmp_path, configured_before
+    ):
+        # The two renames are not atomic: a settings rename that fails after the receipt landed must
+        # not leave a receipt describing settings that were never written.
+        rig = _Rig(tmp_path, ORIGINAL)
+        if configured_before:
+            rig.configure()
+        receipt_before = rig.state.read_text() if configured_before else None
+        settings_before = rig.settings.read_text()
+
+        def commit_settings_fails(staged, path):
+            if path == str(rig.settings):
+                os.unlink(staged)
+                raise OSError("rename failed")
+            commit_staged_json(staged, path)
+
+        with pytest.raises(ClaudeSettingsError, match="rename failed"):
+            rig.configure(credential=StaticToken("sk-rotated"), commit=commit_settings_fails)
+        assert rig.settings.read_text() == settings_before
+        assert (rig.state.read_text() if rig.state.exists() else None) == receipt_before
+        if configured_before:
+            rig.unconfigure()
+            assert rig.read() == ORIGINAL
+
+    def test_a_failed_repeat_configure_leaves_the_earlier_undo_intact(self, tmp_path):
+        rig = _Rig(tmp_path, ORIGINAL)
+        rig.configure()
+        receipt_before = rig.state.read_text()
+        rig.settings.parent.chmod(0o500)
+        try:
+            with pytest.raises(ClaudeSettingsError, match="Could not write"):
+                rig.configure(credential=StaticToken("sk-rotated"))
+        finally:
+            rig.settings.parent.chmod(0o700)
+        assert rig.state.read_text() == receipt_before and not list(rig.state.parent.glob(".tmp-*"))
+        assert rig.read()["env"]["ANTHROPIC_AUTH_TOKEN"] == "sk-virtual-key"
+        rig.unconfigure()
+        assert rig.read() == ORIGINAL
+
+    def test_unconfigure_reports_a_receipt_it_cannot_remove_as_a_settings_error(self, tmp_path):
+        rig = _Rig(tmp_path, ORIGINAL)
+        rig.configure()
+        rig.state.parent.chmod(0o500)
+        try:
+            with pytest.raises(ClaudeSettingsError, match="Could not remove"):
+                rig.unconfigure()
+        finally:
+            rig.state.parent.chmod(0o700)
+
+    def test_configure_writes_through_a_symlinked_settings_file(self, tmp_path):
+        target = tmp_path / "dotfiles" / "settings.json"
+        target.parent.mkdir()
+        target.write_text(json.dumps({"theme": "dark"}))
+        link = tmp_path / "settings.json"
+        link.symlink_to(target)
+        configure_claude_settings(PROXY, StaticToken("sk-virtual-key"), UnpinModel(), link, tmp_path / "state.json", ())
+        assert link.is_symlink()
+        assert json.loads(target.read_text())["env"]["ANTHROPIC_AUTH_TOKEN"] == "sk-virtual-key"
+
+    @pytest.mark.parametrize("operation", ["configure", "unconfigure"])
+    def test_refuses_while_a_temporary_owner_holds_a_backup(self, paths, tmp_path, operation):
+        settings_path, backup_path = paths
+        backup_path.write_text("{}")
+        owners = _owners(backup_path)
+        state = tmp_path / "state.json"
+        attempt = (
+            (lambda: configure_claude_settings(PROXY, StaticToken("k"), UnpinModel(), settings_path, state, owners))
+            if operation == "configure"
+            else (lambda: unconfigure_claude_settings(settings_path, state, owners))
+        )
+        with pytest.raises(ClaudeSettingsError, match="lite down"):
+            attempt()
+        assert not settings_path.exists()
+
+    def test_unconfigure_without_a_receipt_is_an_error_not_a_silent_no_op(self, tmp_path):
+        with pytest.raises(ClaudeSettingsError, match="nothing to undo"):
+            _Rig(tmp_path, None).unconfigure()
+
+
+def _lookup(settings, path):
+    section, _, key = path.rpartition(".")
+    return (settings.get(section) or {}).get(key) if section else settings.get(key)
diff --git a/tests/test_litellm/proxy/client/cli/test_configure_commands.py b/tests/test_litellm/proxy/client/cli/test_configure_commands.py
new file mode 100644
index 00000000000..ac7408339fe
--- /dev/null
+++ b/tests/test_litellm/proxy/client/cli/test_configure_commands.py
@@ -0,0 +1,431 @@
+import json
+import os
+import stat
+
+import click
+import pytest
+import requests
+import responses
+from click.testing import CliRunner
+
+from litellm.proxy.client.cli import cli
+from litellm.proxy.client.cli.commands import claude_settings as claude_settings_module
+from litellm.proxy.client.cli.commands import configure as configure_module
+from litellm.proxy.client.cli.commands.claude_settings import SettingsFileOwner
+from litellm.proxy.client.cli.commands.configure import configure_claude, configure_group, interactive_configure
+
+PROXY = "http://proxy.test:4000"
+VALID_KEY = "sk-virtual-key"
+LISTED_MODELS = ("claude-auto", "gpt-5.6-luna")
+
+
+def _mock_models():
+    responses.get(
+        f"{PROXY}/v1/models",
+        json={"data": [{"id": model, "object": "model"} for model in LISTED_MODELS]},
+        match=[responses.matchers.header_matcher({"Authorization": f"Bearer {VALID_KEY}"})],
+    )
+    responses.get(f"{PROXY}/v1/models", status=401)
+
+
+@pytest.fixture
+def paths(monkeypatch, tmp_path):
+    """The default settings file, reached the way Claude Code reaches it: CLAUDE_CONFIG_DIR names its directory."""
+    settings_path = tmp_path / "claude" / "settings.json"
+    state_path = tmp_path / "litellm" / "claude_configure_state.json"
+    monkeypatch.setenv("CLAUDE_CONFIG_DIR", str(settings_path.parent))
+    monkeypatch.setattr(claude_settings_module, "CLAUDE_SETTINGS_PATH", settings_path)
+    monkeypatch.setattr(claude_settings_module, "CONFIGURE_STATE_PATH", state_path)
+    return settings_path, state_path
+
+
+@pytest.fixture
+def lite_on_path(monkeypatch, tmp_path):
+    """A real `lite` executable on PATH, so the apiKeyHelper command resolves without patching."""
+    bin_dir = tmp_path / "bin"
+    bin_dir.mkdir()
+    lite = bin_dir / "lite"
+    lite.write_text("#!/bin/sh\nexit 0\n")
+    lite.chmod(lite.stat().st_mode | stat.S_IXUSR)
+    monkeypatch.setenv("PATH", f"{bin_dir}{os.pathsep}{os.environ.get('PATH', '')}")
+    return str(lite)
+
+
+@pytest.fixture
+def runner():
+    return CliRunner()
+
+
+@pytest.fixture
+def lite_up_backup(monkeypatch, tmp_path):
+    """A `lite up` session holding its backup, the local precondition every settings write refuses on."""
+    backup = tmp_path / "claude_settings_backup.json"
+    backup.write_text("{}")
+    monkeypatch.setattr(
+        claude_settings_module, "SETTINGS_FILE_OWNERS", (SettingsFileOwner(backup, "lite up", "lite down"),)
+    )
+    return backup
+
+
+def _configure(runner, *args):
+    return runner.invoke(cli, ["--base-url", PROXY, "configure", "claude", *args])
+
+
+class TestConfigureClaudeWithAVirtualKey:
+    @responses.activate
+    def test_writes_settings_and_reports_without_echoing_the_key(self, runner, paths):
+        _mock_models()
+        settings_path, state_path = paths
+        result = _configure(runner, "--api-key", VALID_KEY, "--model", "claude-auto")
+        assert result.exit_code == 0, result.output
+        written = json.loads(settings_path.read_text())
+        assert written["env"]["ANTHROPIC_BASE_URL"] == PROXY
+        assert written["env"]["ANTHROPIC_AUTH_TOKEN"] == VALID_KEY
+        assert written["env"]["CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"] == "1"
+        assert written["model"] == "claude-auto"
+        assert "ANTHROPIC_DEFAULT_SONNET_MODEL" not in written["env"]
+        assert state_path.exists()
+        assert VALID_KEY not in result.output
+        assert "Starting model: claude-auto" in result.output
+        assert "1 of the proxy's 2 models" in result.output
+        assert "lite unconfigure claude" in result.output
+        assert [call.request.headers.get("x-gateway-client") for call in responses.calls] == ["claude-code"]
+
+    @responses.activate
+    def test_takes_the_key_from_the_global_option_and_keeps_claude_codes_default(self, runner, paths):
+        _mock_models()
+        settings_path, _ = paths
+        result = runner.invoke(cli, ["--base-url", PROXY, "--api-key", VALID_KEY, "configure", "claude"])
+        assert result.exit_code == 0, result.output
+        written = json.loads(settings_path.read_text())
+        assert written["env"]["ANTHROPIC_AUTH_TOKEN"] == VALID_KEY
+        assert "model" not in written
+        assert "Starting model: not pinned" in result.output
+
+    @responses.activate
+    def test_refuses_a_model_the_proxy_does_not_list(self, runner, paths):
+        _mock_models()
+        settings_path, _ = paths
+        result = _configure(runner, "--api-key", VALID_KEY, "--model", "claude-nope")
+        assert result.exit_code != 0
+        assert "'claude-nope' is not served" in result.output
+        assert "claude-auto, gpt-5.6-luna" in result.output
+        assert not settings_path.exists()
+
+    @responses.activate
+    def test_refuses_a_key_the_proxy_rejects(self, runner, paths):
+        _mock_models()
+        settings_path, _ = paths
+        result = _configure(runner, "--api-key", "sk-wrong")
+        assert result.exit_code != 0
+        assert "rejected your key (HTTP 401)" in result.output
+        assert not settings_path.exists()
+
+    @responses.activate
+    @pytest.mark.parametrize(
+        ("mock", "expected", "unexpected"),
+        [
+            (
+                lambda: responses.get(f"{PROXY}/v1/models", body=requests.ConnectionError("refused")),
+                "Is the proxy at",
+                "answered",
+            ),
+            (
+                lambda: responses.get(f"{PROXY}/v1/models", status=500),
+                "The proxy at http://proxy.test:4000 answered",
+                "Is the proxy at",
+            ),
+            (
+                lambda: responses.get(f"{PROXY}/v1/models", body="<html>not json</html>"),
+                "answered, so check that it is a LiteLLM proxy",
+                "Is the proxy at",
+            ),
+            (
+                lambda: responses.get(f"{PROXY}/v1/models", json={"data": []}),
+                "Claude Code would have nothing to run",
+                "Is the proxy at",
+            ),
+        ],
+        ids=["unreachable", "http-500", "non-json-body", "empty-list"],
+    )
+    def test_the_listing_hint_matches_how_the_listing_failed(self, runner, paths, mock, expected, unexpected):
+        # Only a proxy that never answered gets the "is it running" question; a 500, a non-JSON body or an
+        # empty list prove it is up, and the hint says so instead.
+        mock()
+        settings_path, _ = paths
+        result = _configure(runner, "--api-key", VALID_KEY)
+        assert result.exit_code != 0
+        assert expected in result.output and unexpected not in result.output
+        assert not settings_path.exists()
+
+    @responses.activate
+    @pytest.mark.parametrize("entry", ["virtual-key", "login", "interactive"])
+    def test_refuses_while_lite_up_holds_a_backup_before_any_login_or_request(
+        self, runner, paths, monkeypatch, lite_up_backup, entry
+    ):
+        _mock_models()
+
+        def login_must_not_run(ctx):
+            raise AssertionError("the local precondition must be checked before a login is attempted")
+
+        monkeypatch.setattr(configure_module, "ensure_fresh_login", login_must_not_run)
+        if entry == "interactive":
+            ctx = click.Context(configure_group, obj={"base_url": PROXY, "api_key": None})
+            with pytest.raises(click.ClickException, match="lite down"):
+                interactive_configure(ctx, pick_targets=lambda: ("claude",), pick_model=lambda listed: None)
+        else:
+            args = ["--api-key", VALID_KEY] if entry == "virtual-key" else []
+            result = runner.invoke(configure_claude, args, obj={"base_url": PROXY, "api_key": None})
+            assert result.exit_code != 0 and "lite down" in result.output
+        assert len(responses.calls) == 0
+        assert not paths[0].exists()
+
+    @responses.activate
+    def test_says_so_when_the_key_is_written_through_a_symlink(self, runner, paths, tmp_path):
+        _mock_models()
+        settings_path, _ = paths
+        target = tmp_path / "dotfiles" / "settings.json"
+        target.parent.mkdir()
+        target.write_text("{}")
+        settings_path.parent.mkdir(parents=True)
+        settings_path.symlink_to(target)
+        result = _configure(runner, "--api-key", VALID_KEY)
+        assert result.exit_code == 0, result.output
+        assert "keep it out of version control" in result.output
+        assert json.loads(target.read_text())["env"]["ANTHROPIC_AUTH_TOKEN"] == VALID_KEY
+
+
+class TestConfigureClaudeWithTheLogin:
+    def _stored_login(self, monkeypatch):
+        monkeypatch.setattr(configure_module, "ensure_fresh_login", lambda ctx: None)
+        monkeypatch.setattr(configure_module, "get_stored_api_key", lambda expected_base_url, vault: VALID_KEY)
+
+    @responses.activate
+    def test_uses_the_login_through_the_helper_and_writes_no_secret(self, runner, paths, monkeypatch, lite_on_path):
+        _mock_models()
+        self._stored_login(monkeypatch)
+        settings_path, _ = paths
+        result = runner.invoke(
+            configure_claude,
+            ["--model", "claude-auto"],
+            obj={"base_url": PROXY, "api_key": VALID_KEY, "api_key_from_token_file": True},
+        )
+        assert result.exit_code == 0, result.output
+        written = json.loads(settings_path.read_text())
+        assert written["apiKeyHelper"] == f"{lite_on_path} --base-url {PROXY} auth print-token"
+        assert "ANTHROPIC_AUTH_TOKEN" not in written["env"]
+        assert written["model"] == "claude-auto"
+        assert VALID_KEY not in settings_path.read_text()
+        assert "read through apiKeyHelper" in result.output
+
+    @responses.activate
+    def test_an_explicit_key_still_wins_over_a_stored_login(self, runner, paths, monkeypatch, lite_on_path):
+        _mock_models()
+        self._stored_login(monkeypatch)
+        settings_path, _ = paths
+        result = runner.invoke(
+            configure_claude,
+            ["--api-key", VALID_KEY],
+            obj={"base_url": PROXY, "api_key": "sk-login-jwt", "api_key_from_token_file": True},
+        )
+        assert result.exit_code == 0, result.output
+        written = json.loads(settings_path.read_text())
+        assert written["env"]["ANTHROPIC_AUTH_TOKEN"] == VALID_KEY and "apiKeyHelper" not in written
+
+
+class TestInteractiveConfigure:
+    @responses.activate
+    def test_asks_for_targets_and_a_starting_model_then_configures(self, paths):
+        _mock_models()
+        settings_path, _ = paths
+        asked = {}
+
+        def pick_model(listed):
+            asked["listed"] = tuple(listed)
+            return "claude-auto"
+
+        ctx = click.Context(
+            configure_group, obj={"base_url": PROXY, "api_key": VALID_KEY, "api_key_from_token_file": False}
+        )
+        interactive_configure(ctx, pick_targets=lambda: ("claude",), pick_model=pick_model)
+        assert asked["listed"] == LISTED_MODELS
+        assert json.loads(settings_path.read_text())["model"] == "claude-auto"
+
+    def test_does_nothing_when_claude_code_is_not_picked(self, paths):
+        settings_path, _ = paths
+        ctx = click.Context(
+            configure_group, obj={"base_url": PROXY, "api_key": VALID_KEY, "api_key_from_token_file": False}
+        )
+        interactive_configure(ctx, pick_targets=lambda: (), pick_model=lambda listed: None)
+        assert not settings_path.exists()
+
+    def test_bare_configure_without_a_terminal_names_the_non_interactive_command(self, runner, paths):
+        result = runner.invoke(cli, ["--base-url", PROXY, "configure"])
+        assert result.exit_code != 0
+        assert "lite configure claude --api-key" in result.output
+
+
+class TestUnconfigureClaude:
+    @responses.activate
+    def test_restores_the_original_file_and_removes_the_receipt(self, runner, paths):
+        _mock_models()
+        settings_path, state_path = paths
+        settings_path.parent.mkdir(parents=True)
+        original = {"theme": "dark", "model": "claude-opus-5"}
+        settings_path.write_text(json.dumps(original))
+        assert _configure(runner, "--api-key", VALID_KEY, "--model", "claude-auto").exit_code == 0
+
+        result = runner.invoke(cli, ["unconfigure", "claude"])
+        assert result.exit_code == 0, result.output
+        assert json.loads(settings_path.read_text()) == original
+        assert not state_path.exists()
+        assert "Restored in" in result.output and "model" in result.output
+        assert "ANTHROPIC_API_KEY" not in result.output, "a key that never existed was not restored"
+
+    @responses.activate
+    def test_a_file_only_configure_created_is_reported_removed_not_restored(self, runner, paths):
+        _mock_models()
+        settings_path, _ = paths
+        assert _configure(runner, "--api-key", VALID_KEY).exit_code == 0
+        result = runner.invoke(cli, ["unconfigure", "claude"])
+        assert result.exit_code == 0, result.output
+        assert not settings_path.exists()
+        assert "No settings file remains" in result.output and "Restored" not in result.output
+
+    @responses.activate
+    def test_says_when_nothing_was_still_ours_and_names_what_it_kept(self, runner, paths):
+        _mock_models()
+        settings_path, _ = paths
+        settings_path.parent.mkdir(parents=True)
+        settings_path.write_text(json.dumps({"theme": "dark"}))
+        assert _configure(runner, "--api-key", VALID_KEY, "--model", "claude-auto").exit_code == 0
+        edited = json.loads(settings_path.read_text())
+        edited["env"] = {key: f"{value}-edited" for key, value in edited["env"].items()}
+        edited["model"] = "mine"
+        settings_path.write_text(json.dumps(edited))
+        result = runner.invoke(cli, ["unconfigure", "claude"])
+        assert result.exit_code == 0, result.output
+        assert "Nothing in" in result.output and "was still ours to restore" in result.output
+        assert "Left as you changed them since:" in result.output and "model" in result.output
+
+    @responses.activate
+    def test_names_the_server_a_withheld_credential_was_captured_with_and_keeps_the_receipt(self, runner, paths):
+        _mock_models()
+        settings_path, state_path = paths
+        settings_path.parent.mkdir(parents=True)
+        settings_path.write_text(
+            json.dumps({"env": {"ANTHROPIC_BASE_URL": "https://api.anthropic.com", "ANTHROPIC_API_KEY": "sk-ant"}})
+        )
+        assert _configure(runner, "--api-key", VALID_KEY).exit_code == 0
+        edited = json.loads(settings_path.read_text())
+        edited["env"]["ANTHROPIC_BASE_URL"] = "http://other-proxy:4000"
+        settings_path.write_text(json.dumps(edited))
+        result = runner.invoke(cli, ["unconfigure", "claude"])
+        assert result.exit_code == 0, result.output
+        assert "env.ANTHROPIC_API_KEY (captured with https://api.anthropic.com)" in result.output
+        assert str(state_path) in result.output and state_path.exists()
+        assert "sk-ant" not in result.output
+
+    def test_refuses_while_lite_up_holds_a_backup(self, runner, paths, lite_up_backup):
+        result = runner.invoke(cli, ["unconfigure", "claude"])
+        assert result.exit_code != 0 and "lite down" in result.output
+
+    @responses.activate
+    def test_a_config_dir_is_configured_and_undone_apart_from_the_default_file(
+        self, runner, paths, monkeypatch, tmp_path, lite_up_backup
+    ):
+        _mock_models()
+        default_settings, default_state = paths
+        work_dir = tmp_path / "claude-work"
+        work_dir.mkdir()
+        original = {"theme": "dark"}
+        (work_dir / "settings.json").write_text(json.dumps(original))
+        monkeypatch.setenv("CLAUDE_CONFIG_DIR", str(work_dir))
+
+        configured = _configure(runner, "--api-key", VALID_KEY, "--model", "claude-auto")
+        assert configured.exit_code == 0, configured.output
+        assert f"Configured Claude Code: {work_dir / 'settings.json'}" in configured.output
+        assert json.loads((work_dir / "settings.json").read_text())["env"]["ANTHROPIC_AUTH_TOKEN"] == VALID_KEY
+        assert not default_settings.exists() and not default_state.exists()
+
+        undone = runner.invoke(cli, ["unconfigure", "claude"])
+        assert undone.exit_code == 0, undone.output
+        assert json.loads((work_dir / "settings.json").read_text()) == original
+        assert not default_settings.exists() and not default_state.exists()
+        assert runner.invoke(cli, ["unconfigure", "claude"]).exit_code != 0, "the receipt is gone with the undo"
+
+    def test_without_a_receipt_it_fails_loudly(self, runner, paths):
+        result = runner.invoke(cli, ["unconfigure", "claude"])
+        assert result.exit_code != 0
+        assert "nothing to undo" in result.output
+
+
+class TestClaudeCodeView:
+    VIEW = {"anthropic-version": "2023-06-01", "x-gateway-client": "claude-code"}
+
+    def _mock(self, rows):
+        responses.get(
+            f"{PROXY}/v1/models",
+            json={"data": rows},
+            match=[responses.matchers.header_matcher({"Authorization": f"Bearer {VALID_KEY}", **self.VIEW})],
+        )
+
+    @responses.activate
+    @pytest.mark.parametrize(
+        "model, pinned",
+        [
+            ("literal-claude-router-source", "emitted-literal"),
+            ("marked-sibling", "emitted-marked[1m]"),
+            ("emitted-collision", "emitted-source-priority"),
+            ("emitted-only", "emitted-only"),
+        ],
+    )
+    def test_pins_source_identity_before_emitted_id(self, runner, paths, model, pinned):
+        self._mock(
+            [
+                {"id": "emitted-collision", "source_model": "other-source"},
+                {"id": "emitted-source-priority", "source_model": "emitted-collision"},
+                {"id": "emitted-marked[1m]", "source_model": "marked-sibling"},
+                {"id": "emitted-literal", "source_model": "literal-claude-router-source"},
+                {"id": "emitted-only"},
+            ]
+        )
+        settings_path, _ = paths
+        result = _configure(runner, "--api-key", VALID_KEY, "--model", model)
+        assert result.exit_code == 0, result.output
+        assert json.loads(settings_path.read_text())["model"] == pinned
+        assert f"Starting model: {pinned}" in result.output
+        assert len(responses.calls) == 1
+
+    @responses.activate
+    def test_refuses_unknown_short_suffix(self, runner, paths):
+        self._mock([{"id": "emitted-router-source", "source_model": "literal-router-source"}])
+        settings_path, _ = paths
+        result = _configure(runner, "--api-key", VALID_KEY, "--model", "source")
+        assert result.exit_code != 0
+        assert "'source' is not served" in result.output
+        assert not settings_path.exists()
+
+    @responses.activate
+    def test_interactive_picker_uses_source_names(self, paths):
+        self._mock([{"id": "emitted", "source_model": "source"}])
+        settings_path, _ = paths
+        asked = {}
+        ctx = click.Context(
+            configure_group, obj={"base_url": PROXY, "api_key": VALID_KEY, "api_key_from_token_file": False}
+        )
+
+        def pick_model(listed):
+            asked["listed"] = tuple(listed)
+            return "source"
+
+        interactive_configure(ctx, pick_targets=lambda: ("claude",), pick_model=pick_model)
+        assert asked["listed"] == ("source",)
+        assert json.loads(settings_path.read_text())["model"] == "emitted"
+
+    @responses.activate
+    def test_counts_what_an_older_proxy_lets_the_picker_show(self, runner, paths):
+        _mock_models()
+        result = _configure(runner, "--api-key", VALID_KEY)
+        assert result.exit_code == 0, result.output
+        assert "/model will list 1 of the proxy's 2 models: Claude Code shows only ids containing" in result.output
diff --git a/tests/test_litellm/proxy/client/cli/test_global_options.py b/tests/test_litellm/proxy/client/cli/test_global_options.py
index 0dd388919a5..b73d1acc6e3 100644
--- a/tests/test_litellm/proxy/client/cli/test_global_options.py
+++ b/tests/test_litellm/proxy/client/cli/test_global_options.py
@@ -7,8 +7,6 @@ from unittest.mock import Mock, patch
 import pytest
 from click.testing import CliRunner
 
-
-
 import litellm.proxy.client.cli
 from litellm._version import version as litellm_version
 from litellm.proxy.client.cli import cli
diff --git a/tests/test_litellm/proxy/client/cli/test_pi.py b/tests/test_litellm/proxy/client/cli/test_pi.py
index 68c0ac70064..03e5d7dd197 100644
--- a/tests/test_litellm/proxy/client/cli/test_pi.py
+++ b/tests/test_litellm/proxy/client/cli/test_pi.py
@@ -4,13 +4,16 @@ import stat
 from concurrent.futures import ThreadPoolExecutor
 from pathlib import Path
 
+import pytest
 import requests
 
 from litellm.proxy.client.cli.commands.pi import (
+    ListingFailure,
     ModelLimits,
     PiSyncError,
     fetch_model_ids,
     fetch_model_limits,
+    fetch_model_listing,
     models_json_path,
     provider_block,
     sync_models_json,
@@ -28,6 +31,10 @@ class _FakeResponse:
         return self._payload
 
 
+def _refused(*args, **kwargs):
+    raise requests.ConnectionError("refused")
+
+
 class TestFetchModelIds:
     def test_returns_ids_in_proxy_order_deduped(self):
         captured = {}
@@ -44,6 +51,43 @@ class TestFetchModelIds:
         assert captured["url"] == "http://localhost:4000/v1/models"
         assert captured["headers"] == {"Authorization": "Bearer sk-key"}
 
+    def test_returns_rows_with_optional_source_model_and_dedups_identical_rows(self):
+        result = fetch_model_listing(
+            "http://localhost:4000",
+            "sk-key",
+            get=lambda *a, **k: _FakeResponse(
+                200,
+                {"data": [{"id": "emitted", "source_model": "source"}, {"id": "emitted", "source_model": "source"}]},
+            ),
+        )
+        assert not isinstance(result, PiSyncError)
+        assert tuple((model.id, model.source_model) for model in result) == (("emitted", "source"),)
+
+    @pytest.mark.parametrize(
+        "entry",
+        [
+            {"id": ""},
+            {"id": "emitted", "source_model": ""},
+            {"id": "emitted", "source_model": 1},
+        ],
+    )
+    def test_rejects_invalid_model_identity(self, entry):
+        result = fetch_model_listing(
+            "http://localhost:4000", "sk-key", get=lambda *a, **k: _FakeResponse(200, {"data": [entry]})
+        )
+        assert isinstance(result, PiSyncError) and result.kind is ListingFailure.BAD_BODY
+
+    def test_rejects_conflicting_emitted_id_mappings(self):
+        result = fetch_model_listing(
+            "http://localhost:4000",
+            "sk-key",
+            get=lambda *a, **k: _FakeResponse(
+                200,
+                {"data": [{"id": "emitted", "source_model": "one"}, {"id": "emitted", "source_model": "two"}]},
+            ),
+        )
+        assert isinstance(result, PiSyncError) and result.kind is ListingFailure.BAD_BODY
+
     def test_network_error_is_a_value(self):
         def boom(*a, **k):
             raise requests.ConnectionError("refused")
@@ -53,9 +97,7 @@ class TestFetchModelIds:
         assert "Could not list models" in result.message
 
     def test_non_200_is_a_value(self):
-        result = fetch_model_ids(
-            "http://localhost:4000", "sk-key", get=lambda *a, **k: _FakeResponse(500)
-        )
+        result = fetch_model_ids("http://localhost:4000", "sk-key", get=lambda *a, **k: _FakeResponse(500))
         assert isinstance(result, PiSyncError)
         assert "HTTP 500" in result.message
 
@@ -75,6 +117,22 @@ class TestFetchModelIds:
         )
         assert isinstance(result, PiSyncError)
         assert "no models" in result.message
+        assert result.kind is ListingFailure.EMPTY
+
+    @pytest.mark.parametrize(
+        ("get", "kind"),
+        [
+            (_refused, ListingFailure.UNREACHABLE),
+            (lambda *a, **k: _FakeResponse(401), ListingFailure.REJECTED),
+            (lambda *a, **k: _FakeResponse(403), ListingFailure.REJECTED),
+            (lambda *a, **k: _FakeResponse(500), ListingFailure.OTHER),
+            (lambda *a, **k: _FakeResponse(200), ListingFailure.BAD_BODY),
+        ],
+        ids=["unreachable", "401", "403", "500", "bad-body"],
+    )
+    def test_the_failure_kind_is_decided_where_the_response_is_classified(self, get, kind):
+        result = fetch_model_ids("http://localhost:4000", "sk-key", get=get)
+        assert isinstance(result, PiSyncError) and result.kind is kind
 
 
 class TestFetchModelLimits:
diff --git a/tests/test_litellm/proxy/client/cli/test_up_commands.py b/tests/test_litellm/proxy/client/cli/test_up_commands.py
index aead1764b0e..111d2f3d682 100644
--- a/tests/test_litellm/proxy/client/cli/test_up_commands.py
+++ b/tests/test_litellm/proxy/client/cli/test_up_commands.py
@@ -11,11 +11,11 @@ from click.testing import CliRunner
 
 from litellm.proxy.client.cli.commands import up as up_module
 from litellm.proxy.client.cli.commands.agents import AgentRunError
-from litellm.proxy.client.cli.commands.claude_settings import ClaudeSettingsError
+from litellm.proxy.client.cli.commands.claude_settings import ApiKeyHelper, ClaudeSettingsError
 from litellm.proxy.client.cli.commands.up import (
     BackupRecord,
     UpError,
-    _ensure_fresh_login,
+    ensure_fresh_login,
     down,
     load_json_or_empty,
     merge_claude_settings,
@@ -40,12 +40,12 @@ def _patch_paths(monkeypatch, tmp_path):
 
 class TestMergeClaudeSettings:
     def test_preserves_unrelated_top_level_keys(self):
-        merged = merge_claude_settings({"theme": "dark"}, "http://localhost:4000", "helper")
+        merged = merge_claude_settings({"theme": "dark"}, "http://localhost:4000", ApiKeyHelper("helper"))
         assert merged["theme"] == "dark"
 
     def test_preserves_unrelated_env_keys(self):
         settings = {"env": {"SOME_OTHER_VAR": "value"}}
-        merged = merge_claude_settings(settings, "http://localhost:4000", "helper")
+        merged = merge_claude_settings(settings, "http://localhost:4000", ApiKeyHelper("helper"))
         assert merged["env"]["SOME_OTHER_VAR"] == "value"
 
     def test_overrides_base_url_and_helper(self):
@@ -53,7 +53,7 @@ class TestMergeClaudeSettings:
             "env": {"ANTHROPIC_BASE_URL": "https://old.example.com"},
             "apiKeyHelper": "old-helper",
         }
-        merged = merge_claude_settings(settings, "http://localhost:4000/", "new-helper")
+        merged = merge_claude_settings(settings, "http://localhost:4000/", ApiKeyHelper("new-helper"))
         assert merged["env"]["ANTHROPIC_BASE_URL"] == "http://localhost:4000"
         assert merged["env"]["ENABLE_TOOL_SEARCH"] == "true"
         assert merged["env"]["CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"] == "1"
@@ -61,21 +61,21 @@ class TestMergeClaudeSettings:
 
     def test_preserves_existing_gateway_model_discovery(self):
         settings = {"env": {"CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY": "0"}}
-        merged = merge_claude_settings(settings, "http://localhost:4000", "helper")
+        merged = merge_claude_settings(settings, "http://localhost:4000", ApiKeyHelper("helper"))
         assert merged["env"]["CLAUDE_CODE_ENABLE_GATEWAY_MODEL_DISCOVERY"] == "0"
 
     def test_preserves_existing_tool_search(self):
         settings = {"env": {"ENABLE_TOOL_SEARCH": "false"}}
-        merged = merge_claude_settings(settings, "http://localhost:4000", "helper")
+        merged = merge_claude_settings(settings, "http://localhost:4000", ApiKeyHelper("helper"))
         assert merged["env"]["ENABLE_TOOL_SEARCH"] == "false"
 
     def test_drops_stray_api_key(self):
         settings = {"env": {"ANTHROPIC_API_KEY": "leaked-key"}}
-        merged = merge_claude_settings(settings, "http://localhost:4000", "helper")
+        merged = merge_claude_settings(settings, "http://localhost:4000", ApiKeyHelper("helper"))
         assert "ANTHROPIC_API_KEY" not in merged["env"]
 
     def test_works_from_empty_settings(self):
-        merged = merge_claude_settings({}, "http://localhost:4000", "helper")
+        merged = merge_claude_settings({}, "http://localhost:4000", ApiKeyHelper("helper"))
         assert merged["env"] == {
             "ANTHROPIC_BASE_URL": "http://localhost:4000",
             "ENABLE_TOOL_SEARCH": "true",
@@ -85,7 +85,7 @@ class TestMergeClaudeSettings:
 
     def test_does_not_mutate_input(self):
         settings = {"env": {"FOO": "bar"}}
-        merge_claude_settings(settings, "http://localhost:4000", "helper")
+        merge_claude_settings(settings, "http://localhost:4000", ApiKeyHelper("helper"))
         assert settings == {"env": {"FOO": "bar"}}
 
 
@@ -327,7 +327,7 @@ class TestEnsureFreshLogin:
         monkeypatch.setattr(up_module, "is_cli_token_fresh", lambda token_data: True)
         login_calls = _capture_login(monkeypatch)
 
-        _ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
+        ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
 
         assert login_calls == []
 
@@ -339,7 +339,7 @@ class TestEnsureFreshLogin:
             monkeypatch, on_login=lambda: store.log_in({"key": "sk-b", "base_url": "http://proxy-b:4000"}, "sk-b")
         )
 
-        _ensure_fresh_login(_make_ctx("http://proxy-b:4000"))
+        ensure_fresh_login(_make_ctx("http://proxy-b:4000"))
 
         assert login_calls == [("http://proxy-b:4000", False)]
         assert store.key_requests == ["http://proxy-b:4000", "http://proxy-b:4000"]
@@ -353,7 +353,7 @@ class TestEnsureFreshLogin:
             on_login=lambda: store.log_in({"key": "sk-a", "base_url": "http://proxy-a:4000"}, "sk-a"),
         )
 
-        _ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
+        ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
 
         assert login_calls == [("http://proxy-a:4000", False)]
 
@@ -363,7 +363,7 @@ class TestEnsureFreshLogin:
         monkeypatch.setattr(up_module, "is_cli_token_fresh", lambda token_data: True)
 
         with pytest.raises(UpError, match="Run `lite login` first"):
-            _ensure_fresh_login(_make_ctx("http://proxy-b:4000"))
+            ensure_fresh_login(_make_ctx("http://proxy-b:4000"))
 
     def test_trusts_a_pkce_credential_that_was_renewed_on_the_way_in(self, monkeypatch):
         """A --pkce key inside its freshness buffer is renewed by `get_stored_api_key`, so `lite up`
@@ -377,7 +377,7 @@ class TestEnsureFreshLogin:
         )
         login_calls = _capture_login(monkeypatch)
 
-        _ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
+        ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
 
         assert login_calls == []
         assert store.key_requests == ["http://proxy-a:4000"]
@@ -390,7 +390,7 @@ class TestEnsureFreshLogin:
             on_login=lambda: store.log_in(_pkce_record("http://proxy-a:4000", seconds_left=86_400), "sk-pkce-fresh"),
         )
 
-        _ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
+        ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
 
         assert login_calls == [("http://proxy-a:4000", True)]
 
@@ -399,7 +399,7 @@ class TestEnsureFreshLogin:
         _FakeTokenStore(monkeypatch, _pkce_record("http://proxy-a:4000", seconds_left=-10), {})
 
         with pytest.raises(UpError, match="Run `lite login --pkce` first"):
-            _ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
+            ensure_fresh_login(_make_ctx("http://proxy-a:4000"))
 
     def test_trusts_the_key_the_cli_group_already_resolved_instead_of_reading_the_token_file_again(
         self, monkeypatch
@@ -409,7 +409,7 @@ class TestEnsureFreshLogin:
         store = _FakeTokenStore(monkeypatch, _pkce_record("http://proxy-a:4000", seconds_left=86_400), {})
         login_calls = _capture_login(monkeypatch)
 
-        _ensure_fresh_login(_make_group_ctx("http://proxy-a:4000", api_key="sk-pkce-renewed-by-the-group"))
+        ensure_fresh_login(_make_group_ctx("http://proxy-a:4000", api_key="sk-pkce-renewed-by-the-group"))
 
         assert login_calls == []
         assert store.key_requests == []
@@ -423,7 +423,7 @@ class TestEnsureFreshLogin:
         )
 
         with pytest.raises(UpError, match="Run `lite login --pkce` first"):
-            _ensure_fresh_login(_make_group_ctx("http://proxy-a:4000", api_key=None))
+            ensure_fresh_login(_make_group_ctx("http://proxy-a:4000", api_key=None))
 
         assert store.key_requests == []
 
@@ -435,7 +435,7 @@ class TestEnsureFreshLogin:
             on_login=lambda: store.log_in(_pkce_record("http://proxy-a:4000", seconds_left=86_400), "sk-pkce-fresh"),
         )
 
-        _ensure_fresh_login(_make_group_ctx("http://proxy-a:4000", api_key=None))
+        ensure_fresh_login(_make_group_ctx("http://proxy-a:4000", api_key=None))
 
         assert login_calls == [("http://proxy-a:4000", True)]
         assert store.key_requests == ["http://proxy-a:4000"]
@@ -620,10 +620,7 @@ class TestUpCanInvokeTheRealLoginCommand:
             ctx.obj = {"base_url": "http://127.0.0.1:9"}
             ctx.invoke(real_login, pkce=False)
 
-        with (
-            patch(f"{AUTH_MODULE}.CLAUDE_SETTINGS_PATH", settings_path),
-            patch(f"{AUTH_MODULE}._start_cli_sso_flow", side_effect=RuntimeError("stop")),
-        ):
-            CliRunner().invoke(driver, [], standalone_mode=False)
+        with patch(f"{AUTH_MODULE}._start_cli_sso_flow", side_effect=RuntimeError("stop")):
+            CliRunner().invoke(driver, [], standalone_mode=False, env={"CLAUDE_CONFIG_DIR": str(tmp_path)})
 
         assert not settings_path.exists()
diff --git a/tests/test_litellm/proxy/common_utils/test_callback_utils.py b/tests/test_litellm/proxy/common_utils/test_callback_utils.py
index 66f77db6da9..ecb2375d495 100644
--- a/tests/test_litellm/proxy/common_utils/test_callback_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_callback_utils.py
@@ -1,30 +1,33 @@
 import copy
+import json
 import sys
 from types import ModuleType, SimpleNamespace
+from typing import Final
+from unittest.mock import patch
 
 import pytest
 
-
+import litellm
+from litellm.caching.caching import DualCache
+from litellm.constants import MAX_GUARDRAIL_SCAN_METADATA_HEADER_LENGTH
+from litellm.integrations.custom_logger import CustomLogger
+from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.common_utils.callback_utils import (
+    _serialize_scan_metadata_header,
     add_guardrail_scan_id,
     add_policy_to_applied_policies_header,
     decrypt_callback_vars,
     encrypt_callback_vars,
     get_logging_caching_headers,
-    initialize_callbacks_on_proxy,
     get_remaining_tokens_and_requests_from_request_data,
+    initialize_callbacks_on_proxy,
     normalize_callback_names,
+    process_callback,
     sanitize_openai_provider_metadata,
     strip_callback_config,
 )
-import litellm
-from litellm.caching.caching import DualCache
-from litellm.integrations.custom_logger import CustomLogger
-from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.utils import ProxyLogging
-
-from unittest.mock import patch
-from litellm.proxy.common_utils.callback_utils import process_callback
+from litellm.types.guardrails import GuardrailEventHooks
 
 
 def test_get_remaining_tokens_and_requests_from_request_data():
@@ -189,20 +192,109 @@ def test_get_logging_caching_headers_merges_metadata_and_litellm_metadata():
     assert headers["x-litellm-policy-sources"] == "global-baseline=team_default"
 
 
+def _record(
+    request_data: dict[str, object],
+    scan_id: str | None,
+    guardrail_name: str = "airs",
+    provider: str = "panw_prisma_airs",
+    stage: GuardrailEventHooks = GuardrailEventHooks.pre_call,
+) -> None:
+    add_guardrail_scan_id(
+        request_data=request_data, scan_id=scan_id, guardrail_name=guardrail_name, provider=provider, stage=stage
+    )
+
+
 def test_add_guardrail_scan_id_dedupes_and_becomes_response_header():
     request_data = {"litellm_metadata": {}}
 
-    add_guardrail_scan_id(request_data=request_data, scan_id="scan-1")
-    add_guardrail_scan_id(request_data=request_data, scan_id="scan-1")
-    add_guardrail_scan_id(request_data=request_data, scan_id="scan-2")
-    add_guardrail_scan_id(request_data=request_data, scan_id=None)
+    _record(request_data, "scan-1")
+    _record(request_data, "scan-1")
+    _record(request_data, "scan-2")
+    _record(request_data, None)
 
     assert request_data["litellm_metadata"]["guardrail_scan_ids"] == ("scan-1", "scan-2")
     assert get_logging_caching_headers(request_data)["x-litellm-guardrail-scan-id"] == "scan-1,scan-2"
 
 
-def test_get_logging_caching_headers_omits_scan_id_header_without_scans():
-    assert "x-litellm-guardrail-scan-id" not in get_logging_caching_headers({"litellm_metadata": {}})
+def test_scan_metadata_header_maps_each_id_to_its_guardrail_stage_and_provider():
+    request_data: Final[dict[str, object]] = {"litellm_metadata": {}}
+
+    _record(
+        request_data, "scan-1", guardrail_name="airs", provider="panw_prisma_airs", stage=GuardrailEventHooks.pre_call
+    )
+    _record(
+        request_data, "mod-1", guardrail_name="mod", provider="openai_moderation", stage=GuardrailEventHooks.pre_call
+    )
+    _record(
+        request_data, "scan-2", guardrail_name="airs", provider="panw_prisma_airs", stage=GuardrailEventHooks.post_call
+    )
+    _record(
+        request_data, "scan-2", guardrail_name="airs", provider="panw_prisma_airs", stage=GuardrailEventHooks.post_call
+    )
+    _record(request_data, None, guardrail_name="mod", provider="openai_moderation", stage=GuardrailEventHooks.post_call)
+
+    headers: Final = get_logging_caching_headers(request_data)
+    assert headers is not None
+    assert headers["x-litellm-guardrail-scan-id"] == "scan-1,mod-1,scan-2"
+    assert json.loads(headers["x-litellm-guardrail-scan-metadata"]) == [
+        {"guardrail": "airs", "stage": "pre_call", "provider": "panw_prisma_airs", "scan_id": "scan-1"},
+        {"guardrail": "mod", "stage": "pre_call", "provider": "openai_moderation", "scan_id": "mod-1"},
+        {"guardrail": "airs", "stage": "post_call", "provider": "panw_prisma_airs", "scan_id": "scan-2"},
+    ]
+
+
+def test_scan_metadata_keeps_same_id_reused_across_stages():
+    request_data: Final[dict[str, object]] = {"metadata": {}}
+
+    _record(request_data, "scan-1", stage=GuardrailEventHooks.pre_call)
+    _record(request_data, "scan-1", stage=GuardrailEventHooks.post_call)
+
+    headers: Final = get_logging_caching_headers(request_data)
+    assert headers is not None
+    assert headers["x-litellm-guardrail-scan-id"] == "scan-1"
+    assert [entry["stage"] for entry in json.loads(headers["x-litellm-guardrail-scan-metadata"])] == [
+        "pre_call",
+        "post_call",
+    ]
+
+
+def test_scan_metadata_header_drops_trailing_entries_to_stay_within_length_limit():
+    request_data: Final[dict[str, object]] = {"litellm_metadata": {}}
+    scan_ids: Final = tuple(f"0f9c4b7e-3d2a-4c1b-9e8f-{index:012d}" for index in range(40))
+    for scan_id in scan_ids:
+        _record(request_data, scan_id, stage=GuardrailEventHooks.post_call)
+
+    headers: Final = get_logging_caching_headers(request_data)
+    assert headers is not None
+    assert headers["x-litellm-guardrail-scan-id"] == ",".join(scan_ids)
+    header: Final = headers["x-litellm-guardrail-scan-metadata"]
+    assert len(header) <= MAX_GUARDRAIL_SCAN_METADATA_HEADER_LENGTH
+    kept: Final = json.loads(header)
+    assert 1 < len(kept) < len(scan_ids)
+    assert [entry["scan_id"] for entry in kept] == list(scan_ids[: len(kept)])
+
+
+def test_serialize_scan_metadata_header_keeps_exactly_the_entries_that_fit():
+    entries: Final = ({"scan_id": "a"}, {"scan_id": "b"}, {"scan_id": "c"})
+    two_entries: Final = '[{"scan_id":"a"},{"scan_id":"b"}]'
+
+    assert _serialize_scan_metadata_header(entries, max_length=len(two_entries)) == two_entries
+    assert _serialize_scan_metadata_header(entries, max_length=len(two_entries) - 1) == '[{"scan_id":"a"}]'
+    assert _serialize_scan_metadata_header(entries, max_length=len(two_entries) + 1) == two_entries
+    assert _serialize_scan_metadata_header(entries, max_length=1000) == json.dumps(entries, separators=(",", ":"))
+    assert _serialize_scan_metadata_header(entries, max_length=5) is None
+    assert _serialize_scan_metadata_header((), max_length=1000) is None
+
+
+def test_scan_metadata_is_an_internal_metadata_key():
+    assert sanitize_openai_provider_metadata({"guardrail_scan_metadata": "x", "keep": "y"}) == {"keep": "y"}
+
+
+def test_get_logging_caching_headers_omits_scan_headers_without_scans():
+    headers: Final = get_logging_caching_headers({"litellm_metadata": {}})
+    assert headers is not None
+    assert "x-litellm-guardrail-scan-id" not in headers
+    assert "x-litellm-guardrail-scan-metadata" not in headers
 
 
 def test_initialize_callbacks_on_proxy_instantiates_compression_interception(
diff --git a/tests/test_litellm/proxy/common_utils/test_http_parsing_utils.py b/tests/test_litellm/proxy/common_utils/test_http_parsing_utils.py
index 011571a37e0..bc4e756eb65 100644
--- a/tests/test_litellm/proxy/common_utils/test_http_parsing_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_http_parsing_utils.py
@@ -26,9 +26,58 @@ from litellm.proxy.common_utils.http_parsing_utils import (
     get_tags_from_request_body,
     numeric_form_fields,
     populate_request_with_path_params,
+    read_raw_json_body,
 )
 
 
+def _starlette_request(body: bytes, content_type: str) -> Request:
+    scope = {
+        "type": "http",
+        "method": "POST",
+        "path": "/v1/messages",
+        "headers": [(b"content-type", content_type.encode())],
+        "query_string": b"",
+    }
+    chunks = iter((body,))
+
+    async def receive():
+        return {"type": "http.request", "body": next(chunks, b""), "more_body": False}
+
+    return Request(scope, receive)
+
+
+@pytest.mark.asyncio
+async def test_read_raw_json_body_returns_the_bytes_the_parsed_body_came_from():
+    body = b'{"model": "claude-sonnet-4-5", "messages": [{"role": "user", "content": "hi"}]}'
+    request = _starlette_request(body, "application/json")
+
+    assert await _read_request_body(request) == orjson.loads(body)
+    assert await read_raw_json_body(request) == body
+
+
+@pytest.mark.asyncio
+async def test_read_raw_json_body_is_none_until_the_body_has_been_parsed():
+    request = _starlette_request(b'{"model": "claude-sonnet-4-5"}', "application/json")
+
+    assert await read_raw_json_body(request) is None
+    assert await read_raw_json_body(None) is None
+
+
+@pytest.mark.asyncio
+async def test_read_raw_json_body_is_none_for_form_bodies():
+    request = _starlette_request(b"model=claude-sonnet-4-5", "application/x-www-form-urlencoded")
+
+    assert await _read_request_body(request) == {"model": "claude-sonnet-4-5"}
+    assert await read_raw_json_body(request) is None
+
+
+@pytest.mark.asyncio
+async def test_read_raw_json_body_is_none_for_a_request_that_only_mocks_the_parsed_body_path():
+    mock_request = MagicMock()
+
+    assert await read_raw_json_body(mock_request) is None
+
+
 @pytest.mark.asyncio
 async def test_request_body_caching():
     """
diff --git a/tests/test_litellm/proxy/common_utils/test_model_listing_utils.py b/tests/test_litellm/proxy/common_utils/test_model_listing_utils.py
new file mode 100644
index 00000000000..7ef03140093
--- /dev/null
+++ b/tests/test_litellm/proxy/common_utils/test_model_listing_utils.py
@@ -0,0 +1,109 @@
+"""Model identity survives Claude Code presentation, filtering and configured alias precedence."""
+
+from itertools import combinations
+
+import pytest
+
+from litellm import Router
+from litellm.proxy.common_utils.model_listing_utils import (
+    ClaudeCodeRoutingNames,
+    claude_code_group_name,
+    claude_code_model_id,
+    claude_code_requested_group,
+    claude_code_view_ids,
+)
+
+
+def _encoded(name):
+    return "claude-router-" + name.encode().hex()
+
+
+def _marked(name):
+    return f"{_encoded(name)}[1m]"
+
+
+def _row(name, limit=1000000):
+    return {"id": name, "object": "model", "created": 0, "owned_by": "openai", "max_input_tokens": limit}
+
+
+def _router(*names, aliases=None):
+    return Router(
+        model_list=[
+            {"model_name": name, "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-fake"}}
+            for name in names
+        ],
+        model_group_alias=aliases,
+    )
+
+
+@pytest.mark.parametrize("limit", [None, 999999, 1000000])
+@pytest.mark.parametrize("name", ["foo", "foo[1m]", "foo[1M]", "a/b: 世界", "claude-router-foo", "claude-opus-5", "claude-opus-5[1m]"])
+def test_listing_round_trips_entire_source_name(name, limit):
+    names = frozenset({name})
+    view = claude_code_model_id(name, limit, names)
+    assert (claude_code_group_name(view, names) or view) == name
+    if "claude" not in name:
+        assert view.startswith(_encoded(name))
+    assert ("[1m]" in view.lower()) == (limit == 1000000 or "[1m]" in name.lower() and "claude" in name)
+
+
+def test_collision_matrix_round_trips_without_duplicate_ids():
+    universe = ("foo", "foo[1m]", "claude-router-foo", _encoded("foo"), _encoded("foo") + "[1m]", "claude-opus-5", "claude-opus-5[1m]")
+    for pair in combinations(universe, 2):
+        for visible in (pair, pair[:1], pair[1:]):
+            names = frozenset(pair)
+            view = claude_code_view_ids(tuple(_row(n) for n in visible), {"user-agent": "claude-code/2.1.267"}, names)
+            assert len(set(view.values())) == len(visible)
+            assert all((claude_code_group_name(shown, names) or shown) == source for source, shown in view.items())
+
+
+@pytest.mark.parametrize("spelling", ["claude-router-foo", "claude-router-ff", "claude-router-66 6f6f", "claude-router-666F6F", "claude-router-", _encoded("missing")])
+def test_unknown_or_noncanonical_ids_are_never_guessed(spelling):
+    assert claude_code_group_name(spelling, frozenset({"foo"})) is None
+
+
+@pytest.mark.parametrize("headers,enabled", [
+    ({"user-agent": "claude-code/2.1.267"}, True),
+    ({"user-agent": "claude-cli/2.1.267 (external, sdk-cli)"}, True),
+    ({"x-gateway-client": "Claude-Code"}, True),
+    ({"user-agent": "anthropic-sdk-python/0.40"}, False),
+    ({}, False),
+])
+def test_only_claude_code_gets_the_view(headers, enabled):
+    rows = (_row("foo"), _row("claude-opus-5"))
+    view = claude_code_view_ids(rows, headers, frozenset(row["id"] for row in rows))
+    assert dict(view) == ({"foo": _encoded("foo") + "[1m]", "claude-opus-5": "claude-opus-5[1m]"} if enabled else {})
+
+
+@pytest.mark.parametrize("layer", ["literal", "global", "router", "key", "team", "wildcard"])
+def test_configured_names_outrank_generated_ids_even_when_hidden_from_listing(monkeypatch, layer):
+    import litellm
+
+    encoded = _encoded("foo")
+    alias = {encoded: "other"}
+    monkeypatch.setattr(litellm, "model_alias_map", alias if layer == "global" else {})
+    router = _router("foo", "other", *( (encoded,) if layer == "literal" else ("*",) if layer == "wildcard" else ()), aliases=alias if layer == "router" else None)
+    maps = (alias,) if layer in ("key", "team") else ()
+    names = ClaudeCodeRoutingNames(router, None, maps)
+    assert claude_code_requested_group(encoded, router, None, maps) is None
+    assert claude_code_view_ids((_row("foo", None),), {"x-gateway-client": "claude-code"}, names)["foo"] == "foo"
+
+
+@pytest.mark.parametrize("source", ["foo", "foo[1m]", "世界"])
+def test_mutation_breaking_the_hex_name_cannot_route_to_the_source(source):
+    router = _router(source)
+    encoded = _encoded(source)
+    malformed = encoded[:-1] + ("0" if encoded[-1] != "0" else "1")
+    assert claude_code_requested_group(malformed, router, None) is None
+    assert claude_code_requested_group(_marked(source), router, None) == source
+
+
+def test_team_public_name_uses_the_same_scope_at_list_and_request():
+    router = Router(model_list=[{
+        "model_name": "model_name_team-a_id",
+        "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-fake"},
+        "model_info": {"team_id": "team-a", "team_public_model_name": "shared"},
+    }])
+    shown = claude_code_view_ids((_row("shared"),), {"user-agent": "claude-code/2.1.267"}, ClaudeCodeRoutingNames(router, "team-a"))["shared"]
+    assert claude_code_requested_group(shown, router, "team-a") == "shared"
+    assert claude_code_requested_group(shown, router, "team-b") is None
diff --git a/tests/test_litellm/proxy/common_utils/test_reset_budget_job.py b/tests/test_litellm/proxy/common_utils/test_reset_budget_job.py
index 56c0efb41d2..560953f0b51 100644
--- a/tests/test_litellm/proxy/common_utils/test_reset_budget_job.py
+++ b/tests/test_litellm/proxy/common_utils/test_reset_budget_job.py
@@ -403,7 +403,7 @@ def test_reset_budget_for_enduser(reset_budget_job, mock_prisma_client):
         {
             "table": "enduser",
             "op": "update_many",
-            "where": {"user_id": {"in": ["test-enduser-1"]}},
+            "where": {"budget_id": {"in": ["test-budget-1"]}, "spend": {"gt": 0}},
             "data": {"spend": 0},
         }
     ]
@@ -504,7 +504,7 @@ def test_reset_budget_all(reset_budget_job, mock_prisma_client):
         {
             "table": "enduser",
             "op": "update_many",
-            "where": {"user_id": {"in": ["test-enduser-1"]}},
+            "where": {"budget_id": {"in": ["test-budget-1"]}, "spend": {"gt": 0}},
             "data": {"spend": 0},
         }
     ]
@@ -524,6 +524,7 @@ _LINKED_TABLE_CASES = [
     ("org", {"budget_id": {"in": ["7d-budget-tier"]}, "spend": {"gt": 0}}),
     ("tag", {"budget_id": {"in": ["7d-budget-tier"]}, "spend": {"gt": 0}}),
     ("model_access_group", {"budget_id": {"in": ["7d-budget-tier"]}, "spend": {"gt": 0}}),
+    ("enduser", {"budget_id": {"in": ["7d-budget-tier"]}, "spend": {"gt": 0}}),
 ]
 
 
@@ -553,6 +554,48 @@ def test_budget_table_reset_zeroes_spend_on_every_linked_table(
     assert writes[0]["data"] == {"spend": 0}
 
 
+_POSTGRES_MAX_BIND_VARIABLES: Final = 32767
+
+
+def _bind_count(where: Dict[str, Any]) -> int:
+    """Bind variables one prisma where-clause compiles to: each scalar is one
+    placeholder and an ``in`` list contributes one per element."""
+    return sum(len(value["in"]) if isinstance(value, dict) and "in" in value else 1 for value in where.values())
+
+
+@pytest.mark.parametrize("population", [3, 40_000], ids=["small", "over-pg-bind-ceiling"])
+def test_enduser_reset_bind_count_does_not_scale_with_population(reset_budget_job, mock_prisma_client, population):
+    """Regression for #40564.
+
+    Enumerating every dependent user id put one bind variable per customer into
+    a single prepared statement. Past PostgreSQL's ceiling the statement could
+    not be parsed at all, so the whole atomic cascade rolled back,
+    budget_reset_at never advanced, and the tier stayed due on every later tick
+    forever. Matching on the budget link keeps the statement the same size no
+    matter how many customers share a tier.
+    """
+    budget = _budget_row(budget_id="shared-tier", budget_duration="1d")
+    mock_prisma_client.data["budget"] = [budget]
+    mock_prisma_client.data["enduser"] = [
+        types.SimpleNamespace(
+            spend=1.0,
+            litellm_budget_table=budget,
+            user_id=f"cust-{index:08d}",
+            budget_id="shared-tier",
+        )
+        for index in range(population)
+    ]
+
+    asyncio.run(reset_budget_job.reset_budget_for_litellm_budget_table())
+
+    writes = _batch_writes(mock_prisma_client, "enduser")
+    assert [_bind_count(write["where"]) for write in writes] == [2], (
+        f"the cascade must not enumerate {population} user ids: past "
+        f"{_POSTGRES_MAX_BIND_VARIABLES} binds PostgreSQL refuses the statement, got {writes[:1]}"
+    )
+    assert _batch_writes(mock_prisma_client, "budget")[0]["data"]["budget_reset_at"] is not None
+
+
 def test_budget_table_reset_writes_nothing_when_no_budget_is_due(reset_budget_job, mock_prisma_client):
     """Nothing due means no transaction is opened at all."""
     asyncio.run(reset_budget_job.reset_budget_for_litellm_budget_table())
@@ -720,14 +763,22 @@ def test_reset_budget_resets_endusers_with_null_budget_id(reset_budget_job, mock
 
     asyncio.run(reset_budget_job.reset_budget_for_litellm_budget_table())
 
-    # Both end users are zeroed by the same committed statement.
-    enduser_writes = _batch_writes(mock_prisma_client, "enduser")
-    assert len(enduser_writes) == 1, f"Expected a single enduser write, got {enduser_writes}"
-    assert set(enduser_writes[0]["where"]["user_id"]["in"]) == {
-        "enduser-explicit",
-        "enduser-implicit",
-    }
-    assert enduser_writes[0]["data"] == {"spend": 0}
+    # Both end users are zeroed: the linked rows on the tier's budget_id, the
+    # implicit ones on the NULL branch that stands in for the default tier.
+    assert _batch_writes(mock_prisma_client, "enduser") == [
+        {
+            "table": "enduser",
+            "op": "update_many",
+            "where": {"budget_id": {"in": [default_budget_id]}, "spend": {"gt": 0}},
+            "data": {"spend": 0},
+        },
+        {
+            "table": "enduser",
+            "op": "update_many",
+            "where": {"budget_id": None, "spend": {"gt": 0}},
+            "data": {"spend": 0},
+        },
+    ]
 
     # Verify find_many was called to fetch NULL-budget-id end users
     find_many_calls = mock_prisma_client.db.litellm_endusertable.find_many_calls
@@ -3043,13 +3094,13 @@ def test_budget_cascade_carries_enduser_overage_when_rollover_enabled(
     assert {
         "table": "enduser",
         "op": "update_many",
-        "where": {"user_id": {"in": ["enduser-roll"]}, "spend": {"gt": 10.0}},
+        "where": {"budget_id": "budget-roll", "spend": {"gt": 10.0}},
         "data": {"spend": {"decrement": 10.0}},
     } in enduser_writes
     assert {
         "table": "enduser",
         "op": "update_many",
-        "where": {"user_id": {"in": ["enduser-roll"]}, "spend": {"lte": 10.0}},
+        "where": {"budget_id": "budget-roll", "spend": {"gt": 0, "lte": 10.0}},
         "data": {"spend": 0},
     } in enduser_writes
 
diff --git a/tests/test_litellm/proxy/db/db_transaction_queue/test_pod_lock_manager.py b/tests/test_litellm/proxy/db/db_transaction_queue/test_pod_lock_manager.py
index ecd5c5f50c0..4684c3213d6 100644
--- a/tests/test_litellm/proxy/db/db_transaction_queue/test_pod_lock_manager.py
+++ b/tests/test_litellm/proxy/db/db_transaction_queue/test_pod_lock_manager.py
@@ -1,4 +1,5 @@
 import json
+import logging
 from datetime import datetime, timedelta, timezone
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -6,6 +7,7 @@ import pytest
 from fastapi.testclient import TestClient
 
 
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 from litellm.constants import DEFAULT_CRON_JOB_LOCK_TTL_SECONDS
 from litellm.proxy.db.db_transaction_queue.pod_lock_manager import PodLockManager
 
@@ -215,6 +217,22 @@ async def test_redis_error_handling(pod_lock_manager, mock_redis):
     )
 
 
+@pytest.mark.asyncio
+async def test_lock_refused_by_the_open_circuit_breaker_is_not_logged_as_an_error(pod_lock_manager, mock_redis, caplog):
+    """Every cron job retries its lock on a timer, so an open breaker must not add an error line per cycle."""
+    refused = RedisCircuitBreakerOpenError("Redis circuit breaker is open - skipping async_set_cache")
+    mock_redis.async_set_cache.side_effect = refused
+    mock_redis.async_get_cache.return_value = pod_lock_manager.pod_id
+    mock_redis.async_delete_cache.side_effect = refused
+
+    with caplog.at_level(logging.ERROR):
+        acquired = await pod_lock_manager.acquire_lock(cronjob_id="test_job")
+        await pod_lock_manager.release_lock(cronjob_id="test_job")
+
+    assert acquired is False
+    assert caplog.records == []
+
+
 @pytest.mark.asyncio
 async def test_bytes_handling(pod_lock_manager, mock_redis):
     """
diff --git a/tests/test_litellm/proxy/db/test_db_url_settings.py b/tests/test_litellm/proxy/db/test_db_url_settings.py
index ba342342366..875dca4bee3 100644
--- a/tests/test_litellm/proxy/db/test_db_url_settings.py
+++ b/tests/test_litellm/proxy/db/test_db_url_settings.py
@@ -11,15 +11,30 @@ clobber a pre-existing ``DATABASE_URL_READ_REPLICA``. A pre-existing
 ``DATABASE_URL`` (password auth) is likewise left untouched.
 """
 
+import datetime
+import hashlib
 import os
+import socket
+import ssl
+import tempfile
+import threading
 import urllib.parse
+from collections.abc import Iterator
+from dataclasses import dataclass
+from pathlib import Path
+from typing import Final
 from unittest.mock import patch
 
 import pytest
+from cryptography import x509
+from cryptography.hazmat.primitives import hashes, serialization
+from cryptography.hazmat.primitives.asymmetric import ec
 from pydantic import ValidationError
 
 from litellm.proxy.db.db_url_settings import (
+    PG_SSL_REQUEST,
     DatabaseURLSettings,
+    translate_libpq_ssl_params,
     unsupported_db_scheme,
     unsupported_db_scheme_message,
 )
@@ -381,9 +396,7 @@ def test_writer_password_is_percent_encoded(monkeypatch):
 def test_writer_url_not_clobbered_when_already_set(monkeypatch):
     """An operator-pinned DATABASE_URL (e.g. helm's $(VAR) assembly) always
     wins over the discrete fields."""
-    monkeypatch.setenv(
-        "DATABASE_URL", "postgresql://pinned:url@db.example.com:5432/litellm_db"
-    )
+    monkeypatch.setenv("DATABASE_URL", "postgresql://pinned:url@db.example.com:5432/litellm_db")
     monkeypatch.setenv("DATABASE_HOST", "writer.example.com")
     monkeypatch.setenv("DATABASE_USER", "litellm")
     monkeypatch.setenv("DATABASE_NAME", "litellm_db")
@@ -515,9 +528,7 @@ def test_apply_to_env_rejects_pinned_sqlite_direct_url(monkeypatch):
 
 def test_apply_to_env_rejects_pinned_non_postgres_reader(monkeypatch):
     monkeypatch.setenv("DATABASE_URL", "postgresql://u:p@writer.example.com:5432/db")
-    monkeypatch.setenv(
-        "DATABASE_URL_READ_REPLICA", "mysql://u:p@reader.example.com:3306/db"
-    )
+    monkeypatch.setenv("DATABASE_URL_READ_REPLICA", "mysql://u:p@reader.example.com:3306/db")
 
     with pytest.raises(RuntimeError, match=r"DATABASE_URL_READ_REPLICA.*mysql"):
         _apply()
@@ -542,15 +553,11 @@ def test_reader_inherits_writer_connection_params(monkeypatch):
         "DATABASE_URL",
         "postgresql://u:p@writer.example.com:5432/db?connection_limit=3&pool_timeout=20&pgbouncer=true",
     )
-    monkeypatch.setenv(
-        "DATABASE_URL_READ_REPLICA", "postgresql://u:p@reader.example.com:5432/db"
-    )
+    monkeypatch.setenv("DATABASE_URL_READ_REPLICA", "postgresql://u:p@reader.example.com:5432/db")
 
     _apply()
 
-    query = urllib.parse.parse_qs(
-        urllib.parse.urlsplit(os.environ["DATABASE_URL_READ_REPLICA"]).query
-    )
+    query = urllib.parse.parse_qs(urllib.parse.urlsplit(os.environ["DATABASE_URL_READ_REPLICA"]).query)
     assert query["connection_limit"] == ["3"]
     assert query["pool_timeout"] == ["20"]
     assert query["pgbouncer"] == ["true"]
@@ -568,9 +575,7 @@ def test_reader_keeps_its_own_pinned_connection_params(monkeypatch):
 
     _apply()
 
-    query = urllib.parse.parse_qs(
-        urllib.parse.urlsplit(os.environ["DATABASE_URL_READ_REPLICA"]).query
-    )
+    query = urllib.parse.parse_qs(urllib.parse.urlsplit(os.environ["DATABASE_URL_READ_REPLICA"]).query)
     assert query["connection_limit"] == ["50"]
     assert query["pool_timeout"] == ["20"]
 
@@ -776,6 +781,170 @@ def test_libpq_verify_full_and_sslrootcert_become_prisma_strict_sslcert(monkeypa
     }
 
 
+def _issue_cert(
+    subject: str, issuer: x509.Certificate | None, issuer_key: ec.EllipticCurvePrivateKey | None, ca: bool
+) -> tuple[x509.Certificate, ec.EllipticCurvePrivateKey]:
+    key: Final = ec.generate_private_key(ec.SECP256R1())
+    name: Final = x509.Name((x509.NameAttribute(x509.NameOID.COMMON_NAME, subject),))
+    now: Final = datetime.datetime.now(datetime.timezone.utc)
+    builder: Final = (
+        x509.CertificateBuilder()
+        .subject_name(name)
+        .issuer_name(issuer.subject if issuer else name)
+        .public_key(key.public_key())
+        .serial_number(x509.random_serial_number())
+        .not_valid_before(now - datetime.timedelta(minutes=5))
+        .not_valid_after(now + datetime.timedelta(days=1))
+        .add_extension(x509.BasicConstraints(ca=ca, path_length=None), critical=True)
+        .add_extension(x509.SubjectAlternativeName((x509.DNSName("localhost"),)), critical=False)
+    )
+    return builder.sign(issuer_key or key, hashes.SHA256()), key
+
+
+def _pem(cert: x509.Certificate) -> bytes:
+    return cert.public_bytes(serialization.Encoding.PEM)
+
+
+class _TlsPostgresStub:
+    """Answers one libpq ``SSLRequest`` with ``S`` and serves ``leaf + intermediate``."""
+
+    def __init__(self, chain_pem: Path, key_pem: Path) -> None:
+        self.context: Final = ssl.SSLContext(ssl.PROTOCOL_TLS_SERVER)
+        self.context.load_cert_chain(str(chain_pem), str(key_pem))
+        self.listener: Final = socket.create_server(("127.0.0.1", 0))
+        self.port: Final[int] = self.listener.getsockname()[1]
+        self.thread: Final = threading.Thread(target=self._serve, daemon=True)
+        self.thread.start()
+
+    def _serve(self) -> None:
+        with self.listener:
+            while True:
+                try:
+                    conn: socket.socket = self.listener.accept()[0]
+                except OSError:
+                    return
+                with conn:
+                    try:
+                        if conn.recv(8) == PG_SSL_REQUEST:
+                            conn.sendall(b"S")
+                            with self.context.wrap_socket(conn, server_side=True) as tls:
+                                tls.recv(1)
+                    except OSError:
+                        continue
+
+
+@dataclass(frozen=True, slots=True)
+class _RdsLikePki:
+    bundle: Path
+    wrong_bundle: Path
+    root: Path
+    port: int
+
+
+@pytest.fixture
+def rds_like_pki(tmp_path: Path) -> Iterator[_RdsLikePki]:
+    """An RDS-shaped trust setup: the server sends leaf + intermediate, the
+    bundle holds only self-signed roots, and the right root is not first."""
+    root, root_key = _issue_cert("Real Root CA", None, None, ca=True)
+    decoys: Final = tuple(_issue_cert(f"Decoy Root CA {i}", None, None, ca=True)[0] for i in range(3))
+    intermediate, intermediate_key = _issue_cert("Intermediate CA", root, root_key, ca=True)
+    leaf, leaf_key = _issue_cert("localhost", intermediate, intermediate_key, ca=False)
+    chain_pem: Final = tmp_path / "server-chain.pem"
+    chain_pem.write_bytes(_pem(leaf) + _pem(intermediate))
+    key_pem: Final = tmp_path / "server.key"
+    key_pem.write_bytes(
+        leaf_key.private_bytes(
+            serialization.Encoding.PEM, serialization.PrivateFormat.PKCS8, serialization.NoEncryption()
+        )
+    )
+    bundle: Final = tmp_path / "global-bundle.pem"
+    bundle.write_bytes(b"".join(_pem(decoy) for decoy in decoys) + _pem(root))
+    wrong_bundle: Final = tmp_path / "wrong-bundle.pem"
+    wrong_bundle.write_bytes(b"".join(_pem(decoy) for decoy in decoys))
+    root_pem: Final = tmp_path / "root.pem"
+    root_pem.write_bytes(_pem(root))
+    stub: Final = _TlsPostgresStub(chain_pem, key_pem)
+    yield _RdsLikePki(bundle=bundle, wrong_bundle=wrong_bundle, root=root_pem, port=stub.port)
+    stub.listener.close()
+
+
+def _params(url: str) -> tuple[tuple[str, str], ...]:
+    return tuple(urllib.parse.parse_qsl(urllib.parse.urlsplit(url).query, keep_blank_values=True))
+
+
+def test_multi_root_bundle_is_pinned_to_the_root_the_server_chains_to(
+    monkeypatch: pytest.MonkeyPatch, rds_like_pki: _RdsLikePki
+):
+    """Prisma's ``sslcert`` loads only the first certificate of the file, so
+    handing it the whole RDS bundle trusts one region's root and fails with
+    "unable to get local issuer certificate" everywhere else. The URL Prisma
+    receives must point at a single-certificate file holding the server's root."""
+    monkeypatch.setenv(
+        "DATABASE_URL",
+        f"postgresql://u:p@localhost:{rds_like_pki.port}/litellm_db?sslmode=verify-full&sslrootcert={rds_like_pki.bundle}",
+    )
+
+    _apply()
+
+    (sslmode, sslcert, sslaccept, _) = _params(os.environ["DATABASE_URL"])
+    assert (sslmode, sslaccept) == (("sslmode", "require"), ("sslaccept", "strict"))
+    assert sslcert[0] == "sslcert" and sslcert[1] != str(rds_like_pki.bundle)
+    assert Path(sslcert[1]).read_bytes() == rds_like_pki.root.read_bytes()
+
+
+def test_pinned_root_replaces_a_planted_symlink_instead_of_writing_through_it(
+    monkeypatch: pytest.MonkeyPatch, rds_like_pki: _RdsLikePki, tmp_path: Path
+):
+    """The pinned file has a predictable name in a shared temp dir, so a symlink
+    planted there must not redirect the write onto its target."""
+    monkeypatch.setattr(tempfile, "tempdir", str(tmp_path))
+    root_der: Final = x509.load_pem_x509_certificate(rds_like_pki.root.read_bytes()).public_bytes(
+        serialization.Encoding.DER
+    )
+    pinned: Final = tmp_path / f"litellm-sslcert-{hashlib.sha256(root_der).hexdigest()[:16]}.pem"
+    victim: Final = tmp_path / "victim.txt"
+    victim.write_text("untouched")
+    pinned.symlink_to(victim)
+    monkeypatch.setenv(
+        "DATABASE_URL",
+        f"postgresql://u:p@localhost:{rds_like_pki.port}/litellm_db?sslmode=verify-full&sslrootcert={rds_like_pki.bundle}",
+    )
+
+    _apply()
+
+    assert ("sslcert", str(pinned)) in _params(os.environ["DATABASE_URL"])
+    assert victim.read_text() == "untouched"
+    assert not pinned.is_symlink() and pinned.read_bytes() == rds_like_pki.root.read_bytes()
+
+
+def test_bundle_without_the_servers_root_is_passed_through_unchanged(
+    monkeypatch: pytest.MonkeyPatch, rds_like_pki: _RdsLikePki
+):
+    """Nothing in the bundle verifies the server, so no root is pinned and
+    Prisma keeps rejecting the connection instead of trusting a root the
+    operator never shipped."""
+    monkeypatch.setenv(
+        "DATABASE_URL",
+        f"postgresql://u:p@localhost:{rds_like_pki.port}/litellm_db"
+        f"?sslmode=verify-full&sslrootcert={rds_like_pki.wrong_bundle}",
+    )
+
+    _apply()
+
+    assert ("sslcert", str(rds_like_pki.wrong_bundle)) in _params(os.environ["DATABASE_URL"])
+
+
+def test_root_cert_resolver_receives_the_urls_host_and_default_port():
+    def resolver(cert_path: str, host: str, port: int) -> str:
+        return f"/pinned/{host}/{port}{cert_path}"
+
+    url: Final = translate_libpq_ssl_params(
+        "postgresql://u:p@db.example.com/litellm_db?sslmode=verify-full&sslrootcert=/certs/bundle.pem", resolver
+    )
+
+    assert ("sslcert", "/pinned/db.example.com/5432/certs/bundle.pem") in _params(url)
+
+
 def test_libpq_verify_ca_becomes_prisma_strict(monkeypatch):
     monkeypatch.setenv("DATABASE_URL", "postgresql://u:p@db.example.com:5432/litellm_db?sslmode=verify-ca")
 
diff --git a/tests/test_litellm/proxy/db/test_exception_handler.py b/tests/test_litellm/proxy/db/test_exception_handler.py
index c685d778c0e..3f009137a1c 100644
--- a/tests/test_litellm/proxy/db/test_exception_handler.py
+++ b/tests/test_litellm/proxy/db/test_exception_handler.py
@@ -665,10 +665,47 @@ def test_is_deadlock_error_excludes_non_deadlocks(error):
     assert PrismaDBExceptionHandler.is_deadlock_error(error) is False
 
 
+READ_ONLY_CONNECTOR_ERROR: Final = (
+    "Error occurred during query execution:\nConnectorError(ConnectorError { user_facing_error: None, "
+    'kind: QueryError(PostgresError { code: "25006", message: "cannot execute UPDATE in a read-only transaction", '
+    'severity: "ERROR", detail: None, column: None, hint: None }), transient: false })'
+)
+
+
+@pytest.mark.parametrize(
+    "error",
+    [
+        DataError(data={"user_facing_error": {"message": READ_ONLY_CONNECTOR_ERROR}}),
+        RawQueryError(data={"user_facing_error": {"message": "cannot execute INSERT in a read-only transaction"}}),
+        PrismaError(
+            'PostgresError { code: "25006", message: "kann DELETE in einer Read-Only-Transaktion nicht ausführen" }'
+        ),
+    ],
+)
+def test_is_read_only_transaction_error_matches_sqlstate_25006(error):
+    assert PrismaDBExceptionHandler.is_read_only_transaction_error(error) is True
+
+
+@pytest.mark.parametrize(
+    "error",
+    [
+        UniqueViolationError(data={"user_facing_error": {"error_code": "P2002", "meta": {"table": "t"}}}),
+        PrismaError("can't reach database server"),
+        RawQueryError(data={"user_facing_error": {"message": "deadlock detected", "meta": {"table": "t"}}}),
+        httpx.ConnectError("connection refused"),
+        RuntimeError("cannot execute UPDATE in a read-only transaction"),
+        ValueError('"25006"'),
+    ],
+)
+def test_is_read_only_transaction_error_excludes_other_failures(error):
+    assert PrismaDBExceptionHandler.is_read_only_transaction_error(error) is False
+
+
 MOCKED_PRISMA_PREDICATES: Final = (
     PrismaDBExceptionHandler.is_database_infrastructure_error,
     PrismaDBExceptionHandler.is_database_transport_error,
     PrismaDBExceptionHandler.is_deadlock_error,
+    PrismaDBExceptionHandler.is_read_only_transaction_error,
     PrismaDBExceptionHandler.is_prisma_engine_internal_error,
     PrismaDBExceptionHandler.is_database_service_unavailable_error,
 )
diff --git a/tests/test_litellm/proxy/db/test_gateway_request_tracking.py b/tests/test_litellm/proxy/db/test_gateway_request_tracking.py
index 93a11a914cb..045261e2d53 100644
--- a/tests/test_litellm/proxy/db/test_gateway_request_tracking.py
+++ b/tests/test_litellm/proxy/db/test_gateway_request_tracking.py
@@ -8,8 +8,11 @@ from datetime import datetime, timezone
 
 import pytest
 
+from litellm.constants import MAX_REDIS_BUFFER_DEQUEUE_COUNT, REDIS_GATEWAY_REQUESTS_BUFFER_KEY
 from litellm.proxy.db.gateway_request_tracking import (
+    GATEWAY_REQUESTS_JOB_NAME,
     GatewayRequestAccumulator,
+    GatewayRequestRedisBuffer,
     commit_gateway_requests_to_db,
     flush_gateway_requests,
 )
@@ -83,40 +86,47 @@ def test_drain_snapshot_is_not_mutated_by_later_records():
 # ── commit ────────────────────────────────────────────────────────────────────
 
 
-class FakeTable:
-    def __init__(self) -> None:
-        self.upserts: list[dict] = []
-
-    def upsert(self, *, where: dict, data: dict) -> None:
-        self.upserts.append({"where": where, "data": data})
-
-
-class FakeBatcher:
-    def __init__(self, table: FakeTable) -> None:
-        self.litellm_dailygatewayrequests = table
-
-    async def __aenter__(self) -> "FakeBatcher":
-        return self
-
-    async def __aexit__(self, *args: object) -> bool:
-        return False
-
-
 class FakeDB:
-    def __init__(self, table: FakeTable) -> None:
-        self._table = table
+    def __init__(self) -> None:
+        self.statements: list[tuple[str, tuple[object, ...]]] = []
 
-    def batch_(self) -> FakeBatcher:
-        return FakeBatcher(self._table)
+    async def execute_raw(self, query: str, *args: object) -> int:
+        self.statements.append((query, args))
+        return len(args) // 5
 
 
 class FakePrismaClient:
     def __init__(self) -> None:
-        self.table = FakeTable()
-        self.db = FakeDB(self.table)
+        self.db = FakeDB()
 
 
-def test_commit_upserts_one_incrementing_row_per_key():
+def _rows_written(client: FakePrismaClient) -> list[tuple[object, ...]]:
+    """Every (date, category, route, successful, failed) tuple the database received, in statement order."""
+    return [params[i : i + 5] for _, params in client.db.statements for i in range(0, len(params), 5)]
+
+
+def test_commit_increments_with_a_single_statement_for_the_whole_snapshot():
+    """One statement per flush is the whole point: the previous per-key upsert cost
+    the primary (workers x routes) statements per interval."""
+    client = FakePrismaClient()
+    snapshot = {
+        GatewayRequestKey(date="2026-08-01", category="llm", route=route): (
+            GatewayRequestCounts(successful_requests=7, failed_requests=2)
+        )
+        for route in ("/chat/completions", "/embeddings", "/responses", "/v1/messages", "/mcp")
+    }
+
+    asyncio.run(commit_gateway_requests_to_db(prisma_client=client, snapshot=snapshot))
+
+    assert len(client.db.statements) == 1
+    sql, params = client.db.statements[0]
+    assert sql.count("ON CONFLICT") == 1
+    assert sql.count("(NOW() AT TIME ZONE 'UTC'))") == 5
+    assert len(params) == 25
+
+
+def test_commit_sql_adds_to_the_existing_row_instead_of_replacing_it():
+    """A worker only knows its own share; the SQL must add EXCLUDED onto the stored count."""
     client = FakePrismaClient()
     snapshot = {
         GatewayRequestKey(date="2026-08-01", category="llm", route="/chat/completions"): (
@@ -126,20 +136,36 @@ def test_commit_upserts_one_incrementing_row_per_key():
 
     asyncio.run(commit_gateway_requests_to_db(prisma_client=client, snapshot=snapshot))
 
-    assert len(client.table.upserts) == 1
-    written = client.table.upserts[0]
-    assert written["where"] == {
-        "date_category_route": {
-            "date": "2026-08-01",
-            "category": "llm",
-            "route": "/chat/completions",
-        }
+    sql, params = client.db.statements[0]
+    assert 'INSERT INTO "LiteLLM_DailyGatewayRequests"' in sql
+    assert 'ON CONFLICT ("date", "category", "route") DO UPDATE SET' in sql
+    assert (
+        '"successful_requests" = "LiteLLM_DailyGatewayRequests"."successful_requests" + EXCLUDED."successful_requests"'
+        in sql
+    )
+    assert '"failed_requests" = "LiteLLM_DailyGatewayRequests"."failed_requests" + EXCLUDED."failed_requests"' in sql
+    assert params == ("2026-08-01", "llm", "/chat/completions", 7, 2)
+
+
+def test_commit_placeholders_line_up_with_params():
+    """$n positions are generated per row; a drift here silently swaps a route for a count."""
+    client = FakePrismaClient()
+    snapshot = {
+        GatewayRequestKey(date="2026-08-01", category="llm", route="/chat/completions"): (
+            GatewayRequestCounts(successful_requests=1, failed_requests=0)
+        ),
+        GatewayRequestKey(date="2026-08-01", category="mcp", route="/mcp"): (
+            GatewayRequestCounts(successful_requests=0, failed_requests=3)
+        ),
     }
-    assert written["data"]["update"] == {
-        "successful_requests": {"increment": 7},
-        "failed_requests": {"increment": 2},
-    }
-    assert written["data"]["create"]["successful_requests"] == 7
+
+    asyncio.run(commit_gateway_requests_to_db(prisma_client=client, snapshot=snapshot))
+
+    sql, params = client.db.statements[0]
+    assert "($1::text, $2::text, $3::text, $4::bigint, $5::bigint," in sql
+    assert "($6::text, $7::text, $8::text, $9::bigint, $10::bigint," in sql
+    assert "$11" not in sql
+    assert params == ("2026-08-01", "llm", "/chat/completions", 1, 0, "2026-08-01", "mcp", "/mcp", 0, 3)
 
 
 def test_commit_is_deterministically_ordered():
@@ -154,17 +180,14 @@ def test_commit_is_deterministically_ordered():
 
     asyncio.run(commit_gateway_requests_to_db(prisma_client=client, snapshot=snapshot))
 
-    written_order = [
-        (row["where"]["date_category_route"]["date"], row["where"]["date_category_route"]["category"])
-        for row in client.table.upserts
-    ]
+    written_order = [(row[0], row[1]) for row in _rows_written(client)]
     assert written_order == [("2026-08-01", "llm"), ("2026-08-01", "mcp"), ("2026-08-02", "llm")]
 
 
 def test_commit_skips_the_database_entirely_when_nothing_accumulated():
     client = FakePrismaClient()
     asyncio.run(commit_gateway_requests_to_db(prisma_client=client, snapshot={}))
-    assert client.table.upserts == []
+    assert client.db.statements == []
 
 
 # ── flush ─────────────────────────────────────────────────────────────────────
@@ -177,12 +200,12 @@ def test_flush_drains_and_commits():
 
     asyncio.run(flush_gateway_requests(client, acc))
 
-    assert len(client.table.upserts) == 1
+    assert len(client.db.statements) == 1
     assert acc.drain() == {}
 
 
 class ExplodingDB:
-    def batch_(self):
+    async def execute_raw(self, query: str, *args: object) -> int:
         raise RuntimeError("db gone")
 
 
@@ -208,10 +231,7 @@ def test_failed_flush_keeps_counts_for_the_next_attempt():
     client = FakePrismaClient()
     asyncio.run(flush_gateway_requests(client, acc))
 
-    assert client.table.upserts[0]["data"]["update"] == {
-        "successful_requests": {"increment": 1},
-        "failed_requests": {"increment": 1},
-    }
+    assert _rows_written(client) == [(_today(), "llm", "/chat/completions", 1, 1)]
 
 
 def test_restored_counts_merge_with_requests_recorded_meanwhile():
@@ -223,5 +243,272 @@ def test_restored_counts_merge_with_requests_recorded_meanwhile():
     client = FakePrismaClient()
     asyncio.run(flush_gateway_requests(client, acc))
 
-    assert len(client.table.upserts) == 1
-    assert client.table.upserts[0]["data"]["update"]["successful_requests"] == {"increment": 2}
+    assert _rows_written(client) == [(_today(), "llm", "/chat/completions", 2, 0)]
+
+
+class ExplodingDBWithInFlightRequest:
+    """Fails the write after a request has been recorded while it was in flight."""
+
+    def __init__(self, accumulator: GatewayRequestAccumulator) -> None:
+        self.accumulator = accumulator
+
+    async def execute_raw(self, query: str, *args: object) -> int:
+        _record(self.accumulator, 500)
+        raise RuntimeError("db gone")
+
+
+class ExplodingClientWithInFlightRequest:
+    def __init__(self, accumulator: GatewayRequestAccumulator) -> None:
+        self.db = ExplodingDBWithInFlightRequest(accumulator)
+
+
+def test_restore_keeps_requests_recorded_while_the_failed_write_was_in_flight():
+    acc = GatewayRequestAccumulator()
+    _record(acc, 200)
+    asyncio.run(flush_gateway_requests(ExplodingClientWithInFlightRequest(acc), acc))
+
+    client = FakePrismaClient()
+    asyncio.run(flush_gateway_requests(client, acc))
+
+    assert _rows_written(client) == [(_today(), "llm", "/chat/completions", 1, 1)]
+
+
+# ── redis buffer ──────────────────────────────────────────────────────────────
+
+
+class FakeRedis:
+    def __init__(self) -> None:
+        self.lists: dict[str, list[str]] = {}
+
+    async def async_rpush(self, key: str, values: list[str]) -> int:
+        self.lists.setdefault(key, []).extend(values)
+        return len(self.lists[key])
+
+    async def async_lpop(self, key: str, count: int) -> list[str] | None:
+        queue = self.lists.get(key, [])
+        if not queue:
+            return None
+        popped, self.lists[key] = queue[:count], queue[count:]
+        return popped
+
+
+class FakePodLock:
+    def __init__(self, *, leader: bool) -> None:
+        self.leader = leader
+        self.held: list[str] = []
+        self.released: list[str] = []
+
+    async def acquire_lock(self, cronjob_id: str) -> bool:
+        self.held.append(cronjob_id)
+        return self.leader
+
+    async def release_lock(self, cronjob_id: str) -> None:
+        self.released.append(cronjob_id)
+
+
+class FakeLease:
+    """Redis-side view of the job lock: SET NX by pod id, re-entrant for the holder, freed only by release or TTL."""
+
+    def __init__(self) -> None:
+        self.holder: str | None = None
+
+
+class FakeLeasePodLock:
+    def __init__(self, lease: FakeLease, pod_id: str) -> None:
+        self.lease = lease
+        self.pod_id = pod_id
+
+    async def acquire_lock(self, cronjob_id: str) -> bool:
+        if self.lease.holder is None:
+            self.lease.holder = self.pod_id
+        return self.lease.holder == self.pod_id
+
+    async def release_lock(self, cronjob_id: str) -> None:
+        if self.lease.holder == self.pod_id:
+            self.lease.holder = None
+
+
+def _buffer(redis: FakeRedis, *, leader: bool) -> tuple[GatewayRequestRedisBuffer, FakePodLock]:
+    lock = FakePodLock(leader=leader)
+    return GatewayRequestRedisBuffer(redis_cache=redis, pod_lock_manager=lock), lock  # pyright: ignore[reportArgumentType]  # duck-typed fakes
+
+
+def test_non_leader_workers_push_to_redis_and_never_touch_the_database():
+    redis = FakeRedis()
+    client = FakePrismaClient()
+    for _ in range(3):
+        acc = GatewayRequestAccumulator()
+        _record(acc, 200)
+        buffer, _ = _buffer(redis, leader=False)
+        asyncio.run(flush_gateway_requests(client, acc, buffer))
+
+    assert client.db.statements == []
+    assert len(redis.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY]) == 3
+
+
+def test_leader_folds_every_workers_snapshot_into_one_statement():
+    """Fifty workers each flushing the same routes must cost the primary one statement, not fifty."""
+    redis = FakeRedis()
+    client = FakePrismaClient()
+    for _ in range(50):
+        acc = GatewayRequestAccumulator()
+        _record(acc, 200)
+        _record(acc, 500, route="/responses")
+        buffer, _ = _buffer(redis, leader=False)
+        asyncio.run(flush_gateway_requests(client, acc, buffer))
+
+    leader_acc = GatewayRequestAccumulator()
+    _record(leader_acc, 200)
+    leader, lock = _buffer(redis, leader=True)
+    asyncio.run(flush_gateway_requests(client, leader_acc, leader))
+
+    assert len(client.db.statements) == 1
+    assert _rows_written(client) == [
+        (_today(), "llm", "/chat/completions", 51, 0),
+        (_today(), "llm", "/responses", 0, 50),
+    ]
+    assert redis.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY] == []
+    assert lock.held == [GATEWAY_REQUESTS_JOB_NAME]
+    assert lock.released == []
+
+
+def test_leader_keeps_the_lease_so_staggered_pods_cost_one_statement_per_interval():
+    """Pods flush on their own clocks; without the lease each one would win the lock in turn and commit alone."""
+    redis = FakeRedis()
+    client = FakePrismaClient()
+    lease = FakeLease()
+    pods = tuple(
+        GatewayRequestRedisBuffer(redis_cache=redis, pod_lock_manager=FakeLeasePodLock(lease, f"pod-{i}"))  # pyright: ignore[reportArgumentType]  # duck-typed fakes
+        for i in range(4)
+    )
+
+    for _interval in range(3):
+        for pod in pods:
+            acc = GatewayRequestAccumulator()
+            _record(acc, 200)
+            asyncio.run(flush_gateway_requests(client, acc, pod))
+
+    assert lease.holder == "pod-0"
+    assert len(client.db.statements) == 3
+    assert [row[3] for row in _rows_written(client)] == [1, 4, 4]
+    assert len(redis.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY]) == 3
+
+
+def test_leader_drains_a_backlog_deeper_than_one_capped_pop():
+    """More workers than MAX_REDIS_BUFFER_DEQUEUE_COUNT must not leave a growing tail queued behind the cap."""
+    redis = FakeRedis()
+    client = FakePrismaClient()
+    workers = MAX_REDIS_BUFFER_DEQUEUE_COUNT * 2 + 1
+    for _ in range(workers):
+        acc = GatewayRequestAccumulator()
+        _record(acc, 200)
+        buffer, _ = _buffer(redis, leader=False)
+        asyncio.run(flush_gateway_requests(client, acc, buffer))
+
+    leader, _ = _buffer(redis, leader=True)
+    asyncio.run(flush_gateway_requests(client, GatewayRequestAccumulator(), leader))
+
+    assert len(client.db.statements) == 1
+    assert _rows_written(client) == [(_today(), "llm", "/chat/completions", workers, 0)]
+    assert redis.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY] == []
+
+
+def test_leader_with_nothing_buffered_writes_nothing():
+    redis = FakeRedis()
+    client = FakePrismaClient()
+    leader, lock = _buffer(redis, leader=True)
+
+    asyncio.run(flush_gateway_requests(client, GatewayRequestAccumulator(), leader))
+
+    assert client.db.statements == []
+    assert lock.released == []
+
+
+def test_leader_requeues_to_redis_when_the_database_commit_fails():
+    """Counts popped from Redis are gone from every worker; a failed commit must put them back."""
+    redis = FakeRedis()
+    acc = GatewayRequestAccumulator()
+    _record(acc, 200)
+    _record(acc, 200)
+    leader, lock = _buffer(redis, leader=True)
+
+    asyncio.run(flush_gateway_requests(ExplodingClient(), acc, leader))
+
+    assert len(redis.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY]) == 1
+    assert lock.released == []
+    assert acc.drain() == {}
+
+    client = FakePrismaClient()
+    retry, _ = _buffer(redis, leader=True)
+    asyncio.run(flush_gateway_requests(client, GatewayRequestAccumulator(), retry))
+    assert _rows_written(client) == [(_today(), "llm", "/chat/completions", 2, 0)]
+
+
+class ExplodingRedis(FakeRedis):
+    async def async_rpush(self, key: str, values: list[str]) -> int:
+        raise RuntimeError("redis gone")
+
+
+class UnreadableRedis(FakeRedis):
+    async def async_lpop(self, key: str, count: int) -> list[str] | None:
+        raise RuntimeError("redis gone mid-flush")
+
+
+class UnwritableRedis(FakeRedis):
+    """Pops succeed, pushes fail: a Redis that went read-only between the leader's pop and its re-queue."""
+
+    async def async_rpush(self, key: str, values: list[str]) -> int:
+        raise RuntimeError("redis read-only")
+
+
+def test_leader_keeps_popped_counts_in_memory_when_both_the_database_and_the_requeue_fail():
+    """The pop removed the only copy; if Redis will not take it back the leader itself must carry it."""
+    redis = FakeRedis()
+    worker_acc = GatewayRequestAccumulator()
+    _record(worker_acc, 200)
+    _record(worker_acc, 200)
+    worker, _ = _buffer(redis, leader=False)
+    asyncio.run(flush_gateway_requests(FakePrismaClient(), worker_acc, worker))
+
+    degraded = UnwritableRedis()
+    degraded.lists = redis.lists
+    leader_acc = GatewayRequestAccumulator()
+    leader, _ = _buffer(degraded, leader=True)
+    asyncio.run(flush_gateway_requests(ExplodingClient(), leader_acc, leader))
+    assert degraded.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY] == []
+
+    client = FakePrismaClient()
+    retry, _ = _buffer(redis, leader=True)
+    asyncio.run(flush_gateway_requests(client, leader_acc, retry))
+    assert _rows_written(client) == [(_today(), "llm", "/chat/completions", 2, 0)]
+
+
+def test_leader_whose_redis_read_fails_leaves_the_pushed_rows_for_the_next_flush():
+    """The scheduler job must not raise, and nothing is popped so nothing needs restoring anywhere."""
+    redis = UnreadableRedis()
+    acc = GatewayRequestAccumulator()
+    _record(acc, 200)
+    client = FakePrismaClient()
+    leader, _ = _buffer(redis, leader=True)
+
+    asyncio.run(flush_gateway_requests(client, acc, leader))
+
+    assert client.db.statements == []
+    assert acc.drain() == {}
+    assert len(redis.lists[REDIS_GATEWAY_REQUESTS_BUFFER_KEY]) == 1
+
+
+def test_failed_redis_push_keeps_counts_locally_for_the_next_flush():
+    acc = GatewayRequestAccumulator()
+    _record(acc, 200)
+    _record(acc, 500)
+    buffer, lock = _buffer(ExplodingRedis(), leader=True)
+
+    asyncio.run(flush_gateway_requests(FakePrismaClient(), acc, buffer))
+
+    assert lock.held == []
+    assert acc.drain() == {
+        GatewayRequestKey(date=_today(), category="llm", route="/chat/completions"): (
+            GatewayRequestCounts(successful_requests=1, failed_requests=1)
+        )
+    }
diff --git a/tests/test_litellm/proxy/db/test_health_check_latest.py b/tests/test_litellm/proxy/db/test_health_check_latest.py
new file mode 100644
index 00000000000..529e4d8f2e9
--- /dev/null
+++ b/tests/test_litellm/proxy/db/test_health_check_latest.py
@@ -0,0 +1,111 @@
+from datetime import datetime, timezone
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+from litellm.proxy.db.health_check_latest import (
+    LATEST_HEALTH_CHECKS_FOR_MODELS_SQL,
+    LATEST_HEALTH_CHECKS_SQL,
+    fetch_latest_health_checks,
+    fetch_latest_health_checks_for_models,
+)
+
+
+def _prisma(rows):
+    prisma = MagicMock()
+    prisma.db.query_raw = AsyncMock(return_value=rows)
+    return prisma
+
+
+def _raw_row(**overrides):
+    row = {
+        "health_check_id": "hc-1",
+        "model_name": "gpt-4",
+        "model_id": "deployment-abc",
+        "status": "healthy",
+        "healthy_count": 1,
+        "unhealthy_count": 0,
+        "error_message": None,
+        "response_time_ms": 12.5,
+        "details": None,
+        "checked_by": "pod-1",
+        "checked_at": "2026-08-25T00:00:00+00:00",
+        "created_at": "2026-08-25T00:00:00+00:00",
+        "updated_at": "2026-08-25T00:00:00+00:00",
+    }
+    return {**row, **overrides}
+
+
+@pytest.mark.asyncio
+async def test_fetch_all_runs_one_distinct_on_query_with_no_parameters():
+    """The dedup must be in the SQL: prisma find_many(distinct=...) streams the whole history table."""
+    prisma = _prisma([])
+    assert await fetch_latest_health_checks(prisma) == ()
+    assert prisma.db.query_raw.await_args.args == (LATEST_HEALTH_CHECKS_SQL,)
+    assert 'DISTINCT ON ("model_id", "model_name")' in LATEST_HEALTH_CHECKS_SQL
+    assert '"checked_at" DESC' in LATEST_HEALTH_CHECKS_SQL
+
+
+@pytest.mark.asyncio
+async def test_raw_datetimes_come_back_tz_aware_with_or_without_an_offset():
+    """The save path subtracts checked_at from datetime.now(timezone.utc); a naive value would TypeError."""
+    naive = _raw_row(health_check_id="hc-naive", model_id=None, checked_at="2026-08-25T00:00:00")
+    aware = _raw_row(health_check_id="hc-aware", checked_at="2026-08-25T01:00:00+02:00")
+    rows = await fetch_latest_health_checks(_prisma([naive, aware]))
+    assert {row.health_check_id: (row.model_id, row.checked_at) for row in rows} == {
+        "hc-naive": (None, datetime(2026, 8, 25, 0, 0, tzinfo=timezone.utc)),
+        "hc-aware": ("deployment-abc", datetime(2026, 8, 24, 23, 0, tzinfo=timezone.utc)),
+    }
+
+
+@pytest.mark.asyncio
+async def test_json_details_decode_from_text_and_pass_through_as_dict():
+    rows = await fetch_latest_health_checks(
+        _prisma(
+            [
+                _raw_row(health_check_id="text", details='{"region": "eu"}'),
+                _raw_row(health_check_id="dict", details={"region": "us"}),
+                _raw_row(health_check_id="none", details=None),
+            ]
+        )
+    )
+    assert {row.health_check_id: row.details for row in rows} == {
+        "text": {"region": "eu"},
+        "dict": {"region": "us"},
+        "none": None,
+    }
+
+
+@pytest.mark.asyncio
+async def test_fetch_all_degrades_to_no_rows_when_the_query_fails():
+    prisma = _prisma([])
+    prisma.db.query_raw.side_effect = RuntimeError("db down")
+    assert await fetch_latest_health_checks(prisma) == ()
+
+
+@pytest.mark.asyncio
+async def test_fetch_all_degrades_to_no_rows_for_a_malformed_row():
+    assert await fetch_latest_health_checks(_prisma([{"unexpected": "shape"}])) == ()
+
+
+@pytest.mark.asyncio
+async def test_fetch_for_models_binds_the_page_as_the_only_parameter():
+    prisma = _prisma([_raw_row()])
+    rows = await fetch_latest_health_checks_for_models(prisma, ("gpt-4", "claude-opus"))
+    assert prisma.db.query_raw.await_args.args == (LATEST_HEALTH_CHECKS_FOR_MODELS_SQL, ["gpt-4", "claude-opus"])
+    assert [row.model_name for row in rows] == ["gpt-4"]
+    assert 'WHERE "model_name" = ANY($1)' in LATEST_HEALTH_CHECKS_FOR_MODELS_SQL
+
+
+@pytest.mark.asyncio
+async def test_fetch_for_models_skips_the_database_for_an_empty_page():
+    prisma = _prisma([])
+    assert await fetch_latest_health_checks_for_models(prisma, ()) == ()
+    prisma.db.query_raw.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_fetch_for_models_degrades_to_no_rows_when_the_query_fails():
+    prisma = _prisma([])
+    prisma.db.query_raw.side_effect = RuntimeError("db down")
+    assert await fetch_latest_health_checks_for_models(prisma, ("gpt-4",)) == ()
diff --git a/tests/test_litellm/proxy/db/test_pgbouncer.py b/tests/test_litellm/proxy/db/test_pgbouncer.py
new file mode 100644
index 00000000000..7b5a0bf10f9
--- /dev/null
+++ b/tests/test_litellm/proxy/db/test_pgbouncer.py
@@ -0,0 +1,868 @@
+import base64
+import configparser
+import json
+import logging
+import os
+import signal
+import socket
+import stat
+import sys
+import tempfile
+import textwrap
+import time
+import urllib.parse
+from collections import deque
+from collections.abc import Callable
+from concurrent.futures import ThreadPoolExecutor
+from datetime import datetime, timedelta, timezone
+from pathlib import Path
+from typing import Final, cast
+
+import pytest
+
+from litellm._logging import verbose_proxy_logger
+from litellm.proxy.db.pgbouncer import (
+    PGBOUNCER_POOLED_ENV_VAR,
+    PgBouncerError,
+    PgBouncerPlan,
+    PgBouncerProcess,
+    PgBouncerSettings,
+    PgBouncerTokenRefresher,
+    PgBouncerTokenSource,
+    database_url_is_pooled,
+    export_pooled_database_url,
+    install_pgbouncer_token,
+    pgbouncer_version,
+    plan_pgbouncer,
+    start_in_container_pgbouncer,
+    unix_socket_path,
+    write_pgbouncer_ini,
+    write_userlist,
+)
+from litellm.proxy.db.token_auth import AzureEntraTokenAuth, IAMEndpoint
+
+UPSTREAM: Final = (
+    "postgresql://app:p%40ss%27w@db.internal:5433/litellm"
+    "?schema=public&connection_limit=10&pool_timeout=20"
+    "&sslmode=require&sslaccept=strict&sslcert=/certs/ca.pem"
+    "&options=-c%20statement_timeout%3D7000%20-c%20lock_timeout%3D3000"
+)
+SETTINGS: Final = PgBouncerSettings(enabled=True, port=6543, max_db_connections=8, max_client_conn=400)
+
+
+def _plan(url: str = UPSTREAM, run_as_user: str | None = None) -> PgBouncerPlan:
+    plan: Final = plan_pgbouncer(url, SETTINGS, Path("/run/pgb"), run_as_user)
+    assert isinstance(plan, PgBouncerPlan), plan
+    return plan
+
+
+def _ini(plan: PgBouncerPlan) -> configparser.ConfigParser:
+    parser: Final = configparser.ConfigParser(interpolation=None)
+    parser.read_string(plan.ini)
+    return parser
+
+
+def _query(url: str) -> dict[str, str]:
+    return dict(urllib.parse.parse_qsl(urllib.parse.urlsplit(url).query, keep_blank_values=True))
+
+
+class TestPlanPgBouncer:
+    def test_upstream_route_and_timeouts_move_into_the_pgbouncer_config_without_the_password(self):
+        ini: Final = _ini(_plan())
+        assert ini["databases"]["litellm"] == (
+            "host='db.internal' port=5433 dbname='litellm' user='app' "
+            "connect_query='SET statement_timeout TO ''7000''; SET lock_timeout TO ''3000'''"
+        )
+
+    def test_the_auth_file_holds_the_upstream_password_and_the_pool_users_own(self):
+        plan: Final = _plan()
+        assert plan.upstream_password == "p@ss'w"
+        assert plan.userlist("p@ss'w") == f'"app" "p@ss\'w"\n"litellm_pgbouncer" "{plan.pool_password}"\n'
+
+    def test_a_token_with_quotes_is_escaped_the_way_pgbouncer_reads_it(self):
+        assert _plan().userlist('to"ken').startswith('"app" "to""ken"\n')
+
+    def test_an_upstream_without_a_port_is_reached_on_the_postgres_default(self):
+        ini: Final = _ini(_plan("postgresql://app:pw@db/litellm"))
+        assert ini["databases"]["litellm"] == "host='db' port=5432 dbname='litellm' user='app'"
+
+    def test_pool_is_sized_from_settings_in_transaction_mode(self):
+        pgb: Final = _ini(_plan())["pgbouncer"]
+        assert pgb["pool_mode"] == "transaction"
+        assert pgb["max_db_connections"] == "8"
+        assert pgb["default_pool_size"] == "8"
+        assert pgb["max_client_conn"] == "400"
+        assert pgb["auth_type"] == "scram-sha-256"
+        assert pgb["listen_addr"] == "127.0.0.1"
+        assert pgb["listen_port"] == "6543"
+        assert pgb["auth_file"] == "/run/pgb/userlist.txt"
+        assert pgb["unix_socket_dir"] == "/run/pgb"
+
+    def test_the_pool_user_can_read_the_pgbouncer_console(self):
+        assert _ini(_plan())["pgbouncer"]["stats_users"] == "litellm_pgbouncer"
+
+    def test_a_database_user_named_like_the_pool_user_is_refused(self):
+        outcome: Final = plan_pgbouncer(
+            "postgresql://litellm_pgbouncer:pw@db/litellm", SETTINGS, Path("/run/pgb"), None
+        )
+        assert isinstance(outcome, PgBouncerError)
+        assert "litellm_pgbouncer" in outcome.reason
+
+    def test_pooled_url_points_prisma_at_loopback_as_the_pool_user_without_prepared_statements(self):
+        plan: Final = _plan()
+        pooled: Final = urllib.parse.urlsplit(plan.pooled_url)
+        assert (pooled.hostname, pooled.port, pooled.path) == ("127.0.0.1", 6543, "/litellm")
+        assert (pooled.username, pooled.password) == ("litellm_pgbouncer", plan.pool_password)
+        assert len(plan.pool_password) >= 32
+        assert "p%40ss" not in plan.pooled_url
+        assert _query(plan.pooled_url) == {
+            "schema": "public",
+            "connection_limit": "10",
+            "pool_timeout": "20",
+            "pgbouncer": "true",
+        }
+
+    @pytest.mark.parametrize("hop_param", ["channel_binding=require", "gssencmode=require"])
+    def test_transport_params_for_the_postgres_hop_stay_off_the_plain_tcp_loopback_url(self, hop_param: str):
+        pooled: Final = _plan(f"postgresql://app:pw@db/litellm?connection_limit=5&{hop_param}").pooled_url
+        assert _query(pooled) == {"connection_limit": "5", "pgbouncer": "true"}
+
+    def test_verified_tls_becomes_server_side_verify_full_with_a_ca_copy_in_the_runtime_dir(self):
+        plan: Final = _plan()
+        pgb: Final = _ini(plan)["pgbouncer"]
+        assert pgb["server_tls_sslmode"] == "verify-full"
+        assert pgb["server_tls_ca_file"] == "/run/pgb/server-ca.pem"
+        assert plan.ca_source == "/certs/ca.pem"
+
+    def test_unverified_require_stays_require_without_a_ca_file(self):
+        plan: Final = _plan("postgresql://app:pw@db/litellm?sslmode=require")
+        pgb: Final = _ini(plan)["pgbouncer"]
+        assert pgb["server_tls_sslmode"] == "require"
+        assert "server_tls_ca_file" not in pgb
+        assert plan.ca_source is None
+
+    def test_every_plan_gets_its_own_pool_password(self):
+        assert _plan().pool_password != _plan().pool_password
+
+    def test_no_tls_params_default_to_prefer(self):
+        assert _ini(_plan("postgresql://app:pw@db/litellm"))["pgbouncer"]["server_tls_sslmode"] == "prefer"
+
+    def test_verification_without_a_ca_bundle_is_refused(self):
+        outcome: Final = plan_pgbouncer(
+            "postgresql://app:pw@db/litellm?sslmode=require&sslaccept=strict", SETTINGS, Path("/run/pgb"), None
+        )
+        assert isinstance(outcome, PgBouncerError)
+        assert "sslcert" in outcome.reason
+
+    def test_client_certificates_are_refused(self):
+        outcome: Final = plan_pgbouncer(
+            "postgresql://app:pw@db/litellm?sslidentity=/certs/client.p12", SETTINGS, Path("/run/pgb"), None
+        )
+        assert isinstance(outcome, PgBouncerError)
+        assert "sslidentity" in outcome.reason
+
+    @pytest.mark.parametrize(
+        "url",
+        [
+            "postgresql://app:pw@db",
+            "postgresql://:pw@db/litellm",
+            "postgresql://app:pw@/litellm",
+        ],
+    )
+    def test_urls_missing_a_route_are_refused(self, url: str):
+        outcome: Final = plan_pgbouncer(url, SETTINGS, Path("/run/pgb"), None)
+        assert isinstance(outcome, PgBouncerError)
+
+    def test_a_url_without_a_password_plans_for_a_token_to_be_installed_later(self):
+        plan: Final = _plan("postgresql://app@db/litellm")
+        assert plan.upstream_password is None
+        assert plan.userlist("minted").startswith('"app" "minted"\n')
+
+    def test_every_options_spelling_becomes_a_set_statement(self):
+        options: Final = urllib.parse.quote("-c a=1 -cb=2 --c=3")
+        ini: Final = _ini(_plan(f"postgresql://app:pw@db/litellm?options={options}"))
+        assert ini["databases"]["litellm"].endswith("connect_query='SET a TO ''1''; SET b TO ''2''; SET c TO ''3'''")
+
+    def test_options_that_are_not_settings_are_refused(self):
+        outcome: Final = plan_pgbouncer(
+            "postgresql://app:pw@db/litellm?options=-c%20search_path", SETTINGS, Path("/run/pgb"), None
+        )
+        assert isinstance(outcome, PgBouncerError)
+        assert "options" in outcome.reason
+
+    def test_run_as_user_is_only_written_when_given(self):
+        assert _ini(_plan(run_as_user="nobody"))["pgbouncer"]["user"] == "nobody"
+        assert "user" not in _ini(_plan())["pgbouncer"]
+
+
+class TestWritePgBouncerFiles:
+    def test_files_hold_the_plan_and_are_private_to_the_owner(self, tmp_path: Path):
+        plan: Final = _plan("postgresql://app:pw@db/litellm")
+        ini_path: Final = write_pgbouncer_ini(plan, tmp_path, None)
+        assert isinstance(ini_path, Path), ini_path
+        userlist_path: Final = write_userlist(plan.userlist("pw"), tmp_path, None)
+        assert ini_path == tmp_path / "pgbouncer.ini"
+        assert userlist_path == tmp_path / "userlist.txt"
+        assert ini_path.read_text() == plan.ini
+        assert userlist_path.read_text() == plan.userlist("pw")
+        for path in (ini_path, userlist_path):
+            assert stat.S_IMODE(path.stat().st_mode) == 0o600
+        assert not (tmp_path / "server-ca.pem").exists()
+
+    def test_the_ca_bundle_is_copied_next_to_the_ini_pgbouncer_reads(self, tmp_path: Path):
+        bundle: Final = tmp_path / "rds-root.pem"
+        bundle.write_text("-----BEGIN CERTIFICATE-----\nMIIB\n-----END CERTIFICATE-----\n")
+        runtime_dir: Final = tmp_path / "run"
+        runtime_dir.mkdir()
+        plan: Final = plan_pgbouncer(
+            f"postgresql://app:pw@db/litellm?sslmode=verify-full&sslcert={bundle}", SETTINGS, runtime_dir, None
+        )
+        assert isinstance(plan, PgBouncerPlan), plan
+        ini_path: Final = write_pgbouncer_ini(plan, runtime_dir, None)
+        assert isinstance(ini_path, Path), ini_path
+        ca_file: Final = Path(_ini(plan)["pgbouncer"]["server_tls_ca_file"])
+        assert ca_file.parent == runtime_dir
+        assert ca_file.read_text() == bundle.read_text()
+
+    def test_an_unreadable_ca_bundle_is_reported(self, tmp_path: Path):
+        plan: Final = plan_pgbouncer(
+            f"postgresql://app:pw@db/litellm?sslmode=verify-full&sslcert={tmp_path / 'missing.pem'}",
+            SETTINGS,
+            tmp_path,
+            None,
+        )
+        assert isinstance(plan, PgBouncerPlan), plan
+        outcome: Final = write_pgbouncer_ini(plan, tmp_path, None)
+        assert isinstance(outcome, PgBouncerError)
+        assert "missing.pem" in outcome.reason
+        assert not (tmp_path / "pgbouncer.ini").exists()
+
+    def test_rewriting_the_userlist_replaces_it_whole_and_leaves_nothing_else_behind(self, tmp_path: Path):
+        write_userlist('"app" "first"\n', tmp_path, None)
+        with open(tmp_path / "userlist.txt", encoding="utf-8") as before_rewrite:
+            write_userlist('"app" "second"\n', tmp_path, None)
+            assert before_rewrite.read() == '"app" "first"\n'
+        assert (tmp_path / "userlist.txt").read_text() == '"app" "second"\n'
+        assert stat.S_IMODE((tmp_path / "userlist.txt").stat().st_mode) == 0o600
+        assert sorted(path.name for path in tmp_path.iterdir()) == ["userlist.txt"]
+
+
+class TestPooledUrlMarker:
+    def test_exporting_the_pooled_url_marks_it_for_the_workers(self, monkeypatch: pytest.MonkeyPatch):
+        monkeypatch.setenv(PGBOUNCER_POOLED_ENV_VAR, "")
+        monkeypatch.delenv(PGBOUNCER_POOLED_ENV_VAR)
+        monkeypatch.setenv("DATABASE_URL", "postgresql://app:token@db/litellm")
+        assert not database_url_is_pooled()
+        export_pooled_database_url("postgresql://litellm_pgbouncer:pw@127.0.0.1:6432/litellm?pgbouncer=true")
+        assert os.environ["DATABASE_URL"] == "postgresql://litellm_pgbouncer:pw@127.0.0.1:6432/litellm?pgbouncer=true"
+        assert database_url_is_pooled()
+        assert PGBOUNCER_POOLED_ENV_VAR == "LITELLM_PGBOUNCER_POOLED_DATABASE_URL"
+
+
+def _bound_port(sock: socket.socket) -> int:
+    return cast(tuple[str, int], sock.getsockname())[1]
+
+
+def _free_port() -> int:
+    with socket.socket() as probe:
+        probe.bind(("127.0.0.1", 0))
+        return _bound_port(probe)
+
+
+def _fake_pooler(
+    tmp_path: Path,
+    port: int,
+    exit_immediately: bool = False,
+    port_file: Path | None = None,
+    bind_delay_seconds: float = 0.0,
+    version_banner: str = "PgBouncer 1.25.2\nlibevent 2.1.13-stable",
+    auth_log: Path | None = None,
+) -> Path:
+    """An executable that listens like PgBouncer: on the TCP port first, then on ``.s.PGSQL.<port>`` in the socket dir.
+
+    Port and socket dir come from the ini it is given, else from ``port`` and
+    ``tmp_path``. With ``port_file`` each start reads the port from that file
+    instead. ``bind_delay_seconds`` holds the bind back, like a slow start.
+    ``--version`` prints ``version_banner``. With ``auth_log`` it appends the
+    ``auth_file`` it reads at startup and on every SIGHUP, one line per read,
+    like PgBouncer loading its credentials.
+    """
+    script: Final = tmp_path / "fake-pgbouncer"
+    script.write_text(
+        textwrap.dedent(
+            f"""\
+            #!{sys.executable}
+            import configparser, os, pathlib, select, signal, socket, sys, time
+            if sys.argv[1:] == ["--version"]:
+                print({version_banner!r})
+                sys.exit(0)
+            if {exit_immediately!r}:
+                sys.exit(3)
+            ini = configparser.ConfigParser()
+            ini.read(sys.argv[1:2])
+            if not {auth_log is None!r}:
+                def load_auth_file(*_):
+                    with open({str(auth_log)!r}, "a") as log:
+                        log.write(repr(pathlib.Path(ini.get("pgbouncer", "auth_file")).read_text()) + "\\n")
+                load_auth_file()
+                signal.signal(signal.SIGHUP, load_auth_file)
+            port = ini.getint("pgbouncer", "listen_port", fallback={port})
+            if not {port_file is None!r}:
+                port = int(pathlib.Path({str(port_file)!r}).read_text())
+            socket_dir = ini.get("pgbouncer", "unix_socket_dir", fallback={str(tmp_path)!r})
+            socket_path = f"{{socket_dir}}/.s.PGSQL.{{port}}"
+            time.sleep({bind_delay_seconds!r})
+            listener = socket.socket()
+            listener.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+            listener.bind(("127.0.0.1", port))
+            listener.listen()
+            if os.path.exists(socket_path):
+                os.unlink(socket_path)
+            unix_listener = socket.socket(socket.AF_UNIX)
+            unix_listener.bind(socket_path)
+            unix_listener.listen()
+            while True:
+                for ready in select.select([listener, unix_listener], [], [])[0]:
+                    conn, _ = ready.accept()
+                    conn.close()
+            """
+        )
+    )
+    script.chmod(0o700)
+    return script
+
+
+def _listening(port: int) -> bool:
+    try:
+        with socket.create_connection(("127.0.0.1", port), timeout=0.5):
+            return True
+    except OSError:
+        return False
+
+
+def _wait_until(condition: Callable[[], bool], timeout_seconds: float = 5.0) -> bool:
+    deadline: Final = time.monotonic() + timeout_seconds
+    while time.monotonic() < deadline:
+        if condition():
+            return True
+        time.sleep(0.05)
+    return False
+
+
+class TestPgBouncerProcess:
+    def test_start_waits_for_the_listener_and_stop_ends_it(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port)),), port=port, socket_path=unix_socket_path(tmp_path, port)
+        )
+        assert pooler.start() is None
+        assert _listening(port)
+        pid: Final = pooler.pid
+        assert pid is not None
+        pooler.stop()
+        assert _wait_until(lambda: not _listening(port))
+        with pytest.raises(ProcessLookupError):
+            os.kill(pid, 0)
+
+    def test_a_crashed_pooler_is_restarted_with_a_new_pid(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            restart_delay_seconds=0.1,
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        os.kill(first_pid, signal.SIGKILL)
+        assert _wait_until(lambda: pooler.pid not in (None, first_pid) and _listening(port))
+        pooler.stop()
+        assert _wait_until(lambda: not _listening(port))
+
+    def test_a_failed_restart_is_retried_until_the_pooler_is_back(
+        self, tmp_path: Path, caplog: pytest.LogCaptureFixture
+    ):
+        port: Final = _free_port()
+        script: Final = _fake_pooler(tmp_path, port)
+        pooler: Final = PgBouncerProcess(
+            argv=(str(script),), port=port, socket_path=unix_socket_path(tmp_path, port), restart_delay_seconds=0.1
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        hidden: Final = script.rename(tmp_path / "hidden")
+        with caplog.at_level(logging.ERROR, logger=verbose_proxy_logger.name):
+            os.kill(first_pid, signal.SIGKILL)
+            assert _wait_until(lambda: any("could not be restarted" in record.message for record in caplog.records))
+            assert not _listening(port)
+            hidden.rename(script)
+            assert _wait_until(lambda: pooler.pid not in (None, first_pid) and _listening(port))
+        pooler.stop()
+        assert _wait_until(lambda: not _listening(port))
+
+    def test_a_replacement_that_never_listens_is_replaced_again(self, tmp_path: Path, caplog: pytest.LogCaptureFixture):
+        port: Final = _free_port()
+        port_file: Final = tmp_path / "port"
+        port_file.write_text(str(port))
+        script: Final = _fake_pooler(tmp_path, port, port_file=port_file)
+        pooler: Final = PgBouncerProcess(
+            argv=(str(script),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            restart_delay_seconds=0.1,
+            ready_timeout_seconds=0.3,
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        wrong_port: Final = _free_port()
+        port_file.write_text(str(wrong_port))
+        with caplog.at_level(logging.ERROR, logger=verbose_proxy_logger.name):
+            os.kill(first_pid, signal.SIGKILL)
+            assert _wait_until(lambda: _listening(wrong_port))
+            assert _wait_until(lambda: any("did not start listening" in record.message for record in caplog.records))
+            port_file.write_text(str(port))
+            assert _wait_until(lambda: _listening(port))
+            assert _wait_until(lambda: not _listening(wrong_port))
+        pooler.stop()
+        assert _wait_until(lambda: not _listening(port))
+
+    def test_stopping_during_the_restart_delay_leaves_no_pooler_behind(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            restart_delay_seconds=0.3,
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        os.kill(first_pid, signal.SIGKILL)
+        assert _wait_until(lambda: not _listening(port))
+        pooler.stop()
+        time.sleep(1.0)
+        assert not _listening(port)
+        assert pooler.pid == first_pid
+
+    def test_a_stopped_pooler_is_not_restarted(self, tmp_path: Path, caplog: pytest.LogCaptureFixture):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            restart_delay_seconds=0.1,
+        )
+        assert pooler.start() is None
+        with caplog.at_level(logging.ERROR, logger=verbose_proxy_logger.name):
+            pooler.stop()
+            time.sleep(0.5)
+        assert not _listening(port)
+        assert caplog.records == []
+
+    def test_a_pooler_that_exits_during_startup_is_reported(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port, exit_immediately=True)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+        )
+        outcome: Final = pooler.start()
+        assert isinstance(outcome, PgBouncerError)
+        assert "status 3" in outcome.reason
+
+    def test_a_missing_binary_is_reported(self, tmp_path: Path):
+        outcome: Final = PgBouncerProcess(
+            argv=("/nonexistent/pgbouncer",), port=_free_port(), socket_path=tmp_path / "sock"
+        ).start()
+        assert isinstance(outcome, PgBouncerError)
+        assert "/nonexistent/pgbouncer" in outcome.reason
+
+    def test_a_port_owned_by_someone_else_is_refused_before_spawning(self, tmp_path: Path):
+        with socket.socket() as squatter:
+            squatter.bind(("127.0.0.1", 0))
+            squatter.listen()
+            port: Final = _bound_port(squatter)
+            pooler: Final = PgBouncerProcess(
+                argv=(str(_fake_pooler(tmp_path, port)),), port=port, socket_path=unix_socket_path(tmp_path, port)
+            )
+            outcome: Final = pooler.start()
+        assert isinstance(outcome, PgBouncerError)
+        assert f"127.0.0.1:{port} is already in use" in outcome.reason
+        assert pooler.pid is None
+
+    def test_a_replacement_waits_until_a_squatter_leaves_the_port(
+        self, tmp_path: Path, caplog: pytest.LogCaptureFixture
+    ):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            restart_delay_seconds=0.5,
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        os.kill(first_pid, signal.SIGKILL)
+        assert _wait_until(lambda: not _listening(port))
+        with socket.socket() as squatter, caplog.at_level(logging.ERROR, logger=verbose_proxy_logger.name):
+            squatter.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+            squatter.bind(("127.0.0.1", port))
+            squatter.listen()
+            assert _wait_until(lambda: any("already in use" in record.message for record in caplog.records))
+            assert pooler.pid == first_pid
+        assert _wait_until(lambda: pooler.pid not in (None, first_pid) and _listening(port))
+        pooler.stop()
+        assert _wait_until(lambda: not _listening(port))
+
+    def test_a_listener_that_grabs_the_port_after_the_spawn_is_not_taken_for_the_pooler(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port, bind_delay_seconds=0.5)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            ready_timeout_seconds=3.0,
+        )
+        with socket.socket() as squatter, ThreadPoolExecutor(max_workers=1) as starter:
+            squatter.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+            starting: Final = starter.submit(pooler.start)
+            assert _wait_until(lambda: pooler.pid is not None)
+            squatter.bind(("127.0.0.1", port))
+            squatter.listen()
+            outcome: Final = starting.result()
+        assert isinstance(outcome, PgBouncerError)
+        assert "exited with status 1" in outcome.reason
+
+    def test_a_port_served_by_a_stranger_while_the_pooler_is_still_starting_is_reported(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port, bind_delay_seconds=30.0)),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            ready_timeout_seconds=0.5,
+        )
+        with socket.socket() as squatter, ThreadPoolExecutor(max_workers=1) as starter:
+            squatter.setsockopt(socket.SOL_SOCKET, socket.SO_REUSEADDR, 1)
+            starting: Final = starter.submit(pooler.start)
+            assert _wait_until(lambda: pooler.pid is not None)
+            squatter.bind(("127.0.0.1", port))
+            squatter.listen()
+            outcome: Final = starting.result()
+        assert isinstance(outcome, PgBouncerError)
+        assert f"127.0.0.1:{port} is served by another process" in outcome.reason
+        pid: Final = pooler.pid
+        assert pid is not None
+        with pytest.raises(ProcessLookupError):
+            os.kill(pid, 0)
+
+    def test_a_pooler_that_never_listens_times_out(self, tmp_path: Path):
+        port: Final = _free_port()
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, _free_port())),),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            ready_timeout_seconds=0.5,
+        )
+        outcome: Final = pooler.start()
+        assert isinstance(outcome, PgBouncerError)
+        assert "did not start listening" in outcome.reason
+        pid: Final = pooler.pid
+        assert pid is not None
+        with pytest.raises(ProcessLookupError):
+            os.kill(pid, 0)
+
+
+NOW: Final = datetime(2026, 9, 10, 12, 0, tzinfo=timezone.utc)
+ENDPOINT: Final = IAMEndpoint(host="db", port="5432", user="app", name="litellm")
+
+
+def _entra_jwt(expires_at: datetime) -> str:
+    payload: Final = base64.urlsafe_b64encode(json.dumps({"exp": int(expires_at.timestamp())}).encode())
+    return f"aGVhZGVy.{payload.rstrip(b'=').decode()}.c2ln"
+
+
+def _token_source(*tokens: str | Exception) -> PgBouncerTokenSource:
+    """A token source handing out ``tokens`` in order, raising the exceptions among them, then repeating the last."""
+    pending: Final = deque(tokens)
+
+    def provide() -> str:
+        outcome: Final = pending.popleft() if len(pending) > 1 else pending[0]
+        if isinstance(outcome, Exception):
+            raise outcome
+        return outcome
+
+    return PgBouncerTokenSource(auth=AzureEntraTokenAuth(token_provider=provide), endpoint=ENDPOINT)
+
+
+class TestPgBouncerTokenRefresher:
+    def _refresher(
+        self,
+        source: PgBouncerTokenSource,
+        installed: list[str],
+        install: Callable[[str], None] | None = None,
+        **timing: float,
+    ) -> PgBouncerTokenRefresher:
+        return PgBouncerTokenRefresher(
+            source,
+            install if install is not None else installed.append,
+            now=lambda: NOW.replace(tzinfo=None),
+            **timing,
+        )
+
+    def test_the_next_refresh_is_due_a_buffer_before_the_token_expires(self):
+        installed: Final[list[str]] = []
+        token: Final = _entra_jwt(NOW + timedelta(hours=1))
+        refresher: Final = self._refresher(_token_source(token), installed, buffer_seconds=180)
+        assert refresher.refresh() == 3600 - 180
+        assert installed == [token]
+
+    def test_a_token_whose_expiry_cannot_be_read_is_refreshed_on_the_fallback_interval(self):
+        installed: Final[list[str]] = []
+        refresher: Final = self._refresher(_token_source("opaque token"), installed, fallback_seconds=600)
+        assert refresher.refresh() == 600
+        assert installed == ["opaque token"]
+
+    def test_a_token_already_inside_the_buffer_is_refreshed_after_the_retry_delay(self):
+        token: Final = _entra_jwt(NOW + timedelta(seconds=100))
+        refresher: Final = self._refresher(_token_source(token), [], buffer_seconds=180, retry_seconds=30)
+        assert refresher.refresh() == 30
+
+    def test_the_token_reaches_the_auth_file_in_wire_form_not_url_encoded(self):
+        installed: Final[list[str]] = []
+        self._refresher(_token_source("to ken/with+odd=chars"), installed).refresh()
+        assert installed == ["to ken/with+odd=chars"]
+
+    def test_a_failed_mint_is_reported_and_installs_nothing(self):
+        installed: Final[list[str]] = []
+        outcome: Final = self._refresher(_token_source(RuntimeError("no credential")), installed).refresh()
+        assert isinstance(outcome, PgBouncerError)
+        assert "Azure Entra token" in outcome.reason
+        assert "no credential" in outcome.reason
+        assert installed == []
+
+    def test_a_token_pgbouncer_cannot_hold_is_refused(self):
+        installed: Final[list[str]] = []
+        outcome: Final = self._refresher(_token_source("x" * 2048), installed).refresh()
+        assert isinstance(outcome, PgBouncerError)
+        assert "2047" in outcome.reason
+        assert installed == []
+
+    def test_an_auth_file_that_cannot_be_written_is_reported_not_raised(self):
+        def refuse(_: str) -> None:
+            raise PermissionError("read-only runtime dir")
+
+        outcome: Final = self._refresher(_token_source("token"), [], install=refuse).refresh()
+        assert isinstance(outcome, PgBouncerError)
+        assert "read-only runtime dir" in outcome.reason
+
+    def test_start_fails_when_the_first_token_cannot_be_minted_and_schedules_nothing(self):
+        installed: Final[list[str]] = []
+        refresher: Final = self._refresher(
+            _token_source(RuntimeError("no credential"), "later"), installed, fallback_seconds=0.05
+        )
+        assert isinstance(refresher.start(), PgBouncerError)
+        time.sleep(0.3)
+        assert installed == []
+
+    def test_a_failed_renewal_keeps_the_previous_token_until_the_retry_succeeds(self, caplog: pytest.LogCaptureFixture):
+        installed: Final[list[str]] = []
+        refresher: Final = self._refresher(
+            _token_source("first", RuntimeError("blip"), "third"),
+            installed,
+            fallback_seconds=0.05,
+            retry_seconds=0.05,
+        )
+        with caplog.at_level(logging.ERROR, logger=verbose_proxy_logger.name):
+            assert refresher.start() is None
+            assert installed == ["first"]
+            assert _wait_until(lambda: "third" in installed)
+        assert installed[:2] == ["first", "third"]
+        assert any("keeps its current Azure Entra token" in record.message for record in caplog.records)
+        refresher.stop()
+        settled: Final = len(installed)
+        time.sleep(0.3)
+        assert len(installed) == settled
+
+
+def _runtime_dir_listening_on(port: int) -> Path:
+    matches: Final = tuple(
+        ini.parent
+        for ini in Path(tempfile.gettempdir()).glob("litellm-pgbouncer-*/pgbouncer.ini")
+        if f"listen_port = {port}\n" in ini.read_text()
+    )
+    assert len(matches) == 1, matches
+    return matches[0]
+
+
+class TestStartInContainerPgBouncer:
+    def test_returns_the_loopback_url_once_the_pooler_listens(self, tmp_path: Path):
+        port: Final = _free_port()
+        auth_log: Final = tmp_path / "auth.log"
+        binary: Final = _fake_pooler(tmp_path, port, auth_log=auth_log)
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(binary))
+        pooled: Final = start_in_container_pgbouncer(settings, "postgresql://app:pw@db/litellm?connection_limit=5")
+        assert isinstance(pooled, str), pooled
+        parsed: Final = urllib.parse.urlsplit(pooled)
+        assert (parsed.username, parsed.hostname, parsed.port, parsed.path) == (
+            "litellm_pgbouncer",
+            "127.0.0.1",
+            port,
+            "/litellm",
+        )
+        assert _query(pooled) == {"connection_limit": "5", "pgbouncer": "true"}
+        assert _listening(port)
+        assert auth_log.read_text() == repr(f'"app" "pw"\n"litellm_pgbouncer" "{parsed.password}"\n') + "\n"
+
+    @pytest.mark.filterwarnings("ignore:This process .* is multi-threaded:DeprecationWarning")
+    def test_a_forked_worker_exiting_leaves_the_pooler_and_its_files_to_the_parent(self, tmp_path: Path):
+        port: Final = _free_port()
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(_fake_pooler(tmp_path, port)))
+        exit_hooks: Final[list[Callable[[], None]]] = []
+        pooled: Final = start_in_container_pgbouncer(
+            settings, "postgresql://app:pw@db/litellm", register_exit_hook=exit_hooks.append
+        )
+        assert isinstance(pooled, str), pooled
+        runtime_dir: Final = _runtime_dir_listening_on(port)
+
+        worker: Final = os.fork()
+        if worker == 0:
+            try:
+                for hook in exit_hooks:
+                    hook()
+            finally:
+                os._exit(0)
+        if not _wait_until(lambda: os.waitpid(worker, os.WNOHANG) != (0, 0)):
+            os.kill(worker, signal.SIGKILL)
+            pytest.fail("the forked worker did not exit: an exit hook blocked on state inherited from the parent")
+        assert _listening(port)
+        assert (runtime_dir / "pgbouncer.ini").exists()
+
+        for hook in exit_hooks:
+            hook()
+        assert _wait_until(lambda: not _listening(port))
+        assert not runtime_dir.exists()
+
+    def test_a_bad_upstream_url_is_reported_without_starting_anything(self, tmp_path: Path):
+        port: Final = _free_port()
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(_fake_pooler(tmp_path, port)))
+        outcome: Final = start_in_container_pgbouncer(settings, "postgresql://app:pw@db")
+        assert isinstance(outcome, PgBouncerError)
+        assert not _listening(port)
+
+    def test_a_passwordless_url_without_token_auth_is_refused_without_starting_anything(self, tmp_path: Path):
+        port: Final = _free_port()
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(_fake_pooler(tmp_path, port)))
+        outcome: Final = start_in_container_pgbouncer(settings, "postgresql://app@db/litellm")
+        assert isinstance(outcome, PgBouncerError)
+        assert "IAM_TOKEN_DB_AUTH" in outcome.reason
+        assert not _listening(port)
+
+    def test_token_auth_mints_the_first_token_into_the_auth_file_before_the_pooler_starts(self, tmp_path: Path):
+        port: Final = _free_port()
+        auth_log: Final = tmp_path / "auth.log"
+        binary: Final = _fake_pooler(tmp_path, port, auth_log=auth_log)
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(binary))
+        token: Final = _entra_jwt(datetime.now(tz=timezone.utc) + timedelta(hours=1))
+        pooled: Final = start_in_container_pgbouncer(
+            settings,
+            "postgresql://app:stale-token@db/litellm",
+            token_auth=AzureEntraTokenAuth(token_provider=lambda: token),
+        )
+        assert isinstance(pooled, str), pooled
+        parsed: Final = urllib.parse.urlsplit(pooled)
+        assert parsed.username == "litellm_pgbouncer"
+        assert token not in pooled
+        assert _listening(port)
+        assert auth_log.read_text() == repr(f'"app" "{token}"\n"litellm_pgbouncer" "{parsed.password}"\n') + "\n"
+
+    def test_a_first_token_that_cannot_be_minted_is_reported_without_starting_anything(self, tmp_path: Path):
+        port: Final = _free_port()
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(_fake_pooler(tmp_path, port)))
+
+        def fail() -> str:
+            raise RuntimeError("no Azure credential")
+
+        outcome: Final = start_in_container_pgbouncer(
+            settings, "postgresql://app@db/litellm", token_auth=AzureEntraTokenAuth(token_provider=fail)
+        )
+        assert isinstance(outcome, PgBouncerError)
+        assert "no Azure credential" in outcome.reason
+        assert not _listening(port)
+
+    def test_a_renewed_token_is_written_and_picked_up_by_the_running_and_by_a_restarted_pooler(self, tmp_path: Path):
+        port: Final = _free_port()
+        auth_log: Final = tmp_path / "auth.log"
+        plan: Final = plan_pgbouncer(
+            "postgresql://app@db/litellm", PgBouncerSettings(enabled=True, port=port), tmp_path, None
+        )
+        assert isinstance(plan, PgBouncerPlan), plan
+        ini_path: Final = write_pgbouncer_ini(plan, tmp_path, None)
+        write_userlist(plan.userlist("first"), tmp_path, None)
+        pooler: Final = PgBouncerProcess(
+            argv=(str(_fake_pooler(tmp_path, port, auth_log=auth_log)), str(ini_path)),
+            port=port,
+            socket_path=unix_socket_path(tmp_path, port),
+            restart_delay_seconds=0.1,
+        )
+        assert pooler.start() is None
+        first_pid: Final = pooler.pid
+        assert first_pid is not None
+        install_pgbouncer_token(plan, tmp_path, None, pooler, "second")
+        assert _wait_until(lambda: auth_log.read_text().count("\n") == 2)
+        os.kill(first_pid, signal.SIGKILL)
+        assert _wait_until(lambda: pooler.pid not in (None, first_pid) and _listening(port))
+        pooler.stop()
+        assert auth_log.read_text().splitlines() == [
+            repr(plan.userlist("first")),
+            repr(plan.userlist("second")),
+            repr(plan.userlist("second")),
+        ]
+
+    def test_a_pgbouncer_that_survives_a_failed_tcp_bind_is_refused_without_starting(self, tmp_path: Path):
+        port: Final = _free_port()
+        binary: Final = _fake_pooler(tmp_path, port, version_banner="PgBouncer 1.18.1\nlibevent 2.1.12-stable")
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(binary))
+        outcome: Final = start_in_container_pgbouncer(settings, "postgresql://app:pw@db/litellm")
+        assert isinstance(outcome, PgBouncerError)
+        assert "PgBouncer 1.18" in outcome.reason
+        assert "1.19" in outcome.reason
+        assert not _listening(port)
+
+    def test_the_first_version_that_dies_on_a_failed_tcp_bind_is_accepted(self, tmp_path: Path):
+        port: Final = _free_port()
+        binary: Final = _fake_pooler(tmp_path, port, version_banner="PgBouncer 1.19.0")
+        settings: Final = PgBouncerSettings(enabled=True, port=port, binary=str(binary))
+        pooled: Final = start_in_container_pgbouncer(settings, "postgresql://app:pw@db/litellm")
+        assert isinstance(pooled, str), pooled
+        assert urllib.parse.urlsplit(pooled).port == port
+        assert _listening(port)
+
+
+class TestPgBouncerVersion:
+    def test_reads_major_and_minor_from_the_banner(self, tmp_path: Path):
+        assert pgbouncer_version(str(_fake_pooler(tmp_path, _free_port()))) == (1, 25)
+
+    def test_a_binary_that_cannot_run_is_reported(self, tmp_path: Path):
+        outcome: Final = pgbouncer_version(str(tmp_path / "missing-pgbouncer"))
+        assert isinstance(outcome, PgBouncerError)
+        assert "missing-pgbouncer" in outcome.reason
+
+    def test_a_banner_without_a_version_is_reported(self, tmp_path: Path):
+        outcome: Final = pgbouncer_version(str(_fake_pooler(tmp_path, _free_port(), version_banner="something else")))
+        assert isinstance(outcome, PgBouncerError)
+        assert "something else" in outcome.reason
+
+
+class TestPgBouncerSettings:
+    def test_reads_the_litellm_pgbouncer_env_vars(self, monkeypatch: pytest.MonkeyPatch):
+        monkeypatch.setenv("LITELLM_PGBOUNCER_ENABLED", "true")
+        monkeypatch.setenv("LITELLM_PGBOUNCER_PORT", "7000")
+        monkeypatch.setenv("LITELLM_PGBOUNCER_MAX_DB_CONNECTIONS", "12")
+        settings: Final = PgBouncerSettings()
+        assert (settings.enabled, settings.port, settings.max_db_connections) == (True, 7000, 12)
+
+    def test_defaults_are_off(self, monkeypatch: pytest.MonkeyPatch):
+        monkeypatch.delenv("LITELLM_PGBOUNCER_ENABLED", raising=False)
+        assert PgBouncerSettings().enabled is False
diff --git a/tests/test_litellm/proxy/db/test_prisma_self_heal.py b/tests/test_litellm/proxy/db/test_prisma_self_heal.py
index 10a48941693..e6914213939 100644
--- a/tests/test_litellm/proxy/db/test_prisma_self_heal.py
+++ b/tests/test_litellm/proxy/db/test_prisma_self_heal.py
@@ -626,7 +626,7 @@ async def test_direct_reconnect_probe_success_clears_writer_unavailable(
         database_url="mock://test", proxy_logging_obj=mock_proxy_logging
     )
     writer = MagicMock()
-    writer.query_raw = AsyncMock(return_value=[{"result": 1}])
+    writer.query_raw = AsyncMock(return_value=[{"transaction_read_only": "off"}])
     reader = MagicMock()
     routing = RoutingPrismaWrapper(writer=writer, reader=reader)
     routing._writer_unavailable = True
@@ -636,5 +636,5 @@ async def test_direct_reconnect_probe_success_clears_writer_unavailable(
     with patch.dict(os.environ, {"DATABASE_URL": "postgresql://test"}):
         await client._run_reconnect_cycle(timeout_seconds=5.0)
 
-    writer.query_raw.assert_awaited_once_with("SELECT 1")
+    writer.query_raw.assert_awaited_once_with("SELECT current_setting('transaction_read_only') AS transaction_read_only")
     assert routing.writer_unavailable is False
diff --git a/tests/test_litellm/proxy/db/test_spend_counter_reseed.py b/tests/test_litellm/proxy/db/test_spend_counter_reseed.py
index 8cb3fc665eb..0361d5cfe8f 100644
--- a/tests/test_litellm/proxy/db/test_spend_counter_reseed.py
+++ b/tests/test_litellm/proxy/db/test_spend_counter_reseed.py
@@ -7,6 +7,7 @@ allowed to run: only when the row is missing or belongs to an older window.
 
 from __future__ import annotations
 
+import asyncio
 from datetime import datetime, timedelta, timezone
 from types import SimpleNamespace
 from typing import Final
@@ -14,6 +15,7 @@ from typing import Final
 import pytest
 
 from litellm.caching.dual_cache import DualCache
+from litellm.constants import PROXY_DB_LOOKUP_MAX_CONCURRENCY
 from litellm.proxy.db.spend_counter_reseed import SpendCounterReseed
 
 WINDOW_START = datetime(2026, 8, 1, tzinfo=timezone.utc)
@@ -42,6 +44,19 @@ class _FakeSpendLogsTable:
         return [{by[0]: where.get(by[0]), "_sum": {"spend": self._total}}]
 
 
+class _InFlightCountingTable:
+    def __init__(self) -> None:
+        self.in_flight = 0
+        self.max_in_flight = 0
+
+    async def find_unique(self, where: dict[str, str]) -> SimpleNamespace:
+        self.in_flight += 1
+        self.max_in_flight = max(self.max_in_flight, self.in_flight)
+        await asyncio.sleep(0.001)
+        self.in_flight -= 1
+        return SimpleNamespace(token=where["token"], spend=1.0)
+
+
 class _FakePrismaClient:
     def __init__(
         self,
@@ -55,6 +70,7 @@ class _FakePrismaClient:
             litellm_budgetwindowspend=_FakeFindUniqueTable(row=row, error=error),
             litellm_spendlogs=_FakeSpendLogsTable(total=spend_logs_total),
             litellm_endusertable=_FakeFindUniqueTable(row=end_user_row, error=end_user_error),
+            litellm_verificationtoken=_InFlightCountingTable(),
         )
 
 
@@ -306,6 +322,21 @@ async def test_end_user_from_db_returns_none_without_a_row_a_client_or_on_db_err
     )
 
 
+@pytest.mark.asyncio
+async def test_from_db_bounds_in_flight_prisma_requests_across_counter_keys():
+    """Per-counter singleflight only collapses duplicates of one key. A cold-cache burst
+    over many distinct keys must still not flood the prisma engine HTTP pool (LIT-6435)."""
+    prisma: Final = _FakePrismaClient()
+    burst: Final = PROXY_DB_LOOKUP_MAX_CONCURRENCY * 5
+
+    results: Final = await asyncio.gather(
+        *(SpendCounterReseed.from_db(prisma_client=prisma, counter_key=f"spend:key:hashed-{i}") for i in range(burst))
+    )
+
+    assert results == [1.0] * burst
+    assert prisma.db.litellm_verificationtoken.max_in_flight == PROXY_DB_LOOKUP_MAX_CONCURRENCY
+
+
 @pytest.mark.asyncio
 async def test_from_db_still_never_reads_the_end_user_row():
     """A cold end-user counter keeps seeding from the cached end-user object the auth
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/openai/test_moderations.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/openai/test_moderations.py
index 2b43720a126..615d06b0f42 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/openai/test_moderations.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/openai/test_moderations.py
@@ -3,14 +3,19 @@
 Test OpenAI Moderation Guardrail
 """
 
+import json
 import os
+from typing import Final
 
 
 from unittest.mock import MagicMock, patch
 
+import httpx
 import pytest
 
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
 from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy.common_utils.callback_utils import get_logging_caching_headers
 from litellm.proxy.guardrails.guardrail_hooks.openai.moderations import (
     OpenAIModerationGuardrail,
 )
@@ -989,3 +994,30 @@ async def test_openai_moderation_initialize_guardrail_forwards_streaming_flags()
             assert guardrail.streaming_sampling_rate == 2
     finally:
         litellm.logging_callback_manager._reset_all_callbacks()
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(("input_type", "stage"), [("request", "pre_call"), ("response", "post_call")])
+async def test_openai_moderation_records_moderation_id_as_scan_metadata(input_type: str, stage: str):
+    """Each moderation call's id is exposed with the guardrail name, stage and provider that produced it."""
+    payload: Final = {
+        "id": f"modr-{stage}",
+        "model": "omni-moderation-latest",
+        "results": [{"flagged": False, "categories": {}, "category_scores": {}, "category_applied_input_types": {}}],
+    }
+    http_client: Final = AsyncHTTPHandler()
+    http_client.client = httpx.AsyncClient(transport=httpx.MockTransport(lambda _: httpx.Response(200, json=payload)))
+
+    with patch.dict(os.environ, {"OPENAI_API_KEY": "test-key"}):
+        guardrail: Final = OpenAIModerationGuardrail(guardrail_name="openai-mod")
+    guardrail.async_handler = http_client
+    request_data: Final[dict[str, object]] = {"metadata": {}}
+
+    await guardrail.apply_guardrail(inputs={"texts": ["hello"]}, request_data=request_data, input_type=input_type)
+
+    headers: Final = get_logging_caching_headers(request_data)
+    assert headers is not None
+    assert headers["x-litellm-guardrail-scan-id"] == f"modr-{stage}"
+    assert json.loads(headers["x-litellm-guardrail-scan-metadata"]) == [
+        {"guardrail": "openai-mod", "stage": stage, "provider": "openai_moderation", "scan_id": f"modr-{stage}"}
+    ]
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_guardrails.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_guardrails.py
index 7da55f22bda..c0762edec92 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_guardrails.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_guardrails.py
@@ -3,6 +3,8 @@ Unit tests for Bedrock Guardrails
 """
 
 import json
+import asyncio
+from datetime import datetime, timezone
 import sys
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -28,6 +30,7 @@ from litellm.types.proxy.guardrails.guardrail_hooks.bedrock_guardrails import (
     BedrockTextContent,
 )
 from litellm.types.utils import CallTypes, ModelResponse
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 
 @pytest.mark.asyncio
@@ -5842,3 +5845,36 @@ async def test_bearer_token_never_runs_the_sigv4_credential_chain(monkeypatch):
 
     assert response["action"] == "NONE"
     assert mock_post.call_args.kwargs["headers"]["Authorization"] == "Bearer env-bearer-token-12345"
+
+
+@pytest.mark.asyncio
+async def test_apply_guardrail_signs_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: the ApplyGuardrail request is signed with SigV4, and botocore
+    refreshes expiring credentials inside that signing with a blocking HTTP call, so it must run
+    on a worker thread to keep the loop serving other requests."""
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    guardrail = BedrockGuardrail(guardrailIdentifier="test-guardrail", guardrailVersion="DRAFT")
+    probe = EventLoopProbe()
+    allowed = httpx.Response(
+        200,
+        json={"action": "NONE", "outputs": [], "assessments": []},
+        request=httpx.Request("POST", "https://bedrock-runtime.us-east-1.amazonaws.com"),
+    )
+
+    with patch.object(guardrail.async_handler, "post", new=AsyncMock(return_value=allowed)):
+        release = asyncio.create_task(probe.release_refresh_from_the_loop())
+        response = await guardrail._post_apply_guardrail_content(
+            content=[{"text": {"text": "hello"}}],
+            base_request_data={"source": "INPUT"},
+            credentials=probe.credentials(),
+            aws_region_name="us-east-1",
+            api_key=None,
+            request_data={},
+            event_type=GuardrailEventHooks.pre_call,
+            start_time=datetime.now(timezone.utc),
+            completed_chunk_usages=[],
+        )
+        await release
+
+    assert response["action"] == "NONE"
+    assert probe.served_during_refresh is True
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_invoke_guardrail_checks.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_invoke_guardrail_checks.py
index f4af77d2e40..bbc8fd539a3 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_invoke_guardrail_checks.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_bedrock_invoke_guardrail_checks.py
@@ -5,10 +5,12 @@ All Bedrock HTTP calls are mocked; no real AWS calls are made.
 """
 
 import json
+import asyncio
 import logging
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
+import httpx
 from fastapi import HTTPException
 
 
@@ -21,6 +23,7 @@ from litellm.types.proxy.guardrails.guardrail_hooks.bedrock_guardrails import (
     BedrockGuardrailResponse,
 )
 from litellm.types.utils import Choices, Message, ModelResponse
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 
 CONTENT_FILTER_CHECKS = {"contentFilter": {"categories": [{"category": "VIOLENCE"}]}}
 
@@ -861,3 +864,33 @@ async def test_checks_bearer_token_never_runs_the_sigv4_credential_chain(monkeyp
         {"check": "contentFilter", "category": "VIOLENCE", "severityScore": 0.8}
     ]
     assert post.call_args.kwargs["headers"]["Authorization"] == "Bearer env-bearer-token-12345"
+
+
+@pytest.mark.asyncio
+async def test_invoke_guardrail_checks_signs_off_the_event_loop(monkeypatch):
+    """Regression for issue #40165: the checks request is signed with SigV4, and botocore refreshes
+    expiring credentials inside that signing with a blocking HTTP call, so it must run on a worker
+    thread to keep the loop serving other requests."""
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    g = BedrockGuardrail(checks=CONTENT_FILTER_CHECKS, content_filter_threshold=0.5)
+    probe = EventLoopProbe()
+    allowed = httpx.Response(
+        200,
+        json={"results": {"contentFilter": {"results": [{"category": "VIOLENCE", "severityScore": 0.1}]}}},
+        request=httpx.Request("POST", "https://bedrock-runtime.us-east-1.amazonaws.com"),
+    )
+
+    with (
+        patch.object(g, "_load_credentials", return_value=(probe.credentials(), "us-east-1")),
+        patch.object(g.async_handler, "post", new=AsyncMock(return_value=allowed)),
+    ):
+        release = asyncio.create_task(probe.release_refresh_from_the_loop())
+        response = await g.make_bedrock_api_request(
+            source="INPUT",
+            messages=[{"role": "user", "content": "hello"}],
+            request_data={"messages": []},
+        )
+        await release
+
+    assert response == BedrockGuardrailResponse()
+    assert probe.served_during_refresh is True
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_panw_prisma_airs.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_panw_prisma_airs.py
index 8f29ba66814..3d7c6e06d94 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_panw_prisma_airs.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_panw_prisma_airs.py
@@ -12,6 +12,7 @@ This test file follows LiteLLM's testing patterns and covers:
 import copy
 import json
 from datetime import datetime
+from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import httpx
@@ -5785,7 +5786,14 @@ class TestPanwAirsScanIdExposure:
 
         headers = get_logging_caching_headers(data)
         assert headers["x-litellm-guardrail-scan-id"] == "scan-abc-123"
-        assert "x-litellm-guardrail-scan-metadata" not in headers
+        assert json.loads(headers["x-litellm-guardrail-scan-metadata"]) == [
+            {
+                "guardrail": handler.guardrail_name,
+                "stage": "pre_call",
+                "provider": "panw_prisma_airs",
+                "scan_id": "scan-abc-123",
+            }
+        ]
 
     @pytest.mark.asyncio
     async def test_request_and_response_scan_ids_are_both_exposed(self, user_api_key_dict):
@@ -5809,6 +5817,26 @@ class TestPanwAirsScanIdExposure:
 
         headers = get_logging_caching_headers(data)
         assert headers["x-litellm-guardrail-scan-id"] == "scan-abc-123,scan-response-456"
+        assert [(e["stage"], e["scan_id"]) for e in json.loads(headers["x-litellm-guardrail-scan-metadata"])] == [
+            ("pre_call", "scan-abc-123"),
+            ("post_call", "scan-response-456"),
+        ]
+
+    @pytest.mark.asyncio
+    async def test_apply_guardrail_response_scan_is_tagged_post_call(self):
+        from litellm.proxy.common_utils.callback_utils import get_logging_caching_headers
+
+        handler: Final = self._handler(self.ALLOW_SCAN_RESULT)
+        request_data: Final[dict[str, object]] = {"litellm_call_id": "test-call-id", "model": "gpt-4", "metadata": {}}
+
+        await handler.apply_guardrail(
+            inputs={"texts": ["Hello world"]}, request_data=request_data, input_type="response"
+        )
+
+        headers: Final = get_logging_caching_headers(request_data)
+        assert headers is not None
+        entries: Final = json.loads(headers["x-litellm-guardrail-scan-metadata"])
+        assert [(e["stage"], e["provider"]) for e in entries] == [("post_call", "panw_prisma_airs")]
 
     @pytest.mark.asyncio
     async def test_repeated_scan_id_is_not_duplicated(self, user_api_key_dict):
@@ -5850,6 +5878,8 @@ class TestPanwAirsScanIdExposure:
 
         assert "guardrail_scan_ids" in _UNTRUSTED_METADATA_CONTROL_FIELDS
         assert "guardrail_scan_ids" in _UNTRUSTED_ROOT_CONTROL_FIELDS
+        assert "guardrail_scan_metadata" in _UNTRUSTED_METADATA_CONTROL_FIELDS
+        assert "guardrail_scan_metadata" in _UNTRUSTED_ROOT_CONTROL_FIELDS
 class TestPanwAirsBlockedErrorDetailPassthrough:
     """Regression tests for the full AIRS scan response on blocks.
 
diff --git a/tests/test_litellm/proxy/guardrails/test_auto_router_compression.py b/tests/test_litellm/proxy/guardrails/test_auto_router_compression.py
index db2f94306fb..0d723d6671f 100644
--- a/tests/test_litellm/proxy/guardrails/test_auto_router_compression.py
+++ b/tests/test_litellm/proxy/guardrails/test_auto_router_compression.py
@@ -56,13 +56,13 @@ class TestPolicyFromLitellmParams:
 
 
 class _FakeRouter:
-    """Minimal stand-in for litellm.Router.get_model_list, for policy_for_model."""
+    """Minimal stand-in for litellm.Router.deployments_for_request, for policy_for_model."""
 
     def __init__(self, deployments: list[dict[str, Any]]):
         self._deployments = deployments
 
-    def get_model_list(self, model_name, team_id=None):
-        return [d for d in self._deployments if d.get("model_name") == model_name]
+    def deployments_for_request(self, model, request_kwargs):
+        return [d for d in self._deployments if d.get("model_name") == model]
 
 
 def _marker(compression: dict[str, str], tags: list[str] | None = None) -> dict[str, Any]:
@@ -78,23 +78,23 @@ def _marker(compression: dict[str, str], tags: list[str] | None = None) -> dict[
 
 class TestPolicyForModel:
     def test_no_router_returns_none(self):
-        assert policy_for_model(llm_router=None, model_alias="smart-router", team_id=None, request_tags=()) is None
+        assert policy_for_model(llm_router=None, model_alias="smart-router", request_kwargs={}, request_tags=()) is None
 
     def test_no_marker_deployment_returns_none(self):
         router = _FakeRouter([{"model_name": "smart-router", "litellm_params": {"model": "openai/gpt-4o-mini"}}])
-        assert policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=()) is None
+        assert policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=()) is None
 
     def test_marker_deployment_without_policy_returns_none(self):
         router = _FakeRouter(
             [{"model_name": "smart-router", "litellm_params": {"model": "auto_router/complexity_router"}}]
         )
-        assert policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=()) is None
+        assert policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=()) is None
 
     def test_marker_deployment_with_policy_is_found(self):
         router = _FakeRouter(
             [_marker({"auto_router_routing_compression": "headroom-a", "auto_router_model_compression": "none"})]
         )
-        policy = policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=())
+        policy = policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=())
         assert policy == AutoRouterCompressionPolicy(routing="headroom-a", model=None)
 
     def test_picks_the_marker_whose_tags_the_request_carries(self):
@@ -107,8 +107,8 @@ class TestPolicyForModel:
             ]
         )
 
-        eu = policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=("eu",))
-        us = policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=("us",))
+        eu = policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=("eu",))
+        us = policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=("us",))
 
         assert eu == AutoRouterCompressionPolicy(routing="headroom-eu", model=None)
         assert us == AutoRouterCompressionPolicy(routing="headroom-us", model=None)
@@ -116,7 +116,7 @@ class TestPolicyForModel:
     def test_untagged_marker_matches_any_request(self):
         router = _FakeRouter([_marker({"auto_router_routing_compression": "headroom-a"})])
         policy = policy_for_model(
-            llm_router=router, model_alias="smart-router", team_id=None, request_tags=("anything",)
+            llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=("anything",)
         )
         assert policy == AutoRouterCompressionPolicy(routing="headroom-a", model=None)
 
@@ -128,14 +128,14 @@ class TestPolicyForModel:
                 _marker({"auto_router_routing_compression": "headroom-default"}),
             ]
         )
-        policy = policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=("us",))
+        policy = policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=("us",))
         assert policy == AutoRouterCompressionPolicy(routing="headroom-default", model=None)
 
     def test_no_untagged_fallback_means_no_policy(self):
         """No matching marker means no policy, not an unrelated slice's compression."""
         router = _FakeRouter([_marker({"auto_router_routing_compression": "headroom-eu"}, tags=["eu"])])
         assert (
-            policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=("us",)) is None
+            policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=("us",)) is None
         )
 
     def test_tag_scoped_marker_takes_precedence_over_untagged(self):
@@ -147,7 +147,7 @@ class TestPolicyForModel:
                 _marker({"auto_router_routing_compression": "headroom-eu"}, tags=["eu"]),
             ]
         )
-        policy = policy_for_model(llm_router=router, model_alias="smart-router", team_id=None, request_tags=("eu",))
+        policy = policy_for_model(llm_router=router, model_alias="smart-router", request_kwargs={}, request_tags=("eu",))
         assert policy == AutoRouterCompressionPolicy(routing="headroom-eu", model=None)
 
 
diff --git a/tests/test_litellm/proxy/health_endpoints/test_health_endpoints.py b/tests/test_litellm/proxy/health_endpoints/test_health_endpoints.py
index e9e58347337..527d46931fe 100644
--- a/tests/test_litellm/proxy/health_endpoints/test_health_endpoints.py
+++ b/tests/test_litellm/proxy/health_endpoints/test_health_endpoints.py
@@ -1058,6 +1058,35 @@ async def test_health_services_endpoint_galileo(status, error_message):
         mock_instance.async_health_check.assert_awaited_once()
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "status,error_message",
+    [
+        ("healthy", ""),
+        ("unhealthy", "PointFive authentication failed"),
+    ],
+)
+async def test_health_services_endpoint_pointfive(monkeypatch, status, error_message):
+    import litellm.integrations.pointfive as pointfive_package
+
+    mock_instance = MagicMock()
+    mock_instance.async_health_check = AsyncMock(return_value={"status": status, "error_message": error_message})
+    logger_class = MagicMock(return_value=mock_instance)
+    monkeypatch.setattr(pointfive_package, "PointFiveLogger", logger_class)
+
+    result = await health_services_endpoint(user_api_key_dict=_pointfive_admin(), service="pointfive")
+
+    if status == "healthy":
+        assert result["status"] == "healthy"
+        assert result["message"] == "PointFive is healthy"
+    else:
+        assert result["status"] == "unhealthy"
+        assert result["message"] == error_message
+    mock_instance.async_health_check.assert_awaited_once()
+    # A check that left the periodic flush running would leak a flusher per press of the ui test button.
+    logger_class.assert_called_once_with(start_periodic_flush=False)
+
+
 @pytest.mark.asyncio
 async def test_health_services_endpoint_datadog_llm_observability():
     """
@@ -1301,6 +1330,33 @@ def test_health_readiness_details_returns_diagnostic_fields(monkeypatch):
     assert "cache" in response_data
 
 
+@pytest.mark.parametrize(
+    "general_settings, expected_warning",
+    [
+        ({}, True),
+        ({"disable_env_credential_login": True}, False),
+    ],
+)
+def test_health_readiness_details_reports_env_credential_login_warning(monkeypatch, general_settings, expected_warning):
+    """
+    The Admin UI banner is driven by this flag: it must be True while
+    env-credential login is possible and False once
+    `disable_env_credential_login` turns that login path off.
+    """
+    app = FastAPI()
+    app.include_router(_health_endpoints_module.router)
+    app.dependency_overrides[user_api_key_auth] = lambda: UserAPIKeyAuth(user_role=LitellmUserRoles.PROXY_ADMIN)
+    client = TestClient(app)
+
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", None)
+    monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", general_settings)
+
+    response = client.get("/health/readiness/details")
+
+    assert response.status_code == 200, response.text
+    assert response.json()["show_env_credential_login_warning"] is expected_warning
+
+
 def test_health_readiness_allows_explicit_legacy_public_details(monkeypatch):
     """
     Operators can explicitly preserve the legacy public readiness payload.
@@ -3104,3 +3160,60 @@ def test_test_model_connection_accepts_image_edit_mode(monkeypatch):
 
     assert response.status_code == 200, response.text
     assert response.json()["status"] == "success"
+
+
+def _pointfive_admin() -> UserAPIKeyAuth:
+    return UserAPIKeyAuth(token="admin-token", user_id="admin-user", user_role=LitellmUserRoles.PROXY_ADMIN)
+
+
+@pytest.mark.asyncio
+async def test_health_services_endpoint_pointfive_without_a_key_is_unhealthy_not_a_server_error(monkeypatch):
+    """
+    The logger refuses to start without an api key.
+
+    That refusal is the answer the operator asked for, so it has to come back as an
+    unhealthy result rather than a 500 from the endpoint.
+    """
+    import litellm.integrations.pointfive as pointfive_package
+
+    def refuse(**_):
+        raise ValueError("pointfive logging requires an api key. Set POINTFIVE_API_KEY")
+
+    monkeypatch.setattr(pointfive_package, "PointFiveLogger", refuse)
+
+    result = await health_services_endpoint(user_api_key_dict=_pointfive_admin(), service="pointfive")
+
+    assert result["status"] == "unhealthy"
+    assert "requires an api key" in result["message"]
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "role",
+    [
+        LitellmUserRoles.INTERNAL_USER,
+        LitellmUserRoles.INTERNAL_USER_VIEW_ONLY,
+        LitellmUserRoles.TEAM,
+        LitellmUserRoles.CUSTOMER,
+    ],
+)
+async def test_health_services_endpoint_pointfive_blocks_non_admin(monkeypatch, role):
+    """
+    The ping travels on the proxy-wide PointFive credential and stamps liveness at PointFive.
+
+    A tenant key must not be able to keep an integration looking alive, or read back
+    account-level authentication failures through it.
+    """
+    import litellm.integrations.pointfive as pointfive_package
+    from litellm.proxy._types import ProxyException
+
+    logger_class = MagicMock()
+    monkeypatch.setattr(pointfive_package, "PointFiveLogger", logger_class)
+
+    with pytest.raises(ProxyException) as raised:
+        await health_services_endpoint(
+            user_api_key_dict=UserAPIKeyAuth(token="t", user_id="u", user_role=role), service="pointfive"
+        )
+
+    assert str(raised.value.code) == "403"
+    logger_class.assert_not_called()
diff --git a/tests/test_litellm/proxy/hooks/test_batch_enqueued_tokens.py b/tests/test_litellm/proxy/hooks/test_batch_enqueued_tokens.py
index edc921a40a3..e3e39a87009 100644
--- a/tests/test_litellm/proxy/hooks/test_batch_enqueued_tokens.py
+++ b/tests/test_litellm/proxy/hooks/test_batch_enqueued_tokens.py
@@ -7,6 +7,7 @@ response-shape helpers the v3 limiter's post-call hooks rely on.
 """
 
 import base64
+import logging
 import socket
 import uuid
 from collections.abc import Mapping, Sequence
@@ -16,6 +17,7 @@ from typing import Final
 import pytest
 
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 from litellm.constants import BATCH_ENQUEUED_TOKEN_TTL_SECONDS
 from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.hooks.batch_enqueued_tokens import (
@@ -439,3 +441,29 @@ async def test_redis_lua_path_full_lifecycle():
     refill = await store.reserve(tokens=50, scopes=(key_scope, team_scope))
     assert isinstance(refill, BatchEnqueuedTokenReservation)
     await store.refund(refill)
+
+
+class _OpenBreakerRedis:
+    def async_register_script(self, script: str):
+        async def refused(keys: Sequence[str], args: Sequence[str | bytes | int | float]) -> object:
+            raise RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+
+        return refused
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_keeps_reservations_in_memory_without_a_warning(caplog):
+    scope = _scope(limit=100)
+    store = BatchEnqueuedTokenStore(
+        internal_usage_cache=InternalUsageCache(DualCache(redis_cache=_OpenBreakerRedis(), default_in_memory_ttl=60))  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    )
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Proxy"):
+        reservation = await store.reserve(tokens=60, scopes=(scope,))
+        assert isinstance(reservation, BatchEnqueuedTokenReservation)
+        assert reservation.backend == "memory"
+        await store.save_reservation("batch_quiet", reservation)
+        assert await store.pop_reservation("batch_quiet") == reservation
+
+    assert not [record for record in caplog.records if record.levelno >= logging.WARNING]
+    assert sum("circuit breaker is open" in record.getMessage() for record in caplog.records) == 3
diff --git a/tests/test_litellm/proxy/hooks/test_dynamic_rate_limiter_v3.py b/tests/test_litellm/proxy/hooks/test_dynamic_rate_limiter_v3.py
index 0ff8b67b1a7..527449bbc48 100644
--- a/tests/test_litellm/proxy/hooks/test_dynamic_rate_limiter_v3.py
+++ b/tests/test_litellm/proxy/hooks/test_dynamic_rate_limiter_v3.py
@@ -1861,3 +1861,87 @@ async def test_tpm_only_model_enforces_priority_and_model_capacity(monkeypatch):
         )
     assert capacity_blocked.value.status_code == 429
     assert "Model capacity reached" in capacity_blocked.value.detail["error"]
+
+
+@pytest.mark.asyncio
+async def test_post_call_success_hook_attaches_priority_headers_to_dict_response():
+    from litellm.proxy.hooks.parallel_request_limiter_v3 import (
+        RateLimitResponse,
+        RateLimitStatus,
+        get_or_create_request_stash,
+    )
+
+    handler = DynamicRateLimitHandler(internal_usage_cache=DualCache())
+    get_or_create_request_stash().rate_limit_response = RateLimitResponse(
+        overall_code="OK",
+        statuses=[
+            RateLimitStatus(
+                code="OK",
+                current_limit=75,
+                limit_remaining=74,
+                rate_limit_type="requests",
+                descriptor_key="priority_model",
+            )
+        ],
+    )
+    response = {
+        "id": "msg_123",
+        "type": "message",
+        "role": "assistant",
+        "content": [],
+        "_hidden_params": {"additional_headers": {"x-litellm-attempted-retries": 0}},
+    }
+
+    await handler.async_post_call_success_hook(
+        data={"model": "anthropic-haiku"},
+        user_api_key_dict=UserAPIKeyAuth(metadata={"priority": "premium"}),
+        response=response,
+    )
+
+    additional_headers = response["_hidden_params"]["additional_headers"]
+    assert additional_headers["x-litellm-attempted-retries"] == 0
+    assert additional_headers["x-ratelimit-priority_model-limit-requests"] == 75
+    assert additional_headers["x-ratelimit-priority_model-remaining-requests"] == 74
+    assert additional_headers["x-litellm-priority"] == "premium"
+    assert additional_headers["x-litellm-rate-limiter-version"] == "v3"
+
+
+@pytest.mark.asyncio
+async def test_post_call_success_hook_leaves_raw_provider_dict_untouched():
+    handler = DynamicRateLimitHandler(internal_usage_cache=DualCache())
+    response = {"id": "msg_123", "type": "message", "role": "assistant", "content": []}
+
+    await handler.async_post_call_success_hook(
+        data={"model": "anthropic-haiku"},
+        user_api_key_dict=UserAPIKeyAuth(metadata={"priority": "premium"}),
+        response=response,
+    )
+
+    assert response == {"id": "msg_123", "type": "message", "role": "assistant", "content": []}
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("team_metadata", "expected_priority_header"),
+    [
+        ({"priority": "优先"}, None),
+        ({"priority": "high"}, "high"),
+        ({}, "default"),
+    ],
+)
+async def test_post_call_success_hook_priority_header_is_always_http_encodable(team_metadata, expected_priority_header):
+    from starlette.responses import Response
+
+    handler = DynamicRateLimitHandler(internal_usage_cache=DualCache())
+    response = {"id": "msg_123", "type": "message", "role": "assistant", "content": [], "_hidden_params": {}}
+
+    await handler.async_post_call_success_hook(
+        data={"model": "anthropic-haiku"},
+        user_api_key_dict=UserAPIKeyAuth(team_id="team-1", team_metadata=team_metadata),
+        response=response,
+    )
+
+    additional_headers = response["_hidden_params"]["additional_headers"]
+    http_response = Response(headers={key: str(value) for key, value in additional_headers.items()})
+    assert http_response.headers.get("x-litellm-priority") == expected_priority_header
+    assert http_response.headers["x-litellm-rate-limiter-version"] == "v3"
diff --git a/tests/test_litellm/proxy/hooks/test_max_budget_per_session_limiter.py b/tests/test_litellm/proxy/hooks/test_max_budget_per_session_limiter.py
index 879e2d65c7a..a1b3f313814 100644
--- a/tests/test_litellm/proxy/hooks/test_max_budget_per_session_limiter.py
+++ b/tests/test_litellm/proxy/hooks/test_max_budget_per_session_limiter.py
@@ -10,10 +10,12 @@ Tests that session-scoped budget tracking works correctly:
 
 from unittest.mock import patch
 
+import logging
 import pytest
 from fastapi import HTTPException
 
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import _redis_circuit_breaker_guard
 from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.hooks.max_budget_per_session_limiter import (
     _PROXY_MaxBudgetPerSessionHandler,
@@ -163,3 +165,37 @@ async def test_no_agent_id_passes():
         call_type="",
     )
     assert result is None
+
+
+class _OpenBreakerRedis:
+    def __init__(self) -> None:
+        from litellm.caching.redis_cache import RedisCircuitBreaker
+
+        self._circuit_breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+        for _ in range(3):
+            self._circuit_breaker.record_failure()
+
+    @_redis_circuit_breaker_guard
+    async def async_get_cache(self, key, **kwargs):
+        raise AssertionError("never reached")
+
+    def async_register_script(self, script):
+        @_redis_circuit_breaker_guard
+        async def refused(_self, keys, args):
+            raise AssertionError("never reached")
+
+        return lambda keys, args: refused(self, keys, args)
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_reads_session_spend_locally_without_a_warning(caplog):
+    cache = DualCache(redis_cache=_OpenBreakerRedis())  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    handler = _PROXY_MaxBudgetPerSessionHandler(internal_usage_cache=InternalUsageCache(cache))
+    caplog.clear()
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Proxy"):
+        spend = await handler._get_current_spend("{session_budget:quiet}:spend")
+
+    assert spend == 0.0
+    assert [record.getMessage() for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert any("circuit breaker is open" in record.getMessage() for record in caplog.records)
diff --git a/tests/test_litellm/proxy/hooks/test_parallel_request_limiter_v3.py b/tests/test_litellm/proxy/hooks/test_parallel_request_limiter_v3.py
index 4003286d887..10c0bb88a82 100644
--- a/tests/test_litellm/proxy/hooks/test_parallel_request_limiter_v3.py
+++ b/tests/test_litellm/proxy/hooks/test_parallel_request_limiter_v3.py
@@ -6171,3 +6171,116 @@ async def test_success_hook_leaves_stash_untouched_for_non_batch_responses():
         data={}, user_api_key_dict=user, response=ModelResponse(usage=Usage(total_tokens=5))
     )
     assert get_request_stash().batch_enqueued_reservation == reservation
+
+
+@pytest.mark.asyncio
+async def test_post_call_success_hook_attaches_ratelimit_headers_to_dict_response():
+    from litellm.proxy.hooks.parallel_request_limiter_v3 import RateLimitResponse, RateLimitStatus
+
+    handler = _PROXY_MaxParallelRequestsHandler(internal_usage_cache=InternalUsageCache(DualCache()))
+    get_or_create_request_stash().rate_limit_response = RateLimitResponse(
+        overall_code="OK",
+        statuses=[
+            RateLimitStatus(
+                code="OK",
+                current_limit=100,
+                limit_remaining=99,
+                rate_limit_type="requests",
+                descriptor_key="model_saturation_check",
+            )
+        ],
+    )
+    response = {
+        "id": "msg_123",
+        "type": "message",
+        "role": "assistant",
+        "content": [],
+        "_hidden_params": {"additional_headers": {"x-litellm-attempted-retries": 0}},
+    }
+
+    await handler.async_post_call_success_hook(
+        data={"model": "anthropic-haiku"},
+        user_api_key_dict=UserAPIKeyAuth(api_key=hash_token("sk-dict-response")),
+        response=response,
+    )
+
+    additional_headers = response["_hidden_params"]["additional_headers"]
+    assert additional_headers["x-litellm-attempted-retries"] == 0
+    assert additional_headers["x-ratelimit-model_saturation_check-limit-requests"] == 100
+    assert additional_headers["x-ratelimit-model_saturation_check-remaining-requests"] == 99
+
+
+@pytest.mark.asyncio
+async def test_post_call_success_hook_leaves_raw_provider_dict_untouched():
+    from litellm.proxy.hooks.parallel_request_limiter_v3 import RateLimitResponse, RateLimitStatus
+
+    handler = _PROXY_MaxParallelRequestsHandler(internal_usage_cache=InternalUsageCache(DualCache()))
+    get_or_create_request_stash().rate_limit_response = RateLimitResponse(
+        overall_code="OK",
+        statuses=[
+            RateLimitStatus(
+                code="OK",
+                current_limit=100,
+                limit_remaining=99,
+                rate_limit_type="requests",
+                descriptor_key="model_saturation_check",
+            )
+        ],
+    )
+    response = {"id": "msg_123", "type": "message", "role": "assistant", "content": []}
+
+    await handler.async_post_call_success_hook(
+        data={"model": "anthropic-haiku"},
+        user_api_key_dict=UserAPIKeyAuth(api_key=hash_token("sk-raw-dict")),
+        response=response,
+    )
+
+    assert response == {"id": "msg_123", "type": "message", "role": "assistant", "content": []}
+
+
+class _OpenBreakerRedis:
+    def async_register_script(self, script: str):
+        async def refused(keys, args):
+            from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
+
+            raise RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+
+        return refused
+
+    async def async_increment_pipeline(self, increment_list, **kwargs):
+        from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
+
+        raise RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_falls_back_to_the_pipeline_without_a_warning(caplog):
+    from litellm.types.caching import RedisPipelineIncrementOperation
+
+    handler = _PROXY_MaxParallelRequestsHandler(
+        internal_usage_cache=InternalUsageCache(DualCache(redis_cache=_OpenBreakerRedis()))  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    )
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Proxy"):
+        await handler.async_increment_tokens_with_ttl_preservation(
+            pipeline_operations=[RedisPipelineIncrementOperation(key="quiet_key", increment_value=10.0, ttl=60)]
+        )
+
+    assert await handler.internal_usage_cache.dual_cache.async_get_cache("quiet_key") == 10.0
+    assert [record.getMessage() for record in caplog.records if record.levelno >= logging.WARNING] == []
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_reads_the_sliding_window_locally_without_a_warning(caplog):
+    handler = _PROXY_MaxParallelRequestsHandler(
+        internal_usage_cache=InternalUsageCache(DualCache(redis_cache=_OpenBreakerRedis()))  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    )
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Proxy"):
+        values = await handler._execute_redis_batch_rate_limiter_script(
+            ["{quiet}:window", "{quiet}:counter"], now_int=int(time.time())
+        )
+
+    assert isinstance(values, list)
+    assert [record.getMessage() for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert any("circuit breaker is open" in record.getMessage() for record in caplog.records)
diff --git a/tests/test_litellm/proxy/hooks/test_proxy_track_cost_callback.py b/tests/test_litellm/proxy/hooks/test_proxy_track_cost_callback.py
index eff892f2d80..c96cfc3ee4a 100644
--- a/tests/test_litellm/proxy/hooks/test_proxy_track_cost_callback.py
+++ b/tests/test_litellm/proxy/hooks/test_proxy_track_cost_callback.py
@@ -5,14 +5,20 @@ from unittest.mock import AsyncMock, MagicMock, patch
 import pytest
 
 from litellm.litellm_core_utils.internal_call_metadata import MODEL_ACCESS_GROUP_METADATA_KEY
-from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy._types import SpendLogsPayload, UserAPIKeyAuth
+from litellm.proxy.collector import SpendEventConsumer
+from litellm.proxy.db.spend_log_tool_index import response_tool_call_names
 from litellm.proxy.hooks.proxy_track_cost_callback import (
     _get_budget_reservation_from_metadata,
     _ProxyDBLogger,
     _should_track_cost_callback,
     _update_database_and_spend_counters,
+    run_spend_event,
 )
-from litellm.types.utils import CallTypes, Usage
+from litellm.proxy.spend_tracking.spend_event import SpendEventDecodeError, build_spend_event, decode_spend_event
+from litellm.proxy.spend_tracking.spend_event_producer import SpendEventProducer, UnixAddress
+from litellm.proxy.spend_tracking.spend_tracking_utils import get_logging_payload
+from litellm.types.utils import CallTypes, LiteLLMBatch, ModelResponse, Usage
 
 
 @pytest.mark.asyncio
@@ -2096,3 +2102,248 @@ async def test_spend_counters_keep_every_granted_group_when_the_deployment_is_un
     )
 
     assert charged == ("premium", "tier0")
+
+
+def _offload_kwargs() -> dict:
+    big_prompt = "x" * 10_000
+    reservation = {"reserved_cost": 0.5, "entries": [{"counter_key": "key:hash-1", "reserved_cost": 0.5}]}
+    return {
+        "litellm_call_id": "call-1",
+        "call_type": "acompletion",
+        "model": "gpt-4o",
+        "custom_llm_provider": "openai",
+        "stream": False,
+        "cache_hit": None,
+        "response_cost": 0.0125,
+        "completion_start_time": datetime(2026, 1, 1, 0, 0, 1),
+        "messages": [{"role": "user", "content": big_prompt}],
+        "tools": [{"type": "function", "function": {"name": "get_weather", "parameters": {"type": "object"}}}],
+        "litellm_params": {
+            "api_base": "https://api.openai.com",
+            "preset_cache_key": None,
+            "proxy_server_request": {"body": {"messages": [{"role": "user", "content": big_prompt}]}},
+            "metadata": {
+                "user_api_key": "hash-1",
+                "user_api_key_hash": "hash-1",
+                "user_api_key_alias": "alias-1",
+                "user_api_key_user_id": "user-1",
+                "user_api_key_team_id": "team-1",
+                "user_api_key_org_id": "org-1",
+                "user_api_key_end_user_id": "end-user-1",
+                "user_api_key_auth": UserAPIKeyAuth(api_key="hash-1", budget_reservation=reservation),
+                "model_group": "gpt-4o",
+                "model_info": {"id": "deployment-1"},
+                "tags": ["tag-a"],
+            },
+        },
+        "standard_logging_object": {
+            "id": "chatcmpl-1",
+            "trace_id": "trace-1",
+            "response_cost": 0.0125,
+            "model": "gpt-4o-2024-08-06",
+            "model_id": "deployment-1",
+            "model_group": "gpt-4o",
+            "api_base": "https://api.openai.com",
+            "custom_llm_provider": "openai",
+            "prompt_tokens": 5000,
+            "completion_tokens": 4000,
+            "total_tokens": 9000,
+            "request_tags": ["tag-a"],
+            "request_model_access_groups": ["premium"],
+            "messages": [{"role": "user", "content": big_prompt}],
+            "response": {"choices": [{"message": {"content": "y" * 10_000}}]},
+            "model_parameters": {"temperature": 0.1},
+            "metadata": {
+                "user_api_key_hash": "hash-1",
+                "user_api_key_end_user_id": "end-user-1",
+                "usage_object": {"prompt_tokens": 5000, "completion_tokens": 4000, "total_tokens": 9000},
+            },
+            "hidden_params": {"litellm_overhead_time_ms": 3},
+            "model_map_information": {},
+            "cost_breakdown": {"input_cost": 0.0125, "output_cost": 0.0},
+        },
+    }
+
+
+def _offload_response() -> ModelResponse:
+    return ModelResponse(
+        id="chatcmpl-1",
+        model="gpt-4o-2024-08-06",
+        choices=[
+            {
+                "index": 0,
+                "message": {
+                    "role": "assistant",
+                    "content": None,
+                    "tool_calls": [
+                        {"id": "call-1", "type": "function", "function": {"name": "get_weather", "arguments": "{}"}}
+                    ],
+                },
+                "finish_reason": "tool_calls",
+            }
+        ],
+        usage=Usage(prompt_tokens=5000, completion_tokens=4000, total_tokens=9000),
+    )
+
+
+class _RecordingHandler:
+    def __init__(self) -> None:
+        self.lines: list[bytes] = []  # mutable-ok: test double records the events the sidecar received
+
+    async def __call__(self, line: bytes) -> None:
+        self.lines.append(line)
+
+
+async def _no_fallback(line: bytes) -> None:
+    raise AssertionError("the sidecar was reachable, nothing should fall back")
+
+
+@pytest.mark.asyncio
+async def test_async_log_success_event_hands_the_sidecar_a_compact_event_and_skips_the_pipeline(tmp_path):
+    handler = _RecordingHandler()
+    consumer = SpendEventConsumer(handler)
+    address = UnixAddress(path=str(tmp_path / "spend.sock"))
+    server = await consumer.serve(address)
+    producer = SpendEventProducer(
+        address=address, on_unavailable="fallback", buffer_size=10, connect_timeout=1.0, fallback=_no_fallback
+    )
+    logger = _ProxyDBLogger(producer)
+
+    with (
+        patch(  # test-quality-ok: the callback imports this from proxy_server inside its body, so there is no injection seam
+            "litellm.proxy.proxy_server.proxy_logging_obj"
+        ) as mock_proxy_logging,
+        patch(  # test-quality-ok: same function-body import, no injection seam
+            "litellm.proxy.proxy_server.increment_spend_counters", new_callable=AsyncMock
+        ) as counters,
+    ):
+        mock_proxy_logging.db_spend_update_writer.update_database = AsyncMock()
+        await logger.async_log_success_event(_offload_kwargs(), _offload_response(), datetime.now(), datetime.now())
+        await producer.close(drain_timeout=5.0)
+        server.close()
+        assert await consumer.drain(timeout=5.0) == 0
+
+    mock_proxy_logging.db_spend_update_writer.update_database.assert_not_awaited()
+    counters.assert_not_awaited()
+    assert producer.stats().sent == 1
+    assert len(handler.lines) == 1
+    assert len(handler.lines[0]) < 4_000
+    event = decode_spend_event(handler.lines[0])
+    assert not isinstance(event, SpendEventDecodeError)
+    assert event.litellm_params["metadata"]["user_api_key_team_id"] == "team-1"
+    assert event.response_cost == 0.0125
+
+
+@pytest.mark.asyncio
+async def test_async_log_success_event_keeps_batch_retrieves_in_process():
+    producer = SpendEventProducer(
+        address=UnixAddress(path="/nonexistent/spend.sock"),
+        on_unavailable="drop",
+        buffer_size=10,
+        connect_timeout=1.0,
+        fallback=_no_fallback,
+    )
+    logger = _ProxyDBLogger(producer)
+    kwargs = {**_offload_kwargs(), "call_type": CallTypes.aretrieve_batch.value}
+    completed_batch = LiteLLMBatch(
+        id="batch_abc",
+        completion_window="24h",
+        created_at=1,
+        endpoint="/v1/chat/completions",
+        input_file_id="file-in",
+        output_file_id="file-out",
+        object="batch",
+        status="completed",
+    )
+
+    with (
+        patch(  # test-quality-ok: the callback imports this from proxy_server inside its body, so there is no injection seam
+            "litellm.proxy.proxy_server.proxy_logging_obj"
+        ) as mock_proxy_logging,
+        patch(  # test-quality-ok: same function-body import, no injection seam
+            "litellm.proxy.proxy_server.increment_spend_counters", new_callable=AsyncMock
+        ),
+        patch(  # test-quality-ok: same function-body import, no injection seam
+            "litellm.proxy.proxy_server.update_cache", new_callable=AsyncMock
+        ),
+    ):
+        mock_proxy_logging.db_spend_update_writer.update_database = AsyncMock(return_value=True)
+        mock_proxy_logging.slack_alerting_instance.customer_spend_alert = AsyncMock()
+        await logger.async_log_success_event(kwargs, completed_batch, datetime.now(), datetime.now())
+
+    mock_proxy_logging.db_spend_update_writer.update_database.assert_awaited_once()
+    assert producer.stats().queued == 0
+
+
+async def _spend_row_written_by(run) -> tuple[SpendLogsPayload, dict, tuple[str, ...]]:
+    with (
+        patch(  # test-quality-ok: the callback imports this from proxy_server inside its body, so there is no injection seam
+            "litellm.proxy.proxy_server.proxy_logging_obj"
+        ) as mock_proxy_logging,
+        patch(  # test-quality-ok: same function-body import, no injection seam
+            "litellm.proxy.proxy_server.increment_spend_counters", new_callable=AsyncMock
+        ) as counters,
+        patch(  # test-quality-ok: same function-body import, no injection seam
+            "litellm.proxy.proxy_server.update_cache", new_callable=AsyncMock
+        ),
+    ):
+        mock_proxy_logging.db_spend_update_writer.update_database = AsyncMock(return_value=True)
+        mock_proxy_logging.slack_alerting_instance.customer_spend_alert = AsyncMock()
+        await run()
+        mock_proxy_logging.db_spend_update_writer.update_database.assert_awaited_once()
+        written = mock_proxy_logging.db_spend_update_writer.update_database.await_args.kwargs
+        counters.assert_awaited_once()
+        counted = dict(counters.await_args.kwargs)
+
+    row = get_logging_payload(
+        kwargs=written["kwargs"],
+        response_obj=written["completion_response"],
+        start_time=written["start_time"],
+        end_time=written["end_time"],
+    )
+    return row, counted, response_tool_call_names(written["completion_response"])
+
+
+@pytest.mark.asyncio
+async def test_sidecar_writes_the_same_spend_row_and_counters_as_the_in_process_path():
+    start_time = datetime(2026, 1, 1, 0, 0, 0)
+    end_time = datetime(2026, 1, 1, 0, 0, 2)
+
+    async def in_process() -> None:
+        await _ProxyDBLogger().async_log_success_event(_offload_kwargs(), _offload_response(), start_time, end_time)
+
+    async def via_sidecar() -> None:
+        line = build_spend_event(_offload_kwargs(), _offload_response(), start_time, end_time, store_bodies=False)
+        assert isinstance(line, bytes)
+        await run_spend_event(line)
+
+    in_process_row, in_process_counters, in_process_tools = await _spend_row_written_by(in_process)
+    sidecar_row, sidecar_counters, sidecar_tools = await _spend_row_written_by(via_sidecar)
+
+    assert sidecar_row == in_process_row
+    assert in_process_row["spend"] == 0.0125
+    assert in_process_row["team_id"] == "team-1"
+    assert in_process_row["end_user"] == "end-user-1"
+    assert in_process_row["total_tokens"] == 9000
+    assert in_process_row["model_id"] == "deployment-1"
+    assert in_process_row["request_tags"] == '["tag-a"]'
+    assert in_process_row["messages"] == "{}"
+    assert in_process_row["response"] == "{}"
+    assert sidecar_counters == in_process_counters
+    assert in_process_counters["token"] == "hash-1"
+    assert in_process_counters["response_cost"] == 0.0125
+    assert in_process_counters["budget_reservation"]["reserved_cost"] == 0.5
+    assert in_process_counters["model_access_groups"] == ("premium",)
+    assert sidecar_tools == in_process_tools == ("get_weather",)
+
+
+@pytest.mark.asyncio
+async def test_sidecar_ignores_an_undecodable_event():  # test-quality-ok: a discarded event has no observable output other than the DB writer never being reached
+    with (
+        patch(  # test-quality-ok: the callback imports this from proxy_server inside its body, so there is no injection seam
+            "litellm.proxy.proxy_server.proxy_logging_obj"
+        ) as mock_proxy_logging
+    ):
+        mock_proxy_logging.db_spend_update_writer.update_database = AsyncMock()
+        await run_spend_event(b"garbage\n")
+    mock_proxy_logging.db_spend_update_writer.update_database.assert_not_awaited()
diff --git a/tests/test_litellm/proxy/hooks/test_sensitive_data_routing.py b/tests/test_litellm/proxy/hooks/test_sensitive_data_routing.py
index 35c0f8deaf1..463d3c7ef5e 100644
--- a/tests/test_litellm/proxy/hooks/test_sensitive_data_routing.py
+++ b/tests/test_litellm/proxy/hooks/test_sensitive_data_routing.py
@@ -6,6 +6,7 @@ This feature allows guardrails to route requests to a different model
 All subsequent requests in the same session are routed to the same model.
 """
 
+import logging
 import asyncio
 from typing import Any, Dict, Optional
 from unittest.mock import AsyncMock, MagicMock, patch
@@ -13,12 +14,14 @@ from unittest.mock import AsyncMock, MagicMock, patch
 import pytest
 
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import _redis_circuit_breaker_guard
 from litellm.exceptions import SensitiveDataRouteException
 from litellm.integrations.custom_guardrail import (
     CustomGuardrail,
     get_session_id_from_request_data,
 )
 from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy.utils import InternalUsageCache
 from litellm.proxy.hooks.sensitive_data_routing import (
     _PROXY_SensitiveDataRoutingHandler,
     SENSITIVE_ROUTING_CACHE_PREFIX,
@@ -1034,3 +1037,35 @@ class TestPreCallHookDeferredRouting:
         metrics_kwargs = prom._record_guardrail_metrics.call_args.kwargs
         assert metrics_kwargs["status"] == "intervened"
         assert metrics_kwargs["error_type"] is None
+
+
+class _OpenBreakerRedis:
+    def __init__(self) -> None:
+        from litellm.caching.redis_cache import RedisCircuitBreaker
+
+        self._circuit_breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+        for _ in range(3):
+            self._circuit_breaker.record_failure()
+
+    @_redis_circuit_breaker_guard
+    async def async_get_cache(self, key, **kwargs):
+        raise AssertionError("never reached")
+
+    @_redis_circuit_breaker_guard
+    async def async_set_cache(self, key, value, **kwargs):
+        raise AssertionError("never reached")
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_keeps_session_routing_in_memory_without_a_warning(caplog):
+    cache = DualCache(redis_cache=_OpenBreakerRedis())  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    handler = _PROXY_SensitiveDataRoutingHandler(internal_usage_cache=InternalUsageCache(cache))
+    caplog.clear()
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Proxy"):
+        await handler.set_session_routing("quiet-session", "safe-model")
+        routed = await handler._get_routed_model("quiet-session", None)
+
+    assert routed == "safe-model"
+    assert [record.getMessage() for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert any("circuit breaker is open" in record.getMessage() for record in caplog.records)
diff --git a/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py b/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py
index 2839acab6b0..bdaca9ffc2d 100644
--- a/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py
+++ b/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py
@@ -3670,5 +3670,42 @@ async def test_post_call_success_hook_contains_header_merge_failures(
     )
 
 
+@pytest.mark.asyncio
+async def test_the_project_itpm_reservation_counts_the_request_off_the_event_loop(rate_limiter):
+    from tests.large_text import text
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+        assert_loop_stayed_free,
+        timed_with_loop_lags,
+        warm_tokenizer,
+    )
+
+    handler, _cache = rate_limiter
+    stash = get_or_create_request_stash()
+    warm_tokenizer("claude-fable-5")
+    data: dict[str, object] = {
+        "model": "claude-fable-5",
+        "messages": [{"role": "user", "content": text * 100}],
+    }
+    itpm_descriptor = {
+        "key": PROJECT_ITPM_DESCRIPTOR_KEY,
+        "value": "proj-loop:claude-fable-5",
+        "rate_limit": {"tokens_per_unit": 10_000_000, "window_size": 60},
+    }
+
+    _, took, lags = await timed_with_loop_lags(
+        lambda: handler._reserve_project_io_tokens_or_raise(
+            descriptors=[itpm_descriptor],
+            data=data,
+            requested_model="claude-fable-5",
+            user_api_key_dict=UserAPIKeyAuth(api_key=hash_token("sk-itpm-loop"), project_id="proj-loop"),
+            tpm_reservation_scopes=[],
+            tpm_reservation_amount=0,
+        )
+    )
+
+    assert stash.rate_limit_response is not None
+    assert_loop_stayed_free(took, lags)
+
+
 if __name__ == "__main__":
     pytest.main([__file__, "-v", "-s"])
diff --git a/tests/test_litellm/proxy/management_endpoints/policy_endpoints/test_ai_policy_suggester.py b/tests/test_litellm/proxy/management_endpoints/policy_endpoints/test_ai_policy_suggester.py
index 93dc429168f..bb71d67f24e 100644
--- a/tests/test_litellm/proxy/management_endpoints/policy_endpoints/test_ai_policy_suggester.py
+++ b/tests/test_litellm/proxy/management_endpoints/policy_endpoints/test_ai_policy_suggester.py
@@ -265,7 +265,7 @@ class TestSuggesterRejectsModelsWithoutToolCalling:
 
     def test_a_model_without_forced_tool_choice_support_remains_eligible(self, local_model_cost_map):
         supported_params = litellm.get_supported_openai_params(
-            model="amazon.nova-pro-v1:0",
+            model="meta.llama4-scout-17b-instruct-v1:0",
             custom_llm_provider="bedrock",
         )
 
diff --git a/tests/test_litellm/proxy/management_endpoints/test_common_daily_activity.py b/tests/test_litellm/proxy/management_endpoints/test_common_daily_activity.py
index 37a54c4901a..6cd900cb041 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_common_daily_activity.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_common_daily_activity.py
@@ -492,7 +492,7 @@ async def test_get_api_key_metadata_recovers_double_hashed_key_via_reverse_hash(
 
 @pytest.mark.asyncio
 async def test_get_api_key_metadata_permanent_miss_never_pages_tokens_or_reads_spend_logs():
-    """A dirty key no table can explain costs two digest lookups, never a token page walk or a SpendLogs scan."""
+    """Without a spend-log window a dirty key no table can explain costs two digest lookups and never a token page walk."""
     from litellm.proxy.utils import hash_token
 
     double_hashed = hash_token("b" * 64)
@@ -518,6 +518,93 @@ async def test_get_api_key_metadata_permanent_miss_never_pages_tokens_or_reads_s
     assert all("take" not in call.kwargs and "skip" not in call.kwargs for call in token_lookups)
 
 
+def _spend_log_transaction(mock_prisma: MagicMock, rows: list[dict[str, str | None]]) -> AsyncMock:
+    transaction = MagicMock()
+    transaction.execute_raw = AsyncMock(return_value=0)
+    transaction.query_raw = AsyncMock(return_value=rows)
+    mock_prisma.db.tx.return_value.__aenter__.return_value = transaction
+    return transaction.query_raw
+
+
+def _spend_log_row(digest: str, key_alias: str, user_id: str) -> dict[str, str | None]:
+    return {
+        "digest": digest,
+        "first_alias": key_alias,
+        "last_alias": key_alias,
+        "first_team": None,
+        "last_team": None,
+        "first_owner": user_id,
+        "last_owner": user_id,
+    }
+
+
+@pytest.mark.asyncio
+async def test_get_api_key_metadata_permanent_miss_with_a_window_reads_spend_logs_once_within_it():
+    from litellm.proxy.utils import hash_token
+
+    double_hashed = hash_token("permanent-miss-with-window-6852")
+    window = (datetime(2024, 1, 1), datetime(2024, 1, 4))
+    mock_prisma = MagicMock()
+    mock_prisma.db.litellm_verificationtoken.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.litellm_deletedverificationtoken.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.litellm_usertable.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.query_raw = AsyncMock(return_value=[])
+    spend_log_query_raw = _spend_log_transaction(mock_prisma, [])
+
+    result = await get_api_key_metadata(prisma_client=mock_prisma, api_keys={double_hashed}, spend_logs_window=window)
+
+    assert double_hashed not in result
+    assert mock_prisma.db.query_raw.await_count == 2
+    ((_, digests, start, end),) = [call.args for call in spend_log_query_raw.call_args_list]
+    assert digests == [double_hashed]
+    assert (start, end) == window
+
+
+@pytest.mark.asyncio
+async def test_get_daily_activity_recovers_a_session_key_alias_from_spend_logs_around_the_page_dates():
+    from litellm.proxy.utils import hash_token
+
+    session_digest = hash_token("cli-session-daily-activity-6852")
+    records = [_daily_user_spend_record(user_id="session-user", api_key=session_digest, spend=1.5)]
+    mock_prisma = MagicMock()
+    mock_prisma.db = MagicMock()
+    mock_table = MagicMock()
+    mock_table.count = AsyncMock(return_value=len(records))
+    mock_table.find_many = AsyncMock(return_value=records)
+    mock_prisma.db.litellm_dailyuserspend = mock_table
+    mock_prisma.db.litellm_verificationtoken.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.litellm_deletedverificationtoken.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.litellm_usertable.find_many = AsyncMock(
+        return_value=[SimpleNamespace(user_id="session-user", user_email="session@example.com")]
+    )
+
+    mock_prisma.db.query_raw = AsyncMock(return_value=[])
+    spend_log_query_raw = _spend_log_transaction(
+        mock_prisma, [_spend_log_row(session_digest, "cli-session-alias", "session-user")]
+    )
+
+    result = await get_daily_activity(
+        prisma_client=mock_prisma,
+        table_name="litellm_dailyuserspend",
+        entity_id_field="user_id",
+        entity_id=None,
+        entity_metadata_field=None,
+        start_date="2024-01-01",
+        end_date="2024-01-01",
+        model=None,
+        api_key=None,
+        page=1,
+        page_size=1000,
+    )
+
+    key_metadata = result.results[0].breakdown.api_keys[session_digest].metadata
+    assert key_metadata.key_alias == "cli-session-alias"
+    assert key_metadata.user_email == "session@example.com"
+    ((_, digests, start, end),) = [call.args for call in spend_log_query_raw.call_args_list]
+    assert digests == [session_digest]
+    assert (start, end) == (datetime(2023, 12, 31), datetime(2024, 1, 3))
+
+
 def test_key_metadata_includes_recovered_user_email():
     from litellm.proxy.management_endpoints.common_daily_activity import _key_metadata
 
@@ -2105,3 +2192,48 @@ async def test_get_daily_activity_aggregated_with_entity_breakdown():
     # Rollups with the entity bit set must still land in their usual buckets
     assert daily.breakdown.models["gpt-4o"].metrics.spend == 18.0
     assert daily.breakdown.api_keys["key-1"].metrics.spend == 12.0
+
+
+@pytest.mark.asyncio
+async def test_get_api_key_metadata_resolves_session_key_via_spend_log_window():
+    from litellm.proxy.utils import hash_token
+
+    session_digest = hash_token("cli-session-user-42")
+    mock_prisma = MagicMock()
+    mock_prisma.db.litellm_verificationtoken.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.litellm_deletedverificationtoken.find_many = AsyncMock(return_value=[])
+    mock_prisma.db.litellm_usertable.find_many = AsyncMock(
+        return_value=[SimpleNamespace(user_id="user-42", user_email="user42@example.com")]
+    )
+
+    mock_prisma.db.query_raw = AsyncMock(return_value=[])
+    spend_log_query_raw = _spend_log_transaction(
+        mock_prisma, [_spend_log_row(session_digest, "cli-session-user-42", "user-42")]
+    )
+
+    result = await get_api_key_metadata(
+        prisma_client=mock_prisma,
+        api_keys={session_digest},
+        spend_logs_window=(datetime(2026, 9, 7), datetime(2026, 9, 10)),
+    )
+
+    assert result[session_digest]["key_alias"] == "cli-session-user-42"
+    assert result[session_digest]["user_id"] == "user-42"
+    assert result[session_digest]["user_email"] == "user42@example.com"
+    ((_, digests, start, end),) = [call.args for call in spend_log_query_raw.call_args_list]
+    assert digests == [session_digest]
+    assert (start, end) == (datetime(2026, 9, 7), datetime(2026, 9, 10))
+
+
+def test_spend_logs_window_pads_min_minus_one_day_and_max_plus_two_days():
+    from litellm.proxy.management_endpoints.common_daily_activity import _spend_logs_window
+
+    window = _spend_logs_window({"2026-09-08", "2026-09-05", "not-a-date"})
+
+    assert window == (datetime(2026, 9, 4), datetime(2026, 9, 10))
+
+
+def test_spend_logs_window_is_none_when_no_date_parses():
+    from litellm.proxy.management_endpoints.common_daily_activity import _spend_logs_window
+
+    assert _spend_logs_window({"garbage", ""}) is None
diff --git a/tests/test_litellm/proxy/management_endpoints/test_cost_tracking_settings.py b/tests/test_litellm/proxy/management_endpoints/test_cost_tracking_settings.py
index ec62cc47018..7ece35ceedf 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_cost_tracking_settings.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_cost_tracking_settings.py
@@ -4,13 +4,17 @@ Tests for cost tracking settings management endpoints.
 Tests the GET and PATCH endpoints for managing cost discount configuration.
 """
 
+from datetime import datetime, timezone
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
 from fastapi.testclient import TestClient
+from pydantic import ValidationError
 
 
 import litellm
+from litellm._internal_context import pinned_billing_time
+from litellm.proxy._types import CostEstimateRequest
 from litellm.proxy.management_endpoints.cost_tracking_settings import router
 from litellm.proxy.proxy_server import app
 
@@ -789,13 +793,13 @@ INPUT_TOKENS = 1000
 OUTPUT_TOKENS = 500
 
 
-def _router_pricing(**pricing: float) -> MagicMock:
+def _router_pricing(model: str = AN_UNDERLYING_MODEL, **pricing: float) -> MagicMock:
     mock_router = MagicMock()
     mock_router.get_model_list.return_value = [
         {
             "model_name": AN_ALIAS,
             "litellm_params": {
-                "model": AN_UNDERLYING_MODEL,
+                "model": model,
                 "custom_llm_provider": "openai",
                 **pricing,
             },
@@ -811,9 +815,7 @@ async def _estimate(mock_router: MagicMock | None, model: str = AN_ALIAS, **over
 
     request = CostEstimateRequest(
         model=model,
-        input_tokens=INPUT_TOKENS,
-        output_tokens=OUTPUT_TOKENS,
-        **overrides,
+        **{"input_tokens": INPUT_TOKENS, "output_tokens": OUTPUT_TOKENS, **overrides},
     )
     with patch(  # test-quality-ok: proxy_server module global is the endpoint's only injection point
         "litellm.proxy.proxy_server.llm_router", mock_router
@@ -909,3 +911,299 @@ class TestEstimateCostPeriodTotals:
         assert response.cost_per_request == pytest.approx(0.0022)
         assert response.daily_margin_cost == pytest.approx(0.02)
         assert response.daily_cost == pytest.approx(0.22)
+
+
+CACHE_READ_TOKENS = 800
+CACHE_CREATION_TOKENS = 100
+REASONING_TOKENS = 200
+TEXT_INPUT_TOKENS = INPUT_TOKENS - CACHE_READ_TOKENS - CACHE_CREATION_TOKENS
+TEXT_OUTPUT_TOKENS = OUTPUT_TOKENS - REASONING_TOKENS
+
+
+async def _estimate_with_cache_and_reasoning(mock_router: MagicMock | None, model: str = AN_ALIAS, **overrides: int):
+    return await _estimate(
+        mock_router,
+        model=model,
+        cache_read_input_tokens=CACHE_READ_TOKENS,
+        cache_creation_input_tokens=CACHE_CREATION_TOKENS,
+        reasoning_tokens=REASONING_TOKENS,
+        **overrides,
+    )
+
+
+class TestEstimateCostCacheAndReasoningTokens:
+    @pytest.mark.asyncio
+    async def test_a_mapped_model_bills_cache_and_reasoning_tokens_at_their_own_rates(self, monkeypatch):
+        monkeypatch.setitem(
+            litellm.model_cost,
+            A_MAPPED_MODEL,
+            {
+                "input_cost_per_token": 3e-6,
+                "output_cost_per_token": 15e-6,
+                "cache_read_input_token_cost": 3e-7,
+                "cache_creation_input_token_cost": 3.75e-6,
+                "output_cost_per_reasoning_token": 1e-5,
+                "litellm_provider": "openai",
+                "mode": "chat",
+            },
+        )
+
+        response = await _estimate_with_cache_and_reasoning(None, model=A_MAPPED_MODEL, num_requests_per_day=10)
+
+        assert response.cache_read_cost_per_request == pytest.approx(CACHE_READ_TOKENS * 3e-7)
+        assert response.cache_creation_cost_per_request == pytest.approx(CACHE_CREATION_TOKENS * 3.75e-6)
+        assert response.reasoning_cost_per_request == pytest.approx(REASONING_TOKENS * 1e-5)
+        assert response.input_cost_per_request == pytest.approx(
+            TEXT_INPUT_TOKENS * 3e-6 + CACHE_READ_TOKENS * 3e-7 + CACHE_CREATION_TOKENS * 3.75e-6
+        )
+        assert response.output_cost_per_request == pytest.approx(TEXT_OUTPUT_TOKENS * 15e-6 + REASONING_TOKENS * 1e-5)
+        assert response.cost_per_request == pytest.approx(
+            response.input_cost_per_request + response.output_cost_per_request
+        )
+        assert response.daily_cache_read_cost == pytest.approx(10 * CACHE_READ_TOKENS * 3e-7)
+        assert response.daily_cache_creation_cost == pytest.approx(10 * CACHE_CREATION_TOKENS * 3.75e-6)
+        assert response.daily_reasoning_cost == pytest.approx(10 * REASONING_TOKENS * 1e-5)
+        assert response.monthly_cache_read_cost is None
+        assert response.cache_read_input_token_cost == pytest.approx(3e-7)
+        assert response.cache_creation_input_token_cost == pytest.approx(3.75e-6)
+        assert response.output_cost_per_reasoning_token == pytest.approx(1e-5)
+        assert (
+            response.cache_read_input_tokens,
+            response.cache_creation_input_tokens,
+            response.reasoning_tokens,
+        ) == (CACHE_READ_TOKENS, CACHE_CREATION_TOKENS, REASONING_TOKENS)
+
+    @pytest.mark.asyncio
+    async def test_a_model_without_cache_or_reasoning_prices_estimates_what_the_proxy_bills(self, monkeypatch):
+        """The cost calculator bills cache tokens of a cost-map model without cache prices at zero
+        and its reasoning tokens at the output rate. The estimate reports those effective rates."""
+        monkeypatch.setitem(
+            litellm.model_cost,
+            A_MAPPED_MODEL,
+            {"input_cost_per_token": 5e-6, "output_cost_per_token": 6e-6, "litellm_provider": "openai", "mode": "chat"},
+        )
+
+        response = await _estimate_with_cache_and_reasoning(None, model=A_MAPPED_MODEL)
+
+        assert response.cache_read_cost_per_request == 0.0
+        assert response.cache_creation_cost_per_request == 0.0
+        assert response.reasoning_cost_per_request == pytest.approx(REASONING_TOKENS * 6e-6)
+        assert response.input_cost_per_request == pytest.approx(TEXT_INPUT_TOKENS * 5e-6)
+        assert response.cost_per_request == pytest.approx(TEXT_INPUT_TOKENS * 5e-6 + OUTPUT_TOKENS * 6e-6)
+        assert response.cache_read_input_token_cost == 0.0
+        assert response.cache_creation_input_token_cost == 0.0
+        assert response.output_cost_per_reasoning_token == pytest.approx(6e-6)
+
+    @pytest.mark.asyncio
+    async def test_a_request_without_cache_or_reasoning_tokens_estimates_as_before(self, monkeypatch):
+        monkeypatch.setitem(
+            litellm.model_cost,
+            A_MAPPED_MODEL,
+            {
+                "input_cost_per_token": 3e-6,
+                "output_cost_per_token": 15e-6,
+                "cache_read_input_token_cost": 3e-7,
+                "cache_creation_input_token_cost": 3.75e-6,
+                "output_cost_per_reasoning_token": 1e-5,
+                "litellm_provider": "openai",
+                "mode": "chat",
+            },
+        )
+
+        response = await _estimate(None, model=A_MAPPED_MODEL, num_requests_per_day=10)
+
+        assert response.cost_per_request == pytest.approx(INPUT_TOKENS * 3e-6 + OUTPUT_TOKENS * 15e-6)
+        assert response.cache_read_cost_per_request == 0.0
+        assert response.cache_creation_cost_per_request == 0.0
+        assert response.reasoning_cost_per_request == 0.0
+        assert response.daily_cache_read_cost == 0.0
+        assert response.daily_reasoning_cost == 0.0
+
+    @pytest.mark.asyncio
+    async def test_a_custom_priced_deployment_bills_cache_and_reasoning_tokens_from_its_flat_rates(self):
+        response = await _estimate_with_cache_and_reasoning(
+            _router_pricing(input_cost_per_token=1e-6, output_cost_per_token=2e-6, cache_read_input_token_cost=1e-7)
+        )
+
+        assert response.cache_read_cost_per_request == pytest.approx(CACHE_READ_TOKENS * 1e-7)
+        assert response.cache_creation_cost_per_request == pytest.approx(CACHE_CREATION_TOKENS * 1e-6)
+        assert response.reasoning_cost_per_request == pytest.approx(REASONING_TOKENS * 2e-6)
+        assert response.cost_per_request == pytest.approx(
+            TEXT_INPUT_TOKENS * 1e-6 + CACHE_READ_TOKENS * 1e-7 + CACHE_CREATION_TOKENS * 1e-6 + OUTPUT_TOKENS * 2e-6
+        )
+        assert response.cache_read_input_token_cost == pytest.approx(1e-7)
+        assert response.cache_creation_input_token_cost == pytest.approx(1e-6)
+        assert response.output_cost_per_reasoning_token == pytest.approx(2e-6)
+
+    @pytest.mark.asyncio
+    async def test_a_custom_priced_deployment_of_a_mapped_model_inherits_its_built_in_cache_rates(self, monkeypatch):
+        monkeypatch.setitem(
+            litellm.model_cost,
+            A_MAPPED_MODEL,
+            {
+                "input_cost_per_token": 5e-6,
+                "output_cost_per_token": 6e-6,
+                "cache_read_input_token_cost": 5e-7,
+                "cache_creation_input_token_cost": 6.25e-6,
+                "litellm_provider": "openai",
+                "mode": "chat",
+            },
+        )
+
+        response = await _estimate_with_cache_and_reasoning(
+            _router_pricing(model=A_MAPPED_MODEL, input_cost_per_token=1e-6, output_cost_per_token=2e-6)
+        )
+
+        assert response.cache_read_cost_per_request == pytest.approx(CACHE_READ_TOKENS * 5e-7)
+        assert response.cache_creation_cost_per_request == pytest.approx(CACHE_CREATION_TOKENS * 6.25e-6)
+        assert response.input_cost_per_request == pytest.approx(
+            TEXT_INPUT_TOKENS * 1e-6 + CACHE_READ_TOKENS * 5e-7 + CACHE_CREATION_TOKENS * 6.25e-6
+        )
+        assert response.cache_read_input_token_cost == pytest.approx(5e-7)
+        assert response.cache_creation_input_token_cost == pytest.approx(6.25e-6)
+
+    @pytest.mark.asyncio
+    async def test_a_tiered_model_reports_the_rates_its_lines_were_billed_at(self, monkeypatch):
+        """Above a token tier the calculator bills every line at the tier's rate, so the reported
+        rates must be the tier's too: each line equals its token count times the rate next to it."""
+        monkeypatch.setitem(
+            litellm.model_cost,
+            A_MAPPED_MODEL,
+            {
+                "input_cost_per_token": 3e-6,
+                "output_cost_per_token": 15e-6,
+                "cache_read_input_token_cost": 3e-7,
+                "cache_creation_input_token_cost": 3.75e-6,
+                "input_cost_per_token_above_200k_tokens": 6e-6,
+                "output_cost_per_token_above_200k_tokens": 3e-5,
+                "cache_read_input_token_cost_above_200k_tokens": 6e-7,
+                "cache_creation_input_token_cost_above_200k_tokens": 7.5e-6,
+                "litellm_provider": "openai",
+                "mode": "chat",
+            },
+        )
+
+        response = await _estimate(
+            None,
+            model=A_MAPPED_MODEL,
+            input_tokens=250_000,
+            cache_read_input_tokens=200_000,
+            cache_creation_input_tokens=10_000,
+            output_tokens=1_000,
+            reasoning_tokens=200,
+        )
+
+        assert response.input_cost_per_token == pytest.approx(6e-6)
+        assert response.output_cost_per_token == pytest.approx(3e-5)
+        assert response.cache_read_input_token_cost == pytest.approx(6e-7)
+        assert response.cache_creation_input_token_cost == pytest.approx(7.5e-6)
+        assert response.output_cost_per_reasoning_token == pytest.approx(3e-5)
+        assert response.cache_read_cost_per_request == pytest.approx(200_000 * response.cache_read_input_token_cost)
+        assert response.cache_creation_cost_per_request == pytest.approx(
+            10_000 * response.cache_creation_input_token_cost
+        )
+        assert response.reasoning_cost_per_request == pytest.approx(200 * response.output_cost_per_reasoning_token)
+        assert response.input_cost_per_request == pytest.approx(
+            40_000 * response.input_cost_per_token
+            + response.cache_read_cost_per_request
+            + response.cache_creation_cost_per_request
+        )
+        assert response.output_cost_per_request == pytest.approx(1_000 * response.output_cost_per_token)
+
+    @pytest.mark.asyncio
+    async def test_a_quote_prices_its_totals_and_its_rates_at_the_same_moment(self, monkeypatch):
+        """The totals and the reported rates resolve off-peak pricing on separate paths. A quote
+        taken as a window opens must not bill on one side of it and report rates from the other."""
+        monkeypatch.setitem(
+            litellm.model_cost,
+            A_MAPPED_MODEL,
+            {
+                "input_cost_per_token": 3e-6,
+                "output_cost_per_token": 15e-6,
+                "off_peak_pricing": {
+                    "hours_utc": "02:00-03:00",
+                    "input_cost_per_token": 1e-6,
+                    "output_cost_per_token": 5e-6,
+                },
+                "litellm_provider": "openai",
+                "mode": "chat",
+            },
+        )
+
+        with pinned_billing_time(datetime(2026, 1, 1, 2, 30, tzinfo=timezone.utc)):
+            response = await _estimate(None, model=A_MAPPED_MODEL)
+
+        assert response.input_cost_per_token == pytest.approx(1e-6)
+        assert response.output_cost_per_token == pytest.approx(5e-6)
+        assert response.input_cost_per_request == pytest.approx(INPUT_TOKENS * response.input_cost_per_token)
+        assert response.output_cost_per_request == pytest.approx(OUTPUT_TOKENS * response.output_cost_per_token)
+
+
+    @pytest.mark.asyncio
+    async def test_an_unrouted_model_reports_the_rates_of_the_provider_the_calculator_inferred(self, monkeypatch):
+        """The cost calculator infers a provider this endpoint never resolved, and the provider decides
+        whether a tier threshold is inclusive. xai bills a request sitting exactly on the 200k threshold
+        at the tier rate, so the reported rates have to be the tier's rather than the sub-tier base."""
+        an_xai_model = "xai/tiered-model"
+        monkeypatch.setitem(
+            litellm.model_cost,
+            an_xai_model,
+            {
+                "input_cost_per_token": 3e-6,
+                "output_cost_per_token": 15e-6,
+                "cache_read_input_token_cost": 3e-7,
+                "input_cost_per_token_above_200k_tokens": 6e-6,
+                "output_cost_per_token_above_200k_tokens": 3e-5,
+                "cache_read_input_token_cost_above_200k_tokens": 6e-7,
+                "litellm_provider": "xai",
+                "mode": "chat",
+            },
+        )
+
+        response = await _estimate(
+            None,
+            model=an_xai_model,
+            input_tokens=200_000,
+            cache_read_input_tokens=100_000,
+            output_tokens=1_000,
+        )
+
+        assert response.input_cost_per_token == pytest.approx(6e-6)
+        assert response.output_cost_per_token == pytest.approx(3e-5)
+        assert response.cache_read_input_token_cost == pytest.approx(6e-7)
+        assert response.cache_read_cost_per_request == pytest.approx(100_000 * response.cache_read_input_token_cost)
+        assert response.input_cost_per_request == pytest.approx(
+            100_000 * response.input_cost_per_token + response.cache_read_cost_per_request
+        )
+        assert response.output_cost_per_request == pytest.approx(1_000 * response.output_cost_per_token)
+
+
+class TestCostEstimateRequestTokenSubsets:
+    def test_cache_tokens_beyond_the_input_tokens_are_rejected(self):
+        with pytest.raises(ValidationError, match="cannot exceed input_tokens"):
+            CostEstimateRequest(
+                model=AN_ALIAS,
+                input_tokens=INPUT_TOKENS,
+                output_tokens=OUTPUT_TOKENS,
+                cache_read_input_tokens=INPUT_TOKENS,
+                cache_creation_input_tokens=1,
+            )
+
+    def test_reasoning_tokens_beyond_the_output_tokens_are_rejected(self):
+        with pytest.raises(ValidationError, match="cannot exceed output_tokens"):
+            CostEstimateRequest(
+                model=AN_ALIAS,
+                input_tokens=INPUT_TOKENS,
+                output_tokens=OUTPUT_TOKENS,
+                reasoning_tokens=OUTPUT_TOKENS + 1,
+            )
+
+    def test_the_endpoint_answers_422_when_cache_tokens_exceed_input_tokens(self):
+        response = client.post(
+            "/cost/estimate",
+            headers={"Authorization": "Bearer sk-1234"},
+            json={"model": AN_ALIAS, "input_tokens": 1000, "output_tokens": 100, "cache_read_input_tokens": 8000},
+        )
+
+        assert response.status_code == 422
+        assert "cannot exceed input_tokens" in response.text
diff --git a/tests/test_litellm/proxy/management_endpoints/test_customer_endpoints.py b/tests/test_litellm/proxy/management_endpoints/test_customer_endpoints.py
index 1225cb80224..bd59a82cbd2 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_customer_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_customer_endpoints.py
@@ -763,6 +763,7 @@ _EXPECTED_CUSTOMER = {
         "blocked_tools": [],
         "search_tools": [],
         "mcp_tool_search_enabled": None,
+        "skills": None,
     },
 }
 
diff --git a/tests/test_litellm/proxy/management_endpoints/test_key_management_endpoints.py b/tests/test_litellm/proxy/management_endpoints/test_key_management_endpoints.py
index a873a367eab..65cc23ea67f 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_key_management_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_key_management_endpoints.py
@@ -5085,6 +5085,104 @@ async def test_delete_verification_tokens_persists_deleted_keys(monkeypatch):
     assert len(deleted_keys) == 2
 
 
+class _JWTMappingRow:
+    def __init__(self, token, jwt_claim_name, jwt_claim_value):
+        self.token = token
+        self.jwt_claim_name = jwt_claim_name
+        self.jwt_claim_value = jwt_claim_value
+
+
+class _CascadingJWTMappingTable:
+    """Mapping rows that LiteLLM_JWTKeyMapping_token_fkey drops when their key is deleted."""
+
+    def __init__(self, rows):
+        self.rows = rows
+
+    async def find_many(self, where, **kwargs):
+        return [row for row in self.rows if row.token == where["token"]]
+
+    def cascade(self, deleted_tokens):
+        self.rows = [row for row in self.rows if row.token not in deleted_tokens]
+
+
+class _RecordingEvict:
+    def __init__(self):
+        self.cache_keys = ()
+
+    async def __call__(self, cache_keys, user_api_key_cache):
+        self.cache_keys = tuple(cache_keys)
+
+
+@pytest.mark.asyncio
+async def test_delete_verification_tokens_evicts_jwt_key_mapping_cache(monkeypatch):
+    """Deleting a key must evict its jwt_key_mapping cache entries (LIT-5380).
+
+    The FK cascade removes the mapping rows, so a surviving cache entry would keep
+    resolving the deleted token hash and 401 every JWT call from that identity until
+    virtual_key_mapping_cache_ttl expires, instead of auto-registering again.
+    """
+    jwt_table = _CascadingJWTMappingTable(
+        [_JWTMappingRow("hashed-token-1", "email", "user@example.com")]
+    )
+
+    key1 = LiteLLM_VerificationToken(
+        token="hashed-token-1",
+        user_id="user-123",
+        team_id=None,
+        key_alias="jwt-mapped-key",
+        spend=0.0,
+        max_budget=None,
+        models=[],
+        aliases={},
+        config={},
+        permissions={},
+        metadata={},
+        model_max_budget={},
+        model_spend={},
+        soft_budget_cooldown=False,
+        allowed_routes=[],
+    )
+
+    mock_prisma_client = AsyncMock()
+    mock_prisma_client.db.litellm_verificationtoken.find_many = AsyncMock(
+        return_value=[key1]
+    )
+    mock_prisma_client.db.litellm_jwtkeymapping = jwt_table
+    mock_prisma_client.db.litellm_deletedverificationtoken.create_many = AsyncMock()
+
+    async def cascading_delete_data(tokens):
+        jwt_table.cascade(tokens)
+        return list(tokens)
+
+    mock_prisma_client.delete_data = AsyncMock(side_effect=cascading_delete_data)
+
+    recording_evict = _RecordingEvict()
+    monkeypatch.setattr(
+        "litellm.proxy.management_endpoints.key_management_endpoints.evict_and_broadcast",
+        recording_evict,
+    )
+    monkeypatch.setattr(
+        "litellm.proxy.management_endpoints.key_management_endpoints._hash_token_if_needed",
+        lambda token: token,
+    )
+    monkeypatch.setattr(
+        "litellm.proxy.proxy_server.prisma_client",
+        mock_prisma_client,
+    )
+
+    await delete_verification_tokens(
+        tokens=["hashed-token-1"],
+        user_api_key_cache=MagicMock(),
+        user_api_key_dict=UserAPIKeyAuth(
+            user_id="admin-user",
+            api_key="sk-admin",
+            user_role=LitellmUserRoles.PROXY_ADMIN.value,
+        ),
+    )
+
+    assert recording_evict.cache_keys == ("jwt_key_mapping:email:user@example.com",)
+
+
 @pytest.mark.asyncio
 async def test_delete_key_fn_persists_deleted_keys(monkeypatch):
     from litellm.proxy._types import KeyRequest
@@ -17975,6 +18073,32 @@ def test_key_request_blank_organization_id_is_unset():
     assert UpdateKeyRequest(key="sk-1", organization_id="org-1").organization_id == "org-1"
 
 
+def test_update_key_request_blank_team_id_is_not_a_team_change():
+    from litellm.proxy._types import UpdateKeyRequest
+    from litellm.proxy.management_endpoints.key_management_endpoints import (
+        is_different_team,
+    )
+
+    blank = UpdateKeyRequest(key="sk-1", team_id="", key_alias="renamed")
+    assert blank.team_id is None
+    assert "team_id" not in blank.model_dump(exclude_unset=True)
+    assert blank.model_dump(exclude_unset=True) == {"key": "sk-1", "key_alias": "renamed"}
+    assert is_different_team(data=blank, existing_key_row=LiteLLM_VerificationToken(token="hashed")) is False
+    assert (
+        is_different_team(data=blank, existing_key_row=LiteLLM_VerificationToken(token="hashed", team_id="team-1"))
+        is False
+    )
+    assert "team_id" in UpdateKeyRequest(key="sk-1", team_id=None).model_dump(exclude_unset=True)
+    assert UpdateKeyRequest(key="sk-1", team_id="team-1").team_id == "team-1"
+    assert (
+        is_different_team(
+            data=UpdateKeyRequest(key="sk-1", team_id="team-1"),
+            existing_key_row=LiteLLM_VerificationToken(token="hashed"),
+        )
+        is True
+    )
+
+
 def test_key_generation_check_blank_team_id_uses_personal_permissions(monkeypatch):
     """key_generation_check with team_id="" must take the personal-key path instead
     of failing the team lookup with "Unable to find team object" (LIT-3925)."""
diff --git a/tests/test_litellm/proxy/management_endpoints/test_mcp_management_endpoints.py b/tests/test_litellm/proxy/management_endpoints/test_mcp_management_endpoints.py
index 71ff7de89b0..5e00e7d75be 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_mcp_management_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_mcp_management_endpoints.py
@@ -4802,6 +4802,72 @@ async def test_store_mcp_oauth_user_credential_returns_status():
     assert result.expires_at == "2099-01-01T00:00:00+00:00"
 
 
+@pytest.mark.asyncio
+async def test_store_mcp_oauth_user_credential_blocked_when_identity_binding_enforced():
+    """The direct opaque-token POST must be closed for enforce-mode identity-bound servers,
+    otherwise it bypasses the token-relay principal check."""
+    from litellm.proxy._types import MCPOAuthUserCredentialRequest
+    from litellm.types.mcp import MCPAuth, MCPTransport
+    from litellm.types.mcp_server.mcp_server_manager import MCPOAuthIdentityBinding, MCPServer
+
+    if not mgmt_endpoints.MCP_AVAILABLE:
+        pytest.skip("MCP module not installed")
+
+    from litellm.proxy._experimental.mcp_server import mcp_server_manager as manager_module
+    from litellm.proxy.management_endpoints.mcp_management_endpoints import (
+        store_mcp_oauth_user_credential,
+    )
+
+    server_id = "srv-binding-1"
+    bound_server = MCPServer(
+        server_id=server_id,
+        name=server_id,
+        url="https://mcp.example.com",
+        transport=MCPTransport.http,
+        auth_type=MCPAuth.oauth2,
+        oauth_identity_binding=MCPOAuthIdentityBinding(
+            mode="enforce",
+            issuer="https://idp.example.com",
+            audiences=["litellm-client"],
+        ),
+    )
+    store_mock = AsyncMock(return_value=None)
+
+    with (
+        patch(  # test-quality-ok: mirrors the existing store-credential tests in this file
+            "litellm.proxy.management_endpoints.mcp_management_endpoints.get_prisma_client_or_throw",
+            return_value=_make_prisma_client(),
+        ),
+        patch(  # test-quality-ok: mirrors the existing store-credential tests in this file
+            "litellm.proxy.management_endpoints.mcp_management_endpoints.get_mcp_server",
+            new=AsyncMock(return_value=generate_mock_mcp_server_db_record(server_id=server_id)),
+        ),
+        patch(  # test-quality-ok: mirrors the existing store-credential tests in this file
+            "litellm.proxy.management_endpoints.mcp_management_endpoints._user_has_admin_view",
+            return_value=True,
+        ),
+        patch.object(  # test-quality-ok: registry is a module-level singleton; injecting it would change the endpoint signature
+            manager_module.global_mcp_server_manager,
+            "get_mcp_server_by_id",
+            return_value=bound_server,
+        ),
+        patch(  # test-quality-ok: asserting the DB write is never reached is the point of the test
+            "litellm.proxy.management_endpoints.mcp_management_endpoints.store_user_oauth_credential",
+            new=store_mock,
+        ),
+    ):
+        with pytest.raises(HTTPException) as exc_info:
+            await store_mcp_oauth_user_credential(
+                server_id=server_id,
+                payload=MCPOAuthUserCredentialRequest(access_token="opaque-tok", expires_in=3600),
+                user_api_key_dict=_make_user_auth("user-123"),
+            )
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail["error"] == "oauth_identity_binding_enforced"
+    store_mock.assert_not_called()
+
+
 @pytest.mark.asyncio
 async def test_delete_mcp_oauth_user_credential_only_deletes_oauth():
     """delete_mcp_oauth_user_credential only deletes OAuth2 credentials, not BYOK."""
diff --git a/tests/test_litellm/proxy/management_endpoints/test_model_management_endpoints.py b/tests/test_litellm/proxy/management_endpoints/test_model_management_endpoints.py
index c02f886fc31..5325e069813 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_model_management_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_model_management_endpoints.py
@@ -392,6 +392,185 @@ class TestModelManagementAuthChecks:
             assert exc_info.value.code == "403"
             mock_update.assert_not_awaited()
 
+    def test_can_user_set_aws_session_tags_admin_success(self):
+        result = ModelManagementAuthChecks.can_user_set_aws_session_tags(
+            litellm_params=LiteLLM_Params(
+                model="bedrock/test_model", aws_session_tags=[{"Key": "team", "Value": "genai"}]
+            ),
+            user_api_key_dict=self.admin_user,
+        )
+        assert result is True
+
+    def test_can_user_set_aws_session_tags_without_tags_allows_any_role(self):
+        result = ModelManagementAuthChecks.can_user_set_aws_session_tags(
+            litellm_params=LiteLLM_Params(model="bedrock/test_model", aws_role_name="arn:aws:iam::123:role/x"),
+            user_api_key_dict=self.team_admin_user,
+        )
+        assert result is True
+
+    def test_can_user_set_aws_session_tags_team_admin_fails(self):
+        with pytest.raises(Exception, match="Only a proxy admin can set aws_session_tags") as exc_info:
+            ModelManagementAuthChecks.can_user_set_aws_session_tags(
+                litellm_params=LiteLLM_Params(
+                    model="bedrock/test_model", aws_session_tags=[{"Key": "team", "Value": "genai"}]
+                ),
+                user_api_key_dict=self.team_admin_user,
+            )
+        assert exc_info.value.code == "403"
+        assert exc_info.value.param == "aws_session_tags"
+
+    def test_can_user_set_aws_session_tags_unchanged_existing_allows_any_role(self):
+        result = ModelManagementAuthChecks.can_user_set_aws_session_tags(
+            litellm_params=LiteLLM_Params(
+                model="bedrock/test_model",
+                aws_session_tags=[{"Key": "team", "Value": "genai"}, {"Key": "env", "Value": "prod"}],
+            ),
+            user_api_key_dict=self.team_admin_user,
+            existing_litellm_params=LiteLLM_Params(
+                model="bedrock/test_model",
+                aws_session_tags=[{"Key": "env", "Value": "prod"}, {"Key": "team", "Value": "genai"}],
+            ),
+        )
+        assert result is True
+
+    def test_can_user_set_aws_session_tags_changed_value_fails_for_team_admin(self):
+        with pytest.raises(Exception, match="Only a proxy admin can set aws_session_tags") as exc_info:
+            ModelManagementAuthChecks.can_user_set_aws_session_tags(
+                litellm_params=LiteLLM_Params(
+                    model="bedrock/test_model", aws_session_tags=[{"Key": "team", "Value": "platform"}]
+                ),
+                user_api_key_dict=self.team_admin_user,
+                existing_litellm_params=LiteLLM_Params(
+                    model="bedrock/test_model", aws_session_tags=[{"Key": "team", "Value": "genai"}]
+                ),
+            )
+        assert exc_info.value.code == "403"
+
+    @pytest.mark.asyncio
+    async def test_add_new_model_rejects_aws_session_tags_for_non_admin(self):
+        from litellm.proxy._types import ProxyException
+        from litellm.proxy.management_endpoints.model_management_endpoints import (
+            add_new_model,
+        )
+
+        mock_prisma = MagicMock()
+        with (
+            patch("litellm.proxy.proxy_server.prisma_client", mock_prisma),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.store_model_in_db", True),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.premium_user", True),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch(  # test-quality-ok: prior auth check needs a live DB; only the session tag check is under test
+                "litellm.proxy.management_endpoints.model_management_endpoints.ModelManagementAuthChecks.can_user_make_model_call",
+                new=AsyncMock(return_value=None),
+            ),
+        ):
+            with pytest.raises(ProxyException) as exc_info:
+                await add_new_model(
+                    model_params=Deployment(
+                        model_name="tagged-bedrock",
+                        litellm_params=LiteLLM_Params(
+                            model="bedrock/anthropic.claude-opus-4-6-v1:0",
+                            aws_role_name="arn:aws:iam::123456789012:role/team-role",
+                            aws_session_tags=[{"Key": "team", "Value": "genai"}],
+                        ),
+                        model_info={"id": "session-tags-create-test", "team_id": "test_team"},
+                    ),
+                    user_api_key_dict=self.team_admin_user,
+                )
+            assert exc_info.value.code == "403"
+            assert exc_info.value.param == "aws_session_tags"
+            mock_prisma.db.litellm_proxymodeltable.create.assert_not_called()
+
+    @pytest.mark.asyncio
+    async def test_patch_model_rejects_aws_session_tags_for_non_admin(self):
+        from litellm.proxy._types import ProxyException
+        from litellm.proxy.management_endpoints.model_management_endpoints import (
+            patch_model,
+        )
+        from litellm.types.router import updateLiteLLMParams
+
+        model_id = "session-tags-patch-test"
+        db_model = Deployment(
+            model_name="tagged-bedrock",
+            litellm_params=LiteLLM_Params(
+                model="bedrock/anthropic.claude-opus-4-6-v1:0",
+                aws_role_name="arn:aws:iam::123456789012:role/team-role",
+            ),
+            model_info={"id": model_id, "team_id": "test_team"},
+        )
+        with (
+            patch("litellm.proxy.proxy_server.prisma_client", MagicMock()),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.llm_router", MagicMock()),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.store_model_in_db", True),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.premium_user", True),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch(  # test-quality-ok: stubs the DB row fetch; only the session tag check is under test
+                "litellm.proxy.management_endpoints.model_management_endpoints.get_db_model",
+                new=AsyncMock(return_value=db_model),
+            ),
+            patch(  # test-quality-ok: prior auth check needs a live DB; only the session tag check is under test
+                "litellm.proxy.management_endpoints.model_management_endpoints.ModelManagementAuthChecks.can_user_make_model_call",
+                new=AsyncMock(return_value=None),
+            ),
+            patch(  # test-quality-ok: asserts the DB write is never reached on rejection
+                "litellm.proxy.management_endpoints.model_management_endpoints._update_team_model_in_db",
+                new=AsyncMock(),
+            ) as mock_update,
+        ):
+            with pytest.raises(ProxyException) as exc_info:
+                await patch_model(
+                    model_id=model_id,
+                    patch_data=updateDeployment(
+                        litellm_params=updateLiteLLMParams(aws_session_tags=[{"Key": "team", "Value": "genai"}])
+                    ),
+                    user_api_key_dict=self.team_admin_user,
+                )
+            assert exc_info.value.code == "403"
+            assert exc_info.value.param == "aws_session_tags"
+            mock_update.assert_not_awaited()
+
+    @pytest.mark.asyncio
+    async def test_update_model_rejects_aws_session_tags_for_non_admin(self):
+        from litellm.proxy._types import ProxyException
+        from litellm.proxy.management_endpoints.model_management_endpoints import (
+            update_model,
+        )
+        from litellm.types.router import updateLiteLLMParams
+
+        model_id = "session-tags-put-test"
+        existing = Deployment(
+            model_name="tagged-bedrock",
+            litellm_params=LiteLLM_Params(
+                model="bedrock/anthropic.claude-opus-4-6-v1:0",
+                aws_role_name="arn:aws:iam::123456789012:role/team-role",
+            ),
+            model_info={"id": model_id, "team_id": "test_team"},
+        )
+        existing_row = MagicMock()
+        existing_row.model_dump.return_value = existing.model_dump()
+        mock_prisma = MagicMock()
+        mock_prisma.db.litellm_proxymodeltable.find_unique = AsyncMock(return_value=existing_row)
+        mock_prisma.db.litellm_proxymodeltable.update = AsyncMock()
+        with (
+            patch("litellm.proxy.proxy_server.prisma_client", mock_prisma),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.llm_router", None),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.store_model_in_db", True),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch("litellm.proxy.proxy_server.premium_user", True),  # test-quality-ok: endpoint reads proxy server globals with no injection seam
+            patch(  # test-quality-ok: prior auth check needs a live DB; only the session tag check is under test
+                "litellm.proxy.management_endpoints.model_management_endpoints.ModelManagementAuthChecks.can_user_make_model_call",
+                new=AsyncMock(return_value=None),
+            ),
+        ):
+            with pytest.raises(ProxyException) as exc_info:
+                await update_model(
+                    model_params=updateDeployment(
+                        litellm_params=updateLiteLLMParams(aws_session_tags=[{"Key": "team", "Value": "genai"}]),
+                        model_info=ModelInfo(id=model_id),
+                    ),
+                    user_api_key_dict=self.team_admin_user,
+                )
+            assert exc_info.value.code == "403"
+            assert exc_info.value.param == "aws_session_tags"
+            mock_prisma.db.litellm_proxymodeltable.update.assert_not_awaited()
+
     def test_can_user_attach_credential_internal_user_fails(self):
         with pytest.raises(Exception, match="Only a proxy admin can attach a stored credential") as exc_info:
             ModelManagementAuthChecks.can_user_attach_credential(
@@ -1990,7 +2169,7 @@ class TestModelInfoEndpoint:
         ):
             mock_router.get_fully_blocked_model_names.return_value = set()
             mock_router.get_model_list.return_value = []
-            mock_router.get_configured_token_limits.return_value = (None, None)
+            mock_router.get_model_listing_info.return_value = None
             mock_router.get_deployment_by_model_group_name.return_value = Deployment(
                 model_name="gpt-4",
                 litellm_params=LiteLLM_Params(model="openai/gpt-4"),
@@ -2067,7 +2246,7 @@ class TestModelInfoEndpoint:
         ):
             mock_router.get_fully_blocked_model_names.return_value = set()
             mock_router.get_model_list.return_value = []
-            mock_router.get_configured_token_limits.return_value = (None, None)
+            mock_router.get_model_listing_info.return_value = None
             mock_router.get_deployment_by_model_group_name.return_value = Deployment(
                 model_name="team-model-1",
                 litellm_params=LiteLLM_Params(model="custom/team-model-1"),
diff --git a/tests/test_litellm/proxy/management_endpoints/test_organization_endpoints.py b/tests/test_litellm/proxy/management_endpoints/test_organization_endpoints.py
index 4d13e054e46..7c3f4e2c6e9 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_organization_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_organization_endpoints.py
@@ -1,7 +1,8 @@
 import asyncio
 import json
 from litellm._uuid import uuid
-from typing import Optional, cast
+from types import MappingProxyType
+from typing import Final, Mapping, Optional, cast
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
@@ -1226,3 +1227,83 @@ def test_v2_update_organization_is_in_openapi_schema():
     v2_path = app.openapi()["paths"]["/v2/organization/{organization_id}"]
     assert v2_path["patch"]["tags"] == ["organization management"]
     assert "OrganizationUpdateRequestV2" in json.dumps(v2_path["patch"]["requestBody"])
+
+
+def _organization_route_targets() -> list[tuple[str, str]]:
+    from fastapi.routing import APIRoute
+
+    from litellm.proxy.management_endpoints.organization_endpoints import router
+
+    return [
+        (method, route.path.replace("{organization_id}", "org-under-test"))
+        for route in router.routes
+        if isinstance(route, APIRoute)
+        for method in sorted(route.methods - {"HEAD", "OPTIONS"})
+    ]
+
+
+_ORGANIZATION_ROUTE_REQUESTS: Final[Mapping[tuple[str, str], Mapping[str, object]]] = MappingProxyType(
+    {
+        ("POST", "/organization/new"): {"json": {"organization_alias": "org-under-test"}},
+        ("DELETE", "/organization/delete"): {"json": {"organization_ids": ["org-under-test"]}},
+        ("GET", "/organization/info"): {"params": {"organization_id": "org-under-test"}},
+        ("POST", "/organization/info"): {"json": {"organizations": ["org-under-test"]}},
+        ("POST", "/organization/member_add"): {
+            "json": {"organization_id": "org-under-test", "member": {"user_id": "user-1", "role": "internal_user"}}
+        },
+        ("PATCH", "/organization/member_update"): {"json": {"organization_id": "org-under-test", "user_id": "user-1"}},
+        ("DELETE", "/organization/member_delete"): {"json": {"organization_id": "org-under-test", "user_id": "user-1"}},
+    }
+)
+
+
+def _organization_request(method: str, path: str) -> Mapping[str, object]:
+    return _ORGANIZATION_ROUTE_REQUESTS.get((method, path), {"json": {}})
+
+
+def _organization_test_client() -> TestClient:
+    from fastapi import FastAPI
+
+    from litellm.proxy._types import LitellmUserRoles, ProxyException, UserAPIKeyAuth
+    from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
+    from litellm.proxy.management_endpoints.organization_endpoints import router
+    from litellm.proxy.proxy_server import openai_exception_handler
+
+    app = FastAPI()
+    app.include_router(router)
+    app.add_exception_handler(ProxyException, openai_exception_handler)
+    app.dependency_overrides[user_api_key_auth] = lambda: UserAPIKeyAuth(
+        api_key="sk-test", user_role=LitellmUserRoles.PROXY_ADMIN
+    )
+    return TestClient(app, raise_server_exceptions=False)
+
+
+@pytest.mark.parametrize(("method", "path"), _organization_route_targets())
+def test_organization_routes_are_blocked_without_enterprise_license(monkeypatch, method, path):
+    """Every /organization route is enterprise-only, even for a proxy admin sending a valid request."""
+    import litellm.proxy.proxy_server as proxy_server
+
+    monkeypatch.setattr(proxy_server, "premium_user", False, raising=False)
+    monkeypatch.setattr(proxy_server, "prisma_client", None, raising=False)
+
+    response = _organization_test_client().request(method, path, **_organization_request(method, path))
+
+    assert response.status_code == 403
+    assert "Organizations" in response.json()["detail"]["error"]
+
+
+@pytest.mark.parametrize(("method", "path"), _organization_route_targets())
+def test_organization_routes_reach_their_handler_with_enterprise_license(monkeypatch, method, path):
+    """The same request a license refuses above now reaches the handler, which is the code reporting the missing database."""
+    import litellm.proxy.proxy_server as proxy_server
+    from litellm.proxy._types import CommonProxyErrors
+
+    monkeypatch.setattr(proxy_server, "premium_user", True, raising=False)
+    monkeypatch.setattr(proxy_server, "prisma_client", None, raising=False)
+
+    response = _organization_test_client().request(method, path, **_organization_request(method, path))
+
+    assert response.status_code == 500
+    assert any(
+        message in response.text for message in (CommonProxyErrors.db_not_connected_error.value, "No db connected")
+    )
diff --git a/tests/test_litellm/proxy/management_endpoints/test_team_endpoints.py b/tests/test_litellm/proxy/management_endpoints/test_team_endpoints.py
index 051e6bed4fd..2f6561046b1 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_team_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_team_endpoints.py
@@ -2205,6 +2205,50 @@ async def test_team_model_add_delete_refresh_team_cache(endpoint_name):
         assert update_call_kwargs.get("include", {}).get("object_permission") is True
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize("endpoint_name", ["team_model_add", "team_model_delete"])
+async def test_team_model_add_delete_keep_model_aliases_in_team_cache(endpoint_name, monkeypatch):
+    """LIT-5858: Prisma only returns `litellm_model_table` when the `update` asks for it, so the refreshed
+    cache entry lost the team's model aliases and JWT alias requests 403'd until the next DB read."""
+    from litellm.proxy._types import TeamModelAddRequest, TeamModelDeleteRequest
+    from litellm.proxy.auth.team_grants import team_model_aliases
+    from litellm.proxy.common_utils.user_api_key_cache import UserApiKeyCache
+    from litellm.proxy.management_endpoints.team_endpoints import team_model_add, team_model_delete
+
+    columns = {"team_id": "team-1234", "models": ["gpt-4o", "openai/*"]}
+    alias_table = {"id": 1, "model_aliases": '{"fast": "gpt-4o"}', "created_by": "admin", "updated_by": "admin"}
+
+    async def update(where, data, include=None):
+        row = {**columns, "litellm_model_table": alias_table} if (include or {}).get("litellm_model_table") else columns
+        return SimpleNamespace(team_id="team-1234", model_dump=lambda: row)
+
+    prisma_client = MagicMock()
+    prisma_client.db.litellm_teamtable.find_unique = AsyncMock(return_value=SimpleNamespace(model_dump=lambda: columns))
+    prisma_client.db.litellm_teamtable.update = AsyncMock(side_effect=update)
+    prisma_client.db.execute_raw = AsyncMock(return_value=None)
+    cache = UserApiKeyCache()
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", prisma_client)
+    monkeypatch.setattr("litellm.proxy.proxy_server.user_api_key_cache", cache)
+    monkeypatch.setattr("litellm.proxy.proxy_server.proxy_logging_obj", None)
+
+    admin = UserAPIKeyAuth(user_role=LitellmUserRoles.PROXY_ADMIN, user_id="admin")
+    if endpoint_name == "team_model_add":
+        await team_model_add(
+            data=TeamModelAddRequest(team_id="team-1234", models=["team-byok-1"]),
+            http_request=MagicMock(),
+            user_api_key_dict=admin,
+        )
+    else:
+        await team_model_delete(
+            data=TeamModelDeleteRequest(team_id="team-1234", models=["openai/*"]),
+            http_request=MagicMock(),
+            user_api_key_dict=admin,
+        )
+
+    cached_team = await cache.async_get_cache(key="team_id:team-1234", model_type=LiteLLM_TeamTableCachedObj)
+    assert team_model_aliases(cached_team) == {"fast": "gpt-4o"}
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "endpoint_name",
diff --git a/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py b/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py
index 8d8bc15f9be..2050e65d2a1 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_ui_sso.py
@@ -2616,6 +2616,28 @@ class TestCLIKeyRegenerationFlow:
         )
         cache.set_cache.assert_not_called()
 
+    def test_cli_sso_flow_lookup_treats_an_open_redis_breaker_as_a_miss(self):
+        """A Redis read refused by the open circuit breaker is a missing session, not a server error.
+
+        The direct Redis read is what keeps the flow authoritative across workers, so the
+        refusal must not fall back to a possibly stale in-memory copy either.
+        """
+        from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
+        from litellm.proxy.management_endpoints.ui_sso import _get_cli_sso_flow_or_raise
+
+        redis_cache = MagicMock()
+        redis_cache.get_cache.side_effect = RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+        cache = MagicMock()
+        cache.redis_cache = redis_cache
+        cache.get_cache.return_value = {"poll_secret_hash": "stale", "sso_complete": False}
+
+        with pytest.raises(HTTPException) as exc_info:
+            _get_cli_sso_flow_or_raise(login_id="cli-breaker_open_1234567890", cache=cache)
+
+        assert exc_info.value.status_code == 400
+        assert "not found or expired" in exc_info.value.detail
+        cache.get_cache.assert_not_called()
+
     def test_cli_sso_flow_with_enum_survives_redis_round_trip(self):
         """
         RedisCache stores values via str(value) and reads them back through
diff --git a/tests/test_litellm/proxy/management_helpers/test_object_permission_utils.py b/tests/test_litellm/proxy/management_helpers/test_object_permission_utils.py
index d7ebb1f60bf..078315c2bf8 100644
--- a/tests/test_litellm/proxy/management_helpers/test_object_permission_utils.py
+++ b/tests/test_litellm/proxy/management_helpers/test_object_permission_utils.py
@@ -122,6 +122,29 @@ async def test_set_object_permission_persists_mcp_tool_search_enabled():
     assert created_data["mcp_tool_search_enabled"] is True
 
 
+@pytest.mark.asyncio
+async def test_set_object_permission_persists_skills():
+    mock_prisma_client = MagicMock()
+    mock_created_permission = MagicMock()
+    mock_created_permission.object_permission_id = "perm_id"
+    mock_prisma_client.db.litellm_objectpermissiontable.create = AsyncMock(
+        return_value=mock_created_permission
+    )
+
+    data_json = {
+        "object_permission": LiteLLM_ObjectPermissionBase(skills=["private-skill"]).model_dump(),
+    }
+
+    await _set_object_permission(data_json=data_json, prisma_client=mock_prisma_client)
+
+    created_data = (
+        mock_prisma_client.db.litellm_objectpermissiontable.create.call_args.kwargs[
+            "data"
+        ]
+    )
+    assert created_data["skills"] == ["private-skill"]
+
+
 # ---- Tests for _extract_requested_mcp_server_ids ----
 
 
diff --git a/tests/test_litellm/proxy/pass_through_endpoints/llm_provider_handlers/test_openai_passthrough_logging_handler.py b/tests/test_litellm/proxy/pass_through_endpoints/llm_provider_handlers/test_openai_passthrough_logging_handler.py
index 6f9142c85df..a3d3ae32169 100644
--- a/tests/test_litellm/proxy/pass_through_endpoints/llm_provider_handlers/test_openai_passthrough_logging_handler.py
+++ b/tests/test_litellm/proxy/pass_through_endpoints/llm_provider_handlers/test_openai_passthrough_logging_handler.py
@@ -9,8 +9,10 @@ import pytest
 
 import litellm
 from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
+from litellm.litellm_core_utils.token_counter import high_detail_image_token_upper_bound
 from litellm.proxy.pass_through_endpoints.llm_provider_handlers.openai_passthrough_logging_handler import (
     OpenAIPassthroughLoggingHandler,
+    count_relayed_prompt_tokens,
 )
 from litellm.proxy.pass_through_endpoints.success_handler import (
     PassThroughEndpointLogging,
@@ -2037,3 +2039,56 @@ class TestOpenAIPassthroughEmbeddingsSpendLog:
 
 if __name__ == "__main__":
     pytest.main([__file__])
+
+
+ONE_PIXEL_PNG_DATA_URL = (
+    "data:image/png;base64,iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAQAAAC1HAwCAAAAC0lEQVR42mNkYAAAAAYAAjCB0C8AAAAASUVORK5CYII="
+)
+UNREACHABLE_IMAGE_URL = "http://127.0.0.1:9/doc.png"
+TEXT_ONLY_MESSAGES = [{"role": "user", "content": [{"type": "text", "text": "Describe this"}]}]
+
+
+def _image_messages(url: str, detail: str) -> list[dict]:
+    return [
+        {
+            "role": "user",
+            "content": [
+                {"type": "text", "text": "Describe this"},
+                {"type": "image_url", "image_url": {"url": url, "detail": detail}},
+            ],
+        }
+    ]
+
+
+def test_count_relayed_prompt_tokens_counts_a_data_url_image_exactly():
+    messages = _image_messages(ONE_PIXEL_PNG_DATA_URL, "high")
+
+    assert count_relayed_prompt_tokens("gpt-4.1-mini", messages) == litellm.token_counter(
+        model="gpt-4.1-mini", messages=messages
+    )
+
+
+def test_count_relayed_prompt_tokens_keeps_a_low_detail_remote_image_at_the_base_count():
+    messages = _image_messages(UNREACHABLE_IMAGE_URL, "low")
+
+    assert count_relayed_prompt_tokens("gpt-4.1-mini", messages) == litellm.token_counter(
+        model="gpt-4.1-mini", messages=messages
+    )
+    assert count_relayed_prompt_tokens("gpt-4.1-mini", messages) < high_detail_image_token_upper_bound()
+
+
+def test_count_relayed_prompt_tokens_charges_only_the_remote_high_detail_image_at_the_upper_bound():
+    messages = _image_messages(UNREACHABLE_IMAGE_URL, "high")
+
+    assert count_relayed_prompt_tokens("gpt-4.1-mini", messages) == (
+        litellm.token_counter(model="gpt-4.1-mini", messages=TEXT_ONLY_MESSAGES) + high_detail_image_token_upper_bound()
+    )
+
+
+@pytest.mark.parametrize("scheme", ["HTTPS://", "Http://"])
+def test_count_relayed_prompt_tokens_charges_an_uppercase_scheme_remote_high_detail_image_at_the_upper_bound(scheme):
+    messages = _image_messages(scheme + UNREACHABLE_IMAGE_URL.split("://", 1)[1], "high")
+
+    assert count_relayed_prompt_tokens("gpt-4.1-mini", messages) == (
+        litellm.token_counter(model="gpt-4.1-mini", messages=TEXT_ONLY_MESSAGES) + high_detail_image_token_upper_bound()
+    )
diff --git a/tests/test_litellm/proxy/pass_through_endpoints/test_llm_pass_through_endpoints.py b/tests/test_litellm/proxy/pass_through_endpoints/test_llm_pass_through_endpoints.py
index d9969dd1dc9..addc952af14 100644
--- a/tests/test_litellm/proxy/pass_through_endpoints/test_llm_pass_through_endpoints.py
+++ b/tests/test_litellm/proxy/pass_through_endpoints/test_llm_pass_through_endpoints.py
@@ -1,3 +1,4 @@
+import asyncio
 import base64
 import contextlib
 import json
@@ -19,6 +20,7 @@ from starlette.datastructures import FormData
 
 import litellm
 from litellm.proxy.common_request_processing import ProxyBaseLLMRequestProcessing
+from tests.test_litellm.llms.bedrock.event_loop_probe import EventLoopProbe
 from litellm.constants import LITELLM_PROXY_MASTER_KEY_ALIAS
 from litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints import (
     BaseOpenAIPassThroughHandler,
@@ -1852,11 +1854,11 @@ class TestBedrockAgentRuntimePassthroughToggle:
         return request
 
     @contextlib.contextmanager
-    def _patched_dispatch(self, general_settings: Mapping[str, object]):
+    def _patched_dispatch(self, general_settings: Mapping[str, object], credentials: object | None = None):
         from botocore.credentials import Credentials
 
         bedrock_llm: Final = Mock()
-        bedrock_llm.get_credentials = Mock(return_value=Credentials("ak", "sk"))
+        bedrock_llm.get_credentials = Mock(return_value=credentials or Credentials("ak", "sk"))
         forwarder: Final = AsyncMock(return_value="forwarded")
 
         with (
@@ -1891,6 +1893,27 @@ class TestBedrockAgentRuntimePassthroughToggle:
         forwarder.assert_awaited_once()
         assert "bedrock-agent-runtime.us-east-1.amazonaws.com" in create_route.call_args.kwargs["target"]
 
+    @pytest.mark.asyncio
+    async def test_agent_runtime_dispatch_signs_off_the_event_loop(self, monkeypatch):
+        """Regression for issue #40165: the agent-runtime pass-through signed on the loop, so botocore's
+        blocking credential refresh inside SigV4 stalled every other request on the worker."""
+        monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+        probe: Final = EventLoopProbe()
+        release: Final = asyncio.create_task(probe.release_refresh_from_the_loop())
+
+        with self._patched_dispatch(MappingProxyType({}), credentials=probe.credentials()) as (create_route, forwarder):
+            result: Final = await bedrock_proxy_route(
+                endpoint=self.AGENT_RUNTIME_ENDPOINT,
+                request=self._mock_request(),
+                fastapi_response=Mock(),
+                user_api_key_dict=UserAPIKeyAuth(),
+            )
+        await release
+
+        assert result == "forwarded"
+        assert create_route.call_args.kwargs["custom_headers"]["Authorization"].startswith("AWS4-HMAC-SHA256")
+        assert probe.served_during_refresh is True
+
     @pytest.mark.asyncio
     @pytest.mark.parametrize("value", (True, "true", "True"))
     async def test_agent_runtime_dispatch_rejected_when_disabled(self, value: bool | str):
@@ -4999,7 +5022,11 @@ class TestPassthroughRouterModelBudgetReservation:
 
         monkeypatch.setattr(proxy_server, "llm_router", RecordingRouter())
         monkeypatch.setattr(ep, "get_request_body", fake_get_request_body)
-        monkeypatch.setattr(ep, "is_passthrough_request_using_router_model", lambda *a, **k: True)
+        monkeypatch.setattr(
+            ep,
+            "is_passthrough_request_using_router_model",
+            lambda request_body, llm_router=None: request_body.get("model") in ("gpt-5", "router-model"),
+        )
         return captured
 
     def _assert_metadata_carries_attribution(self, captured: list[dict], user_api_key_dict: UserAPIKeyAuth) -> None:
@@ -5098,7 +5125,11 @@ class TestAzureRouterModelStreamingDispatch:
 
         monkeypatch.setattr(proxy_server, "llm_router", StreamingRouter())
         monkeypatch.setattr(ep, "get_request_body", fake_get_request_body)
-        monkeypatch.setattr(ep, "is_passthrough_request_using_router_model", lambda *a, **k: True)
+        monkeypatch.setattr(
+            ep,
+            "is_passthrough_request_using_router_model",
+            lambda request_body, llm_router=None: request_body.get("model") in ("gpt-5", "router-model"),
+        )
 
         request = MagicMock(spec=Request)
         request.method = "POST"
@@ -5158,7 +5189,11 @@ class TestAzureRouterModelStreamingKeepalive:
 
         monkeypatch.setattr(proxy_server, "llm_router", StreamingRouter())
         monkeypatch.setattr(ep, "get_request_body", fake_get_request_body)
-        monkeypatch.setattr(ep, "is_passthrough_request_using_router_model", lambda *a, **k: True)
+        monkeypatch.setattr(
+            ep,
+            "is_passthrough_request_using_router_model",
+            lambda request_body, llm_router=None: request_body.get("model") in ("gpt-5", "router-model"),
+        )
 
         request = MagicMock(spec=Request)
         request.method = "POST"
@@ -5208,6 +5243,97 @@ class TestAzureRouterModelStreamingKeepalive:
         assert chunks == [b"data: hello\n\n"]
 
 
+class TestRouterModelRelayUpstreamContract:
+    def _request(self, content_type: str) -> MagicMock:
+        request = MagicMock(spec=Request)
+        request.method = "POST"
+        request.headers = {"content-type": content_type}
+        request.query_params = {}
+        return request
+
+    def _install_router(self, monkeypatch, router, body: dict) -> None:
+        import litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints as ep
+        import litellm.proxy.proxy_server as proxy_server
+
+        async def fake_get_request_body(_request):
+            return body
+
+        monkeypatch.setattr(proxy_server, "llm_router", router)
+        monkeypatch.setattr(ep, "get_request_body", fake_get_request_body)
+        monkeypatch.setattr(
+            ep,
+            "is_passthrough_request_using_router_model",
+            lambda request_body, llm_router=None: request_body.get("model") in ("gpt-5", "router-model"),
+        )
+
+    def _recording_router(self, captured: list[dict]):
+        class RecordingRouter:
+            async def allm_passthrough_route(self, **kwargs):
+                captured.append(kwargs)
+                return httpx.Response(200, json={"ok": True})
+
+        return RecordingRouter()
+
+    @pytest.mark.asyncio
+    async def test_azure_relay_keeps_the_json_body_when_the_content_type_carries_a_charset(self, monkeypatch):
+        body = {"model": "gpt-5", "messages": [{"role": "user", "content": "hi"}]}
+        captured: list[dict] = []
+        self._install_router(monkeypatch, self._recording_router(captured), body)
+
+        await azure_proxy_route(
+            endpoint="openai/deployments/gpt-5/chat/completions",
+            request=self._request("application/json; charset=utf-8"),
+            fastapi_response=MagicMock(spec=Response),
+            user_api_key_dict=UserAPIKeyAuth(api_key="hashed-token"),
+        )
+
+        assert captured[0]["json"] == body
+
+    @pytest.mark.asyncio
+    async def test_vllm_relay_keeps_the_json_body_when_the_content_type_carries_a_charset(self, monkeypatch):
+        body = {"model": "router-model", "messages": [{"role": "user", "content": "hi"}]}
+        captured: list[dict] = []
+        self._install_router(monkeypatch, self._recording_router(captured), body)
+
+        await vllm_proxy_route(
+            endpoint="/chat/completions",
+            request=self._request("application/json; charset=utf-8"),
+            fastapi_response=MagicMock(spec=Response),
+            user_api_key_dict=UserAPIKeyAuth(api_key="hashed-token"),
+        )
+
+        assert captured[0]["json"] == body
+
+    @pytest.mark.asyncio
+    async def test_azure_relay_returns_the_upstream_status_and_body_when_the_deployment_rejects_the_call(
+        self, monkeypatch
+    ):
+        upstream_body = {"error": {"code": "DeploymentNotFound", "message": "The API deployment does not exist."}}
+
+        class RejectingRouter:
+            async def allm_passthrough_route(self, **kwargs):
+                upstream_request = httpx.Request(
+                    "POST", "https://my-azure.openai.azure.com/openai/deployments/gpt-5/chat/completions"
+                )
+                upstream = httpx.Response(
+                    404, json=upstream_body, headers={"x-ms-request-id": "req-1"}, request=upstream_request
+                )
+                raise httpx.HTTPStatusError("404", request=upstream_request, response=upstream)
+
+        self._install_router(monkeypatch, RejectingRouter(), {"model": "gpt-5", "stream": False})
+
+        result = await azure_proxy_route(
+            endpoint="openai/deployments/gpt-5/chat/completions",
+            request=self._request("application/json"),
+            fastapi_response=MagicMock(spec=Response),
+            user_api_key_dict=UserAPIKeyAuth(api_key="hashed-token"),
+        )
+
+        assert result.status_code == 404
+        assert json.loads(result.body) == upstream_body
+        assert result.headers["x-ms-request-id"] == "req-1"
+
+
 @pytest.mark.asyncio
 async def test_bedrock_count_tokens_error_forwards_provider_headers():
     """The count tokens route converts BedrockError into an HTTPException, and dropping the
@@ -5240,3 +5366,88 @@ async def test_bedrock_count_tokens_error_forwards_provider_headers():
 
     assert exc_info.value.status_code == 500
     assert exc_info.value.headers["llm_provider-x-amzn-requestid"] == "req-count-tokens-500"
+
+
+class _AzureGroupRouter:
+    def __init__(self, captured: list[dict]) -> None:
+        self.captured = captured
+
+    def get_model_names(self, team_id=None):
+        return ["gpt", "other-group"]
+
+    def get_model_list(self, model_name=None, team_id=None):
+        rows = [
+            {"model_name": "gpt", "litellm_params": {"model": "azure_ai/gpt-5.4-mini", "api_key": "k"}},
+            {"model_name": "other-group", "litellm_params": {"model": "azure/gpt-5.4", "api_key": "k"}},
+        ]
+        return [row for row in rows if model_name is None or row["model_name"] == model_name]
+
+    async def allm_passthrough_route(self, **kwargs):
+        self.captured.append(kwargs)
+        return httpx.Response(200, json={"ok": True})
+
+
+class TestAzureRelayDeploymentSegment:
+    """A key allowed one model group must not reach another deployment by naming it in the
+    ``openai/deployments/<x>`` segment while the group segment picks the credential."""
+
+    def test_models_served_by_group_resolves_each_deployment_to_its_model_name(self):
+        from litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints import _models_served_by_group
+
+        assert _models_served_by_group(_AzureGroupRouter([]), "gpt") == frozenset({"gpt-5.4-mini"})
+        assert _models_served_by_group(_AzureGroupRouter([]), "missing-group") == frozenset()
+
+    def _install(self, monkeypatch, body: dict) -> list[dict]:
+        import litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints as ep
+        import litellm.proxy.proxy_server as proxy_server
+
+        captured: list[dict] = []
+
+        async def fake_get_request_body(_request):
+            return body
+
+        monkeypatch.setattr(proxy_server, "llm_router", _AzureGroupRouter(captured))
+        monkeypatch.setattr(ep, "get_request_body", fake_get_request_body)
+        return captured
+
+    def _request(self) -> Request:
+        request = MagicMock(spec=Request)
+        request.method = "POST"
+        request.headers = {"content-type": "application/json"}
+        request.query_params = {}
+        return request
+
+    @pytest.mark.asyncio
+    async def test_azure_relay_rejects_a_deployment_the_group_does_not_serve(self, monkeypatch):
+        from fastapi import HTTPException
+
+        captured = self._install(monkeypatch, {"model": "gpt", "messages": []})
+
+        with pytest.raises(HTTPException) as exc_info:
+            await azure_proxy_route(
+                endpoint="gpt/openai/deployments/gpt-5.4/chat/completions",
+                request=self._request(),
+                fastapi_response=MagicMock(spec=Response),
+                user_api_key_dict=UserAPIKeyAuth(api_key="hashed-token", models=["gpt"]),
+            )
+
+        assert exc_info.value.status_code == 400
+        assert "gpt-5.4" in exc_info.value.detail["error"]
+        assert captured == []
+
+    @pytest.mark.asyncio
+    async def test_azure_relay_dispatches_the_group_and_its_own_deployment_name(self, monkeypatch):
+        captured = self._install(monkeypatch, {"model": "gpt", "messages": []})
+
+        for endpoint in (
+            "gpt/openai/deployments/gpt/chat/completions",
+            "gpt/openai/deployments/gpt-5.4-mini/chat/completions",
+        ):
+            await azure_proxy_route(
+                endpoint=endpoint,
+                request=self._request(),
+                fastapi_response=MagicMock(spec=Response),
+                user_api_key_dict=UserAPIKeyAuth(api_key="hashed-token", models=["gpt"]),
+            )
+
+        assert [call["model"] for call in captured] == ["gpt", "gpt"]
diff --git a/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py b/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py
index 61880a8c6f6..0a2641082dc 100644
--- a/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py
+++ b/tests/test_litellm/proxy/policy_engine/test_pipeline_executor.py
@@ -675,8 +675,6 @@ async def test_guardrail_not_found_uses_on_fail(monkeypatch):
         ],
     )
 
-    monkeypatch.setattr(litellm, "callbacks", [])
-
     result = await PipelineExecutor.execute_steps(
         steps=pipeline.steps,
         mode=pipeline.mode,
@@ -1065,7 +1063,7 @@ class _TextReturningGuardrail(CustomGuardrail):
 
 
 class _TextTranslation:
-    delivers_ended_stream_text_rewrites = False
+    delivers_ended_stream_rewrites = False
 
     def __init__(self):
         self.seen_guardrail_names = []
@@ -1087,7 +1085,7 @@ class _WritingTranslation:
     """Writes the guardrail's text (and tool-call) outputs back into the buffered chunks the way the
     chat/Responses/Messages handlers do on an ended stream."""
 
-    delivers_ended_stream_text_rewrites = True
+    delivers_ended_stream_rewrites = True
 
     async def process_output_streaming_response(
         self,
@@ -1106,12 +1104,13 @@ class _WritingTranslation:
             logging_obj=litellm_logging_obj,
         )
         responses_so_far[0]["text"] = outputs["texts"][0]
-        responses_so_far[0]["tool_call"] = outputs["tool_calls"][0]
+        if len(outputs["tool_calls"]) == 1:
+            responses_so_far[0]["tool_call"] = outputs["tool_calls"][0]
         return responses_so_far
 
 
 class _RefusingTranslation:
-    delivers_ended_stream_text_rewrites = True
+    delivers_ended_stream_rewrites = True
 
     async def process_output_streaming_response(
         self,
@@ -1148,6 +1147,7 @@ def _assert_passed_with_discard_warning(result, caplog):
     assert result.terminal_action == "allow"
     assert [step.outcome for step in result.step_results] == ["pass"]
     assert any("'masker'" in record.getMessage() and "discarded" in record.getMessage() for record in caplog.records)
+    assert "masker" not in ((result.modified_data or {}).get("metadata") or {}).get("applied_guardrails", [])
 
 
 @pytest.mark.asyncio
@@ -1229,13 +1229,47 @@ async def test_streaming_step_delivers_text_rewrite_through_writing_translation(
 
 
 @pytest.mark.asyncio
-async def test_streaming_step_discards_tool_call_rewrite_and_restores_written_text(monkeypatch, caplog):
+async def test_streaming_step_delivers_tool_call_rewrite_through_writing_translation(monkeypatch, caplog):
     monkeypatch.setattr(litellm, "callbacks", [_TextAndToolCallRewritingGuardrail(rewrite_tool_call=True)])
     chunks = [_chunk()]
 
     with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
         result = await _run_streaming_step(_WritingTranslation(), chunks)
 
+    assert result.terminal_action == "allow"
+    assert chunks[0]["text"] == "hello [MASKED]"
+    assert chunks[0]["tool_call"]["function"]["arguments"] == '{"ssn": "[MASKED]"}'
+    assert not any("discarded" in record.getMessage() for record in caplog.records)
+
+
+class _ToolCallDroppingGuardrail(CustomGuardrail):
+    def __init__(self):
+        super().__init__(guardrail_name="masker", event_hook="post_call", default_on=True)
+
+    async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+        return {**inputs, "texts": ["hello [MASKED]"], "tool_calls": []}
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_whole_rewrite_when_guardrail_drops_a_tool_call(monkeypatch, caplog):
+    monkeypatch.setattr(litellm, "callbacks", [_ToolCallDroppingGuardrail()])
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_streaming_step(_WritingTranslation(), chunks)
+
+    _assert_passed_with_discard_warning(result, caplog)
+    assert chunks == [_chunk()]
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_tool_call_rewrite_when_translation_lacks_write_back(monkeypatch, caplog):
+    monkeypatch.setattr(litellm, "callbacks", [_TextAndToolCallRewritingGuardrail(rewrite_tool_call=True)])
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_streaming_step(_TextTranslation(), chunks)
+
     _assert_passed_with_discard_warning(result, caplog)
     assert chunks == [_chunk()]
 
@@ -1294,3 +1328,350 @@ async def test_streaming_step_restores_chunks_when_translation_refuses_the_rewri
 
     _assert_passed_with_discard_warning(result, caplog)
     assert chunks == [_chunk()]
+
+
+class _LegacyHookGuardrail(CustomGuardrail):
+    """A guardrail with only the legacy post-call hook: it never defines apply_guardrail."""
+
+    def __init__(self, replacement=None, raises=None, guardrail_name="masker", rewrite_in_place=None):
+        super().__init__(guardrail_name=guardrail_name, event_hook="post_call", default_on=True)
+        self.replacement = replacement
+        self.raises = raises
+        self.rewrite_in_place = rewrite_in_place
+        self.calls = []
+
+    async def async_post_call_success_hook(self, data, user_api_key_dict, response):
+        self.calls.append({"data": data, "user_api_key_dict": user_api_key_dict, "response": response})
+        if self.raises is not None:
+            raise self.raises
+        if self.rewrite_in_place is not None:
+            response["text"] = self.rewrite_in_place
+        return self.replacement
+
+
+class _NativeHooksGuardrail(_LegacyHookGuardrail):
+    use_native_lifecycle_hooks = True
+
+    async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+        raise AssertionError("a guardrail that keeps its native hooks never runs apply_guardrail")
+
+
+class _LegacyScanningTranslation:
+    """Stores the assembled response under request_data["response"] before scanning, like the
+    chat, Responses, and Messages handlers, hands hooks a route-native shape, and re-extracts one
+    text per entry of a replacement's "texts"."""
+
+    delivers_ended_stream_rewrites = True
+
+    def post_call_hook_response(self, response):
+        return {"native": True, "text": response["text"], "tool_calls": response["tool_calls"]}
+
+    async def process_output_streaming_response(
+        self,
+        responses_so_far,
+        guardrail_to_apply,
+        litellm_logging_obj=None,
+        user_api_key_dict=None,
+        request_data=None,
+        deliver_ended_stream_rewrites=False,
+    ):
+        request_data.setdefault(
+            "response", {"text": responses_so_far[0]["text"], "tool_calls": [dict(responses_so_far[0]["tool_call"])]}
+        )
+        outputs = await guardrail_to_apply.apply_guardrail(
+            inputs={"texts": [responses_so_far[0]["text"]], "tool_calls": [dict(responses_so_far[0]["tool_call"])]},
+            request_data=request_data,
+            input_type="response",
+            logging_obj=litellm_logging_obj,
+        )
+        responses_so_far[0]["text"] = outputs["texts"][0]
+        return responses_so_far
+
+    async def process_output_response(
+        self, response, guardrail_to_apply, litellm_logging_obj=None, user_api_key_dict=None, request_data=None
+    ):
+        inputs = {"texts": [response["text"]] if "text" in response else list(response["texts"])}
+        if response.get("tool_calls"):
+            inputs["tool_calls"] = list(response["tool_calls"])
+        await guardrail_to_apply.apply_guardrail(
+            inputs=inputs,
+            request_data={"response": response},
+            input_type="response",
+            logging_obj=litellm_logging_obj,
+        )
+        return response
+
+
+class _ToolOnlyLegacyScanningTranslation(_LegacyScanningTranslation):
+    """Like the Messages handler on a tool-only message: the ended-stream scan omits "texts" from
+    the inputs, while the non-streaming scan of the same response sends an empty list."""
+
+    async def process_output_streaming_response(
+        self,
+        responses_so_far,
+        guardrail_to_apply,
+        litellm_logging_obj=None,
+        user_api_key_dict=None,
+        request_data=None,
+        deliver_ended_stream_rewrites=False,
+    ):
+        request_data.setdefault("response", {"text": "", "tool_calls": [dict(responses_so_far[0]["tool_call"])]})
+        await guardrail_to_apply.apply_guardrail(
+            inputs={"tool_calls": [dict(responses_so_far[0]["tool_call"])]},
+            request_data=request_data,
+            input_type="response",
+            logging_obj=litellm_logging_obj,
+        )
+        return responses_so_far
+
+    async def process_output_response(
+        self, response, guardrail_to_apply, litellm_logging_obj=None, user_api_key_dict=None, request_data=None
+    ):
+        await guardrail_to_apply.apply_guardrail(
+            inputs={"texts": [], "tool_calls": list(response.get("tool_calls") or [])},
+            request_data={"response": response},
+            input_type="response",
+            logging_obj=litellm_logging_obj,
+        )
+        return response
+
+
+def _tool_only_chunk():
+    return {"text": "", "tool_call": _chunk()["tool_call"]}
+
+
+def _native(text):
+    return {"native": True, "text": text, "tool_calls": [_chunk()["tool_call"]]}
+
+
+def _legacy_replacement(*texts, tool_calls=None):
+    return {"texts": list(texts), "tool_calls": [_chunk()["tool_call"]] if tool_calls is None else tool_calls}
+
+
+async def _run_legacy_streaming_step(
+    monkeypatch, guardrail, chunks, on_fail="block", on_error="next", translation=None
+):
+    return await _run_legacy_streaming_steps(
+        monkeypatch, [guardrail], chunks, on_fail=on_fail, on_error=on_error, translation=translation
+    )
+
+
+async def _run_legacy_streaming_steps(
+    monkeypatch, guardrails, chunks, on_fail="block", on_error="next", translation=None
+):
+    monkeypatch.setattr(litellm, "callbacks", list(guardrails))
+    return await PipelineExecutor.execute_steps(
+        steps=[
+            PipelineStep(
+                guardrail=guardrail.guardrail_name,
+                on_pass="next" if position + 1 < len(guardrails) else "allow",
+                on_fail=on_fail,
+                on_error=on_error,
+            )
+            for position, guardrail in enumerate(guardrails)
+        ],
+        mode="post_call",
+        data={"model": "m"},
+        user_api_key_dict=MagicMock(),
+        call_type="completion",
+        policy_name="p",
+        streaming_chunks=chunks,
+        endpoint_translation=_LegacyScanningTranslation() if translation is None else translation,
+    )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("guardrail_class", [_LegacyHookGuardrail, _NativeHooksGuardrail])
+async def test_streaming_step_runs_legacy_hook_and_delivers_its_rewrite(monkeypatch, caplog, guardrail_class):
+    guardrail = guardrail_class(replacement=_legacy_replacement("[REWRITTEN] hello world"))
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks)
+
+    assert result.terminal_action == "allow"
+    assert [step.outcome for step in result.step_results] == ["pass"]
+    assert chunks[0]["text"] == "[REWRITTEN] hello world"
+    assert [call["response"] for call in guardrail.calls] == [_native("hello world")]
+    assert guardrail.calls[0]["data"]["model"] == "m"
+    assert result.modified_data["metadata"]["applied_guardrails"] == ["masker"]
+    assert not any("discarded" in record.getMessage() for record in caplog.records)
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_delivers_a_legacy_rewrite_made_in_place(monkeypatch, caplog):
+    guardrail = _LegacyHookGuardrail(rewrite_in_place="[REWRITTEN] hello world")
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks)
+
+    assert result.terminal_action == "allow"
+    assert [step.outcome for step in result.step_results] == ["pass"]
+    assert chunks[0]["text"] == "[REWRITTEN] hello world"
+    assert not any("discarded" in record.getMessage() for record in caplog.records)
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_passes_untouched_when_legacy_hook_returns_none(monkeypatch, caplog):
+    guardrail = _LegacyHookGuardrail(replacement=None)
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks)
+
+    assert result.terminal_action == "allow"
+    assert len(guardrail.calls) == 1
+    assert chunks == [_chunk()]
+    assert not any("discarded" in record.getMessage() for record in caplog.records)
+
+
+@pytest.mark.skipif(HTTPException is None, reason="fastapi not installed")
+@pytest.mark.asyncio
+async def test_streaming_step_blocks_with_the_legacy_hook_exception(monkeypatch):
+    exc = HTTPException(status_code=400, detail={"error": "output blocked"})
+    chunks = [_chunk()]
+
+    result = await _run_legacy_streaming_step(monkeypatch, _LegacyHookGuardrail(raises=exc), chunks)
+
+    assert result.terminal_action == "block"
+    assert [step.outcome for step in result.step_results] == ["fail"]
+    assert result.original_exception is exc
+    assert chunks == [_chunk()]
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_takes_on_error_when_legacy_hook_crashes(monkeypatch):
+    chunks = [_chunk()]
+
+    result = await _run_legacy_streaming_step(
+        monkeypatch, _LegacyHookGuardrail(raises=ValueError("boom")), chunks, on_error="block"
+    )
+
+    assert result.terminal_action == "block"
+    assert [step.outcome for step in result.step_results] == ["error"]
+    assert result.step_results[0].error_detail == "boom"
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_legacy_rewrite_whose_texts_do_not_line_up(monkeypatch, caplog):
+    guardrail = _LegacyHookGuardrail(replacement=_legacy_replacement("split", "in two"))
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks)
+
+    _assert_passed_with_discard_warning(result, caplog)
+    assert chunks == [_chunk()]
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_legacy_rewrite_that_changes_a_tool_call(monkeypatch, caplog):
+    masked_tool_call = {"function": {"name": "lookup", "arguments": '{"ssn": "[MASKED]"}'}}
+    guardrail = _LegacyHookGuardrail(
+        replacement=_legacy_replacement("[REWRITTEN] hello world", tool_calls=[masked_tool_call])
+    )
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks)
+
+    _assert_passed_with_discard_warning(result, caplog)
+    assert chunks == [_chunk()]
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_legacy_rewrite_that_drops_the_tool_calls(monkeypatch, caplog):
+    guardrail = _LegacyHookGuardrail(replacement=_legacy_replacement("[REWRITTEN] hello world", tool_calls=[]))
+    chunks = [_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks)
+
+    _assert_passed_with_discard_warning(result, caplog)
+    assert chunks == [_chunk()]
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_passes_a_tool_only_stream_the_legacy_hook_left_alone(monkeypatch, caplog):
+    guardrail = _LegacyHookGuardrail(replacement=None)
+    chunks = [_tool_only_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(
+            monkeypatch, guardrail, chunks, translation=_ToolOnlyLegacyScanningTranslation()
+        )
+
+    assert result.terminal_action == "allow"
+    assert [step.outcome for step in result.step_results] == ["pass"]
+    assert result.modified_data["metadata"]["applied_guardrails"] == ["masker"]
+    assert chunks == [_tool_only_chunk()]
+    assert not any("discarded" in record.getMessage() for record in caplog.records)
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_a_legacy_tool_call_rewrite_on_a_tool_only_stream(monkeypatch, caplog):
+    masked_tool_call = {"function": {"name": "lookup", "arguments": '{"ssn": "[MASKED]"}'}}
+    guardrail = _LegacyHookGuardrail(replacement=_legacy_replacement(tool_calls=[masked_tool_call]))
+    chunks = [_tool_only_chunk()]
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        result = await _run_legacy_streaming_step(
+            monkeypatch, guardrail, chunks, translation=_ToolOnlyLegacyScanningTranslation()
+        )
+
+    _assert_passed_with_discard_warning(result, caplog)
+    assert chunks == [_tool_only_chunk()]
+
+
+class _NoHooksGuardrail(CustomGuardrail):
+    pass
+
+
+class _IteratorAndLegacyHookGuardrail(_LegacyHookGuardrail):
+    async def async_post_call_streaming_iterator_hook(self, user_api_key_dict, response, request_data):
+        async for item in response:
+            yield item
+
+
+class _UnscannableRewriteTranslation(_LegacyScanningTranslation):
+    """Like the chat handler on a response whose choices are plain dicts: the non-streaming scan
+    never hands anything to the guardrail."""
+
+    async def process_output_response(
+        self, response, guardrail_to_apply, litellm_logging_obj=None, user_api_key_dict=None, request_data=None
+    ):
+        return response
+
+
+def test_streaming_execution_runs_legacy_hooks_only_when_that_hook_is_their_only_streaming_path():
+    assert PipelineExecutor.supports_streaming_execution(_LegacyHookGuardrail()) is True
+    assert PipelineExecutor.supports_streaming_execution(_NativeHooksGuardrail()) is True
+    assert PipelineExecutor.supports_streaming_execution(_IteratorAndLegacyHookGuardrail()) is False
+    assert PipelineExecutor.supports_streaming_execution(_NoHooksGuardrail(guardrail_name="neither")) is False
+
+
+@pytest.mark.asyncio
+async def test_streaming_step_discards_a_legacy_rewrite_the_translation_cannot_rescan(monkeypatch, caplog):
+    guardrail = _LegacyHookGuardrail(replacement=_legacy_replacement("hello [MASKED]"))
+    chunks = [_chunk()]
+
+    result = await _run_legacy_streaming_step(monkeypatch, guardrail, chunks, translation=_UnscannableRewriteTranslation())
+
+    _assert_passed_with_discard_warning(result, caplog)
+    assert chunks == [_chunk()]
+
+
+@pytest.mark.asyncio
+async def test_later_legacy_step_sees_the_stream_as_the_earlier_step_left_it(monkeypatch):
+    masker = _LegacyHookGuardrail(replacement=_legacy_replacement("[REWRITTEN] hello world"))
+    auditor = _LegacyHookGuardrail(replacement=None, guardrail_name="auditor")
+    chunks = [_chunk()]
+
+    result = await _run_legacy_streaming_steps(monkeypatch, [masker, auditor], chunks, on_fail="next")
+
+    assert result.terminal_action == "allow"
+    assert [step.outcome for step in result.step_results] == ["pass", "pass"]
+    assert chunks[0]["text"] == "[REWRITTEN] hello world"
+    assert [call["response"] for call in masker.calls] == [_native("hello world")]
+    assert [call["response"] for call in auditor.calls] == [_native("[REWRITTEN] hello world")]
diff --git a/tests/test_litellm/proxy/policy_engine/test_response_retrieval.py b/tests/test_litellm/proxy/policy_engine/test_response_retrieval.py
new file mode 100644
index 00000000000..37849101b3a
--- /dev/null
+++ b/tests/test_litellm/proxy/policy_engine/test_response_retrieval.py
@@ -0,0 +1,262 @@
+import logging
+from collections.abc import Iterator, Mapping
+
+import pytest
+
+from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy.policy_engine.attachment_registry import get_attachment_registry
+from litellm.proxy.policy_engine.policy_registry import get_policy_registry
+from litellm.proxy.policy_engine.response_retrieval import attach_post_call_pipelines_to_retrieval
+from litellm.responses.utils import ResponsesAPIRequestUtils
+from litellm.types.router import Deployment, LiteLLM_Params
+
+GOVERNED_MODEL_GROUP = "gpt-5.4-mini"
+GOVERNED_MODEL_ID = "deployment-governed"
+UNGOVERNED_MODEL_GROUP = "gpt-4.1-mini"
+UNGOVERNED_MODEL_ID = "deployment-ungoverned"
+WILDCARD_MODEL_GROUP = "openai/*"
+WILDCARD_MODEL_ID = "deployment-wildcard"
+
+
+class FakeRouter:
+    def __init__(self, deployments: dict[str, Deployment], model_group_alias: dict[str, object] | None = None):
+        self._deployments = deployments
+        self.model_group_alias = model_group_alias or {}
+
+    def get_deployment(self, model_id: str) -> Deployment | None:
+        return self._deployments.get(model_id)
+
+
+def _deployment(model_group: str, model_id: str) -> Deployment:
+    return Deployment(
+        model_name=model_group,
+        litellm_params=LiteLLM_Params(model=f"openai/{model_group}"),
+        model_info={"id": model_id},
+    )
+
+
+def _router(model_group_alias: dict[str, object] | None = None) -> FakeRouter:
+    return FakeRouter(
+        {
+            GOVERNED_MODEL_ID: _deployment(GOVERNED_MODEL_GROUP, GOVERNED_MODEL_ID),
+            UNGOVERNED_MODEL_ID: _deployment(UNGOVERNED_MODEL_GROUP, UNGOVERNED_MODEL_ID),
+            WILDCARD_MODEL_ID: _deployment(WILDCARD_MODEL_GROUP, WILDCARD_MODEL_ID),
+        },
+        model_group_alias,
+    )
+
+
+def _encoded_response_id(model_id: str) -> str:
+    return ResponsesAPIRequestUtils._build_responses_api_response_id(
+        custom_llm_provider="openai", model_id=model_id, response_id="resp_upstream"
+    )
+
+
+def _pipeline_policy(guardrail: str, mode: str = "post_call") -> dict[str, object]:
+    return {
+        "guardrails": {"add": [guardrail]},
+        "pipeline": {"mode": mode, "steps": [{"guardrail": guardrail, "on_pass": "allow", "on_fail": "block"}]},
+    }
+
+
+@pytest.fixture
+def policy_engine() -> Iterator[None]:
+    policy_registry = get_policy_registry()
+    attachment_registry = get_attachment_registry()
+    policy_registry.load_policies(
+        {
+            "response-governance": _pipeline_policy("output-word-filter"),
+            "input-governance": _pipeline_policy("input-word-filter", mode="pre_call"),
+            "team-governance": _pipeline_policy("team-word-filter"),
+            "tag-governance": _pipeline_policy("tag-word-filter"),
+        }
+    )
+    attachment_registry.load_attachments(
+        [
+            {"policy": "response-governance", "models": [GOVERNED_MODEL_GROUP]},
+            {"policy": "input-governance", "models": [GOVERNED_MODEL_GROUP]},
+            {"policy": "team-governance", "teams": ["governed-team"]},
+            {"policy": "tag-governance", "tags": ["governed"]},
+        ]
+    )
+    yield
+    policy_registry.clear()
+    attachment_registry.clear()
+
+
+def _retrieval_data(model_id: str) -> dict[str, object]:
+    return {"response_id": _encoded_response_id(model_id), "litellm_metadata": {}}
+
+
+def _attached_pipelines(data: Mapping[str, object]) -> tuple[tuple[str, str], ...]:
+    bucket = data["litellm_metadata"]
+    assert isinstance(bucket, dict)
+    return tuple(
+        (policy_name, ",".join(step.guardrail for step in pipeline.steps))
+        for policy_name, pipeline in bucket["_guardrail_pipelines"]
+    )
+
+
+def test_attaches_model_scoped_post_call_pipeline_to_retrieval(policy_engine: None) -> None:
+    data = _retrieval_data(GOVERNED_MODEL_ID)
+
+    attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=_router())
+
+    assert _attached_pipelines(data) == (("response-governance", "output-word-filter"),)
+    assert data["litellm_metadata"]["_pipeline_managed_guardrails"] == frozenset({"output-word-filter"})
+    assert data["litellm_metadata"]["applied_policies"] == ["response-governance"]
+    assert data["litellm_metadata"]["applied_guardrails"] == ["output-word-filter"]
+    assert data["litellm_metadata"]["policy_sources"] == {"response-governance": "model:gpt-5.4-mini"}
+    assert "model" not in data
+    assert "guardrails" not in data["litellm_metadata"]
+
+
+def test_key_and_team_context_also_governs_retrieval(policy_engine: None) -> None:
+    data = _retrieval_data(UNGOVERNED_MODEL_ID)
+
+    attach_post_call_pipelines_to_retrieval(
+        data=data, user_api_key_dict=UserAPIKeyAuth(team_alias="governed-team"), llm_router=_router()
+    )
+
+    assert _attached_pipelines(data) == (("team-governance", "team-word-filter"),)
+
+
+def test_tag_attached_policy_is_not_re_matched_when_the_retrieval_carries_no_tag(policy_engine: None) -> None:
+    data = _retrieval_data(GOVERNED_MODEL_ID)
+
+    attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=_router())
+
+    assert _attached_pipelines(data) == (("response-governance", "output-word-filter"),)
+
+
+def test_tag_attached_policy_governs_a_retrieval_whose_metadata_carries_the_tag(policy_engine: None) -> None:
+    data: dict[str, object] = {
+        "response_id": _encoded_response_id(UNGOVERNED_MODEL_ID),
+        "litellm_metadata": {"tags": ["governed"]},
+    }
+
+    attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=_router())
+
+    assert _attached_pipelines(data) == (("tag-governance", "tag-word-filter"),)
+    assert data["litellm_metadata"]["policy_sources"] == {"tag-governance": "tag:governed"}
+
+
+def test_retrieval_of_an_ungoverned_model_attaches_nothing(policy_engine: None) -> None:
+    data = _retrieval_data(UNGOVERNED_MODEL_ID)
+
+    attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=_router())
+
+    assert data == _retrieval_data(UNGOVERNED_MODEL_ID)
+
+
+def test_already_attached_policy_is_not_attached_twice(policy_engine: None) -> None:
+    data = _retrieval_data(GOVERNED_MODEL_ID)
+    router = _router()
+    attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=router)
+
+    attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=router)
+
+    assert _attached_pipelines(data) == (("response-governance", "output-word-filter"),)
+    assert data["litellm_metadata"]["applied_policies"] == ["response-governance"]
+
+
+def _hidden_submit_model_warnings(caplog: pytest.LogCaptureFixture) -> list[str]:
+    return [
+        record.getMessage()
+        for record in caplog.records
+        if record.levelno == logging.WARNING and "the model name it was submitted as" in record.getMessage()
+    ]
+
+
+def test_wildcard_deployment_attaches_nothing_for_the_submitted_model_and_warns(
+    policy_engine: None, caplog: pytest.LogCaptureFixture
+) -> None:
+    data = _retrieval_data(WILDCARD_MODEL_ID)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=_router())
+
+    assert data == _retrieval_data(WILDCARD_MODEL_ID)
+    assert [
+        "as model group openai/* (a wildcard deployment)" in message
+        for message in _hidden_submit_model_warnings(caplog)
+    ] == [True]
+
+
+def test_aliased_model_group_still_attaches_its_own_policies_and_warns(
+    policy_engine: None, caplog: pytest.LogCaptureFixture
+) -> None:
+    data = _retrieval_data(GOVERNED_MODEL_ID)
+    router = _router({"gpt-mini": GOVERNED_MODEL_GROUP, "gpt-hidden": {"model": GOVERNED_MODEL_GROUP, "hidden": True}})
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=router)
+
+    assert _attached_pipelines(data) == (("response-governance", "output-word-filter"),)
+    assert [
+        "(the target of model_group_alias gpt-mini, gpt-hidden)" in message
+        for message in _hidden_submit_model_warnings(caplog)
+    ] == [True]
+
+
+def test_plain_model_group_retrieval_does_not_warn_about_the_submitted_model(
+    policy_engine: None, caplog: pytest.LogCaptureFixture
+) -> None:
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        attach_post_call_pipelines_to_retrieval(
+            data=_retrieval_data(GOVERNED_MODEL_ID),
+            user_api_key_dict=UserAPIKeyAuth(),
+            llm_router=_router({"other-alias": UNGOVERNED_MODEL_GROUP}),
+        )
+
+    assert _hidden_submit_model_warnings(caplog) == []
+
+
+def _ungoverned_retrieval_warnings(caplog: pytest.LogCaptureFixture) -> list[str]:
+    return [
+        record.getMessage()
+        for record in caplog.records
+        if record.levelno == logging.WARNING
+        and "retrieved without its post_call policy pipelines" in record.getMessage()
+    ]
+
+
+@pytest.mark.parametrize(
+    ("response_id", "reason"),
+    [
+        ("resp_plain_upstream_id", "response id names no deployment"),
+        (_encoded_response_id("deployment-missing-from-router"), "deployment no longer in the router"),
+        (None, "response id names no deployment"),
+    ],
+)
+def test_unresolvable_response_id_attaches_nothing_and_warns(
+    policy_engine: None, caplog: pytest.LogCaptureFixture, response_id: str, reason: str
+) -> None:
+    data = {"response_id": response_id, "litellm_metadata": {}}
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=_router())
+
+    assert data == {"response_id": response_id, "litellm_metadata": {}}
+    assert [message.endswith(f"({reason})") for message in _ungoverned_retrieval_warnings(caplog)] == [True]
+
+
+def test_without_a_router_attaches_nothing_and_warns(policy_engine: None, caplog: pytest.LogCaptureFixture) -> None:
+    data = _retrieval_data(GOVERNED_MODEL_ID)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=None)
+
+    assert data == _retrieval_data(GOVERNED_MODEL_ID)
+    assert [message.endswith("(no router)") for message in _ungoverned_retrieval_warnings(caplog)] == [True]
+
+
+def test_without_policy_engine_attaches_nothing_quietly(caplog: pytest.LogCaptureFixture) -> None:
+    get_policy_registry().clear()
+    data = _retrieval_data(GOVERNED_MODEL_ID)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        attach_post_call_pipelines_to_retrieval(data=data, user_api_key_dict=UserAPIKeyAuth(), llm_router=None)
+
+    assert data == _retrieval_data(GOVERNED_MODEL_ID)
+    assert _ungoverned_retrieval_warnings(caplog) == []
diff --git a/tests/test_litellm/proxy/proxy_server/test_background_health.py b/tests/test_litellm/proxy/proxy_server/test_background_health.py
index 990844369f7..d99aa637955 100644
--- a/tests/test_litellm/proxy/proxy_server/test_background_health.py
+++ b/tests/test_litellm/proxy/proxy_server/test_background_health.py
@@ -20,6 +20,7 @@ from unittest.mock import AsyncMock, MagicMock
 import pytest
 
 import litellm.proxy.proxy_server as proxy_server
+from litellm.constants import BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME
 from litellm.proxy.proxy_server import (
     _adaptive_router_flusher_loop,
     _get_endpoint_exception_status,
@@ -111,13 +112,11 @@ async def test_run_direct_health_check_with_instrumentation_returns_results(
         lambda _gs: {},
     )
 
-    healthy, unhealthy, exceptions = (
-        await _run_direct_health_check_with_instrumentation(
-            model_list=[{"model_name": "gpt-4"}],
-            details=False,
-            max_concurrency=1,
-            instrumentation_context={"source": "test"},
-        )
+    healthy, unhealthy, exceptions = await _run_direct_health_check_with_instrumentation(
+        model_list=[{"model_name": "gpt-4"}],
+        details=False,
+        max_concurrency=1,
+        instrumentation_context={"source": "test"},
     )
 
     assert normalize(
@@ -245,6 +244,137 @@ async def test_schedule_background_health_check_db_save_invalid_no_event_loop_ra
         )
 
 
+def _lock_manager(redis_cache, acquired):
+    manager = MagicMock()
+    manager.redis_cache = redis_cache
+    manager.acquire_lock = AsyncMock(return_value=acquired)
+    manager.release_lock = AsyncMock()
+    return manager
+
+
+def _capture_saves(monkeypatch, persisted=True):
+    saves = []
+
+    async def _fake_save(*_args, **kwargs):
+        saves.append(kwargs)
+        return persisted
+
+    import litellm.proxy.health_endpoints._health_endpoints as he
+
+    monkeypatch.setattr(he, "_save_background_health_checks_to_db", _fake_save)
+    return saves
+
+
+def _cancel_during_save(monkeypatch):
+    async def _fake_save(*_args, **_kwargs):
+        raise asyncio.CancelledError()
+
+    import litellm.proxy.health_endpoints._health_endpoints as he
+
+    monkeypatch.setattr(he, "_save_background_health_checks_to_db", _fake_save)
+
+
+def _schedule_with(lock_manager):
+    _schedule_background_health_check_db_save(
+        prisma_client=MagicMock(),
+        shared_health_manager=None,
+        model_list=[],
+        healthy_endpoints=[],
+        unhealthy_endpoints=[],
+        pod_lock_manager=lock_manager,
+        lock_ttl=300,
+    )
+
+
+@pytest.mark.asyncio
+async def test_schedule_background_health_check_db_save_skips_a_window_another_pod_persisted(monkeypatch):
+    saves = _capture_saves(monkeypatch)
+    lock_manager = _lock_manager(redis_cache=MagicMock(), acquired=False)
+
+    _schedule_with(lock_manager)
+    await asyncio.sleep(0)
+
+    assert saves == []
+
+
+@pytest.mark.asyncio
+async def test_schedule_background_health_check_db_save_holds_the_window_lock_for_the_whole_interval(monkeypatch):
+    """The lock is the "saved this window" marker: never reentrant, TTL = interval, and never released."""
+    saves = _capture_saves(monkeypatch)
+    lock_manager = _lock_manager(redis_cache=MagicMock(), acquired=True)
+
+    _schedule_with(lock_manager)
+    await asyncio.sleep(0)
+
+    assert normalize(
+        {
+            "saves": len(saves),
+            "lock_request": lock_manager.acquire_lock.await_args.kwargs,
+            "released": lock_manager.release_lock.await_count,
+        }
+    ) == {
+        "saves": 1,
+        "lock_request": {
+            "cronjob_id": BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME,
+            "ttl": 300,
+            "allow_reentrant": False,
+        },
+        "released": 0,
+    }
+
+
+@pytest.mark.asyncio
+async def test_schedule_background_health_check_db_save_releases_the_window_lock_when_the_save_reports_failure(
+    monkeypatch,
+):
+    """A failed save must not burn the window: release the lock so another pod's cycle can retry."""
+    saves = _capture_saves(monkeypatch, persisted=False)
+    lock_manager = _lock_manager(redis_cache=MagicMock(), acquired=True)
+
+    _schedule_with(lock_manager)
+    await asyncio.sleep(0)
+
+    assert normalize(
+        {
+            "saves": len(saves),
+            "release_request": lock_manager.release_lock.await_args.kwargs,
+            "release_count": lock_manager.release_lock.await_count,
+        }
+    ) == {
+        "saves": 1,
+        "release_request": {"cronjob_id": BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME},
+        "release_count": 1,
+    }
+
+
+@pytest.mark.asyncio
+async def test_schedule_background_health_check_db_save_releases_the_window_lock_when_the_save_is_cancelled(
+    monkeypatch,
+):
+    """A pod shutting down mid-save releases the lock instead of holding it until the TTL."""
+    _cancel_during_save(monkeypatch)
+    lock_manager = _lock_manager(redis_cache=MagicMock(), acquired=True)
+
+    _schedule_with(lock_manager)
+    await asyncio.sleep(0)
+
+    assert (
+        lock_manager.release_lock.await_args.kwargs,
+        lock_manager.release_lock.await_count,
+    ) == ({"cronjob_id": BACKGROUND_HEALTH_CHECK_DB_SAVE_JOB_NAME}, 1)
+
+
+@pytest.mark.asyncio
+async def test_schedule_background_health_check_db_save_runs_ungated_without_redis(monkeypatch):
+    saves = _capture_saves(monkeypatch, persisted=False)
+    lock_manager = _lock_manager(redis_cache=None, acquired=True)
+
+    _schedule_with(lock_manager)
+    await asyncio.sleep(0)
+
+    assert (len(saves), lock_manager.acquire_lock.await_count, lock_manager.release_lock.await_count) == (1, 0, 0)
+
+
 # ---------------------------------------------------------------------------
 # _get_endpoint_exception_status
 # ---------------------------------------------------------------------------
@@ -319,13 +449,9 @@ def test_write_health_state_to_router_cache_sets_states(monkeypatch):
 
     _write_health_state_to_router_cache(healthy, unhealthy, exceptions)
 
-    fake_router.health_state_cache.set_deployment_health_states.assert_called_once_with(
-        fake_states
-    )
+    fake_router.health_state_cache.set_deployment_health_states.assert_called_once_with(fake_states)
 
-    call_args = fake_router.health_state_cache.set_deployment_health_states.call_args[
-        0
-    ][0]
+    call_args = fake_router.health_state_cache.set_deployment_health_states.call_args[0][0]
     assert normalize(
         {
             "states_keys": sorted(call_args.keys()),
@@ -367,9 +493,7 @@ def test_write_health_state_to_router_cache_populates_for_listing_filter(monkeyp
     fake_router.cooldown_time = 30
 
     monkeypatch.setattr(proxy_server, "llm_router", fake_router)
-    monkeypatch.setattr(
-        proxy_server, "general_settings", {"model_list_healthy_only": True}
-    )
+    monkeypatch.setattr(proxy_server, "general_settings", {"model_list_healthy_only": True})
 
     fake_states = {"m1": {"is_healthy": True}, "m2": {"is_healthy": False}}
 
@@ -403,9 +527,7 @@ def test_write_health_state_to_router_cache_populates_for_listing_filter(monkeyp
         {"m2": SimpleNamespace(status_code=500)},
     )
 
-    fake_router.health_state_cache.set_deployment_health_states.assert_called_once_with(
-        fake_states
-    )
+    fake_router.health_state_cache.set_deployment_health_states.assert_called_once_with(fake_states)
     assert cooldowns == []
     assert failures == []
 
@@ -415,9 +537,7 @@ def test_write_health_state_to_router_cache_swallows_internal_failures(monkeypat
     fake_router = MagicMock()
     fake_router.enable_health_check_routing = True
     fake_router.health_check_ignore_transient_errors = False
-    fake_router.health_state_cache.set_deployment_health_states.side_effect = (
-        RuntimeError("cache exploded")
-    )
+    fake_router.health_state_cache.set_deployment_health_states.side_effect = RuntimeError("cache exploded")
 
     monkeypatch.setattr(proxy_server, "llm_router", fake_router)
 
@@ -447,9 +567,7 @@ async def test_adaptive_router_flusher_loop_flushes_each_router(monkeypatch):
     from litellm.types.router import TaggedPreRoutingStrategy
 
     fake_router = MagicMock()
-    fake_router.adaptive_routers = {
-        "alpha": [TaggedPreRoutingStrategy(tags=(), strategy=fake_ar)]
-    }
+    fake_router.adaptive_routers = {"alpha": [TaggedPreRoutingStrategy(tags=(), strategy=fake_ar)]}
 
     monkeypatch.setattr(proxy_server, "llm_router", fake_router)
     monkeypatch.setattr(proxy_server, "prisma_client", MagicMock())
@@ -547,12 +665,8 @@ async def test_run_background_health_check_runs_one_cycle_then_cancels(monkeypat
         "_run_direct_health_check_with_instrumentation",
         _fake_direct,
     )
-    monkeypatch.setattr(
-        proxy_server, "_schedule_background_health_check_db_save", lambda *a, **kw: None
-    )
-    monkeypatch.setattr(
-        proxy_server, "_write_health_state_to_router_cache", lambda *a, **kw: None
-    )
+    monkeypatch.setattr(proxy_server, "_schedule_background_health_check_db_save", lambda *a, **kw: None)
+    monkeypatch.setattr(proxy_server, "_write_health_state_to_router_cache", lambda *a, **kw: None)
     monkeypatch.setattr(
         proxy_server,
         "health_check_filter_kwargs_from_general_settings",
@@ -630,12 +744,8 @@ async def test_run_background_health_check_probes_only_listed_model_groups(monke
         "_run_direct_health_check_with_instrumentation",
         _fake_direct,
     )
-    monkeypatch.setattr(
-        proxy_server, "_schedule_background_health_check_db_save", lambda *a, **kw: None
-    )
-    monkeypatch.setattr(
-        proxy_server, "_write_health_state_to_router_cache", lambda *a, **kw: None
-    )
+    monkeypatch.setattr(proxy_server, "_schedule_background_health_check_db_save", lambda *a, **kw: None)
+    monkeypatch.setattr(proxy_server, "_write_health_state_to_router_cache", lambda *a, **kw: None)
     monkeypatch.setattr(
         proxy_server,
         "health_check_filter_kwargs_from_general_settings",
diff --git a/tests/test_litellm/proxy/proxy_server/test_lifecycle.py b/tests/test_litellm/proxy/proxy_server/test_lifecycle.py
index dafe686c4f2..deb7289d2d1 100644
--- a/tests/test_litellm/proxy/proxy_server/test_lifecycle.py
+++ b/tests/test_litellm/proxy/proxy_server/test_lifecycle.py
@@ -253,6 +253,38 @@ async def test_flush_spend_logs_queue_on_shutdown_swallows_drain_errors(monkeypa
     await ps._flush_spend_logs_queue_on_shutdown()
 
 
+@pytest.mark.asyncio
+async def test_flush_spend_counters_on_shutdown_commits_buffered_spend(monkeypatch):
+    fake_prisma = MagicMock()
+    monkeypatch.setattr(ps, "prisma_client", fake_prisma, raising=False)
+    commit = AsyncMock()
+    monkeypatch.setattr(ps.proxy_logging_obj.db_spend_update_writer, "db_update_spend_transaction_handler", commit)
+
+    await ps.flush_spend_counters_on_shutdown()
+
+    observed = {
+        "commit_calls": commit.await_count,
+        "commit_prisma": commit.await_args.kwargs["prisma_client"] is fake_prisma,
+        "commit_proxy_logging": commit.await_args.kwargs["proxy_logging_obj"] is ps.proxy_logging_obj,
+    }
+    assert observed == {"commit_calls": 1, "commit_prisma": True, "commit_proxy_logging": True}
+
+
+@pytest.mark.asyncio
+async def test_flush_spend_counters_on_shutdown_logs_and_swallows_commit_errors(monkeypatch, caplog):
+    monkeypatch.setattr(ps, "prisma_client", MagicMock(), raising=False)
+    monkeypatch.setattr(
+        ps.proxy_logging_obj.db_spend_update_writer,
+        "db_update_spend_transaction_handler",
+        AsyncMock(side_effect=RuntimeError("db gone")),
+    )
+
+    with caplog.at_level(logging.ERROR, logger="LiteLLM Proxy"):
+        await ps.flush_spend_counters_on_shutdown()
+
+    assert "Error flushing spend counters on shutdown: db gone" in caplog.text
+
+
 # ---------------------------------------------------------------------------
 # _initialize_shared_aiohttp_session
 # ---------------------------------------------------------------------------
diff --git a/tests/test_litellm/proxy/proxy_server/test_routes_config.py b/tests/test_litellm/proxy/proxy_server/test_routes_config.py
index dcb63b8ca82..2d9c1bd8b46 100644
--- a/tests/test_litellm/proxy/proxy_server/test_routes_config.py
+++ b/tests/test_litellm/proxy/proxy_server/test_routes_config.py
@@ -13,9 +13,12 @@ Routes covered:
 
 from __future__ import annotations
 
+import asyncio
 import json
 from unittest.mock import AsyncMock, MagicMock
 
+import pytest
+
 from .conftest import VOLATILE_KEYS, normalize
 
 
@@ -229,10 +232,7 @@ def test_config_update_no_db_error(client, auth_as, monkeypatch):
             json={"general_settings": {"alerting": ["slack"]}},
         )
     assert response.status_code != 200
-    assert (
-        "db" in str(response.json()).lower()
-        or "connect" in str(response.json()).lower()
-    )
+    assert "db" in str(response.json()).lower() or "connect" in str(response.json()).lower()
 
 
 # ---------------------------------------------------------------------------
@@ -273,9 +273,7 @@ def test_config_field_update_happy_admin(client, auth_as, mock_prisma, monkeypat
     }
 
 
-def test_config_field_update_non_admin_rejected(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_update_non_admin_rejected(client, auth_as, mock_prisma, monkeypatch):
     """Non-admin cannot update config fields — returns 400 with not-allowed
     detail (handler uses 400 for the auth gate, not 403)."""
     from litellm.proxy import proxy_server as ps
@@ -335,9 +333,7 @@ def test_config_field_info_happy_admin(client, auth_as, mock_prisma, monkeypatch
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.get(
-            "/config/field/info", params={"field_name": "max_parallel_requests"}
-        )
+        response = client.get("/config/field/info", params={"field_name": "max_parallel_requests"})
     assert response.status_code == 200
     assert normalize(response.json()) == {
         "field_name": "max_parallel_requests",
@@ -345,9 +341,7 @@ def test_config_field_info_happy_admin(client, auth_as, mock_prisma, monkeypatch
     }
 
 
-def test_config_field_info_non_admin_rejected(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_info_non_admin_rejected(client, auth_as, mock_prisma, monkeypatch):
     """Non-admin (INTERNAL_USER) is denied — admin-view gate fires."""
     from litellm.proxy import proxy_server as ps
     from litellm.proxy._types import LitellmUserRoles
@@ -356,9 +350,7 @@ def test_config_field_info_non_admin_rejected(
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.INTERNAL_USER):
-        response = client.get(
-            "/config/field/info", params={"field_name": "max_parallel_requests"}
-        )
+        response = client.get("/config/field/info", params={"field_name": "max_parallel_requests"})
     assert response.status_code == 400
     assert "error" in response.json().get("detail", {})
 
@@ -375,16 +367,12 @@ def test_config_field_info_field_not_in_db(client, auth_as, mock_prisma, monkeyp
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.get(
-            "/config/field/info", params={"field_name": "max_parallel_requests"}
-        )
+        response = client.get("/config/field/info", params={"field_name": "max_parallel_requests"})
     assert response.status_code == 400
     assert "not in DB" in response.json().get("detail", {}).get("error", "")
 
 
-def test_config_field_info_redacts_nested_secret_for_view_only_admin(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_info_redacts_nested_secret_for_view_only_admin(client, auth_as, mock_prisma, monkeypatch):
     """A view-only admin reading a structured field must not receive nested
     credentials. database_args carries aws_web_identity_token (a DynamoDB
     role-assumption credential); it must come back redacted while non-secret
@@ -405,9 +393,7 @@ def test_config_field_info_redacts_nested_secret_for_view_only_admin(
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN_VIEW_ONLY):
-        response = client.get(
-            "/config/field/info", params={"field_name": "database_args"}
-        )
+        response = client.get("/config/field/info", params={"field_name": "database_args"})
     assert response.status_code == 200
     value = response.json()["field_value"]
     assert value["aws_web_identity_token"] == "REDACTED"
@@ -415,9 +401,7 @@ def test_config_field_info_redacts_nested_secret_for_view_only_admin(
     assert value["user_table_name"] == "LiteLLM_UserTable"
 
 
-def test_config_field_info_full_admin_sees_nested_secret(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_info_full_admin_sees_nested_secret(client, auth_as, mock_prisma, monkeypatch):
     """The redaction must not over-redact for a full PROXY_ADMIN, who needs
     the real nested value to populate the edit form."""
     from litellm.proxy import proxy_server as ps
@@ -435,18 +419,14 @@ def test_config_field_info_full_admin_sees_nested_secret(
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.get(
-            "/config/field/info", params={"field_name": "database_args"}
-        )
+        response = client.get("/config/field/info", params={"field_name": "database_args"})
     assert response.status_code == 200
     value = response.json()["field_value"]
     assert value["aws_web_identity_token"] == "sk-super-secret-token"
     assert value["region_name"] == "us-east-1"
 
 
-def test_config_field_info_redacts_top_level_scalar_for_view_only(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_info_redacts_top_level_scalar_for_view_only(client, auth_as, mock_prisma, monkeypatch):
     """The top-level scalar branch must also redact for a view-only admin.
     database_url carries DB credentials and is not caught by the name masker,
     so it is in the explicit secret set."""
@@ -460,9 +440,7 @@ def test_config_field_info_redacts_top_level_scalar_for_view_only(
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN_VIEW_ONLY):
-        response = client.get(
-            "/config/field/info", params={"field_name": "database_url"}
-        )
+        response = client.get("/config/field/info", params={"field_name": "database_url"})
     assert response.status_code == 200
     assert response.json()["field_value"] == "REDACTED"
 
@@ -476,17 +454,12 @@ def test_redact_general_setting_value_recurses_list_of_dicts():
         {"path": "/foo", "headers": {"Authorization": "Bearer sk-x"}},
         {"path": "/bar", "client_secret": "sk-y"},
     ]
-    redacted = ps._redact_general_setting_value(
-        "some_list_field", value, is_full_admin=False
-    )
+    redacted = ps._redact_general_setting_value("some_list_field", value, is_full_admin=False)
     assert redacted[0]["headers"]["Authorization"] == "REDACTED"
     assert redacted[0]["path"] == "/foo"
     assert redacted[1]["client_secret"] == "REDACTED"
     assert redacted[1]["path"] == "/bar"
-    assert (
-        ps._redact_general_setting_value("some_list_field", value, is_full_admin=True)
-        == value
-    )
+    assert ps._redact_general_setting_value("some_list_field", value, is_full_admin=True) == value
 
 
 def test_redact_secret_values_in_obj_fails_closed_at_max_depth():
@@ -504,22 +477,16 @@ def test_redact_secret_values_in_obj_fails_closed_at_max_depth():
     for _ in range(ps._REDACT_SECRET_MAX_DEPTH + 2):
         nested = {"wrap": nested}
 
-    out = ps._redact_general_setting_value(
-        "some_struct_field", nested, is_full_admin=False
-    )
+    out = ps._redact_general_setting_value("some_struct_field", nested, is_full_admin=False)
     # the secret must not survive anywhere in the returned tree
     assert "sk-leak-bottom" not in repr(out)
 
     # full admin is unaffected by the cap — the value comes back untouched
-    admin_out = ps._redact_general_setting_value(
-        "some_struct_field", nested, is_full_admin=True
-    )
+    admin_out = ps._redact_general_setting_value("some_struct_field", nested, is_full_admin=True)
     assert admin_out is nested
 
 
-def test_config_list_redacts_pass_through_secret_for_view_only(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_list_redacts_pass_through_secret_for_view_only(client, auth_as, mock_prisma, monkeypatch):
     """/config/list must not leak pass_through_endpoints upstream credentials
     to a view-only admin. pass_through_endpoints is a known secret-bearing
     field, so a non-admin gets it redacted; a full admin still sees it."""
@@ -546,24 +513,16 @@ def test_config_list_redacts_pass_through_secret_for_view_only(
     )
 
     def _pass_through_value(body):
-        return next(
-            entry["field_value"]
-            for entry in body
-            if entry["field_name"] == "pass_through_endpoints"
-        )
+        return next(entry["field_value"] for entry in body if entry["field_name"] == "pass_through_endpoints")
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN_VIEW_ONLY):
-        view_resp = client.get(
-            "/config/list", params={"config_type": "general_settings"}
-        )
+        view_resp = client.get("/config/list", params={"config_type": "general_settings"})
     assert view_resp.status_code == 200
     assert "sk-UPSTREAM-SECRET" not in view_resp.text
     assert _pass_through_value(view_resp.json()) == "REDACTED"
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        admin_resp = client.get(
-            "/config/list", params={"config_type": "general_settings"}
-        )
+        admin_resp = client.get("/config/list", params={"config_type": "general_settings"})
     assert admin_resp.status_code == 200
     admin_value = _pass_through_value(admin_resp.json())
     assert admin_value[0]["headers"]["Authorization"] == "Bearer sk-UPSTREAM-SECRET"
@@ -587,9 +546,7 @@ def test_config_list_happy_admin(client, auth_as, mock_prisma, monkeypatch):
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.get(
-            "/config/list", params={"config_type": "general_settings"}
-        )
+        response = client.get("/config/list", params={"config_type": "general_settings"})
     assert response.status_code == 200
     body = response.json()
     assert isinstance(body, list)
@@ -695,9 +652,7 @@ def test_config_list_non_admin_rejected(client, auth_as, mock_prisma, monkeypatc
     monkeypatch.setattr(ps, "prisma_client", mock_prisma)
 
     with auth_as(LitellmUserRoles.INTERNAL_USER):
-        response = client.get(
-            "/config/list", params={"config_type": "general_settings"}
-        )
+        response = client.get("/config/list", params={"config_type": "general_settings"})
     assert response.status_code == 400
     assert "role" in response.json().get("detail", {}).get("error", "").lower()
 
@@ -710,9 +665,7 @@ def test_config_list_no_db_error(client, auth_as, monkeypatch):
     monkeypatch.setattr(ps, "prisma_client", None)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.get(
-            "/config/list", params={"config_type": "general_settings"}
-        )
+        response = client.get("/config/list", params={"config_type": "general_settings"})
     assert response.status_code == 400
     assert "error" in response.json().get("detail", {})
 
@@ -756,9 +709,7 @@ def test_config_field_delete_happy_admin(client, auth_as, mock_prisma, monkeypat
     }
 
 
-def test_config_field_delete_non_admin_rejected(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_delete_non_admin_rejected(client, auth_as, mock_prisma, monkeypatch):
     """Non-admin caller hits the 400 not-allowed branch with role in detail."""
     from litellm.proxy import proxy_server as ps
     from litellm.proxy._types import LitellmUserRoles
@@ -778,9 +729,7 @@ def test_config_field_delete_non_admin_rejected(
     assert "role" in response.json().get("detail", {}).get("error", "").lower()
 
 
-def test_config_field_delete_field_not_in_config(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_field_delete_field_not_in_config(client, auth_as, mock_prisma, monkeypatch):
     """If there is no general_settings row at all, returns 400 'not in config'."""
     from litellm.proxy import proxy_server as ps
     from litellm.proxy._types import LitellmUserRoles
@@ -825,9 +774,7 @@ def test_config_callback_delete_happy_admin(client, auth_as, mock_prisma, monkey
     monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.post(
-            "/config/callback/delete", json={"callback_name": "langfuse"}
-        )
+        response = client.post("/config/callback/delete", json={"callback_name": "langfuse"})
     assert response.status_code == 200
     # `deleted_at` is an ISO timestamp generated at request time — extend
     # the volatile set just for this assertion so dict-equality still works.
@@ -840,9 +787,7 @@ def test_config_callback_delete_happy_admin(client, auth_as, mock_prisma, monkey
     }
 
 
-def test_config_callback_delete_non_admin_rejected(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_config_callback_delete_non_admin_rejected(client, auth_as, mock_prisma, monkeypatch):
     """Non-admin caller is rejected with 400 not-allowed."""
     from litellm.proxy import proxy_server as ps
     from litellm.proxy._types import LitellmUserRoles
@@ -852,9 +797,7 @@ def test_config_callback_delete_non_admin_rejected(
     monkeypatch.setattr(ps, "store_model_in_db", True)
 
     with auth_as(LitellmUserRoles.INTERNAL_USER):
-        response = client.post(
-            "/config/callback/delete", json={"callback_name": "langfuse"}
-        )
+        response = client.post("/config/callback/delete", json={"callback_name": "langfuse"})
     assert response.status_code == 400
     assert "role" in response.json().get("detail", {}).get("error", "").lower()
 
@@ -869,22 +812,15 @@ def test_config_callback_delete_not_found(client, auth_as, mock_prisma, monkeypa
     monkeypatch.setattr(ps, "store_model_in_db", True)
 
     fake_proxy_config = MagicMock()
-    fake_proxy_config.get_config = AsyncMock(
-        return_value={"litellm_settings": {"success_callback": ["slack"]}}
-    )
+    fake_proxy_config.get_config = AsyncMock(return_value={"litellm_settings": {"success_callback": ["slack"]}})
     monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
 
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
-        response = client.post(
-            "/config/callback/delete", json={"callback_name": "langfuse"}
-        )
+        response = client.post("/config/callback/delete", json={"callback_name": "langfuse"})
     # The handler re-raises HTTPException(404) verbatim (only generic
     # `Exception` becomes a 500 ProxyException), so pin 404 strictly.
     assert response.status_code == 404
-    assert (
-        "langfuse" in str(response.json()).lower()
-        or "not found" in str(response.json()).lower()
-    )
+    assert "langfuse" in str(response.json()).lower() or "not found" in str(response.json()).lower()
 
 
 # ---------------------------------------------------------------------------
@@ -948,10 +884,7 @@ def test_get_config_callbacks_internal_error(client, auth_as, mock_prisma, monke
     with auth_as(LitellmUserRoles.PROXY_ADMIN):
         response = client.get("/get/config/callbacks")
     assert response.status_code >= 400
-    assert (
-        "boom" in str(response.json()).lower()
-        or "error" in str(response.json()).lower()
-    )
+    assert "boom" in str(response.json()).lower() or "error" in str(response.json()).lower()
 
 
 _CALLBACK_ENV_FIXTURE = {
@@ -985,14 +918,10 @@ def _install_callbacks_config(monkeypatch, mock_prisma):
 
 
 def _callback_variables(body: dict, name: str) -> dict:
-    return next(
-        cb["variables"] for cb in body["callbacks"] if cb["name"] == name
-    )
+    return next(cb["variables"] for cb in body["callbacks"] if cb["name"] == name)
 
 
-def test_get_config_callbacks_redacts_secret_env_vars_for_view_only_admin(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_get_config_callbacks_redacts_secret_env_vars_for_view_only_admin(client, auth_as, mock_prisma, monkeypatch):
     from litellm.proxy._types import LitellmUserRoles
 
     _install_callbacks_config(monkeypatch, mock_prisma)
@@ -1024,9 +953,7 @@ def test_get_config_callbacks_redacts_secret_env_vars_for_view_only_admin(
     assert otel_vars["OTEL_ENDPOINT"] == _CALLBACK_ENV_FIXTURE["OTEL_ENDPOINT"]
 
 
-def test_get_config_callbacks_full_admin_still_sees_secret_env_vars(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_get_config_callbacks_full_admin_still_sees_secret_env_vars(client, auth_as, mock_prisma, monkeypatch):
     from litellm.proxy._types import LitellmUserRoles
 
     _install_callbacks_config(monkeypatch, mock_prisma)
@@ -1047,9 +974,7 @@ def test_get_config_callbacks_full_admin_still_sees_secret_env_vars(
     assert otel_vars["OTEL_HEADERS"] == _CALLBACK_ENV_FIXTURE["OTEL_HEADERS"]
 
 
-def test_get_config_callbacks_redacts_slack_webhook_urls_for_view_only_admin(
-    client, auth_as, mock_prisma, monkeypatch
-):
+def test_get_config_callbacks_redacts_slack_webhook_urls_for_view_only_admin(client, auth_as, mock_prisma, monkeypatch):
     from litellm.proxy import proxy_server as ps
     from litellm.proxy._types import LitellmUserRoles
 
@@ -1170,6 +1095,413 @@ def test_get_config_callbacks_redacts_email_alerting_vars_for_view_only_admin(
     assert admin_email["SMTP_HOST"] == "smtp.resend.com"
 
 
+def test_get_config_callbacks_appends_runtime_only_callbacks(client, auth_as, mock_prisma, monkeypatch):
+    """LIT-5281: a YAML callback that the DB callback list replaced in the merged config still runs, so it must
+    show up as a read_only row next to the editable DB-configured one."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"success_callback": ["langfuse"]},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    import litellm
+    from litellm.integrations.langsmith import LangsmithLogger
+    from litellm.integrations.opentelemetry import OpenTelemetry
+
+    monkeypatch.setattr(litellm, "success_callback", ["langfuse", LangsmithLogger()])
+    monkeypatch.setattr(litellm, "_async_success_callback", [])
+    monkeypatch.setattr(litellm, "failure_callback", [])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [])
+    monkeypatch.setattr(litellm, "callbacks", [OpenTelemetry()])
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+    assert response.status_code == 200
+
+    assert [(cb["name"], cb["type"], cb.get("read_only", False)) for cb in response.json()["callbacks"]] == [
+        ("langfuse", "success", False),
+        ("langsmith", "success", True),
+        ("otel", "success_and_failure", True),
+    ]
+
+
+def test_get_config_callbacks_accepts_scalar_and_null_yaml_callbacks(client, auth_as, mock_prisma, monkeypatch):
+    """`success_callback: langfuse` (a YAML scalar) is one configured callback, not eight single-letter ones, and a
+    `callbacks: null` key contributes nothing."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"success_callback": "langfuse", "failure_callback": None, "callbacks": None},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    import litellm
+    from litellm.integrations.langsmith import LangsmithLogger
+
+    monkeypatch.setattr(litellm, "success_callback", ["langfuse", LangsmithLogger()])
+    monkeypatch.setattr(litellm, "_async_success_callback", [])
+    monkeypatch.setattr(litellm, "failure_callback", [])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [])
+    monkeypatch.setattr(litellm, "callbacks", [])
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+    assert response.status_code == 200
+
+    assert [(cb["name"], cb["type"], cb.get("read_only", False)) for cb in response.json()["callbacks"]] == [
+        ("langfuse", "success", False),
+        ("langsmith", "success", True),
+    ]
+
+
+def test_get_config_callbacks_deduplicates_configured_and_runtime(client, auth_as, mock_prisma, monkeypatch):
+    """A configured callback shows once as editable, whether the runtime holds its string or an initialized instance
+    (arize initializes an ArizeLogger, logfire a bare OpenTelemetry that only its class identifies)."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"success_callback": ["langfuse", "arize", "logfire"]},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    import litellm
+    from litellm.integrations.arize.arize import ArizeLogger
+    from litellm.integrations.opentelemetry import OpenTelemetry, OpenTelemetryConfig
+
+    arize_logger = ArizeLogger(config=OpenTelemetryConfig(exporter="console"), callback_name="arize")
+    monkeypatch.setattr(litellm, "success_callback", ["langfuse", arize_logger, OpenTelemetry()])
+    monkeypatch.setattr(litellm, "callbacks", [])
+    monkeypatch.setattr(litellm, "failure_callback", [])
+    monkeypatch.setattr(litellm, "_async_success_callback", [])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [])
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+    assert response.status_code == 200
+
+    assert [(cb["name"], cb["type"], cb.get("read_only", False)) for cb in response.json()["callbacks"]] == [
+        ("langfuse", "success", False),
+        ("arize", "success", False),
+        ("logfire", "success", False),
+    ]
+
+
+def test_get_config_callbacks_keeps_yaml_otel_family_callbacks_next_to_configured_one(
+    client, auth_as, mock_prisma, monkeypatch
+):
+    """LIT-5281: arize, weave_otel and langfuse_otel all initialize OpenTelemetry subclasses. Saving one of them
+    from the dashboard replaces the YAML `callbacks` list, so the YAML siblings keep running and must stay listed
+    under their own names instead of being hidden as duplicates of the configured OTel callback."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"callbacks": ["langfuse_otel"]},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    import litellm
+    from litellm.integrations.arize.arize import ArizeLogger
+    from litellm.integrations.langfuse.langfuse_otel import LangfuseOtelLogger
+    from litellm.integrations.langsmith import LangsmithLogger
+    from litellm.integrations.opentelemetry import OpenTelemetryConfig
+    from litellm.integrations.weave.weave_otel import WeaveOtelLogger
+
+    console_config = OpenTelemetryConfig(exporter="console")
+    monkeypatch.setattr(litellm, "success_callback", [LangsmithLogger()])
+    monkeypatch.setattr(litellm, "_async_success_callback", [])
+    monkeypatch.setattr(litellm, "failure_callback", [])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [])
+    monkeypatch.setattr(
+        litellm,
+        "callbacks",
+        [
+            ArizeLogger(config=console_config, callback_name="arize"),
+            WeaveOtelLogger(config=console_config),
+            LangfuseOtelLogger(config=console_config, callback_name="langfuse_otel"),
+        ],
+    )
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+    assert response.status_code == 200
+
+    assert [(cb["name"], cb["type"], cb.get("read_only", False)) for cb in response.json()["callbacks"]] == [
+        ("langfuse_otel", "success_and_failure", False),
+        ("arize", "success_and_failure", True),
+        ("langsmith", "success", True),
+        ("weave_otel", "success_and_failure", True),
+    ]
+
+
+def _dotted_path_test_function(*args, **kwargs):
+    pass
+
+
+@pytest.mark.parametrize("handler_kind", ["instance", "function"])
+@pytest.mark.parametrize(
+    "config_key,expected_type",
+    [
+        ("success_callback", "success"),
+        ("failure_callback", "failure"),
+        ("callbacks", "success_and_failure"),
+    ],
+)
+def test_get_config_callbacks_deduplicates_dotted_path_callback(
+    client, auth_as, mock_prisma, monkeypatch, config_key, expected_type, handler_kind
+):
+    """A dotted-path callback stays a single editable row instead of duplicating under its class or function name."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    import litellm
+    from litellm.integrations.custom_logger import CustomLogger
+
+    class _DottedPathTestHandler(CustomLogger):
+        pass
+
+    dotted_handler = _DottedPathTestHandler() if handler_kind == "instance" else _dotted_path_test_function
+    dotted_path = f"{__name__}.dotted_handler"
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {config_key: [dotted_path]},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    monkeypatch.setattr(litellm, "callbacks", [dotted_handler])
+    monkeypatch.setattr(litellm, "success_callback", [])
+    monkeypatch.setattr(litellm, "failure_callback", [])
+    monkeypatch.setattr(litellm, "_async_success_callback", [])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [])
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+
+    assert response.status_code == 200
+    callbacks = response.json()["callbacks"]
+    assert [(callback["name"], callback["type"], callback.get("read_only", False)) for callback in callbacks] == [
+        (dotted_path, expected_type, False)
+    ]
+
+
+def test_get_config_callbacks_lists_dict_shaped_config_callbacks(client, auth_as, mock_prisma, monkeypatch):
+    """Dict-shaped success_callback config values list their keys as editable rows."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"success_callback": {"langsmith": {"batch_size": 1}}},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    import litellm
+
+    monkeypatch.setattr(
+        litellm.logging_callback_manager,
+        "get_callbacks_by_type",
+        MagicMock(return_value={"success": ["langsmith"], "failure": [], "success_and_failure": []}),
+    )
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+
+    assert response.status_code == 200
+    callbacks = response.json()["callbacks"]
+    assert [(callback["name"], callback.get("read_only", False)) for callback in callbacks] == [("langsmith", False)]
+
+
+def test_get_config_callbacks_excludes_internal_runtime_callbacks(client, auth_as, mock_prisma, monkeypatch):
+    """Proxy infrastructure callbacks are excluded from callback inventory."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"success_callback": []},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    from litellm_enterprise.proxy.hooks.managed_files import _PROXY_LiteLLMManagedFiles
+
+    import litellm
+    from litellm._service_logger import ServiceLogging
+    from litellm.integrations.custom_guardrail import CustomGuardrail
+    from litellm.integrations.custom_logger import CustomLogger
+    from litellm.integrations.langsmith import LangsmithLogger
+    from litellm.integrations.s3_v2 import S3Logger
+    from litellm.integrations.sqs import SQSLogger
+    from litellm.integrations.vector_store_integrations.vector_store_pre_call_hook import VectorStorePreCallHook
+    from litellm.proxy.hooks.max_budget_limiter import _PROXY_MaxBudgetLimiter
+    from litellm.router import Router
+
+    class _InventoryTestGuardrail(CustomGuardrail):
+        pass
+
+    class _UserCodeLogger(CustomLogger):
+        pass
+
+    def user_code_function(*args, **kwargs):
+        pass
+
+    async def build_aws_loggers() -> tuple[S3Logger, SQSLogger]:
+        return S3Logger(s3_bucket_name="inventory-bucket"), SQSLogger(sqs_queue_url="https://sqs.example/inventory")
+
+    s3_logger, sqs_logger = asyncio.run(build_aws_loggers())
+    router = Router(model_list=[])
+    monkeypatch.setattr(litellm, "input_callback", [])
+    monkeypatch.setattr(
+        litellm, "success_callback", [LangsmithLogger(), s3_logger, router.sync_deployment_callback_on_success]
+    )
+    monkeypatch.setattr(litellm, "_async_success_callback", [sqs_logger, router.deployment_callback_on_success])
+    monkeypatch.setattr(litellm, "failure_callback", [user_code_function])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [router.async_deployment_callback_on_failure])
+    monkeypatch.setattr(
+        litellm,
+        "callbacks",
+        [
+            _PROXY_MaxBudgetLimiter(),
+            _PROXY_LiteLLMManagedFiles(internal_usage_cache=MagicMock(), prisma_client=MagicMock()),
+            ServiceLogging(),
+            VectorStorePreCallHook(),
+            _InventoryTestGuardrail(guardrail_name="inventory-test-guardrail"),
+            _UserCodeLogger(),
+        ],
+    )
+    monkeypatch.setattr(litellm, "cache", litellm.Cache(type="local"))
+    assert "cache" in litellm.success_callback and "cache" in litellm._async_success_callback
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        response = client.get("/get/config/callbacks")
+
+    assert response.status_code == 200
+    assert [
+        (callback["name"], callback["type"], callback["read_only"]) for callback in response.json()["callbacks"]
+    ] == [
+        ("_UserCodeLogger", "success_and_failure", True),
+        ("langsmith", "success", True),
+        ("s3", "success", True),
+        ("sqs", "success", True),
+        ("user_code_function", "failure", True),
+    ]
+
+
+def test_get_config_callbacks_redacts_runtime_only_row_secrets_for_view_only_admin(
+    client, auth_as, mock_prisma, monkeypatch
+):
+    """Runtime-only callback rows are subject to the same redaction gate as configured."""
+    from litellm.proxy import proxy_server as ps
+    from litellm.proxy._types import LitellmUserRoles
+
+    _install_litellm_config(mock_prisma)
+    monkeypatch.setattr(ps, "prisma_client", mock_prisma)
+    monkeypatch.setattr(ps, "llm_router", None)
+
+    fake_proxy_config = MagicMock()
+    fake_proxy_config.get_config = AsyncMock(
+        return_value={
+            "litellm_settings": {"success_callback": []},
+            "general_settings": {},
+            "environment_variables": dict(_CALLBACK_ENV_FIXTURE),
+        }
+    )
+    monkeypatch.setattr(ps, "proxy_config", fake_proxy_config)
+
+    import litellm
+
+    monkeypatch.setattr(litellm, "success_callback", [])
+    monkeypatch.setattr(litellm, "_async_success_callback", [])
+    monkeypatch.setattr(litellm, "failure_callback", [])
+    monkeypatch.setattr(litellm, "_async_failure_callback", [])
+    monkeypatch.setattr(litellm, "callbacks", ["otel"])
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN_VIEW_ONLY):
+        response = client.get("/get/config/callbacks")
+    assert response.status_code == 200
+    body = response.json()
+
+    callbacks = body["callbacks"]
+    otel_cb = next((cb for cb in callbacks if cb["name"] == "otel"), None)
+    assert otel_cb is not None
+    assert otel_cb["type"] == "success_and_failure"
+    assert otel_cb["read_only"] is True
+    assert otel_cb["variables"]["OTEL_HEADERS"] == "REDACTED"
+    assert otel_cb["variables"]["OTEL_ENDPOINT"] == _CALLBACK_ENV_FIXTURE["OTEL_ENDPOINT"]
+
+    with auth_as(LitellmUserRoles.PROXY_ADMIN):
+        admin_response = client.get("/get/config/callbacks")
+    assert admin_response.status_code == 200
+    admin_body = admin_response.json()
+    admin_otel = next((cb for cb in admin_body["callbacks"] if cb["name"] == "otel"), None)
+    assert admin_otel is not None
+    assert admin_otel["variables"]["OTEL_HEADERS"] == _CALLBACK_ENV_FIXTURE["OTEL_HEADERS"]
+
+
 # ---------------------------------------------------------------------------
 # GET /config/yaml
 # ---------------------------------------------------------------------------
@@ -1183,9 +1515,7 @@ def test_config_yaml_returns_demo_payload(client, auth_as):
         response = client.request("GET", "/config/yaml", json={})
     shape = {
         "status": response.status_code,
-        "media_type_yaml": response.headers.get("content-type", "").startswith(
-            "application/json"
-        ),
+        "media_type_yaml": response.headers.get("content-type", "").startswith("application/json"),
         "has_body": len(response.content) > 0,
     }
     assert shape == {
diff --git a/tests/test_litellm/proxy/proxy_server/test_routes_models.py b/tests/test_litellm/proxy/proxy_server/test_routes_models.py
index bc6106a06f8..d31d952a03e 100644
--- a/tests/test_litellm/proxy/proxy_server/test_routes_models.py
+++ b/tests/test_litellm/proxy/proxy_server/test_routes_models.py
@@ -17,6 +17,7 @@ import litellm
 from litellm.proxy import proxy_server
 from litellm.proxy import utils as proxy_utils
 from litellm.proxy.utils import create_model_info_response
+from litellm.types.router import DeploymentModelListingInfo
 
 from .conftest import normalize  # type: ignore[import-not-found]
 
@@ -166,13 +167,16 @@ def test_anthropic_format_carries_router_configured_token_limits(client, auth_as
     built from another entry's lookup shows up as the wrong numbers."""
 
     def _configured(model_name):
-        return (300000, 32000) if model_name == "gpt-4" else (500000, 4096)
+        max_input, max_output = (300000, 32000) if model_name == "gpt-4" else (500000, 4096)
+        return DeploymentModelListingInfo(
+            cost_map_keys=(model_name,), max_input_tokens=max_input, max_output_tokens=max_output
+        )
 
     def _cost_map_lookup(model_id):
         max_input, max_output = (200000, 64000) if model_id == "gpt-4" else (100000, 8000)
         return {"max_input_tokens": max_input, "max_output_tokens": max_output, "mode": "chat"}
 
-    patched_models.get_configured_token_limits = MagicMock(side_effect=_configured)
+    patched_models.get_model_listing_info = MagicMock(side_effect=_configured)
 
     def _resolved(**kwargs):
         return create_model_info_response(**kwargs, get_model_info=_cost_map_lookup)
@@ -343,3 +347,53 @@ def test_anthropic_format_returns_public_team_model_name(
     assert response.status_code == 200
     assert [m["id"] for m in response.json()["data"]] == ["gpt-4-team"]
     assert internal_name not in response.text
+
+
+@pytest.mark.parametrize("path", ["/v1/models", "/models"])
+@pytest.mark.parametrize(
+    "caller_headers",
+    [
+        {"anthropic-version": "2023-06-01", "user-agent": "claude-code/2.1.267"},
+        {"anthropic-version": "2023-06-01", "user-agent": "claude-cli/2.1.267 (external, sdk-cli)"},
+        {"anthropic-version": "2023-06-01", "x-gateway-client": "claude-code"},
+    ],
+)
+def test_anthropic_format_lists_claude_code_view_ids_for_claude_code(
+    client, auth_as, patched_models, monkeypatch, path, caller_headers
+):
+    """Claude Code drops every id without claude/anthropic in it and reads [1m] as its 1M marker, so for Claude
+    Code (its discovery fetch's own user agent, its SDK's, or the gateway-client header a launcher sends) every
+    group is listed under a Claude-shaped id with the marker where the window reaches 1M; the display name stays
+    the served name."""
+
+    def _create_model_info_response(model_id, provider="openai", **kwargs):
+        if model_id != "claude-sonnet":
+            return _stub_model_info_response(model_id=model_id, provider=provider)
+        return {**_stub_model_info_response(model_id=model_id, provider=provider), "max_input_tokens": 1000000}
+
+    patched_models.model_group_alias = {}
+    patched_models.has_model_id.return_value = False
+    patched_models.get_candidate_model_ids_for_route.side_effect = lambda name, team_id=None: frozenset({name}) if name in ("gpt-4", "claude-sonnet") else frozenset()
+    monkeypatch.setattr(proxy_utils, "create_model_info_response", _create_model_info_response)
+
+    with auth_as():
+        response = client.get(path, headers=caller_headers)
+
+    assert response.status_code == 200
+    body = response.json()
+    assert [(m["id"], m["display_name"]) for m in body["data"]] == [
+        ("claude-router-6770742d34", "gpt-4"),
+        ("claude-sonnet[1m]", "claude-sonnet"),
+    ]
+    assert (body["first_id"], body["last_id"]) == ("claude-router-6770742d34", "claude-sonnet[1m]")
+    assert [row["source_model"] for row in body["data"]] == ["gpt-4", "claude-sonnet"]
+
+
+@pytest.mark.parametrize("path", ["/v1/models", "/models"])
+def test_anthropic_format_keeps_served_ids_for_other_anthropic_clients(client, auth_as, patched_models, path):
+    """An Anthropic SDK asking for the vendor shape gets the served ids: the view is Claude Code's alone."""
+    with auth_as():
+        response = client.get(path, headers={"anthropic-version": "2023-06-01", "user-agent": "anthropic-sdk-python/0.40"})
+
+    assert response.status_code == 200
+    assert [m["id"] for m in response.json()["data"]] == ["gpt-4", "claude-sonnet"]
diff --git a/tests/test_litellm/proxy/proxy_server/test_spend_counters.py b/tests/test_litellm/proxy/proxy_server/test_spend_counters.py
index 86e97a334df..2f47736a398 100644
--- a/tests/test_litellm/proxy/proxy_server/test_spend_counters.py
+++ b/tests/test_litellm/proxy/proxy_server/test_spend_counters.py
@@ -4,11 +4,12 @@ Pins covered:
 - ``get_current_spend``
 - ``increment_spend_counters``
 - ``_reconcile_budget_reservation_for_counter_update``
-- ``_increment_end_user_and_tag_spend_counters``
-- ``_increment_org_spend_counter``
-- ``_init_and_increment_unreserved_spend_counter``
-- ``_init_and_increment_spend_counter``
-- ``_init_and_increment_window_spend_counter``
+- ``_prepare_end_user_and_tag_spend_increments``
+- ``_prepare_org_spend_increment``
+- ``_prepare_unreserved_spend_counter_increment``
+- ``_prepare_spend_counter_increment``
+- ``_prepare_window_spend_counter_increment``
+- ``_apply_spend_counter_increments``
 - ``_ensure_spend_counter_initialized``
 - ``_get_source_cache_base_spend``
 - ``_ensure_window_spend_counter_initialized``
@@ -48,9 +49,7 @@ def _make_spend_counter_cache(
     cache.in_memory_cache.delete_cache = MagicMock()
     if with_redis:
         cache.redis_cache = MagicMock()
-        cache.redis_cache.async_get_cache = AsyncMock(
-            return_value=redis_get_value, side_effect=redis_get_side_effect
-        )
+        cache.redis_cache.async_get_cache = AsyncMock(return_value=redis_get_value, side_effect=redis_get_side_effect)
         cache.redis_cache.async_increment = AsyncMock(
             return_value=redis_increment_value,
             side_effect=redis_increment_side_effect,
@@ -58,6 +57,8 @@ def _make_spend_counter_cache(
         cache.redis_cache.async_delete_cache = AsyncMock()
         cache.redis_cache.async_set_cache = AsyncMock()
         cache.redis_cache.async_set_max = AsyncMock()
+        cache.redis_cache.async_increment_pipeline = AsyncMock(return_value=None)
+        cache.redis_cache.get_ttl = MagicMock(return_value=None)
     else:
         cache.redis_cache = None
     cache.async_increment_cache = AsyncMock(return_value=redis_increment_value)
@@ -70,9 +71,7 @@ def _make_spend_counter_cache(
 
 def _make_user_api_key_cache(get_value=None, get_side_effect=None):
     cache = MagicMock()
-    cache.async_get_cache = AsyncMock(
-        return_value=get_value, side_effect=get_side_effect
-    )
+    cache.async_get_cache = AsyncMock(return_value=get_value, side_effect=get_side_effect)
     cache.async_set_cache_pipeline = AsyncMock()
     return cache
 
@@ -109,9 +108,7 @@ async def test_get_current_spend_redis_error_falls_back_to_in_memory(monkeypatch
     )
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
-    result = await ps.get_current_spend(
-        counter_key="spend:key:abc", fallback_spend=99.0
-    )
+    result = await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=99.0)
     assert result == 17.0
 
 
@@ -136,9 +133,7 @@ async def test_get_current_spend_floors_stale_low_counter_against_db(monkeypatch
     # the stale counter is repaired up to the authoritative DB value via a
     # monotonic set-max so other workers read the corrected total, and a
     # concurrent increment cannot be clobbered
-    fake_cache.redis_cache.async_set_max.assert_awaited_once_with(
-        key="spend:key:abc", value=12.0
-    )
+    fake_cache.redis_cache.async_set_max.assert_awaited_once_with(key="spend:key:abc", value=12.0)
 
 
 @pytest.mark.asyncio
@@ -169,9 +164,7 @@ async def test_get_current_spend_no_floor_without_max_budget(monkeypatch):
     from_db = AsyncMock(return_value=12.0)
     monkeypatch.setattr(ps.SpendCounterReseed, "from_db", from_db)
 
-    result = await ps.get_current_spend(
-        counter_key="spend:key:abc", fallback_spend=12.0
-    )
+    result = await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=12.0)
 
     assert result == 2.0
     assert from_db.await_count == 0
@@ -210,12 +203,8 @@ async def test_get_current_spend_floor_caches_db_read(monkeypatch):
     from_db = AsyncMock(return_value=12.0)
     monkeypatch.setattr(ps.SpendCounterReseed, "from_db", from_db)
 
-    first = await ps.get_current_spend(
-        counter_key="spend:key:abc", fallback_spend=12.0, max_budget=10.0
-    )
-    second = await ps.get_current_spend(
-        counter_key="spend:key:abc", fallback_spend=12.0, max_budget=10.0
-    )
+    first = await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=12.0, max_budget=10.0)
+    second = await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=12.0, max_budget=10.0)
 
     assert first == 12.0
     assert second == 12.0
@@ -336,9 +325,7 @@ async def test_get_current_spend_floors_window_against_spend_logs(monkeypatch):
 
     assert result == 15.0
     assert wfsl.await_count == 1
-    fake_cache.redis_cache.async_set_max.assert_awaited_once_with(
-        key=counter_key, value=15.0
-    )
+    fake_cache.redis_cache.async_set_max.assert_awaited_once_with(key=counter_key, value=15.0)
 
 
 def _make_window_spend_prisma(row=None, spend_logs_total=0.0):
@@ -379,9 +366,7 @@ async def test_get_current_spend_floors_window_against_maintained_row(monkeypatc
 
     assert result == 15.0
     fake_prisma.db.litellm_spendlogs.group_by.assert_not_awaited()
-    fake_cache.redis_cache.async_set_max.assert_awaited_once_with(
-        key=counter_key, value=15.0
-    )
+    fake_cache.redis_cache.async_set_max.assert_awaited_once_with(key=counter_key, value=15.0)
 
 
 @pytest.mark.asyncio
@@ -393,9 +378,7 @@ async def test_get_current_spend_floors_window_against_logs_when_row_stale(monke
 
     window_start = datetime(2026, 1, 8, tzinfo=timezone.utc)
     fake_prisma = _make_window_spend_prisma(
-        row=SimpleNamespace(
-            window_start=window_start - timedelta(days=7), spend=999.0
-        ),
+        row=SimpleNamespace(window_start=window_start - timedelta(days=7), spend=999.0),
         spend_logs_total=15.0,
     )
     fake_cache = _make_spend_counter_cache(redis_get_value=2.0)
@@ -423,21 +406,13 @@ async def test_get_current_spend_fail_closed_rejects_when_unverifiable(monkeypat
     rather than admitted on an unverifiable budget."""
     from fastapi import HTTPException
 
-    fake_cache = _make_spend_counter_cache(
-        redis_get_side_effect=RuntimeError("redis down")
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_side_effect=RuntimeError("redis down"))
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
-    monkeypatch.setattr(
-        ps, "general_settings", {"fail_closed_budget_enforcement": True}
-    )
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps, "general_settings", {"fail_closed_budget_enforcement": True})
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
     with pytest.raises(HTTPException) as exc:
-        await ps.get_current_spend(
-            counter_key="spend:key:abc", fallback_spend=1.0, max_budget=10.0
-        )
+        await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=1.0, max_budget=10.0)
     assert exc.value.status_code == 503
 
 
@@ -445,18 +420,12 @@ async def test_get_current_spend_fail_closed_rejects_when_unverifiable(monkeypat
 async def test_get_current_spend_fail_closed_off_admits_when_unverifiable(monkeypatch):
     """Default (flag off): an unverifiable read keeps the existing behavior and
     admits using the cached fallback — no new rejection."""
-    fake_cache = _make_spend_counter_cache(
-        redis_get_side_effect=RuntimeError("redis down")
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_side_effect=RuntimeError("redis down"))
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "general_settings", {})
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
-    result = await ps.get_current_spend(
-        counter_key="spend:key:abc", fallback_spend=1.0, max_budget=10.0
-    )
+    result = await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=1.0, max_budget=10.0)
     assert result == 1.0
 
 
@@ -466,13 +435,9 @@ async def test_get_current_spend_fail_closed_admits_when_redis_verified(monkeypa
     authoritative, so an under-budget request is admitted normally."""
     fake_cache = _make_spend_counter_cache(redis_get_value=1.0)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
-    monkeypatch.setattr(
-        ps, "general_settings", {"fail_closed_budget_enforcement": True}
-    )
+    monkeypatch.setattr(ps, "general_settings", {"fail_closed_budget_enforcement": True})
 
-    result = await ps.get_current_spend(
-        counter_key="spend:key:abc", fallback_spend=1.0, max_budget=10.0
-    )
+    result = await ps.get_current_spend(counter_key="spend:key:abc", fallback_spend=1.0, max_budget=10.0)
     assert result == 1.0
 
 
@@ -481,16 +446,10 @@ async def test_get_current_spend_fail_closed_allows_authoritative_fallback(monke
     """End-user/tag callers pass fallback_authoritative=True (their spend is
     loaded fresh from the DB in auth), so fail-closed does not reject them even
     when the counter path is unreadable."""
-    fake_cache = _make_spend_counter_cache(
-        redis_get_side_effect=RuntimeError("redis down")
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_side_effect=RuntimeError("redis down"))
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
-    monkeypatch.setattr(
-        ps, "general_settings", {"fail_closed_budget_enforcement": True}
-    )
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps, "general_settings", {"fail_closed_budget_enforcement": True})
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
     result = await ps.get_current_spend(
         counter_key="spend:end_user:e1",
@@ -508,9 +467,7 @@ async def test_get_current_spend_strict_floors_when_fallback_also_stale(monkeypa
     re-checks the authoritative DB and enforces against it."""
     fake_cache = _make_spend_counter_cache(redis_get_value=0.00001)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
-    monkeypatch.setattr(
-        ps, "general_settings", {"fail_closed_budget_enforcement": True}
-    )
+    monkeypatch.setattr(ps, "general_settings", {"fail_closed_budget_enforcement": True})
     from_db = AsyncMock(return_value=0.5)
     monkeypatch.setattr(ps.SpendCounterReseed, "from_db", from_db)
 
@@ -532,9 +489,7 @@ async def test_get_current_spend_strict_floors_when_fallback_also_stale(monkeypa
 
 @pytest.mark.asyncio
 async def test_increment_spend_counters_increments_all_buckets(monkeypatch):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=None, redis_increment_value=5.0
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_value=None, redis_increment_value=5.0)
     fake_user_cache = _make_user_api_key_cache(get_value=None)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
@@ -543,9 +498,7 @@ async def test_increment_spend_counters_increments_all_buckets(monkeypatch):
     async def _fake_coalesced(**kwargs):
         return None
 
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(side_effect=_fake_coalesced)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(side_effect=_fake_coalesced))
 
     await ps.increment_spend_counters(
         token="hashed-tok",
@@ -554,25 +507,36 @@ async def test_increment_spend_counters_increments_all_buckets(monkeypatch):
         response_cost=5.0,
     )
 
+    pipeline = fake_cache.redis_cache.async_increment_pipeline
+    pipeline.assert_awaited_once()
+    increment_list = pipeline.await_args.kwargs["increment_list"]
+    assert {op["key"] for op in increment_list} == {
+        "spend:key:hashed-tok",
+        "spend:team:t1",
+        "spend:team_member:u1:t1",
+        "spend:user:u1",
+    }
+    assert all(op["increment_value"] == 5.0 for op in increment_list)
     observed = {
         "redis_increment_called": fake_cache.redis_cache.async_increment.called,
-        "increment_calls": fake_cache.redis_cache.async_increment.call_count,
+        "pipeline_calls": pipeline.await_count,
         "user_cache_used": fake_user_cache.async_get_cache.called,
     }
     assert normalize(observed) == {
-        "redis_increment_called": True,
-        "increment_calls": 4,
+        "redis_increment_called": False,
+        "pipeline_calls": 1,
         "user_cache_used": True,
     }
 
 
 class _ConcurrencyProbe:
-    """Stand-in for redis_cache.async_increment that pins concurrency.
+    """Stand-in for redis_cache.async_get_cache that pins concurrency.
 
-    Each call registers itself as in-flight and blocks on ``release`` until the
-    test lets it proceed. ``all_arrived`` fires once ``expected`` distinct scope
-    increments are simultaneously suspended here, which can only happen if the
-    per-scope increments are gathered rather than awaited one after another.
+    Each warm-check read registers itself as in-flight and blocks on ``release``
+    until the test lets it proceed. ``all_arrived`` fires once ``expected``
+    distinct scope warm-checks are simultaneously suspended here, which can only
+    happen if the per-scope prepares are gathered rather than awaited one after
+    another.
     """
 
     def __init__(self, expected_concurrency: int):
@@ -581,36 +545,45 @@ class _ConcurrencyProbe:
         self.max_in_flight = 0
         self.all_arrived = asyncio.Event()
         self.release = asyncio.Event()
-        self.values: dict[str, float] = {}
+        self.keys: list[str] = []
 
-    async def async_increment(self, *, key, value, refresh_ttl=True):
+    async def async_get_cache(self, *, key, **kwargs):
         self.in_flight += 1
         self.max_in_flight = max(self.max_in_flight, self.in_flight)
+        self.keys.append(key)
         if self.in_flight >= self.expected:
             self.all_arrived.set()
         if not self.release.is_set():
             await self.release.wait()
         self.in_flight -= 1
-        self.values[key] = self.values.get(key, 0.0) + value
-        return self.values[key]
+        return 1.0
 
 
 @pytest.mark.asyncio
 async def test_increment_spend_counters_runs_scopes_concurrently(monkeypatch):
     """The six independent scopes (key, team, team_member, user, end_user+tags,
-    org) must be incremented concurrently. The probe only fires once all six are
-    suspended in async_increment at the same time, which is impossible if the
+    org) must prepare their increments concurrently. The probe only fires once
+    all eight warm-check reads (one per counter: 6 scopes + 2 tags) are
+    suspended in async_get_cache at the same time, which is impossible if the
     awaits are chained sequentially."""
-    probe = _ConcurrencyProbe(expected_concurrency=6)
-    fake_cache = _make_spend_counter_cache(redis_get_value=None)
-    fake_cache.redis_cache.async_increment = probe.async_increment
+    probe = _ConcurrencyProbe(expected_concurrency=8)
+    fake_cache = _make_spend_counter_cache()
+    fake_cache.redis_cache.async_get_cache = probe.async_get_cache
+    recorded: dict[str, float] = {}
+
+    async def _record_pipeline(increment_list, **_):
+        results = []
+        for op in increment_list:
+            recorded[op["key"]] = recorded.get(op["key"], 0.0) + op["increment_value"]
+            results.append(recorded[op["key"]])
+        return results
+
+    fake_cache.redis_cache.async_increment_pipeline = AsyncMock(side_effect=_record_pipeline)
     fake_user_cache = _make_user_api_key_cache(get_value=None)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
     task = asyncio.create_task(
         ps.increment_spend_counters(
@@ -630,16 +603,16 @@ async def test_increment_spend_counters_runs_scopes_concurrently(monkeypatch):
         probe.release.set()
         await task
         pytest.fail(
-            "scope increments did not run concurrently; sequential awaits "
-            f"detected (peak in-flight was {probe.max_in_flight}, expected 6)"
+            "scope prepares did not run concurrently; sequential awaits "
+            f"detected (peak in-flight was {probe.max_in_flight}, expected 8)"
         )
 
-    assert probe.in_flight == 6
-    assert probe.max_in_flight == 6
+    assert probe.in_flight == 8
+    assert probe.max_in_flight == 8
     probe.release.set()
     await task
 
-    assert probe.values == {
+    assert recorded == {
         "spend:key:hashed-tok": 5.0,
         "spend:team:t1": 5.0,
         "spend:team_member:u1:t1": 5.0,
@@ -659,26 +632,25 @@ async def test_increment_spend_counters_skips_reserved_counter_keys(monkeypatch)
     import litellm.proxy.spend_tracking.budget_reservation as br
 
     reserved = {"spend:key:hashed-tok", "spend:org:org1"}
-    monkeypatch.setattr(
-        br, "get_reserved_counter_keys", MagicMock(return_value=set(reserved))
-    )
+    monkeypatch.setattr(br, "get_reserved_counter_keys", MagicMock(return_value=set(reserved)))
     monkeypatch.setattr(br, "reconcile_budget_reservation", AsyncMock())
 
     recorded: dict[str, float] = {}
 
-    async def _record_increment(*, key, value, refresh_ttl=True):
-        recorded[key] = recorded.get(key, 0.0) + value
-        return recorded[key]
+    async def _record_pipeline(increment_list, **_):
+        results = []
+        for op in increment_list:
+            recorded[op["key"]] = recorded.get(op["key"], 0.0) + op["increment_value"]
+            results.append(recorded[op["key"]])
+        return results
 
     fake_cache = _make_spend_counter_cache(redis_get_value=None)
-    fake_cache.redis_cache.async_increment = _record_increment
+    fake_cache.redis_cache.async_increment_pipeline = AsyncMock(side_effect=_record_pipeline)
     fake_user_cache = _make_user_api_key_cache(get_value=None)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
     reservation = {"finalized": False}
     await ps.increment_spend_counters(
@@ -708,27 +680,46 @@ async def test_increment_spend_counters_failing_scope_propagates_after_siblings_
 ):
     """A failure in one scope must propagate to the caller (so it can invalidate
     reserved counters) while every other scope still settles rather than being
-    left as an orphaned background task, and the reservation is not finalized."""
-    recorded: dict[str, float] = {}
+    left as an orphaned background task, and the reservation is not finalized.
+    The surviving scopes' increments are still applied in the single pipeline:
+    dropping them would under-count spend, the unsafe direction for budget
+    enforcement."""
+    warmed_keys: list[str] = []
 
-    async def _increment(*, key, value, refresh_ttl=True):
+    async def _warm_check(*, key, **kwargs):
+        warmed_keys.append(key)
         if key == "spend:team:t1":
-            raise RuntimeError("redis increment failed")
-        recorded[key] = recorded.get(key, 0.0) + value
-        return recorded[key]
+            raise RuntimeError("redis get failed")
+        return 1.0
 
-    fake_cache = _make_spend_counter_cache(redis_get_value=None)
-    fake_cache.redis_cache.async_increment = _increment
+    async def _reseed_fails(*, counter_key, **kwargs):
+        if counter_key == "spend:team:t1":
+            raise RuntimeError("reseed failed")
+
+    applied: dict[str, float] = {}
+
+    async def _record_pipeline(increment_list, **_):
+        results = []
+        for op in increment_list:
+            applied[op["key"]] = op["increment_value"]
+            results.append(op["increment_value"])
+        return results
+
+    fake_cache = _make_spend_counter_cache()
+    fake_cache.redis_cache.async_get_cache = AsyncMock(side_effect=_warm_check)
+    fake_cache.redis_cache.async_increment_pipeline = AsyncMock(side_effect=_record_pipeline)
     fake_user_cache = _make_user_api_key_cache(get_value=None)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
     monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
+        ps.SpendCounterReseed,
+        "coalesced",
+        AsyncMock(side_effect=_reseed_fails),
     )
 
     reservation = {"finalized": False}
-    with pytest.raises(RuntimeError, match="redis increment failed"):
+    with pytest.raises(RuntimeError, match="reseed failed"):
         await ps.increment_spend_counters(
             token="hashed-tok",
             team_id="t1",
@@ -741,7 +732,19 @@ async def test_increment_spend_counters_failing_scope_propagates_after_siblings_
         )
 
     assert reservation["finalized"] is False
-    assert recorded == {
+    # every sibling scope settled (its warm-check ran) before the error propagated
+    assert set(warmed_keys) == {
+        "spend:key:hashed-tok",
+        "spend:team:t1",
+        "spend:team_member:u1:t1",
+        "spend:user:u1",
+        "spend:end_user:eu1",
+        "spend:tag:a",
+        "spend:org:org1",
+    }
+    # the surviving scopes' increments were still applied, in one pipeline call
+    fake_cache.redis_cache.async_increment_pipeline.assert_awaited_once()
+    assert applied == {
         "spend:key:hashed-tok": 5.0,
         "spend:team_member:u1:t1": 5.0,
         "spend:user:u1": 5.0,
@@ -749,6 +752,7 @@ async def test_increment_spend_counters_failing_scope_propagates_after_siblings_
         "spend:tag:a": 5.0,
         "spend:org:org1": 5.0,
     }
+    fake_cache.redis_cache.async_increment.assert_not_awaited()
 
 
 @pytest.mark.asyncio
@@ -772,6 +776,108 @@ async def test_increment_spend_counters_zero_cost_is_noop_finalizes_reservation(
 
     assert reservation == {"finalized": True}
     assert fake_cache.redis_cache.async_increment.called is False
+    fake_cache.redis_cache.async_increment_pipeline.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_increment_spend_counters_pipelines_all_scopes_in_one_redis_call(
+    monkeypatch,
+):
+    """Every scope's increment must go out in a single async_increment_pipeline
+    call, not one INCRBYFLOAT round-trip per scope."""
+    counter_cache = ps.DualCache()
+    fake_redis = AsyncMock()
+    fake_redis.async_get_cache = AsyncMock(return_value=1.0)  # counters warm
+
+    async def _pipeline(increment_list, **_):
+        return [1.5] * len(increment_list)
+
+    fake_redis.async_increment_pipeline = AsyncMock(side_effect=_pipeline)
+    fake_redis.async_increment = AsyncMock()
+    fake_redis.get_ttl = MagicMock(return_value=None)
+    counter_cache.redis_cache = fake_redis
+    monkeypatch.setattr(ps, "spend_counter_cache", counter_cache)
+    monkeypatch.setattr(ps, "user_api_key_cache", ps.DualCache())
+    monkeypatch.setattr(ps, "prisma_client", None)
+
+    await ps.increment_spend_counters(
+        token="hashed",
+        team_id="team-1",
+        user_id="user-1",
+        response_cost=0.5,
+        org_id="org-1",
+        end_user_id="eu-1",
+        tags=["tag-a", "tag-b"],
+    )
+
+    fake_redis.async_increment_pipeline.assert_awaited_once()
+    assert fake_redis.async_increment.await_count == 0
+    increment_list = fake_redis.async_increment_pipeline.await_args.kwargs["increment_list"]
+    expected_keys = {
+        "spend:key:hashed",
+        "spend:team:team-1",
+        "spend:team_member:user-1:team-1",
+        "spend:user:user-1",
+        "spend:end_user:eu-1",
+        "spend:tag:tag-a",
+        "spend:tag:tag-b",
+        "spend:org:org-1",
+    }
+    assert {op["key"] for op in increment_list} == expected_keys
+    assert all(op["increment_value"] == 0.5 for op in increment_list)
+    for key in expected_keys:
+        assert counter_cache.in_memory_cache.get_cache(key=key) == 1.5
+
+
+@pytest.mark.asyncio
+async def test_increment_spend_counters_pipeline_failure_invalidates_all_counters(
+    monkeypatch,
+):
+    """A failing pipeline must invalidate every pending counter so the next
+    request reseeds from the DB (which already holds this request's cost)
+    instead of trusting a value the write may have partially applied."""
+    from redis.exceptions import MaxConnectionsError
+
+    counter_cache = ps.DualCache()
+    pending_keys = (
+        "spend:key:hashed",
+        "spend:team:team-1",
+        "spend:team_member:user-1:team-1",
+        "spend:user:user-1",
+        "spend:end_user:eu-1",
+        "spend:tag:tag-a",
+        "spend:tag:tag-b",
+        "spend:org:org-1",
+    )
+    for key in pending_keys:
+        counter_cache.in_memory_cache.set_cache(key=key, value=1.0)
+    fake_redis = AsyncMock()
+    fake_redis.async_get_cache = AsyncMock(return_value=1.0)  # counters warm
+    fake_redis.async_increment_pipeline = AsyncMock(side_effect=MaxConnectionsError())
+    fake_redis.async_increment = AsyncMock()
+    fake_redis.async_delete_cache = AsyncMock()
+    fake_redis.get_ttl = MagicMock(return_value=None)
+    counter_cache.redis_cache = fake_redis
+    monkeypatch.setattr(ps, "spend_counter_cache", counter_cache)
+    monkeypatch.setattr(ps, "user_api_key_cache", ps.DualCache())
+    monkeypatch.setattr(ps, "prisma_client", None)
+
+    with pytest.raises(MaxConnectionsError):
+        await ps.increment_spend_counters(
+            token="hashed",
+            team_id="team-1",
+            user_id="user-1",
+            response_cost=0.5,
+            org_id="org-1",
+            end_user_id="eu-1",
+            tags=["tag-a", "tag-b"],
+        )
+
+    assert fake_redis.async_increment.await_count == 0
+    deleted_keys = {call.kwargs["key"] for call in fake_redis.async_delete_cache.await_args_list}
+    assert deleted_keys == set(pending_keys)
+    for key in pending_keys:
+        assert counter_cache.in_memory_cache.get_cache(key=key) is None
 
 
 # ---------------------------------------------------------------------------
@@ -781,9 +887,7 @@ async def test_increment_spend_counters_zero_cost_is_noop_finalizes_reservation(
 
 @pytest.mark.asyncio
 async def test_reconcile_budget_reservation_for_counter_update_returns_empty_set_when_none():
-    result = await ps._reconcile_budget_reservation_for_counter_update(
-        budget_reservation=None, response_cost=1.0
-    )
+    result = await ps._reconcile_budget_reservation_for_counter_update(budget_reservation=None, response_cost=1.0)
     assert result == set()
 
 
@@ -818,179 +922,151 @@ async def test_reconcile_budget_reservation_for_counter_update_failure_invalidat
 
 
 # ---------------------------------------------------------------------------
-# _increment_end_user_and_tag_spend_counters
+# _prepare_end_user_and_tag_spend_increments
 # ---------------------------------------------------------------------------
 
 
 @pytest.mark.asyncio
-async def test_increment_end_user_and_tag_spend_counters_increments_each_unique_tag(
+async def test_prepare_end_user_and_tag_spend_increments_returns_each_unique_tag(
     monkeypatch,
 ):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=None, redis_increment_value=3.0
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_value=1.0)
     fake_user_cache = _make_user_api_key_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
-    await ps._increment_end_user_and_tag_spend_counters(
+    pending = await ps._prepare_end_user_and_tag_spend_increments(
         end_user_id="eu1",
         tags=["a", "b", "a", "", None],
         response_cost=3.0,
         reserved_counter_keys=set(),
     )
 
-    observed = {
-        "increment_calls": fake_cache.redis_cache.async_increment.call_count,
-        "in_memory_set_calls": fake_cache.in_memory_cache.set_cache.call_count,
-        "called": fake_cache.redis_cache.async_increment.called,
-    }
-    assert normalize(observed) == {
-        "increment_calls": 3,
-        "in_memory_set_calls": 3,
-        "called": True,
+    assert {item.counter_key for item in pending} == {
+        "spend:end_user:eu1",
+        "spend:tag:a",
+        "spend:tag:b",
     }
+    assert all(item.increment == 3.0 for item in pending)
 
 
 @pytest.mark.asyncio
-async def test_increment_end_user_and_tag_spend_counters_no_end_user_no_tags_invalid_input_noop(
+async def test_prepare_end_user_and_tag_spend_increments_no_end_user_no_tags_invalid_input_noop(
     monkeypatch,
 ):
     fake_cache = _make_spend_counter_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
-    await ps._increment_end_user_and_tag_spend_counters(
+    pending = await ps._prepare_end_user_and_tag_spend_increments(
         end_user_id=None,
         tags=None,
         response_cost=1.0,
         reserved_counter_keys=set(),
     )
 
+    assert pending == ()
     assert fake_cache.redis_cache.async_increment.called is False
 
 
 # ---------------------------------------------------------------------------
-# _increment_org_spend_counter
+# _prepare_org_spend_increment
 # ---------------------------------------------------------------------------
 
 
 @pytest.mark.asyncio
-async def test_increment_org_spend_counter_increments_when_org_present(monkeypatch):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=None, redis_increment_value=10.0
-    )
+async def test_prepare_org_spend_increment_returns_pending_when_org_present(monkeypatch):
+    fake_cache = _make_spend_counter_cache(redis_get_value=1.0)
     fake_user_cache = _make_user_api_key_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
-    await ps._increment_org_spend_counter(
+    pending = await ps._prepare_org_spend_increment(
         org_id="org-1",
         response_cost=10.0,
         reserved_counter_keys=set(),
     )
 
-    observed = {
-        "increment_called": fake_cache.redis_cache.async_increment.called,
-        "increment_calls": fake_cache.redis_cache.async_increment.call_count,
-        "counter_key_arg": fake_cache.redis_cache.async_increment.call_args.kwargs[
-            "key"
-        ],
-    }
-    assert normalize(observed) == {
-        "increment_called": True,
-        "increment_calls": 1,
-        "counter_key_arg": "spend:org:org-1",
-    }
+    assert len(pending) == 1
+    assert pending[0].counter_key == "spend:org:org-1"
+    assert pending[0].increment == 10.0
 
 
 @pytest.mark.asyncio
-async def test_increment_org_spend_counter_no_org_is_noop_invalid_id(monkeypatch):
+async def test_prepare_org_spend_increment_no_org_is_noop_invalid_id(monkeypatch):
     fake_cache = _make_spend_counter_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
-    await ps._increment_org_spend_counter(
+    pending = await ps._prepare_org_spend_increment(
         org_id=None,
         response_cost=1.0,
         reserved_counter_keys=set(),
     )
 
+    assert pending == ()
     assert fake_cache.redis_cache.async_increment.called is False
 
 
 # ---------------------------------------------------------------------------
-# _init_and_increment_unreserved_spend_counter
+# _prepare_unreserved_spend_counter_increment
 # ---------------------------------------------------------------------------
 
 
 @pytest.mark.asyncio
-async def test_init_and_increment_unreserved_spend_counter_skips_reserved_keys(
+async def test_prepare_unreserved_spend_counter_increment_skips_reserved_keys(
     monkeypatch,
 ):
     fake_cache = _make_spend_counter_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
-    await ps._init_and_increment_unreserved_spend_counter(
+    pending = await ps._prepare_unreserved_spend_counter_increment(
         counter_key="spend:tag:x",
         source_cache_key="tag:x",
         increment=1.0,
         reserved_counter_keys={"spend:tag:x"},
     )
 
+    assert pending is None
     assert fake_cache.redis_cache.async_increment.called is False
 
 
 @pytest.mark.asyncio
-async def test_init_and_increment_unreserved_spend_counter_proceeds_when_not_reserved(
+async def test_prepare_unreserved_spend_counter_increment_proceeds_when_not_reserved(
     monkeypatch,
 ):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=None, redis_increment_value=2.0
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_value=None)
     fake_user_cache = _make_user_api_key_cache()
+    reseed = AsyncMock(return_value=None)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", reseed)
 
-    await ps._init_and_increment_unreserved_spend_counter(
+    pending = await ps._prepare_unreserved_spend_counter_increment(
         counter_key="spend:tag:y",
         source_cache_key="tag:y",
         increment=2.0,
         reserved_counter_keys=set(),
     )
 
-    observed = {
-        "increment_called": fake_cache.redis_cache.async_increment.called,
-        "redis_get_called": fake_cache.redis_cache.async_get_cache.called,
-        "reseed_consulted": True,
-    }
-    assert observed == {
-        "increment_called": True,
-        "redis_get_called": True,
-        "reseed_consulted": True,
-    }
+    assert pending is not None
+    assert pending.counter_key == "spend:tag:y"
+    assert pending.increment == 2.0
+    assert fake_cache.redis_cache.async_get_cache.called is True
+    assert reseed.called is True
 
 
 # ---------------------------------------------------------------------------
-# _init_and_increment_spend_counter
+# _prepare_spend_counter_increment
 # ---------------------------------------------------------------------------
 
 
 @pytest.mark.asyncio
-async def test_init_and_increment_spend_counter_warm_cache_skips_reseed(monkeypatch):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=11.0, redis_increment_value=14.0
-    )
+async def test_prepare_spend_counter_increment_warm_cache_skips_reseed(monkeypatch):
+    fake_cache = _make_spend_counter_cache(redis_get_value=11.0)
     fake_user_cache = _make_user_api_key_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
@@ -998,12 +1074,14 @@ async def test_init_and_increment_spend_counter_warm_cache_skips_reseed(monkeypa
     reseed = AsyncMock(return_value=None)
     monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", reseed)
 
-    await ps._init_and_increment_spend_counter(
+    pending = await ps._prepare_spend_counter_increment(
         counter_key="spend:key:k",
         source_cache_key="k",
         increment=3.0,
     )
 
+    assert pending.counter_key == "spend:key:k"
+    assert pending.increment == 3.0
     observed = {
         "reseed_called": reseed.called,
         "increment_called": fake_cache.redis_cache.async_increment.called,
@@ -1011,23 +1089,21 @@ async def test_init_and_increment_spend_counter_warm_cache_skips_reseed(monkeypa
     }
     assert normalize(observed) == {
         "reseed_called": False,
-        "increment_called": True,
+        "increment_called": False,
         "in_memory_seeded_from_redis": True,
     }
 
 
 # ---------------------------------------------------------------------------
-# _init_and_increment_window_spend_counter
+# _prepare_window_spend_counter_increment
 # ---------------------------------------------------------------------------
 
 
 @pytest.mark.asyncio
-async def test_init_and_increment_window_spend_counter_increments_when_initialized(
+async def test_prepare_window_spend_counter_increment_returns_pending_when_initialized(
     monkeypatch,
 ):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=0.0, redis_increment_value=5.0
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_value=0.0)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
     monkeypatch.setattr(
@@ -1036,7 +1112,7 @@ async def test_init_and_increment_window_spend_counter_increments_when_initializ
         AsyncMock(return_value=0.0),
     )
 
-    await ps._init_and_increment_window_spend_counter(
+    pending = await ps._prepare_window_spend_counter_increment(
         counter_key="spend:key:k:window:1d",
         entity_type="Key",
         entity_id="k",
@@ -1045,26 +1121,19 @@ async def test_init_and_increment_window_spend_counter_increments_when_initializ
         increment=5.0,
     )
 
-    observed = {
-        "redis_increment_called": fake_cache.redis_cache.async_increment.called,
-        "increment_calls": fake_cache.redis_cache.async_increment.call_count,
-        "in_memory_set_calls": fake_cache.in_memory_cache.set_cache.call_count,
-    }
-    assert normalize(observed) == {
-        "redis_increment_called": True,
-        "increment_calls": 1,
-        "in_memory_set_calls": 2,
-    }
+    assert pending is not None
+    assert pending.counter_key == "spend:key:k:window:1d"
+    assert pending.increment == 5.0
 
 
 @pytest.mark.asyncio
-async def test_init_and_increment_window_spend_counter_missing_window_start_invalid_skips(
+async def test_prepare_window_spend_counter_increment_missing_window_start_invalid_skips(
     monkeypatch,
 ):
     fake_cache = _make_spend_counter_cache()
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
-    await ps._init_and_increment_window_spend_counter(
+    pending = await ps._prepare_window_spend_counter_increment(
         counter_key="spend:key:k:window:1d",
         entity_type="Key",
         entity_id="k",
@@ -1073,9 +1142,58 @@ async def test_init_and_increment_window_spend_counter_missing_window_start_inva
         increment=5.0,
     )
 
+    assert pending is None
     assert fake_cache.redis_cache.async_increment.called is False
 
 
+# ---------------------------------------------------------------------------
+# _apply_spend_counter_increments
+# ---------------------------------------------------------------------------
+
+
+def _two_pending_increments() -> tuple[ps._PendingSpendIncrement, ...]:
+    return (
+        ps._PendingSpendIncrement(counter_key="spend:key:k", increment=1.5),
+        ps._PendingSpendIncrement(counter_key="spend:team:t", increment=1.5),
+    )
+
+
+@pytest.mark.asyncio
+async def test_apply_spend_counter_increments_open_breaker_invalidates_and_returns(monkeypatch):
+    """An open Redis circuit breaker is a known, already-logged state, not a per-request tracking failure.
+
+    Re-raising the refusal sent every request through the cost callback's error path, which
+    logged an ERROR and fired the failed-tracking alert once per request for the whole outage.
+    """
+    from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
+
+    fake_cache = _make_spend_counter_cache()
+    fake_cache.redis_cache.async_increment_pipeline = AsyncMock(
+        side_effect=RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+    )
+    monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
+
+    await ps._apply_spend_counter_increments(_two_pending_increments())
+
+    deleted_keys = sorted(call.kwargs["key"] for call in fake_cache.in_memory_cache.delete_cache.call_args_list)
+    assert deleted_keys == ["spend:key:k", "spend:team:t"]
+    fake_cache.in_memory_cache.set_cache.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_apply_spend_counter_increments_other_redis_error_invalidates_and_raises(monkeypatch):
+    fake_cache = _make_spend_counter_cache()
+    fake_cache.redis_cache.async_increment_pipeline = AsyncMock(side_effect=ConnectionError("redis down"))
+    monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
+
+    with pytest.raises(ConnectionError, match="redis down"):
+        await ps._apply_spend_counter_increments(_two_pending_increments())
+
+    deleted_keys = sorted(call.kwargs["key"] for call in fake_cache.in_memory_cache.delete_cache.call_args_list)
+    assert deleted_keys == ["spend:key:k", "spend:team:t"]
+    fake_cache.in_memory_cache.set_cache.assert_not_called()
+
+
 # ---------------------------------------------------------------------------
 # _ensure_spend_counter_initialized
 # ---------------------------------------------------------------------------
@@ -1114,16 +1232,12 @@ async def test_ensure_spend_counter_initialized_warm_skips_reseed_and_source(
 async def test_ensure_spend_counter_initialized_cold_seeds_from_source_cache(
     monkeypatch,
 ):
-    fake_cache = _make_spend_counter_cache(
-        redis_get_value=None, redis_increment_value=7.0
-    )
+    fake_cache = _make_spend_counter_cache(redis_get_value=None, redis_increment_value=7.0)
     fake_user_cache = _make_user_api_key_cache(get_value={"spend": 7.0})
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
     monkeypatch.setattr(ps, "prisma_client", None)
-    monkeypatch.setattr(
-        ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None)
-    )
+    monkeypatch.setattr(ps.SpendCounterReseed, "coalesced", AsyncMock(return_value=None))
 
     await ps._ensure_spend_counter_initialized(
         counter_key="spend:user:u",
@@ -1163,9 +1277,7 @@ async def test_get_source_cache_base_spend_reads_first_hit_from_list(monkeypatch
     fake_user_cache.async_get_cache = AsyncMock(side_effect=_get)
     monkeypatch.setattr(ps, "user_api_key_cache", fake_user_cache)
 
-    result = await ps._get_source_cache_base_spend(
-        source_cache_key=["miss", "hit-obj", "miss2"]
-    )
+    result = await ps._get_source_cache_base_spend(source_cache_key=["miss", "hit-obj", "miss2"])
 
     observed = {
         "result": result,
@@ -1294,9 +1406,7 @@ async def test_increment_spend_counter_cache_redis_path_returns_new_value(monkey
     fake_cache = _make_spend_counter_cache(redis_increment_value=44.0)
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
-    result = await ps._increment_spend_counter_cache(
-        counter_key="spend:key:k", increment=4.0
-    )
+    result = await ps._increment_spend_counter_cache(counter_key="spend:key:k", increment=4.0)
 
     observed = {
         "result": result,
@@ -1314,15 +1424,11 @@ async def test_increment_spend_counter_cache_redis_path_returns_new_value(monkey
 async def test_increment_spend_counter_cache_redis_error_raises_and_invalidates(
     monkeypatch,
 ):
-    fake_cache = _make_spend_counter_cache(
-        redis_increment_side_effect=RuntimeError("incr fail")
-    )
+    fake_cache = _make_spend_counter_cache(redis_increment_side_effect=RuntimeError("incr fail"))
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
     with pytest.raises(RuntimeError):
-        await ps._increment_spend_counter_cache(
-            counter_key="spend:key:k", increment=1.0
-        )
+        await ps._increment_spend_counter_cache(counter_key="spend:key:k", increment=1.0)
 
     assert fake_cache.in_memory_cache.delete_cache.called is True
     assert fake_cache.redis_cache.async_delete_cache.called is True
@@ -1343,9 +1449,7 @@ async def test_invalidate_spend_counter_deletes_in_memory_and_redis(monkeypatch)
     observed = {
         "in_memory_delete_called": fake_cache.in_memory_cache.delete_cache.called,
         "redis_delete_called": fake_cache.redis_cache.async_delete_cache.called,
-        "delete_args_key": fake_cache.redis_cache.async_delete_cache.call_args.kwargs[
-            "key"
-        ],
+        "delete_args_key": fake_cache.redis_cache.async_delete_cache.call_args.kwargs["key"],
     }
     assert normalize(observed) == {
         "in_memory_delete_called": True,
@@ -1357,9 +1461,7 @@ async def test_invalidate_spend_counter_deletes_in_memory_and_redis(monkeypatch)
 @pytest.mark.asyncio
 async def test_invalidate_spend_counter_swallows_redis_failure_no_raise(monkeypatch):
     fake_cache = _make_spend_counter_cache()
-    fake_cache.redis_cache.async_delete_cache = AsyncMock(
-        side_effect=RuntimeError("redis down")
-    )
+    fake_cache.redis_cache.async_delete_cache = AsyncMock(side_effect=RuntimeError("redis down"))
     monkeypatch.setattr(ps, "spend_counter_cache", fake_cache)
 
     await ps._invalidate_spend_counter(counter_key="spend:key:k")
diff --git a/tests/test_litellm/proxy/proxy_server/test_team_model_name_translation.py b/tests/test_litellm/proxy/proxy_server/test_team_model_name_translation.py
index 0fb9b1a6d88..300cac5cdb2 100644
--- a/tests/test_litellm/proxy/proxy_server/test_team_model_name_translation.py
+++ b/tests/test_litellm/proxy/proxy_server/test_team_model_name_translation.py
@@ -880,7 +880,7 @@ async def test_v1_models_translates_team_model_for_access_group_key(monkeypatch)
     router.get_model_names.return_value = ["model_name_teamX_uuid9"]
     router.get_model_access_groups.return_value = {"grp-a": ["model_name_teamX_uuid9"]}
     router.get_fully_blocked_model_names.return_value = set()
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
     router.model_list = [team_dep]
     router.get_model_list.return_value = [team_dep]
 
@@ -922,7 +922,7 @@ async def test_v1_models_keeps_internal_names_when_public_name_flag_disabled(
     router.get_model_names.return_value = ["model_name_teamX_uuid9"]
     router.get_model_access_groups.return_value = {"grp-a": ["model_name_teamX_uuid9"]}
     router.get_fully_blocked_model_names.return_value = set()
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
     router.model_list = [team_dep]
     router.get_model_list.return_value = [team_dep]
 
@@ -957,7 +957,7 @@ async def test_v1_models_translates_team_model_with_metadata(monkeypatch):
     router.get_model_names.return_value = ["model_name_teamX_uuid9"]
     router.get_model_access_groups.return_value = {"grp-a": ["model_name_teamX_uuid9"]}
     router.get_fully_blocked_model_names.return_value = set()
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
     router.model_list = [team_dep]
     router.get_model_list.return_value = [team_dep]
     router.get_model_group_info.return_value = None
@@ -1003,7 +1003,7 @@ async def test_v1_models_metadata_fallbacks_use_internal_routing_key(monkeypatch
     router.get_model_names.return_value = ["model_name_teamX_uuid9"]
     router.get_model_access_groups.return_value = {"grp-a": ["model_name_teamX_uuid9"]}
     router.get_fully_blocked_model_names.return_value = set()
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
     router.model_list = [team_dep]
     router.get_model_list.return_value = [team_dep]
     # Fallbacks are keyed on the internal routing name, as the router stores them.
@@ -1060,7 +1060,7 @@ async def test_v1_models_metadata_does_not_leak_other_team_fallbacks(monkeypatch
     router.get_model_names.return_value = ["model_name_teamX_uuid9"]
     router.get_model_access_groups.return_value = {"grp-a": ["model_name_teamX_uuid9"]}
     router.get_fully_blocked_model_names.return_value = set()
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
     router.model_list = [team_x, team_y]
     router.get_model_list.return_value = [team_x, team_y]
     router.fallbacks = [
@@ -1315,7 +1315,7 @@ def test_translate_team_model_names_for_listing_respects_legacy_flag():
 def _public_named_router(*team_rows: dict) -> MagicMock:
     router = MagicMock()
     router.get_model_list.return_value = list(team_rows)
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
     return router
 
 
diff --git a/tests/test_litellm/proxy/spend_tracking/test_budget_reservation.py b/tests/test_litellm/proxy/spend_tracking/test_budget_reservation.py
index de6c7c2a40a..ee062b14b96 100644
--- a/tests/test_litellm/proxy/spend_tracking/test_budget_reservation.py
+++ b/tests/test_litellm/proxy/spend_tracking/test_budget_reservation.py
@@ -1,13 +1,24 @@
+import json
+import math
 from typing import Final
 
 import pytest
 
-import litellm.proxy.proxy_server as proxy_server
+import litellm
 from litellm.caching import DualCache
+from litellm.proxy import proxy_server
 from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.common_utils.user_api_key_cache import UserApiKeyCache
-from litellm.proxy.spend_tracking.budget_reservation import estimate_request_max_cost, reserve_budget_for_request
+from litellm.proxy.spend_tracking.budget_reservation import (
+    count_request_input_tokens,
+    estimate_request_max_cost,
+    reserve_budget_for_request,
+)
 from litellm.proxy.utils import ProxyLogging
+from litellm.router import Router
+from litellm.rust_bridge import bindings, configuration
+from litellm.rust_bridge import token_counter as rust_token_counter
+from litellm.types.router import Deployment, LiteLLM_Params, ModelInfo
 
 TOKEN_COUNTING_ROUTES: Final = (
     "/responses/input_tokens",
@@ -56,6 +67,16 @@ async def test_non_exempt_llm_route_still_reserves_budget():
     assert reservation["reserved_cost"] > 0
 
 
+@pytest.mark.asyncio
+async def test_reservation_carries_the_admission_input_token_count():
+    reservation: Final = await _reserve("/v1/responses")
+    expected: Final = litellm.token_counter(model="gpt-4o", text="hello")
+
+    assert reservation is not None
+    assert expected > 0
+    assert reservation["input_tokens"] == expected
+
+
 ANTHROPIC_MESSAGES: Final = [{"role": "user", "content": "hello!!!"}]
 COUNT_TOKENS_REQUESTS: Final[tuple[tuple[str, dict[str, object]], ...]] = (
     ("/v1/messages/count_tokens", {"model": "claude-sonnet-5", "messages": ANTHROPIC_MESSAGES}),
@@ -139,3 +160,172 @@ def test_bedrock_converse_body_reserves_the_prompt_not_the_context_window():
     )
     assert converse_cost is not None and invoke_cost is not None
     assert invoke_cost < converse_cost < 2 * invoke_cost
+
+
+def _tiered_deployment(input_cost_per_token: float) -> Deployment:
+    return Deployment(
+        model_name="tiered-group",
+        litellm_params=LiteLLM_Params(model="dashscope/qwen3-max", api_key="sk-fake"),
+        model_info=ModelInfo(
+            id="tiered-deployment",
+            max_output_tokens=1000,
+            tiered_pricing=[
+                {
+                    "input_cost_per_token": input_cost_per_token,
+                    "output_cost_per_token": input_cost_per_token,
+                    "range": [0, 128000],
+                }
+            ],
+        ),
+    )
+
+
+TIERED_BODY: Final = {"model": "tiered-group", "messages": [{"role": "user", "content": "hello"}], "max_tokens": 10}
+
+
+def test_repeated_estimates_reuse_cached_model_cost_info() -> None:
+    router: Final = Router(model_list=[_tiered_deployment(1e-06).model_dump()])
+    first: Final = estimate_request_max_cost(request_body=TIERED_BODY, route="/chat/completions", llm_router=router)
+    hits_before: Final = router.cached_deployment_model_info.cache_info().hits
+
+    second: Final = estimate_request_max_cost(request_body=TIERED_BODY, route="/chat/completions", llm_router=router)
+
+    assert second == first
+    assert router.cached_deployment_model_info.cache_info().hits == hits_before + 1
+
+
+def test_deployment_pricing_update_invalidates_cached_estimate() -> None:
+    router: Final = Router(model_list=[_tiered_deployment(1e-06).model_dump()])
+    before: Final = estimate_request_max_cost(request_body=TIERED_BODY, route="/chat/completions", llm_router=router)
+    assert before is not None
+
+    router.upsert_deployment(_tiered_deployment(1e-03))
+
+    after: Final = estimate_request_max_cost(request_body=TIERED_BODY, route="/chat/completions", llm_router=router)
+    assert after is not None
+    assert math.isclose(after, before * 1000)
+
+
+ANTHROPIC_TOKENIZER_MODEL: Final = "claude-sonnet-4-5-20250929"
+RUST_COUNTED_BODY: Final = {"model": ANTHROPIC_TOKENIZER_MODEL, "max_tokens": 16, "messages": ANTHROPIC_MESSAGES}
+RUST_INPUT_TOKENS: Final = 4_321
+
+
+class _FakeDeclined(Exception):
+    pass
+
+
+class _FakeUpstream(Exception):
+    pass
+
+
+class _FakeNative:
+    RustBridgeDeclined = _FakeDeclined
+    RustUpstreamError = _FakeUpstream
+
+
+class _RecordingCounter:
+    bodies: Final[list[bytes]] = []
+
+    def __init__(self, tokenizer_json: str) -> None:
+        pass
+
+    async def acount_request(self, body: bytes) -> object:
+        self.bodies.append(body)
+        return {"model": ANTHROPIC_TOKENIZER_MODEL, "input_tokens": RUST_INPUT_TOKENS}
+
+
+class _DecliningCounter:
+    def __init__(self, tokenizer_json: str) -> None:
+        pass
+
+    async def acount_request(self, body: bytes) -> object:
+        raise _FakeDeclined("unsupported content block")
+
+
+@pytest.fixture
+def rust_counter(monkeypatch: pytest.MonkeyPatch):
+    monkeypatch.setattr(bindings, "get_native_bridge", lambda: _FakeNative())
+    rust_token_counter._anthropic_counter.cache_clear()
+    configuration.reset_rust_configuration()
+    _RecordingCounter.bodies.clear()
+    yield
+    rust_token_counter.TOKEN_COUNTER.reset()
+    rust_token_counter._anthropic_counter.cache_clear()
+    configuration.reset_rust_configuration()
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("route", "request_body"),
+    (
+        ("/v1/messages", RUST_COUNTED_BODY),
+        ("/v1/chat/completions", {"model": ANTHROPIC_TOKENIZER_MODEL, "messages": ANTHROPIC_MESSAGES}),
+        ("/v1/completions", {"model": ANTHROPIC_TOKENIZER_MODEL, "prompt": "hi"}),
+        ("/v1/responses", {"model": ANTHROPIC_TOKENIZER_MODEL, "input": "hi"}),
+        ("/v1/embeddings", {"model": ANTHROPIC_TOKENIZER_MODEL, "input": ["hi"]}),
+        ("/v1/rerank", {"model": ANTHROPIC_TOKENIZER_MODEL, "query": "hi", "documents": ["a"]}),
+    ),
+)
+async def test_rust_count_replaces_python_tokenizing_on_every_llm_route(
+    rust_counter: None, route: str, request_body: dict
+) -> None:
+    litellm.rust(True)
+    rust_token_counter.TOKEN_COUNTER.override(_RecordingCounter)
+    raw_body: Final = json.dumps(request_body).encode()
+
+    counts: Final = await count_request_input_tokens(
+        request_body=request_body, route=route, llm_router=None, raw_body=raw_body
+    )
+
+    assert dict(counts) == {ANTHROPIC_TOKENIZER_MODEL: RUST_INPUT_TOKENS}
+    assert _RecordingCounter.bodies == [raw_body]
+
+
+@pytest.mark.asyncio
+async def test_rust_decline_falls_back_to_python_count(rust_counter: None) -> None:
+    litellm.rust(True)
+    rust_token_counter.TOKEN_COUNTER.override(_DecliningCounter)
+    python_counts: Final = await count_request_input_tokens(
+        request_body=RUST_COUNTED_BODY, route="/v1/messages", llm_router=None
+    )
+
+    counts: Final = await count_request_input_tokens(
+        request_body=RUST_COUNTED_BODY,
+        route="/v1/messages",
+        llm_router=None,
+        raw_body=json.dumps(RUST_COUNTED_BODY).encode(),
+    )
+
+    assert dict(counts) == dict(python_counts)
+    assert counts[ANTHROPIC_TOKENIZER_MODEL] != RUST_INPUT_TOKENS
+
+
+@pytest.mark.asyncio
+async def test_disabled_rust_never_sees_the_raw_body(rust_counter: None) -> None:
+    litellm.rust(False)
+    rust_token_counter.TOKEN_COUNTER.override(_RecordingCounter)
+
+    counts: Final = await count_request_input_tokens(
+        request_body=RUST_COUNTED_BODY,
+        route="/v1/messages",
+        llm_router=None,
+        raw_body=json.dumps(RUST_COUNTED_BODY).encode(),
+    )
+
+    assert _RecordingCounter.bodies == []
+    assert counts[ANTHROPIC_TOKENIZER_MODEL] != RUST_INPUT_TOKENS
+
+
+@pytest.mark.asyncio
+async def test_non_anthropic_tokenizer_models_stay_in_python(rust_counter: None) -> None:
+    litellm.rust(True)
+    rust_token_counter.TOKEN_COUNTER.override(_RecordingCounter)
+    body: Final = {"model": "gpt-4o", "messages": ANTHROPIC_MESSAGES}
+
+    counts: Final = await count_request_input_tokens(
+        request_body=body, route="/v1/chat/completions", llm_router=None, raw_body=json.dumps(body).encode()
+    )
+
+    assert _RecordingCounter.bodies == []
+    assert counts["gpt-4o"] != RUST_INPUT_TOKENS
diff --git a/tests/test_litellm/proxy/spend_tracking/test_budget_reservation_redis_failure.py b/tests/test_litellm/proxy/spend_tracking/test_budget_reservation_redis_failure.py
index c123eeeed36..6165af4920d 100644
--- a/tests/test_litellm/proxy/spend_tracking/test_budget_reservation_redis_failure.py
+++ b/tests/test_litellm/proxy/spend_tracking/test_budget_reservation_redis_failure.py
@@ -41,6 +41,15 @@ class _FlakyRedisCache:
         self._store[key] = float(value)
         return True
 
+    async def async_increment_pipeline(self, increment_list, **kwargs):
+        results = []
+        for op in increment_list:
+            results.append(await self.async_increment(op["key"], op["increment_value"]))
+        return results
+
+    def get_ttl(self, **kwargs):
+        return None
+
 
 @pytest.mark.asyncio
 async def test_direct_increment_runs_when_reservation_reconcile_hits_redis_failure(
diff --git a/tests/test_litellm/proxy/spend_tracking/test_key_metadata_recovery.py b/tests/test_litellm/proxy/spend_tracking/test_key_metadata_recovery.py
index 7a80319239d..89be341c87b 100644
--- a/tests/test_litellm/proxy/spend_tracking/test_key_metadata_recovery.py
+++ b/tests/test_litellm/proxy/spend_tracking/test_key_metadata_recovery.py
@@ -1,21 +1,60 @@
+import asyncio
+import time
 from collections.abc import Sequence
+from datetime import datetime, timedelta
 from types import SimpleNamespace
 from unittest.mock import AsyncMock, MagicMock
 
 import pytest
 from prisma.errors import PrismaError
 
+from litellm.caching.in_memory_cache import InMemoryCache
+from litellm.constants import (
+    SPEND_LOG_KEY_METADATA_CACHE_TTL,
+    SPEND_LOG_KEY_METADATA_MISS_CACHE_TTL,
+    SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS,
+)
 from litellm.proxy.spend_tracking.key_metadata_recovery import (
     fill_missing_api_key_aliases,
     recover_double_hashed_key_metadata,
+    recover_key_metadata_from_spend_logs,
 )
 from litellm.proxy.utils import hash_token
 
 
-def _digest_row(digest: str, key_alias: str, team_id: str | None, user_id: str | None) -> dict[str, str | None]:
+def _digest_row(digest: str, key_alias: str | None, team_id: str | None, user_id: str | None) -> dict[str, str | None]:
     return {"digest": digest, "key_alias": key_alias, "team_id": team_id, "user_id": user_id}
 
 
+def _query_raw_spend_logs(rows: Sequence[dict[str, str | None]]) -> AsyncMock:
+    async def query_raw(sql: str, *params: object) -> list[dict[str, str | None]]:
+        if '"LiteLLM_SpendLogs"' in sql:
+            return list(rows)
+        raise AssertionError(f"unexpected query: {sql}")
+
+    return AsyncMock(side_effect=query_raw)
+
+
+def _spend_log_row(digest: str, key_alias: str | None, team_id: str | None, user_id: str | None) -> dict[str, str | None]:
+    return {
+        "digest": digest,
+        "first_alias": key_alias,
+        "last_alias": key_alias,
+        "first_team": team_id,
+        "last_team": team_id,
+        "first_owner": user_id,
+        "last_owner": user_id,
+    }
+
+
+def _spend_log_transaction(mock_prisma: MagicMock, query_raw: AsyncMock) -> AsyncMock:
+    transaction = MagicMock()
+    transaction.execute_raw = AsyncMock(return_value=0)
+    transaction.query_raw = query_raw
+    mock_prisma.db.tx.return_value.__aenter__.return_value = transaction
+    return query_raw
+
+
 def _query_raw_by_table(
     active_rows: Sequence[dict[str, str | None]],
     deleted_rows: Sequence[dict[str, str | None]],
@@ -218,3 +257,334 @@ async def test_fill_missing_api_key_aliases_skips_named_keys_that_have_no_email(
 
     assert filled == rows
     mock_prisma.db.query_raw.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_resolves_session_token_from_metadata():
+    session_digest = hash_token("cli-session-repro-user-6852")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(
+        mock_prisma,
+        _query_raw_spend_logs(
+            [_spend_log_row(session_digest, "cli-session-repro-user-6852", None, "repro-user-6852")]
+        ),
+    )
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {session_digest}, window, cache=InMemoryCache())
+
+    assert result[session_digest]["key_alias"] == "cli-session-repro-user-6852"
+    assert result[session_digest]["user_id"] == "repro-user-6852"
+    ((_, digests, start, end),) = [call.args for call in query_raw.call_args_list]
+    assert digests == [session_digest]
+    assert (start, end) == window
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_skips_query_when_no_missing_keys():
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, AsyncMock(return_value=[]))
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, set(), window, cache=InMemoryCache())
+
+    assert result == {}
+    query_raw.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_returns_empty_on_prisma_error():
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, AsyncMock(side_effect=PrismaError("db down")))
+
+    result = await recover_key_metadata_from_spend_logs(
+        mock_prisma, {hash_token("cli-session-x")}, window, cache=InMemoryCache()
+    )
+
+    assert result == {}
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_ignores_foreign_and_all_null_rows():
+    wanted = hash_token("cli-session-wanted")
+    all_null = hash_token("cli-session-null")
+    foreign = hash_token("cli-session-foreign")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(
+        mock_prisma,
+        _query_raw_spend_logs(
+            [
+                _spend_log_row(wanted, "kept-alias", None, "owner-1"),
+                _spend_log_row(all_null, None, None, None),
+                _spend_log_row(foreign, "foreign-alias", None, "owner-2"),
+            ]
+        ),
+    )
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {wanted, all_null}, window, cache=InMemoryCache())
+
+    assert set(result) == {wanted}
+    assert result[wanted]["key_alias"] == "kept-alias"
+    assert result[wanted]["user_id"] == "owner-1"
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_skips_non_sha256_keys():
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, AsyncMock(return_value=[]))
+
+    result = await recover_key_metadata_from_spend_logs(
+        mock_prisma, {"cli-session-raw-1798", "key-hash-short"}, window, cache=InMemoryCache()
+    )
+
+    assert result == {}
+    query_raw.assert_not_called()
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_accepts_hashed_jwt_digests():
+    jwt_digest = f"hashed-jwt-{hash_token('jwt-subject-1')}"
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(jwt_digest, None, "team-jwt", "jwt-user")]))
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {jwt_digest}, window, cache=InMemoryCache())
+
+    assert result[jwt_digest]["team_id"] == "team-jwt"
+    assert result[jwt_digest]["user_id"] == "jwt-user"
+    ((_, digests, _, _),) = [call.args for call in query_raw.call_args_list]
+    assert digests == [jwt_digest]
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_serves_repeat_lookups_from_the_cache():
+    found = hash_token("cli-session-found")
+    unknown = hash_token("cli-session-unknown")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    cache = InMemoryCache()
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(found, "found-alias", None, "owner-1")]))
+
+    first = await recover_key_metadata_from_spend_logs(mock_prisma, {found, unknown}, window, cache=cache)
+    second = await recover_key_metadata_from_spend_logs(mock_prisma, {found, unknown}, window, cache=cache)
+
+    assert first == second
+    assert set(first) == {found}
+    assert first[found]["key_alias"] == "found-alias"
+    assert query_raw.await_count == 1
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_only_queries_digests_the_cache_has_not_seen():
+    cached_digest = hash_token("cli-session-cached")
+    new_digest = hash_token("cli-session-new")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    cache = InMemoryCache()
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(cached_digest, "cached-alias", None, None)]))
+    await recover_key_metadata_from_spend_logs(mock_prisma, {cached_digest}, window, cache=cache)
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(new_digest, "new-alias", None, None)]))
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {cached_digest, new_digest}, window, cache=cache)
+
+    assert result[cached_digest]["key_alias"] == "cached-alias"
+    assert result[new_digest]["key_alias"] == "new-alias"
+    ((_, digests, _, _),) = [call.args for call in query_raw.call_args_list]
+    assert digests == [new_digest]
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_rescans_when_the_window_changes():
+    digest = hash_token("cli-session-windowed")
+    cache = InMemoryCache()
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([]))
+    await recover_key_metadata_from_spend_logs(
+        mock_prisma, {digest}, (datetime(2026, 9, 1), datetime(2026, 9, 4)), cache=cache
+    )
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(digest, "later-alias", None, None)]))
+
+    result = await recover_key_metadata_from_spend_logs(
+        mock_prisma, {digest}, (datetime(2026, 9, 7), datetime(2026, 9, 10)), cache=cache
+    )
+
+    assert result[digest]["key_alias"] == "later-alias"
+    assert query_raw.await_count == 1
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_retries_a_failed_query_only_after_the_miss_ttl():
+    digest = hash_token("cli-session-retry")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    cache = InMemoryCache(default_ttl=SPEND_LOG_KEY_METADATA_CACHE_TTL)
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, AsyncMock(side_effect=PrismaError("statement timeout")))
+    started = time.time()
+    assert await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=cache) == {}
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(digest, "back-online", None, None)]))
+
+    assert await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=cache) == {}
+    query_raw.assert_not_awaited()
+    miss_key = next(key for key in cache.ttl_dict if digest in key and not key.endswith(":missed-before"))
+    assert cache.ttl_dict[miss_key] - started <= SPEND_LOG_KEY_METADATA_MISS_CACHE_TTL + 1
+    cache.ttl_dict[miss_key] = time.time() - 1
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=cache)
+
+    assert result[digest]["key_alias"] == "back-online"
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_drops_the_owner_of_a_digest_shared_by_several_users():
+    shared_ui_digest = hash_token("ui-token")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(
+        mock_prisma,
+        _query_raw_spend_logs(
+            [{**_spend_log_row(shared_ui_digest, "ui-token", "litellm-dashboard", None), "first_owner": "alice", "last_owner": "bob"}]
+        ),
+    )
+
+    result = await recover_key_metadata_from_spend_logs(
+        mock_prisma, {shared_ui_digest}, window, cache=InMemoryCache()
+    )
+
+    assert result[shared_ui_digest] == {"key_alias": "ui-token", "team_id": "litellm-dashboard", "user_id": None}
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_keeps_the_owner_when_every_named_row_agrees():
+    digest = hash_token("cli-session-one-owner")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(
+        mock_prisma,
+        _query_raw_spend_logs(
+            [_spend_log_row(digest, None, None, "carol")]
+        ),
+    )
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=InMemoryCache())
+
+    assert result[digest]["user_id"] == "carol"
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_forgets_a_miss_long_before_a_hit():
+    found = hash_token("cli-session-found")
+    unknown = hash_token("cli-session-unknown")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    cache = InMemoryCache(default_ttl=SPEND_LOG_KEY_METADATA_CACHE_TTL)
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(found, "found-alias", None, None)]))
+    started = time.time()
+
+    await recover_key_metadata_from_spend_logs(mock_prisma, {found, unknown}, window, cache=cache)
+
+    hit_expires = next(deadline for key, deadline in cache.ttl_dict.items() if found in key)
+    miss_expires = next(deadline for key, deadline in cache.ttl_dict.items() if unknown in key)
+    assert miss_expires - started <= SPEND_LOG_KEY_METADATA_MISS_CACHE_TTL + 1
+    assert hit_expires - started >= SPEND_LOG_KEY_METADATA_CACHE_TTL - 1
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_runs_one_query_for_concurrent_lookups():
+    digest = hash_token("cli-session-shared")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    cache = InMemoryCache()
+    lock = asyncio.Lock()
+    mock_prisma = MagicMock()
+
+    async def slow_query_raw(sql: str, *params: object) -> list[dict[str, str | None]]:
+        await asyncio.sleep(0.01)
+        return [_spend_log_row(digest, "shared-alias", None, None)]
+
+    query_raw = _spend_log_transaction(mock_prisma, AsyncMock(side_effect=slow_query_raw))
+
+    results = await asyncio.gather(
+        *(
+            recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=cache, lock=lock)
+            for _ in range(9)
+        )
+    )
+
+    assert all(result[digest]["key_alias"] == "shared-alias" for result in results)
+    assert query_raw.await_count == 1
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_keeps_a_repeated_miss_as_long_as_a_hit():
+    unknown = hash_token("cli-session-never-named")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    cache = InMemoryCache(default_ttl=SPEND_LOG_KEY_METADATA_CACHE_TTL)
+    mock_prisma = MagicMock()
+    query_raw = _spend_log_transaction(mock_prisma, _query_raw_spend_logs([]))
+    await recover_key_metadata_from_spend_logs(mock_prisma, {unknown}, window, cache=cache)
+    first_miss_key = next(key for key in cache.ttl_dict if unknown in key and not key.endswith(":missed-before"))
+    cache.ttl_dict[first_miss_key] = time.time() - 1
+    started = time.time()
+
+    await recover_key_metadata_from_spend_logs(mock_prisma, {unknown}, window, cache=cache)
+
+    assert query_raw.await_count == 2
+    assert cache.ttl_dict[first_miss_key] - started >= SPEND_LOG_KEY_METADATA_CACHE_TTL - 1
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_keeps_the_owner_older_rows_agree_on_when_the_newest_is_nameless():
+    digest = hash_token("cli-session-owner-from-older-rows")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    _spend_log_transaction(mock_prisma, _query_raw_spend_logs([_spend_log_row(digest, None, "team-x", "alice")]))
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=InMemoryCache())
+
+    assert result[digest] == {"key_alias": None, "team_id": "team-x", "user_id": "alice"}
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_names_nothing_for_a_field_whose_rows_disagree():
+    digest = hash_token("cli-session-disagreeing-rows")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    _spend_log_transaction(
+        mock_prisma,
+        _query_raw_spend_logs(
+            [
+                {
+                    **_spend_log_row(digest, None, None, "carol"),
+                    "first_alias": "old-alias",
+                    "last_alias": "renamed-alias",
+                    "first_team": "team-a",
+                    "last_team": "team-b",
+                }
+            ]
+        ),
+    )
+
+    result = await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=InMemoryCache())
+
+    assert result[digest] == {"key_alias": None, "team_id": None, "user_id": "carol"}
+
+
+@pytest.mark.asyncio
+async def test_recover_key_metadata_from_spend_logs_bounds_the_scan_with_a_statement_timeout():
+    digest = hash_token("cli-session-bounded-scan")
+    window = (datetime(2026, 9, 7), datetime(2026, 9, 10))
+    mock_prisma = MagicMock()
+    calls: list[str] = []
+    transaction = MagicMock()
+    transaction.execute_raw = AsyncMock(side_effect=lambda sql: calls.append(sql) or 0)
+    transaction.query_raw = AsyncMock(side_effect=lambda sql, *args: calls.append("scan") or [])
+    mock_prisma.db.tx.return_value.__aenter__.return_value = transaction
+
+    await recover_key_metadata_from_spend_logs(mock_prisma, {digest}, window, cache=InMemoryCache())
+
+    assert calls == [f"SET LOCAL statement_timeout = {SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS}", "scan"]
+    assert mock_prisma.db.tx.call_args.kwargs["timeout"] == timedelta(
+        milliseconds=2 * SPEND_LOG_KEY_METADATA_QUERY_TIMEOUT_MS
+    )
diff --git a/tests/test_litellm/proxy/spend_tracking/test_spend_event.py b/tests/test_litellm/proxy/spend_tracking/test_spend_event.py
new file mode 100644
index 00000000000..ff449235582
--- /dev/null
+++ b/tests/test_litellm/proxy/spend_tracking/test_spend_event.py
@@ -0,0 +1,213 @@
+import json
+from datetime import datetime
+from typing import Final
+
+import pytest
+
+import litellm
+from litellm.caching.caching import Cache
+from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy.spend_tracking.spend_event import (
+    CACHE_OFF_KEY,
+    SpendEventBuildError,
+    SpendEventDecodeError,
+    build_spend_event,
+    decode_spend_event,
+    is_offloadable_success,
+    spend_event_callback_args,
+)
+from litellm.types.utils import LiteLLMBatch, ModelResponse, Usage
+
+_BIG_PROMPT: Final = "x" * 20_000
+_RESERVATION: Final = {
+    "reserved_cost": 0.5,
+    "entries": [{"counter_key": "key:hash", "reserved_cost": 0.5}],
+    "finalized": False,
+    "input_cost": 0.1,
+    "input_tokens": 5000,
+}
+
+
+def _response(tool_name: str | None = None) -> ModelResponse:
+    tool_calls: Final = (
+        [{"id": "call-1", "type": "function", "function": {"name": tool_name, "arguments": "{}"}}]
+        if tool_name is not None
+        else None
+    )
+    return ModelResponse(
+        id="chatcmpl-1",
+        model="gpt-4o-2024-08-06",
+        choices=[
+            {
+                "index": 0,
+                "message": {"role": "assistant", "content": "y" * 20_000, "tool_calls": tool_calls},
+                "finish_reason": "tool_calls" if tool_name else "stop",
+            }
+        ],
+        usage=Usage(prompt_tokens=5000, completion_tokens=4000, total_tokens=9000),
+    )
+
+
+def _success_kwargs(preset_cache_key: str | None = "preset-key") -> dict:
+    return {
+        "litellm_call_id": "call-1",
+        "call_type": "acompletion",
+        "model": "gpt-4o",
+        "custom_llm_provider": "openai",
+        "stream": False,
+        "cache_hit": None,
+        "response_cost": 0.0125,
+        "completion_start_time": datetime(2026, 1, 1, 0, 0, 1),
+        "messages": [{"role": "user", "content": _BIG_PROMPT}],
+        "tools": [{"type": "function", "function": {"name": "get_weather", "parameters": {"type": "object"}}}],
+        "litellm_params": {
+            "api_base": "https://api.openai.com",
+            "preset_cache_key": preset_cache_key,
+            "proxy_server_request": {"body": {"messages": [{"role": "user", "content": _BIG_PROMPT}]}},
+            "metadata": {
+                "user_api_key": "hash-1",
+                "user_api_key_user_id": "user-1",
+                "user_api_key_team_id": "team-1",
+                "user_api_key_org_id": "org-1",
+                "user_api_key_end_user_id": "end-user-1",
+                "user_api_key_auth": UserAPIKeyAuth(api_key="hash-1", budget_reservation=dict(_RESERVATION)),
+                "model_group": "gpt-4o",
+                "model_info": {"id": "deployment-1"},
+                "tags": ["tag-a"],
+                "litellm_parent_otel_span": object(),
+            },
+        },
+        "standard_logging_object": {
+            "response_cost": 0.0125,
+            "model": "gpt-4o-2024-08-06",
+            "model_id": "deployment-1",
+            "request_tags": ["tag-a"],
+            "request_model_access_groups": ["premium"],
+            "messages": [{"role": "user", "content": _BIG_PROMPT}],
+            "response": {"choices": [{"message": {"content": "y" * 20_000}}]},
+            "model_parameters": {"temperature": 0.1},
+            "metadata": {"user_api_key_hash": "hash-1", "usage_object": {"prompt_tokens": 5000}},
+            "hidden_params": {"litellm_overhead_time_ms": 3},
+            "model_map_information": {},
+        },
+    }
+
+
+def _build(kwargs: dict, response: object, store_bodies: bool = False) -> bytes:
+    line: Final = build_spend_event(
+        kwargs, response, datetime(2026, 1, 1), datetime(2026, 1, 1, 0, 0, 2), store_bodies=store_bodies
+    )
+    assert isinstance(line, bytes)
+    return line
+
+
+def test_event_is_compact_and_omits_bodies_by_default():
+    line: Final = _build(_success_kwargs(), _response(tool_name="get_weather"))
+    assert line.endswith(b"\n")
+    assert len(line) < 4_000
+    assert _BIG_PROMPT.encode() not in line
+    assert b"yyyy" not in line
+    decoded: Final = json.loads(line)
+    assert "messages" not in decoded["standard_logging_object"]
+    assert "response" not in decoded["standard_logging_object"]
+    assert decoded["litellm_params"]["proxy_server_request"] is None
+
+
+def test_event_carries_bodies_when_spend_logs_store_them():
+    line: Final = _build(_success_kwargs(), _response(), store_bodies=True)
+    decoded: Final = json.loads(line)
+    assert decoded["standard_logging_object"]["messages"][0]["content"] == _BIG_PROMPT
+    assert decoded["standard_logging_object"]["response"]["choices"][0]["message"]["content"] == "y" * 20_000
+    assert decoded["litellm_params"]["proxy_server_request"]["body"]["messages"][0]["content"] == _BIG_PROMPT
+
+
+def test_round_trip_preserves_identity_usage_reservation_and_tools():
+    line: Final = _build(_success_kwargs(), _response(tool_name="get_weather"))
+    event: Final = decode_spend_event(line)
+    assert not isinstance(event, SpendEventDecodeError)
+    args: Final = spend_event_callback_args(event)
+
+    metadata: Final = args.kwargs["litellm_params"]["metadata"]
+    assert metadata is not None
+    assert (metadata["user_api_key"], metadata["user_api_key_team_id"], metadata["user_api_key_org_id"]) == (
+        "hash-1",
+        "team-1",
+        "org-1",
+    )
+    assert metadata["user_api_key_budget_reservation"] == _RESERVATION
+    assert "user_api_key_auth" not in metadata
+    assert "litellm_parent_otel_span" not in metadata
+    assert args.kwargs["standard_logging_object"]["request_model_access_groups"] == ["premium"]
+    assert args.kwargs["standard_logging_object"]["response_cost"] == 0.0125
+    assert args.kwargs["tools"] == ({"type": "function", "function": {"name": "get_weather"}},)
+    assert args.kwargs["completion_start_time"] == datetime(2026, 1, 1, 0, 0, 1)
+    assert (args.start_time, args.end_time) == (datetime(2026, 1, 1), datetime(2026, 1, 1, 0, 0, 2))
+    assert args.response_obj is not None
+    assert args.response_obj["id"] == "chatcmpl-1"
+    assert args.response_obj["usage"]["prompt_tokens"] == 5000
+    assert args.response_obj["usage"]["completion_tokens"] == 4000
+    tool_calls: Final = args.response_obj["choices"][0]["message"]["tool_calls"]
+    assert [call["function"]["name"] for call in tool_calls] == ["get_weather"]
+    assert "complete_streaming_response" not in args.kwargs
+
+
+def test_streaming_event_reconstructs_complete_streaming_response():
+    kwargs: Final = {**_success_kwargs(), "stream": True, "complete_streaming_response": _response()}
+    event: Final = decode_spend_event(_build(kwargs, _response()))
+    assert not isinstance(event, SpendEventDecodeError)
+    args: Final = spend_event_callback_args(event)
+    assert args.kwargs["stream"] is True
+    assert args.kwargs["complete_streaming_response"] == args.response_obj
+
+
+class _HashingCache(Cache):
+    def __init__(self) -> None:
+        pass
+
+    def get_cache_key(self, **kwargs) -> str:
+        raise AssertionError("the fast path must not hash the request body")
+
+
+@pytest.mark.parametrize(
+    ("cache", "preset", "expected"),
+    [
+        (None, "preset-key", CACHE_OFF_KEY),
+        (_HashingCache(), "preset-key", "preset-key"),
+        (_HashingCache(), None, None),
+    ],
+)
+def test_event_reuses_preset_cache_key_and_never_hashes(monkeypatch, cache, preset, expected):
+    monkeypatch.setattr(litellm, "cache", cache)
+    decoded: Final = json.loads(_build(_success_kwargs(preset_cache_key=preset), _response()))
+    assert decoded["litellm_params"]["preset_cache_key"] == expected
+
+
+def test_unbuildable_kwargs_fall_back_to_in_process_tracking():
+    kwargs: Final = {**_success_kwargs(), "response_cost": "not-a-number"}
+    assert isinstance(
+        build_spend_event(kwargs, _response(), datetime.now(), datetime.now(), False), SpendEventBuildError
+    )
+
+
+def test_undecodable_line_is_an_error_value():
+    assert isinstance(decode_spend_event(b'{"version": 2}\n'), SpendEventDecodeError)
+    assert isinstance(decode_spend_event(b"not json\n"), SpendEventDecodeError)
+
+
+def test_batch_retrieves_stay_in_process():
+    assert is_offloadable_success(_response()) is True
+    assert is_offloadable_success(None) is True
+    assert (
+        is_offloadable_success(
+            LiteLLMBatch(
+                id="batch-1",
+                completion_window="24h",
+                created_at=1,
+                endpoint="/v1/chat/completions",
+                input_file_id="f",
+                object="batch",
+                status="completed",
+            )
+        )
+        is False
+    )
diff --git a/tests/test_litellm/proxy/spend_tracking/test_spend_event_producer.py b/tests/test_litellm/proxy/spend_tracking/test_spend_event_producer.py
new file mode 100644
index 00000000000..adfb1251d1c
--- /dev/null
+++ b/tests/test_litellm/proxy/spend_tracking/test_spend_event_producer.py
@@ -0,0 +1,359 @@
+import asyncio
+from collections.abc import Awaitable, Callable
+from pathlib import Path
+from typing import Final
+
+import pytest
+import uvloop
+
+from litellm.proxy.spend_tracking.spend_event_producer import (
+    AddressError,
+    CollectorAddress,
+    CollectorSettings,
+    SpendEventProducer,
+    TcpAddress,
+    UnixAddress,
+    build_spend_event_producer,
+    open_collector_connection,
+    parse_collector_address,
+)
+
+
+class _Sidecar:
+    """A unix-socket server that records every line it receives, standing in for the collector."""
+
+    def __init__(self, path: Path, reads: bool = True, limit: int = 2**16) -> None:
+        self.path = path
+        self.reads = reads
+        self.limit = limit
+        self.lines: list[bytes] = []  # mutable-ok: test double records what the producer sent
+        self._server: asyncio.Server | None = None
+        self._stopped = asyncio.Event()
+        self._connections: list[asyncio.StreamWriter] = []  # mutable-ok: test double tracks peers to hang up on
+
+    async def __aenter__(self) -> "_Sidecar":
+        self._server = await asyncio.start_unix_server(self._on_connection, path=str(self.path), limit=self.limit)
+        return self
+
+    async def __aexit__(self, *exc: object) -> None:
+        self._stopped.set()
+        await self.hang_up()
+
+    async def hang_up(self) -> None:
+        """Exit the way a stopped sidecar does: stop listening and close every producer connection."""
+        assert self._server is not None
+        self._server.close()
+        for connection in self._connections:
+            connection.close()
+            await connection.wait_closed()
+        await self._server.wait_closed()
+
+    async def _on_connection(self, reader: asyncio.StreamReader, writer: asyncio.StreamWriter) -> None:
+        self._connections.append(writer)
+        if not self.reads:
+            await self._stopped.wait()
+            return
+        while line := await reader.readline():
+            self.lines.append(line)
+        writer.close()
+
+
+class _CrashingSidecar(_Sidecar):
+    """Bills a few lines, then dies mid-stream with the producer's backlog still queued behind them."""
+
+    def __init__(self, path: Path, lines_before_crash: int) -> None:
+        super().__init__(path, limit=2**20)
+        self._lines_before_crash = lines_before_crash
+
+    async def _on_connection(self, reader: asyncio.StreamReader, writer: asyncio.StreamWriter) -> None:
+        self._connections.append(writer)
+        for _ in range(self._lines_before_crash):
+            self.lines.append(await reader.readline())
+        writer.transport.abort()
+
+
+class _Fallback:
+    def __init__(self) -> None:
+        self.lines: list[bytes] = []  # mutable-ok: test double records what fell back to in-process
+
+    async def __call__(self, line: bytes) -> None:
+        self.lines.append(line)
+
+
+class _GatedFallback(_Fallback):
+    """A fallback that blocks, like a slow database write, until the test releases it."""
+
+    def __init__(self) -> None:
+        super().__init__()
+        self.started = asyncio.Event()
+        self.release = asyncio.Event()
+
+    async def __call__(self, line: bytes) -> None:
+        self.started.set()
+        await self.release.wait()
+        await super().__call__(line)
+
+
+class _StalledDrainWriter(asyncio.StreamWriter):
+    """Hands bytes to the real transport but never wakes ``drain()``: the loop iteration between a flush
+    completing and the writer task resuming, frozen in place."""
+
+    def __init__(self, real: asyncio.StreamWriter, reader: asyncio.StreamReader) -> None:
+        super().__init__(real.transport, real.transport.get_protocol(), reader, asyncio.get_running_loop())
+        self._real_writer_whose_finalizer_would_close_the_transport = real
+
+    async def drain(self) -> None:
+        await asyncio.Event().wait()
+
+
+async def _open_with_stalled_drain(
+    address: CollectorAddress, timeout: float
+) -> tuple[asyncio.StreamReader, asyncio.StreamWriter]:
+    reader, writer = await open_collector_connection(address, timeout)
+    return reader, _StalledDrainWriter(writer, reader)
+
+
+def _producer(
+    path: Path,
+    fallback: _Fallback,
+    on_unavailable="fallback",
+    buffer_size: int = 100,
+    open_connection: Callable[
+        [CollectorAddress, float], Awaitable[tuple[asyncio.StreamReader, asyncio.StreamWriter]]
+    ] = open_collector_connection,
+) -> SpendEventProducer:
+    return SpendEventProducer(
+        address=UnixAddress(path=str(path)),
+        on_unavailable=on_unavailable,
+        buffer_size=buffer_size,
+        connect_timeout=1.0,
+        fallback=fallback,
+        open_connection=open_connection,
+    )
+
+
+def test_parse_collector_address():
+    assert parse_collector_address("unix:///var/run/litellm/collector.sock") == UnixAddress(
+        path="/var/run/litellm/collector.sock"
+    )
+    assert parse_collector_address("tcp://127.0.0.1:4100") == TcpAddress(host="127.0.0.1", port=4100)
+    assert parse_collector_address("tcp://localhost:4100") == TcpAddress(host="localhost", port=4100)
+    assert parse_collector_address("tcp://[::1]:4100") == TcpAddress(host="::1", port=4100)
+    assert isinstance(parse_collector_address("redis://localhost:6379"), AddressError)
+    assert isinstance(parse_collector_address("tcp://127.0.0.1"), AddressError)
+
+
+@pytest.mark.parametrize("address", ["tcp://0.0.0.0:4100", "tcp://10.0.0.5:4100", "tcp://collector.svc:4100"])
+def test_tcp_address_outside_loopback_is_refused(address: str):
+    """The socket has no authentication, so anything reachable from outside the pod would accept forged spend."""
+    error: Final = parse_collector_address(address)
+    assert isinstance(error, AddressError)
+    assert "loopback" in error.reason
+    assert build_spend_event_producer(CollectorSettings(enabled=True, address=address), _Fallback()) is None
+
+
+def test_gateway_produces_only_when_enabled_and_not_the_sidecar_itself():
+    fallback: Final = _Fallback()
+    assert build_spend_event_producer(CollectorSettings(enabled=False), fallback) is None
+    assert build_spend_event_producer(CollectorSettings(enabled=True, job_role="collector"), fallback) is None
+    assert build_spend_event_producer(CollectorSettings(enabled=True, address="redis://x"), fallback) is None
+    assert isinstance(build_spend_event_producer(CollectorSettings(enabled=True), fallback), SpendEventProducer)
+
+
+def test_settings_read_the_documented_env(monkeypatch):
+    monkeypatch.setenv("LITELLM_COLLECTOR_ENABLED", "true")
+    monkeypatch.setenv("LITELLM_COLLECTOR_ADDRESS", "tcp://127.0.0.1:4100")
+    monkeypatch.setenv("LITELLM_COLLECTOR_BUFFER_SIZE", "50")
+    monkeypatch.setenv("LITELLM_COLLECTOR_ON_UNAVAILABLE", "drop")
+    monkeypatch.setenv("LITELLM_JOB_ROLE", "collector")
+    settings: Final = CollectorSettings()
+    assert (settings.enabled, settings.address, settings.buffer_size, settings.on_unavailable) == (
+        True,
+        "tcp://127.0.0.1:4100",
+        50,
+        "drop",
+    )
+    assert settings.produces is False
+
+
+@pytest.mark.asyncio
+async def test_events_reach_the_sidecar_once_and_in_order(tmp_path: Path):
+    fallback: Final = _Fallback()
+    async with _Sidecar(tmp_path / "spend.sock") as sidecar:
+        producer: Final = _producer(sidecar.path, fallback)
+        outcomes: Final = [await producer.publish(f"event-{i}\n".encode()) for i in range(20)]
+        await producer.close(drain_timeout=5.0)
+        await asyncio.sleep(0.05)
+
+    assert outcomes == ["queued"] * 20
+    assert sidecar.lines == [f"event-{i}\n".encode() for i in range(20)]
+    assert fallback.lines == []
+    stats: Final = producer.stats()
+    assert (stats.queued, stats.sent, stats.fallback, stats.dropped) == (20, 20, 0, 0)
+
+
+@pytest.mark.asyncio
+async def test_unreachable_sidecar_falls_back_in_process_and_backs_off(tmp_path: Path):
+    fallback: Final = _Fallback()
+    producer: Final = _producer(tmp_path / "missing.sock", fallback)
+    first: Final = await producer.publish(b"event-1\n")
+    await asyncio.sleep(0.05)
+    second: Final = await producer.publish(b"event-2\n")
+    await producer.close(drain_timeout=5.0)
+
+    assert first == "queued"
+    assert second == "fallback"
+    assert fallback.lines == [b"event-1\n", b"event-2\n"]
+    stats: Final = producer.stats()
+    assert (stats.sent, stats.fallback, stats.dropped, stats.connected) == (0, 2, 0, False)
+
+
+@pytest.mark.parametrize("loop_factory", [asyncio.new_event_loop, uvloop.new_event_loop], ids=["asyncio", "uvloop"])
+def test_sidecar_hang_up_falls_back_instead_of_losing_events(
+    tmp_path: Path, loop_factory: Callable[[], asyncio.AbstractEventLoop]
+):
+    async def scenario() -> tuple[list[bytes], list[bytes], tuple[int, int, int]]:
+        fallback: Final = _Fallback()
+        sidecar: Final = _Sidecar(tmp_path / "spend.sock")
+        async with sidecar:
+            producer: Final = _producer(sidecar.path, fallback)
+            await producer.publish(b"event-1\n")
+            await asyncio.sleep(0.05)
+            await sidecar.hang_up()
+            await asyncio.sleep(0.05)
+            await producer.publish(b"event-2\n")
+            await producer.close(drain_timeout=5.0)
+        stats: Final = producer.stats()
+        return sidecar.lines, fallback.lines, (stats.sent, stats.fallback, stats.dropped)
+
+    with asyncio.Runner(loop_factory=loop_factory) as runner:
+        sidecar_lines, fallback_lines, counts = runner.run(scenario())
+
+    assert sidecar_lines == [b"event-1\n"]
+    assert fallback_lines == [b"event-2\n"]
+    assert counts == (1, 1, 0)
+
+
+@pytest.mark.parametrize("loop_factory", [asyncio.new_event_loop, uvloop.new_event_loop], ids=["asyncio", "uvloop"])
+def test_mid_stream_crash_never_bills_an_event_on_both_sides(
+    tmp_path: Path, loop_factory: Callable[[], asyncio.AbstractEventLoop]
+):
+    """Events large enough to straddle the kernel buffer, a sidecar that reads some and then drops the socket: a
+    failed write may only fall back when the sidecar cannot have read the whole line."""
+    events: Final = tuple(f"event-{i:03d}-".encode() + b"x" * 65536 + b"\n" for i in range(64))
+
+    async def scenario() -> tuple[list[bytes], list[bytes], tuple[int, int, int]]:
+        fallback: Final = _Fallback()
+        sidecar: Final = _CrashingSidecar(tmp_path / "spend.sock", lines_before_crash=3)
+        async with sidecar:
+            producer: Final = _producer(sidecar.path, fallback)
+            for event in events:
+                assert await producer.publish(event) == "queued"
+            await asyncio.sleep(0.2)
+            await producer.close(drain_timeout=5.0)
+        stats: Final = producer.stats()
+        return sidecar.lines, fallback.lines, (stats.sent, stats.fallback, stats.dropped)
+
+    with asyncio.Runner(loop_factory=loop_factory) as runner:
+        sidecar_lines, fallback_lines, counts = runner.run(scenario())
+
+    assert sidecar_lines == list(events[:3])
+    assert set(sidecar_lines).isdisjoint(fallback_lines)
+    assert len(fallback_lines) == len(set(fallback_lines))
+    assert fallback_lines[-1] == events[-1]
+    assert counts[0] + counts[1] == len(events) and counts[2] == 0
+    assert counts[0] >= len(sidecar_lines)
+
+
+@pytest.mark.asyncio
+async def test_drain_timeout_hands_the_in_flight_event_to_fallback(tmp_path: Path):
+    """A sidecar that stops reading leaves one event half-written; cancelling the writer must not lose it."""
+    fallback: Final = _Fallback()
+    stuck: Final = b"x" * (4 * 1024 * 1024) + b"\n"
+    async with _Sidecar(tmp_path / "spend.sock", reads=False) as sidecar:
+        producer: Final = _producer(sidecar.path, fallback)
+        assert await producer.publish(stuck) == "queued"
+        await asyncio.sleep(0.1)
+        await producer.close(drain_timeout=0.2)
+
+    assert fallback.lines == [stuck]
+    stats: Final = producer.stats()
+    assert (stats.sent, stats.fallback, stats.connected) == (0, 1, False)
+
+
+@pytest.mark.asyncio
+async def test_shutdown_lets_the_writer_finish_a_fallback_already_in_progress(tmp_path: Path):
+    """Cancelling the writer while it runs the pipeline in-process must neither lose nor repeat that event."""
+    fallback: Final = _GatedFallback()
+    producer: Final = _producer(tmp_path / "missing.sock", fallback)
+    assert await producer.publish(b"event-1\n") == "queued"
+    await asyncio.wait_for(fallback.started.wait(), 5.0)
+    closing: Final = asyncio.ensure_future(producer.close(drain_timeout=0.05))
+    await asyncio.sleep(0.2)
+    assert fallback.lines == []
+    fallback.release.set()
+    await asyncio.wait_for(closing, 5.0)
+
+    assert fallback.lines == [b"event-1\n"]
+    assert producer.stats().fallback == 1
+
+
+@pytest.mark.asyncio
+async def test_shutdown_does_not_replay_an_event_the_kernel_already_took(tmp_path: Path):
+    """Cancelling a drain whose bytes already left the process must not run the event a second time in-process."""
+    fallback: Final = _Fallback()
+    async with _Sidecar(tmp_path / "spend.sock") as sidecar:
+        producer: Final = _producer(sidecar.path, fallback, open_connection=_open_with_stalled_drain)
+        assert await producer.publish(b"event-1\n") == "queued"
+        await asyncio.sleep(0.1)
+        await producer.close(drain_timeout=0.2)
+        await asyncio.sleep(0.05)
+
+    assert sidecar.lines == [b"event-1\n"]
+    assert fallback.lines == []
+    stats: Final = producer.stats()
+    assert (stats.fallback, stats.dropped, stats.connected) == (0, 0, False)
+
+
+@pytest.mark.asyncio
+async def test_drop_policy_counts_instead_of_running_in_process(tmp_path: Path):
+    fallback: Final = _Fallback()
+    producer: Final = _producer(tmp_path / "missing.sock", fallback, on_unavailable="drop")
+    await producer.publish(b"event-1\n")
+    await producer.close(drain_timeout=5.0)
+    assert await producer.publish(b"event-2\n") == "dropped"
+
+    assert fallback.lines == []
+    assert producer.stats().dropped == 2
+
+
+@pytest.mark.asyncio
+async def test_full_buffer_applies_the_unavailable_policy_immediately(tmp_path: Path):
+    fallback: Final = _Fallback()
+    async with _Sidecar(tmp_path / "spend.sock") as sidecar:
+        producer: Final = _producer(sidecar.path, fallback, buffer_size=2)
+        outcomes: Final = [await producer.publish(f"event-{i}\n".encode()) for i in range(3)]
+        await producer.close(drain_timeout=5.0)
+        await asyncio.sleep(0.05)
+
+    assert outcomes == ["queued", "queued", "fallback"]
+    assert fallback.lines == [b"event-2\n"]
+    assert sidecar.lines == [b"event-0\n", b"event-1\n"]
+
+
+@pytest.mark.asyncio
+async def test_close_flushes_buffered_events_then_refuses_new_ones(tmp_path: Path):
+    fallback: Final = _Fallback()
+    async with _Sidecar(tmp_path / "spend.sock") as sidecar:
+        producer: Final = _producer(sidecar.path, fallback)
+        for i in range(50):
+            await producer.publish(f"event-{i}\n".encode())
+        assert sidecar.lines == []
+        await producer.close(drain_timeout=5.0)
+        await asyncio.sleep(0.05)
+        after_close: Final = await producer.publish(b"late\n")
+
+    assert len(sidecar.lines) == 50
+    assert after_close == "fallback"
+    assert fallback.lines == [b"late\n"]
+    assert producer.stats().connected is False
diff --git a/tests/test_litellm/proxy/spend_tracking/test_spend_management_endpoints.py b/tests/test_litellm/proxy/spend_tracking/test_spend_management_endpoints.py
index 329a33eb440..671a8ae63fc 100644
--- a/tests/test_litellm/proxy/spend_tracking/test_spend_management_endpoints.py
+++ b/tests/test_litellm/proxy/spend_tracking/test_spend_management_endpoints.py
@@ -455,6 +455,34 @@ async def test_assert_user_can_view_request_id_rejects_both_users_none():
     assert exc_info.value.status_code == 403
 
 
+@pytest.mark.asyncio
+async def test_assert_user_can_view_request_id_rejects_missing_row():
+    """
+    A request_id with no spend-log row (e.g. pruned by retention) must not
+    authorize reading the payload from cold storage; a missing row is not
+    the same as an owned row.
+    """
+
+    class MockSpendLogs:
+        async def find_unique(self, where, include=None):
+            return None
+
+    class MockDB:
+        def __init__(self):
+            self.litellm_spendlogs = MockSpendLogs()
+
+    class MockPrisma:
+        def __init__(self):
+            self.db = MockDB()
+
+    auth = UserAPIKeyAuth(user_role=LitellmUserRoles.INTERNAL_USER, user_id="user_1")
+    with pytest.raises(HTTPException) as exc_info:
+        await spend_management_endpoints._assert_user_can_view_request_id(
+            MockPrisma(), auth, "req-missing-row"
+        )
+    assert exc_info.value.status_code == 403
+
+
 def test_ui_view_request_response_forbids_non_admin_without_db(client, monkeypatch):
     """
     Without prisma, non-admins cannot be authorized to read request/response
@@ -5703,6 +5731,29 @@ def _cold_storage_handler(payload):
     return ColdStorageHandler(cold_storage_logger=logger), logger
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize("cold_has_audit", [False, True])
+async def test_resolve_payload_recovers_truncated_classifier_audit_without_losing_existing_fields(cold_has_audit):
+    full_audit = {"classifier_input": {"system": "full rubric"}, "originating_request_masked": {"input": "source"}}
+    truncated_request = {"model": "classifier", "classifier_input": {"system": "litellm_truncated"}}
+    handler, logger = _cold_storage_handler({
+        "proxy_server_request": {"body": {}}, **(full_audit if cold_has_audit else {}),
+    })
+    row = {
+        "messages": '[{"role":"user","content":"ask"}]', "response": '{"tier":"SIMPLE"}',
+        "proxy_server_request": json.dumps(truncated_request), "metadata": {"cold_storage_object_key": "k/audit.json"},
+    }
+    resolved = await spend_management_endpoints._resolve_request_response_payload(row, cold_storage_handler=handler)
+    assert logger.requested_object_keys == ["k/audit.json"]
+    assert resolved.messages == row["messages"]
+    assert resolved.response == row["response"]
+    if cold_has_audit:
+        assert resolved.proxy_server_request["classifier_input"] == full_audit["classifier_input"]
+        assert resolved.proxy_server_request["originating_request_masked"] == full_audit["originating_request_masked"]
+    else:
+        assert resolved.proxy_server_request == row["proxy_server_request"]
+
+
 @pytest.mark.parametrize(
     "value, expected",
     [
@@ -6777,3 +6828,161 @@ async def test_ui_view_spend_logs_search_returns_flat_rows_when_grouping_by_sess
         assert "next_session_cursor" not in data
     finally:
         app.dependency_overrides.pop(ps.user_api_key_auth, None)
+
+
+def _fake_prisma_with_owned_spend_log(owner_user_id, messages_json, response_json):
+    class _Row:
+        user = owner_user_id
+        team_id = None
+
+    class _SpendLogs:
+        async def find_unique(self, where, include=None):
+            return _Row()
+
+    class _DB:
+        def __init__(self):
+            self.litellm_spendlogs = _SpendLogs()
+
+        async def query_raw(self, _sql, *_args):
+            return [
+                {
+                    "messages": messages_json,
+                    "response": response_json,
+                    "proxy_server_request": "{}",
+                    "metadata": "{}",
+                }
+            ]
+
+    class _Prisma:
+        def __init__(self):
+            self.db = _DB()
+
+    return _Prisma()
+
+
+def test_ui_view_request_response_internal_user_owner_gets_payload(client, monkeypatch):
+    """
+    An internal_user who owns the spend-log row can fetch the Logs drawer
+    detail payload for their own request (regression for #34099, where the
+    route was blocked for INTERNAL_USER before reaching this ownership check).
+    """
+    messages_json = json.dumps([{"role": "user", "content": "hi"}])
+    response_json = json.dumps({"choices": [{"message": {"content": "hello"}}]})
+    monkeypatch.setattr(
+        "litellm.proxy.proxy_server.prisma_client",
+        _fake_prisma_with_owned_spend_log("user_a", messages_json, response_json),
+    )
+    app.dependency_overrides[ps.user_api_key_auth] = lambda: UserAPIKeyAuth(
+        user_role=LitellmUserRoles.INTERNAL_USER, user_id="user_a"
+    )
+    try:
+        response = client.get(
+            "/spend/logs/ui/req-owned-by-user-a",
+            headers={"Authorization": "Bearer sk-test"},
+        )
+        assert response.status_code == 200
+        body = response.json()
+        assert json.loads(body["messages"]) == [{"role": "user", "content": "hi"}]
+        assert json.loads(body["response"]) == {
+            "choices": [{"message": {"content": "hello"}}]
+        }
+    finally:
+        app.dependency_overrides.pop(ps.user_api_key_auth, None)
+
+
+class _RecordingAdditionalLoggingUtils:
+    """Injectable custom logger that records every request_id it's asked for."""
+
+    def __init__(self, payload):
+        self._payload = payload
+        self.requested_ids = []
+
+    async def get_request_response_payload(self, request_id, start_time_utc, end_time_utc):
+        self.requested_ids.append(request_id)
+        return self._payload
+
+
+def test_ui_view_request_response_internal_user_non_owner_forbidden(client, monkeypatch):
+    """
+    A different internal_user requesting someone else's row is forbidden;
+    guards against _assert_user_can_view_request_id being skipped in the
+    detail-drawer handler. Also proves the handler stops before it ever asks
+    a custom logger or the DB for the payload.
+    """
+    messages_json = json.dumps([{"role": "user", "content": "hi"}])
+    response_json = json.dumps({"choices": [{"message": {"content": "hello"}}]})
+    fake_prisma = _fake_prisma_with_owned_spend_log("user_a", messages_json, response_json)
+    original_query_raw = fake_prisma.db.query_raw
+    query_raw_calls = []
+
+    async def _spy_query_raw(*args, **kwargs):
+        query_raw_calls.append((args, kwargs))
+        return await original_query_raw(*args, **kwargs)
+
+    fake_prisma.db.query_raw = _spy_query_raw
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", fake_prisma)
+
+    custom_logger = _RecordingAdditionalLoggingUtils({"messages": "should-not-be-returned"})
+    monkeypatch.setattr(
+        litellm.logging_callback_manager,
+        "get_active_additional_logging_utils_from_custom_logger",
+        lambda: [custom_logger],
+    )
+
+    app.dependency_overrides[ps.user_api_key_auth] = lambda: UserAPIKeyAuth(
+        user_role=LitellmUserRoles.INTERNAL_USER, user_id="user_b"
+    )
+    try:
+        response = client.get(
+            "/spend/logs/ui/req-owned-by-user-a",
+            headers={"Authorization": "Bearer sk-test"},
+        )
+        assert response.status_code == 403
+        assert custom_logger.requested_ids == []
+        assert query_raw_calls == []
+    finally:
+        app.dependency_overrides.pop(ps.user_api_key_auth, None)
+
+
+def test_ui_view_request_response_internal_user_missing_row_forbidden(client, monkeypatch):
+    """
+    Regression for the fail-open in _assert_user_can_view_request_id: a
+    request_id with no spend-log row (e.g. pruned by retention) must be
+    denied before the handler ever consults a custom logger, otherwise a
+    non-admin who guesses/obtains a request_id could read another tenant's
+    payload out of cold storage. Fails if `if row is None: return` is
+    reintroduced.
+    """
+
+    class _SpendLogs:
+        async def find_unique(self, where, include=None):
+            return None
+
+    class _DB:
+        def __init__(self):
+            self.litellm_spendlogs = _SpendLogs()
+
+    from types import SimpleNamespace
+
+    fake_prisma = SimpleNamespace(db=_DB())
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", fake_prisma)
+
+    custom_logger = _RecordingAdditionalLoggingUtils({"messages": "should-not-be-returned"})
+    monkeypatch.setattr(
+        litellm.logging_callback_manager,
+        "get_active_additional_logging_utils_from_custom_logger",
+        lambda: [custom_logger],
+    )
+
+    app.dependency_overrides[ps.user_api_key_auth] = lambda: UserAPIKeyAuth(
+        user_role=LitellmUserRoles.INTERNAL_USER, user_id="user_a"
+    )
+    try:
+        response = client.get(
+            "/spend/logs/ui/req-pruned",
+            headers={"Authorization": "Bearer sk-test"},
+        )
+        assert response.status_code == 403
+        assert custom_logger.requested_ids == []
+    finally:
+        app.dependency_overrides.pop(ps.user_api_key_auth, None)
diff --git a/tests/test_litellm/proxy/spend_tracking/test_spend_tracking_utils.py b/tests/test_litellm/proxy/spend_tracking/test_spend_tracking_utils.py
index 5a79560b972..df113197ec6 100644
--- a/tests/test_litellm/proxy/spend_tracking/test_spend_tracking_utils.py
+++ b/tests/test_litellm/proxy/spend_tracking/test_spend_tracking_utils.py
@@ -1,8 +1,8 @@
 import asyncio
 import datetime
 import json
-from datetime import timezone
 from collections.abc import Mapping
+from datetime import timezone
 from typing import Any, Final, cast
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -15,12 +15,15 @@ from litellm.constants import (
     LITELLM_TRUNCATION_DB_SAFEGUARD_NOTE,
     LITTELM_CLI_SERVICE_ACCOUNT_NAME,
     LITTELM_INTERNAL_HEALTH_SERVICE_ACCOUNT_NAME,
+    MAX_SPEND_LOG_MODEL_NAME_LENGTH,
     REDACTED_BY_LITELM_STRING,
     SESSION_ID_OMITTED_METADATA_KEY,
+    UNKNOWN_MODEL_SPEND_LOG_MODEL,
 )
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
-from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy._types import SpendLogsPayload, UserAPIKeyAuth
 from litellm.proxy.litellm_pre_call_utils import LiteLLMProxyRequestSetup
+from litellm.proxy.route_llm_request import ProxyModelNotFoundError
 from litellm.proxy.spend_tracking.spend_tracking_utils import (
     _get_messages_for_spend_logs_payload,
     _get_proxy_server_request_for_spend_logs_payload,
@@ -35,11 +38,10 @@ from litellm.proxy.spend_tracking.spend_tracking_utils import (
     _sanitize_error_information_for_spend_logs,
     _sanitize_guardrail_information_for_spend_logs,
     _sanitize_request_body_for_spend_logs_payload,
-    _should_store_prompts_and_responses_in_spend_logs,
     get_logging_payload,
     get_spend_logs_id,
+    should_store_prompts_and_responses_in_spend_logs,
 )
-from litellm.proxy._types import SpendLogsPayload
 from litellm.proxy.utils import hash_token
 from litellm.types.utils import (
     StandardLoggingHiddenParams,
@@ -67,6 +69,30 @@ def _get_additional_usage_values_for_usage(usage: litellm.Usage) -> dict:
     return metadata["additional_usage_values"]
 
 
+@pytest.mark.parametrize("store_prompts,redact", [(True, False), (False, False), (True, True)])
+def test_classifier_audit_spend_storage_obeys_privacy_and_truncation(monkeypatch, store_prompts, redact):
+    from litellm.proxy import proxy_server
+
+    monkeypatch.setattr(proxy_server, "general_settings", {"store_prompts_in_spend_logs": store_prompts})
+    audit: Final = {
+        "classifier_input": {"system": "rubric" * 1000, "messages": [{"role": "user", "content": "ask"}]},
+        "originating_request_masked": {"input": "source-only", "api_key": "REDACTED"},
+    }
+    stored: Final = json.loads(_get_proxy_server_request_for_spend_logs_payload(
+        metadata={}, litellm_params={"proxy_server_request": {"body": {"model": "classifier"}}},
+        kwargs={"standard_logging_object": audit, "standard_callback_dynamic_params": {"turn_off_message_logging": redact}},
+    ))
+    if not store_prompts or redact:
+        assert "classifier_input" not in stored
+        assert "originating_request_masked" not in stored
+    else:
+        assert stored["classifier_input"]["messages"] == audit["classifier_input"]["messages"]
+        assert LITELLM_TRUNCATED_PAYLOAD_FIELD in json.dumps(stored["classifier_input"])
+        assert stored["originating_request_masked"]["input"] == "source-only"
+        assert stored["model"] == "classifier"
+        assert audit["classifier_input"]["system"] == "rubric" * 1000
+
+
 def test_get_logging_payload_maps_openai_cached_tokens_to_cache_read_input_tokens():
     additional_usage_values = _get_additional_usage_values_for_usage(
         litellm.Usage(
@@ -81,6 +107,48 @@ def test_get_logging_payload_maps_openai_cached_tokens_to_cache_read_input_token
     assert additional_usage_values["prompt_tokens_details"]["cached_tokens"] == 123
 
 
+class _HashingCache(litellm.Cache):
+    def __init__(self) -> None:
+        pass
+
+    def get_cache_key(self, **kwargs) -> str:
+        raise AssertionError("a preset cache key must be reused instead of hashing the request")
+
+
+def _cache_key_in_spend_log(monkeypatch: pytest.MonkeyPatch, cache: litellm.Cache | None, preset: str | None) -> str:
+    monkeypatch.setattr(litellm, "cache", cache)
+    payload: Final = get_logging_payload(
+        kwargs={
+            "model": "gpt-4o-mini",
+            "messages": [{"role": "user", "content": "x" * 10_000}],
+            "litellm_params": {"metadata": {"user_api_key": "test-key"}, "preset_cache_key": preset},
+        },
+        response_obj=litellm.ModelResponse(id="chatcmpl-test", choices=[], usage=litellm.Usage()),
+        start_time=datetime.datetime.now(timezone.utc),
+        end_time=datetime.datetime.now(timezone.utc),
+    )
+    return payload["cache_key"]
+
+
+def test_get_logging_payload_reuses_the_preset_cache_key_instead_of_hashing_the_body(monkeypatch):
+    assert _cache_key_in_spend_log(monkeypatch, _HashingCache(), "preset-key") == "preset-key"
+
+
+def test_get_logging_payload_records_cache_off_without_hashing(monkeypatch):
+    assert _cache_key_in_spend_log(monkeypatch, None, None) == "Cache OFF"
+
+
+def test_get_logging_payload_still_hashes_when_caching_is_on_and_no_preset_key_exists(monkeypatch):
+    class _RecordingCache(litellm.Cache):
+        def __init__(self) -> None:
+            pass
+
+        def get_cache_key(self, **kwargs) -> str:
+            return "hashed-from-" + kwargs["model"]
+
+    assert _cache_key_in_spend_log(monkeypatch, _RecordingCache(), None) == "hashed-from-gpt-4o-mini"
+
+
 _TRACE_ONLY_STANDARD_LOGGING: Final = cast(
     StandardLoggingPayload,
     {
@@ -587,11 +655,11 @@ def test_sanitize_request_body_for_spend_logs_payload_circular_reference():
     assert sanitized == {"b": {"a": {}}}  # Should return empty dict for circular reference
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_vector_store_request_for_spend_logs_payload_store_prompts_true(
     mock_should_store,
 ):
-    # When _should_store_prompts_and_responses_in_spend_logs returns True
+    # When should_store_prompts_and_responses_in_spend_logs returns True
     mock_should_store.return_value = True
 
     # Sample vector store request metadata
@@ -605,11 +673,11 @@ def test_get_vector_store_request_for_spend_logs_payload_store_prompts_true(
     assert result[0]["vector_store_search_response"]["data"][0]["content"][0]["text"] == "sensitive information"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_vector_store_request_for_spend_logs_payload_store_prompts_false(
     mock_should_store,
 ):
-    # When _should_store_prompts_and_responses_in_spend_logs returns False
+    # When should_store_prompts_and_responses_in_spend_logs returns False
     mock_should_store.return_value = False
 
     # Sample vector store request metadata
@@ -625,7 +693,7 @@ def test_get_vector_store_request_for_spend_logs_payload_store_prompts_false(
     assert result[0]["vector_store_search_response"]["data"][0]["content"][0]["type"] == "text"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_vector_store_request_for_spend_logs_payload_null_input(mock_should_store):
     # When input is None
     mock_should_store.return_value = False
@@ -633,7 +701,7 @@ def test_get_vector_store_request_for_spend_logs_payload_null_input(mock_should_
     assert result is None
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_messages_for_spend_logs_realtime_returns_messages(mock_should_store):
     """
     Test that _get_messages_for_spend_logs_payload returns messages
@@ -660,7 +728,7 @@ def test_get_messages_for_spend_logs_realtime_returns_messages(mock_should_store
     assert parsed[1]["content"] == "What is the weather today?"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_messages_for_spend_logs_strips_null_bytes(mock_should_store):
     """Regression for PostgreSQL 22P05: NUL bytes must be stripped from messages."""
     mock_should_store.return_value = True
@@ -677,7 +745,7 @@ def test_get_messages_for_spend_logs_strips_null_bytes(mock_should_store):
     assert parsed[0]["content"] == "helloworld"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_messages_for_spend_logs_realtime_empty_when_disabled(mock_should_store):
     """
     Test that _get_messages_for_spend_logs_payload returns '{}' for realtime calls
@@ -695,7 +763,7 @@ def test_get_messages_for_spend_logs_realtime_empty_when_disabled(mock_should_st
     assert result == "{}"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_messages_for_spend_logs_non_realtime_returns_empty(mock_should_store):
     """
     Test that _get_messages_for_spend_logs_payload returns '{}' for non-realtime
@@ -713,7 +781,7 @@ def test_get_messages_for_spend_logs_non_realtime_returns_empty(mock_should_stor
     assert result == "{}"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_response_for_spend_logs_payload_truncates_large_base64(mock_should_store):
     from litellm.constants import MAX_STRING_LENGTH_PROMPT_IN_DB
 
@@ -741,7 +809,7 @@ def test_get_response_for_spend_logs_payload_truncates_large_base64(mock_should_
     assert parsed["data"][0]["other_field"] == "value"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_response_for_spend_logs_payload_strips_null_bytes(mock_should_store):
     """Regression for PostgreSQL 22P05: NUL bytes must be stripped from response."""
     mock_should_store.return_value = True
@@ -754,7 +822,7 @@ def test_get_response_for_spend_logs_payload_strips_null_bytes(mock_should_store
     assert json.loads(response_json)["content"] == "answerhere"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_get_response_for_spend_logs_payload_truncates_large_embedding(
     mock_should_store,
 ):
@@ -809,7 +877,7 @@ def test_truncation_includes_db_safeguard_note():
     )
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_response_truncation_logs_info_message(mock_should_store):
     """
     Test that when response is truncated before DB storage, an info log is emitted
@@ -831,7 +899,7 @@ def test_response_truncation_logs_info_message(mock_should_store):
         assert "response was truncated" in log_msg
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_request_body_truncation_logs_info_message(mock_should_store):
     """
     Test that when request body is truncated before DB storage, an info log is emitted.
@@ -922,6 +990,88 @@ def test_safe_dumps_complex_metadata_like_object():
     assert parsed["model"] == "gpt-4"
 
 
+_RAW_MODEL_WITH_PROMPT: Final = "opus-4.6 Please summarize my medical records\nPatient has diabetes"
+
+
+_BEDROCK_INFERENCE_PROFILE_ARN: Final = (
+    "arn:aws:bedrock:us-east-1:123456789012:application-inference-profile/claude-sonnet-4-5"
+)
+_OVERLONG_MODEL: Final = "m" * (MAX_SPEND_LOG_MODEL_NAME_LENGTH + 1)
+
+
+@pytest.mark.parametrize(
+    ("requested_model", "failure", "expected_model"),
+    [
+        (
+            _RAW_MODEL_WITH_PROMPT,
+            ProxyModelNotFoundError(route="acompletion", model_name=_RAW_MODEL_WITH_PROMPT),
+            UNKNOWN_MODEL_SPEND_LOG_MODEL,
+        ),
+        (
+            _RAW_MODEL_WITH_PROMPT,
+            ValueError("Upstream passthrough request failed with status 404"),
+            UNKNOWN_MODEL_SPEND_LOG_MODEL,
+        ),
+        (_OVERLONG_MODEL, ValueError("provider timed out"), UNKNOWN_MODEL_SPEND_LOG_MODEL),
+        (
+            "gpt-5.2",
+            ProxyModelNotFoundError(route="acompletion", model_name="gpt-5.2"),
+            UNKNOWN_MODEL_SPEND_LOG_MODEL,
+        ),
+        ("gpt-5.2", ValueError("provider timed out"), "gpt-5.2"),
+        (_BEDROCK_INFERENCE_PROFILE_ARN, ValueError("provider timed out"), _BEDROCK_INFERENCE_PROFILE_ARN),
+    ],
+)
+def test_get_logging_payload_replaces_rejected_or_prompt_shaped_models_with_the_placeholder(
+    requested_model: str, failure: Exception, expected_model: str
+):
+    kwargs: Final = {
+        "model": requested_model,
+        "messages": [{"role": "user", "content": "hi"}],
+        "call_type": "acompletion",
+        "litellm_params": {"metadata": {"user_api_key": "sk-test", "status": "failure"}},
+    }
+
+    payload: Final = get_logging_payload(
+        kwargs=kwargs,
+        response_obj=failure,
+        start_time=datetime.datetime.now(timezone.utc),
+        end_time=datetime.datetime.now(timezone.utc),
+    )
+
+    assert payload["model"] == expected_model
+
+
+@pytest.mark.parametrize(
+    ("metadata", "response_obj"),
+    [
+        ({"user_api_key": "sk-test"}, litellm.ModelResponse(id="chatcmpl-test", choices=[])),
+        (
+            {"user_api_key": "sk-test", "model_group": "team alias", "status": "failure"},
+            ValueError("provider timed out"),
+        ),
+    ],
+)
+def test_get_logging_payload_keeps_a_whitespace_model_name_on_success_or_a_routed_failure(
+    metadata: dict[str, str], response_obj: litellm.ModelResponse | Exception
+):
+    kwargs: Final = {
+        "model": _RAW_MODEL_WITH_PROMPT,
+        "messages": [{"role": "user", "content": "hi"}],
+        "call_type": "acompletion",
+        "litellm_params": {"metadata": metadata},
+    }
+
+    payload: Final = get_logging_payload(
+        kwargs=kwargs,
+        response_obj=response_obj,
+        start_time=datetime.datetime.now(timezone.utc),
+        end_time=datetime.datetime.now(timezone.utc),
+    )
+
+    assert payload["model"] == _RAW_MODEL_WITH_PROMPT
+
+
 @patch("litellm.proxy.proxy_server.master_key", None)
 @patch("litellm.proxy.proxy_server.general_settings", {})
 def test_get_logging_payload_api_key_preserved_when_standard_logging_payload_is_none():
@@ -1412,7 +1562,7 @@ def test_get_logging_payload_handles_missing_overhead_gracefully():
     )
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_spend_logs_redacts_request_and_response_when_turn_off_message_logging_enabled(
     mock_should_store,
 ):
@@ -1476,7 +1626,7 @@ def test_should_store_prompts_and_responses_in_spend_logs_case_insensitive_strin
     mock_get_secret_bool,
 ):
     """
-    Test that _should_store_prompts_and_responses_in_spend_logs handles
+    Test that should_store_prompts_and_responses_in_spend_logs handles
     case-insensitive string values for store_prompts_in_spend_logs in general_settings.
     """
     # Test case-insensitive string "true" variations
@@ -1486,7 +1636,7 @@ def test_should_store_prompts_and_responses_in_spend_logs_case_insensitive_strin
             {"store_prompts_in_spend_logs": true_value},
         ):
             mock_get_secret_bool.return_value = False  # Ensure env var is False
-            result = _should_store_prompts_and_responses_in_spend_logs()
+            result = should_store_prompts_and_responses_in_spend_logs()
             assert result is True, f"Expected True for '{true_value}', got {result}"
 
     # Test boolean True
@@ -1495,7 +1645,7 @@ def test_should_store_prompts_and_responses_in_spend_logs_case_insensitive_strin
         {"store_prompts_in_spend_logs": True},
     ):
         mock_get_secret_bool.return_value = False
-        result = _should_store_prompts_and_responses_in_spend_logs()
+        result = should_store_prompts_and_responses_in_spend_logs()
         assert result is True, f"Expected True for boolean True, got {result}"
 
     # Test that non-true values fall back to environment variable
@@ -1506,22 +1656,22 @@ def test_should_store_prompts_and_responses_in_spend_logs_case_insensitive_strin
         ):
             # When env var is True, should return True
             mock_get_secret_bool.return_value = True
-            result = _should_store_prompts_and_responses_in_spend_logs()
+            result = should_store_prompts_and_responses_in_spend_logs()
             assert result is True, f"Expected True (from env var) for '{false_value}', got {result}"
 
             # When env var is False, should return False
             mock_get_secret_bool.return_value = False
-            result = _should_store_prompts_and_responses_in_spend_logs()
+            result = should_store_prompts_and_responses_in_spend_logs()
             assert result is False, f"Expected False (from env var) for '{false_value}', got {result}"
 
     # Test when general_settings doesn't have the key at all
     with patch("litellm.proxy.proxy_server.general_settings", {}):
         mock_get_secret_bool.return_value = True
-        result = _should_store_prompts_and_responses_in_spend_logs()
+        result = should_store_prompts_and_responses_in_spend_logs()
         assert result is True, "Expected True (from env var) when key missing, got False"
 
         mock_get_secret_bool.return_value = False
-        result = _should_store_prompts_and_responses_in_spend_logs()
+        result = should_store_prompts_and_responses_in_spend_logs()
         assert result is False, "Expected False (from env var) when key missing, got True"
 
 
@@ -1554,7 +1704,7 @@ def test_get_spend_logs_metadata_guardrail_info_fallback_from_metadata():
     assert result["guardrail_information"] is None
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_redacts_all_prompt_carrying_fields_when_flag_false(
     mock_should_store,
 ):
@@ -1590,7 +1740,7 @@ def test_sanitize_guardrail_information_redacts_all_prompt_carrying_fields_when_
     assert entry["guardrail_action"] == "NONE"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_redacts_prompt_fields_when_flag_false(
     mock_should_store,
 ):
@@ -1654,7 +1804,7 @@ def test_sanitize_guardrail_information_redacts_prompt_fields_when_flag_false(
     }
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_preserves_guardrail_usage_when_flag_false(
     mock_should_store,
 ):
@@ -1686,7 +1836,7 @@ def test_sanitize_guardrail_information_preserves_guardrail_usage_when_flag_fals
     assert entry["guardrail_usage"] == {"topicPolicyUnits": 1, "contentPolicyUnits": 1, "wordPolicyUnits": 0}
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_passthrough_when_flag_true(
     mock_should_store,
 ):
@@ -1709,13 +1859,13 @@ def test_sanitize_guardrail_information_passthrough_when_flag_true(
     assert result == guardrail_info
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_none_passthrough(mock_should_store):
     mock_should_store.return_value = False
     assert _sanitize_guardrail_information_for_spend_logs(None) is None
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_normalizes_bare_dict_input(mock_should_store):
     """
     Regression: xecguard (xecguard.py:246) assigns a bare dict to
@@ -1747,7 +1897,7 @@ def test_sanitize_guardrail_information_normalizes_bare_dict_input(mock_should_s
     assert entry["start_time"] == 1.0
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_drops_non_dict_items_in_list(mock_should_store):
     """
     A stray non-dict item in the list (e.g. from a buggy caller that
@@ -1766,7 +1916,7 @@ def test_sanitize_guardrail_information_drops_non_dict_items_in_list(mock_should
     assert result == [{"guardrail_name": "x", "guardrail_response": REDACTED_BY_LITELM_STRING}]
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_preserves_absent_prompt_fields(mock_should_store):
     """
     Entries that never carried guardrail_request or guardrail_response must
@@ -2182,7 +2332,7 @@ def test_sanitize_request_body_strips_secret_fields():
     assert sanitized["messages"] == [{"role": "user", "content": "hi"}]
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_proxy_server_request_payload_excludes_secret_fields(mock_should_store):
     """
     End-to-end test: when the proxy_server_request body contains
@@ -2262,7 +2412,7 @@ def test_redact_prompt_leaks_empty_string():
     assert _redact_prompt_leaks_in_error_string("") == ""
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_redacts_when_not_storing_prompts(
     mock_should_store,
 ):
@@ -2290,7 +2440,7 @@ def test_sanitize_error_information_redacts_when_not_storing_prompts(
     assert sanitized["llm_provider"] == "openai"
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_skips_redaction_when_storing_prompts(
     mock_should_store,
 ):
@@ -2312,7 +2462,7 @@ def test_sanitize_error_information_skips_redaction_when_storing_prompts(
     assert REDACTED_BY_LITELM_STRING not in sanitized["error_message"]
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_caps_size_regardless_of_prompt_flag(
     mock_should_store,
 ):
@@ -2343,7 +2493,7 @@ def test_sanitize_error_information_none_passthrough():
     assert _sanitize_error_information_for_spend_logs(None) is None
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_reproduces_lit_2992(mock_should_store):
     # Mirrors the reproduced row body from LIT-2992 — a RateLimitError whose
     # message embeds 178 pydantic validation errors, each carrying a full
@@ -2428,7 +2578,7 @@ def test_redact_prompt_leaks_handles_unterminated_value():
     assert REDACTED_BY_LITELM_STRING in redacted
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_redacts_traceback_when_not_storing_prompts(
     mock_should_store,
 ):
@@ -2460,7 +2610,7 @@ def test_sanitize_error_information_redacts_traceback_when_not_storing_prompts(
     assert "ValueError: invalid request" in sanitized["traceback"]
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_skips_traceback_redaction_when_storing_prompts(
     mock_should_store,
 ):
@@ -2568,7 +2718,7 @@ def test_redact_prompt_leaks_combined_quoted_key_and_pydantic_assignment():
     assert redacted.count(REDACTED_BY_LITELM_STRING) >= 2
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_error_information_redacts_pydantic_assignment_form(
     mock_should_store,
 ):
@@ -3164,7 +3314,7 @@ def test_get_logging_payload_hashes_bearer_prefixed_api_key():
     )
 
 
-@patch("litellm.proxy.spend_tracking.spend_tracking_utils._should_store_prompts_and_responses_in_spend_logs")
+@patch("litellm.proxy.spend_tracking.spend_tracking_utils.should_store_prompts_and_responses_in_spend_logs")
 def test_sanitize_guardrail_information_preserves_headroom_compression_token_stats(
     mock_should_store,
 ):
diff --git a/tests/test_litellm/proxy/test_budget_reservation.py b/tests/test_litellm/proxy/test_budget_reservation.py
index 6dab054d8ea..40ebc03781c 100644
--- a/tests/test_litellm/proxy/test_budget_reservation.py
+++ b/tests/test_litellm/proxy/test_budget_reservation.py
@@ -2220,6 +2220,15 @@ class _ExpiringRedisCache:
     async def async_delete_cache(self, key: str, *args: object, **kwargs: object) -> None:
         self.store.pop(key, None)
 
+    async def async_increment_pipeline(self, increment_list, **kwargs):
+        results = []
+        for op in increment_list:
+            results.append(await self.async_increment(op["key"], op["increment_value"]))
+        return results
+
+    def get_ttl(self, **kwargs) -> None:
+        return None
+
 
 @pytest.mark.asyncio
 async def test_reconcile_after_redis_counter_expiry_keeps_request_cost_enforced(
diff --git a/tests/test_litellm/proxy/test_collector.py b/tests/test_litellm/proxy/test_collector.py
new file mode 100644
index 00000000000..ac3e1f5e566
--- /dev/null
+++ b/tests/test_litellm/proxy/test_collector.py
@@ -0,0 +1,229 @@
+import asyncio
+import logging
+from collections.abc import Callable, Iterator
+from pathlib import Path
+from typing import Final
+
+import pytest
+import uvloop
+
+from litellm._logging import verbose_logger, verbose_proxy_logger, verbose_router_logger
+from litellm.proxy.collector import (
+    SpendEventConsumer,
+    address_argument,
+    apply_log_level,
+    pod_pgbouncer_database_url,
+)
+from litellm.proxy.db.pgbouncer import PgBouncerError, PgBouncerSettings
+from litellm.proxy.spend_tracking.spend_event_producer import (
+    AddressError,
+    SpendEventProducer,
+    TcpAddress,
+    UnixAddress,
+    open_collector_connection,
+)
+
+
+class _Handler:
+    def __init__(self, fail_on: bytes | None = None) -> None:
+        self.lines: list[bytes] = []  # mutable-ok: test double records the events the consumer handed over
+        self._fail_on = fail_on
+
+    async def __call__(self, line: bytes) -> None:
+        if line == self._fail_on:
+            raise RuntimeError("pipeline failed")
+        self.lines.append(line)
+
+
+async def _no_fallback(line: bytes) -> None:
+    raise AssertionError(f"unexpected fallback for {line!r}")
+
+
+class _Fallback:
+    def __init__(self) -> None:
+        self.lines: list[bytes] = []  # mutable-ok: test double records the events run in-process
+
+    async def __call__(self, line: bytes) -> None:
+        self.lines.append(line)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("transport", ["unix", "tcp"])
+async def test_consumer_handles_each_producer_line_once_in_order(tmp_path: Path, transport: str):
+    handler: Final = _Handler(fail_on=b"event-3\n")
+    consumer: Final = SpendEventConsumer(handler)
+    server: Final = await consumer.serve(
+        UnixAddress(path=str(tmp_path / "spend.sock")) if transport == "unix" else TcpAddress("127.0.0.1", 0)
+    )
+    address: Final = (
+        UnixAddress(path=str(tmp_path / "spend.sock"))
+        if transport == "unix"
+        else TcpAddress("127.0.0.1", server.sockets[0].getsockname()[1])
+    )
+    producer: Final = SpendEventProducer(
+        address=address, on_unavailable="fallback", buffer_size=100, connect_timeout=1.0, fallback=_no_fallback
+    )
+    for i in range(6):
+        await producer.publish(f"event-{i}\n".encode())
+    await producer.close(drain_timeout=5.0)
+
+    server.close()
+    assert await consumer.drain(timeout=5.0) == 0
+    assert handler.lines == [f"event-{i}\n".encode() for i in range(6) if i != 3]
+    assert (consumer.received, consumer.handled, consumer.failed) == (6, 5, 1)
+
+
+@pytest.mark.asyncio
+async def test_consumer_discards_a_truncated_trailing_event(tmp_path: Path):
+    handler: Final = _Handler()
+    consumer: Final = SpendEventConsumer(handler)
+    address: Final = UnixAddress(path=str(tmp_path / "spend.sock"))
+    server: Final = await consumer.serve(address)
+    _, writer = await open_collector_connection(address, timeout=1.0)
+    writer.write(b"whole\npartial-without-newline")
+    await writer.drain()
+    writer.close()
+    await writer.wait_closed()
+    await asyncio.sleep(0.05)
+
+    server.close()
+    assert await consumer.drain(timeout=5.0) == 0
+    assert handler.lines == [b"whole\n"]
+    assert consumer.received == 1
+
+
+@pytest.mark.asyncio
+async def test_drain_reports_producers_still_connected_after_the_timeout(tmp_path: Path):
+    consumer: Final = SpendEventConsumer(_Handler())
+    address: Final = UnixAddress(path=str(tmp_path / "spend.sock"))
+    server: Final = await consumer.serve(address)
+    _, writer = await open_collector_connection(address, timeout=1.0)
+    await asyncio.sleep(0.05)
+
+    server.close()
+    assert await consumer.drain(timeout=0.1) == 1
+    writer.close()
+    await writer.wait_closed()
+    assert await consumer.drain(timeout=5.0) == 0
+
+
+@pytest.mark.asyncio
+async def test_graceful_stop_hands_the_producer_over_to_its_fallback_without_losing_events(tmp_path: Path):
+    handler: Final = _Handler()
+    fallback: Final = _Fallback()
+    consumer: Final = SpendEventConsumer(handler)
+    address: Final = UnixAddress(path=str(tmp_path / "spend.sock"))
+    server: Final = await consumer.serve(address)
+    producer: Final = SpendEventProducer(
+        address=address, on_unavailable="fallback", buffer_size=100, connect_timeout=1.0, fallback=fallback
+    )
+    await producer.publish(b"event-1\n")
+    await asyncio.sleep(0.05)
+
+    server.close()
+    draining: Final = asyncio.ensure_future(consumer.drain(timeout=5.0))
+    await asyncio.sleep(0.05)
+    await producer.publish(b"event-2\n")
+    await producer.close(drain_timeout=5.0)
+
+    assert await draining == 0
+    assert handler.lines == [b"event-1\n"]
+    assert fallback.lines == [b"event-2\n"]
+    assert (producer.stats().sent, producer.stats().fallback) == (1, 1)
+
+
+@pytest.mark.parametrize("loop_factory", [asyncio.new_event_loop, uvloop.new_event_loop], ids=["asyncio", "uvloop"])
+def test_drain_still_hands_over_live_producers_when_another_connection_already_died(
+    tmp_path: Path, loop_factory: Callable[[], asyncio.AbstractEventLoop]
+):
+    """A transport the loop force-closed under a busy handler must not abort the half-close of the others."""
+
+    async def scenario() -> tuple[int, list[bytes]]:
+        release: Final = asyncio.Event()
+
+        async def slow_handler(line: bytes) -> None:
+            await release.wait()
+
+        consumer: Final = SpendEventConsumer(slow_handler)
+        address: Final = UnixAddress(path=str(tmp_path / "spend.sock"))
+        server: Final = await consumer.serve(address)
+        _, dead = await open_collector_connection(address, timeout=1.0)
+        dead.write(b"stuck\n")
+        await dead.drain()
+        await asyncio.sleep(0.05)
+        for connection in consumer._open_connections:  # pyright: ignore[reportPrivateUsage]  # force-close like uvloop does on a socket error
+            connection.transport.close()
+        dead.close()
+        fallback: Final = _Fallback()
+        producer: Final = SpendEventProducer(
+            address=address, on_unavailable="fallback", buffer_size=100, connect_timeout=1.0, fallback=fallback
+        )
+        await producer.publish(b"event-1\n")
+        await asyncio.sleep(0.05)
+
+        server.close()
+        draining: Final = asyncio.ensure_future(consumer.drain(timeout=0.5))
+        await asyncio.sleep(0.05)
+        await producer.publish(b"event-2\n")
+        await producer.close(drain_timeout=5.0)
+        still_open: Final = await draining
+        release.set()
+        await asyncio.sleep(0.05)
+        return still_open, fallback.lines
+
+    with asyncio.Runner(loop_factory=loop_factory) as runner:
+        still_open, fallback_lines = runner.run(scenario())
+
+    assert still_open == 2
+    assert fallback_lines == [b"event-2\n"]
+
+
+def test_address_argument():
+    assert address_argument((), default="unix:///tmp/x.sock") == "unix:///tmp/x.sock"
+    assert address_argument(("--address", "tcp://127.0.0.1:4100"), default="unix:///tmp/x.sock") == (
+        "tcp://127.0.0.1:4100"
+    )
+    assert isinstance(address_argument(("--listen", "x"), default="unix:///tmp/x.sock"), AddressError)
+
+
+def test_pod_pgbouncer_database_url_points_at_the_proxy_containers_pooler():
+    """With pgbouncer on, the sidecar must not open its own upstream connections but share the pod's pooler."""
+    upstream: Final = "postgresql://u:p@db.internal:5432/litellm?schema=public"
+    environ: Final = {"DATABASE_URL": upstream}
+    assert pod_pgbouncer_database_url(PgBouncerSettings(enabled=False), environ, token_auth=False) is None
+    assert (
+        pod_pgbouncer_database_url(PgBouncerSettings(enabled=True, port=6543), environ, token_auth=False)
+        == "postgresql://u:p@127.0.0.1:6543/litellm?schema=public&pgbouncer=true"
+    )
+    assert isinstance(pod_pgbouncer_database_url(PgBouncerSettings(enabled=True), {}, token_auth=False), PgBouncerError)
+
+
+def test_pod_pgbouncer_database_url_goes_direct_under_token_auth():
+    """The proxy's pgbouncer only knows the token that container minted, so the sidecar must mint its own upstream."""
+    iam_upstream: Final = "postgresql://u@db.internal:5432/litellm?schema=public"
+    assert (
+        pod_pgbouncer_database_url(PgBouncerSettings(enabled=True), {"DATABASE_URL": iam_upstream}, token_auth=True)
+        is None
+    )
+    assert pod_pgbouncer_database_url(PgBouncerSettings(enabled=True), {}, token_auth=True) is None
+
+
+@pytest.fixture
+def restore_log_levels() -> Iterator[None]:
+    loggers: Final = (verbose_logger, verbose_router_logger, verbose_proxy_logger)
+    levels: Final = tuple(logger.level for logger in loggers)
+    yield
+    for logger, level in zip(loggers, levels, strict=True):
+        logger.setLevel(level)
+
+
+@pytest.mark.usefixtures("restore_log_levels")
+@pytest.mark.parametrize(
+    ("litellm_log", "expected"),
+    [("DEBUG", logging.DEBUG), ("info", logging.INFO), (None, logging.WARNING), ("loud", logging.WARNING)],
+)
+def test_apply_log_level_mirrors_the_proxy_env_contract(litellm_log: str | None, expected: int):
+    verbose_proxy_logger.setLevel(logging.WARNING)
+    apply_log_level(litellm_log)
+    assert verbose_proxy_logger.isEnabledFor(expected)
+    assert not verbose_proxy_logger.isEnabledFor(expected - 10)
diff --git a/tests/test_litellm/proxy/test_common_request_processing.py b/tests/test_litellm/proxy/test_common_request_processing.py
index be666607823..50b26577e5c 100644
--- a/tests/test_litellm/proxy/test_common_request_processing.py
+++ b/tests/test_litellm/proxy/test_common_request_processing.py
@@ -3,7 +3,7 @@ import copy
 import datetime
 import json
 from types import MappingProxyType, SimpleNamespace
-from typing import AsyncGenerator, Callable, Final, Optional
+from typing import AsyncGenerator, Callable, Final, Iterator, Optional
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import httpx
@@ -417,7 +417,7 @@ class TestProxyBaseLLMRequestProcessing:
         )
 
         fake_llm_router = MagicMock()
-        fake_llm_router.get_model_list.return_value = [
+        fake_llm_router.deployments_for_request.return_value = [
             {
                 "model_name": "smart-router",
                 "litellm_params": {
@@ -8307,3 +8307,116 @@ async def test_handle_llm_api_exception_forwards_provider_headers_on_http_status
 
     assert exc_info.value.headers is not None
     assert exc_info.value.headers["llm_provider-x-amzn-requestid"] == "req-passthrough-500"
+
+
+class TestBackgroundResponseRetrievalGovernance:
+    """LIT-7175: retrieving a background Response attaches the model's post_call policy pipelines."""
+
+    GOVERNED_MODEL_GROUP = "gpt-5.4-mini"
+    GOVERNED_MODEL_ID = "deployment-governed"
+
+    @pytest.fixture
+    def policy_engine(self) -> Iterator[None]:
+        from litellm.proxy.policy_engine.attachment_registry import get_attachment_registry
+        from litellm.proxy.policy_engine.policy_registry import get_policy_registry
+
+        get_policy_registry().load_policies(
+            {
+                "response-governance": {
+                    "guardrails": {"add": ["output-word-filter"]},
+                    "pipeline": {
+                        "mode": "post_call",
+                        "steps": [{"guardrail": "output-word-filter", "on_pass": "allow", "on_fail": "block"}],
+                    },
+                }
+            }
+        )
+        get_attachment_registry().load_attachments(
+            [{"policy": "response-governance", "models": [self.GOVERNED_MODEL_GROUP]}]
+        )
+        yield
+        get_policy_registry().clear()
+        get_attachment_registry().clear()
+
+    def _router(self) -> MagicMock:
+        from litellm.types.router import Deployment, LiteLLM_Params
+
+        router = MagicMock()
+        router.get_deployment.side_effect = lambda model_id: (
+            Deployment(
+                model_name=self.GOVERNED_MODEL_GROUP,
+                litellm_params=LiteLLM_Params(model=f"openai/{self.GOVERNED_MODEL_GROUP}"),
+                model_info={"id": model_id},
+            )
+            if model_id == self.GOVERNED_MODEL_ID
+            else None
+        )
+        return router
+
+    async def _pre_call(self, route_type: str, monkeypatch: pytest.MonkeyPatch) -> dict[str, object]:
+        from litellm.responses.utils import ResponsesAPIRequestUtils
+
+        client_facing_response_id = "resp_opaque-client-facing-id"
+        encoded_response_id = ResponsesAPIRequestUtils._build_responses_api_response_id(
+            custom_llm_provider="openai", model_id=self.GOVERNED_MODEL_ID, response_id="resp_upstream"
+        )
+        processing_obj = ProxyBaseLLMRequestProcessing(
+            data={"response_id": client_facing_response_id, "litellm_metadata": {}}
+        )
+        mock_request = MagicMock(spec=Request)
+        mock_request.headers = {}
+
+        async def passthrough_add_litellm_data_to_request(
+            data: dict[str, object], **kwargs: object
+        ) -> dict[str, object]:
+            return data
+
+        async def decrypting_pre_call_hook(
+            user_api_key_dict: ProxyUserAPIKeyAuth, data: dict[str, object], call_type: str
+        ) -> dict[str, object]:
+            if data.get("response_id") == client_facing_response_id:
+                data["response_id"] = encoded_response_id
+            return data
+
+        monkeypatch.setattr(
+            litellm.proxy.common_request_processing,
+            "add_litellm_data_to_request",
+            passthrough_add_litellm_data_to_request,
+        )
+        proxy_logging_obj = MagicMock(spec=ProxyLogging)
+        proxy_logging_obj.pre_call_hook = AsyncMock(side_effect=decrypting_pre_call_hook)
+        proxy_config = MagicMock(spec=ProxyConfig)
+        proxy_config._get_hierarchical_router_settings = AsyncMock(return_value=None)
+        returned_data, _ = await processing_obj.common_processing_pre_call_logic(
+            request=mock_request,
+            general_settings={},
+            user_api_key_dict=ProxyUserAPIKeyAuth(),
+            proxy_logging_obj=proxy_logging_obj,
+            proxy_config=proxy_config,
+            route_type=route_type,
+            llm_router=self._router(),
+        )
+        return returned_data
+
+    @pytest.mark.asyncio
+    async def test_retrieving_a_background_response_attaches_its_model_post_call_pipeline(
+        self, policy_engine: None, monkeypatch: pytest.MonkeyPatch
+    ) -> None:
+        data = await self._pre_call("aget_responses", monkeypatch)
+
+        assert data["response_id"].startswith("resp_bGl0ZWxsbTpjdXN0b21f")
+        pipelines = data["litellm_metadata"]["_guardrail_pipelines"]
+        assert [(policy_name, [step.guardrail for step in pipeline.steps]) for policy_name, pipeline in pipelines] == [
+            ("response-governance", ["output-word-filter"])
+        ]
+        assert data["litellm_metadata"]["applied_policies"] == ["response-governance"]
+        assert data["model"] is None
+
+    @pytest.mark.asyncio
+    async def test_submitting_a_response_does_not_attach_pipelines_from_its_response_id(
+        self, policy_engine: None, monkeypatch: pytest.MonkeyPatch
+    ) -> None:
+        data = await self._pre_call("aresponses", monkeypatch)
+
+        assert "_guardrail_pipelines" not in data["litellm_metadata"]
+        assert "applied_policies" not in data["litellm_metadata"]
diff --git a/tests/test_litellm/proxy/test_health_check_functions.py b/tests/test_litellm/proxy/test_health_check_functions.py
index fdae11d517a..5aa80213134 100644
--- a/tests/test_litellm/proxy/test_health_check_functions.py
+++ b/tests/test_litellm/proxy/test_health_check_functions.py
@@ -6,6 +6,8 @@ from unittest.mock import AsyncMock, MagicMock, patch
 import pytest
 
 
+from litellm.proxy._types import UserAPIKeyAuth
+from litellm.proxy.db.health_check_latest import LatestHealthCheckRow
 from litellm.proxy.health_endpoints._health_endpoints import (
     _aggregate_health_check_results,
     _build_model_param_to_info_mapping,
@@ -13,6 +15,7 @@ from litellm.proxy.health_endpoints._health_endpoints import (
     _save_background_health_checks_to_db,
     _save_health_check_results_if_changed,
     _save_health_check_to_db,
+    latest_health_checks_endpoint,
 )
 from litellm.proxy.utils import PrismaClient
 
@@ -21,12 +24,8 @@ from litellm.proxy.utils import PrismaClient
 def mock_prisma():
     """Simplified mock PrismaClient with bound methods"""
     client = MagicMock()
-    client.db.litellm_healthchecktable.create = AsyncMock(
-        return_value={"id": "test-id"}
-    )
-    client.db.litellm_healthchecktable.find_many = AsyncMock(
-        return_value=[{"id": "1", "model_name": "test"}]
-    )
+    client.db.litellm_healthchecktable.create = AsyncMock(return_value={"id": "test-id"})
+    client.db.litellm_healthchecktable.find_many = AsyncMock(return_value=[{"id": "1", "model_name": "test"}])
 
     # Bind actual methods
     import types
@@ -52,14 +51,10 @@ def mock_prisma():
         ("healthy", 1, 0, False),  # Database error case
     ],
 )
-async def test_save_health_check_result(
-    mock_prisma, status, healthy, unhealthy, should_succeed
-):
+async def test_save_health_check_result(mock_prisma, status, healthy, unhealthy, should_succeed):
     """Test health check result saving with various scenarios"""
     if not should_succeed:
-        mock_prisma.db.litellm_healthchecktable.create.side_effect = Exception(
-            "DB Error"
-        )
+        mock_prisma.db.litellm_healthchecktable.create.side_effect = Exception("DB Error")
 
     result = await mock_prisma.save_health_check_result(
         model_name="test-model",
@@ -187,9 +182,7 @@ def test_aggregate_health_check_results():
         {"model": "gpt-4", "error": "Rate limit exceeded"},
     ]
 
-    result = _aggregate_health_check_results(
-        model_param_to_info, healthy_endpoints, unhealthy_endpoints
-    )
+    result = _aggregate_health_check_results(model_param_to_info, healthy_endpoints, unhealthy_endpoints)
 
     # Check gpt-3.5-turbo is healthy
     gpt35_key = ("model-123", "gpt-3.5-turbo")
@@ -220,9 +213,7 @@ def test_aggregate_health_check_results_multiple_endpoints():
     ]
     unhealthy_endpoints = []
 
-    result = _aggregate_health_check_results(
-        model_param_to_info, healthy_endpoints, unhealthy_endpoints
-    )
+    result = _aggregate_health_check_results(model_param_to_info, healthy_endpoints, unhealthy_endpoints)
 
     key = ("model-123", "gpt-3.5-turbo")
     assert result[key]["healthy_count"] == 2
@@ -398,7 +389,7 @@ async def test_save_background_health_checks_to_db():
 
     start_time = 1234567890.0
 
-    await _save_background_health_checks_to_db(
+    persisted = await _save_background_health_checks_to_db(
         mock_prisma,
         model_list,
         healthy_endpoints,
@@ -407,7 +398,8 @@ async def test_save_background_health_checks_to_db():
         "background_health_check",
     )
 
-    # Should call get_all_latest_health_checks and save_health_check_result
+    # Should call get_all_latest_health_checks and save_health_check_result, and report completion
+    assert persisted is True
     mock_prisma.get_all_latest_health_checks.assert_called_once()
     mock_prisma.save_health_check_result.assert_called_once()
 
@@ -418,22 +410,112 @@ async def test_save_background_health_checks_to_db():
     assert call_kwargs["checked_by"] == "background_health_check"
 
 
+def _two_model_results():
+    return {
+        ("model-1", "gpt-4"): {
+            "model_name": "gpt-4",
+            "model_id": "model-1",
+            "healthy_count": 1,
+            "unhealthy_count": 0,
+            "error_message": None,
+        },
+        ("model-2", "gpt-4o"): {
+            "model_name": "gpt-4o",
+            "model_id": "model-2",
+            "healthy_count": 0,
+            "unhealthy_count": 1,
+            "error_message": "boom",
+        },
+    }
+
+
+@pytest.mark.asyncio
+async def test_save_health_check_results_if_changed_awaits_every_write_and_reports_success():
+    """Writes are awaited, not detached, so the caller can tell the cycle's persistence completed."""
+    mock_prisma = MagicMock()
+    mock_prisma.save_health_check_result = AsyncMock(return_value={"id": "row"})
+
+    persisted = await _save_health_check_results_if_changed(
+        mock_prisma, _two_model_results(), {}, 1234567890.0, "background_health_check"
+    )
+
+    assert (persisted, mock_prisma.save_health_check_result.await_count) == (True, 2)
+
+
+@pytest.mark.asyncio
+async def test_save_health_check_results_if_changed_reports_failure_when_a_write_returns_none():
+    """save_health_check_result swallows DB errors and returns None; that must surface as False."""
+    mock_prisma = MagicMock()
+    mock_prisma.save_health_check_result = AsyncMock(side_effect=[{"id": "row"}, None])
+
+    persisted = await _save_health_check_results_if_changed(
+        mock_prisma, _two_model_results(), {}, 1234567890.0, "background_health_check"
+    )
+
+    assert (persisted, mock_prisma.save_health_check_result.await_count) == (False, 2)
+
+
+@pytest.mark.asyncio
+async def test_save_health_check_results_if_changed_reports_success_when_nothing_needed_writing():
+    mock_prisma = MagicMock()
+    mock_prisma.save_health_check_result = AsyncMock()
+    model_results = {
+        ("model-1", "gpt-4"): {
+            "model_name": "gpt-4",
+            "model_id": "model-1",
+            "healthy_count": 1,
+            "unhealthy_count": 0,
+            "error_message": None,
+        },
+    }
+    latest_checks_map = {
+        "model-1": MagicMock(status="healthy", checked_at=datetime.now(timezone.utc) - timedelta(minutes=5)),
+    }
+
+    persisted = await _save_health_check_results_if_changed(
+        mock_prisma, model_results, latest_checks_map, 1234567890.0, "background_health_check"
+    )
+
+    assert (persisted, mock_prisma.save_health_check_result.await_count) == (True, 0)
+
+
+def _one_model_setup():
+    model_list = [
+        {
+            "model_name": "gpt-3.5-turbo",
+            "model_info": {"id": "model-123"},
+            "litellm_params": {"model": "gpt-3.5-turbo"},
+        },
+    ]
+    return model_list, [{"model": "gpt-3.5-turbo"}], []
+
+
+@pytest.mark.asyncio
+async def test_save_background_health_checks_to_db_returns_false_when_a_write_fails():
+    mock_prisma = MagicMock()
+    mock_prisma.get_all_latest_health_checks = AsyncMock(return_value=[])
+    mock_prisma.save_health_check_result = AsyncMock(return_value=None)
+    model_list, healthy_endpoints, unhealthy_endpoints = _one_model_setup()
+
+    persisted = await _save_background_health_checks_to_db(
+        mock_prisma, model_list, healthy_endpoints, unhealthy_endpoints, 1234567890.0, "background_health_check"
+    )
+
+    assert (persisted, mock_prisma.save_health_check_result.await_count) == (False, 1)
+
+
 @pytest.mark.asyncio
 async def test_save_background_health_checks_to_db_no_prisma():
     """Test graceful handling when no prisma client"""
-    result = await _save_background_health_checks_to_db(
-        None, [], [], [], 0.0, "background_health_check"
-    )
-    assert result is None
+    result = await _save_background_health_checks_to_db(None, [], [], [], 0.0, "background_health_check")
+    assert result is False
 
 
 @pytest.mark.asyncio
 async def test_save_background_health_checks_to_db_exception_handling():
     """Test exception handling in background health check save"""
     mock_prisma = MagicMock()
-    mock_prisma.get_all_latest_health_checks = AsyncMock(
-        side_effect=Exception("DB Error")
-    )
+    mock_prisma.get_all_latest_health_checks = AsyncMock(side_effect=Exception("DB Error"))
 
     model_list = [
         {
@@ -443,104 +525,134 @@ async def test_save_background_health_checks_to_db_exception_handling():
         },
     ]
 
-    # Should not raise exception, should handle gracefully
-    await _save_background_health_checks_to_db(
+    # Must not raise (the health check loop has to survive a DB outage) but must report
+    # the failure, so the window lock can be released for another pod to retry
+    persisted = await _save_background_health_checks_to_db(
         mock_prisma, model_list, [], [], 0.0, "background_health_check"
     )
 
-    # Function should complete without raising
+    assert persisted is False
+
+
+def _raw_latest_row(model_name: str, model_id, checked_at: datetime) -> dict:
+    return {
+        "health_check_id": f"hc-{model_id or 'no-id'}-{model_name}",
+        "model_name": model_name,
+        "model_id": model_id,
+        "status": "healthy",
+        "healthy_count": 1,
+        "unhealthy_count": 0,
+        "error_message": None,
+        "response_time_ms": 10.0,
+        "details": None,
+        "checked_by": "pod-1",
+        "checked_at": checked_at.isoformat(),
+        "created_at": checked_at.isoformat(),
+        "updated_at": checked_at.isoformat(),
+    }
 
 
 @pytest.mark.asyncio
-async def test_get_all_latest_health_checks_with_model_id(mock_prisma):
-    """Test get_all_latest_health_checks properly groups by model_id"""
-    mock_check2 = MagicMock()
-    mock_check2.model_id = "model-456"
-    mock_check2.model_name = "gpt-3.5-turbo"
-    mock_check2.checked_at = datetime.now(timezone.utc) - timedelta(minutes=5)
-
-    mock_check3 = MagicMock()
-    mock_check3.model_id = "model-123"
-    mock_check3.model_name = "gpt-3.5-turbo"
-    mock_check3.checked_at = datetime.now(timezone.utc) - timedelta(
-        minutes=1
-    )  # Latest for model-123
-
-    # Order by checked_at desc
-    mock_prisma.db.litellm_healthchecktable.find_many = AsyncMock(
-        return_value=[mock_check3, mock_check2]
-    )
-
-    result = await mock_prisma.get_all_latest_health_checks()
-
-    # Should return 2 unique models (by model_id)
-    assert len(result) == 2
-
-    # Should have latest check for each model_id
-    model_ids = {check.model_id for check in result}
-    assert "model-123" in model_ids
-    assert "model-456" in model_ids
-
-    # model-123 should have the latest check (1 minute ago)
-    model123_check = next(c for c in result if c.model_id == "model-123")
-    assert model123_check.checked_at == mock_check3.checked_at
-
-
-@pytest.mark.asyncio
-async def test_get_all_latest_health_checks_without_model_id(mock_prisma):
-    """Test get_all_latest_health_checks groups by model_name when model_id is None"""
-    mock_check2 = MagicMock()
-    mock_check2.model_id = None
-    mock_check2.model_name = "gpt-3.5-turbo"
-    mock_check2.checked_at = datetime.now(timezone.utc) - timedelta(minutes=1)  # Latest
-
-    mock_prisma.db.litellm_healthchecktable.find_many = AsyncMock(
-        return_value=[mock_check2]
-    )
-
-    result = await mock_prisma.get_all_latest_health_checks()
-
-    # Should return 1 unique model (by model_name)
-    assert len(result) == 1
-    assert result[0].model_name == "gpt-3.5-turbo"
-    assert result[0].checked_at == mock_check2.checked_at  # Latest
-
-
-@pytest.mark.asyncio
-async def test_get_all_latest_health_checks_same_name_with_and_without_model_id(
-    mock_prisma,
-):
+async def test_get_all_latest_health_checks_keeps_every_distinct_group_with_its_own_checked_at(mock_prisma):
     """
-    Same model_name can appear twice after DISTINCT ON: once keyed by (model_id, name)
-    and once by (NULL, name) — different Postgres groups than a single row with id.
+    Postgres owns the dedup. (id, name), (other id, name) and (NULL, name) are distinct groups and each row
+    must arrive typed, with its own checked_at, for the 1h re-save compare and the id-or-name lookup key.
     """
     now = datetime.now(timezone.utc)
-    with_id = MagicMock()
-    with_id.model_id = "deployment-abc"
-    with_id.model_name = "gpt-4"
-    with_id.checked_at = now - timedelta(minutes=2)
-
-    without_id = MagicMock()
-    without_id.model_id = None
-    without_id.model_name = "gpt-4"
-    without_id.checked_at = now - timedelta(minutes=1)
-
-    mock_prisma.db.litellm_healthchecktable.find_many = AsyncMock(
-        return_value=[without_id, with_id]
+    mock_prisma.db.query_raw = AsyncMock(
+        return_value=[
+            _raw_latest_row("gpt-3.5-turbo", "model-123", now - timedelta(minutes=1)),
+            _raw_latest_row("gpt-3.5-turbo", "model-456", now - timedelta(minutes=5)),
+            _raw_latest_row("gpt-4", "deployment-abc", now - timedelta(minutes=2)),
+            _raw_latest_row("gpt-4", None, now - timedelta(minutes=3)),
+        ]
     )
 
     result = await mock_prisma.get_all_latest_health_checks()
 
-    assert len(result) == 2
-    names = {r.model_name for r in result}
-    assert names == {"gpt-4"}
-    ids = {r.model_id for r in result}
-    assert "deployment-abc" in ids
-    assert None in ids
+    assert {(check.model_id, check.model_name): check.checked_at for check in result} == {
+        ("model-123", "gpt-3.5-turbo"): now - timedelta(minutes=1),
+        ("model-456", "gpt-3.5-turbo"): now - timedelta(minutes=5),
+        ("deployment-abc", "gpt-4"): now - timedelta(minutes=2),
+        (None, "gpt-4"): now - timedelta(minutes=3),
+    }
 
-    by_key = {(r.model_id, r.model_name): r for r in result}
-    assert by_key[("deployment-abc", "gpt-4")].checked_at == with_id.checked_at
-    assert by_key[(None, "gpt-4")].checked_at == without_id.checked_at
+
+@pytest.mark.asyncio
+async def test_save_background_health_checks_compares_raw_checked_at_against_utc_now(mock_prisma):
+    """
+    Raw rows carry ISO strings and the engine may omit the offset. A naive checked_at would TypeError
+    inside the 1h compare, be swallowed, and silently stop every save; a stale row must still re-save.
+    """
+    stale = (datetime.now(timezone.utc) - timedelta(hours=2)).replace(tzinfo=None)
+    fresh = datetime.now(timezone.utc) - timedelta(minutes=5)
+    mock_prisma.db.query_raw = AsyncMock(
+        return_value=[
+            _raw_latest_row("stale-model", "stale-id", stale),
+            _raw_latest_row("fresh-model", "fresh-id", fresh),
+        ]
+    )
+    mock_prisma.save_health_check_result = AsyncMock()
+    model_list = [
+        {"model_name": "stale-model", "model_info": {"id": "stale-id"}, "litellm_params": {"model": "openai/stale"}},
+        {"model_name": "fresh-model", "model_info": {"id": "fresh-id"}, "litellm_params": {"model": "openai/fresh"}},
+    ]
+
+    await _save_background_health_checks_to_db(
+        mock_prisma,
+        model_list,
+        [{"model": "openai/stale"}, {"model": "openai/fresh"}],
+        [],
+        time.time(),
+        "pod-1",
+    )
+    await asyncio.sleep(0)
+
+    assert [call.kwargs["model_id"] for call in mock_prisma.save_health_check_result.await_args_list] == ["stale-id"]
+
+
+@pytest.mark.asyncio
+async def test_latest_health_checks_endpoint_serialises_raw_rows(monkeypatch):
+    row = LatestHealthCheckRow(
+        health_check_id="hc-1",
+        model_name="gpt-4",
+        model_id="deployment-abc",
+        status="healthy",
+        healthy_count=1,
+        unhealthy_count=0,
+        error_message=None,
+        response_time_ms=12.5,
+        details='{"region": "eu"}',
+        checked_by="pod-1",
+        checked_at=datetime(2026, 8, 25),
+        created_at=datetime(2026, 8, 25, tzinfo=timezone.utc),
+        updated_at=datetime(2026, 8, 25, tzinfo=timezone.utc),
+    )
+    prisma = MagicMock()
+    prisma.get_all_latest_health_checks = AsyncMock(return_value=(row,))
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", prisma)
+
+    response = await latest_health_checks_endpoint(user_api_key_dict=UserAPIKeyAuth())
+
+    assert response == {
+        "latest_health_checks": {
+            "deployment-abc": {
+                "health_check_id": "hc-1",
+                "model_name": "gpt-4",
+                "model_id": "deployment-abc",
+                "status": "healthy",
+                "healthy_count": 1,
+                "unhealthy_count": 0,
+                "error_message": None,
+                "response_time_ms": 12.5,
+                "details": {"region": "eu"},
+                "checked_by": "pod-1",
+                "checked_at": "2026-08-25T00:00:00+00:00",
+                "created_at": "2026-08-25T00:00:00+00:00",
+            }
+        },
+        "total_models": 1,
+    }
 
 
 @pytest.mark.asyncio
@@ -628,12 +740,7 @@ def test_parse_background_health_check_model_groups_unset_returns_none():
 
     assert parse_background_health_check_model_groups(None) is None
     assert parse_background_health_check_model_groups({}) is None
-    assert (
-        parse_background_health_check_model_groups(
-            {"background_health_check_model_groups": None}
-        )
-        is None
-    )
+    assert parse_background_health_check_model_groups({"background_health_check_model_groups": None}) is None
 
 
 def test_parse_background_health_check_model_groups_list_returns_frozenset():
@@ -650,9 +757,7 @@ def test_parse_background_health_check_model_groups_malformed_raises(bad_value):
     from litellm.proxy.health_check import parse_background_health_check_model_groups
 
     with pytest.raises(ValueError, match="must be a list of model group names"):
-        parse_background_health_check_model_groups(
-            {"background_health_check_model_groups": bad_value}
-        )
+        parse_background_health_check_model_groups({"background_health_check_model_groups": bad_value})
 
 
 def test_filter_deployments_to_model_groups():
@@ -665,9 +770,7 @@ def test_filter_deployments_to_model_groups():
     ]
 
     assert filter_deployments_to_model_groups(model_list, None) == tuple(model_list)
-    assert filter_deployments_to_model_groups(
-        model_list, frozenset({"prod-openai"})
-    ) == (model_list[0], model_list[2])
+    assert filter_deployments_to_model_groups(model_list, frozenset({"prod-openai"})) == (model_list[0], model_list[2])
     assert filter_deployments_to_model_groups(model_list, frozenset()) == ()
 
 
diff --git a/tests/test_litellm/proxy/test_litellm_pre_call_utils.py b/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
index 892fa484ab4..94aaa32519e 100644
--- a/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
+++ b/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
@@ -35,6 +35,7 @@ from litellm.proxy.litellm_pre_call_utils import (
 )
 from litellm.litellm_core_utils.core_helpers import get_litellm_metadata_from_kwargs
 from litellm.litellm_core_utils.internal_call_metadata import MODEL_ACCESS_GROUP_METADATA_KEY
+from litellm.litellm_core_utils.redact_messages import _get_turn_off_message_logging_from_dynamic_params
 from litellm.litellm_core_utils.get_provider_specific_headers import (
     ProviderSpecificHeaderUtils,
 )
@@ -7678,6 +7679,107 @@ async def test_missing_session_id_omit_keeps_client_supplied_session_id():
     assert _spend_log_session_id(updated) == "client-session-1"
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "client_body",
+    [
+        {"model": "gpt-4o", "messages": [], "litellm_session_id": "cust-sess-1"},
+        {"model": "gpt-4o", "messages": [], "litellm_session_id": "cust-sess-1", "metadata": {"trace_id": "trace-1"}},
+    ],
+)
+async def test_missing_session_id_omit_keeps_body_litellm_session_id(
+    monkeypatch: pytest.MonkeyPatch, client_body: dict[str, object]
+):
+    from litellm.litellm_core_utils.get_litellm_params import get_litellm_params
+    from litellm.litellm_core_utils.litellm_logging import StandardLoggingPayloadSetup
+
+    monkeypatch.setattr(litellm, "request_correlation_in_logs", True)
+
+    updated = await add_litellm_data_to_request(
+        data=client_body,
+        request=_request_for("/v1/chat/completions"),
+        user_api_key_dict=UserAPIKeyAuth(api_key="hashed-key"),
+        proxy_config=MagicMock(),
+        general_settings={"missing_session_id": "omit"},
+    )
+
+    callback_session_id = StandardLoggingPayloadSetup.get_standard_logging_payload_session_id(
+        logging_obj=SimpleNamespace(litellm_session_id=""),
+        litellm_params=get_litellm_params(litellm_session_id="cust-sess-1", metadata=updated["metadata"]),
+    )
+    assert callback_session_id == "cust-sess-1"
+    assert updated["metadata"]["session_id"] == "cust-sess-1"
+    assert _spend_log_session_id(updated) == "cust-sess-1"
+
+
+@pytest.mark.asyncio
+async def test_missing_session_id_omit_body_litellm_session_id_does_not_override_metadata_session_id():
+    updated = await add_litellm_data_to_request(
+        data={
+            "model": "gpt-4o",
+            "messages": [],
+            "litellm_session_id": "cust-sess-1",
+            "metadata": {"session_id": "meta-sess-1"},
+        },
+        request=_request_for("/v1/chat/completions"),
+        user_api_key_dict=UserAPIKeyAuth(api_key="hashed-key"),
+        proxy_config=MagicMock(),
+        general_settings={"missing_session_id": "omit"},
+    )
+
+    assert updated["metadata"]["session_id"] == "meta-sess-1"
+    assert _spend_log_session_id(updated) == "meta-sess-1"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("path", ["/v1/responses", "/v1/messages"])
+async def test_missing_session_id_omit_keeps_metadata_session_id_on_litellm_metadata_routes(path: str):
+    updated = await add_litellm_data_to_request(
+        data={
+            "model": "gpt-4o",
+            "input": "hi",
+            "litellm_session_id": "cust-sess-1",
+            "metadata": {"session_id": "meta-sess-1"},
+        },
+        request=_request_for(path),
+        user_api_key_dict=UserAPIKeyAuth(api_key="hashed-key"),
+        proxy_config=MagicMock(),
+        general_settings={"missing_session_id": "omit"},
+    )
+
+    assert updated["litellm_metadata"]["session_id"] == "meta-sess-1"
+    assert _spend_log_session_id(updated, "litellm_metadata") == "meta-sess-1"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("path", ["/v1/responses", "/v1/messages"])
+async def test_missing_session_id_omit_keeps_body_litellm_session_id_on_litellm_metadata_routes(path: str):
+    updated = await add_litellm_data_to_request(
+        data={"model": "gpt-4o", "input": "hi", "litellm_session_id": "cust-sess-1"},
+        request=_request_for(path),
+        user_api_key_dict=UserAPIKeyAuth(api_key="hashed-key"),
+        proxy_config=MagicMock(),
+        general_settings={"missing_session_id": "omit"},
+    )
+
+    assert updated["litellm_metadata"]["session_id"] == "cust-sess-1"
+    assert _spend_log_session_id(updated, "litellm_metadata") == "cust-sess-1"
+
+
+@pytest.mark.asyncio
+async def test_missing_session_id_omit_ignores_empty_body_litellm_session_id():
+    updated = await add_litellm_data_to_request(
+        data={"model": "gpt-4o", "messages": [], "litellm_session_id": ""},
+        request=_request_for("/v1/chat/completions"),
+        user_api_key_dict=UserAPIKeyAuth(api_key="hashed-key"),
+        proxy_config=MagicMock(),
+        general_settings={"missing_session_id": "omit"},
+    )
+
+    assert "session_id" not in updated["metadata"]
+    assert _spend_log_session_id(updated) is None
+
+
 @pytest.mark.asyncio
 async def test_missing_session_id_generate_reuses_traceparent_trace_id():
     """A W3C traceparent already decides SpendLogs.session_id, so the callback session id must reuse it."""
@@ -7808,3 +7910,36 @@ async def test_client_supplied_omit_marker_never_reaches_the_spend_log(
         if general_settings.get("missing_session_id") == "generate"
         else "per-call-random-trace-id"
     )
+
+
+def test_default_team_settings_bool_turn_off_message_logging_redacts():
+    from litellm.proxy.proxy_server import ProxyConfig
+
+    pc = ProxyConfig()
+    pc.config = {
+        "litellm_settings": {
+            "default_team_settings": [
+                {
+                    "team_id": "team-redact",
+                    "success_callback": ["gcs_bucket"],
+                    "failure_callback": ["gcs_bucket"],
+                    "turn_off_message_logging": True,
+                }
+            ]
+        }
+    }
+
+    callback_metadata = LiteLLMProxyRequestSetup.add_team_based_callbacks_from_config(
+        team_id="team-redact",
+        proxy_config=pc,
+    )
+
+    assert callback_metadata is not None
+    assert callback_metadata.success_callback == ["gcs_bucket"]
+    assert callback_metadata.callback_vars == {"turn_off_message_logging": "True"}
+    assert (
+        _get_turn_off_message_logging_from_dynamic_params(
+            {"standard_callback_dynamic_params": dict(callback_metadata.callback_vars)}
+        )
+        is True
+    )
diff --git a/tests/test_litellm/proxy/test_pointfive_dashboard_config.py b/tests/test_litellm/proxy/test_pointfive_dashboard_config.py
new file mode 100644
index 00000000000..9e46e7f0b3e
--- /dev/null
+++ b/tests/test_litellm/proxy/test_pointfive_dashboard_config.py
@@ -0,0 +1,47 @@
+import json
+from pathlib import Path
+
+import litellm
+from litellm.integrations.custom_logger import CustomLogger
+
+
+def _dashboard_configs() -> tuple[dict, ...]:
+    path = Path(litellm.__file__).parent / "integrations" / "callback_configs.json"
+    return tuple(json.loads(path.read_text()))
+
+
+def _pointfive_config() -> dict:
+    return next(config for config in _dashboard_configs() if config["id"] == "pointfive")
+
+
+def test_pointfive_appears_in_the_dashboard_callback_dropdown():
+    """The dropdown is served from callback_configs.json, so an entry only in the dashboard source is invisible."""
+    entry = _pointfive_config()
+
+    assert entry["displayName"] == "PointFive"
+    assert entry["supports_key_team_logging"] is False
+    assert entry["dynamic_params"]["POINTFIVE_API_KEY"]["required"] is True
+    assert entry["dynamic_params"]["POINTFIVE_API_KEY"]["type"] == "password"
+    assert entry["dynamic_params"]["POINTFIVE_API_URL"]["required"] is False
+
+
+def test_the_dropdown_logo_asset_exists():
+    """A logo the dashboard cannot resolve degrades silently to a letter tile."""
+    logo = _pointfive_config()["logo"]
+    repo_root = Path(litellm.__file__).parent.parent
+    asset = repo_root / "ui" / "litellm-dashboard" / "public" / "assets" / "logos" / logo
+
+    assert logo == "pointfive.png"
+    assert asset.is_file()
+
+
+def test_the_dropdown_fields_are_the_env_vars_the_logger_reads():
+    """
+    The field names are the environment variables verbatim.
+
+    The proxy would uppercase them either way, but naming them as stored means the edit
+    form finds the saved values and prefills them instead of showing blanks.
+    """
+    fields = tuple(_pointfive_config()["dynamic_params"])
+
+    assert fields == tuple(CustomLogger.get_callback_env_vars("pointfive"))
diff --git a/tests/test_litellm/proxy/test_pointfive_ui_callback.py b/tests/test_litellm/proxy/test_pointfive_ui_callback.py
new file mode 100644
index 00000000000..13591d92005
--- /dev/null
+++ b/tests/test_litellm/proxy/test_pointfive_ui_callback.py
@@ -0,0 +1,15 @@
+from litellm.integrations.custom_logger import CustomLogger
+from litellm.proxy._types import AllCallbacks
+
+
+def test_pointfive_is_offered_in_the_ui_callback_registry():
+    """The proxy ui builds its form from this registry, so an absent entry is an absent form."""
+    entry = AllCallbacks().pointfive
+
+    assert entry.litellm_callback_name == "pointfive"
+    assert entry.ui_callback_name == "PointFive"
+
+
+def test_the_ui_offers_the_two_settings_the_plugin_reads():
+    """get_callback_env_vars is what the ui renders; it must match what the logger looks up."""
+    assert tuple(CustomLogger.get_callback_env_vars("pointfive")) == ("POINTFIVE_API_KEY", "POINTFIVE_API_URL")
diff --git a/tests/test_litellm/proxy/test_prisma_engine_watchdog.py b/tests/test_litellm/proxy/test_prisma_engine_watchdog.py
index d73f74c5cd2..ae750b0770a 100644
--- a/tests/test_litellm/proxy/test_prisma_engine_watchdog.py
+++ b/tests/test_litellm/proxy/test_prisma_engine_watchdog.py
@@ -18,12 +18,15 @@ import asyncio
 import os
 import threading
 import time
+from typing import Final
 from unittest.mock import ANY, AsyncMock, MagicMock, patch
 
 import pytest
 
 from litellm.proxy.utils import PrismaClient, ProxyLogging
 
+WRITER_PROBE_SQL: Final = "SELECT current_setting('transaction_read_only') AS transaction_read_only"
+
 
 @pytest.fixture(autouse=True)
 def mock_prisma_binary():
@@ -260,7 +263,7 @@ async def test_run_reconnect_cycle_uses_direct_path_when_engine_alive(
     """Direct reconnect (engine alive) probes the writer first and skips the
     recreate when the probe is healthy.
 
-    The engine-alive path now runs a SELECT 1 probe before recreating. A
+    The engine-alive path now runs a writability probe before recreating. A
     healthy probe means the connection is fine — e.g. an IAM token refresh
     already replaced the engine (issue #29176) — so recreating would kill a
     working engine. Recreate happens only when the probe fails (covered in
@@ -278,7 +281,7 @@ async def test_run_reconnect_cycle_uses_direct_path_when_engine_alive(
         await engine_client._run_reconnect_cycle(timeout_seconds=5.0)
 
     engine_client.db.recreate_prisma_client.assert_not_awaited()
-    engine_client.db.query_raw.assert_awaited_once_with("SELECT 1")
+    engine_client.db.query_raw.assert_awaited_once_with(WRITER_PROBE_SQL)
     engine_client.db.disconnect.assert_not_awaited()
     engine_client._start_engine_watcher.assert_awaited_once()
 
@@ -296,7 +299,7 @@ async def test_run_reconnect_cycle_uses_direct_path_when_pid_unknown(
         await engine_client._run_reconnect_cycle(timeout_seconds=5.0)
 
     engine_client.db.recreate_prisma_client.assert_not_awaited()
-    engine_client.db.query_raw.assert_awaited_once_with("SELECT 1")
+    engine_client.db.query_raw.assert_awaited_once_with(WRITER_PROBE_SQL)
     engine_client.db.disconnect.assert_not_awaited()
     engine_client._start_engine_watcher.assert_awaited_once()
 
diff --git a/tests/test_litellm/proxy/test_proxy_logging_hook_detection.py b/tests/test_litellm/proxy/test_proxy_logging_hook_detection.py
index 22930a26974..28ff4571b44 100644
--- a/tests/test_litellm/proxy/test_proxy_logging_hook_detection.py
+++ b/tests/test_litellm/proxy/test_proxy_logging_hook_detection.py
@@ -671,6 +671,95 @@ async def test_deferred_stream_guardrails_run_native_hook_when_opted_out(monkeyp
     assert routed.native_hooks_ran == []
 
 
+@pytest.mark.asyncio
+async def test_deferred_stream_guardrails_skip_pipeline_managed_native_hook(monkeypatch):
+    """A post_call pipeline step already ran the opted-out guardrail's own hook against
+    the buffered stream, so the deferred audit must not run it a second time."""
+    from litellm.proxy.common_request_processing import ProxyBaseLLMRequestProcessing
+    from litellm.types.proxy.policy_engine.pipeline_types import GuardrailPipeline, PipelineStep
+    from litellm.types.utils import Choices, Message, ModelResponse
+
+    pipeline_managed = _KeepsNativeHooks(event_hook=GuardrailEventHooks.post_call, default_on=True)
+    monkeypatch.setattr(litellm, "callbacks", [pipeline_managed])
+    pipeline = GuardrailPipeline(mode="post_call", steps=[PipelineStep(guardrail="keeps_native", on_fail="block")])
+
+    await ProxyBaseLLMRequestProcessing._run_deferred_stream_guardrails(
+        captured_data={
+            "messages": [{"role": "user", "content": "hi"}],
+            "metadata": {"_guardrail_pipelines": [("response-governance", pipeline)]},
+        },
+        captured_user_api_key_dict=UserAPIKeyAuth(api_key="sk-1234", request_route="/v1/chat/completions"),
+        captured_logging_obj=_streaming_logging_obj(),
+        assembled_response=ModelResponse(choices=[Choices(message=Message(role="assistant", content="hello"))]),
+        cache_hit=False,
+    )
+
+    assert pipeline_managed.native_hooks_ran == []
+
+
+@pytest.mark.asyncio
+async def test_deferred_stream_guardrails_run_native_hook_whose_pipeline_could_not_stream(monkeypatch):
+    """A pipeline step with neither streaming interface keeps the whole pipeline off the
+    stream, so the deferred audit is the only place the opted-out guardrail's own hook
+    still runs, the way it did before pipelines ran on streams."""
+    from litellm.proxy.common_request_processing import ProxyBaseLLMRequestProcessing
+    from litellm.types.proxy.policy_engine.pipeline_types import GuardrailPipeline, PipelineStep
+    from litellm.types.utils import Choices, Message, ModelResponse
+
+    class NeitherHookGuardrail(CustomGuardrail):
+        pass
+
+    pipeline_managed = _KeepsNativeHooks(event_hook=GuardrailEventHooks.post_call, default_on=True)
+    neither = NeitherHookGuardrail(guardrail_name="gr-neither", event_hook=GuardrailEventHooks.post_call)
+    monkeypatch.setattr(litellm, "callbacks", [pipeline_managed, neither])
+    pipeline = GuardrailPipeline(
+        mode="post_call",
+        steps=[
+            PipelineStep(guardrail="keeps_native", on_fail="next"),
+            PipelineStep(guardrail="gr-neither", on_fail="block"),
+        ],
+    )
+
+    await ProxyBaseLLMRequestProcessing._run_deferred_stream_guardrails(
+        captured_data={
+            "messages": [{"role": "user", "content": "hi"}],
+            "metadata": {"_guardrail_pipelines": [("response-governance", pipeline)]},
+        },
+        captured_user_api_key_dict=UserAPIKeyAuth(api_key="sk-1234", request_route="/v1/chat/completions"),
+        captured_logging_obj=_streaming_logging_obj(),
+        assembled_response=ModelResponse(choices=[Choices(message=Message(role="assistant", content="hello"))]),
+        cache_hit=False,
+    )
+
+    assert pipeline_managed.native_hooks_ran == ["post_call"]
+
+
+@pytest.mark.asyncio
+async def test_deferred_stream_guardrails_run_native_hook_on_route_without_translation(monkeypatch):
+    """A route with no endpoint guardrail translation cannot gate the stream through its
+    pipelines, so the deferred audit still owes the opted-out guardrail its own hook."""
+    from litellm.proxy.common_request_processing import ProxyBaseLLMRequestProcessing
+    from litellm.types.proxy.policy_engine.pipeline_types import GuardrailPipeline, PipelineStep
+    from litellm.types.utils import Choices, Message, ModelResponse
+
+    pipeline_managed = _KeepsNativeHooks(event_hook=GuardrailEventHooks.post_call, default_on=True)
+    monkeypatch.setattr(litellm, "callbacks", [pipeline_managed])
+    pipeline = GuardrailPipeline(mode="post_call", steps=[PipelineStep(guardrail="keeps_native", on_fail="block")])
+
+    await ProxyBaseLLMRequestProcessing._run_deferred_stream_guardrails(
+        captured_data={
+            "messages": [{"role": "user", "content": "hi"}],
+            "metadata": {"_guardrail_pipelines": [("response-governance", pipeline)]},
+        },
+        captured_user_api_key_dict=UserAPIKeyAuth(api_key="sk-1234", request_route="/custom/stream"),
+        captured_logging_obj=_streaming_logging_obj(),
+        assembled_response=ModelResponse(choices=[Choices(message=Message(role="assistant", content="hello"))]),
+        cache_hit=False,
+    )
+
+    assert pipeline_managed.native_hooks_ran == ["post_call"]
+
+
 @pytest.mark.asyncio
 async def test_realtime_guardrails_skip_opted_out_guardrail(monkeypatch):
     """The realtime path calls apply_guardrail directly, so the opt-out has to be
diff --git a/tests/test_litellm/proxy/test_proxy_server.py b/tests/test_litellm/proxy/test_proxy_server.py
index 54579e6cb7c..e058a4f6396 100644
--- a/tests/test_litellm/proxy/test_proxy_server.py
+++ b/tests/test_litellm/proxy/test_proxy_server.py
@@ -6,6 +6,7 @@ import os
 import re
 import socket
 import subprocess
+import time
 import types
 from datetime import datetime, timedelta, timezone
 from pathlib import Path
@@ -28,7 +29,7 @@ from litellm.caching.caching import RedisCache
 from litellm.caching.redis_cluster_cache import RedisClusterCache
 from litellm.litellm_core_utils.get_model_cost_map import ModelCostMapReloaded
 from litellm.caching.dual_cache import DualCache
-from litellm.proxy._types import LitellmUserRoles, UserAPIKeyAuth
+from litellm.proxy._types import LitellmUserRoles, TokenCountRequest, UserAPIKeyAuth
 from litellm.proxy.auth.user_api_key_auth import user_api_key_auth
 from litellm.proxy.proxy_server import app, initialize
 from litellm.utils import _invalidate_model_cost_lowercase_map
@@ -7749,7 +7750,7 @@ async def test_increment_spend_counters_team_and_member():
 
 
 @pytest.mark.asyncio
-async def test_init_and_increment_spend_counter_reseeds_from_db_on_counter_miss():
+async def test_prepare_spend_counter_increment_reseeds_from_db_on_counter_miss():
     """When the Redis counter is missing, the reseed path reads the
     authoritative spend from the DB (not a stale cache), so the next
     increment continues from the correct base value."""
@@ -7762,8 +7763,17 @@ async def test_init_and_increment_spend_counter_reseeds_from_db_on_counter_miss(
         recorded_increments.append({"key": key, "value": value, "ttl": ttl})
         return value
 
+    async def record_pipeline(increment_list, **kwargs):
+        results = []
+        for op in increment_list:
+            await record_increment(key=op["key"], value=op["increment_value"], ttl=op["ttl"])
+            results.append(op["increment_value"])
+        return results
+
     fake_redis = AsyncMock()
     fake_redis.async_increment = AsyncMock(side_effect=record_increment)
+    fake_redis.async_increment_pipeline = AsyncMock(side_effect=record_pipeline)
+    fake_redis.get_ttl = MagicMock(return_value=None)
     fake_redis.async_get_cache = AsyncMock(return_value=None)  # counter missing
     fake_redis.async_set_cache = AsyncMock(return_value=True)  # SET NX wins
     counter_cache.redis_cache = fake_redis
@@ -7782,7 +7792,10 @@ async def test_init_and_increment_spend_counter_reseeds_from_db_on_counter_miss(
     stale_cache.in_memory_cache.set_cache(key="team_id:team-9", value=stale_team)
 
     import litellm.proxy.proxy_server as ps
-    from litellm.proxy.proxy_server import _init_and_increment_spend_counter
+    from litellm.proxy.proxy_server import (
+        _apply_spend_counter_increments,
+        _prepare_spend_counter_increment,
+    )
 
     orig_user, orig_counter, orig_prisma = (
         ps.user_api_key_cache,
@@ -7793,11 +7806,12 @@ async def test_init_and_increment_spend_counter_reseeds_from_db_on_counter_miss(
     ps.spend_counter_cache = counter_cache
     ps.prisma_client = fake_prisma
     try:
-        await _init_and_increment_spend_counter(
+        pending = await _prepare_spend_counter_increment(
             counter_key="spend:team:team-9",
             source_cache_key="team_id:team-9",
             increment=1.5,
         )
+        await _apply_spend_counter_increments(pending=(pending,))
 
         fake_prisma.db.litellm_teamtable.find_unique.assert_awaited_once_with(where={"team_id": "team-9"})
         # Seed uses SET NX with db_spend (42) — cross-pod safe, no INCR of 42.
@@ -7976,7 +7990,10 @@ async def test_reseed_spend_from_db_skips_window_variant_keys():
 @pytest.mark.asyncio
 async def test_window_spend_counter_reseeds_from_spend_logs_on_counter_miss():
     from litellm.caching.dual_cache import DualCache
-    from litellm.proxy.proxy_server import _init_and_increment_window_spend_counter
+    from litellm.proxy.proxy_server import (
+        _apply_spend_counter_increments,
+        _prepare_window_spend_counter_increment,
+    )
 
     counter_cache = DualCache()
     window_start = datetime.now(timezone.utc) - timedelta(hours=1)
@@ -7992,7 +8009,7 @@ async def test_window_spend_counter_reseeds_from_spend_logs_on_counter_miss():
     ps.spend_counter_cache = counter_cache
     ps.prisma_client = fake_prisma
     try:
-        await _init_and_increment_window_spend_counter(
+        pending = await _prepare_window_spend_counter_increment(
             counter_key="spend:key:key-window:window:1h",
             entity_type="Key",
             entity_id="key-window",
@@ -8000,6 +8017,7 @@ async def test_window_spend_counter_reseeds_from_spend_logs_on_counter_miss():
             window_start=window_start,
             increment=0.5,
         )
+        await _apply_spend_counter_increments(pending=(pending,) if pending is not None else ())
 
         fake_prisma.db.litellm_spendlogs.group_by.assert_awaited_once_with(
             by=["api_key"],
@@ -8015,7 +8033,10 @@ async def test_window_spend_counter_reseeds_from_spend_logs_on_counter_miss():
 @pytest.mark.asyncio
 async def test_init_spend_counter_redis_clean_miss_skips_stale_in_memory():
     from litellm.caching.dual_cache import DualCache
-    from litellm.proxy.proxy_server import _init_and_increment_spend_counter
+    from litellm.proxy.proxy_server import (
+        _apply_spend_counter_increments,
+        _prepare_spend_counter_increment,
+    )
 
     counter_cache = DualCache()
     counter_key = "spend:team:team-stale-local"
@@ -8037,6 +8058,15 @@ async def test_init_spend_counter_redis_clean_miss_skips_stale_in_memory():
     fake_redis.async_get_cache = AsyncMock(return_value=None)
     fake_redis.async_increment = AsyncMock(side_effect=redis_increment)
     fake_redis.async_set_cache = AsyncMock(side_effect=redis_set_cache)
+
+    async def redis_increment_pipeline(increment_list, **_):
+        results = []
+        for op in increment_list:
+            results.append(await redis_increment(key=op["key"], value=op["increment_value"]))
+        return results
+
+    fake_redis.async_increment_pipeline = AsyncMock(side_effect=redis_increment_pipeline)
+    fake_redis.get_ttl = MagicMock(return_value=None)
     counter_cache.redis_cache = fake_redis
 
     db_row = MagicMock()
@@ -8055,11 +8085,12 @@ async def test_init_spend_counter_redis_clean_miss_skips_stale_in_memory():
     ps.prisma_client = fake_prisma
     ps.user_api_key_cache = DualCache()
     try:
-        await _init_and_increment_spend_counter(
+        pending = await _prepare_spend_counter_increment(
             counter_key=counter_key,
             source_cache_key="team_id:team-stale-local",
             increment=1.5,
         )
+        await _apply_spend_counter_increments(pending=(pending,))
 
         fake_prisma.db.litellm_teamtable.find_unique.assert_awaited_once_with(where={"team_id": "team-stale-local"})
         # Seed via SET NX (42) + delta via INCRBYFLOAT (1.5) = 43.5.
@@ -8074,7 +8105,10 @@ async def test_init_spend_counter_redis_clean_miss_skips_stale_in_memory():
 @pytest.mark.asyncio
 async def test_window_spend_counter_redis_clean_miss_skips_stale_in_memory():
     from litellm.caching.dual_cache import DualCache
-    from litellm.proxy.proxy_server import _init_and_increment_window_spend_counter
+    from litellm.proxy.proxy_server import (
+        _apply_spend_counter_increments,
+        _prepare_window_spend_counter_increment,
+    )
 
     counter_cache = DualCache()
     counter_key = "spend:key:key-window-stale-local:window:1h"
@@ -8097,6 +8131,15 @@ async def test_window_spend_counter_redis_clean_miss_skips_stale_in_memory():
     fake_redis.async_get_cache = AsyncMock(return_value=None)
     fake_redis.async_set_cache = AsyncMock(side_effect=redis_set_cache)
     fake_redis.async_increment = AsyncMock(side_effect=redis_increment)
+
+    async def redis_increment_pipeline(increment_list, **_):
+        results = []
+        for op in increment_list:
+            results.append(await redis_increment(key=op["key"], value=op["increment_value"]))
+        return results
+
+    fake_redis.async_increment_pipeline = AsyncMock(side_effect=redis_increment_pipeline)
+    fake_redis.get_ttl = MagicMock(return_value=None)
     counter_cache.redis_cache = fake_redis
 
     fake_prisma = MagicMock()
@@ -8111,7 +8154,7 @@ async def test_window_spend_counter_redis_clean_miss_skips_stale_in_memory():
     ps.spend_counter_cache = counter_cache
     ps.prisma_client = fake_prisma
     try:
-        await _init_and_increment_window_spend_counter(
+        pending = await _prepare_window_spend_counter_increment(
             counter_key=counter_key,
             entity_type="Key",
             entity_id="key-window-stale-local",
@@ -8119,6 +8162,7 @@ async def test_window_spend_counter_redis_clean_miss_skips_stale_in_memory():
             window_start=window_start,
             increment=0.5,
         )
+        await _apply_spend_counter_increments(pending=(pending,) if pending is not None else ())
 
         fake_prisma.db.litellm_spendlogs.group_by.assert_awaited_once_with(
             by=["api_key"],
@@ -8138,7 +8182,10 @@ async def test_window_spend_counter_redis_clean_miss_skips_stale_in_memory():
 @pytest.mark.asyncio
 async def test_window_spend_counter_redis_concurrent_seed_does_not_double_seed():
     from litellm.caching.dual_cache import DualCache
-    from litellm.proxy.proxy_server import _init_and_increment_window_spend_counter
+    from litellm.proxy.proxy_server import (
+        _apply_spend_counter_increments,
+        _prepare_window_spend_counter_increment,
+    )
 
     counter_cache = DualCache()
     counter_key = "spend:key:key-window-concurrent-seed:window:1h"
@@ -8161,6 +8208,15 @@ async def test_window_spend_counter_redis_concurrent_seed_does_not_double_seed()
     fake_redis.async_get_cache = AsyncMock(side_effect=redis_get_cache)
     fake_redis.async_set_cache = AsyncMock(return_value=False)
     fake_redis.async_increment = AsyncMock(side_effect=redis_increment)
+
+    async def redis_increment_pipeline(increment_list, **_):
+        results = []
+        for op in increment_list:
+            results.append(await redis_increment(key=op["key"], value=op["increment_value"]))
+        return results
+
+    fake_redis.async_increment_pipeline = AsyncMock(side_effect=redis_increment_pipeline)
+    fake_redis.get_ttl = MagicMock(return_value=None)
     counter_cache.redis_cache = fake_redis
 
     fake_prisma = MagicMock()
@@ -8175,7 +8231,7 @@ async def test_window_spend_counter_redis_concurrent_seed_does_not_double_seed()
     ps.spend_counter_cache = counter_cache
     ps.prisma_client = fake_prisma
     try:
-        await _init_and_increment_window_spend_counter(
+        pending = await _prepare_window_spend_counter_increment(
             counter_key=counter_key,
             entity_type="Key",
             entity_id="key-window-concurrent-seed",
@@ -8183,6 +8239,7 @@ async def test_window_spend_counter_redis_concurrent_seed_does_not_double_seed()
             window_start=window_start,
             increment=0.5,
         )
+        await _apply_spend_counter_increments(pending=(pending,) if pending is not None else ())
 
         fake_redis.async_set_cache.assert_awaited_once_with(
             key=counter_key,
@@ -8199,7 +8256,7 @@ async def test_window_spend_counter_redis_concurrent_seed_does_not_double_seed()
 @pytest.mark.asyncio
 async def test_window_spend_counter_skips_invalid_window_start():
     from litellm.caching.dual_cache import DualCache
-    from litellm.proxy.proxy_server import _init_and_increment_window_spend_counter
+    from litellm.proxy.proxy_server import _prepare_window_spend_counter_increment
 
     counter_cache = DualCache()
 
@@ -8208,7 +8265,7 @@ async def test_window_spend_counter_skips_invalid_window_start():
     orig_counter = ps.spend_counter_cache
     ps.spend_counter_cache = counter_cache
     try:
-        await _init_and_increment_window_spend_counter(
+        pending = await _prepare_window_spend_counter_increment(
             counter_key="spend:key:key-invalid-window:window:not-a-duration",
             entity_type="Key",
             entity_id="key-invalid-window",
@@ -8216,6 +8273,7 @@ async def test_window_spend_counter_skips_invalid_window_start():
             window_start=None,
             increment=0.5,
         )
+        assert pending is None
 
         assert counter_cache.in_memory_cache.get_cache(key="spend:key:key-invalid-window:window:not-a-duration") is None
     finally:
@@ -8279,6 +8337,9 @@ async def test_increment_spend_counters_finalizes_after_unreserved_increments():
     async def assert_reservation_not_finalized_yet(**kwargs):
         assert budget_reservation["finalized"] is False
         incremented_counters.append(kwargs["counter_key"])
+        return ps._PendingSpendIncrement(
+            counter_key=kwargs["counter_key"], increment=kwargs["increment"]
+        )
 
     import litellm.proxy.proxy_server as ps
 
@@ -8287,7 +8348,7 @@ async def test_increment_spend_counters_finalizes_after_unreserved_increments():
     ps.user_api_key_cache = DualCache()
     try:
         with patch(
-            "litellm.proxy.proxy_server._init_and_increment_spend_counter",
+            "litellm.proxy.proxy_server._prepare_spend_counter_increment",
             new=AsyncMock(side_effect=assert_reservation_not_finalized_yet),
         ):
             await increment_spend_counters(
@@ -8620,7 +8681,7 @@ async def test_get_current_spend_uses_db_zero_over_stale_fallback():
 async def test_concurrent_read_and_write_paths_share_one_db_query():
     """
     The read path (`get_current_spend`) and the write path
-    (`_init_and_increment_spend_counter`) both reseed cold counters from
+    (`_prepare_spend_counter_increment`) both reseed cold counters from
     the DB. They must share the per-counter lock so a concurrent pre-call
     enforcement read and post-call increment for the same counter collapse
     to one DB query, not two.
@@ -8629,7 +8690,7 @@ async def test_concurrent_read_and_write_paths_share_one_db_query():
 
     from litellm.caching.dual_cache import DualCache
     from litellm.proxy.proxy_server import (
-        _init_and_increment_spend_counter,
+        _prepare_spend_counter_increment,
         get_current_spend,
     )
 
@@ -8683,7 +8744,7 @@ async def test_concurrent_read_and_write_paths_share_one_db_query():
     try:
         results = await _asyncio.gather(
             get_current_spend(counter_key=counter_key, fallback_spend=0.0),
-            _init_and_increment_spend_counter(
+            _prepare_spend_counter_increment(
                 counter_key=counter_key,
                 source_cache_key="ignored",
                 increment=1.5,
@@ -12894,3 +12955,59 @@ async def test_update_general_settings_keeps_yaml_openai_websocket_passthrough()
         import litellm.proxy.proxy_server as ps
 
         assert ps.general_settings["enable_openai_websocket_passthrough"] is False
+
+
+async def test_token_counter_keeps_the_event_loop_free_during_a_huggingface_count(monkeypatch):
+    from tests.large_text import text
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+        assert_loop_stayed_free,
+        timed_with_loop_lags,
+        warm_tokenizer,
+    )
+
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None)
+    warm_tokenizer("claude-fable-5")
+
+    response, took, lags = await timed_with_loop_lags(
+        lambda: proxy_server_module.token_counter(TokenCountRequest(model="claude-fable-5", prompt=text * 100))
+    )
+
+    assert response.total_tokens > 0
+    assert_loop_stayed_free(took, lags)
+
+
+async def test_token_counter_loads_a_custom_tokenizer_off_the_event_loop(monkeypatch):
+    from tokenizers import Tokenizer
+
+    from litellm import Router
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import assert_loop_stayed_free, timed_with_loop_lags
+
+    claude_tokenizer: Final = litellm.utils._select_tokenizer("claude-fable-5")["tokenizer"]
+
+    class SlowHubTokenizer:
+        @staticmethod
+        def from_pretrained(identifier: str, revision: str = "main", token: str | None = None) -> Tokenizer:
+            time.sleep(0.3)
+            return claude_tokenizer
+
+    monkeypatch.setattr(litellm.utils, "Tokenizer", SlowHubTokenizer)
+    monkeypatch.setattr(
+        "litellm.proxy.proxy_server.llm_router",
+        Router(
+            model_list=[
+                {
+                    "model_name": "self-hosted",
+                    "litellm_params": {"model": "openai/self-hosted-model", "api_base": "http://localhost:8080/v1"},
+                    "model_info": {"custom_tokenizer": {"identifier": "my-org/tokenizer", "revision": "main", "auth_token": None}},
+                }
+            ]
+        ),
+    )
+
+    response, took, lags = await timed_with_loop_lags(
+        lambda: proxy_server_module.token_counter(TokenCountRequest(model="self-hosted", prompt="count me off the loop"))
+    )
+
+    assert response.tokenizer_type == "huggingface_tokenizer"
+    assert response.total_tokens > 0
+    assert_loop_stayed_free(took, lags)
diff --git a/tests/test_litellm/proxy/test_proxy_utils.py b/tests/test_litellm/proxy/test_proxy_utils.py
index 9462f2c8eb0..646596c5b88 100644
--- a/tests/test_litellm/proxy/test_proxy_utils.py
+++ b/tests/test_litellm/proxy/test_proxy_utils.py
@@ -1,5 +1,6 @@
 import datetime as real_datetime
 import smtplib
+from typing import Final
 
 import pytest
 from fastapi import HTTPException
@@ -8,7 +9,7 @@ from litellm.caching.caching import DualCache
 from litellm.integrations.custom_guardrail import CustomGuardrail
 from litellm.integrations.custom_logger import CustomLogger
 from litellm.proxy._types import ProxyErrorTypes, UserAPIKeyAuth
-from litellm.proxy.utils import ProxyLogging
+from litellm.proxy.utils import PrismaClient, ProxyLogging
 from litellm.types.guardrails import GuardrailEventHooks
 
 
@@ -887,6 +888,7 @@ from typing import cast
 
 import litellm
 from litellm.proxy.utils import create_model_info_response
+from litellm.types.router import DeploymentModelListingInfo
 from litellm.types.utils import ModelInfo
 
 
@@ -914,7 +916,7 @@ def test_create_model_info_response_includes_max_tokens_from_lookup():
 
 def test_create_model_info_response_does_not_call_router_group_info():
     router = MagicMock()
-    router.get_configured_token_limits.return_value = (None, None)
+    router.get_model_listing_info.return_value = None
 
     response = create_model_info_response(
         model_id="some-model",
@@ -929,7 +931,9 @@ def test_create_model_info_response_does_not_call_router_group_info():
 
 def test_create_model_info_response_uses_deployment_limits_when_not_in_cost_map():
     router = MagicMock()
-    router.get_configured_token_limits.return_value = (32000, 8000)
+    router.get_model_listing_info.return_value = DeploymentModelListingInfo(
+        cost_map_keys=("my-custom-deployment",), max_input_tokens=32000, max_output_tokens=8000
+    )
 
     response = create_model_info_response(
         model_id="my-custom-deployment",
@@ -986,7 +990,9 @@ def test_create_model_info_response_uses_deployment_mode_for_auto_router():
 
 def test_create_model_info_response_deployment_limits_override_cost_map():
     router = MagicMock()
-    router.get_configured_token_limits.return_value = (200000, None)
+    router.get_model_listing_info.return_value = DeploymentModelListingInfo(
+        cost_map_keys=("gpt-4o",), max_input_tokens=200000, max_output_tokens=None
+    )
 
     response = create_model_info_response(
         model_id="gpt-4o",
@@ -999,6 +1005,54 @@ def test_create_model_info_response_deployment_limits_override_cost_map():
     assert response["max_output_tokens"] == 16384
 
 
+def test_create_model_info_response_reports_widest_window_in_a_mixed_group():
+    """A group mixing models advertises the widest window, not whichever is listed first."""
+    limits = {
+        "small-model": _fake_model_info(max_input_tokens=200000, max_output_tokens=4096, mode="chat"),
+        "large-model": _fake_model_info(max_input_tokens=1000000, max_output_tokens=128000, mode="chat"),
+    }
+
+    for keys in (("small-model", "large-model"), ("large-model", "small-model")):
+        router = MagicMock()
+        router.get_model_listing_info.return_value = DeploymentModelListingInfo(
+            cost_map_keys=keys, max_input_tokens=None, max_output_tokens=None
+        )
+
+        response = create_model_info_response(
+            model_id="house-claude",
+            provider="openai",
+            llm_router=router,
+            get_model_info=lambda model: limits[model],
+        )
+
+        assert response["max_input_tokens"] == 1000000, keys
+        assert response["max_output_tokens"] == 128000, keys
+
+
+def test_create_model_info_response_resolves_alias_once_per_listing():
+    """The alias is the same for every deployment in the group, so it is looked up once."""
+    seen: list[str] = []
+
+    def _tracking_get_model_info(model: str) -> ModelInfo:
+        seen.append(model)
+        return _fake_model_info(max_input_tokens=128000)
+
+    router = MagicMock()
+    router.get_model_listing_info.return_value = DeploymentModelListingInfo(
+        cost_map_keys=("model-a", "model-b"), max_input_tokens=None, max_output_tokens=None
+    )
+
+    create_model_info_response(
+        model_id="house-model",
+        provider="openai",
+        llm_router=router,
+        get_model_info=_tracking_get_model_info,
+    )
+
+    assert seen.count("house-model") == 1
+    assert sorted(seen) == ["house-model", "model-a", "model-b"]
+
+
 def test_create_model_info_response_survives_malformed_configured_limits():
     from litellm import Router
 
@@ -1823,6 +1877,44 @@ def test_a_dispatched_failure_lifts_the_four_fields_the_spend_log_needs():
     assert lifted["standard_logging_object"] == {"id": "log-1"}
 
 
+@pytest.mark.asyncio
+async def test_a_dispatched_failure_is_counted_off_the_event_loop():
+    from unittest.mock import AsyncMock, patch
+
+    from tests.large_text import text
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+        assert_loop_stayed_free,
+        timed_with_loop_lags,
+        warm_tokenizer,
+    )
+
+    warm_tokenizer("claude-fable-5")
+    request_data = {
+        "litellm_logging_obj": _LoggingObj(
+            {
+                "first_api_call_start_time": 1700000000.0,
+                "call_type": "acompletion",
+                "model": "claude-fable-5",
+                "messages": [{"role": "user", "content": text * 100}],
+            }
+        ),
+        "metadata": {},
+    }
+    proxy_logging_obj = ProxyLogging(user_api_key_cache=DualCache())
+    proxy_logging_obj.alert_types = []
+    with patch.object(proxy_logging_obj, "update_request_status", new=AsyncMock()):
+        _, took, lags = await timed_with_loop_lags(
+            lambda: proxy_logging_obj.post_call_failure_hook(
+                request_data=request_data,
+                original_exception=Exception("boom"),
+                user_api_key_dict=UserAPIKeyAuth(),
+            )
+        )
+
+    assert request_data["combined_usage_object"].prompt_tokens > 0
+    assert_loop_stayed_free(took, lags)
+
+
 @pytest.mark.asyncio
 async def test_proxy_only_error_expected_4xx_skips_traceback_for_both_handlers(monkeypatch):
     """Regression for LIT-6043: an expected 4xx must not format a traceback for
@@ -1922,6 +2014,122 @@ async def test_proxy_only_error_5xx_keeps_traceback_and_runs_sync_callbacks(monk
     assert "test_proxy_utils" in captured["async_traceback"]
 
 
+def test_create_model_info_response_resolves_alias_to_deployment_model():
+    """A public model name that is not itself a cost-map key must not be resolved through
+    the fallback-generalization rules: `bedrock-claude-opus-5` matches the generic
+    claude-family baseline (200k/64k) by substring, while the deployment it fronts really
+    accepts 1M/128k. Regression for the /v1/models alias resolution introduced in v1.94.0."""
+    from litellm import Router
+
+    saved_model_cost = dict(litellm.model_cost)
+    try:
+        router = Router(
+            model_list=[
+                {
+                    "model_name": "bedrock-claude-opus-5",
+                    "litellm_params": {
+                        "custom_llm_provider": "bedrock",
+                        "model": "bedrock/eu.anthropic.claude-opus-5",
+                    },
+                    "model_info": {"base_model": "eu.anthropic.claude-opus-5"},
+                }
+            ]
+        )
+
+        response = create_model_info_response(
+            model_id="bedrock-claude-opus-5", provider="openai", llm_router=router
+        )
+    finally:
+        litellm.model_cost.clear()
+        litellm.model_cost.update(saved_model_cost)
+
+    assert response["max_input_tokens"] == 1000000
+    assert response["max_output_tokens"] == 128000
+
+
+def test_create_model_info_response_keeps_exact_alias_over_generalized_deployment_model():
+    """Mirror of the alias bug: when the deployment points at a custom backend name that
+    only matches a generalization rule, the listed name's exact cost-map entry is the
+    better answer and must win."""
+    from litellm import Router
+
+    saved_model_cost = dict(litellm.model_cost)
+    try:
+        router = Router(
+            model_list=[
+                {
+                    "model_name": "claude-opus-5",
+                    "litellm_params": {
+                        "custom_llm_provider": "bedrock",
+                        "model": "bedrock/my-claude-opus-5-provisioned",
+                    },
+                }
+            ]
+        )
+
+        response = create_model_info_response(
+            model_id="claude-opus-5", provider="openai", llm_router=router
+        )
+    finally:
+        litellm.model_cost.clear()
+        litellm.model_cost.update(saved_model_cost)
+
+    assert response["max_input_tokens"] == 1000000
+
+
+def test_create_model_info_response_falls_back_to_alias_for_opaque_deployment_name():
+    """An Azure deployment named after the resource rather than the model has no cost-map
+    entry; the listed name still does, and must keep answering."""
+    from litellm import Router
+
+    saved_model_cost = dict(litellm.model_cost)
+    try:
+        router = Router(
+            model_list=[
+                {
+                    "model_name": "gpt-4o",
+                    "litellm_params": {"model": "azure/my-gpt4o-deployment"},
+                }
+            ]
+        )
+
+        response = create_model_info_response(
+            model_id="gpt-4o", provider="openai", llm_router=router
+        )
+    finally:
+        litellm.model_cost.clear()
+        litellm.model_cost.update(saved_model_cost)
+
+    assert response["max_input_tokens"] == 128000
+    assert response["max_output_tokens"] == 16384
+
+
+def test_create_model_info_response_resolves_mode_through_deployment_model():
+    """`mode` is derived from the same lookup, so an aliased embedding deployment
+    currently reports no mode at all; it must report `embedding`."""
+    from litellm import Router
+
+    saved_model_cost = dict(litellm.model_cost)
+    try:
+        router = Router(
+            model_list=[
+                {
+                    "model_name": "my-embeddings",
+                    "litellm_params": {"model": "openai/text-embedding-3-small"},
+                }
+            ]
+        )
+
+        response = create_model_info_response(
+            model_id="my-embeddings", provider="openai", llm_router=router
+        )
+    finally:
+        litellm.model_cost.clear()
+        litellm.model_cost.update(saved_model_cost)
+
+    assert response["mode"] == "embedding"
+
+
 @pytest.mark.parametrize(
     "key_metadata, team_metadata, expected_to_run",
     [
@@ -2000,3 +2208,49 @@ async def test_post_call_failure_hook_redacts_traceback_before_callbacks(monkeyp
     assert recorder.received_traceback is not None
     assert provider_key not in recorder.received_traceback
     assert "REDACTED" in recorder.received_traceback
+
+
+class TestPrismaClientTokenAuthBehindThePool:
+    """Behind the in-container pool the supervisor renews the writer's database
+    token and hands the workers a loopback URL with a static password, so the
+    writer wrapper must not run its own refresh loop. The reader is not pooled
+    and keeps refreshing its own token."""
+
+    UPSTREAM: Final = "postgresql://litellm:TOKEN@db.internal:5432/litellm"
+    READER: Final = "postgresql://litellm:TOKEN@reader.internal:5432/litellm"
+
+    def _client(self, monkeypatch: pytest.MonkeyPatch, pooled: bool) -> PrismaClient:
+        from litellm.proxy.db.pgbouncer import PGBOUNCER_POOLED_ENV_VAR
+
+        monkeypatch.delenv("AZURE_POSTGRESQL_AUTH", raising=False)
+        monkeypatch.setenv("IAM_TOKEN_DB_AUTH", "true")
+        monkeypatch.setenv("AWS_REGION_NAME", "us-east-1")
+        monkeypatch.setenv("DATABASE_URL", self.UPSTREAM)
+        monkeypatch.setenv("DATABASE_URL_READ_REPLICA", self.READER)
+        if pooled:
+            monkeypatch.setenv(PGBOUNCER_POOLED_ENV_VAR, "true")
+        else:
+            monkeypatch.delenv(PGBOUNCER_POOLED_ENV_VAR, raising=False)
+        rds: Final = MagicMock()
+        rds.generate_db_auth_token.return_value = "TOKEN"
+        with patch("boto3.client", return_value=rds):
+            return PrismaClient(database_url=self.UPSTREAM, proxy_logging_obj=MagicMock(spec=ProxyLogging))
+
+    def test_a_pooled_writer_leaves_token_refresh_to_the_pooler_while_the_reader_keeps_its_own(
+        self, monkeypatch: pytest.MonkeyPatch
+    ):
+        from litellm.proxy.db.routing_prisma_wrapper import RoutingPrismaWrapper
+
+        client = self._client(monkeypatch, pooled=True)
+        assert isinstance(client.db, RoutingPrismaWrapper)
+        assert client.db.writer.iam_token_db_auth is False
+        assert client.db.reader.iam_token_db_auth is True
+        assert client.token_auth is not None
+
+    def test_an_unpooled_writer_still_refreshes_its_own_token(self, monkeypatch: pytest.MonkeyPatch):
+        from litellm.proxy.db.routing_prisma_wrapper import RoutingPrismaWrapper
+
+        client = self._client(monkeypatch, pooled=False)
+        assert isinstance(client.db, RoutingPrismaWrapper)
+        assert client.db.writer.iam_token_db_auth is True
+        assert client.db.reader.iam_token_db_auth is True
diff --git a/tests/test_litellm/proxy/utils/helpers/test_error_helpers.py b/tests/test_litellm/proxy/utils/helpers/test_error_helpers.py
index dc30798df55..117c5aa3081 100644
--- a/tests/test_litellm/proxy/utils/helpers/test_error_helpers.py
+++ b/tests/test_litellm/proxy/utils/helpers/test_error_helpers.py
@@ -1,7 +1,10 @@
+import asyncio
 import json
+from unittest.mock import AsyncMock, MagicMock
 
 import pytest
 from fastapi import HTTPException
+from prisma.errors import DataError
 
 from litellm.proxy._types import ProxyErrorTypes, ProxyException
 from litellm.proxy.utils import get_error_message_str, handle_exception_on_proxy
@@ -171,3 +174,45 @@ def test_handle_exception_on_proxy_error_path_none_input_wraps_as_500():
         "code": "500",
         "type": ProxyErrorTypes.internal_server_error.value,
     }
+
+
+@pytest.mark.asyncio
+async def test_handle_exception_on_proxy_read_only_transaction_forces_writer_recreate(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    prisma_client = MagicMock()
+    prisma_client.recreate_read_only_writer = AsyncMock(return_value=True)
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", prisma_client)
+    exc = DataError(
+        data={
+            "user_facing_error": {
+                "message": 'PostgresError { code: "25006", message: "cannot execute UPDATE in a read-only transaction" }'
+            }
+        }
+    )
+
+    result = handle_exception_on_proxy(exc)
+    await asyncio.sleep(0)
+
+    snapshot = {
+        "code": result.code,
+        "recreate_kwargs": prisma_client.recreate_read_only_writer.await_args.kwargs,
+    }
+    assert snapshot == {
+        "code": "500",
+        "recreate_kwargs": {"reason": "postgres_read_only_transaction"},
+    }
+
+
+@pytest.mark.asyncio
+async def test_handle_exception_on_proxy_leaves_writer_alone_for_other_db_errors(
+    monkeypatch: pytest.MonkeyPatch,
+) -> None:
+    prisma_client = MagicMock()
+    prisma_client.recreate_read_only_writer = AsyncMock(return_value=True)
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", prisma_client)
+
+    handle_exception_on_proxy(DataError(data={"user_facing_error": {"message": "deadlock detected"}}))
+    await asyncio.sleep(0)
+
+    assert prisma_client.recreate_read_only_writer.await_count == 0
diff --git a/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_health.py b/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_health.py
index 9f48ba68b4f..fbe9934f06c 100644
--- a/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_health.py
+++ b/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_health.py
@@ -22,6 +22,10 @@ from unittest.mock import AsyncMock, MagicMock
 
 import pytest
 
+from litellm.proxy.db.health_check_latest import (
+    LATEST_HEALTH_CHECKS_FOR_MODELS_SQL,
+    LATEST_HEALTH_CHECKS_SQL,
+)
 from litellm.proxy.utils import PrismaClient
 
 
@@ -261,36 +265,49 @@ async def test_get_health_check_history_db_error_returns_empty_list(
     assert await prisma_client.get_health_check_history() == []
 
 
+def _raw_health_check_row(model_name: str = "gpt-4", model_id: str | None = "deployment-abc") -> dict[str, Any]:
+    return {
+        "health_check_id": f"hc-{model_name}",
+        "model_name": model_name,
+        "model_id": model_id,
+        "status": "healthy",
+        "healthy_count": 1,
+        "unhealthy_count": 0,
+        "error_message": None,
+        "response_time_ms": 12.5,
+        "details": None,
+        "checked_by": "pod-1",
+        "checked_at": "2026-08-25T00:00:00+00:00",
+        "created_at": "2026-08-25T00:00:00+00:00",
+        "updated_at": "2026-08-25T00:00:00+00:00",
+    }
+
+
 @pytest.mark.asyncio
-async def test_get_all_latest_health_checks_uses_distinct(
+async def test_get_all_latest_health_checks_dedups_in_postgres(
     prisma_client: PrismaClient,
 ) -> None:
-    rows = [MagicMock(name=f"row-{i}") for i in range(3)]
-    prisma_client.db.litellm_healthchecktable.find_many = AsyncMock(return_value=rows)
+    """A revert to prisma find_many(distinct=...) streams the whole history table; the SQL must own the DISTINCT."""
+    prisma_client.db.query_raw = AsyncMock(return_value=[_raw_health_check_row()])
     result = await prisma_client.get_all_latest_health_checks()
-    kwargs = prisma_client.db.litellm_healthchecktable.find_many.await_args.kwargs
     actual = {
-        "len": len(result),
-        "distinct": kwargs["distinct"],
-        "order_len": len(kwargs["order"]),
-        "first_order": kwargs["order"][0],
+        "query": prisma_client.db.query_raw.await_args.args,
+        "rows": [(row.model_id, row.model_name, row.status) for row in result],
+        "row_type": type(result[0]).__name__,
     }
     assert actual == {
-        "len": 3,
-        "distinct": ["model_id", "model_name"],
-        "order_len": 3,
-        "first_order": {"model_id": "asc"},
+        "query": (LATEST_HEALTH_CHECKS_SQL,),
+        "rows": [("deployment-abc", "gpt-4", "healthy")],
+        "row_type": "LatestHealthCheckRow",
     }
 
 
 @pytest.mark.asyncio
-async def test_get_all_latest_health_checks_db_error_returns_empty_list(
+async def test_get_all_latest_health_checks_db_error_returns_no_rows(
     prisma_client: PrismaClient,
 ) -> None:
-    prisma_client.db.litellm_healthchecktable.find_many = AsyncMock(
-        side_effect=RuntimeError("oops")
-    )
-    assert await prisma_client.get_all_latest_health_checks() == []
+    prisma_client.db.query_raw = AsyncMock(side_effect=RuntimeError("oops"))
+    assert await prisma_client.get_all_latest_health_checks() == ()
 
 
 @pytest.mark.asyncio
@@ -298,18 +315,15 @@ async def test_get_latest_health_checks_for_models_bounds_the_query_to_those_mod
     prisma_client: PrismaClient,
 ) -> None:
     """A paged caller reads health for its page; an unbounded read is the bug this exists to avoid."""
-    prisma_client.db.litellm_healthchecktable.find_many = AsyncMock(return_value=[])
-    await prisma_client.get_latest_health_checks_for_models(["gpt-5", "claude-opus"])
-    kwargs = prisma_client.db.litellm_healthchecktable.find_many.await_args.kwargs
+    prisma_client.db.query_raw = AsyncMock(return_value=[_raw_health_check_row(model_name="gpt-5")])
+    result = await prisma_client.get_latest_health_checks_for_models(["gpt-5", "claude-opus"])
     actual = {
-        "where": kwargs["where"],
-        "distinct": kwargs["distinct"],
-        "order": kwargs["order"],
+        "query": prisma_client.db.query_raw.await_args.args,
+        "rows": [row.model_name for row in result],
     }
     assert actual == {
-        "where": {"model_name": {"in": ["gpt-5", "claude-opus"]}},
-        "distinct": ["model_id", "model_name"],
-        "order": [{"model_id": "asc"}, {"model_name": "asc"}, {"checked_at": "desc"}],
+        "query": (LATEST_HEALTH_CHECKS_FOR_MODELS_SQL, ["gpt-5", "claude-opus"]),
+        "rows": ["gpt-5"],
     }
 
 
@@ -317,14 +331,14 @@ async def test_get_latest_health_checks_for_models_bounds_the_query_to_those_mod
 async def test_get_latest_health_checks_for_models_does_not_query_for_an_empty_page(
     prisma_client: PrismaClient,
 ) -> None:
-    prisma_client.db.litellm_healthchecktable.find_many = AsyncMock(return_value=[])
+    prisma_client.db.query_raw = AsyncMock(return_value=[])
     assert await prisma_client.get_latest_health_checks_for_models([]) == ()
-    assert prisma_client.db.litellm_healthchecktable.find_many.await_count == 0
+    assert prisma_client.db.query_raw.await_count == 0
 
 
 @pytest.mark.asyncio
-async def test_get_latest_health_checks_for_models_db_error_returns_empty_list(
+async def test_get_latest_health_checks_for_models_db_error_returns_no_rows(
     prisma_client: PrismaClient,
 ) -> None:
-    prisma_client.db.litellm_healthchecktable.find_many = AsyncMock(side_effect=RuntimeError("oops"))
+    prisma_client.db.query_raw = AsyncMock(side_effect=RuntimeError("oops"))
     assert await prisma_client.get_latest_health_checks_for_models(["gpt-5"]) == ()
diff --git a/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_reconnect.py b/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_reconnect.py
index 41b0eb3cf95..cec6dd99ce8 100644
--- a/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_reconnect.py
+++ b/tests/test_litellm/proxy/utils/prisma_and_spend/test_prisma_client_reconnect.py
@@ -29,7 +29,7 @@ from __future__ import annotations
 import asyncio
 import time
 from typing import Any, Final
-from unittest.mock import AsyncMock, MagicMock
+from unittest.mock import AsyncMock, MagicMock, call
 
 import pytest
 
@@ -111,6 +111,34 @@ async def test_run_reconnect_cycle_direct_path_recreates_when_probe_fails(
     }
 
 
+@pytest.mark.asyncio
+async def test_run_reconnect_cycle_direct_path_recreates_when_writer_is_read_only(
+    prisma_client: PrismaClient, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setenv("DATABASE_URL", "postgres://x:y@h:5432/db")
+    prisma_client._engine_confirmed_dead = False
+    prisma_client._engine_pid = 0
+    prisma_client._start_engine_watcher = AsyncMock()
+    prisma_client._cleanup_engine_watcher = MagicMock()
+
+    writer: Final = MagicMock()
+    writer.query_raw = AsyncMock(side_effect=[[{"transaction_read_only": "on"}], [{"?column?": 1}]])
+    writer.recreate_prisma_client = AsyncMock()
+    prisma_client.db = writer
+
+    await prisma_client._run_reconnect_cycle(timeout_seconds=5)
+    pinned = {
+        "recreate_called": writer.recreate_prisma_client.await_count,
+        "start_watcher_called": prisma_client._start_engine_watcher.await_count,
+        "cleanup_called": prisma_client._cleanup_engine_watcher.call_count,
+    }
+    assert pinned == {
+        "recreate_called": 1,
+        "start_watcher_called": 1,
+        "cleanup_called": 1,
+    }
+
+
 @pytest.mark.asyncio
 async def test_run_reconnect_cycle_force_recreate_skips_probe_and_recreates(
     prisma_client: PrismaClient, monkeypatch: pytest.MonkeyPatch
@@ -488,6 +516,93 @@ async def test_db_health_watchdog_loop_swallows_non_db_errors(
     assert prisma_client.attempt_db_reconnect.await_count == 0
 
 
+def _routing_db_with_writer_sessions(*transaction_read_only: str) -> tuple[RoutingPrismaWrapper, MagicMock]:
+    """One watchdog cycle per value, then the loop is cancelled."""
+    writer: Final = MagicMock()
+    writer.query_raw = AsyncMock(side_effect=[[{"transaction_read_only": value}] for value in transaction_read_only])
+    reader: Final = MagicMock()
+    reader.query_raw = AsyncMock(
+        side_effect=[[{"?column?": 1}] for _ in transaction_read_only] + [asyncio.CancelledError()]
+    )
+    return RoutingPrismaWrapper(writer=writer, reader=reader), writer
+
+
+@pytest.mark.asyncio
+async def test_db_health_watchdog_loop_forces_recreate_when_writer_is_read_only(
+    prisma_client: PrismaClient,
+) -> None:
+    prisma_client._db_health_watchdog_interval_seconds = 0
+    prisma_client.attempt_db_reconnect = AsyncMock(side_effect=asyncio.CancelledError())
+    prisma_client.db, _ = _routing_db_with_writer_sessions("on")
+
+    await prisma_client._db_health_watchdog_loop()
+    assert prisma_client.attempt_db_reconnect.await_args is not None
+    assert prisma_client.attempt_db_reconnect.await_args.kwargs == {
+        "reason": "db_health_watchdog_writer_read_only",
+        "timeout_seconds": prisma_client._db_watchdog_reconnect_timeout_seconds,
+        "force_recreate": True,
+    }
+
+
+@pytest.mark.asyncio
+async def test_db_health_watchdog_loop_leaves_writable_writer_alone(
+    prisma_client: PrismaClient,
+) -> None:
+    prisma_client._db_health_watchdog_interval_seconds = 0
+    prisma_client.attempt_db_reconnect = AsyncMock()
+    prisma_client.db, writer = _routing_db_with_writer_sessions("off")
+
+    await prisma_client._db_health_watchdog_loop()
+    assert (prisma_client.attempt_db_reconnect.await_count, writer.query_raw.await_count) == (0, 1)
+
+
+@pytest.mark.asyncio
+async def test_db_health_watchdog_loop_backs_off_while_database_stays_read_only(
+    prisma_client: PrismaClient,
+) -> None:
+    prisma_client._db_health_watchdog_interval_seconds = 0
+    prisma_client.attempt_db_reconnect = AsyncMock(return_value=True)
+    prisma_client.db, writer = _routing_db_with_writer_sessions("on", "on", "on")
+
+    await prisma_client._db_health_watchdog_loop()
+    assert (prisma_client.attempt_db_reconnect.await_count, writer.query_raw.await_count) == (1, 3)
+
+
+@pytest.mark.asyncio
+async def test_db_health_watchdog_loop_recreates_again_once_writer_was_writable_in_between(
+    prisma_client: PrismaClient,
+) -> None:
+    prisma_client._db_health_watchdog_interval_seconds = 0
+    prisma_client.attempt_db_reconnect = AsyncMock(return_value=True)
+    prisma_client.db, _ = _routing_db_with_writer_sessions("on", "off", "on")
+
+    await prisma_client._db_health_watchdog_loop()
+    assert prisma_client.attempt_db_reconnect.await_count == 2
+
+
+@pytest.mark.asyncio
+async def test_recreate_read_only_writer_retries_after_backoff_elapses(
+    prisma_client: PrismaClient,
+) -> None:
+    prisma_client._db_reconnect_cooldown_seconds = 15
+    prisma_client.attempt_db_reconnect = AsyncMock(return_value=True)
+
+    first: Final = await prisma_client.recreate_read_only_writer(reason="postgres_read_only_transaction")
+    within_backoff: Final = await prisma_client.recreate_read_only_writer(reason="postgres_read_only_transaction")
+    prisma_client._db_read_only_recreate_ts -= 30
+    after_backoff: Final = await prisma_client.recreate_read_only_writer(reason="postgres_read_only_transaction")
+    prisma_client._db_read_only_recreate_ts -= 30
+    still_within_doubled_backoff: Final = await prisma_client.recreate_read_only_writer(
+        reason="postgres_read_only_transaction"
+    )
+
+    assert (first, within_backoff, after_backoff, still_within_doubled_backoff) == (True, False, True, False)
+    assert prisma_client.attempt_db_reconnect.await_args_list == [
+        call(reason="postgres_read_only_transaction", timeout_seconds=None, force_recreate=True),
+        call(reason="postgres_read_only_transaction", timeout_seconds=None, force_recreate=True),
+    ]
+
+
 @pytest.mark.asyncio
 async def test_iam_refresh_racing_reconnect_recreates_engine_only_once(
     prisma_client: PrismaClient, monkeypatch: pytest.MonkeyPatch
diff --git a/tests/test_litellm/proxy/utils/proxy_logging/test_guardrail_pipeline.py b/tests/test_litellm/proxy/utils/proxy_logging/test_guardrail_pipeline.py
index 5cb595840fc..dfe106a3f52 100644
--- a/tests/test_litellm/proxy/utils/proxy_logging/test_guardrail_pipeline.py
+++ b/tests/test_litellm/proxy/utils/proxy_logging/test_guardrail_pipeline.py
@@ -11,7 +11,9 @@ from __future__ import annotations
 
 import asyncio
 import json
+from copy import deepcopy
 import logging
+from collections.abc import Iterator
 from typing import Any, Callable, Dict, List
 from unittest.mock import AsyncMock, MagicMock, patch
 
@@ -25,11 +27,13 @@ from litellm.integrations.custom_guardrail import (
     ModifyResponseException,
 )
 from litellm.integrations.prometheus import PrometheusLogger
+from litellm.llms.base_llm.guardrail_translation.utils import stream_item_field
 from litellm.proxy._types import UserAPIKeyAuth
 from litellm.proxy.common_utils.callback_utils import add_guardrail_to_applied_guardrails_header
-from litellm.proxy.utils import ProxyLogging, _streamable_post_call_pipelines
+from litellm.proxy.utils import ProxyLogging, _streamable_post_call_pipelines, stream_gated_guardrail_names
 from litellm.proxy.guardrails.guardrail_hooks.litellm_content_filter.content_filter import ContentFilterGuardrail
 from litellm.types.guardrails import BlockedWord, ContentFilterAction, GuardrailEventHooks
+from litellm.types.llms.openai import ResponsesAPIResponse
 from litellm.types.proxy.policy_engine.pipeline_types import (
     GuardrailPipeline,
     PipelineStep,
@@ -154,9 +158,7 @@ async def test_execute_guardrail_hook_unknown_hook_type_raises(proxy_logging, ma
 
 
 @pytest.mark.asyncio
-async def test_execute_guardrail_with_load_balancing_routes_through_router(
-    proxy_logging, make_user_api_key_auth
-):
+async def test_execute_guardrail_with_load_balancing_routes_through_router(proxy_logging, make_user_api_key_auth):
     cb = _make_guardrail()
     router = MagicMock()
     router.get_available_guardrail = MagicMock(return_value={"callback": cb})
@@ -172,9 +174,7 @@ async def test_execute_guardrail_with_load_balancing_routes_through_router(
 
 
 @pytest.mark.asyncio
-async def test_execute_guardrail_with_load_balancing_router_none_raises(
-    proxy_logging, make_user_api_key_auth
-):
+async def test_execute_guardrail_with_load_balancing_router_none_raises(proxy_logging, make_user_api_key_auth):
     with patch("litellm.proxy.proxy_server.llm_router", None):
         with pytest.raises(ValueError, match="Router not initialized"):
             await proxy_logging._execute_guardrail_with_load_balancing(
@@ -187,9 +187,7 @@ async def test_execute_guardrail_with_load_balancing_router_none_raises(
 
 
 @pytest.mark.asyncio
-async def test_execute_guardrail_with_load_balancing_no_callback_raises(
-    proxy_logging, make_user_api_key_auth
-):
+async def test_execute_guardrail_with_load_balancing_no_callback_raises(proxy_logging, make_user_api_key_auth):
     router = MagicMock()
     router.get_available_guardrail = MagicMock(return_value={"callback": None})
     with patch("litellm.proxy.proxy_server.llm_router", router):
@@ -209,9 +207,7 @@ async def test_execute_guardrail_with_load_balancing_no_callback_raises(
 
 
 @pytest.mark.asyncio
-async def test_process_guardrail_callback_skipped_when_should_run_false(
-    proxy_logging, make_user_api_key_auth
-):
+async def test_process_guardrail_callback_skipped_when_should_run_false(proxy_logging, make_user_api_key_auth):
     cb = _make_guardrail()
     cb.should_run_guardrail = MagicMock(return_value=False)
     out = await proxy_logging._process_guardrail_callback(
@@ -225,9 +221,7 @@ async def test_process_guardrail_callback_skipped_when_should_run_false(
 
 
 @pytest.mark.asyncio
-async def test_process_guardrail_callback_returns_data_on_success(
-    proxy_logging, make_user_api_key_auth, monkeypatch
-):
+async def test_process_guardrail_callback_returns_data_on_success(proxy_logging, make_user_api_key_auth, monkeypatch):
     cb = _make_guardrail()
     cb.should_run_guardrail = MagicMock(return_value=True)
     proxy_logging._should_use_guardrail_load_balancing = MagicMock(return_value=False)
@@ -342,14 +336,14 @@ async def test_maybe_execute_pipelines_no_pipelines_returns_data(proxy_logging,
 
 
 @pytest.mark.asyncio
-async def test_maybe_execute_pipelines_skips_pipelines_with_other_mode(proxy_logging, make_user_api_key_auth, monkeypatch):
+async def test_maybe_execute_pipelines_skips_pipelines_with_other_mode(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
     pipeline = MagicMock()
     pipeline.mode = "post_call"  # not pre_call
     data = {"metadata": {"_guardrail_pipelines": [("p1", pipeline)]}, "model": "m", "messages": []}
     executed = MagicMock()
-    monkeypatch.setattr(
-        "litellm.proxy.policy_engine.pipeline_executor.PipelineExecutor.execute_steps", executed
-    )
+    monkeypatch.setattr("litellm.proxy.policy_engine.pipeline_executor.PipelineExecutor.execute_steps", executed)
     out, replacement = await proxy_logging._maybe_execute_pipelines(
         data=data,
         user_api_key_dict=make_user_api_key_auth(),
@@ -537,9 +531,7 @@ def test_handle_pipeline_result_block_enriches_with_guardrail_name_and_mode():
     litellm.callbacks = [cb]
     try:
         with pytest.raises(HTTPException) as info:
-            ProxyLogging._handle_pipeline_result(
-                result=result, data={"model": "m"}, policy_name="p"
-            )
+            ProxyLogging._handle_pipeline_result(result=result, data={"model": "m"}, policy_name="p")
     finally:
         litellm.callbacks = saved
 
@@ -651,9 +643,7 @@ async def test_run_guardrail_with_metrics_records_error_and_enriches(monkeypatch
     monkeypatch.setattr(litellm, "callbacks", [prom])
 
     with pytest.raises(HTTPException):
-        await ProxyLogging._run_guardrail_with_metrics(
-            callback=cb, coro=task(), hook_type="post_call"
-        )
+        await ProxyLogging._run_guardrail_with_metrics(callback=cb, coro=task(), hook_type="post_call")
 
     assert detail["guardrail_name"] == "presidio"
     recorded = prom._record_guardrail_metrics.call_args.kwargs
@@ -681,9 +671,7 @@ def _moderation_guardrail() -> MagicMock:
 
 
 @pytest.mark.asyncio
-async def test_during_call_hook_records_latency_metric(
-    proxy_logging, make_user_api_key_auth, monkeypatch
-):
+async def test_during_call_hook_records_latency_metric(proxy_logging, make_user_api_key_auth, monkeypatch):
     cb = _moderation_guardrail()
     prom = _prometheus_callback()
     monkeypatch.setattr(litellm, "callbacks", [prom, cb])
@@ -702,9 +690,7 @@ async def test_during_call_hook_records_latency_metric(
 
 
 @pytest.mark.asyncio
-async def test_post_call_success_hook_records_latency_metric(
-    proxy_logging, make_user_api_key_auth, monkeypatch
-):
+async def test_post_call_success_hook_records_latency_metric(proxy_logging, make_user_api_key_auth, monkeypatch):
     cb = _moderation_guardrail()
     prom = _prometheus_callback()
     monkeypatch.setattr(litellm, "callbacks", [prom, cb])
@@ -732,9 +718,7 @@ async def test_post_call_success_hook_records_latency_metric(
 async def test_process_prompt_template_no_op_when_no_prompt_spec(proxy_logging, monkeypatch):
     from litellm.proxy.prompts import prompt_registry
 
-    monkeypatch.setattr(
-        prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: None
-    )
+    monkeypatch.setattr(prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: None)
     data: Dict[str, Any] = {"messages": [{"role": "user"}], "model": "m", "temperature": 0.1}
     await proxy_logging._process_prompt_template(
         data=data,
@@ -759,9 +743,7 @@ async def test_process_prompt_template_applies_when_spec_resolves(proxy_logging,
         "get_prompt_callback_for_prompt",
         lambda *a, **kw: custom_logger,
     )
-    monkeypatch.setattr(
-        prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: prompt_spec
-    )
+    monkeypatch.setattr(prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: prompt_spec)
 
     logging_obj = MagicMock()
     logging_obj.async_get_chat_completion_prompt = AsyncMock(
@@ -809,9 +791,7 @@ async def test_process_prompt_template_async_get_prompt_error_raises(proxy_loggi
         "get_prompt_callback_for_prompt",
         lambda *a, **kw: custom_logger,
     )
-    monkeypatch.setattr(
-        prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: prompt_spec
-    )
+    monkeypatch.setattr(prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: prompt_spec)
     logging_obj = MagicMock()
     logging_obj.async_get_chat_completion_prompt = AsyncMock(side_effect=RuntimeError("bad prompt"))
     with pytest.raises(RuntimeError):
@@ -912,9 +892,7 @@ async def test_process_prompt_template_aresponses_swaps_model_and_merges_input(p
         "get_prompt_callback_for_prompt",
         lambda *a, **kw: custom_logger,
     )
-    monkeypatch.setattr(
-        prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: prompt_spec
-    )
+    monkeypatch.setattr(prompt_registry.IN_MEMORY_PROMPT_REGISTRY, "resolve_prompt_spec", lambda *a, **kw: prompt_spec)
 
     logging_obj = MagicMock()
     logging_obj.async_get_chat_completion_prompt = AsyncMock(
@@ -965,6 +943,7 @@ def _post_call_pipeline_data(
         "metadata": {
             "_guardrail_pipelines": [("response-governance", pipeline)],
             "_pipeline_managed_guardrails": {guardrail},
+            "policy_sources": {"response-governance": "model:m"},
         },
         **extra,
     }
@@ -1123,9 +1102,7 @@ async def test_pre_call_hook_still_runs_guardrail_managed_only_by_post_call_pipe
         },
     }
 
-    await proxy_logging.pre_call_hook(
-        user_api_key_dict=make_user_api_key_auth(), data=data, call_type="completion"
-    )
+    await proxy_logging.pre_call_hook(user_api_key_dict=make_user_api_key_auth(), data=data, call_type="completion")
 
     assert seen["count"] == 1
 
@@ -1288,11 +1265,7 @@ async def test_post_call_pipeline_block_keeps_guardrail_metadata_writes(
     monkeypatch.setattr(
         litellm,
         "callbacks",
-        [
-            BlockingWriterGuardrail(
-                guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False
-            )
-        ],
+        [BlockingWriterGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False)],
     )
     monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
     data = _post_call_pipeline_data()
@@ -1378,9 +1351,7 @@ async def test_pre_call_pipeline_managed_parallel_guardrail_runs_exactly_once(
         },
     }
 
-    await proxy_logging.pre_call_hook(
-        user_api_key_dict=make_user_api_key_auth(), data=data, call_type="completion"
-    )
+    await proxy_logging.pre_call_hook(user_api_key_dict=make_user_api_key_auth(), data=data, call_type="completion")
 
     assert seen["count"] == 1
 
@@ -1419,10 +1390,295 @@ async def test_streaming_request_whose_pipeline_guardrail_is_missing_streams_ver
     assert any("response-governance" in message and "gr-post" in message for message in _warnings(caplog))
 
 
+def _background_response(status: str, text: str = "") -> ResponsesAPIResponse:
+    output = (
+        [{"type": "message", "role": "assistant", "content": [{"type": "output_text", "text": text}]}] if text else []
+    )
+    return ResponsesAPIResponse(id="resp_bg", created_at=0, output=output, status=status)
+
+
+def _output_blocking_callbacks(seen: dict[str, object]) -> list[CustomGuardrail]:
+    class OutputBlockingGuardrail(CustomGuardrail):
+        async def async_post_call_success_hook(self, data, user_api_key_dict, response):
+            seen["response"] = response
+            raise HTTPException(status_code=400, detail={"error": "output blocked"})
+
+    return [
+        OutputBlockingGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False)
+    ]
+
+
 @pytest.mark.asyncio
-async def test_pre_call_hook_accepts_background_request_with_post_call_pipeline(
-    proxy_logging, make_user_api_key_auth, monkeypatch, caplog
+@pytest.mark.parametrize("pending_status", ["queued", "in_progress"])
+async def test_post_call_success_hook_waits_for_pending_background_response_before_running_pipeline(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    caplog: pytest.LogCaptureFixture,
+    pending_status: str,
+) -> None:
+    seen: dict[str, object] = {}
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks(seen))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(background=True)
+    response = _background_response(pending_status)
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Proxy"):
+        out = await proxy_logging.post_call_success_hook(
+            data=data, response=response, user_api_key_dict=make_user_api_key_auth()
+        )
+
+    assert out is response
+    assert "response" not in seen
+    assert not _warnings(caplog)
+    assert any(
+        "response-governance" in record.getMessage() and pending_status in record.getMessage()
+        for record in caplog.records
+    )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("final_status", ["completed", "incomplete"])
+async def test_post_call_success_hook_runs_pipeline_on_retrieved_background_response(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    final_status: str,
+) -> None:
+    seen: dict[str, object] = {}
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks(seen))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data()
+    response = _background_response(final_status, text="kumquat")
+
+    with pytest.raises(HTTPException) as info:
+        await proxy_logging.post_call_success_hook(
+            data=data, response=response, user_api_key_dict=make_user_api_key_auth()
+        )
+
+    assert info.value.detail["error"] == "output blocked"
+    assert seen["response"] is response
+
+
+def _output_passing_callbacks() -> list[CustomGuardrail]:
+    class OutputPassingGuardrail(CustomGuardrail):
+        async def async_post_call_success_hook(self, data, user_api_key_dict, response):
+            return response
+
+    return [
+        OutputPassingGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False)
+    ]
+
+
+def _claimed_post_call_pipeline_data(
+    *policy_names: str, extra_guardrails: dict[str, list[str]] | None = None, policy_source: str | None = "model:m"
 ):
+    from litellm.proxy.policy_engine.policy_registry import get_policy_registry
+
+    step = {"guardrail": "gr-post", "on_pass": "allow", "on_fail": "block"}
+    get_policy_registry().load_policies(
+        {
+            policy_name: {
+                "guardrails": {"add": ["gr-post", *(extra_guardrails or {}).get(policy_name, [])]},
+                "pipeline": {"mode": "post_call", "steps": [step]},
+            }
+            for policy_name in policy_names
+        }
+    )
+    pipeline = GuardrailPipeline(mode="post_call", steps=[PipelineStep(**step)])
+    return {
+        "model": "m",
+        "messages": [{"role": "user", "content": "hi"}],
+        "metadata": {
+            "_guardrail_pipelines": [(policy_name, pipeline) for policy_name in policy_names],
+            "_pipeline_managed_guardrails": {"gr-post"},
+            "applied_policies": list(policy_names),
+            "applied_guardrails": ["gr-post", *(g for gs in (extra_guardrails or {}).values() for g in gs)],
+            "policy_sources": {policy_name: policy_source for policy_name in policy_names if policy_source is not None},
+        },
+    }
+
+
+@pytest.fixture
+def clear_policy_registry() -> Iterator[None]:
+    from litellm.proxy.policy_engine.policy_registry import get_policy_registry
+
+    yield
+    get_policy_registry().clear()
+
+
+@pytest.mark.asyncio
+async def test_pending_background_response_withdraws_the_deferred_policy_claims(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+) -> None:
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks({}))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _claimed_post_call_pipeline_data("response-governance")
+
+    out = await proxy_logging.post_call_success_hook(
+        data=data, response=_background_response("queued"), user_api_key_dict=make_user_api_key_auth()
+    )
+
+    assert out.status == "queued"
+    assert "applied_policies" not in data["metadata"]
+    assert "policy_sources" not in data["metadata"]
+    assert "applied_guardrails" not in data["metadata"]
+
+
+@pytest.mark.asyncio
+async def test_pending_background_response_warns_when_the_deferred_policy_was_matched_through_a_tag(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+    caplog: pytest.LogCaptureFixture,
+) -> None:
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks({}))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _claimed_post_call_pipeline_data("response-governance", policy_source="tag:governed+model:m")
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        out = await proxy_logging.post_call_success_hook(
+            data=data, response=_background_response("queued"), user_api_key_dict=make_user_api_key_auth()
+        )
+
+    assert out.status == "queued"
+    assert "policy_sources" not in data["metadata"]
+    assert [message for message in _warnings(caplog) if "through a request tag" in message] == [
+        "Policy engine: background response resp_bg matched post_call policies through a request tag at submit; "
+        "retrieval re-matches only the key, team, and model scopes, so a tag carried in the request body "
+        "does not govern the completed response: response-governance"
+    ]
+
+
+@pytest.mark.asyncio
+async def test_pending_background_response_warns_when_the_deferred_policy_came_from_the_request_body(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+    caplog: pytest.LogCaptureFixture,
+) -> None:
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks({}))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _claimed_post_call_pipeline_data("body-governance", policy_source=None)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        out = await proxy_logging.post_call_success_hook(
+            data=data, response=_background_response("queued"), user_api_key_dict=make_user_api_key_auth()
+        )
+
+    assert out.status == "queued"
+    assert "policy_sources" not in data["metadata"]
+    assert _warnings(caplog) == [
+        "Policy engine: background response resp_bg matched post_call policies through the request body's policies "
+        "list at submit; retrieval carries no request body, so those policies do not govern the completed "
+        "response: body-governance"
+    ]
+
+
+@pytest.mark.asyncio
+async def test_pending_background_response_matched_through_its_model_does_not_warn(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+    caplog: pytest.LogCaptureFixture,
+) -> None:
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks({}))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        await proxy_logging.post_call_success_hook(
+            data=_claimed_post_call_pipeline_data("response-governance"),
+            response=_background_response("queued"),
+            user_api_key_dict=make_user_api_key_auth(),
+        )
+
+    assert _warnings(caplog) == []
+
+
+@pytest.mark.asyncio
+async def test_pending_background_response_keeps_the_claim_of_a_policy_that_runs_outside_its_pipeline(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+) -> None:
+    monkeypatch.setattr(litellm, "callbacks", _output_blocking_callbacks({}))
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _claimed_post_call_pipeline_data(
+        "input-and-output-governance",
+        "response-governance",
+        extra_guardrails={"input-and-output-governance": ["gr-pre"]},
+    )
+
+    await proxy_logging.post_call_success_hook(
+        data=data, response=_background_response("in_progress"), user_api_key_dict=make_user_api_key_auth()
+    )
+
+    assert data["metadata"]["applied_policies"] == ["input-and-output-governance"]
+    assert data["metadata"]["applied_guardrails"] == ["gr-pre"]
+    assert data["metadata"]["policy_sources"] == {"input-and-output-governance": "model:m"}
+
+
+@pytest.mark.asyncio
+async def test_pending_background_response_keeps_the_claim_of_a_default_on_guardrail_that_ran_pre_call(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+) -> None:
+    class DualStageGuardrail(CustomGuardrail):
+        async def async_post_call_success_hook(self, data, user_api_key_dict, response):
+            return response
+
+    monkeypatch.setattr(
+        litellm,
+        "callbacks",
+        [DualStageGuardrail(guardrail_name="gr-post", event_hook=["pre_call", "post_call"], default_on=True)],
+    )
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _claimed_post_call_pipeline_data("response-governance")
+
+    await proxy_logging.post_call_success_hook(
+        data=data, response=_background_response("queued"), user_api_key_dict=make_user_api_key_auth()
+    )
+
+    assert "applied_policies" not in data["metadata"]
+    assert data["metadata"]["applied_guardrails"] == ["gr-post"]
+
+
+@pytest.mark.asyncio
+async def test_retrieved_background_response_keeps_the_policy_claim_once_its_pipeline_ran(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    clear_policy_registry: None,
+) -> None:
+    monkeypatch.setattr(litellm, "callbacks", _output_passing_callbacks())
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _claimed_post_call_pipeline_data("response-governance")
+
+    await proxy_logging.post_call_success_hook(
+        data=data, response=_background_response("completed", text="fine"), user_api_key_dict=make_user_api_key_auth()
+    )
+
+    assert data["metadata"]["applied_policies"] == ["response-governance"]
+    assert data["metadata"]["policy_sources"] == {"response-governance": "model:m"}
+    assert data["metadata"]["applied_guardrails"] == ["gr-post"]
+
+
+@pytest.mark.asyncio
+async def test_pre_call_hook_stays_quiet_on_background_request_with_post_call_pipeline(
+    proxy_logging: ProxyLogging,
+    make_user_api_key_auth: Callable[..., UserAPIKeyAuth],
+    monkeypatch: pytest.MonkeyPatch,
+    caplog: pytest.LogCaptureFixture,
+) -> None:
     monkeypatch.setattr(litellm, "callbacks", [])
     data = _post_call_pipeline_data(background=True)
 
@@ -1436,36 +1692,7 @@ async def test_pre_call_hook_accepts_background_request_with_post_call_pipeline(
 
     assert out is not None
     assert out.get("background") is True
-    assert any("response-governance" in message and "background" in message for message in _warnings(caplog))
-
-
-@pytest.mark.asyncio
-async def test_pre_call_hook_stays_quiet_on_background_request_without_post_call_pipeline(
-    proxy_logging, make_user_api_key_auth, monkeypatch, caplog
-):
-    seen: Dict[str, Any] = {}
-    monkeypatch.setattr(litellm, "callbacks", [_unified_stream_guardrail(seen)])
-    pre_call = GuardrailPipeline(mode="pre_call", steps=[PipelineStep(guardrail="gr-post", on_fail="block")])
-    data = {
-        "model": "m",
-        "messages": [{"role": "user", "content": "hi"}],
-        "background": True,
-        "metadata": {
-            "_guardrail_pipelines": [("request-governance", pre_call)],
-            "_pipeline_managed_guardrails": {"gr-post"},
-        },
-    }
-
-    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
-        out = await proxy_logging.pre_call_hook(
-            user_api_key_dict=make_user_api_key_auth(),
-            data=data,
-            call_type="aresponses",
-            guardrails_only=True,
-        )
-
-    assert out is not None
-    assert not any("background" in message for message in _warnings(caplog))
+    assert not _warnings(caplog)
 
 
 # ---------------------------------------------------------------------------
@@ -1497,29 +1724,131 @@ async def _async_chunk_iter(chunks: List[Any]):
         yield chunk
 
 
-def test_streamable_post_call_pipelines_keeps_supported_and_drops_unsupported(
+def _legacy_hook_stream_guardrail(
+    seen: Dict[str, Any],
+    rewrite: Callable[[Any], Any] | None = None,
+    raises: Exception | None = None,
+    native_lifecycle: bool = False,
+) -> CustomGuardrail:
+    class LegacyHookGuardrail(CustomGuardrail):
+        use_native_lifecycle_hooks = native_lifecycle
+
+        async def async_post_call_success_hook(self, data, user_api_key_dict, response):
+            seen["count"] = seen.get("count", 0) + 1
+            seen["data"] = data
+            seen["user_api_key_dict"] = user_api_key_dict
+            seen["response"] = deepcopy(response)
+            if raises is not None:
+                raise raises
+            return None if rewrite is None else rewrite(response)
+
+    if native_lifecycle:
+
+        class NativeLifecycleGuardrail(LegacyHookGuardrail):
+            async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+                raise AssertionError("a guardrail that keeps its native hooks never runs apply_guardrail")
+
+        return NativeLifecycleGuardrail(
+            guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False
+        )
+    return LegacyHookGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False)
+
+
+def _iterator_hook_only_guardrail(name: str, seen: Dict[str, Any]) -> CustomGuardrail:
+    class IteratorHookGuardrail(CustomGuardrail):
+        async def async_post_call_streaming_iterator_hook(self, user_api_key_dict, response, request_data):
+            seen["count"] = seen.get("count", 0) + 1
+            async for item in response:
+                item.choices[0].delta.content = f"[governed] {item.choices[0].delta.content}"
+                yield item
+
+    return IteratorHookGuardrail(guardrail_name=name, event_hook=GuardrailEventHooks.post_call, default_on=True)
+
+
+def _iterator_and_legacy_hook_guardrail(name: str, seen: Dict[str, Any]) -> CustomGuardrail:
+    class IteratorAndLegacyHookGuardrail(CustomGuardrail):
+        async def async_post_call_success_hook(self, data, user_api_key_dict, response):
+            seen["success_hook_calls"] = seen.get("success_hook_calls", 0) + 1
+            return None
+
+        async def async_post_call_streaming_iterator_hook(self, user_api_key_dict, response, request_data):
+            seen["iterator_hook_calls"] = seen.get("iterator_hook_calls", 0) + 1
+            async for item in response:
+                item.choices[0].delta.content = f"[governed] {item.choices[0].delta.content}"
+                yield item
+
+    return IteratorAndLegacyHookGuardrail(guardrail_name=name, event_hook=GuardrailEventHooks.post_call, default_on=True)
+
+
+def _rewritten_model_response(response: Any) -> litellm.ModelResponse:
+    payload = response.model_dump()
+    payload["choices"][0]["message"]["content"] = "[REWRITTEN] " + payload["choices"][0]["message"]["content"]
+    return litellm.ModelResponse(**payload)
+
+
+def test_streamable_post_call_pipelines_keeps_hook_guardrails_and_drops_iterator_only(
     make_user_api_key_auth, monkeypatch, caplog
 ):
-    class NativeOnlyGuardrail(CustomGuardrail):
-        pass
-
     supported = _unified_stream_guardrail({})
-    native_only = NativeOnlyGuardrail(guardrail_name="gr-native", event_hook=GuardrailEventHooks.post_call)
-    monkeypatch.setattr(litellm, "callbacks", [supported, native_only])
-    governed = GuardrailPipeline(mode="post_call", steps=[PipelineStep(guardrail="gr-post", on_fail="block")])
+    legacy = _legacy_hook_stream_guardrail({})
+    legacy.guardrail_name = "gr-legacy"
+    iterator_only = _iterator_hook_only_guardrail("gr-iterator", {})
+    monkeypatch.setattr(litellm, "callbacks", [supported, legacy, iterator_only])
+    governed = GuardrailPipeline(
+        mode="post_call",
+        steps=[PipelineStep(guardrail="gr-post", on_fail="next"), PipelineStep(guardrail="gr-legacy", on_fail="block")],
+    )
     ungoverned = GuardrailPipeline(
         mode="post_call",
-        steps=[PipelineStep(guardrail="gr-post", on_fail="next"), PipelineStep(guardrail="gr-native", on_fail="block")],
+        steps=[PipelineStep(guardrail="gr-post", on_fail="next"), PipelineStep(guardrail="gr-iterator", on_fail="block")],
     )
-    pre_call = GuardrailPipeline(mode="pre_call", steps=[PipelineStep(guardrail="gr-native", on_fail="block")])
-    data = {"metadata": {"_guardrail_pipelines": [("governed", governed), ("ungoverned", ungoverned), ("req", pre_call)]}}
+    pre_call = GuardrailPipeline(mode="pre_call", steps=[PipelineStep(guardrail="gr-iterator", on_fail="block")])
+    data = {
+        "metadata": {"_guardrail_pipelines": [("governed", governed), ("ungoverned", ungoverned), ("req", pre_call)]}
+    }
 
     with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
         streamable = _streamable_post_call_pipelines(data, make_user_api_key_auth(request_route="/v1/chat/completions"))
 
     assert streamable == (("governed", governed),)
-    assert any("'ungoverned'" in message and "gr-native" in message for message in _warnings(caplog))
-    assert not any("'governed'" in message for message in _warnings(caplog))
+    assert any("'ungoverned'" in message and "gr-iterator" in message for message in _warnings(caplog))
+    assert not any("'governed'" in message or "gr-legacy" in message for message in _warnings(caplog))
+
+
+@pytest.mark.parametrize(
+    "request_route",
+    ["/v1/completions", "/v1beta/models/gemini-2.5-flash:streamGenerateContent", "/a2a/agent"],
+)
+def test_streamable_post_call_pipelines_keeps_legacy_hooks_off_routes_that_assemble_no_response(
+    make_user_api_key_auth, monkeypatch, caplog, request_route
+):
+    monkeypatch.setattr(litellm, "callbacks", [_legacy_hook_stream_guardrail({})])
+    legacy = GuardrailPipeline(mode="post_call", steps=[PipelineStep(guardrail="gr-post", on_fail="block")])
+    data = {"metadata": {"_guardrail_pipelines": [("legacy-governance", legacy)]}}
+    auth = make_user_api_key_auth(request_route=request_route)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        streamable = _streamable_post_call_pipelines(data, auth)
+
+    assert streamable == ()
+    assert stream_gated_guardrail_names(data, auth) == frozenset()
+    assert any("'legacy-governance'" in message and "gr-post" in message for message in _warnings(caplog))
+
+
+def test_streamable_post_call_pipelines_keeps_guardrails_with_their_own_iterator_hook_on_their_own_path(
+    make_user_api_key_auth, monkeypatch, caplog
+):
+    monkeypatch.setattr(litellm, "callbacks", [_iterator_and_legacy_hook_guardrail("gr-post", {})])
+    both_hooks = GuardrailPipeline(mode="post_call", steps=[PipelineStep(guardrail="gr-post", on_fail="block")])
+    data = {"metadata": {"_guardrail_pipelines": [("both-hooks", both_hooks)]}}
+    auth = make_user_api_key_auth(request_route="/v1/chat/completions")
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        streamable = _streamable_post_call_pipelines(data, auth)
+
+    assert streamable == ()
+    assert stream_gated_guardrail_names(data, auth) == frozenset()
+    assert any("'both-hooks'" in message and "gr-post" in message for message in _warnings(caplog))
 
 
 def test_streamable_post_call_pipelines_is_empty_on_route_without_translation(
@@ -1569,55 +1898,123 @@ async def test_pre_call_hook_allows_streaming_when_pipeline_guardrail_supports_u
 
 @pytest.mark.asyncio
 @pytest.mark.parametrize("native_lifecycle", [False, True])
-async def test_streaming_iterator_hook_releases_stream_when_pipeline_guardrail_lacks_unified_support(
+async def test_streaming_iterator_hook_runs_legacy_hook_and_delivers_its_rewrite(
     proxy_logging, make_user_api_key_auth, monkeypatch, native_lifecycle, caplog
 ):
     seen: Dict[str, Any] = {}
-    if native_lifecycle:
-
-        class NativeOnlyGuardrail(CustomGuardrail):
-            use_native_lifecycle_hooks = True
-
-            async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
-                seen["count"] = seen.get("count", 0) + 1
-                return inputs
-
-    else:
-
-        class NativeOnlyGuardrail(CustomGuardrail):
-            async def async_post_call_success_hook(self, data, user_api_key_dict, response):
-                seen["count"] = seen.get("count", 0) + 1
-                return response
-
-    monkeypatch.setattr(
-        litellm,
-        "callbacks",
-        [NativeOnlyGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False)],
-    )
+    guardrail = _legacy_hook_stream_guardrail(seen, rewrite=_rewritten_model_response, native_lifecycle=native_lifecycle)
+    monkeypatch.setattr(litellm, "callbacks", [guardrail])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
     data = _post_call_pipeline_data(stream=True)
     chunks = _stream_chunks()
-    delivered: List[Any] = []
+    auth = make_user_api_key_auth(request_route="/v1/chat/completions")
 
     with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
         out = await proxy_logging.pre_call_hook(
-            user_api_key_dict=make_user_api_key_auth(),
-            data=data,
-            call_type="completion",
-            guardrails_only=True,
+            user_api_key_dict=auth, data=data, call_type="completion", guardrails_only=True
         )
+        delivered = [
+            item
+            async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+                user_api_key_dict=auth, response=_async_chunk_iter(chunks), request_data=data
+            )
+        ]
+
+    assert out is not None and out.get("stream") is True
+    assert seen["count"] == 1
+    assert isinstance(seen["response"], litellm.ModelResponse)
+    assert seen["response"].choices[0].message.content == "hello world"
+    assert seen["data"]["messages"] == data["messages"]
+    assert seen["user_api_key_dict"] is auth
+    assert [id(item) for item in delivered] == [id(chunk) for chunk in chunks]
+    assert delivered[0].choices[0].delta.content == "[REWRITTEN] hello world"
+    assert delivered[1].choices[0].delta.content in (None, "")
+    assert delivered[1].choices[0].finish_reason == "stop"
+    assert data["metadata"]["applied_guardrails"] == ["gr-post"]
+    assert _warnings(caplog) == []
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_releases_stream_untouched_when_legacy_hook_returns_none(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
+    seen: Dict[str, Any] = {}
+    monkeypatch.setattr(litellm, "callbacks", [_legacy_hook_stream_guardrail(seen)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+    chunks = _stream_chunks()
+
+    delivered = [
+        item
         async for item in proxy_logging.async_post_call_streaming_iterator_hook(
             user_api_key_dict=make_user_api_key_auth(request_route="/v1/chat/completions"),
             response=_async_chunk_iter(chunks),
             request_data=data,
+        )
+    ]
+
+    assert seen["count"] == 1
+    assert [id(item) for item in delivered] == [id(chunk) for chunk in chunks]
+    assert [item.choices[0].delta.content for item in delivered] == ["hello ", "world"]
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_ends_stream_with_legacy_hook_exception(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
+    seen: Dict[str, Any] = {}
+    blocked = HTTPException(status_code=400, detail={"error": "output blocked"})
+    monkeypatch.setattr(litellm, "callbacks", [_legacy_hook_stream_guardrail(seen, raises=blocked)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+    delivered: List[Any] = []
+
+    async def _drain() -> None:
+        async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+            user_api_key_dict=make_user_api_key_auth(request_route="/v1/chat/completions"),
+            response=_async_chunk_iter(_stream_chunks()),
+            request_data=data,
         ):
             delivered.append(item)
 
-    assert out is not None
-    assert out.get("stream") is True
-    assert [item is chunk for item, chunk in zip(delivered, chunks)] == [True, True]
-    assert len(delivered) == 2
-    assert seen.get("count") is None
-    assert any("'response-governance'" in message and "gr-post" in message for message in _warnings(caplog))
+    with pytest.raises(HTTPException) as info:
+        await _drain()
+
+    assert seen["count"] == 1
+    assert delivered == []
+    assert info.value is blocked
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_delivers_legacy_hook_rewrite_on_anthropic_sse(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
+    seen: Dict[str, Any] = {}
+
+    def rewrite(response: Any) -> Dict[str, Any]:
+        return {**response, "content": [{"type": "text", "text": "[REWRITTEN] " + response["content"][0]["text"]}]}
+
+    monkeypatch.setattr(litellm, "callbacks", [_legacy_hook_stream_guardrail(seen, rewrite=rewrite)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    delivered = [
+        item
+        async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+            user_api_key_dict=make_user_api_key_auth(request_route="/v1/messages"),
+            response=_async_chunk_iter(_anthropic_sse_chunks()),
+            request_data=data,
+        )
+    ]
+
+    assert seen["count"] == 1
+    assert seen["response"]["content"][0]["text"] == "hello world"
+    assert seen["response"]["role"] == "assistant"
+    raw = b"".join(delivered).decode()
+    assert "[REWRITTEN] hello world" in raw
+    assert raw.count("event: content_block_delta") == 1
+    for expected_event in ("message_start", "content_block_start", "content_block_stop", "message_delta", "message_stop"):
+        assert f"event: {expected_event}" in raw
 
 
 @pytest.mark.asyncio
@@ -1625,19 +2022,7 @@ async def test_streaming_iterator_hook_runs_iterator_hook_guardrail_whose_pipeli
     proxy_logging, make_user_api_key_auth, monkeypatch, caplog
 ):
     seen: Dict[str, Any] = {}
-
-    class IteratorHookGuardrail(CustomGuardrail):
-        async def async_post_call_streaming_iterator_hook(self, user_api_key_dict, response, request_data):
-            seen["count"] = seen.get("count", 0) + 1
-            async for item in response:
-                item.choices[0].delta.content = f"[governed] {item.choices[0].delta.content}"
-                yield item
-
-    monkeypatch.setattr(
-        litellm,
-        "callbacks",
-        [IteratorHookGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=True)],
-    )
+    monkeypatch.setattr(litellm, "callbacks", [_iterator_hook_only_guardrail("gr-post", seen)])
     monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
     data = _post_call_pipeline_data(stream=True)
 
@@ -1656,6 +2041,30 @@ async def test_streaming_iterator_hook_runs_iterator_hook_guardrail_whose_pipeli
     assert any("'response-governance'" in message and "gr-post" in message for message in _warnings(caplog))
 
 
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_runs_the_iterator_hook_of_a_guardrail_that_also_has_a_post_call_hook(
+    proxy_logging, make_user_api_key_auth, monkeypatch, caplog
+):
+    seen: Dict[str, Any] = {}
+    monkeypatch.setattr(litellm, "callbacks", [_iterator_and_legacy_hook_guardrail("gr-post", seen)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        delivered = [
+            item
+            async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+                user_api_key_dict=make_user_api_key_auth(request_route="/v1/chat/completions"),
+                response=_async_chunk_iter(_stream_chunks()),
+                request_data=data,
+            )
+        ]
+
+    assert seen == {"iterator_hook_calls": 1}
+    assert [item.choices[0].delta.content for item in delivered] == ["[governed] hello ", "[governed] world"]
+    assert any("'response-governance'" in message and "gr-post" in message for message in _warnings(caplog))
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "rewrite_attribute, value",
@@ -1812,7 +2221,9 @@ def _rewriting_stream_guardrail(transform: Callable[[Dict[str, Any]], Dict[str,
         async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
             return {**inputs, **transform(inputs)}
 
-    return RewritingStreamGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False)
+    return RewritingStreamGuardrail(
+        guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=False
+    )
 
 
 def _tool_call_stream_chunks() -> List[Any]:
@@ -1836,7 +2247,7 @@ def _echoed_tool_call_dicts(arguments: str) -> List[Dict[str, Any]]:
 
 @pytest.mark.asyncio
 @pytest.mark.parametrize("on_fail, on_error", [("block", None), ("next", "next")])
-async def test_streaming_iterator_hook_pipeline_releases_originals_on_runtime_tool_call_rewrite(
+async def test_streaming_iterator_hook_pipeline_delivers_runtime_tool_call_rewrite(
     proxy_logging, make_user_api_key_auth, monkeypatch, on_fail, on_error, caplog
 ):
     transform = lambda inputs: {"tool_calls": _echoed_tool_call_dicts('{"ssn": "[MASKED]"}')}  # noqa: E731
@@ -1855,9 +2266,12 @@ async def test_streaming_iterator_hook_pipeline_releases_originals_on_runtime_to
             delivered.append(item)
 
     assert len(delivered) == 2
-    assert delivered[0].choices[0].delta.tool_calls[0].function.arguments == '{"ssn": "123"}'
+    delivered_tool_call = delivered[0].choices[0].delta.tool_calls[0]
+    assert delivered_tool_call.function.arguments == '{"ssn": "[MASKED]"}'
+    assert delivered_tool_call.function.name == "lookup"
+    assert delivered_tool_call.id == "call_1"
     assert delivered[1].choices[0].finish_reason == "tool_calls"
-    assert any("'gr-post'" in message and "discarded" in message for message in _warnings(caplog))
+    assert not any("discarded" in message for message in _warnings(caplog))
 
 
 @pytest.mark.asyncio
@@ -1965,37 +2379,97 @@ async def test_streaming_iterator_hook_pipeline_releases_stream_echoed_in_anothe
 
 
 @pytest.mark.asyncio
-async def test_streaming_iterator_hook_pipeline_releases_originals_on_unresolvable_response_shape(
+async def test_streaming_iterator_hook_skips_pipeline_and_warns_without_request_route(
     proxy_logging, make_user_api_key_auth, monkeypatch, caplog
 ):
     seen: Dict[str, Any] = {}
     monkeypatch.setattr(litellm, "callbacks", [_unified_stream_guardrail(seen)])
     monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
     data = _post_call_pipeline_data(stream=True)
-    chunks = [object(), object()]
-    delivered: List[Any] = []
+    chunks = _stream_chunks()
 
     with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
-        async for item in proxy_logging.async_post_call_streaming_iterator_hook(
-            user_api_key_dict=make_user_api_key_auth(),
-            response=_async_chunk_iter(chunks),
-            request_data=data,
-        ):
-            delivered.append(item)
+        delivered = [
+            item
+            async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+                user_api_key_dict=make_user_api_key_auth(),
+                response=_async_chunk_iter(chunks),
+                request_data=data,
+            )
+        ]
 
     assert [item is chunk for item, chunk in zip(delivered, chunks)] == [True, True]
     assert len(delivered) == 2
     assert seen.get("count") is None
-    assert any("response-governance" in message and "shape" in message for message in _warnings(caplog))
+    assert any("response-governance" in message and "route None" in message for message in _warnings(caplog))
+
+
+@pytest.mark.asyncio
+async def test_per_chunk_streaming_hook_runs_pipeline_managed_guardrail_without_request_route(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
+    seen: Dict[str, Any] = {}
+
+    class UnifiedRecordingGuardrail(CustomGuardrail):
+        async def async_post_call_streaming_hook(self, user_api_key_dict, response):
+            seen[self.guardrail_name] = seen.get(self.guardrail_name, 0) + 1
+            return None
+
+        async def apply_guardrail(self, inputs, request_data, input_type, logging_obj=None):
+            return inputs
+
+    monkeypatch.setattr(
+        litellm,
+        "callbacks",
+        [UnifiedRecordingGuardrail(guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=True)],
+    )
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    result = await proxy_logging.async_post_call_streaming_hook(
+        data=data,
+        response=_stream_chunks()[0],
+        user_api_key_dict=make_user_api_key_auth(),
+    )
+
+    assert result is not None
+    assert seen["gr-post"] == 1
 
 
 def _anthropic_sse_chunks() -> List[bytes]:
     events = [
-        ("message_start", {"type": "message_start", "message": {"id": "msg_1", "type": "message", "role": "assistant", "model": "m", "content": [], "stop_reason": None, "usage": {"input_tokens": 1, "output_tokens": 0}}}),
-        ("content_block_start", {"type": "content_block_start", "index": 0, "content_block": {"type": "text", "text": ""}}),
-        ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "text_delta", "text": "hello world"}}),
+        (
+            "message_start",
+            {
+                "type": "message_start",
+                "message": {
+                    "id": "msg_1",
+                    "type": "message",
+                    "role": "assistant",
+                    "model": "m",
+                    "content": [],
+                    "stop_reason": None,
+                    "usage": {"input_tokens": 1, "output_tokens": 0},
+                },
+            },
+        ),
+        (
+            "content_block_start",
+            {"type": "content_block_start", "index": 0, "content_block": {"type": "text", "text": ""}},
+        ),
+        (
+            "content_block_delta",
+            {"type": "content_block_delta", "index": 0, "delta": {"type": "text_delta", "text": "hello world"}},
+        ),
         ("content_block_stop", {"type": "content_block_stop", "index": 0}),
-        ("message_delta", {"type": "message_delta", "delta": {"stop_reason": "end_turn", "stop_sequence": None}, "usage": {"output_tokens": 2}}),
+        (
+            "message_delta",
+            {
+                "type": "message_delta",
+                "delta": {"stop_reason": "end_turn", "stop_sequence": None},
+                "usage": {"output_tokens": 2},
+            },
+        ),
         ("message_stop", {"type": "message_stop"}),
     ]
     return [f"event: {name}\ndata: {json.dumps(payload)}\n\n".encode() for name, payload in events]
@@ -2062,7 +2536,13 @@ async def test_streaming_iterator_hook_pipeline_delivers_text_rewrite_on_anthrop
     assert "hello [MASKED]" in raw
     assert "hello world" not in raw
     assert raw.count("event: content_block_delta") == 1
-    for expected_event in ("message_start", "content_block_start", "content_block_stop", "message_delta", "message_stop"):
+    for expected_event in (
+        "message_start",
+        "content_block_start",
+        "content_block_stop",
+        "message_delta",
+        "message_stop",
+    ):
         assert f"event: {expected_event}" in raw
 
 
@@ -2135,9 +2615,7 @@ async def test_per_chunk_streaming_hook_skips_pipeline_managed_guardrail(
     managed = UnifiedRecordingGuardrail(
         guardrail_name="gr-post", event_hook=GuardrailEventHooks.post_call, default_on=True
     )
-    free = RecordingGuardrail(
-        guardrail_name="gr-free", event_hook=GuardrailEventHooks.post_call, default_on=True
-    )
+    free = RecordingGuardrail(guardrail_name="gr-free", event_hook=GuardrailEventHooks.post_call, default_on=True)
     monkeypatch.setattr(litellm, "callbacks", [managed, free])
     monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
     data = _post_call_pipeline_data(stream=True)
@@ -2182,3 +2660,177 @@ async def test_per_chunk_streaming_hook_runs_guardrail_whose_pipeline_cannot_str
     assert result is not None
     assert seen["count"] == 1
     assert seen["response"] == "hello "
+
+
+def _mask_tool_call_arguments(inputs: Dict[str, Any]) -> Dict[str, Any]:
+    return {
+        "tool_calls": [
+            {
+                "id": stream_item_field(tool_call, "id"),
+                "type": "function",
+                "function": {
+                    "name": stream_item_field(stream_item_field(tool_call, "function"), "name"),
+                    "arguments": '{"fruit": "[MASKED]"}',
+                },
+            }
+            for tool_call in inputs.get("tool_calls", [])
+        ]
+    }
+
+
+def _anthropic_tool_use_sse_chunks() -> List[bytes]:
+    events = [
+        ("message_start", {"type": "message_start", "message": {"id": "msg_1", "type": "message", "role": "assistant", "model": "m", "content": [], "stop_reason": None, "usage": {"input_tokens": 1, "output_tokens": 0}}}),
+        ("content_block_start", {"type": "content_block_start", "index": 0, "content_block": {"type": "tool_use", "id": "toolu_1", "name": "lookup_fruit", "input": {}}}),
+        ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "input_json_delta", "partial_json": '{"fruit": "persim'}}),
+        ("content_block_delta", {"type": "content_block_delta", "index": 0, "delta": {"type": "input_json_delta", "partial_json": 'mon"}'}}),
+        ("content_block_stop", {"type": "content_block_stop", "index": 0}),
+        ("message_delta", {"type": "message_delta", "delta": {"stop_reason": "tool_use", "stop_sequence": None}, "usage": {"output_tokens": 2}}),
+        ("message_stop", {"type": "message_stop"}),
+    ]
+    return [f"event: {name}\ndata: {json.dumps(payload)}\n\n".encode() for name, payload in events]
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_pipeline_delivers_tool_use_rewrite_on_anthropic_sse(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
+    monkeypatch.setattr(litellm, "callbacks", [_rewriting_stream_guardrail(_mask_tool_call_arguments)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    delivered = [
+        item
+        async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+            user_api_key_dict=make_user_api_key_auth(request_route="/v1/messages"),
+            response=_async_chunk_iter(_anthropic_tool_use_sse_chunks()),
+            request_data=data,
+        )
+    ]
+
+    raw = b"".join(delivered).decode()
+    assert '{\\"fruit\\": \\"[MASKED]\\"}' in raw
+    assert "persim" not in raw
+    assert '"name": "lookup_fruit"' in raw and '"id": "toolu_1"' in raw
+    assert '"stop_reason": "tool_use"' in raw
+    assert raw.count("event: content_block_delta") == 2
+
+
+def _responses_function_call_events() -> List[Dict[str, Any]]:
+    def item(arguments: str, status: str) -> Dict[str, Any]:
+        return {
+            "type": "function_call",
+            "id": "fc_1",
+            "call_id": "call_1",
+            "name": "lookup_fruit",
+            "arguments": arguments,
+            "status": status,
+        }
+
+    return [
+        {"type": "response.output_item.added", "output_index": 0, "item": item("", "in_progress")},
+        {"type": "response.function_call_arguments.delta", "item_id": "fc_1", "output_index": 0, "delta": '{"fruit":'},
+        {"type": "response.function_call_arguments.delta", "item_id": "fc_1", "output_index": 0, "delta": ' "persimmon"}'},
+        {"type": "response.function_call_arguments.done", "item_id": "fc_1", "output_index": 0, "arguments": '{"fruit": "persimmon"}'},
+        {"type": "response.output_item.done", "output_index": 0, "item": item('{"fruit": "persimmon"}', "completed")},
+        {
+            "type": "response.completed",
+            "response": {"id": "resp_1", "created_at": 1, "model": "m", "output": [item('{"fruit": "persimmon"}', "completed")], "status": "completed"},
+        },
+    ]
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_pipeline_delivers_function_call_rewrite_on_responses_events(
+    proxy_logging, make_user_api_key_auth, monkeypatch
+):
+    monkeypatch.setattr(litellm, "callbacks", [_rewriting_stream_guardrail(_mask_tool_call_arguments)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    delivered = [
+        item
+        async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+            user_api_key_dict=make_user_api_key_auth(request_route="/v1/responses"),
+            response=_async_chunk_iter(_responses_function_call_events()),
+            request_data=data,
+        )
+    ]
+
+    assert [event["type"] for event in delivered] == [event["type"] for event in _responses_function_call_events()]
+    assert [event["delta"] for event in delivered if event["type"] == "response.function_call_arguments.delta"] == ['{"fruit": "[MASKED]"}', ""]
+    assert delivered[3]["arguments"] == '{"fruit": "[MASKED]"}'
+    assert delivered[4]["item"]["arguments"] == '{"fruit": "[MASKED]"}'
+    assert delivered[5]["response"]["output"][0]["arguments"] == '{"fruit": "[MASKED]"}'
+    assert "persimmon" not in json.dumps(delivered)
+
+
+def _drop_tool_calls(inputs: Dict[str, Any]) -> Dict[str, Any]:
+    return {"tool_calls": []}
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_pipeline_discards_dropped_tool_call_on_chat_chunks(
+    proxy_logging, make_user_api_key_auth, monkeypatch, caplog
+):
+    monkeypatch.setattr(litellm, "callbacks", [_rewriting_stream_guardrail(_drop_tool_calls)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        delivered = [
+            item
+            async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+                user_api_key_dict=make_user_api_key_auth(request_route="/v1/chat/completions"),
+                response=_async_chunk_iter(_tool_call_stream_chunks()),
+                request_data=data,
+            )
+        ]
+
+    assert delivered[0].choices[0].delta.tool_calls[0].function.arguments == '{"ssn": "123"}'
+    assert delivered[1].choices[0].finish_reason == "tool_calls"
+    assert any("'gr-post'" in message and "discarded" in message for message in _warnings(caplog))
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_pipeline_discards_dropped_tool_call_on_anthropic_sse(
+    proxy_logging, make_user_api_key_auth, monkeypatch, caplog
+):
+    monkeypatch.setattr(litellm, "callbacks", [_rewriting_stream_guardrail(_drop_tool_calls)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        delivered = [
+            item
+            async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+                user_api_key_dict=make_user_api_key_auth(request_route="/v1/messages"),
+                response=_async_chunk_iter(_anthropic_tool_use_sse_chunks()),
+                request_data=data,
+            )
+        ]
+
+    assert delivered == _anthropic_tool_use_sse_chunks()
+    assert any("'gr-post'" in message and "discarded" in message for message in _warnings(caplog))
+
+
+@pytest.mark.asyncio
+async def test_streaming_iterator_hook_pipeline_discards_dropped_tool_call_on_responses_events(
+    proxy_logging, make_user_api_key_auth, monkeypatch, caplog
+):
+    monkeypatch.setattr(litellm, "callbacks", [_rewriting_stream_guardrail(_drop_tool_calls)])
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None, raising=False)
+    data = _post_call_pipeline_data(stream=True)
+
+    with caplog.at_level(logging.WARNING, logger="LiteLLM Proxy"):
+        delivered = [
+            item
+            async for item in proxy_logging.async_post_call_streaming_iterator_hook(
+                user_api_key_dict=make_user_api_key_auth(request_route="/v1/responses"),
+                response=_async_chunk_iter(_responses_function_call_events()),
+                request_data=data,
+            )
+        ]
+
+    assert delivered == _responses_function_call_events()
+    assert any("'gr-post'" in message and "discarded" in message for message in _warnings(caplog))
diff --git a/tests/test_litellm/rerank_api/test_main.py b/tests/test_litellm/rerank_api/test_main.py
index 2b6cfeda2c2..0992cd9bb37 100644
--- a/tests/test_litellm/rerank_api/test_main.py
+++ b/tests/test_litellm/rerank_api/test_main.py
@@ -111,6 +111,72 @@ def test_together_rerank_honors_api_base(respx_mock: respx.MockRouter):
     assert mock_route.calls[0].request.headers["authorization"] == "Bearer fake-together-key"
 
 
+DASHSCOPE_RERANK_BODY = {
+    "object": "list",
+    "results": [{"index": 0, "relevance_score": 0.95}],
+    "model": "qwen3-rerank",
+    "id": "rerank-mock-id",
+    "usage": {"total_tokens": 10},
+}
+
+
+def test_dashscope_rerank_defaults_to_live_rerank_route(respx_mock: respx.MockRouter, monkeypatch):
+    """Regression for the dead default endpoint: get_llm_provider always returns the
+    chat base for dashscope, which used to hijack rerank onto the dead
+    /compatible-mode/v1/reranks route."""
+    monkeypatch.delenv("DASHSCOPE_API_BASE", raising=False)
+    monkeypatch.delenv("DASHSCOPE_API_BASE_RERANK", raising=False)
+
+    mock_route = respx_mock.post("https://dashscope.aliyuncs.com/compatible-api/v1/reranks")
+    mock_route.return_value = httpx.Response(200, json=DASHSCOPE_RERANK_BODY)
+
+    response = litellm.rerank(
+        model="dashscope/qwen3-rerank",
+        query=MARKER_QUERY,
+        documents=[MARKER_DOC],
+        api_key="fake-dashscope-key",
+    )
+
+    assert mock_route.called
+    assert response.results[0]["relevance_score"] == 0.95
+
+
+def test_dashscope_rerank_chat_env_base_keeps_host_and_rerank_route(respx_mock: respx.MockRouter, monkeypatch):
+    """Regression: a chat-style DASHSCOPE_API_BASE must not hijack rerank onto the
+    chat path, while its host (the region) is preserved."""
+    monkeypatch.setenv("DASHSCOPE_API_BASE", "https://dashscope-intl.aliyuncs.com/compatible-mode/v1")
+    monkeypatch.delenv("DASHSCOPE_API_BASE_RERANK", raising=False)
+
+    mock_route = respx_mock.post("https://dashscope-intl.aliyuncs.com/compatible-api/v1/reranks")
+    mock_route.return_value = httpx.Response(200, json=DASHSCOPE_RERANK_BODY)
+
+    litellm.rerank(
+        model="dashscope/qwen3-rerank",
+        query=MARKER_QUERY,
+        documents=[MARKER_DOC],
+        api_key="fake-dashscope-key",
+    )
+
+    assert mock_route.called
+
+
+def test_dashscope_rerank_explicit_api_base_wins(respx_mock: respx.MockRouter, monkeypatch):
+    monkeypatch.setenv("DASHSCOPE_API_BASE", "https://dashscope-intl.aliyuncs.com/compatible-mode/v1")
+
+    mock_route = respx_mock.post("https://custom-rerank.example/v1/reranks")
+    mock_route.return_value = httpx.Response(200, json=DASHSCOPE_RERANK_BODY)
+
+    litellm.rerank(
+        model="dashscope/qwen3-rerank",
+        query=MARKER_QUERY,
+        documents=[MARKER_DOC],
+        api_key="fake-dashscope-key",
+        api_base="https://custom-rerank.example/v1",
+    )
+
+    assert mock_route.called
+
+
 DASHSCOPE_404_BODY = {
     "error": {
         "message": "The model `does-not-exist` does not exist or you do not have access to it.",
diff --git a/tests/test_litellm/responses/litellm_completion_transformation/test_litellm_completion_responses.py b/tests/test_litellm/responses/litellm_completion_transformation/test_litellm_completion_responses.py
index 2068f10ea2d..46249e50572 100644
--- a/tests/test_litellm/responses/litellm_completion_transformation/test_litellm_completion_responses.py
+++ b/tests/test_litellm/responses/litellm_completion_transformation/test_litellm_completion_responses.py
@@ -1,4 +1,5 @@
 import json
+from typing import Final
 
 import pytest
 
@@ -1421,6 +1422,88 @@ class TestToolChoiceTransformation:
         )
         assert result == "required"
 
+    @pytest.mark.parametrize(
+        "request_tool_choice,expected",
+        [
+            ({"type": "function", "name": "run_command"}, {"type": "function", "name": "run_command"}),
+            ({"type": "function", "function": {"name": "run_command"}}, {"type": "function", "name": "run_command"}),
+            ({"type": "custom", "name": "ApplyPatch"}, {"type": "custom", "name": "ApplyPatch"}),
+            ({"type": "custom", "custom": {"name": "ApplyPatch"}}, {"type": "custom", "name": "ApplyPatch"}),
+            ({"type": "function"}, "required"),
+            ({"type": "tool"}, "required"),
+            ({"type": "auto"}, "auto"),
+            ("required", "required"),
+            ("none", "none"),
+            (None, "auto"),
+            ("any", "auto"),
+            ("run_command", "auto"),
+            ({"name": "run_command"}, "auto"),
+        ],
+    )
+    def test_transform_tool_choice_for_responses_api_response(
+        self, request_tool_choice: object, expected: str | dict[str, str]
+    ) -> None:
+        result: Final = LiteLLMCompletionResponsesConfig._transform_tool_choice_for_responses_api_response(
+            request_tool_choice
+        )
+        assert result == expected
+
+    def test_non_streamed_response_echoes_named_tool_choice_in_responses_api_shape(self) -> None:
+        chat_completion_response: Final = ModelResponse(
+            id="chatcmpl-named-tool-choice",
+            created=1748575031,
+            model="claude-haiku-4-5",
+            object="chat.completion",
+            choices=[
+                Choices(
+                    index=0,
+                    finish_reason="tool_calls",
+                    message=Message(
+                        role="assistant",
+                        content=None,
+                        tool_calls=[
+                            ChatCompletionMessageToolCall(
+                                id="call_pwd",
+                                type="function",
+                                function=Function(name="run_command", arguments='{"command":"pwd"}'),
+                            )
+                        ],
+                    ),
+                )
+            ],
+        )
+
+        responses_api_response: Final = LiteLLMCompletionResponsesConfig.transform_chat_completion_response_to_responses_api_response(
+            request_input="Run the command pwd.",
+            responses_api_request={"tool_choice": {"type": "function", "name": "run_command"}},
+            chat_completion_response=chat_completion_response,
+        )
+
+        assert responses_api_response.tool_choice == {"type": "function", "name": "run_command"}
+
+    def test_non_streamed_response_with_unrecognized_tool_choice_echoes_auto(self) -> None:
+        chat_completion_response: Final = ModelResponse(
+            id="chatcmpl-unrecognized-tool-choice",
+            created=1748575031,
+            model="claude-haiku-4-5",
+            object="chat.completion",
+            choices=[
+                Choices(
+                    index=0,
+                    finish_reason="stop",
+                    message=Message(role="assistant", content="/Users/dev"),
+                )
+            ],
+        )
+
+        responses_api_response: Final = LiteLLMCompletionResponsesConfig.transform_chat_completion_response_to_responses_api_response(
+            request_input="Run the command pwd.",
+            responses_api_request={"tool_choice": "any"},
+            chat_completion_response=chat_completion_response,
+        )
+
+        assert responses_api_response.tool_choice == "auto"
+
 
 class TestContentTypeTransformation:
     """Test content type transformation from Responses API to Chat Completion format"""
diff --git a/tests/test_litellm/responses/litellm_completion_transformation/test_streaming_iterator_transformation.py b/tests/test_litellm/responses/litellm_completion_transformation/test_streaming_iterator_transformation.py
index 719d51c11e3..850ee7ba623 100644
--- a/tests/test_litellm/responses/litellm_completion_transformation/test_streaming_iterator_transformation.py
+++ b/tests/test_litellm/responses/litellm_completion_transformation/test_streaming_iterator_transformation.py
@@ -11,6 +11,7 @@ spend tracking stores, so a follow-up previous_response_id still finds the conve
 """
 
 import json
+from typing import Final
 from unittest.mock import AsyncMock, MagicMock
 
 import pytest
@@ -628,3 +629,79 @@ def test_streamed_anthropic_tool_call_events_correlate_on_normalized_item_id():
     assert item_dones[0].item.call_id == "toolu_01AbCdEf"
     for evt in deltas + dones:
         assert evt.item_id == added[0].item.id
+
+
+def _tool_call_chunk(finish_reason: str | None = None) -> ModelResponseStream:
+    return ModelResponseStream(
+        id=CHAT_COMPLETION_ID,
+        created=1748575031,
+        model="claude-haiku-4-5",
+        object="chat.completion.chunk",
+        choices=[
+            StreamingChoices(
+                index=0,
+                delta=Delta(
+                    role="assistant",
+                    content=None,
+                    tool_calls=[
+                        {
+                            "id": "call_pwd",
+                            "type": "function",
+                            "function": {"name": "run_command", "arguments": '{"command":"pwd"}'},
+                            "index": 0,
+                        }
+                    ],
+                ),
+                finish_reason=finish_reason,
+            )
+        ],
+    )
+
+
+def test_streamed_named_tool_choice_is_echoed_in_responses_api_shape() -> None:
+    iterator: Final = LiteLLMCompletionStreamingIterator(
+        model="claude-haiku-4-5",
+        litellm_custom_stream_wrapper=_FakeStreamWrapper([_tool_call_chunk(finish_reason="tool_calls")]),
+        request_input="Run the command pwd.",
+        responses_api_request={
+            "tools": [{"type": "function", "name": "run_command", "parameters": {"type": "object"}}],
+            "tool_choice": {"type": "function", "name": "run_command"},
+        },
+        custom_llm_provider="anthropic",
+        litellm_metadata={},
+    )
+
+    events: Final = list(iterator)
+
+    response_events: Final = [event for event in events if getattr(event, "type", None) in RESPONSE_ID_EVENT_TYPES]
+    assert [event.type for event in response_events] == [
+        "response.created",
+        "response.in_progress",
+        "response.completed",
+    ]
+    assert [event.response.tool_choice for event in response_events] == [
+        {"type": "function", "name": "run_command"},
+        {"type": "function", "name": "run_command"},
+        {"type": "function", "name": "run_command"},
+    ]
+    assert any(getattr(event, "type", None) == "response.output_item.done" for event in events)
+
+
+def test_streamed_unrecognized_tool_choice_is_echoed_as_auto() -> None:
+    iterator: Final = LiteLLMCompletionStreamingIterator(
+        model="claude-haiku-4-5",
+        litellm_custom_stream_wrapper=_FakeStreamWrapper([_tool_call_chunk(finish_reason="tool_calls")]),
+        request_input="Run the command pwd.",
+        responses_api_request={
+            "tools": [{"type": "function", "name": "run_command", "parameters": {"type": "object"}}],
+            "tool_choice": "any",
+        },
+        custom_llm_provider="anthropic",
+        litellm_metadata={},
+    )
+
+    response_events: Final = [
+        event for event in iterator if getattr(event, "type", None) in RESPONSE_ID_EVENT_TYPES
+    ]
+
+    assert [event.response.tool_choice for event in response_events] == ["auto", "auto", "auto"]
diff --git a/tests/test_litellm/responses/test_responses_api_bridge_flag.py b/tests/test_litellm/responses/test_responses_api_bridge_flag.py
index 57aa2a6baa2..ed44a9f4545 100644
--- a/tests/test_litellm/responses/test_responses_api_bridge_flag.py
+++ b/tests/test_litellm/responses/test_responses_api_bridge_flag.py
@@ -7,10 +7,14 @@ calls so routed requests do not hit a custom api_base /v1/responses endpoint.
 """
 
 from importlib import import_module
+from typing import Final
 from unittest.mock import MagicMock, patch
 
+import httpx
+import pytest
 
 import litellm
+from litellm.llms.custom_httpx.http_handler import HTTPHandler
 from litellm.types.llms.openai import ResponseAPIUsage, ResponsesAPIResponse
 from litellm.types.utils import Choices, Message, ModelResponse, Usage
 
@@ -18,6 +22,26 @@ from litellm.types.utils import Choices, Message, ModelResponse, Usage
 class TestUseResponsesApiBridgeFlag:
     """Test that bridge opt-in forces the chat completions path."""
 
+    @pytest.mark.parametrize("model", ["openai/chat_completions/gpt-6-astra", "xai/test-classifier"])
+    def test_encrypted_classifier_rejection_preserves_public_error(self, model: str) -> None:
+        respond: Final = MagicMock(side_effect=AssertionError("Incompatible classifier sent an upstream request"))
+        with httpx.Client(transport=httpx.MockTransport(respond)) as client:
+            with pytest.raises(
+                litellm.APIConnectionError,
+                match="Encrypted task classification requires a compatible native Responses deployment",
+            ) as error:
+                litellm.responses(
+                    model=model,
+                    input="Delegated task",
+                    api_key="test-key",
+                    api_base="https://classifier.test/v1",
+                    client=HTTPHandler(client=client),
+                    _require_encrypted_task_support=True,
+                    num_retries=0,
+                )
+        assert error.value.status_code == 500
+        respond.assert_not_called()
+
     @patch.object(
         import_module("litellm.responses.main").litellm_completion_transformation_handler, "response_api_handler"
     )
diff --git a/tests/test_litellm/responses/test_streaming_iterator.py b/tests/test_litellm/responses/test_streaming_iterator.py
index c226c0b4d09..5e0e794d93e 100644
--- a/tests/test_litellm/responses/test_streaming_iterator.py
+++ b/tests/test_litellm/responses/test_streaming_iterator.py
@@ -18,6 +18,7 @@ from litellm.responses.streaming_iterator import (
     SyncResponsesAPIStreamingIterator,
 )
 from litellm.types.llms.openai import (
+    ResponseAPIUsage,
     ResponseCompletedEvent,
     ResponsesAPIResponse,
     ResponsesAPIStreamEvents,
@@ -329,8 +330,6 @@ def test_run_post_success_hooks_does_not_report_generation_time_as_overhead():
 
 
 def _responses_api_response_with_usage() -> ResponsesAPIResponse:
-    from litellm.types.llms.openai import ResponseAPIUsage
-
     return ResponsesAPIResponse(
         id="resp_lit6427",
         created_at=int(datetime(2025, 1, 1).timestamp()),
@@ -368,6 +367,53 @@ def test_stamp_responses_usage_cost_keeps_provider_reported_cost():
     logging_obj._response_cost_calculator.assert_not_called()
 
 
+def _unvalidated_response_with_dict_usage(usage: dict) -> ResponsesAPIResponse:
+    return ResponsesAPIResponse.model_construct(
+        id="resp_lit7391",
+        created_at=int(datetime(2025, 1, 1).timestamp()),
+        status="completed",
+        model="perplexity/deepseek-v4-flash-0731",
+        object="response",
+        output=[],
+        truncation="",
+        usage=usage,
+    )
+
+
+def test_stamp_responses_usage_cost_keeps_provider_cost_from_dict_usage():
+    from litellm.responses.streaming_iterator import _stamp_responses_usage_cost
+    response = _unvalidated_response_with_dict_usage(
+        {
+            "input_tokens": 29,
+            "output_tokens": 120,
+            "output_tokens_details": {"reasoning_tokens": 117},
+            "total_tokens": 149,
+            "cost": {"currency": "USD", "input_cost": 0, "output_cost": 3e-05, "total_cost": 3e-05},
+        }
+    )
+    logging_obj = Mock(spec=LiteLLMLoggingObj)
+
+    _stamp_responses_usage_cost(response, logging_obj)
+
+    assert isinstance(response.usage, ResponseAPIUsage)
+    assert response.usage.cost == pytest.approx(3e-05)
+    assert response.usage.output_tokens_details.reasoning_tokens == 117
+    logging_obj._response_cost_calculator.assert_not_called()
+
+
+def test_stamp_responses_usage_cost_computes_cost_for_dict_usage_without_cost():
+    from litellm.responses.streaming_iterator import _stamp_responses_usage_cost
+    response = _unvalidated_response_with_dict_usage({"input_tokens": 29, "output_tokens": 120, "total_tokens": 149})
+    logging_obj = Mock(spec=LiteLLMLoggingObj)
+    logging_obj._response_cost_calculator.return_value = 0.000704
+
+    _stamp_responses_usage_cost(response, logging_obj)
+
+    assert isinstance(response.usage, ResponseAPIUsage)
+    assert response.usage.cost == pytest.approx(0.000704)
+    logging_obj._response_cost_calculator.assert_called_once_with(result=response)
+
+
 def test_stamp_responses_usage_cost_survives_calculator_failure():
     from litellm.responses.streaming_iterator import _stamp_responses_usage_cost
 
@@ -535,5 +581,50 @@ async def test_streaming_logging_copy_fallback_leaves_caller_event_untouched():
     with patch.object(type(iterator.completed_response), "model_dump", side_effect=ValueError("cannot serialize")):
         iterator._log_completed_response(is_async=True)
 
-    assert logged == [iterator.completed_response]
+    assert len(logged) == 1
+    assert logged[0] is not iterator.completed_response
+    assert logged[0].response is not iterator.completed_response.response
+    assert logged[0].response._hidden_params["headers"]["apim-request-id"] == "azure-correlation-1"
     assert iterator.completed_response.response._hidden_params == {}
+
+
+def _unvalidated_completed_config() -> Mock:
+    """Config whose completed event carries a Perplexity-style response that fails validation
+    (``truncation: ""``) and already holds the stamped ``ResponseAPIUsage``."""
+    mock_config = Mock(spec=BaseResponsesAPIConfig)
+
+    def _transform(model, parsed_chunk, logging_obj):
+        response = _unvalidated_response_with_dict_usage(
+            ResponseAPIUsage(input_tokens=29, output_tokens=373, total_tokens=402, cost={"total_cost": 0.0001})
+        )
+        return ResponseCompletedEvent(type=ResponsesAPIStreamEvents.RESPONSE_COMPLETED, response=response)
+
+    mock_config.transform_streaming_response.side_effect = _transform
+    return mock_config
+
+
+@pytest.mark.asyncio
+async def test_streaming_logging_copy_keeps_client_usage_when_response_fails_validation():
+    """LIT-7391: the logging copy cannot round-trip a response that fails validation, and logging
+    rewrites the assembled response's usage to chat shape in place, so the event handed to logging
+    must never be the one the caller receives."""
+    logging_obj = _logging_obj_stub()
+    logging_obj.stream = True
+    logged: list[object] = []
+    logging_obj.dispatch_success_handlers = _capture_dispatch(logged)
+    logging_obj._on_deferred_stream_complete = None
+
+    iterator = _make_header_iterator(headers={}, config=_unvalidated_completed_config(), logging_obj=logging_obj)
+    events = [event async for event in iterator]
+
+    assert len(logged) == 1
+    now = datetime.now()
+    LiteLLMLoggingObj._get_assembled_streaming_response(
+        logging_obj, logged[0], start_time=now, end_time=now, is_async=True, streaming_chunks=[]
+    )
+    assert logged[0].response.usage["prompt_tokens"] == 29
+
+    client_usage = events[-1].response.usage
+    assert isinstance(client_usage, ResponseAPIUsage)
+    assert client_usage.input_tokens == 29
+    assert client_usage.cost == pytest.approx(0.0001)
diff --git a/tests/test_litellm/router_strategy/test_base_routing_strategy.py b/tests/test_litellm/router_strategy/test_base_routing_strategy.py
index 154042692d0..dc75c3d2916 100644
--- a/tests/test_litellm/router_strategy/test_base_routing_strategy.py
+++ b/tests/test_litellm/router_strategy/test_base_routing_strategy.py
@@ -1,4 +1,5 @@
 import json
+import logging
 from typing import Any, Dict, List, Optional, Set, Union
 
 import pytest
@@ -9,7 +10,7 @@ from unittest.mock import MagicMock, patch
 
 
 from litellm.caching.caching import DualCache
-from litellm.caching.redis_cache import RedisPipelineIncrementOperation
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError, RedisPipelineIncrementOperation
 from litellm.router_strategy.base_routing_strategy import BaseRoutingStrategy
 
 
@@ -146,3 +147,18 @@ async def test_cache_keys_management(base_strategy):
     # Test resetting cache keys
     base_strategy.reset_in_memory_keys_to_update()
     assert len(base_strategy.get_in_memory_keys_to_update()) == 0
+
+
+@pytest.mark.asyncio
+async def test_push_refused_by_the_open_circuit_breaker_is_not_logged_as_an_error(base_strategy, mock_dual_cache, caplog):
+    """The sync loop pushes every 100 ms under usage-based routing, so an open breaker must not add an error line per cycle."""
+    mock_dual_cache.redis_cache.async_increment_pipeline.side_effect = RedisCircuitBreakerOpenError(
+        "Redis circuit breaker is open - skipping async_increment_pipeline"
+    )
+    base_strategy.redis_increment_operation_queue = [{"key": "k", "increment_value": 1.0, "ttl": 60}]
+
+    with caplog.at_level(logging.ERROR):
+        await base_strategy._push_in_memory_increments_to_redis()
+
+    assert caplog.records == []
+    assert base_strategy.redis_increment_operation_queue == []
diff --git a/tests/test_litellm/router_strategy/test_budget_limiter_hotpath.py b/tests/test_litellm/router_strategy/test_budget_limiter_hotpath.py
index 36fa38bacb5..4cc8fe78811 100644
--- a/tests/test_litellm/router_strategy/test_budget_limiter_hotpath.py
+++ b/tests/test_litellm/router_strategy/test_budget_limiter_hotpath.py
@@ -1,7 +1,13 @@
+import asyncio
+import gc
+import logging
+from unittest.mock import AsyncMock, MagicMock
+
 import pytest
 
 import litellm
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import RedisCache, RedisCircuitBreakerOpenError
 from litellm.router_strategy.budget_limiter import RouterBudgetLimiting
 from litellm.types.router import LiteLLM_Params
 from litellm.types.utils import BudgetConfig
@@ -303,3 +309,90 @@ def test_router_add_deployment_registers_deployment_budget(
     )
     assert config is not None
     assert config.max_budget == 0.000000000001
+
+
+@pytest.mark.asyncio
+async def test_sync_refused_by_the_open_circuit_breaker_is_quiet_and_leaks_no_task(disable_budget_sync, caplog):
+    """The budget sync runs every second, so an open breaker must not add an error line or an unretrieved task exception per cycle."""
+    refused = RedisCircuitBreakerOpenError("Redis circuit breaker is open - skipping async_increment_pipeline")
+    redis_cache = MagicMock(spec=RedisCache)
+    redis_cache.async_increment_pipeline = AsyncMock(side_effect=refused)
+    redis_cache.async_batch_get_cache = AsyncMock(side_effect=refused)
+    limiter = RouterBudgetLimiting(
+        dual_cache=DualCache(redis_cache=redis_cache),
+        provider_budget_config={"openai": BudgetConfig(max_budget=1.0, budget_duration="1d")},
+    )
+    await asyncio.gather(*(task for task in asyncio.all_tasks() if task is not asyncio.current_task()))
+    limiter.redis_increment_operation_queue = [{"key": "provider_spend:openai:1d", "increment_value": 0.5, "ttl": 60}]
+    loop = asyncio.get_running_loop()
+    unretrieved = MagicMock()
+    loop.set_exception_handler(unretrieved)
+
+    try:
+        with caplog.at_level(logging.ERROR):
+            await limiter._sync_in_memory_spend_with_redis()
+            await asyncio.sleep(0)
+            gc.collect()
+    finally:
+        loop.set_exception_handler(None)
+
+    assert caplog.records == []
+    unretrieved.assert_not_called()
+    assert limiter.redis_increment_operation_queue == []
+    assert redis_cache.async_increment_pipeline.await_count == 1
+
+
+async def _limiter_with_redis(redis_cache: MagicMock) -> RouterBudgetLimiting:
+    limiter = RouterBudgetLimiting(
+        dual_cache=DualCache(redis_cache=redis_cache),
+        provider_budget_config={"openai": BudgetConfig(max_budget=1.0, budget_duration="1d")},
+    )
+    await asyncio.gather(*(task for task in asyncio.all_tasks() if task is not asyncio.current_task()))
+    limiter.redis_increment_operation_queue = [{"key": "provider_spend:openai:1d", "increment_value": 0.5, "ttl": 60}]
+    return limiter
+
+
+@pytest.mark.asyncio
+async def test_push_returns_before_redis_answers(disable_budget_sync):
+    """The push runs inside the request success callback, so it must hand the Redis round trip to a task instead of waiting on it."""
+    redis_answered = asyncio.Event()
+
+    async def wait_for_redis(**_: object) -> None:
+        await redis_answered.wait()
+
+    redis_cache = MagicMock(spec=RedisCache)
+    redis_cache.async_increment_pipeline = AsyncMock(side_effect=wait_for_redis)
+    limiter = await _limiter_with_redis(redis_cache)
+
+    await asyncio.wait_for(limiter._push_in_memory_increments_to_redis(), timeout=1)
+    await asyncio.sleep(0)
+
+    assert not redis_answered.is_set()
+    assert redis_cache.async_increment_pipeline.await_count == 1
+    assert limiter.redis_increment_operation_queue == []
+    redis_answered.set()
+    await asyncio.gather(*(task for task in asyncio.all_tasks() if task is not asyncio.current_task()))
+
+
+@pytest.mark.asyncio
+async def test_push_task_failure_is_logged_once_and_not_leaked(disable_budget_sync, caplog):
+    """A real Redis failure on the background push must surface as one error line, never as an unretrieved task exception."""
+    redis_cache = MagicMock(spec=RedisCache)
+    redis_cache.async_increment_pipeline = AsyncMock(side_effect=ConnectionError("Error 61 connecting to 127.0.0.1:6379"))
+    limiter = await _limiter_with_redis(redis_cache)
+    loop = asyncio.get_running_loop()
+    unretrieved = MagicMock()
+    loop.set_exception_handler(unretrieved)
+
+    try:
+        with caplog.at_level(logging.ERROR):
+            await limiter._push_in_memory_increments_to_redis()
+            await asyncio.sleep(0)
+            gc.collect()
+    finally:
+        loop.set_exception_handler(None)
+
+    assert [record.getMessage() for record in caplog.records] == [
+        "Error syncing in-memory cache with Redis: Error 61 connecting to 127.0.0.1:6379"
+    ]
+    unretrieved.assert_not_called()
diff --git a/tests/test_litellm/router_strategy/test_complexity_router.py b/tests/test_litellm/router_strategy/test_complexity_router.py
index 9f925499f1a..dddaee71a63 100644
--- a/tests/test_litellm/router_strategy/test_complexity_router.py
+++ b/tests/test_litellm/router_strategy/test_complexity_router.py
@@ -5,6 +5,10 @@ Tests the rule-based complexity scoring and tier assignment logic.
 """
 
 import asyncio
+from collections.abc import AsyncIterator
+import json
+from copy import deepcopy
+from functools import partial
 import logging
 import sys
 import time
@@ -12,6 +16,7 @@ from typing import Dict, Final, List
 from unittest.mock import AsyncMock, MagicMock, patch
 
 import pytest
+import httpx
 from pydantic import ValidationError
 
 import litellm
@@ -66,6 +71,8 @@ from litellm.types.router import (
     LiteLLM_Params,
     TaggedPreRoutingStrategy,
 )
+from litellm.types.llms.openai import ResponsesAPIResponse
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
 
 
 requires_semantic_router = pytest.mark.skipif(
@@ -194,7 +201,14 @@ class TestComplexityRouterInit:
             complexity_router_config=basic_config,
         )
 
-        assert router._reminder_markers == (("<system-reminder>", "</system-reminder>"),)
+        from litellm.router_strategy.complexity_router.complexity_router import _extract_current_ask_and_system_prompt
+
+        assert (
+            _extract_current_ask_and_system_prompt(
+                [{"role": "user", "content": "<system-reminder>noise</system-reminder>hello"}], router._reminder_markers
+            )[0]
+            == "hello"
+        )
 
     def test_init_without_config(self, mock_router_instance):
         """Test initialization without configuration uses defaults."""
@@ -2482,6 +2496,366 @@ class TestTierLabels:
         assert set(config.tier_boundaries) == {"simple_medium", "medium_complex", "complex_reasoning"}
 
 
+def _encrypted_agent_task() -> dict[str, object]:
+    return {
+        "type": "agent_message",
+        "author": "/root",
+        "recipient": "/root/child",
+        "content": [
+            {"type": "input_text", "text": "Message Type: NEW_TASK\nTask name: /root/child\nPayload:\nHello"},
+            {"type": "encrypted_content", "encrypted_content": "opaque-provider-task"},
+        ],
+    }
+
+
+def _native_classifier_response(content: str) -> ResponsesAPIResponse:
+    response: Final = ResponsesAPIResponse(
+        id="resp_classifier",
+        created_at=0,
+        status="completed",
+        output=[{"type": "message", "role": "assistant", "content": [{"type": "output_text", "text": content}]}],
+    )
+    response._hidden_params = {"response_cost": 0.0001}
+    return response
+
+
+def _native_classifier_router(
+    output: str = '{"tier":"REASONING"}',
+    classifier_type: str = "llm",
+    deployment_model: str = "openai/gpt-6-astra",
+    failure: Exception | None = None,
+    native_router: Router | None = None,
+    http_handler: AsyncHTTPHandler | None = None,
+) -> tuple[ComplexityRouter, MagicMock]:
+    dependency: Final = MagicMock(
+        aresponses=(
+            native_router.factory_function(partial(litellm.aresponses, client=http_handler), call_type="aresponses")
+            if native_router is not None
+            else AsyncMock(return_value=_native_classifier_response(output), side_effect=failure)
+        ),
+        acompletion=AsyncMock(return_value=_llm_response('{"tier":"SIMPLE"}')),
+        get_model_list=(
+            native_router.get_model_list
+            if native_router is not None
+            else MagicMock(return_value=[{"litellm_params": {"model": deployment_model}}])
+        ),
+    )
+    return (
+        ComplexityRouter(
+            model_name="encrypted-router",
+            litellm_router_instance=dependency,
+            complexity_router_config={
+                "tiers": {"SIMPLE": "cheap-model", "REASONING": "deep-model"},
+                "classifier_type": classifier_type,
+                "classifier_llm_config": {
+                    "model": "classifier",
+                    "timeout_ms": 5000 if native_router is not None else 100,
+                    "reasoning_effort": "low",
+                },
+                "heuristic_first_max_tier": "SIMPLE" if classifier_type == "heuristic_first" else None,
+                "hybrid_boundary_margin": 0.01 if classifier_type == "hybrid" else None,
+                "classifier_fallback": "default_model",
+                "default_model": "deep-model",
+                "session_affinity": False,
+                "deployment_affinity": False,
+            },
+        ),
+        dependency,
+    )
+
+
+@pytest.fixture
+async def native_classifier_http() -> AsyncIterator[tuple[AsyncHTTPHandler, MagicMock]]:
+    respond: Final = MagicMock(
+        return_value=httpx.Response(200, json=_native_classifier_response('{"tier":"REASONING"}').model_dump())
+    )
+    async with httpx.AsyncClient(transport=httpx.MockTransport(respond)) as client:
+        handler: Final = AsyncHTTPHandler()
+        await handler.client.aclose()
+        handler.client = client
+        yield handler, respond
+
+
+class TestEncryptedTaskClassifier:
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("classifier_type", ["llm", "heuristic_first", "hybrid"])
+    @pytest.mark.parametrize("codex", [True, False])
+    @pytest.mark.parametrize(
+        "reminder",
+        [
+            "<environment_context>cwd=/repo</environment_context>",
+            "<user_instructions>Keep answers concise</user_instructions>",
+        ],
+    )
+    async def test_encrypted_task_detection_uses_request_reminder_markers(
+        self, classifier_type: str, codex: bool, reminder: str
+    ):
+        router, dependency = _native_classifier_router(classifier_type=classifier_type)
+        task: Final = _encrypted_agent_task()
+        request: Final = {
+            "input": [task, {"role": "user", "content": reminder}],
+            "metadata": {"user_agent": "codex-tui" if codex else "curl/8.7.1"},
+        }
+        original: Final = deepcopy(request)
+
+        result: Final = await router.async_pre_routing_hook(model="encrypted-router", request_kwargs=request)
+
+        assert request == original
+        assert result.model == ("deep-model" if codex else "cheap-model")
+        if codex:
+            assert result.routing_decision["cause"] == "llm_classifier"
+            assert result.routing_decision["tier"] == "REASONING"
+            dependency.aresponses.assert_awaited_once()
+            assert dependency.aresponses.call_args.kwargs["input"][-1] == task
+            dependency.acompletion.assert_not_called()
+        else:
+            dependency.aresponses.assert_not_called()
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("classifier_type", ["llm", "heuristic_first", "hybrid"])
+    @pytest.mark.parametrize("tier,model", [("SIMPLE", "cheap-model"), ("REASONING", "deep-model")])
+    async def test_encrypted_task_routes_by_native_verdict(self, classifier_type: str, tier: str, model: str):
+        router, dependency = _native_classifier_router(json.dumps({"tier": tier}), classifier_type)
+        task: Final = _encrypted_agent_task()
+        request: Final = {
+            "input": [
+                {"role": "user", "content": "Prior task context"},
+                task,
+                {"type": "function_call_output", "call_id": "call_1", "output": "Tool output"},
+                {"role": "user", "content": "<system-reminder>Injected reminder</system-reminder>"},
+            ],
+            "instructions": "Caller constraints",
+            "proxy_server_request": {"body": {"input": [task], "metadata": {"authorization": "source-secret"}}},
+            "tools": [{"type": "function", "name": "execute"}],
+            "previous_response_id": "resp_parent",
+            "litellm_session_id": "parent-session",
+            "litellm_trace_id": "parent-trace",
+            "turn_off_message_logging": True,
+            "litellm_metadata": {"user_api_key_hash": "caller-key-hash"},
+        }
+        original: Final = deepcopy(request)
+
+        result: Final = await router.async_pre_routing_hook(model="encrypted-router", request_kwargs=request)
+
+        assert result.model == model
+        assert result.routing_decision["tier"] == tier
+        assert result.routing_decision["cause"] == "llm_classifier"
+        assert result.routing_decision["classifier_cost"] == 0.0001
+        assert result.messages is None
+        assert request == original
+        dependency.acompletion.assert_not_called()
+        call: Final = dependency.aresponses.call_args.kwargs
+        assert call["input"][-1] == task
+        assert "opaque-provider-task" not in json.dumps(call["input"][:-1])
+        assert "Prior task context" in json.dumps(call["input"][:-1])
+        assert "Caller constraints" in json.dumps(call["input"][:-1])
+        assert "Caller constraints" not in call["instructions"]
+        assert "SIMPLE" in call["instructions"] and "REASONING" in call["instructions"]
+        assert call["text"]["format"]["schema"]["properties"]["tier"]["enum"] == [
+            "SIMPLE",
+            "MEDIUM",
+            "COMPLEX",
+            "REASONING",
+        ]
+        assert call["text"]["format"]["strict"] is True
+        assert call["reasoning"] == {"effort": "low"}
+        assert call["store"] is False
+        assert call["_require_encrypted_task_support"] is True
+        assert call["stream"] is False
+        assert "tools" not in call and "previous_response_id" not in call
+        assert "messages" not in call and "response_format" not in call
+        assert call["timeout"] == 0.1 and call["num_retries"] == 0 and call["disable_fallbacks"] is True
+        assert call["litellm_session_id"] == "parent-session"
+        assert call["litellm_trace_id"] == "parent-trace"
+        assert call["turn_off_message_logging"] is True
+        assert call["metadata"]["user_api_key_hash"] == "caller-key-hash"
+        assert call["proxy_server_request"]["body"]["input"] == call["input"]
+        assert call["proxy_server_request"]["originating_request_masked"] == {
+            "input": [task], "metadata": {"authorization": "REDACTED"},
+        }
+        assert "source-secret" not in json.dumps(call)
+        assert "originating_request_masked" not in call["proxy_server_request"]["body"]
+
+    @pytest.mark.asyncio
+    async def test_claude_code_encrypted_task_omits_caller_instructions(self):
+        router, dependency = _native_classifier_router()
+        task: Final = _encrypted_agent_task()
+        request: Final = {
+            "input": [task],
+            "instructions": "CLAUDE_CODE_SYSTEM",
+            "litellm_metadata": {"user_agent": "claude-cli/2.1.233"},
+        }
+        original: Final = deepcopy(request)
+
+        result: Final = await router.async_pre_routing_hook(model="encrypted-router", request_kwargs=request)
+
+        assert result.routing_decision["cause"] == "llm_classifier"
+        assert request == original
+        call: Final = dependency.aresponses.call_args.kwargs
+        assert call["instructions"] == classification_system_prompt(router.config.classifier_context_window_size)
+        assert "CLAUDE_CODE_SYSTEM" not in json.dumps(call["input"][:-1])
+        assert call["input"][-1] == task
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        "items",
+        [
+            [
+                {"type": "reasoning", "encrypted_content": "opaque-history", "summary": []},
+                {"role": "user", "content": "hi"},
+            ],
+            [_encrypted_agent_task(), {"role": "user", "content": "hi"}],
+            [{**_encrypted_agent_task(), "content": [{"type": "input_text", "text": "hi"}]}],
+            [{"role": "user", "content": "gAAAA is plain text"}],
+            [
+                {"role": "user", "content": "hi"},
+                {"type": "function_call_output", "call_id": "call_1", "output": "opaque-provider-task"},
+            ],
+        ],
+        ids=[
+            "historical-reasoning",
+            "older-encrypted-task",
+            "plaintext-agent",
+            "ciphertext-looking-text",
+            "tool-output",
+        ],
+    )
+    async def test_other_asks_keep_chat_classifier(self, items: list[dict[str, object]]):
+        router, dependency = _native_classifier_router()
+
+        result: Final = await router.async_pre_routing_hook(model="encrypted-router", request_kwargs={"input": items})
+
+        assert result.model == "cheap-model"
+        assert result.routing_decision["cause"] == "llm_classifier"
+        dependency.aresponses.assert_not_called()
+        dependency.acompletion.assert_awaited_once()
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("output", ["", "not-json", '{"tier":"UNKNOWN"}'])
+    async def test_invalid_native_verdict_uses_existing_fallback(self, output: str):
+        router, dependency = _native_classifier_router(output=output)
+
+        result: Final = await router.async_pre_routing_hook(
+            model="encrypted-router", request_kwargs={"input": [_encrypted_agent_task()]}
+        )
+
+        assert result.model == "deep-model"
+        assert result.routing_decision["cause"] == "default_model_fallback"
+        dependency.aresponses.assert_awaited_once()
+        dependency.acompletion.assert_not_called()
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        "deployment_model",
+        ["anthropic/test-classifier", "openai/chat_completions/gpt-6-astra", "xai/test-classifier"],
+    )
+    async def test_incompatible_classifier_does_not_flatten_encryption(
+        self, deployment_model: str, native_classifier_http: tuple[AsyncHTTPHandler, MagicMock]
+    ):
+        handler, respond = native_classifier_http
+        native: Final = Router(
+            model_list=[
+                {
+                    "model_name": "classifier",
+                    "litellm_params": {
+                        "model": deployment_model,
+                        "api_key": "test-key",
+                        "api_base": "https://classifier.test/v1",
+                    },
+                }
+            ],
+            num_retries=0,
+        )
+        router, _ = _native_classifier_router(native_router=native, http_handler=handler)
+
+        result: Final = await router.async_pre_routing_hook(
+            model="encrypted-router", request_kwargs={"input": [_encrypted_agent_task()]}
+        )
+
+        assert result.model == "deep-model"
+        assert result.routing_decision["cause"] == "default_model_fallback"
+        respond.assert_not_called()
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("blocked", [True, False])
+    async def test_native_classifier_validates_selected_deployment(
+        self, blocked: bool, native_classifier_http: tuple[AsyncHTTPHandler, MagicMock]
+    ):
+        handler, respond = native_classifier_http
+        native: Final = Router(
+            model_list=[
+                {
+                    "model_name": "classifier",
+                    "litellm_params": {"model": "anthropic/test-classifier", "api_key": "test-key", "order": 0},
+                    "model_info": {"id": "incompatible", "blocked": blocked},
+                },
+                {
+                    "model_name": "classifier",
+                    "litellm_params": {
+                        "model": "openai/gpt-6-astra",
+                        "api_key": "test-key",
+                        "order": 1,
+                        "api_base": "https://classifier.test/v1",
+                    },
+                    "model_info": {"id": "compatible"},
+                },
+            ],
+            num_retries=0,
+        )
+        router, _ = _native_classifier_router(native_router=native, http_handler=handler)
+        task: Final = _encrypted_agent_task()
+
+        result: Final = await router.async_pre_routing_hook(model="encrypted-router", request_kwargs={"input": [task]})
+
+        assert result.model == "deep-model"
+        assert result.routing_decision["cause"] == ("llm_classifier" if blocked else "default_model_fallback")
+        if blocked:
+            respond.assert_called_once()
+            request: Final = respond.call_args.args[0]
+            assert request.url.path == "/v1/responses"
+            body: Final = json.loads(request.content)
+            assert body["input"][-1] == task
+            assert "_require_encrypted_task_support" not in body
+        else:
+            respond.assert_not_called()
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("classifier_type", ["llm", "heuristic_first", "hybrid"])
+    @pytest.mark.parametrize(
+        "input_items",
+        [
+            ["unsupported-input-item"],
+            [{**_encrypted_agent_task(), "content": [{"type": "input_text", "text": "hi"}, None]}],
+        ],
+    )
+    async def test_encrypted_detection_does_not_reject_other_input_shapes(
+        self, classifier_type: str, input_items: list[object]
+    ):
+        router, dependency = _native_classifier_router(classifier_type=classifier_type)
+
+        result: Final = await router.aclassify("hi", request_kwargs={"input": input_items})
+
+        assert result.cause != "default_model_fallback"
+        assert result.tier == ComplexityTier.SIMPLE
+        dependency.aresponses.assert_not_called()
+        if classifier_type == "llm":
+            dependency.acompletion.assert_awaited_once()
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("failure", [ValueError("invalid_encrypted_content"), TimeoutError("classifier timed out")])
+    async def test_native_provider_failure_uses_existing_fallback(self, failure: Exception):
+        router, dependency = _native_classifier_router(failure=failure)
+
+        result: Final = await router.async_pre_routing_hook(
+            model="encrypted-router", request_kwargs={"input": [_encrypted_agent_task()]}
+        )
+
+        assert result.model == "deep-model"
+        assert result.routing_decision["cause"] == "default_model_fallback"
+        dependency.aresponses.assert_awaited_once()
+        dependency.acompletion.assert_not_called()
+
+
 class TestLLMClassifier:
     """Test the LLM-based classifier path (aclassify) and its fallback behavior."""
 
@@ -2940,6 +3314,29 @@ class TestLLMClassifier:
             "REASONING",
         ]
 
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("source_body", [
+        {"model": "router", "messages": [{"role": "user", "content": "source-only"}]},
+        {"model": "router", "system": "source-only", "messages": [{"role": "user", "content": "ask"}]},
+        {"model": "router", "instructions": "source-only", "input": "ask"},
+    ])
+    async def test_classifier_source_is_masked_and_separate_from_provider_input(
+        self, llm_complexity_router, mock_router_instance, source_body
+    ):
+        mock_router_instance.acompletion = AsyncMock(return_value=_llm_response('{"tier": "SIMPLE"}'))
+        outcome = await llm_complexity_router.aclassify(
+            "classify-this-ask", request_kwargs={"proxy_server_request": {
+                "body": {**source_body, "metadata": {"authorization": "source-secret"}}
+            }}
+        )
+        assert outcome.cause == "llm_classifier"
+        call_kwargs = mock_router_instance.acompletion.call_args.kwargs
+        source = call_kwargs["proxy_server_request"]["originating_request_masked"]
+        assert source == {**source_body, "metadata": {"authorization": "REDACTED"}}
+        assert "source-only" not in str(call_kwargs["messages"])
+        assert "source-only" not in str(call_kwargs["proxy_server_request"]["body"])
+        assert "classify-this-ask" in str(call_kwargs["messages"])
+
     @pytest.mark.asyncio
     @pytest.mark.parametrize("reasoning_effort", [None, "none", "low"], ids=["omitted", "none", "low"])
     async def test_classifier_reasoning_effort_reaches_only_classifier_call(
@@ -3846,11 +4243,11 @@ class TestRouterPreRoutingSharedAliasName:
     def test_forwardable_alias_marker_params_reads_the_marker_entry_only(self):
         router = Router(model_list=[self._plain_entry(), self._marker_entry(), self._tier_entry()])
 
-        forwarded = dict(router._forwardable_alias_marker_params(model="gpt4o", strategy_tags=()))
+        forwarded = dict(router._forwardable_alias_marker_params(model="gpt4o", strategy_tags=(), request_kwargs={}))
 
         assert forwarded["drop_params"] is True
         assert "api_key" not in forwarded and "api_base" not in forwarded
-        assert router._forwardable_alias_marker_params(model="gemini-flash", strategy_tags=()) == ()
+        assert router._forwardable_alias_marker_params(model="gemini-flash", strategy_tags=(), request_kwargs={}) == ()
 
     @staticmethod
     def _region_marker_entry() -> dict:
@@ -7601,11 +7998,382 @@ _ASKED = {"role": "user", "content": _ASK}
 _ANSWERED = {"role": "assistant", "content": "Working on it."}
 _TOOL_RESULT = {"type": "tool_result", "tool_use_id": "x", "content": "out"}
 _REMINDER = "<system-reminder>Budget: 42 tokens remaining. Do not mention this.</system-reminder>"
+_CODEX_NEW_TASK: Final = (
+    "Message Type: NEW_TASK\nTask name: /root/cache_worker\nSender: /root\nPayload:\n"
+    "Implement and test a thread-safe bounded LRU cache."
+)
+_CODEX_ENVELOPES: Final = (
+    "<environment_context>LITELLM ESCALATE cwd=/repo</environment_context>",
+    "<recommended_plugins>LITELLM ESCALATE plugin list</recommended_plugins>",
+    "<user_instructions>LITELLM ESCALATE preferences</user_instructions>",
+    "<environments_instructions>LITELLM ESCALATE environment</environments_instructions>",
+    "# AGENTS.md instructions for /repo with spaces/中文\n<INSTRUCTIONS>LITELLM ESCALATE instructions</INSTRUCTIONS>",
+)
 
 
 class TestContextAwareClassifier:
     """Test the new classifier context window and trajectory signals."""
 
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        "request_metadata,forwards_system",
+        [
+            ({"metadata": {"user_agent": "claude-cli/2.1.233"}}, False),
+            ({"litellm_metadata": {"user_agent": "claude-code/2.1.233"}}, False),
+            ({"metadata": {"user_agent": "curl/8.7.1"}}, True),
+            ({"litellm_metadata": {}}, True),
+            (
+                {"metadata": {"user_agent": "claude-cli/2.1.233"}, "litellm_metadata": {"user_agent": "curl/8.7.1"}},
+                False,
+            ),
+            ({"metadata": {"user_agent": "Claude-Code/2.1.233"}}, True),
+        ],
+    )
+    async def test_claude_code_classifier_omits_harness_system_prompt(
+        self,
+        llm_classifier_config: dict[str, object],
+        request_metadata: dict[str, object],
+        forwards_system: bool,
+    ) -> None:
+        dependency: Final = MagicMock(acompletion=AsyncMock(return_value=_llm_response('{"tier": "COMPLEX"}')))
+        router: Final = ComplexityRouter(
+            "test-complexity-router",
+            dependency,
+            {
+                **llm_classifier_config,
+                "classifier_context_include_assistant_turns": True,
+            },
+        )
+        messages: Final = [
+            {"role": "user", "content": "Design the retry state machine"},
+            {"role": "assistant", "content": "The design needs a lease and fencing token"},
+            {"role": "user", "content": "Now prove it cannot livelock"},
+            {
+                "role": "system",
+                "content": [{"type": "text", "text": "ENVIRONMENT_CATALOG\nAGENT_CATALOG\nSKILL_CATALOG"}],
+            },
+        ]
+        top_level_system: Final = [{"type": "text", "text": "TOP_LEVEL_HARNESS_SYSTEM"}]
+        claude_kwargs: Final = {
+            "metadata": {"user_agent": "claude-cli/2.1.233"},
+            "system": top_level_system,
+            "proxy_server_request": {"body": {"system": top_level_system}},
+        }
+        compared_kwargs: Final = {
+            **request_metadata,
+            "system": top_level_system,
+            "proxy_server_request": {"body": {"system": top_level_system}},
+        }
+        original_messages: Final = deepcopy(messages)
+        original_kwargs: Final = deepcopy((claude_kwargs, compared_kwargs))
+        results: Final = (
+            await router.async_pre_routing_hook("test-complexity-router", claude_kwargs, messages),
+            await router.async_pre_routing_hook("test-complexity-router", compared_kwargs, messages),
+        )
+
+        assert all(result is not None and result.routing_decision["cause"] == "llm_classifier" for result in results)
+        assert all(result is not None and result.messages == original_messages for result in results)
+        assert messages == original_messages
+        assert (claude_kwargs, compared_kwargs) == original_kwargs
+        calls: Final = tuple(call.kwargs["messages"] for call in dependency.acompletion.await_args_list)
+        assert calls[0][0]["content"] == calls[1][0]["content"] == classification_system_prompt(
+            router.config.classifier_context_window_size
+        )
+        payloads: Final = (calls[0][1]["content"], calls[1][1]["content"])
+        for payload, expected_system in zip(payloads, (False, forwards_system)):
+            assert payload.endswith("Classify this message:\nNow prove it cannot livelock")
+            assert ("ENVIRONMENT_CATALOG" in payload) is expected_system
+            assert ("AGENT_CATALOG" in payload) is expected_system
+            assert ("SKILL_CATALOG" in payload) is expected_system
+            assert "Design the retry state machine" in payload
+            assert "lease and fencing token" in payload
+            assert "TOP_LEVEL_HARNESS_SYSTEM" not in payload
+            assert "Conversation so far: ~35 tokens across the request" in payload
+
+    @pytest.mark.asyncio
+    async def test_claude_code_first_turn_without_context_omits_harness_system_prompt(
+        self, llm_classifier_config: dict[str, object]
+    ) -> None:
+        dependency: Final = MagicMock(acompletion=AsyncMock(return_value=_llm_response('{"tier": "SIMPLE"}')))
+        router: Final = ComplexityRouter(
+            "test-complexity-router",
+            dependency,
+            {**llm_classifier_config, "classifier_context_window_size": 0},
+        )
+        messages: Final = [
+            {"role": "user", "content": "What is two plus two?"},
+            {
+                "role": "system",
+                "content": [{"type": "text", "text": "ENVIRONMENT_CATALOG\nAGENT_CATALOG\nSKILL_CATALOG"}],
+            },
+        ]
+        request_kwargs: Final = {"litellm_metadata": {"user_agent": "claude-code/2.1.233"}}
+        original: Final = deepcopy((messages, request_kwargs))
+
+        result: Final = await router.async_pre_routing_hook("test-complexity-router", request_kwargs, messages)
+
+        assert result is not None and result.routing_decision["cause"] == "llm_classifier"
+        assert result.messages == messages == original[0]
+        assert request_kwargs == original[1]
+        classifier_messages: Final = dependency.acompletion.call_args.kwargs["messages"]
+        assert classifier_messages[0]["content"] == classification_system_prompt(
+            router.config.classifier_context_window_size
+        )
+        assert classifier_messages[1]["content"].strip() == "Classify this message:\nWhat is two plus two?"
+
+    @pytest.mark.parametrize(
+        "tail,expected",
+        (
+            ([{"role": "user", "content": [{"type": "text", "text": _CODEX_ENVELOPES[0]}]}], True),
+            ([{"role": "assistant", "content": _CODEX_ENVELOPES[0]}], False),
+            ([{"role": "tool", "content": _CODEX_ENVELOPES[0]}], False),
+            ([{"role": "user", "content": " "}], False),
+            (
+                [{"role": "user", "content": [_TOOL_RESULT, {"type": "text", "text": _CODEX_ENVELOPES[0]}]}],
+                False,
+            ),
+            (
+                [{"role": "user", "content": [{"type": "image_url"}, {"type": "text", "text": _CODEX_ENVELOPES[0]}]}],
+                False,
+            ),
+        ),
+    )
+    def test_only_text_reminder_tails_are_ignored_for_new_asks(self, tail: list[dict[str, object]], expected: bool) -> None:
+        from litellm.router_strategy.complexity_router.complexity_router import (
+            _CODEX_REMINDER_MARKERS,
+            _newest_turn_is_human_ask,
+        )
+
+        assert _newest_turn_is_human_ask([_ASKED, *tail], _CODEX_REMINDER_MARKERS) is expected
+        assert _newest_turn_is_human_ask(tail, _CODEX_REMINDER_MARKERS) is False
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("new_ask", (_CODEX_NEW_TASK, "Now design cache invalidation"))
+    @pytest.mark.parametrize("responses_api", (False, True))
+    @pytest.mark.parametrize("session_affinity", (False, True))
+    async def test_codex_tail_preserves_new_ask_and_tool_continuation_boundaries(
+        self, new_ask: str, responses_api: bool, session_affinity: bool
+    ) -> None:
+        completion: Final = AsyncMock(
+            side_effect=[_llm_response('{"tier":"SIMPLE"}'), _llm_response('{"tier":"COMPLEX"}')]
+        )
+        router: Final = ComplexityRouter(
+            model_name="router",
+            litellm_router_instance=MagicMock(acompletion=completion, cache=DualCache()),
+            complexity_router_config={
+                "tiers": {"SIMPLE": "simple-model", "COMPLEX": "task-model"},
+                "classifier_type": "llm",
+                "classifier_llm_config": {"model": "classifier-model"},
+                "classification_mode": "user_turn",
+                "session_affinity": session_affinity,
+                "escalation_keywords": [],
+            },
+        )
+        metadata: Final = {"user_agent": "codex-tui", "session_id": "codex-tail-session"}
+        first_messages: Final = [{"role": "user", "content": "Hello"}]
+        tail: Final = [{"role": "user", "content": envelope} for envelope in _CODEX_ENVELOPES]
+        new_messages: Final = [
+            *first_messages,
+            {"role": "assistant", "content": "Hello"},
+            {"role": "user", "content": new_ask},
+            *tail,
+        ]
+        continuation: Final = [
+            *new_messages,
+            {"role": "assistant", "content": "Working on it"},
+            {
+                "role": "user",
+                "content": [
+                    {"type": "tool_result", "tool_use_id": "read-cache", "content": "cache source"},
+                    {"type": "text", "text": _CODEX_ENVELOPES[0]},
+                ],
+            },
+            *tail,
+        ]
+        results: Final = [
+            await router.async_pre_routing_hook(
+                model="router",
+                request_kwargs=(
+                    {"input": messages, "litellm_metadata": {**metadata, "user_api_key_request_route": "/v1/responses"}}
+                    if responses_api
+                    else {"metadata": metadata}
+                ),
+                messages=None if responses_api else messages,
+                input=messages if responses_api else None,
+            )
+            for messages in (first_messages, new_messages, continuation)
+        ]
+
+        assert [result.model for result in results] == (
+            ["simple-model", "simple-model", "simple-model"]
+            if session_affinity
+            else ["simple-model", "task-model", "task-model"]
+        )
+        assert completion.await_count == (1 if session_affinity else 2)
+        assert results[-1].routing_decision["cause"] == (
+            "session_affinity_pin" if session_affinity else "user_turn_continuation"
+        )
+        if not session_affinity:
+            assert completion.call_args.kwargs["messages"][1]["content"].endswith(f"Classify this message:\n{new_ask}")
+        assert results[1].messages == (None if responses_api else new_messages)
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("envelope", _CODEX_ENVELOPES)
+    @pytest.mark.parametrize("user_agent", (None, "curl/8.7.1", "codexify/1.0"))
+    async def test_non_codex_requests_preserve_tagged_asks(self, envelope: str, user_agent: str | None) -> None:
+        completion: Final = AsyncMock(return_value=_llm_response('{"tier":"COMPLEX"}'))
+        router: Final = ComplexityRouter(
+            model_name="router",
+            litellm_router_instance=MagicMock(acompletion=completion),
+            complexity_router_config={
+                "tiers": {"COMPLEX": "task-model"},
+                "default_model": "fallback-model",
+                "classifier_type": "llm",
+                "classifier_llm_config": {"model": "classifier-model"},
+                "escalation_keywords": [],
+            },
+        )
+
+        response: Final = await router.async_pre_routing_hook(
+            model="router",
+            request_kwargs={"metadata": {"user_agent": user_agent}} if user_agent is not None else {},
+            messages=[{"role": "user", "content": envelope}],
+        )
+
+        assert response is not None
+        assert response.model == "task-model"
+        completion.assert_awaited_once()
+        assert completion.call_args.kwargs["messages"][1]["content"].strip() == f"Classify this message:\n{envelope}"
+
+    @pytest.mark.parametrize("envelope", _CODEX_ENVELOPES)
+    def test_codex_envelopes_preserve_delegated_task_and_prior_context(self, envelope: str) -> None:
+        from litellm.router_strategy.complexity_router.complexity_router import (
+            _CODEX_REMINDER_MARKERS,
+            _extract_current_ask_and_system_prompt,
+            _extract_prior_turns,
+            _newest_turn_ask,
+            _newest_turn_is_human_ask,
+        )
+
+        messages: Final = [
+            {"role": "user", "content": f"{envelope}\nDesign cache invalidation"},
+            {
+                "role": "user",
+                "content": [{"type": "text", "text": envelope}, {"type": "text", "text": _CODEX_NEW_TASK}],
+            },
+            {"role": "developer", "content": "<permissions instructions>developer scope</permissions instructions>"},
+            {"role": "user", "content": envelope},
+        ]
+
+        assert _extract_current_ask_and_system_prompt(messages, _CODEX_REMINDER_MARKERS)[0] == _CODEX_NEW_TASK
+        assert _extract_prior_turns(messages, _CODEX_NEW_TASK, 1, 100, None, False, _CODEX_REMINDER_MARKERS) == (
+            ("user", "Design cache invalidation"),
+        )
+        assert _newest_turn_ask(messages, _CODEX_REMINDER_MARKERS) is None
+        assert _newest_turn_is_human_ask(messages, _CODEX_REMINDER_MARKERS) is False
+        assert _extract_current_ask_and_system_prompt([messages[-1]], _CODEX_REMINDER_MARKERS)[0] is None
+
+    @pytest.mark.parametrize("envelope", _CODEX_ENVELOPES)
+    def test_codex_marker_override_and_incomplete_blocks_preserve_text(self, envelope: str) -> None:
+        from litellm.router_strategy.complexity_router.complexity_router import (
+            _CODEX_REMINDER_MARKERS,
+            _strip_reminder_blocks,
+        )
+
+        incomplete: Final = envelope.rsplit("</", 1)[0]
+        assert _strip_reminder_blocks(f"before {envelope.upper()} after", _CODEX_REMINDER_MARKERS) == "before after"
+        assert _strip_reminder_blocks(incomplete, _CODEX_REMINDER_MARKERS) == incomplete
+        assert _strip_reminder_blocks(envelope) == envelope
+        assert _strip_reminder_blocks(f"<custom>noise</custom>{envelope}", (("<custom>", "</custom>"),)) == envelope
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("responses_api", (False, True))
+    async def test_codex_routing_preserves_original_request(self, responses_api: bool) -> None:
+        completion: Final = AsyncMock(return_value=_llm_response('{"tier":"COMPLEX"}'))
+        router: Final = ComplexityRouter(
+            model_name="codex-router",
+            litellm_router_instance=MagicMock(acompletion=completion),
+            complexity_router_config={
+                "tiers": {"COMPLEX": "task-model", "REASONING": "escalated-model"},
+                "classifier_type": "llm",
+                "classifier_llm_config": {"model": "classifier-model"},
+                "keyword_tier_rules": [{"keywords": ["LITELLM ESCALATE"], "tier": "REASONING"}],
+            },
+        )
+        messages: Final = [
+            {"role": "user", "content": _CODEX_NEW_TASK},
+            {"role": "user", "content": "\n".join(_CODEX_ENVELOPES)},
+        ]
+        original: Final = deepcopy(messages)
+        request_kwargs: Final = (
+            {
+                "input": messages,
+                "litellm_metadata": {"user_api_key_request_route": "/v1/responses", "user_agent": "codex-tui"},
+            }
+            if responses_api
+            else {"metadata": {"user_agent": "codex-tui"}}
+        )
+
+        response: Final = await router.async_pre_routing_hook(
+            model="codex-router",
+            request_kwargs=request_kwargs,
+            messages=None if responses_api else messages,
+            input=messages if responses_api else None,
+        )
+
+        assert response is not None
+        assert response.model == "task-model"
+        completion.assert_awaited_once()
+        assert completion.call_args.kwargs["messages"][1]["content"].strip() == (
+            f"Classify this message:\n{_CODEX_NEW_TASK}"
+        )
+        assert messages == original
+        if responses_api:
+            assert response.messages is None
+            assert request_kwargs["input"] == original
+        else:
+            assert response.messages == original
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("custom_markers", (False, True))
+    async def test_codex_markers_are_request_scoped_and_respect_overrides(self, custom_markers: bool) -> None:
+        completion: Final = AsyncMock(return_value=_llm_response('{"tier":"COMPLEX"}'))
+        router: Final = ComplexityRouter(
+            model_name="router",
+            litellm_router_instance=MagicMock(acompletion=completion),
+            complexity_router_config={
+                "tiers": {"COMPLEX": "task-model"},
+                "classifier_type": "llm",
+                "classifier_llm_config": {"model": "classifier-model"},
+                "classifier_context_window_size": 2,
+                "escalation_keywords": [],
+                **({"reminder_markers": [{"open": "<custom>", "close": "</custom>"}]} if custom_markers else {}),
+            },
+        )
+        envelope: Final = "\n".join(_CODEX_ENVELOPES)
+        prior: Final = f"{envelope}\nDesign cache invalidation"
+        messages: Final = [
+            {"role": "user", "content": prior},
+            {"role": "user", "content": _CODEX_NEW_TASK},
+            {"role": "user", "content": envelope},
+        ]
+        for user_agent in ("codex-tui", "curl/8.7.1", "codex_cli_rs/0.62.0"):
+            response: Final = await router.async_pre_routing_hook(
+                model="router", request_kwargs={"metadata": {"user_agent": user_agent}}, messages=messages
+            )
+            assert response is not None
+            assert response.model == "task-model"
+            payload: Final = completion.call_args.kwargs["messages"][1]["content"]
+            if user_agent.startswith("codex") and not custom_markers:
+                assert payload.endswith(f"Classify this message:\n{_CODEX_NEW_TASK}")
+                assert "Design cache invalidation" in payload
+                assert "LITELLM ESCALATE" not in payload
+            else:
+                assert payload.endswith(f"Classify this message:\n{envelope}")
+                assert prior in payload
+            assert response.messages == messages
+        assert completion.await_count == 3
+
     @pytest.mark.parametrize(
         "messages,expected_ask",
         [
@@ -13662,6 +14430,7 @@ class _OutputCeilingRecorder(CustomLogger):
     def log_pre_api_call(self, model, messages, kwargs):
         self.seen.append((model, kwargs.get("optional_params", {}).get("max_tokens")))
 
+
 NON_REASONING_TIERS: Final = {
     "NON_REASONING": "gpt-4o-mini",
     "SIMPLE": "gpt-4o-mini",
diff --git a/tests/test_litellm/router_strategy/test_least_busy.py b/tests/test_litellm/router_strategy/test_least_busy.py
index 9efa526fc02..c2fa41f4ca8 100644
--- a/tests/test_litellm/router_strategy/test_least_busy.py
+++ b/tests/test_litellm/router_strategy/test_least_busy.py
@@ -1,9 +1,11 @@
+import logging
 from typing import Final
 
 import pytest
 
 from litellm.caching.caching import DualCache
 from litellm.caching.in_memory_cache import InMemoryCache
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 from litellm.router_strategy.least_busy import IN_FLIGHT_COUNT_TTL_SECONDS, LeastBusyLoggingHandler
 
 GROUP: Final = "least-busy-group"
@@ -185,3 +187,24 @@ def test_calls_without_a_deployment_are_ignored() -> None:
     worker.log_pre_api_call(model="m", messages=[], kwargs={})
 
     assert shared.counts == {}
+
+
+class OpenBreakerRedis(SharedRedisCounters):
+    def increment_with_floor(self, key: str, value: int, ttl: int) -> int:
+        raise RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+
+    def batch_get_counts(self, key_list: list[str]) -> tuple[int | None, ...]:
+        raise RedisCircuitBreakerOpenError("Redis circuit breaker is open")
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_falls_back_without_a_warning_per_request(caplog: pytest.LogCaptureFixture) -> None:
+    worker: Final = _worker(OpenBreakerRedis())
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Router"):
+        worker.log_pre_api_call(model="m", messages=[], kwargs=_call_kwargs("dep-a"))
+        picked: Final = worker.get_available_deployments(GROUP, HEALTHY)
+
+    assert picked is DEPLOYMENT_B
+    assert [record.getMessage() for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert sum("circuit breaker is open" in record.getMessage() for record in caplog.records) == 2
diff --git a/tests/test_litellm/router_strategy/test_lowest_latency.py b/tests/test_litellm/router_strategy/test_lowest_latency.py
index 812d7bbff32..1a8614e3fca 100644
--- a/tests/test_litellm/router_strategy/test_lowest_latency.py
+++ b/tests/test_litellm/router_strategy/test_lowest_latency.py
@@ -8,11 +8,12 @@ import json
 from datetime import datetime, timedelta
 
 import pytest
-
+from pydantic import ValidationError
 
 import litellm
 from litellm.caching.caching import DualCache
-from litellm.router_strategy.lowest_latency import LowestLatencyLoggingHandler
+from litellm.router import Router
+from litellm.router_strategy.lowest_latency import LowestLatencyLoggingHandler, RoutingArgs
 
 DEPLOYMENT_ID = "9876"
 KWARGS = {
@@ -58,9 +59,9 @@ def test_sync_embedding_latency_is_json_serializable():
 
     latencies = _recorded_latencies(cache)
     assert latencies, "expected a latency entry to be recorded"
-    assert all(
-        not isinstance(value, timedelta) for value in latencies
-    ), f"raw timedelta leaked into latency list: {latencies}"
+    assert all(not isinstance(value, timedelta) for value in latencies), (
+        f"raw timedelta leaked into latency list: {latencies}"
+    )
     assert latencies[-1] == pytest.approx(2.0)
     # the exact failure mode from production: redis cache sync json.dumps
     json.dumps({"latency": latencies})
@@ -84,9 +85,9 @@ async def test_async_embedding_latency_is_json_serializable():
 
     latencies = _recorded_latencies(cache)
     assert latencies, "expected a latency entry to be recorded"
-    assert all(
-        not isinstance(value, timedelta) for value in latencies
-    ), f"raw timedelta leaked into latency list: {latencies}"
+    assert all(not isinstance(value, timedelta) for value in latencies), (
+        f"raw timedelta leaked into latency list: {latencies}"
+    )
     assert latencies[-1] == pytest.approx(3.0)
     json.dumps({"latency": latencies})
 
@@ -292,6 +293,85 @@ async def test_streaming_routing_ignores_per_token_ttft_samples_from_older_worke
     assert picked["model_info"]["id"] == FAST_TTFT_ID
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize("sync_mode", [True, False], ids=["sync", "async"])
+@pytest.mark.parametrize(
+    ("ttft_percentile", "first_samples", "second_samples", "expected_id"),
+    [
+        (None, [0.1, 0.1, 1.0], [0.3, 0.3, 0.3], SLOW_TTFT_ID),
+        (0.5, [0.1, 0.1, 1.0], [0.3, 0.3, 0.3], FAST_TTFT_ID),
+        (0.9, [0.1, 0.1, 0.1, 0.1, 1.5], [0.3, 0.3, 0.3, 0.3, 0.3], SLOW_TTFT_ID),
+    ],
+    ids=["default_average", "p50", "p90"],
+)
+async def test_streaming_ttft_ranking_percentile(
+    sync_mode: bool,
+    ttft_percentile: float | None,
+    first_samples: list[float],
+    second_samples: list[float],
+    expected_id: str,
+):
+    cache = DualCache()
+    routing_args = {} if ttft_percentile is None else {"ttft_percentile": ttft_percentile}
+    handler = LowestLatencyLoggingHandler(router_cache=cache, routing_args=routing_args)
+    cache.set_cache(
+        key=f"{MODEL_GROUP}_map",
+        value={
+            FAST_TTFT_ID: {"time_to_first_token_seconds": first_samples},
+            SLOW_TTFT_ID: {"time_to_first_token_seconds": second_samples},
+        },
+    )
+
+    if sync_mode:
+        picked = handler.get_available_deployments(
+            model_group=MODEL_GROUP,
+            healthy_deployments=STREAMING_DEPLOYMENTS,
+            request_kwargs={"stream": True, "metadata": {}},
+        )
+    else:
+        picked = await handler.async_get_available_deployments(
+            model_group=MODEL_GROUP,
+            healthy_deployments=STREAMING_DEPLOYMENTS,
+            request_kwargs={"stream": True, "metadata": {}},
+        )
+
+    assert picked is not None
+    assert picked["model_info"]["id"] == expected_id
+
+
+@pytest.mark.parametrize("ttft_percentile", [0, -0.1, 1.1])
+def test_ttft_percentile_validation(ttft_percentile: float):
+    with pytest.raises(ValidationError):
+        RoutingArgs(ttft_percentile=ttft_percentile)
+
+
+@pytest.mark.parametrize("ttft_percentile", [0.5, 0.9, 0.95, 1.0])
+def test_ttft_percentile_accepts_valid_values(ttft_percentile: float):
+    assert RoutingArgs(ttft_percentile=ttft_percentile).ttft_percentile == ttft_percentile
+
+
+@pytest.mark.asyncio
+async def test_ttft_percentile_does_not_change_non_streaming_routing():
+    cache = DualCache()
+    handler = LowestLatencyLoggingHandler(router_cache=cache, routing_args={"ttft_percentile": 0.9})
+    cache.set_cache(
+        key=f"{MODEL_GROUP}_map",
+        value={
+            FAST_TTFT_ID: {"latency": [1.0], "time_to_first_token_seconds": [0.1]},
+            SLOW_TTFT_ID: {"latency": [0.2], "time_to_first_token_seconds": [1.5]},
+        },
+    )
+
+    picked = await handler.async_get_available_deployments(
+        model_group=MODEL_GROUP,
+        healthy_deployments=STREAMING_DEPLOYMENTS,
+        request_kwargs={"stream": False, "metadata": {}},
+    )
+
+    assert picked is not None
+    assert picked["model_info"]["id"] == SLOW_TTFT_ID
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "cached_entry",
@@ -318,3 +398,81 @@ async def test_async_get_available_deployments_treats_missing_samples_as_zero_la
 
     assert picked is not None
     assert picked["model_info"]["id"] == DEPLOYMENT_ID
+
+
+def _latency_router(routing_strategy_args: dict) -> Router:
+    return Router(
+        model_list=[
+            {
+                "model_name": MODEL_GROUP,
+                "litellm_params": {"model": f"openai/{MODEL_GROUP}", "api_key": "sk-fake"},
+                "model_info": {"id": deployment_id},
+            }
+            for deployment_id in (FAST_TTFT_ID, SLOW_TTFT_ID)
+        ],
+        routing_strategy="latency-based-routing",
+        routing_strategy_args=routing_strategy_args,
+    )
+
+
+def _seed_streaming_ttft(router: Router) -> None:
+    router.cache.set_cache(
+        key=f"{MODEL_GROUP}_map",
+        value={
+            FAST_TTFT_ID: {"time_to_first_token_seconds": [0.1, 0.1, 1.0]},
+            SLOW_TTFT_ID: {"time_to_first_token_seconds": [0.3, 0.3, 0.3]},
+        },
+    )
+
+
+async def _pick_streaming(router: Router) -> str:
+    picked = await router.async_get_available_deployment(
+        model=MODEL_GROUP,
+        request_kwargs={"stream": True, "metadata": {}},
+    )
+    return picked["model_info"]["id"]
+
+
+@pytest.mark.asyncio
+async def test_runtime_routing_strategy_args_update_applies_ttft_percentile():
+    """A config reload that adds ttft_percentile must reach the live selector,
+    not sit unused until the proxy restarts."""
+    router = _latency_router({"max_latency_list_size": 50})
+    _seed_streaming_ttft(router)
+
+    assert await _pick_streaming(router) == SLOW_TTFT_ID
+
+    router.update_settings(routing_strategy_args={"max_latency_list_size": 50, "ttft_percentile": 0.5})
+
+    assert await _pick_streaming(router) == FAST_TTFT_ID
+
+
+@pytest.mark.asyncio
+async def test_runtime_routing_strategy_args_update_keeps_previous_args_when_invalid():
+    router = _latency_router({"ttft_percentile": 0.5})
+    _seed_streaming_ttft(router)
+
+    router.update_settings(routing_strategy_args={"ttft_percentile": 5})
+
+    assert await _pick_streaming(router) == FAST_TTFT_ID
+
+
+@pytest.mark.asyncio
+async def test_runtime_routing_strategy_args_update_is_a_noop_without_a_selector():
+    """simple-shuffle has no selector to re-link, so an args update must leave
+    the router alone instead of blowing up on a missing selector attribute."""
+    router = Router(
+        model_list=[
+            {
+                "model_name": MODEL_GROUP,
+                "litellm_params": {"model": f"openai/{MODEL_GROUP}", "api_key": "sk-fake"},
+                "model_info": {"id": FAST_TTFT_ID},
+            }
+        ],
+        routing_strategy="simple-shuffle",
+    )
+
+    router.update_settings(routing_strategy_args={"ttl": 5})
+
+    assert router.routing_strategy_args == {"ttl": 5}
+    assert await _pick_streaming(router) == FAST_TTFT_ID
diff --git a/tests/test_litellm/router_utils/pre_call_checks/test_encrypted_content_affinity_check.py b/tests/test_litellm/router_utils/pre_call_checks/test_encrypted_content_affinity_check.py
index dac991a41c4..ea8e2eacaa6 100644
--- a/tests/test_litellm/router_utils/pre_call_checks/test_encrypted_content_affinity_check.py
+++ b/tests/test_litellm/router_utils/pre_call_checks/test_encrypted_content_affinity_check.py
@@ -16,12 +16,10 @@ The mechanism works without any cache and supports two encoding strategies:
 """
 
 import time
-from typing import List, Optional
 from unittest.mock import AsyncMock, patch
 
 import pytest
 
-
 import litellm
 from litellm.responses.utils import ResponsesAPIRequestUtils
 from litellm.types.llms.openai import ResponsesAPIResponse
@@ -68,9 +66,7 @@ class TestEncryptedItemIdCodec:
     def test_roundtrip(self):
         model_id = "deployment-1"
         original_item_id = "rs_abc123def456"
-        encoded = ResponsesAPIRequestUtils._build_encrypted_item_id(
-            model_id, original_item_id
-        )
+        encoded = ResponsesAPIRequestUtils._build_encrypted_item_id(model_id, original_item_id)
         assert encoded.startswith("encitem_")
         decoded = ResponsesAPIRequestUtils._decode_encrypted_item_id(encoded)
         assert decoded is not None
@@ -81,9 +77,7 @@ class TestEncryptedItemIdCodec:
         """Decoding must succeed even if base64 padding (=) was stripped in transit."""
         model_id = "gpt-5.1-codex-openai-2"
         original_item_id = "rs_0efb96cb222403210069a01d5d52588196a9dc394ffdb89d00"
-        encoded = ResponsesAPIRequestUtils._build_encrypted_item_id(
-            model_id, original_item_id
-        )
+        encoded = ResponsesAPIRequestUtils._build_encrypted_item_id(model_id, original_item_id)
         # Strip any trailing '=' to simulate what happens in transit
         stripped = encoded.rstrip("=")
         decoded = ResponsesAPIRequestUtils._decode_encrypted_item_id(stripped)
@@ -100,9 +94,7 @@ class TestEncryptedItemIdCodec:
         """item_id values containing ';' must survive the roundtrip."""
         model_id = "deployment-1"
         original_item_id = "rs_part1;part2;part3"
-        encoded = ResponsesAPIRequestUtils._build_encrypted_item_id(
-            model_id, original_item_id
-        )
+        encoded = ResponsesAPIRequestUtils._build_encrypted_item_id(model_id, original_item_id)
         decoded = ResponsesAPIRequestUtils._decode_encrypted_item_id(encoded)
         assert decoded is not None
         assert decoded["item_id"] == original_item_id
@@ -118,11 +110,7 @@ class TestUpdateEncryptedContentItemIds:
                 {"id": "rs_xyz", "type": "reasoning", "encrypted_content": "secret"},
             ],
         }
-        result = (
-            ResponsesAPIRequestUtils._update_encrypted_content_item_ids_in_response(
-                response, model_id
-            )
-        )
+        result = ResponsesAPIRequestUtils._update_encrypted_content_item_ids_in_response(response, model_id)
         # Plain message item untouched
         assert result["output"][0]["id"] == "msg_abc"
         # Reasoning item with encrypted_content gets encoded
@@ -133,16 +121,8 @@ class TestUpdateEncryptedContentItemIds:
         assert decoded["item_id"] == "rs_xyz"
 
     def test_no_op_when_model_id_is_none(self):
-        response = {
-            "output": [
-                {"id": "rs_xyz", "type": "reasoning", "encrypted_content": "secret"}
-            ]
-        }
-        result = (
-            ResponsesAPIRequestUtils._update_encrypted_content_item_ids_in_response(
-                response, None
-            )
-        )
+        response = {"output": [{"id": "rs_xyz", "type": "reasoning", "encrypted_content": "secret"}]}
+        result = ResponsesAPIRequestUtils._update_encrypted_content_item_ids_in_response(response, None)
         assert result["output"][0]["id"] == "rs_xyz"
 
 
@@ -151,9 +131,7 @@ class TestEncryptedContentWrapping:
         """Test wrapping encrypted_content with model_id metadata."""
         model_id = "deployment-1"
         original_content = "gAAAAABpnW_yEYmSNEyOG_original_encrypted_data"
-        wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(
-            original_content, model_id
-        )
+        wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(original_content, model_id)
         assert wrapped.startswith("litellm_enc:")
         assert wrapped != original_content
 
@@ -170,9 +148,7 @@ class TestEncryptedContentWrapping:
         (
             model_id,
             content,
-        ) = ResponsesAPIRequestUtils._unwrap_encrypted_content_with_model_id(
-            plain_content
-        )
+        ) = ResponsesAPIRequestUtils._unwrap_encrypted_content_with_model_id(plain_content)
         assert model_id is None
         assert content == plain_content
 
@@ -189,11 +165,7 @@ class TestEncryptedContentWrapping:
                 },
             ],
         }
-        result = (
-            ResponsesAPIRequestUtils._update_encrypted_content_item_ids_in_response(
-                response, model_id
-            )
-        )
+        result = ResponsesAPIRequestUtils._update_encrypted_content_item_ids_in_response(response, model_id)
         assert result["output"][0].get("encrypted_content") is None
         wrapped = result["output"][1]["encrypted_content"]
         assert wrapped.startswith("litellm_enc:")
@@ -210,19 +182,13 @@ class TestRestoreEncryptedContentItemIds:
     def test_restores_encoded_ids(self):
         model_id = "deployment-1"
         original_id = "rs_encrypted_item_456"
-        encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-            model_id, original_id
-        )
+        encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(model_id, original_id)
 
         request_input = [
             {"type": "message", "id": "msg_abc123", "role": "assistant"},
             {"type": "reasoning", "id": encoded_id, "encrypted_content": "secret"},
         ]
-        restored = (
-            ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(
-                request_input
-            )
-        )
+        restored = ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(request_input)
         assert restored[0]["id"] == "msg_abc123"
         assert restored[1]["id"] == original_id
 
@@ -230,33 +196,21 @@ class TestRestoreEncryptedContentItemIds:
         """Test that wrapped encrypted_content is unwrapped before forwarding."""
         model_id = "deployment-1"
         original_content = "gAAAAABpnW_yEYmSNEyOG_original"
-        wrapped_content = (
-            ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(
-                original_content, model_id
-            )
-        )
+        wrapped_content = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(original_content, model_id)
 
         request_input = [
             {"type": "reasoning", "encrypted_content": wrapped_content},
         ]
-        restored = (
-            ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(
-                request_input
-            )
-        )
+        restored = ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(request_input)
         assert restored[0]["encrypted_content"] == original_content
 
     def test_no_op_for_plain_string_input(self):
-        result = ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(
-            "Hello world"
-        )
+        result = ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input("Hello world")
         assert result == "Hello world"
 
     def test_no_op_for_unencoded_ids(self):
         request_input = [{"type": "message", "id": "msg_plain"}]
-        result = ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(
-            request_input
-        )
+        result = ResponsesAPIRequestUtils._restore_encrypted_content_item_ids_in_input(request_input)
         assert result[0]["id"] == "msg_plain"
 
 
@@ -283,9 +237,7 @@ async def test_encrypted_content_affinity_tracks_and_routes():
                 "id": "msg_abc123",
                 "status": "completed",
                 "role": "assistant",
-                "content": [
-                    {"type": "output_text", "text": "Hello!", "annotations": []}
-                ],
+                "content": [{"type": "output_text", "text": "Hello!", "annotations": []}],
             },
             {
                 "type": "reasoning",
@@ -347,9 +299,9 @@ async def test_encrypted_content_affinity_tracks_and_routes():
 
         # The response must have rewritten the encrypted item's ID to encoded form
         encoded_item_id = _extract_encoded_item_id(first_response)
-        assert encoded_item_id.startswith(
-            "encitem_"
-        ), f"Expected output item ID to be rewritten to encitem_... but got {encoded_item_id!r}"
+        assert encoded_item_id.startswith("encitem_"), (
+            f"Expected output item ID to be rewritten to encitem_... but got {encoded_item_id!r}"
+        )
 
         # Verify the encoded ID decodes back to the correct deployment + original ID
         decoded = ResponsesAPIRequestUtils._decode_encrypted_item_id(encoded_item_id)
@@ -371,9 +323,9 @@ async def test_encrypted_content_affinity_tracks_and_routes():
         )
         second_model_id = second_response._hidden_params["model_id"]
 
-        assert (
-            second_model_id == first_model_id
-        ), f"Expected affinity to route to {first_model_id}, but got {second_model_id}"
+        assert second_model_id == first_model_id, (
+            f"Expected affinity to route to {first_model_id}, but got {second_model_id}"
+        )
 
 
 @pytest.mark.asyncio
@@ -478,9 +430,7 @@ async def test_encrypted_content_affinity_bypasses_rpm_limits():
 
         # Extract encoded item ID from the first response output
         encoded_item_id = _extract_encoded_item_id(first_response)
-        assert encoded_item_id.startswith(
-            "encitem_"
-        ), f"Expected encitem_... but got {encoded_item_id!r}"
+        assert encoded_item_id.startswith("encitem_"), f"Expected encitem_... but got {encoded_item_id!r}"
 
         # Follow-up with the encoded item ID — should pin to same deployment
         second_response = await router.aresponses(
@@ -628,17 +578,13 @@ async def test_encrypted_content_affinity_with_wrapped_content_no_id():
             if hasattr(first_item, "encrypted_content")
             else first_item.get("encrypted_content")
         )
-        assert wrapped_content.startswith(
-            "litellm_enc:"
-        ), f"Expected wrapped content but got {wrapped_content[:50]}..."
+        assert wrapped_content.startswith("litellm_enc:"), f"Expected wrapped content but got {wrapped_content[:50]}..."
 
         # Verify we can extract model_id from wrapped content
         (
             extracted_model_id,
             _,
-        ) = ResponsesAPIRequestUtils._unwrap_encrypted_content_with_model_id(
-            wrapped_content
-        )
+        ) = ResponsesAPIRequestUtils._unwrap_encrypted_content_with_model_id(wrapped_content)
         assert extracted_model_id == first_model_id
 
         # Second request: use wrapped encrypted_content WITHOUT an ID (Codex behavior)
@@ -653,9 +599,9 @@ async def test_encrypted_content_affinity_with_wrapped_content_no_id():
         )
         second_model_id = second_response._hidden_params["model_id"]
 
-        assert (
-            second_model_id == first_model_id
-        ), f"Expected affinity to route to {first_model_id}, but got {second_model_id}"
+        assert second_model_id == first_model_id, (
+            f"Expected affinity to route to {first_model_id}, but got {second_model_id}"
+        )
 
 
 def test_encrypted_content_wrapping_preserves_original_content():
@@ -664,13 +610,9 @@ def test_encrypted_content_wrapping_preserves_original_content():
     This is critical for streaming responses where content must round-trip correctly.
     """
     model_id = "test-deployment-1"
-    original_encrypted_content = (
-        "gAAAAABpnW_yEYmSNEyOG_streaming_test_content_with_special_chars==+/"
-    )
+    original_encrypted_content = "gAAAAABpnW_yEYmSNEyOG_streaming_test_content_with_special_chars==+/"
 
-    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(
-        original_encrypted_content, model_id
-    )
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(original_encrypted_content, model_id)
 
     assert wrapped.startswith("litellm_enc:")
     assert wrapped != original_encrypted_content
@@ -691,9 +633,7 @@ def test_encrypted_content_wrapping_with_multiple_semicolons():
     model_id = "deployment-with-semicolons"
     original_content = "gAAAAAB;some;content;with;semicolons"
 
-    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(
-        original_content, model_id
-    )
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(original_content, model_id)
 
     (
         extracted_model_id,
@@ -764,9 +704,7 @@ async def test_encrypted_content_affinity_preserves_litellm_metadata_for_respons
         request_kwargs=request_kwargs,
     )
 
-    assert (
-        request_kwargs["litellm_metadata"]["encrypted_content_affinity_enabled"] is True
-    )
+    assert request_kwargs["litellm_metadata"]["encrypted_content_affinity_enabled"] is True
     assert request_kwargs["litellm_metadata"]["model_info"] == {"id": "dep-1"}
 
 
@@ -777,9 +715,7 @@ def test_encrypted_content_wrapping_empty_string():
     model_id = "test-deployment"
     original_content = ""
 
-    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(
-        original_content, model_id
-    )
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id(original_content, model_id)
 
     assert wrapped.startswith("litellm_enc:")
 
@@ -1132,9 +1068,7 @@ def test_boundary_key_accepts_pydantic_litellm_params_instance():
         "api_key": "fake-azure-resource-key-a",
     }
 
-    pydantic_key = EncryptedContentAffinityCheck._encryption_boundary_key(
-        pydantic_params
-    )
+    pydantic_key = EncryptedContentAffinityCheck._encryption_boundary_key(pydantic_params)
     plain_key = EncryptedContentAffinityCheck._encryption_boundary_key(plain_params)
 
     assert pydantic_key is not None
@@ -1161,18 +1095,8 @@ def test_boundary_key_rejects_non_dict_like_inputs():
     for bad in (None, [], "not a dict", 42, object()):
         assert EncryptedContentAffinityCheck._encryption_boundary_key(bad) is None
 
-    assert (
-        EncryptedContentAffinityCheck._encryption_boundary_key(
-            {"api_base": "", "api_key": "k"}
-        )
-        is None
-    )
-    assert (
-        EncryptedContentAffinityCheck._encryption_boundary_key(
-            {"api_base": "https://x"}
-        )
-        is None
-    )
+    assert EncryptedContentAffinityCheck._encryption_boundary_key({"api_base": "", "api_key": "k"}) is None
+    assert EncryptedContentAffinityCheck._encryption_boundary_key({"api_base": "https://x"}) is None
 
 
 # ---------------------------------------------------------------------------
@@ -1180,10 +1104,11 @@ def test_boundary_key_rejects_non_dict_like_inputs():
 # ---------------------------------------------------------------------------
 
 
-def _make_originating_mock(api_base: str, api_key: str):
+def _make_originating_mock(api_base: str, api_key: str, model_name: str = "gpt-5.4"):
     from unittest.mock import MagicMock
 
     originating = MagicMock()
+    originating.model_name = model_name
     originating.litellm_params.model_dump.return_value = {
         "api_base": api_base,
         "api_key": api_key,
@@ -1192,19 +1117,23 @@ def _make_originating_mock(api_base: str, api_key: str):
 
 
 def _make_router_mock_with_cooldown(
-    originating, cooldown_entries: Optional[List[tuple]] = None
+    originating,
+    cooldown_entries: list[tuple] | None = None,
+    routed_group_model_ids: list[str] | None = None,
 ):
     """
     Build a MagicMock router whose ``cooldown_cache.async_get_active_cooldowns``
-    returns ``cooldown_entries`` (defaulting to ``[]`` — no active cooldown).
+    returns ``cooldown_entries`` (defaulting to ``[]`` — no active cooldown), and
+    whose ``get_candidate_model_ids_for_route`` returns ``routed_group_model_ids``
+    (the deployment ids the router resolves for the routed model; defaulting to ``[]``
+    — origin absent from the routed group, i.e. a tier change).
     """
     from unittest.mock import AsyncMock, MagicMock
 
     mock_router = MagicMock()
     mock_router.get_deployment.return_value = originating
-    mock_router.cooldown_cache.async_get_active_cooldowns = AsyncMock(
-        return_value=list(cooldown_entries or [])
-    )
+    mock_router.cooldown_cache.async_get_active_cooldowns = AsyncMock(return_value=list(cooldown_entries or []))
+    mock_router.get_candidate_model_ids_for_route.return_value = frozenset(routed_group_model_ids or [])
     return mock_router
 
 
@@ -1235,15 +1164,15 @@ async def test_affinity_raises_service_unavailable_when_origin_cooled_for_non_42
                 },
             )
         ],
+        routed_group_model_ids=["deployment-a-cooled", "deployment-b"],
     )
 
     check = EncryptedContentAffinityCheck(router=mock_router)
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-a-cooled", "rs_test"
-    )
+    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-a-cooled", "rs_test")
     healthy_only_b = [
         {
             "model_info": {"id": "deployment-b"},
+            "model_name": "gpt-5.4",
             "litellm_params": {
                 "api_base": "https://account-b.openai.azure.com/",
                 "api_key": "key-b",
@@ -1297,15 +1226,15 @@ async def test_affinity_raises_rate_limit_with_retry_after_when_origin_cooled_fo
                 },
             )
         ],
+        routed_group_model_ids=["deployment-a-cooled-429", "deployment-b"],
     )
 
     check = EncryptedContentAffinityCheck(router=mock_router)
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-a-cooled-429", "rs_test"
-    )
+    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-a-cooled-429", "rs_test")
     healthy_only_b = [
         {
             "model_info": {"id": "deployment-b"},
+            "model_name": "gpt-5.4",
             "litellm_params": {
                 "api_base": "https://account-b.openai.azure.com/",
                 "api_key": "key-b",
@@ -1345,15 +1274,16 @@ async def test_affinity_raises_service_unavailable_when_origin_filtered_without_
     )
 
     originating = _make_originating_mock("https://account-a.openai.azure.com/", "key-a")
-    mock_router = _make_router_mock_with_cooldown(originating, cooldown_entries=[])
+    mock_router = _make_router_mock_with_cooldown(
+        originating, cooldown_entries=[], routed_group_model_ids=["deployment-a-filtered", "deployment-b"]
+    )
 
     check = EncryptedContentAffinityCheck(router=mock_router)
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-a-filtered", "rs_test"
-    )
+    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-a-filtered", "rs_test")
     healthy_only_b = [
         {
             "model_info": {"id": "deployment-b"},
+            "model_name": "gpt-5.4",
             "litellm_params": {
                 "api_base": "https://account-b.openai.azure.com/",
                 "api_key": "key-b",
@@ -1377,15 +1307,18 @@ async def test_affinity_raises_service_unavailable_when_origin_filtered_without_
 
 
 @pytest.mark.asyncio
-async def test_affinity_raises_bad_request_when_origin_removed():
+async def test_affinity_strips_and_dispatches_when_origin_is_unknown_or_removed():
     """
-    Originating deployment was removed from the router config and no boundary
-    peer is available. This is permanent (the stale encrypted_content cannot
-    be honored), so surface a 400 with actionable text.
+    A removed deployment, or a forged/unknown affinity marker, resolves to no
+    originating deployment. It is handled like a cross-group origin: the encrypted
+    reasoning is stripped and the request dispatches with its readable history,
+    rather than returning a distinguishable error. That uniform handling denies an
+    authenticated caller a deployment-id existence oracle, an existing cross-group id
+    and a nonexistent id both strip and proceed, so responses cannot be told apart.
+    The membership lookup is skipped entirely when the origin is unknown.
     """
     from unittest.mock import MagicMock
 
-    from litellm.exceptions import BadRequestError
     from litellm.router_utils.pre_call_checks.encrypted_content_affinity_check import (
         EncryptedContentAffinityCheck,
     )
@@ -1394,12 +1327,11 @@ async def test_affinity_raises_bad_request_when_origin_removed():
     mock_router.get_deployment.return_value = None
 
     check = EncryptedContentAffinityCheck(router=mock_router)
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-removed", "rs_test"
-    )
-    healthy_only_b = [
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA-blob", "deployment-removed")
+    routed_pool = [
         {
             "model_info": {"id": "deployment-b"},
+            "model_name": "gpt-5.4",
             "litellm_params": {
                 "api_base": "https://account-b.openai.azure.com/",
                 "api_key": "key-b",
@@ -1408,18 +1340,28 @@ async def test_affinity_raises_bad_request_when_origin_removed():
         }
     ]
     request_kwargs = {
-        "input": [{"id": encoded_id, "type": "reasoning"}],
+        "litellm_metadata": {},
+        "input": [
+            {"role": "user", "content": "why is the sky blue?"},
+            {
+                "type": "reasoning",
+                "encrypted_content": wrapped,
+                "summary": [{"type": "summary_text", "text": "scattering"}],
+            },
+            {"role": "user", "content": "and sunsets?"},
+        ],
     }
 
-    with pytest.raises(BadRequestError) as excinfo:
-        await check.async_filter_deployments(
-            model="gpt-5.4",
-            healthy_deployments=healthy_only_b,
-            messages=None,
-            request_kwargs=request_kwargs,
-        )
+    result = await check.async_filter_deployments(
+        model="gpt-5.4",
+        healthy_deployments=routed_pool,
+        messages=None,
+        request_kwargs=request_kwargs,
+    )
 
-    assert "deployment-removed" not in str(excinfo.value)
+    assert result is routed_pool
+    assert not any(isinstance(item, dict) and item.get("encrypted_content") for item in request_kwargs["input"])
+    mock_router.get_candidate_model_ids_for_route.assert_not_called()
 
 
 @pytest.mark.asyncio
@@ -1444,9 +1386,7 @@ async def test_affinity_does_not_raise_when_boundary_peer_available():
     mock_router.get_deployment.return_value = originating
 
     check = EncryptedContentAffinityCheck(router=mock_router)
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-a", "rs_test"
-    )
+    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-a", "rs_test")
     peer = {
         "model_info": {"id": "deployment-a-peer"},
         "litellm_params": {
@@ -1490,9 +1430,7 @@ async def test_model_group_affinity_config_enables_encrypted_content_affinity():
         },
         target_deployment,
     ]
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-b", "rs_test"
-    )
+    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-b", "rs_test")
     request_kwargs = {
         "input": [{"type": "reasoning", "id": encoded_id}],
         "litellm_metadata": {},
@@ -1536,9 +1474,7 @@ async def test_model_group_affinity_config_does_not_disable_global_encrypted_con
         },
         target_deployment,
     ]
-    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-        "deployment-b", "rs_test"
-    )
+    encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-b", "rs_test")
     request_kwargs = {
         "input": [{"type": "reasoning", "id": encoded_id}],
         "litellm_metadata": {},
@@ -1600,15 +1536,9 @@ async def test_model_group_encrypted_content_affinity_overrides_global_deploymen
 
     try:
         callbacks = router.optional_callbacks or []
-        deployment_callback = next(
-            cb for cb in callbacks if isinstance(cb, DeploymentAffinityCheck)
-        )
-        encrypted_content_callback = next(
-            cb for cb in callbacks if isinstance(cb, EncryptedContentAffinityCheck)
-        )
-        assert callbacks.index(encrypted_content_callback) < callbacks.index(
-            deployment_callback
-        )
+        deployment_callback = next(cb for cb in callbacks if isinstance(cb, DeploymentAffinityCheck))
+        encrypted_content_callback = next(cb for cb in callbacks if isinstance(cb, EncryptedContentAffinityCheck))
+        assert callbacks.index(encrypted_content_callback) < callbacks.index(deployment_callback)
         assert encrypted_content_callback.enable_global_affinity is False
 
         cache_key = DeploymentAffinityCheck.get_affinity_cache_key(
@@ -1620,9 +1550,7 @@ async def test_model_group_encrypted_content_affinity_overrides_global_deploymen
             value={"model_id": "deployment-a"},
             ttl=60,
         )
-        encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id(
-            "deployment-b", "rs_test"
-        )
+        encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-b", "rs_test")
         request_kwargs = {
             "input": [
                 {
@@ -1643,16 +1571,384 @@ async def test_model_group_encrypted_content_affinity_overrides_global_deploymen
         )
         assert after_deployment_affinity == [deployment_a, deployment_b]
 
-        after_encrypted_content_affinity = (
-            await encrypted_content_callback.async_filter_deployments(
-                model=model_group,
-                healthy_deployments=after_deployment_affinity,
-                messages=None,
-                request_kwargs=request_kwargs,
-            )
+        after_encrypted_content_affinity = await encrypted_content_callback.async_filter_deployments(
+            model=model_group,
+            healthy_deployments=after_deployment_affinity,
+            messages=None,
+            request_kwargs=request_kwargs,
         )
 
         assert after_encrypted_content_affinity == [deployment_b]
         assert request_kwargs.get("_encrypted_content_affinity_pinned") is True
     finally:
         router.discard()
+
+
+@pytest.mark.asyncio
+async def test_encrypted_content_affinity_pins_anthropic_messages_replayed_through_the_bridge():
+    """
+    Claude Code behind /v1/messages replays the encrypted reasoning the bridge packed
+    into a thinking block's signature (or a redacted block's data). The pin has to be
+    read from those blocks because the bridge builds the Responses `input` only after
+    the router has picked a deployment.
+    """
+    check = EncryptedContentAffinityCheck()
+    deployments = [
+        {"model_info": {"id": "openai-org-a"}, "litellm_params": {"model": "openai/gpt-5.1"}},
+        {"model_info": {"id": "openai-org-b"}, "litellm_params": {"model": "openai/gpt-5.1"}},
+    ]
+    request_kwargs = {"model": "gpt-5.1"}
+
+    pinned = await check.async_filter_deployments(
+        model="gpt-5.1",
+        healthy_deployments=deployments,
+        messages=_bridge_replayed_anthropic_messages(minted_by="openai-org-b"),
+        request_kwargs=request_kwargs,
+    )
+
+    assert [d["model_info"]["id"] for d in pinned] == ["openai-org-b"]
+    assert request_kwargs["_encrypted_content_affinity_pinned"] is True
+
+
+def _bridge_replayed_anthropic_messages(minted_by: str) -> list:
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA_turn_one", minted_by)
+    return [
+        {"role": "user", "content": "Solve the zebra puzzle"},
+        {
+            "role": "assistant",
+            "content": [
+                {"type": "thinking", "thinking": "Anthropic minted this one", "signature": "ErcCCpIBCBEYAipA"},
+                {"type": "redacted_thinking", "data": f"litellm_encrypted_reasoning:{wrapped}"},
+                {
+                    "type": "thinking",
+                    "thinking": "The bridge packed this one",
+                    "signature": f"litellm_encrypted_reasoning:{wrapped}",
+                },
+                {"type": "text", "text": "The zebra owner lives in the green house."},
+            ],
+        },
+        {"role": "user", "content": "And who drinks water?"},
+    ]
+
+
+@pytest.mark.asyncio
+async def test_encrypted_content_affinity_strips_bridge_reasoning_from_messages_routed_to_another_group():
+    """
+    The /v1/messages twin of the tier-change case: the routed group holds no deployment
+    of the org that minted the reasoning, so the bridge-tagged blocks are dropped whole
+    and the request dispatches to the routed pool. No unsigned thinking block may be left
+    behind: Anthropic and Bedrock reject a thinking block with a missing signature the
+    same way they reject a foreign one.
+    """
+    originating = _make_originating_mock(None, "key-a", model_name="gpt-reasoning-tier")
+    mock_router = _make_router_mock_with_cooldown(
+        originating, cooldown_entries=[], routed_group_model_ids=["openai-org-b"]
+    )
+    check = EncryptedContentAffinityCheck(router=mock_router)
+    routed_pool = [{"model_info": {"id": "openai-org-b"}, "litellm_params": {"model": "openai/gpt-5-nano"}}]
+    messages = _bridge_replayed_anthropic_messages(minted_by="openai-org-a")
+    assistant_content = messages[1]["content"]
+    request_kwargs = {"model": "gpt-5.1"}
+
+    result = await check.async_filter_deployments(
+        model="gpt-simple-tier",
+        healthy_deployments=routed_pool,
+        messages=messages,
+        request_kwargs=request_kwargs,
+    )
+
+    assert result is routed_pool
+    assert "_encrypted_content_affinity_pinned" not in request_kwargs
+    assert messages[1]["content"] is assistant_content
+    assert assistant_content == [
+        {"type": "thinking", "thinking": "Anthropic minted this one", "signature": "ErcCCpIBCBEYAipA"},
+        {"type": "text", "text": "The zebra owner lives in the green house."},
+    ]
+    assert all(block["signature"] for block in assistant_content if block["type"] == "thinking")
+
+
+class TestStripEncryptedReasoningFromInput:
+    def test_keeps_summary_and_drops_encrypted_content_and_id(self):
+        wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA-blob", "deployment-a")
+        encoded_id = ResponsesAPIRequestUtils._build_encrypted_item_id("deployment-a", "rs_1")
+        request_input = [
+            {"role": "user", "content": "first turn"},
+            {
+                "type": "reasoning",
+                "id": encoded_id,
+                "encrypted_content": wrapped,
+                "summary": [{"type": "summary_text", "text": "thought about it"}],
+            },
+            {"type": "reasoning", "id": encoded_id, "encrypted_content": wrapped},
+            {"type": "reasoning", "encrypted_content": wrapped, "summary": []},
+            {"type": "message", "id": "msg_1", "role": "assistant", "content": "hi"},
+            {"role": "user", "content": "second turn"},
+        ]
+        ResponsesAPIRequestUtils.strip_encrypted_reasoning_from_input(request_input)
+        assert request_input == [
+            {"role": "user", "content": "first turn"},
+            {
+                "type": "reasoning",
+                "summary": [{"type": "summary_text", "text": "thought about it"}],
+            },
+            {"type": "message", "id": "msg_1", "role": "assistant", "content": "hi"},
+            {"role": "user", "content": "second turn"},
+        ]
+
+    def test_keeps_string_form_summary_when_stripping(self):
+        wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA-blob", "deployment-a")
+        request_input = [
+            {"type": "reasoning", "encrypted_content": wrapped, "summary": "plain string thought"},
+            {
+                "type": "reasoning",
+                "encrypted_content": wrapped,
+                "content": [{"type": "output_text", "text": "in content"}],
+            },
+            {"type": "reasoning", "encrypted_content": wrapped, "summary": "", "content": []},
+        ]
+        ResponsesAPIRequestUtils.strip_encrypted_reasoning_from_input(request_input)
+        assert request_input == [
+            {"type": "reasoning", "summary": "plain string thought"},
+            {"type": "reasoning", "content": [{"type": "output_text", "text": "in content"}]},
+        ]
+
+    def test_leaves_input_untouched_when_no_encrypted_reasoning(self):
+        request_input = [
+            {"role": "user", "content": "first turn"},
+            {"type": "reasoning", "summary": [{"type": "summary_text", "text": "no blob here"}]},
+            {"role": "user", "content": "second turn"},
+        ]
+        before = [dict(item) for item in request_input]
+        ResponsesAPIRequestUtils.strip_encrypted_reasoning_from_input(request_input)
+        assert request_input == before
+
+
+def _cross_group_request_kwargs():
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA-blob", "deployment-a")
+    return {
+        "litellm_metadata": {},
+        "input": [
+            {"role": "user", "content": "ZEBRA: why is the sky blue?"},
+            {
+                "type": "reasoning",
+                "encrypted_content": wrapped,
+                "summary": [{"type": "summary_text", "text": "scattering"}],
+            },
+            {"type": "message", "role": "assistant", "content": "Rayleigh scattering."},
+            {"role": "user", "content": "KIWI: and sunsets?"},
+        ],
+    }
+
+
+@pytest.mark.asyncio
+async def test_affinity_strips_encrypted_reasoning_when_routed_to_another_model_group():
+    """
+    An auto-router tier change (or a model switch with no boundary peer): the
+    routed pool holds no deployment of the origin's model group. The origin is
+    healthy, so a 503 would be wrong; the follow-up dispatches to the routed
+    pool with the origin's encrypted reasoning stripped and its summary kept.
+    """
+    from litellm.router_utils.pre_call_checks.encrypted_content_affinity_check import (
+        EncryptedContentAffinityCheck,
+    )
+
+    originating = _make_originating_mock(None, "key-a", model_name="gpt-reasoning-tier")
+    mock_router = _make_router_mock_with_cooldown(
+        originating, cooldown_entries=[], routed_group_model_ids=["deployment-b"]
+    )
+    check = EncryptedContentAffinityCheck(router=mock_router)
+    routed_pool = [
+        {
+            "model_info": {"id": "deployment-b"},
+            "model_name": "gpt-simple-tier",
+            "litellm_params": {
+                "api_base": "https://gateway.example/v1",
+                "api_key": "key-b",
+                "model": "openai/gpt-5-nano",
+            },
+        }
+    ]
+    request_kwargs = _cross_group_request_kwargs()
+    original_input = request_kwargs["input"]
+
+    result = await check.async_filter_deployments(
+        model="gpt-simple-tier",
+        healthy_deployments=routed_pool,
+        messages=None,
+        request_kwargs=request_kwargs,
+    )
+
+    assert result is routed_pool
+    assert "_encrypted_content_affinity_pinned" not in request_kwargs
+    assert request_kwargs["litellm_metadata"]["encrypted_content_affinity_enabled"] is True
+    assert request_kwargs["input"] is original_input
+    assert [item.get("type") or item["role"] for item in original_input] == [
+        "user",
+        "reasoning",
+        "message",
+        "user",
+    ]
+    assert original_input[1] == {
+        "type": "reasoning",
+        "summary": [{"type": "summary_text", "text": "scattering"}],
+    }
+    assert not any(isinstance(item, dict) and item.get("encrypted_content") for item in original_input)
+
+
+@pytest.mark.asyncio
+async def test_affinity_fails_fast_within_the_origins_own_group():
+    """
+    Negative class for the tier-change discriminator: the routed group IS the
+    origin's group (a same-group cooldown, not a tier change), so even with a
+    healthy non-origin sibling that cannot decrypt the content, the request
+    still fails fast and the encrypted reasoning is left intact rather than
+    stripped. Preserves the LIT-3051 cooldown contract.
+    """
+    from litellm.exceptions import ServiceUnavailableError
+    from litellm.router_utils.pre_call_checks.encrypted_content_affinity_check import (
+        EncryptedContentAffinityCheck,
+    )
+
+    originating = _make_originating_mock(
+        "https://account-a.openai.azure.com/", "key-a", model_name="gpt-reasoning-tier"
+    )
+    mock_router = _make_router_mock_with_cooldown(
+        originating, cooldown_entries=[], routed_group_model_ids=["deployment-a", "deployment-a2"]
+    )
+    check = EncryptedContentAffinityCheck(router=mock_router)
+    sibling_pool = [
+        {
+            "model_info": {"id": "deployment-a2"},
+            "model_name": "gpt-reasoning-tier",
+            "litellm_params": {
+                "api_base": "https://account-a2.openai.azure.com/",
+                "api_key": "key-a2",
+                "model": "azure/gpt-5.4",
+            },
+        }
+    ]
+    request_kwargs = _cross_group_request_kwargs()
+
+    with pytest.raises(ServiceUnavailableError):
+        await check.async_filter_deployments(
+            model="gpt-reasoning-tier",
+            healthy_deployments=sibling_pool,
+            messages=None,
+            request_kwargs=request_kwargs,
+        )
+
+    assert request_kwargs["input"][1].get("encrypted_content")
+
+
+@pytest.mark.asyncio
+async def test_affinity_does_not_strip_when_group_is_spelled_differently_but_same_by_id():
+    """
+    The discriminator must key on deployment-id membership, not on the model-group
+    name string. Here the origin's configured group is spelled ``openai/gpt-5.4-mini``
+    while the routed group is the canonical ``gpt-5.4-mini``: same group, different
+    spelling. A name compare (``originating.model_name != model``) would read this as
+    a tier change and strip the reasoning it did not have to. Because the origin's id
+    is a member of the routed group, this is a same-group cooldown instead: the request
+    fails fast and the encrypted reasoning is left intact.
+    """
+    from litellm.exceptions import ServiceUnavailableError
+    from litellm.router_utils.pre_call_checks.encrypted_content_affinity_check import (
+        EncryptedContentAffinityCheck,
+    )
+
+    originating = _make_originating_mock(None, "key-a", model_name="openai/gpt-5.4-mini")
+    mock_router = _make_router_mock_with_cooldown(
+        originating, cooldown_entries=[], routed_group_model_ids=["deployment-mini-a", "deployment-mini-b"]
+    )
+    check = EncryptedContentAffinityCheck(router=mock_router)
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA-blob", "deployment-mini-a")
+    sibling_pool = [
+        {
+            "model_info": {"id": "deployment-mini-b"},
+            "model_name": "gpt-5.4-mini",
+            "litellm_params": {
+                "api_base": "https://gateway.example/v1",
+                "api_key": "key-b",
+                "model": "openai/gpt-5.4-mini",
+            },
+        }
+    ]
+    request_kwargs = {
+        "litellm_metadata": {},
+        "input": [
+            {"role": "user", "content": "why is the sky blue?"},
+            {
+                "type": "reasoning",
+                "encrypted_content": wrapped,
+                "summary": [{"type": "summary_text", "text": "scattering"}],
+            },
+            {"role": "user", "content": "and sunsets?"},
+        ],
+    }
+
+    with pytest.raises(ServiceUnavailableError):
+        await check.async_filter_deployments(
+            model="gpt-5.4-mini",
+            healthy_deployments=sibling_pool,
+            messages=None,
+            request_kwargs=request_kwargs,
+        )
+
+    assert request_kwargs["input"][1].get("encrypted_content")
+
+
+@pytest.mark.asyncio
+async def test_affinity_honors_router_candidate_ids_for_team_and_pattern_routes():
+    """
+    The exact `model_name` index does not include team-public or pattern routes, so a
+    same-group cooldown reached only through one of those would be misread as a tier change
+    and stripped. The check asks the router for the candidate ids it resolves for the route
+    (`get_candidate_model_ids_for_route`), which covers those paths, rather than the bare
+    index. Here that set marks the origin as a candidate, so the request fails fast with its
+    reasoning intact, and the routed group and team are passed through to the router.
+    """
+    from litellm.exceptions import ServiceUnavailableError
+    from litellm.router_utils.pre_call_checks.encrypted_content_affinity_check import (
+        EncryptedContentAffinityCheck,
+    )
+
+    originating = _make_originating_mock(None, "key-a", model_name="model_name_teamA_uuid")
+    mock_router = _make_router_mock_with_cooldown(
+        originating, cooldown_entries=[], routed_group_model_ids=["deployment-team-a", "deployment-team-b"]
+    )
+    check = EncryptedContentAffinityCheck(router=mock_router)
+    wrapped = ResponsesAPIRequestUtils._wrap_encrypted_content_with_model_id("gAAAAA-blob", "deployment-team-a")
+    sibling_pool = [
+        {
+            "model_info": {"id": "deployment-team-b"},
+            "model_name": "team-public-model",
+            "litellm_params": {
+                "api_base": "https://gateway.example/v1",
+                "api_key": "key-b",
+                "model": "openai/gpt-5.4-mini",
+            },
+        }
+    ]
+    request_kwargs = {
+        "litellm_metadata": {"user_api_key_team_id": "teamA"},
+        "input": [
+            {"role": "user", "content": "why is the sky blue?"},
+            {
+                "type": "reasoning",
+                "encrypted_content": wrapped,
+                "summary": [{"type": "summary_text", "text": "scattering"}],
+            },
+            {"role": "user", "content": "and sunsets?"},
+        ],
+    }
+
+    with pytest.raises(ServiceUnavailableError):
+        await check.async_filter_deployments(
+            model="team-public-model",
+            healthy_deployments=sibling_pool,
+            messages=None,
+            request_kwargs=request_kwargs,
+        )
+
+    assert request_kwargs["input"][1].get("encrypted_content")
+    mock_router.get_candidate_model_ids_for_route.assert_called_once_with(model="team-public-model", team_id="teamA")
diff --git a/tests/test_litellm/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py b/tests/test_litellm/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py
index 030bdfe03e9..333e7b2ff31 100644
--- a/tests/test_litellm/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py
+++ b/tests/test_litellm/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py
@@ -477,3 +477,65 @@ async def test_wildcard_route_resolves_underlying_model_minimum(local_model_cost
 
     assert deployments[0]["litellm_params"]["model"] == "anthropic/claude-opus-4-6"
     assert _get_min_token_count_for_deployments(deployments) == 4096
+
+
+@pytest.mark.asyncio
+async def test_async_filter_deployments_counts_the_prompt_off_the_event_loop():
+    from tests.large_text import text
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+        assert_loop_stayed_free,
+        timed_with_loop_lags,
+        warm_tokenizer,
+    )
+
+    warm_tokenizer("anthropic/claude-fable-5")
+    check = PromptCachingDeploymentCheck(cache=DualCache())
+    deployments = _deployments("anthropic/claude-fable-5")
+    messages = cast(List[AllMessageValues], [{"role": "user", "content": text * 100}])
+
+    result, took, lags = await timed_with_loop_lags(
+        lambda: check.async_filter_deployments(
+            model=MODEL_GROUP_ALIAS, healthy_deployments=deployments, messages=messages
+        )
+    )
+
+    assert result == deployments
+    assert_loop_stayed_free(took, lags)
+
+
+@pytest.mark.asyncio
+async def test_async_log_success_event_counts_the_prompt_off_the_event_loop():
+    from tests.large_text import text
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+        assert_loop_stayed_free,
+        timed_with_loop_lags,
+        warm_tokenizer,
+    )
+
+    warm_tokenizer("anthropic/claude-fable-5")
+    cache = DualCache()
+    check = PromptCachingDeploymentCheck(cache=cache)
+    messages = cast(
+        List[AllMessageValues],
+        [{"role": "user", "content": [{"type": "text", "text": text * 100, "cache_control": {"type": "ephemeral"}}]}],
+    )
+    standard_logging_object = {
+        "call_type": "acompletion",
+        "model": "anthropic/claude-fable-5",
+        "messages": messages,
+        "model_id": "dep-1",
+    }
+
+    _, took, lags = await timed_with_loop_lags(
+        lambda: check.async_log_success_event(
+            kwargs={"standard_logging_object": standard_logging_object},
+            response_obj=None,
+            start_time=None,
+            end_time=None,
+        )
+    )
+
+    assert await PromptCachingCache(cache=cache).async_get_model_id(messages=messages, tools=None) == {
+        "model_id": "dep-1"
+    }
+    assert_loop_stayed_free(took, lags)
diff --git a/tests/test_litellm/router_utils/test_health_state_cache.py b/tests/test_litellm/router_utils/test_health_state_cache.py
index ffd031f9b7d..aa976bb1002 100644
--- a/tests/test_litellm/router_utils/test_health_state_cache.py
+++ b/tests/test_litellm/router_utils/test_health_state_cache.py
@@ -7,6 +7,7 @@ import time
 import pytest
 
 from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import RedisCircuitBreakerOpenError
 from litellm.router_utils.health_state_cache import DeploymentHealthCache
 
 
@@ -145,8 +146,11 @@ class _SharedRedisFake:
     def __init__(self):
         self.store = {}
         self.fail_get = False
+        self.breaker_open = False
 
     def get_cache(self, key, parent_otel_span=None, **kwargs):
+        if self.breaker_open:
+            raise RedisCircuitBreakerOpenError("Redis circuit breaker is open - skipping get_cache")
         if self.fail_get:
             return None  # RedisCache.get_cache swallows connection errors and returns None
         return self.store.get(key)
@@ -192,3 +196,26 @@ def test_failed_redis_read_falls_back_to_local_copy():
         {"prod-bad": {"is_healthy": False, "timestamp": time.time(), "reason": "check_failed"}}
     )
     assert set(redis_fake.store[DeploymentHealthCache.CACHE_KEY]) == {"prod-bad", "internal-bad"}
+
+
+def test_open_circuit_breaker_read_still_merges_into_local_copy(caplog):
+    """A read refused by the open breaker is a miss, so the merge and local write still happen quietly."""
+    redis_fake = _SharedRedisFake()
+    pod_a = DeploymentHealthCache(cache=DualCache(redis_cache=redis_fake), staleness_threshold=60.0)
+    pod_b = DeploymentHealthCache(cache=DualCache(redis_cache=redis_fake), staleness_threshold=60.0)
+    pod_a.set_deployment_health_states(
+        {"prod-bad": {"is_healthy": False, "timestamp": time.time(), "reason": "check_failed"}}
+    )
+    pod_b.set_deployment_health_states(
+        {"internal-bad": {"is_healthy": False, "timestamp": time.time(), "reason": "timeout"}}
+    )
+    pod_a.set_deployment_health_states(
+        {"prod-bad": {"is_healthy": False, "timestamp": time.time(), "reason": "check_failed"}}
+    )
+    redis_fake.breaker_open = True
+    with caplog.at_level("ERROR"):
+        pod_a.set_deployment_health_states(
+            {"prod-new-bad": {"is_healthy": False, "timestamp": time.time(), "reason": "check_failed"}}
+        )
+    assert caplog.records == []
+    assert pod_a.get_unhealthy_deployment_ids() == {"prod-bad", "internal-bad", "prod-new-bad"}
diff --git a/tests/test_litellm/router_utils/test_router_utils_common_utils.py b/tests/test_litellm/router_utils/test_router_utils_common_utils.py
index 30f658d7ea2..ac18b4889dd 100644
--- a/tests/test_litellm/router_utils/test_router_utils_common_utils.py
+++ b/tests/test_litellm/router_utils/test_router_utils_common_utils.py
@@ -12,6 +12,7 @@ from litellm.router_utils.common_utils import (
     add_model_file_id_mappings,
     filter_team_based_models,
     filter_web_search_deployments,
+    provider_for_generic_call,
     resolve_model_group_alias,
     truncate_fallback_error_detail,
     PROVIDER_SCOPED_CREDENTIAL_PARAMS,
@@ -756,3 +757,20 @@ class TestWarnOnProviderCredentialMismatch:
             )
             is None
         )
+
+
+@pytest.mark.parametrize(
+    ("litellm_params", "expected"),
+    [
+        ({"model": "azure_ai/gpt-5.4-mini", "custom_llm_provider": "azure"}, "azure"),
+        ({"model": "azure_ai/gpt-5.4-mini", "api_base": "https://my-resource.openai.azure.com"}, "azure_ai"),
+        ({"model": "cohere/command-r"}, "cohere"),
+        ({"model": "gpt-5.4-mini"}, "openai"),
+        ({"model": "no-provider-knows-this-model"}, None),
+        ({"api_base": "https://my-resource.openai.azure.com"}, None),
+    ],
+    ids=["declared_wins", "prefix_beats_host_flip", "prefix_beats_cohere_chat_flip", "unprefixed_inferred", "unknown", "no_model"],
+)
+def test_provider_for_generic_call(litellm_params, expected, monkeypatch):
+    monkeypatch.setenv("AZURE_AI_API_BASE", "https://unrelated.openai.azure.com")
+    assert provider_for_generic_call(litellm_params) == expected
diff --git a/tests/test_litellm/rust_bridge/test_token_counter.py b/tests/test_litellm/rust_bridge/test_token_counter.py
new file mode 100644
index 00000000000..2df91204390
--- /dev/null
+++ b/tests/test_litellm/rust_bridge/test_token_counter.py
@@ -0,0 +1,242 @@
+"""Tests for the Rust input token counter bridge.
+
+The native factory is dependency-injected through ``TOKEN_COUNTER.override``
+so the fallback cases run without the compiled extension present. The parity
+cases need the extension and are skipped when it is not built.
+"""
+
+from __future__ import annotations
+
+import json
+from typing import Final
+
+import pytest
+
+import litellm
+from litellm.proxy.spend_tracking.budget_reservation import _count_input_tokens
+from litellm.rust_bridge import bindings, configuration
+from litellm.rust_bridge import token_counter as bridge
+
+MODEL: Final = "claude-sonnet-4-5-20250929"
+BODY: Final = json.dumps({"model": MODEL, "messages": [{"role": "user", "content": "hello"}]}).encode()
+
+
+class _FakeDeclined(Exception):
+    pass
+
+
+class _FakeUpstream(Exception):
+    pass
+
+
+class _FakeNative:
+    RustBridgeDeclined = _FakeDeclined
+    RustUpstreamError = _FakeUpstream
+
+
+class _RecordingCounter:
+    def __init__(self, tokenizer_json: str) -> None:
+        self.tokenizer_json = tokenizer_json
+        self.bodies: list[bytes] = []
+
+    async def acount_request(self, body: bytes) -> object:
+        self.bodies.append(body)
+        return {"model": MODEL, "input_tokens": 42}
+
+
+class _DecliningCounter:
+    def __init__(self, tokenizer_json: str) -> None:
+        pass
+
+    async def acount_request(self, body: bytes) -> object:
+        raise _FakeDeclined("request has no messages")
+
+
+class _FailingCounter:
+    def __init__(self, tokenizer_json: str) -> None:
+        pass
+
+    async def acount_request(self, body: bytes) -> object:
+        raise RuntimeError("encode failed")
+
+
+@pytest.fixture(autouse=True)
+def _reset_bridge(monkeypatch: pytest.MonkeyPatch):
+    bridge.TOKEN_COUNTER.reset()
+    bridge._anthropic_counter.cache_clear()
+    configuration.reset_rust_configuration()
+    monkeypatch.setattr(bindings, "get_native_bridge", lambda: _FakeNative())
+    yield
+    bridge.TOKEN_COUNTER.reset()
+    bridge._anthropic_counter.cache_clear()
+    configuration.reset_rust_configuration()
+
+
+@pytest.mark.asyncio
+async def test_disabled_bridge_never_constructs_a_counter() -> None:
+    constructed: list[str] = []
+
+    def factory(tokenizer_json: str) -> _RecordingCounter:
+        constructed.append(tokenizer_json)
+        return _RecordingCounter(tokenizer_json)
+
+    litellm.rust(False)
+    bridge.TOKEN_COUNTER.override(factory)
+
+    assert await bridge.count_anthropic_input_tokens(BODY) is None
+    assert constructed == []
+
+
+@pytest.mark.asyncio
+async def test_enabled_bridge_returns_typed_count_and_reuses_one_counter() -> None:
+    counters: list[_RecordingCounter] = []
+
+    def factory(tokenizer_json: str) -> _RecordingCounter:
+        counter = _RecordingCounter(tokenizer_json)
+        counters.append(counter)
+        return counter
+
+    litellm.rust(True)
+    bridge.TOKEN_COUNTER.override(factory)
+
+    first: Final = await bridge.count_anthropic_input_tokens(BODY)
+    second: Final = await bridge.count_anthropic_input_tokens(BODY)
+
+    assert first == bridge.InputTokenCount(model=MODEL, input_tokens=42)
+    assert second == first
+    assert len(counters) == 1
+    assert counters[0].bodies == [BODY, BODY]
+    assert json.loads(counters[0].tokenizer_json)["model"]["type"] == "BPE"
+
+
+@pytest.mark.asyncio
+async def test_missing_native_module_falls_back(monkeypatch: pytest.MonkeyPatch) -> None:
+    litellm.rust(True)
+    monkeypatch.setattr(bindings, "get_native_bridge", lambda: None)
+
+    assert await bridge.count_anthropic_input_tokens(BODY) is None
+
+
+@pytest.mark.asyncio
+async def test_declined_request_falls_back() -> None:
+    litellm.rust(True)
+    bridge.TOKEN_COUNTER.override(_DecliningCounter)
+
+    assert await bridge.count_anthropic_input_tokens(BODY) is None
+
+
+@pytest.mark.asyncio
+async def test_runtime_failure_falls_back() -> None:
+    litellm.rust(True)
+    bridge.TOKEN_COUNTER.override(_FailingCounter)
+
+    assert await bridge.count_anthropic_input_tokens(BODY) is None
+
+
+@pytest.mark.parametrize(
+    ("model", "expected"),
+    ((MODEL, True), ("claude-3-5-sonnet-20241022", False), ("gpt-4o", False), ("my-router-alias", False)),
+)
+def test_uses_anthropic_tokenizer_mirrors_python_tokenizer_selection(model: str, expected: bool) -> None:
+    assert bridge.uses_anthropic_tokenizer(model) is expected
+
+
+@pytest.mark.parametrize("flag", ("disable_hf_tokenizer_download", "disable_token_counter"))
+def test_uses_anthropic_tokenizer_respects_python_opt_outs(monkeypatch: pytest.MonkeyPatch, flag: str) -> None:
+    monkeypatch.setattr(litellm, flag, True)
+
+    assert bridge.uses_anthropic_tokenizer(MODEL) is False
+
+
+PARITY_REQUESTS: Final[tuple[dict[str, object], ...]] = (
+    {"model": MODEL, "messages": [{"role": "user", "content": "Hello, how are you today?"}]},
+    {
+        "model": MODEL,
+        "messages": [
+            {"role": "system", "content": "You are terse."},
+            {"role": "user", "name": "bob", "content": [{"type": "text", "text": "Summarize this."}]},
+            {"role": "assistant", "content": "Sure."},
+        ],
+    },
+    {
+        "model": MODEL,
+        "messages": [{"role": "user", "content": "weather in sf?"}],
+        "tools": [
+            {
+                "type": "function",
+                "function": {
+                    "name": "get_weather",
+                    "description": "Get weather",
+                    "parameters": {
+                        "type": "object",
+                        "properties": {
+                            "city": {"type": "string", "description": "City"},
+                            "unit": {"type": "string", "enum": ["c", "f"]},
+                        },
+                        "required": ["city"],
+                    },
+                },
+            }
+        ],
+        "tool_choice": {"type": "function", "function": {"name": "get_weather"}},
+    },
+    {
+        "model": MODEL,
+        "messages": [{"role": "user", "content": "x " * 20_000}],
+    },
+    {"model": MODEL, "prompt": "Write a haiku about ships.", "max_tokens": 20},
+    {"model": MODEL, "prompt": ["first prompt", "second prompt"]},
+    {
+        "model": MODEL,
+        "instructions": "be terse",
+        "input": [
+            {"role": "user", "content": [{"type": "input_text", "text": "Summarise caf\u00e9 menus \u2014 \"ok\"?\n"}]},
+            {"role": "assistant", "content": "Sure."},
+        ],
+    },
+    {"model": MODEL, "input": "a single embedding string"},
+    {"model": MODEL, "input": [[101, 2023, 5], [7]], "encoding_format": "float"},
+    {"model": MODEL, "query": "best harbour", "documents": ["doc one", {"text": "doc two", "title": "T", "n": 3}]},
+    {"model": MODEL, "messages": None, "prompt": "messages key wins even when null"},
+    {"prompt": "model comes from the route"},
+)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("request_body", PARITY_REQUESTS)
+async def test_native_count_matches_python_budget_counter(
+    monkeypatch: pytest.MonkeyPatch, request_body: dict[str, object]
+) -> None:
+    native: Final = pytest.importorskip("litellm.rust_bridge._native")
+    monkeypatch.setattr(bindings, "get_native_bridge", lambda: native)
+    litellm.rust(True)
+
+    rust_count: Final = await bridge.count_anthropic_input_tokens(json.dumps(request_body).encode())
+    python_count: Final = _count_input_tokens(request_body=request_body, model=MODEL)
+
+    assert rust_count is not None
+    assert rust_count.model == request_body.get("model")
+    assert rust_count.input_tokens == python_count
+
+
+DECLINED_REQUESTS: Final[tuple[dict[str, object], ...]] = (
+    {
+        "model": MODEL,
+        "messages": [{"role": "user", "content": [{"type": "image_url", "image_url": {"url": "data:image/png;base64,AA"}}]}],
+    },
+    {"model": MODEL, "prompt": 1.5},
+    {"model": MODEL, "documents": [{"score": 0.5}]},
+    {"model": MODEL, "file": "audio.mp3"},
+)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("request_body", DECLINED_REQUESTS)
+async def test_native_declines_shapes_python_prices_differently(
+    monkeypatch: pytest.MonkeyPatch, request_body: dict[str, object]
+) -> None:
+    native: Final = pytest.importorskip("litellm.rust_bridge._native")
+    monkeypatch.setattr(bindings, "get_native_bridge", lambda: native)
+    litellm.rust(True)
+
+    assert await bridge.count_anthropic_input_tokens(json.dumps(request_body).encode()) is None
diff --git a/tests/test_litellm/test_component_entrypoint.py b/tests/test_litellm/test_component_entrypoint.py
index 09837d2b233..0c2a533b8bc 100644
--- a/tests/test_litellm/test_component_entrypoint.py
+++ b/tests/test_litellm/test_component_entrypoint.py
@@ -38,12 +38,16 @@ _STUB_TEMPLATE = """#!/bin/sh
 _ENTRYPOINT_RE = re.compile(r"^ENTRYPOINT\s+(\[.*\])\s*$", re.MULTILINE)
 _CMD_RE = re.compile(r"^CMD\s+(\[.*\])\s*$", re.MULTILINE)
 _COPY_RE = re.compile(r"^COPY\s+(?!--from)(\S+)\s+(\S+)\s*$", re.MULTILINE)
-_APP_TARGET_RE = re.compile(r"(?:gateway|backend)\.main:app")
+_APP_TARGET_RE = re.compile(r"(?:gateway|backend)\.main:app|gateway\.launch")
 _TF_STRING_LOCAL_RE = re.compile(r'^\s*(\w+)\s*=\s*"((?:[^"\\]|\\.)*)"\s*$', re.MULTILINE)
 _TF_INTERPOLATION_RE = re.compile(r"\$\{(local|var)\.(\w+)\}")
 
 TERRAFORM_LAUNCH_SITES = {TERRAFORM_ECS: 2, TERRAFORM_CLOUDRUN: 2}
 TERRAFORM_VAR_STUBS = {"gateway_num_workers": "2"}
+COMPONENT_LAUNCHERS = {
+    "gateway": ("python", "-m", "gateway.launch"),
+    "backend": ("uvicorn", "backend.main:app"),
+}
 _MAX_INTERPOLATION_PASSES = 5
 
 
@@ -63,7 +67,7 @@ def _run_entrypoint(
     """Run `script` with stubbed executables on PATH and return the recorded lines."""
     bin_dir = tmp_path / "bin"
     bin_dir.mkdir(parents=True)
-    _write_stubs(bin_dir, ("ddtrace-run", "uvicorn", "litellm"))
+    _write_stubs(bin_dir, ("ddtrace-run", "uvicorn", "python", "litellm"))
     record = tmp_path / "record.txt"
 
     env = {
@@ -330,22 +334,63 @@ def test_entrypoint_script_has_no_carriage_returns() -> None:
 
 
 @pytest.mark.parametrize(
-    "dockerfile, app_target",
+    "dockerfile, launcher",
     [
-        (GATEWAY_DOCKERFILE, "gateway.main:app"),
-        (BACKEND_DOCKERFILE, "backend.main:app"),
+        (GATEWAY_DOCKERFILE, "python -m gateway.launch"),
+        (BACKEND_DOCKERFILE, "uvicorn backend.main:app"),
     ],
 )
-def test_component_images_launch_uvicorn_through_the_entrypoint(dockerfile: Path, app_target: str) -> None:
+def test_component_images_launch_uvicorn_through_the_entrypoint(dockerfile: Path, launcher: str) -> None:
     entrypoint = " ".join(_entrypoint_argv(dockerfile))
 
     assert IMAGE_ENTRYPOINT_PATH in entrypoint, f"{dockerfile} bypasses the ddtrace-aware entrypoint"
-    assert app_target in entrypoint
-    assert entrypoint.index(IMAGE_ENTRYPOINT_PATH) < entrypoint.index("uvicorn"), (
+    assert launcher in entrypoint
+    assert entrypoint.index(IMAGE_ENTRYPOINT_PATH) < entrypoint.index(launcher), (
         f"{dockerfile} must invoke uvicorn through the entrypoint, not the other way around"
     )
 
 
+@pytest.mark.parametrize(
+    "use_ddtrace, num_workers, expected_exec, expected_args",
+    [
+        (None, "4", "exec=python", "args=-m gateway.launch --workers 4 --host 0.0.0.0 --port 4000"),
+        (None, None, "exec=python", "args=-m gateway.launch --workers 1 --host 0.0.0.0 --port 4000"),
+        ("true", "4", "exec=ddtrace-run", "args=python -m gateway.launch --workers 4 --host 0.0.0.0 --port 4000"),
+    ],
+)
+def test_gateway_image_execs_the_supervisor_with_its_worker_count(
+    use_ddtrace: str | None, num_workers: str | None, expected_exec: str, expected_args: str, tmp_path: Path
+) -> None:
+    """Run the gateway image's ENTRYPOINT + CMD and record what the container execs.
+
+    The Dockerfile's `/app/...` script path is resolved to the checked-in script and `python`
+    is stubbed on PATH, so the assertion is on the argv `gateway.launch` receives, not on the
+    Dockerfile text.
+    """
+    entrypoint = tuple(
+        part.replace(IMAGE_ENTRYPOINT_PATH, str(COMPONENT_ENTRYPOINT)) for part in _entrypoint_argv(GATEWAY_DOCKERFILE)
+    )
+    bin_dir = tmp_path / "bin"
+    bin_dir.mkdir(parents=True)
+    _write_stubs(bin_dir, ("ddtrace-run", "python", "uvicorn"))
+    record = tmp_path / "record.txt"
+    overrides = {"USE_DDTRACE": use_ddtrace, "NUM_WORKERS": num_workers}
+    env = {
+        **{k: v for k, v in os.environ.items() if k not in ("DD_TRACE_OPENAI_ENABLED", *overrides)},
+        **{k: v for k, v in overrides.items() if v is not None},
+        "PATH": f"{bin_dir}{os.pathsep}{os.environ['PATH']}",
+        "RECORD": str(record),
+        "PYTHONPATH": PYTHONPATH_SENTINEL,
+    }
+
+    result = subprocess.run(
+        [*entrypoint, *_cmd_argv(GATEWAY_DOCKERFILE)], env=env, capture_output=True, text=True, check=False
+    )
+
+    assert result.returncode == 0, f"stdout={result.stdout} stderr={result.stderr}"
+    assert tuple(record.read_text().splitlines())[:2] == (expected_exec, expected_args)
+
+
 @pytest.mark.parametrize("dockerfile", [GATEWAY_DOCKERFILE, BACKEND_DOCKERFILE])
 def test_component_images_make_the_entrypoint_executable(dockerfile: Path) -> None:
     body = dockerfile.read_text()
@@ -367,17 +412,18 @@ def test_terraform_launch_command_matches_the_script_contract(
     implementations under the same environment and asserts they agree on which binary is exec'd
     and on whether the openai integration is disabled.
     """
-    app_target = f"{component}.main:app"
+    launcher = COMPONENT_LAUNCHERS[component]
+    app_target = " ".join(launcher[1:])
     command = _resolve_tf_local(terraform_file, f"{component}_launch_cmd")
 
     bin_dir = tmp_path / "bin"
     bin_dir.mkdir(parents=True)
-    _write_stubs(bin_dir, ("ddtrace-run", "uvicorn"))
+    _write_stubs(bin_dir, ("ddtrace-run", "uvicorn", "python"))
     from_terraform = _run_shell_command(command, bin_dir, tmp_path / "terraform.txt", use_ddtrace)
 
     from_script = _run_entrypoint(
         COMPONENT_ENTRYPOINT,
-        ("uvicorn", app_target),
+        launcher,
         use_ddtrace=use_ddtrace,
         tmp_path=tmp_path / "script",
     )
@@ -387,12 +433,14 @@ def test_terraform_launch_command_matches_the_script_contract(
     )
     assert from_terraform[2] == from_script[2], f"{terraform_file} disagrees with the script on the openai integration"
     assert app_target in from_terraform[1]
+    assert "gateway.main:app" not in from_terraform[1], f"{terraform_file} bypasses the gateway.launch supervisor"
 
     if use_ddtrace in TRUTHY_USE_DDTRACE:
         assert from_terraform[0] == "exec=ddtrace-run"
+        assert from_terraform[1].startswith(f"args={launcher[0]} ")
         assert from_terraform[2] == "DD_TRACE_OPENAI_ENABLED=False"
     else:
-        assert from_terraform[0] == "exec=uvicorn"
+        assert from_terraform[0] == f"exec={launcher[0]}"
         assert from_terraform[2] == "DD_TRACE_OPENAI_ENABLED=<unset>"
 
 
diff --git a/tests/test_litellm/test_cost_calculator.py b/tests/test_litellm/test_cost_calculator.py
index f8fa2231597..f610821e06a 100644
--- a/tests/test_litellm/test_cost_calculator.py
+++ b/tests/test_litellm/test_cost_calculator.py
@@ -18,6 +18,7 @@ from litellm.cost_calculator import (
     response_cost_calculator,
 )
 from litellm.types.llms.openai import OpenAIRealtimeStreamList
+from litellm.types.rerank import RerankResponse
 from litellm.types.utils import (
     CacheCreationTokenDetails,
     ModelInfo,
@@ -128,6 +129,22 @@ def test_completion_cost_uses_response_model_for_dynamic_routing(_local_model_co
     assert cost > 0, "Cost should be calculated using response model"
 
 
+def test_jina_rerank_bills_total_tokens_at_input_rate_only(_local_model_cost_map):
+    response: Final = RerankResponse(
+        id="rerank-1",
+        results=[{"index": 0, "relevance_score": 0.9}],
+        meta={"billed_units": {"total_tokens": 1000}},
+    )
+
+    cost: Final = completion_cost(
+        completion_response=response,
+        model="jina_ai/jina-reranker-v2-base-multilingual",
+        call_type="rerank",
+    )
+
+    assert cost == pytest.approx(1000 * 5e-08)
+
+
 def test_cost_calculator_with_response_cost_in_additional_headers():
     class MockResponse(BaseModel):
         _hidden_params = {
@@ -3736,6 +3753,112 @@ def test_completion_cost_logs_reasoning_and_cache_breakdown(_local_model_cost_ma
     assert logging_obj.cost_breakdown["cache_read_cost"] == pytest.approx(100 * 3e-08)
 
 
+def test_completion_cost_logs_the_rates_it_billed_at(monkeypatch):
+    """A caller reporting the cost lines beside their per-token rates reads both off this one call.
+    completion_cost infers the provider, and xai's inclusive tier thresholds put a request sitting
+    exactly on 200k at the tier rate, which a lookup made without that inferred provider would miss.
+    """
+    from datetime import datetime
+
+    from litellm.litellm_core_utils.litellm_logging import Logging
+
+    monkeypatch.setitem(
+        litellm.model_cost,
+        "xai/tiered-model",
+        {
+            "input_cost_per_token": 3e-6,
+            "output_cost_per_token": 15e-6,
+            "cache_read_input_token_cost": 3e-7,
+            "input_cost_per_token_above_200k_tokens": 6e-6,
+            "output_cost_per_token_above_200k_tokens": 3e-5,
+            "cache_read_input_token_cost_above_200k_tokens": 6e-7,
+            "litellm_provider": "xai",
+            "mode": "chat",
+        },
+    )
+    logging_obj = Logging(
+        model="xai/tiered-model",
+        messages=[{"role": "user", "content": "Hello"}],
+        stream=False,
+        call_type="completion",
+        start_time=datetime.now(),
+        litellm_call_id="billed-rates",
+        function_id="f",
+    )
+    usage = Usage(
+        prompt_tokens=200_000,
+        completion_tokens=1_000,
+        total_tokens=201_000,
+        prompt_tokens_details=PromptTokensDetailsWrapper(cached_tokens=100_000),
+    )
+
+    litellm.completion_cost(
+        completion_response=ModelResponse(model="xai/tiered-model", usage=usage),
+        model="xai/tiered-model",
+        custom_llm_provider=None,
+        litellm_logging_obj=logging_obj,
+    )
+
+    rates = logging_obj.billed_token_rates
+    assert rates is not None
+    assert rates.input_cost_per_token == pytest.approx(6e-6)
+    assert rates.cache_read_input_token_cost == pytest.approx(6e-7)
+    assert logging_obj.cost_breakdown["cache_read_cost"] == pytest.approx(
+        100_000 * rates.cache_read_input_token_cost
+    )
+    assert logging_obj.cost_breakdown["output_cost"] == pytest.approx(1_000 * rates.output_cost_per_token)
+
+
+def test_completion_cost_logs_cache_and_reasoning_breakdown_for_custom_pricing():
+    """
+    A custom-priced deployment bills cache tokens at its custom cache rates, but the
+    breakdown stored for the spend logs carried no cache or reasoning lines for it.
+    """
+    from datetime import datetime
+
+    from litellm.litellm_core_utils.litellm_logging import Logging
+    from litellm.types.utils import CompletionTokensDetailsWrapper, CostPerToken
+
+    logging_obj = Logging(
+        model="openai/onprem-model",
+        messages=[{"role": "user", "content": "Hello"}],
+        stream=False,
+        call_type="completion",
+        start_time=datetime.now(),
+        litellm_call_id="custom-pricing-breakdown",
+        function_id="f",
+    )
+    response = ModelResponse(
+        model="openai/onprem-model",
+        usage=Usage(
+            prompt_tokens=1000,
+            completion_tokens=500,
+            total_tokens=1500,
+            prompt_tokens_details=PromptTokensDetailsWrapper(cached_tokens=800, cache_creation_tokens=100),
+            completion_tokens_details=CompletionTokensDetailsWrapper(reasoning_tokens=200),
+        ),
+    )
+
+    total = completion_cost(
+        completion_response=response,
+        model="openai/onprem-model",
+        custom_llm_provider="openai",
+        custom_cost_per_token=CostPerToken(
+            input_cost_per_token=1e-6,
+            output_cost_per_token=2e-6,
+            cache_read_input_token_cost=1e-7,
+            cache_creation_input_token_cost=1.25e-6,
+        ),
+        litellm_logging_obj=logging_obj,
+    )
+
+    assert logging_obj.cost_breakdown is not None
+    assert logging_obj.cost_breakdown["cache_read_cost"] == pytest.approx(800 * 1e-7)
+    assert logging_obj.cost_breakdown["cache_creation_cost"] == pytest.approx(100 * 1.25e-6)
+    assert logging_obj.cost_breakdown["reasoning_cost"] == pytest.approx(200 * 2e-6)
+    assert total == pytest.approx(100 * 1e-6 + 800 * 1e-7 + 100 * 1.25e-6 + 500 * 2e-6)
+
+
 def test_cost_per_token_per_second_pricing(monkeypatch):
     """
     Models priced by duration (input/output_cost_per_second) with no per-token rates
diff --git a/tests/test_litellm/test_lint_workflow_diff_gates.py b/tests/test_litellm/test_lint_workflow_diff_gates.py
new file mode 100644
index 00000000000..62e67cdaaab
--- /dev/null
+++ b/tests/test_litellm/test_lint_workflow_diff_gates.py
@@ -0,0 +1,54 @@
+from __future__ import annotations
+
+import re
+import shlex
+import subprocess
+from pathlib import Path
+from typing import Final
+
+import pytest
+
+WORKFLOW: Final = Path(__file__).resolve().parents[2] / ".github" / "workflows" / "test-linting.yml"
+DIFF_GATE: Final = re.compile(r'git diff --name-only --diff-filter=\w+ "\$GATE_BASE_SHA" HEAD -- (.+?) \|')
+GATES: Final = tuple(tuple(shlex.split(gate.group(1))) for gate in DIFF_GATE.finditer(WORKFLOW.read_text()))
+
+
+def _git(cwd: Path, *args: str) -> str:
+    return subprocess.run(["git", *args], cwd=cwd, check=True, capture_output=True, text=True).stdout
+
+
+def _scoped_root(pathspec: str) -> str:
+    return re.sub(r"^:\([^)]*\)", "", pathspec).split("*", 1)[0]
+
+
+def _changed_files_selected_by(tmp_path: Path, pathspecs: tuple[str, ...], files: tuple[str, ...]) -> frozenset[str]:
+    _git(tmp_path, "init", "-q", "-b", "main")
+    _git(tmp_path, "config", "user.email", "t@t")
+    _git(tmp_path, "config", "user.name", "t")
+    _git(tmp_path, "commit", "-q", "--allow-empty", "-m", "base")
+    for name in files:
+        target = tmp_path / name
+        target.parent.mkdir(parents=True, exist_ok=True)
+        target.write_text("x = 1\n")
+    _git(tmp_path, "add", "-A")
+    _git(tmp_path, "commit", "-qm", "change")
+    return frozenset(
+        _git(tmp_path, "diff", "--name-only", "--diff-filter=ACMRD", "HEAD~1", "HEAD", "--", *pathspecs).split()
+    )
+
+
+def test_workflow_still_carries_the_ruff_format_and_e2e_basedpyright_diff_gates() -> None:
+    assert frozenset(_scoped_root(gate[0]) for gate in GATES) == frozenset({"litellm/", "tests/e2e/"})
+
+
+@pytest.mark.parametrize("pathspecs", GATES, ids=" ".join)
+def test_diff_gate_selects_top_level_and_nested_python_files_only(tmp_path: Path, pathspecs: tuple[str, ...]) -> None:
+    root = _scoped_root(pathspecs[0])
+    top_level = f"{root}top_level_module.py"
+    nested = f"{root}pkg/sub/nested_module.py"
+    selected = _changed_files_selected_by(
+        tmp_path,
+        pathspecs,
+        (top_level, nested, f"{root}notes.md", "elsewhere/top_level_module.py", "elsewhere/pkg/nested_module.py"),
+    )
+    assert selected == frozenset({top_level, nested})
diff --git a/tests/test_litellm/test_main.py b/tests/test_litellm/test_main.py
index 038df3656fe..f71225c6fc5 100644
--- a/tests/test_litellm/test_main.py
+++ b/tests/test_litellm/test_main.py
@@ -120,7 +120,7 @@ def test_completion_missing_role(openai_api_response):
     print(f"openai_api_response: {openai_api_response}")
 
     with patch.object(
-        client.chat.completions.with_raw_response, "create", mock_raw_response
+        client.chat.completions.with_raw_response, "create", MagicMock(return_value=mock_raw_response)
     ) as mock_create:
         litellm.completion(
             model="gpt-4o-mini",
@@ -1367,6 +1367,78 @@ def test_gpt_5_4_responses_bridge_preserves_reasoning_summary_dict(
     }
 
 
+@pytest.mark.parametrize("reasoning_effort", ["high", {"effort": "high"}])
+def test_responses_bridge_preserves_reasoning_effort_with_drop_params(
+    reasoning_effort,
+    restore_model_registry,
+    respx_mock: respx.MockRouter,
+    monkeypatch: pytest.MonkeyPatch,
+):
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    response_body: Final = {
+        "id": "resp_test",
+        "object": "response",
+        "created_at": 1734366691,
+        "status": "completed",
+        "model": "test-responses-bridge",
+        "output": [
+            {
+                "type": "message",
+                "id": "msg_1",
+                "status": "completed",
+                "role": "assistant",
+                "content": [{"type": "output_text", "text": "Done.", "annotations": []}],
+            }
+        ],
+        "parallel_tool_calls": True,
+        "usage": {
+            "input_tokens": 1,
+            "output_tokens": 1,
+            "total_tokens": 2,
+            "output_tokens_details": {"reasoning_tokens": 0},
+        },
+        "error": None,
+        "incomplete_details": None,
+        "instructions": None,
+        "metadata": None,
+        "temperature": None,
+        "tool_choice": "auto",
+        "tools": [],
+        "top_p": None,
+        "max_output_tokens": None,
+        "previous_response_id": None,
+        "reasoning": None,
+        "truncation": None,
+        "user": None,
+    }
+    response_route: Final = respx_mock.post("https://api.perplexity.ai/v1/responses").respond(json=response_body)
+    model: Final = "perplexity/test-responses-bridge"
+    litellm.register_model(
+        {
+            model: {
+                "litellm_provider": "perplexity",
+                "mode": "responses",
+                "supports_reasoning": False,
+                "input_cost_per_token": 0.0,
+                "output_cost_per_token": 0.0,
+            }
+        },
+        persist_across_reloads=False,
+    )
+
+    litellm.completion(
+        model=model,
+        messages=[{"role": "user", "content": "hello"}],
+        reasoning_effort=reasoning_effort,
+        drop_params=True,
+        api_key="fake-key",
+        api_base="https://api.perplexity.ai",
+    )
+
+    request_body: Final = json.loads(response_route.calls[0].request.content)
+    assert request_body["reasoning"] == {"effort": "high"}
+
+
 @pytest.mark.parametrize(
     "model, model_info, expected_model_param, expected_base_model_param",
     [
@@ -2322,6 +2394,280 @@ def test_image_edit_merges_headers_and_extra_headers():
     assert "extra_headers" not in handler_kwargs["image_edit_optional_request_params"]
 
 
+@pytest.mark.parametrize("metadata_key", ("metadata", "litellm_metadata"))
+@pytest.mark.parametrize("input_tokens", (51234, 0))
+def test_mock_completion_usage_reports_admission_input_tokens(metadata_key: str, input_tokens: int):
+    response = litellm.completion(
+        model="anthropic/claude-sonnet-5",
+        messages=[{"role": "user", "content": "hello"}],
+        mock_response="ok",
+        api_key="mock",
+        **{metadata_key: {"user_api_key_budget_reservation": {"reserved_cost": 1.0, "input_tokens": input_tokens}}},
+    )
+
+    assert response.usage.prompt_tokens == input_tokens
+    assert response.usage.total_tokens == input_tokens + response.usage.completion_tokens
+
+
+def test_mock_completion_usage_falls_back_to_default_without_admission_count():
+    response = litellm.completion(
+        model="anthropic/claude-sonnet-5",
+        messages=[{"role": "user", "content": "hello"}],
+        mock_response="ok",
+        api_key="mock",
+        metadata={"user_api_key_budget_reservation": {"reserved_cost": 1.0}},
+    )
+
+    assert response.usage.prompt_tokens == litellm_main.DEFAULT_MOCK_RESPONSE_PROMPT_TOKEN_COUNT
+
+
+_ADMISSION_INPUT_TOKENS: Final = 51234
+
+
+def _admission_metadata(input_tokens: int) -> dict[str, object]:  # mutable-ok: logging writes into metadata
+    return {"user_api_key_budget_reservation": {"reserved_cost": 1.0, "input_tokens": input_tokens}}
+
+
+_ADMISSION_METADATA: Final = _admission_metadata(_ADMISSION_INPUT_TOKENS)
+_MOCK_STREAM_MESSAGES: Final = [{"role": "user", "content": "hello " * 200}]
+_STREAM_CHUNK_BUILDER_TOKEN_COUNTER: Final = "litellm.litellm_core_utils.streaming_chunk_builder_utils.token_counter"
+
+
+def _prompt_token_counter_calls(token_counter: MagicMock) -> list[object]:
+    return [call for call in token_counter.call_args_list if call.kwargs.get("messages") is not None]
+
+
+def _client_usage_chunks(chunks: list[ModelResponseStream]) -> list[Usage]:
+    return [chunk.usage for chunk in chunks if getattr(chunk, "usage", None) is not None]
+
+
+@pytest.mark.parametrize("n", (None, 2))
+def test_mock_completion_stream_usage_reports_admission_input_tokens_without_tokenizer_fallback(n: int | None):
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        chunks: Final = list(
+            litellm.completion(
+                model="openai/gpt-5.4-mini",
+                messages=_MOCK_STREAM_MESSAGES,
+                mock_response="ok",
+                api_key="mock",
+                stream=True,
+                n=n,
+                stream_options={"include_usage": True},
+                metadata=_ADMISSION_METADATA,
+            )
+        )
+
+    usage_chunks: Final = _client_usage_chunks(chunks)
+    assert len(usage_chunks) == 1
+    assert usage_chunks[0].prompt_tokens == _ADMISSION_INPUT_TOKENS
+    assert usage_chunks[0].completion_tokens == litellm_main.DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT
+    assert usage_chunks[0].total_tokens == _ADMISSION_INPUT_TOKENS + usage_chunks[0].completion_tokens
+    assert _prompt_token_counter_calls(token_counter) == []
+    assert all(chunk.choices for chunk in chunks[:-1])
+    assert {chunk.id for chunk in chunks} == {chunks[0].id}
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("n", (None, 2))
+async def test_mock_acompletion_stream_usage_reports_admission_input_tokens_without_tokenizer_fallback(
+    n: int | None,
+):
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        response: Final = await litellm.acompletion(
+            model="openai/gpt-5.4-mini",
+            messages=_MOCK_STREAM_MESSAGES,
+            mock_response="ok",
+            api_key="mock",
+            stream=True,
+            n=n,
+            stream_options={"include_usage": True},
+            litellm_metadata=_ADMISSION_METADATA,
+        )
+        chunks: Final = [chunk async for chunk in response]
+
+    usage_chunks: Final = _client_usage_chunks(chunks)
+    assert len(usage_chunks) == 1
+    assert usage_chunks[0].prompt_tokens == _ADMISSION_INPUT_TOKENS
+    assert usage_chunks[0].total_tokens == _ADMISSION_INPUT_TOKENS + usage_chunks[0].completion_tokens
+    assert _prompt_token_counter_calls(token_counter) == []
+    assert all(chunk.choices for chunk in chunks[:-1])
+    assert {chunk.id for chunk in chunks} == {chunks[0].id}
+
+
+def test_mock_completion_stream_without_include_usage_hides_usage_chunk_but_logs_admission_count():
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        chunks: Final = list(
+            litellm.completion(
+                model="openai/gpt-5.4-mini",
+                messages=_MOCK_STREAM_MESSAGES,
+                mock_response="ok",
+                api_key="mock",
+                stream=True,
+                metadata=_ADMISSION_METADATA,
+            )
+        )
+
+    assert _client_usage_chunks(chunks) == []
+    assert all(len(chunk.choices) == 1 for chunk in chunks)
+    assert chunks[-1]._hidden_params["usage"].prompt_tokens == _ADMISSION_INPUT_TOKENS
+    assert _prompt_token_counter_calls(token_counter) == []
+
+
+def test_mock_completion_stream_with_empty_stream_options_completes_and_logs_admission_count():
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        chunks: Final = list(
+            litellm.completion(
+                model="openai/gpt-5.4-mini",
+                messages=_MOCK_STREAM_MESSAGES,
+                mock_response="ok",
+                api_key="mock",
+                stream=True,
+                stream_options={},
+                metadata=_ADMISSION_METADATA,
+            )
+        )
+
+    assert "".join(chunk.choices[0].delta.content or "" for chunk in chunks) == "ok"
+    assert _client_usage_chunks(chunks) == []
+    assert _prompt_token_counter_calls(token_counter) == []
+
+
+@pytest.mark.asyncio
+async def test_mock_acompletion_stream_with_empty_stream_options_completes_and_logs_admission_count():
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        response: Final = await litellm.acompletion(
+            model="openai/gpt-5.4-mini",
+            messages=_MOCK_STREAM_MESSAGES,
+            mock_response="ok",
+            api_key="mock",
+            stream=True,
+            stream_options={},
+            litellm_metadata=_ADMISSION_METADATA,
+        )
+        chunks: Final = [chunk async for chunk in response]
+
+    assert "".join(chunk.choices[0].delta.content or "" for chunk in chunks) == "ok"
+    assert _client_usage_chunks(chunks) == []
+    assert _prompt_token_counter_calls(token_counter) == []
+
+
+def test_mock_completion_stream_without_admission_count_falls_back_to_tokenizer():
+    expected_prompt_tokens: Final = litellm.token_counter(model="openai/gpt-5.4-mini", messages=_MOCK_STREAM_MESSAGES)
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        chunks: Final = list(
+            litellm.completion(
+                model="openai/gpt-5.4-mini",
+                messages=_MOCK_STREAM_MESSAGES,
+                mock_response="ok",
+                api_key="mock",
+                stream=True,
+                stream_options={"include_usage": True},
+                metadata={"user_api_key_budget_reservation": {"reserved_cost": 1.0}},
+            )
+        )
+
+    usage_chunks: Final = _client_usage_chunks(chunks)
+    assert len(usage_chunks) == 1
+    assert usage_chunks[0].prompt_tokens == expected_prompt_tokens
+    assert usage_chunks[0].total_tokens == expected_prompt_tokens + usage_chunks[0].completion_tokens
+    assert len(_prompt_token_counter_calls(token_counter)) >= 1
+
+
+@pytest.mark.asyncio
+async def test_mock_acompletion_stream_without_admission_count_falls_back_to_tokenizer():
+    expected_prompt_tokens: Final = litellm.token_counter(model="openai/gpt-5.4-mini", messages=_MOCK_STREAM_MESSAGES)
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        response: Final = await litellm.acompletion(
+            model="openai/gpt-5.4-mini",
+            messages=_MOCK_STREAM_MESSAGES,
+            mock_response="ok",
+            api_key="mock",
+            stream=True,
+            stream_options={"include_usage": True},
+        )
+        chunks: Final = [chunk async for chunk in response]
+
+    usage_chunks: Final = _client_usage_chunks(chunks)
+    assert len(usage_chunks) == 1
+    assert usage_chunks[0].prompt_tokens == expected_prompt_tokens
+    assert len(_prompt_token_counter_calls(token_counter)) >= 1
+
+
+def _usage_triple(usage: Usage) -> tuple[int, int, int]:
+    return (usage.prompt_tokens, usage.completion_tokens, usage.total_tokens)
+
+
+@pytest.mark.parametrize("input_tokens", (_ADMISSION_INPUT_TOKENS, 0))
+def test_mock_completion_stream_and_non_stream_report_the_same_admission_usage(input_tokens: int):
+    metadata: Final = _admission_metadata(input_tokens)
+    non_stream: Final = litellm.completion(
+        model="openai/gpt-5.4-mini",
+        messages=_MOCK_STREAM_MESSAGES,
+        mock_response="ok",
+        api_key="mock",
+        metadata=metadata,
+    )
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        chunks: Final = list(
+            litellm.completion(
+                model="openai/gpt-5.4-mini",
+                messages=_MOCK_STREAM_MESSAGES,
+                mock_response="ok",
+                api_key="mock",
+                stream=True,
+                stream_options={"include_usage": True},
+                metadata=metadata,
+            )
+        )
+
+    assert _usage_triple(non_stream.usage) == _usage_triple(_client_usage_chunks(chunks)[0])
+    assert non_stream.usage.prompt_tokens == input_tokens
+    assert _prompt_token_counter_calls(token_counter) == []
+
+
+@pytest.mark.asyncio
+async def test_mock_acompletion_stream_reports_zero_admission_input_tokens_without_tokenizer_fallback():
+    with patch(_STREAM_CHUNK_BUILDER_TOKEN_COUNTER, wraps=litellm.token_counter) as token_counter:
+        response: Final = await litellm.acompletion(
+            model="openai/gpt-5.4-mini",
+            messages=[{"role": "user", "content": ""}],
+            mock_response="ok",
+            api_key="mock",
+            stream=True,
+            stream_options={"include_usage": True},
+            litellm_metadata=_admission_metadata(0),
+        )
+        chunks: Final = [chunk async for chunk in response]
+
+    usage_chunks: Final = _client_usage_chunks(chunks)
+    assert len(usage_chunks) == 1
+    assert _usage_triple(usage_chunks[0]) == (0, usage_chunks[0].completion_tokens, usage_chunks[0].completion_tokens)
+    assert _prompt_token_counter_calls(token_counter) == []
+
+
+def test_mock_text_completion_stream_and_non_stream_report_the_same_zero_admission_usage():
+    metadata: Final = _admission_metadata(0)
+    non_stream: Final = litellm.text_completion(
+        model="openai/gpt-5.4-mini", prompt="", mock_response="ok", api_key="mock", metadata=metadata
+    )
+    chunks: Final = list(
+        litellm.text_completion(
+            model="openai/gpt-5.4-mini",
+            prompt="",
+            mock_response="ok",
+            api_key="mock",
+            stream=True,
+            stream_options={"include_usage": True},
+            metadata=metadata,
+        )
+    )
+
+    stream_usages: Final = tuple(chunk.usage for chunk in chunks if getattr(chunk, "usage", None) is not None)
+    assert len(stream_usages) == 1
+    assert _usage_triple(non_stream.usage) == _usage_triple(stream_usages[0])
+    assert non_stream.usage.prompt_tokens == 0
+
+
 def test_mock_completion_stream_with_model_response():
     """Test that mock_completion correctly handles stream=True with a ModelResponse as mock_response."""
     from litellm import completion
diff --git a/tests/test_litellm/test_redis.py b/tests/test_litellm/test_redis.py
index a96e8541e06..0e8c86d26df 100644
--- a/tests/test_litellm/test_redis.py
+++ b/tests/test_litellm/test_redis.py
@@ -10,13 +10,16 @@ from redis.credentials import CredentialProvider
 
 import litellm
 from litellm._redis import (
+    _AWS_IAM_KWARG_NAMES,
     _async_auth_kwargs,
+    _coerce_redis_kwargs_types,
     _get_redis_client_logic,
     _get_redis_cluster_kwargs,
     _get_redis_env_kwarg_mapping,
     _get_redis_kwargs,
     _get_redis_url_kwargs,
     _pretty_print_redis_config,
+    _uses_tls,
     get_redis_async_client,
     get_redis_client,
     get_redis_connection_pool,
@@ -24,12 +27,14 @@ from litellm._redis import (
 )
 from litellm._redis_credential_provider import (
     AzureADCredentialProvider,
+    ElastiCacheIAMCredentialProvider,
     GCPIAMCredentialProvider,
     _token_cache,
 )
 from litellm.caching.redis_cache import RedisCache
 from litellm.caching.redis_cluster_cache import RedisClusterCache
 from litellm.constants import REDIS_CLUSTER_HEALTH_CHECK_INTERVAL
+from litellm.proxy._types import CoordinationRedisParams
 
 
 class _StubCredentialProvider(CredentialProvider):
@@ -78,6 +83,8 @@ def clean_redis_environment(monkeypatch):
         "REDIS_URL",
         "REDIS_CLUSTER_NODES",
         "REDIS_SENTINEL_NODES",
+        "AWS_REGION",
+        "AWS_DEFAULT_REGION",
         *_get_redis_env_kwarg_mapping(),
     ):
         monkeypatch.delenv(var, raising=False)
@@ -110,6 +117,29 @@ def test_credential_provider_is_not_environment_derived():
     assert "credential_provider" not in mapping.values()
 
 
+_AWS_IAM_SETTINGS = {
+    "aws_iam_auth",
+    "aws_iam_user_name",
+    "aws_iam_cache_name",
+    "aws_iam_region",
+    "aws_iam_serverless",
+}
+
+
+def test_aws_iam_settings_are_environment_derived():
+    allowed = _get_redis_kwargs()
+    mapping = _get_redis_env_kwarg_mapping()
+
+    assert _AWS_IAM_SETTINGS <= allowed
+    assert set(_AWS_IAM_KWARG_NAMES) == _AWS_IAM_SETTINGS
+    assert {f for f in CoordinationRedisParams.model_fields if f.startswith("aws_iam_")} == _AWS_IAM_SETTINGS
+    assert mapping["REDIS_AWS_IAM_AUTH"] == "aws_iam_auth"
+    assert mapping["REDIS_AWS_IAM_USER_NAME"] == "aws_iam_user_name"
+    assert mapping["REDIS_AWS_IAM_CACHE_NAME"] == "aws_iam_cache_name"
+    assert mapping["REDIS_AWS_IAM_REGION"] == "aws_iam_region"
+    assert mapping["REDIS_AWS_IAM_SERVERLESS"] == "aws_iam_serverless"
+
+
 def test_sync_direct_preserves_credential_provider_identity(clean_redis_environment):
     provider = _StubCredentialProvider()
 
@@ -300,6 +330,333 @@ def test_gcp_kwargs_never_survive_client_logic(clean_redis_environment, override
     assert "gcp_ssl_ca_certs" not in redis_kwargs
 
 
+def test_aws_iam_environment_settings_install_provider(clean_redis_environment, monkeypatch):
+    monkeypatch.setenv("REDIS_AWS_IAM_AUTH", "true")
+    monkeypatch.setenv("REDIS_AWS_IAM_USER_NAME", "iam-user")
+    monkeypatch.setenv("REDIS_AWS_IAM_CACHE_NAME", "cache.example.com")
+    monkeypatch.setenv("REDIS_AWS_IAM_REGION", "us-east-1")
+    monkeypatch.setenv("REDIS_AWS_IAM_SERVERLESS", "1")
+    monkeypatch.setenv("REDIS_SSL", "1")
+
+    redis_kwargs = _get_redis_client_logic(host="cache.example.com", port=6379)
+
+    provider = redis_kwargs["credential_provider"]
+    assert isinstance(provider, ElastiCacheIAMCredentialProvider)
+    assert provider._is_serverless is True
+    assert not _AWS_IAM_SETTINGS & redis_kwargs.keys()
+
+
+@pytest.mark.parametrize(
+    "transport",
+    [
+        pytest.param({"host": "cache.example.com", "port": 6379}, id="host_without_ssl"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": False}, id="host_ssl_false"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "false"}, id="host_ssl_false_string"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "0"}, id="host_ssl_zero_string"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "no"}, id="host_ssl_no_string"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "off"}, id="host_ssl_off_string"),
+        pytest.param({"url": "redis://cache.example.com:6379", "ssl": True}, id="plaintext_url"),
+        pytest.param(
+            {"startup_nodes": [{"host": "cache.example.com", "port": 6379}]},
+            id="cluster_without_ssl",
+        ),
+        pytest.param(
+            {
+                "url": "rediss://cache.example.com:6379",
+                "startup_nodes": [{"host": "cache.example.com", "port": 6379}],
+            },
+            id="cluster_without_ssl_ignores_url_scheme",
+        ),
+        pytest.param(
+            {
+                "sentinel_nodes": [("sentinel.example.com", 26379)],
+                "service_name": "cache",
+            },
+            id="sentinel_without_ssl",
+        ),
+    ],
+)
+def test_aws_iam_auth_rejects_non_tls_connections(clean_redis_environment, transport):
+    with pytest.raises(ValueError, match="requires TLS"):
+        _get_redis_client_logic(
+            **transport,
+            aws_iam_auth=True,
+            aws_iam_user_name="iam-user",
+            aws_iam_cache_name="cache.example.com",
+            aws_iam_region="us-east-1",
+        )
+
+
+@pytest.mark.parametrize(
+    "transport",
+    [
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": True}, id="host"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "true"}, id="host_ssl_true_string"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "True"}, id="host_ssl_true_capitalized"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "1"}, id="host_ssl_one_string"),
+        pytest.param({"host": "cache.example.com", "port": 6379, "ssl": "yes"}, id="host_ssl_yes_string"),
+        pytest.param(
+            {"startup_nodes": [{"host": "cache.example.com", "port": 6379}], "ssl": "1"},
+            id="cluster_ssl_one_string",
+        ),
+        pytest.param({"url": "rediss://cache.example.com:6379"}, id="url"),
+        pytest.param(
+            {
+                "startup_nodes": [{"host": "cache.example.com", "port": 6379}],
+                "ssl": True,
+            },
+            id="cluster",
+        ),
+        pytest.param(
+            {
+                "sentinel_nodes": [("sentinel.example.com", 26379)],
+                "service_name": "cache",
+                "ssl": True,
+            },
+            id="sentinel",
+        ),
+    ],
+)
+def test_aws_iam_auth_accepts_tls_connections(clean_redis_environment, transport):
+    redis_kwargs = _get_redis_client_logic(
+        **transport,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+    )
+
+    assert isinstance(redis_kwargs["credential_provider"], ElastiCacheIAMCredentialProvider)
+
+
+@pytest.mark.parametrize("ssl", ["true", "True", "TRUE", "1", "yes", "YES", "false", "0", "no", "off", "", "maybe"])
+def test_tls_detection_agrees_with_the_ssl_kwarg_coercion(ssl):
+    assert _uses_tls({"ssl": ssl}) is _coerce_redis_kwargs_types({"ssl": ssl})["ssl"]
+
+
+def test_aws_iam_settings_are_removed_for_url_and_static_credentials(clean_redis_environment):
+    redis_kwargs = _get_redis_client_logic(
+        url="rediss://url-user:url-pass@cache.example.com:6380",
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+        username="static-user",
+        password="static-password",
+    )
+
+    assert isinstance(redis_kwargs["credential_provider"], ElastiCacheIAMCredentialProvider)
+    assert redis_kwargs["url"] == "rediss://cache.example.com:6380"
+    assert "username" not in redis_kwargs
+    assert "password" not in redis_kwargs
+    assert not _AWS_IAM_SETTINGS & redis_kwargs.keys()
+
+
+@pytest.mark.parametrize("missing", ["aws_iam_user_name", "aws_iam_cache_name", "aws_iam_region"])
+def test_aws_iam_missing_setting_fails_closed(clean_redis_environment, missing):
+    settings = {
+        "aws_iam_auth": True,
+        "aws_iam_user_name": "iam-user",
+        "aws_iam_cache_name": "cache.example.com",
+        "aws_iam_region": "us-east-1",
+        "ssl": True,
+    }
+    settings[missing] = None
+
+    with pytest.raises(ValueError, match=missing):
+        _get_redis_client_logic(host="cache.example.com", port=6379, **settings)
+
+
+@pytest.mark.parametrize("region_var", ["AWS_REGION", "AWS_DEFAULT_REGION"])
+def test_aws_iam_region_falls_back_to_environment(clean_redis_environment, monkeypatch, region_var):
+    monkeypatch.setenv(region_var, "sa-east-1")
+
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        ssl=True,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+    )
+
+    provider = redis_kwargs["credential_provider"]
+    assert isinstance(provider, ElastiCacheIAMCredentialProvider)
+    assert provider._region == "sa-east-1"
+
+
+def test_aws_iam_region_prefers_aws_region_over_default_region(clean_redis_environment, monkeypatch):
+    monkeypatch.setenv("AWS_REGION", "sa-east-1")
+    monkeypatch.setenv("AWS_DEFAULT_REGION", "eu-west-1")
+
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        ssl=True,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+    )
+
+    assert redis_kwargs["credential_provider"]._region == "sa-east-1"
+
+
+def test_aws_iam_region_prefers_explicit_over_environment(clean_redis_environment, monkeypatch):
+    monkeypatch.setenv("AWS_REGION", "sa-east-1")
+
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        ssl=True,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="explicit-region",
+    )
+
+    assert redis_kwargs["credential_provider"]._region == "explicit-region"
+
+
+def test_aws_iam_settings_map_to_distinct_provider_fields(clean_redis_environment):
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        ssl=True,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user-value",
+        aws_iam_cache_name="iam-cache-value",
+        aws_iam_region="iam-region-value",
+    )
+
+    provider = redis_kwargs["credential_provider"]
+    assert isinstance(provider, ElastiCacheIAMCredentialProvider)
+    assert provider._user_name == "iam-user-value"
+    assert provider._cache_name == "iam-cache-value"
+    assert provider._region == "iam-region-value"
+
+
+@pytest.mark.parametrize("aws_iam_auth", [None, False, "", "false", "0", "no", "off"])
+def test_aws_iam_auth_disabled_does_not_install_provider(clean_redis_environment, aws_iam_auth):
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        aws_iam_auth=aws_iam_auth,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+    )
+
+    assert "credential_provider" not in redis_kwargs
+    assert not _AWS_IAM_SETTINGS & redis_kwargs.keys()
+
+
+@pytest.mark.parametrize("aws_iam_auth", [True, "true", "True", "TRUE", "1", "yes"])
+def test_aws_iam_auth_enabled_by_any_truthy_flag(clean_redis_environment, aws_iam_auth):
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        ssl=True,
+        aws_iam_auth=aws_iam_auth,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache-name",
+        aws_iam_region="us-east-1",
+    )
+
+    assert isinstance(redis_kwargs["credential_provider"], ElastiCacheIAMCredentialProvider)
+
+
+@pytest.mark.parametrize(
+    "aws_iam_serverless, expected",
+    [
+        pytest.param(None, False, id="unset"),
+        pytest.param(False, False, id="bool_false"),
+        pytest.param("false", False, id="string_false"),
+        pytest.param("0", False, id="string_zero"),
+        pytest.param(True, True, id="bool_true"),
+        pytest.param("true", True, id="string_true"),
+        pytest.param("1", True, id="string_one"),
+    ],
+)
+def test_aws_iam_serverless_flag_reaches_the_provider(clean_redis_environment, aws_iam_serverless, expected):
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        ssl=True,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache-name",
+        aws_iam_region="us-east-1",
+        aws_iam_serverless=aws_iam_serverless,
+    )
+
+    provider = redis_kwargs["credential_provider"]
+    assert isinstance(provider, ElastiCacheIAMCredentialProvider)
+    assert provider._is_serverless is expected
+    assert "aws_iam_serverless" not in redis_kwargs
+
+
+def test_explicit_provider_wins_over_aws_iam(clean_redis_environment):
+    provider = _StubCredentialProvider()
+
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        credential_provider=provider,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+    )
+
+    assert redis_kwargs["credential_provider"] is provider
+    assert "aws_iam_auth" not in redis_kwargs
+
+
+def test_gcp_wins_over_aws_iam(clean_redis_environment):
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        gcp_service_account="sa@example.com",
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+    )
+
+    assert "credential_provider" not in redis_kwargs
+    assert redis_kwargs["redis_connect_func"]._gcp_service_account == "sa@example.com"
+
+
+def test_azure_wins_over_aws_iam(clean_redis_environment):
+    redis_kwargs = _get_redis_client_logic(
+        host="cache.example.com",
+        port=6379,
+        azure_redis_ad_token="true",
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+    )
+
+    assert "credential_provider" not in redis_kwargs
+    assert redis_kwargs["redis_connect_func"]._azure_redis_ad_token is True
+
+
+def test_async_cluster_installs_aws_iam_provider(clean_redis_environment):
+    startup_nodes = [{"host": "cluster-node", "port": 6379}]
+
+    client = get_redis_async_client(
+        startup_nodes=startup_nodes,
+        ssl=True,
+        aws_iam_auth=True,
+        aws_iam_user_name="iam-user",
+        aws_iam_cache_name="cache.example.com",
+        aws_iam_region="us-east-1",
+    )
+
+    assert isinstance(client.connection_kwargs["credential_provider"], ElastiCacheIAMCredentialProvider)
+
+
 def test_provider_keeps_the_rest_of_the_url_intact(clean_redis_environment):
     provider = _StubCredentialProvider()
 
diff --git a/tests/test_litellm/test_redis_credential_provider.py b/tests/test_litellm/test_redis_credential_provider.py
new file mode 100644
index 00000000000..96b1933b0e3
--- /dev/null
+++ b/tests/test_litellm/test_redis_credential_provider.py
@@ -0,0 +1,236 @@
+import asyncio
+import builtins
+import sys
+from types import SimpleNamespace
+from urllib.parse import parse_qs, urlsplit
+
+import pytest
+
+from litellm._redis_credential_provider import ElastiCacheIAMCredentialProvider
+
+
+class _FakeCredentials:
+    def __init__(self, access_key: str) -> None:
+        self.access_key = access_key
+        self.secret_key = "synthetic-secret"
+        self.token = "synthetic-session-token"
+
+    def get_frozen_credentials(self):
+        return self
+
+
+class _RotatingFakeCredentials:
+    def __init__(self) -> None:
+        self.calls = 0
+
+    def __bool__(self) -> bool:
+        return False
+
+    def get_frozen_credentials(self):
+        self.calls += 1
+        return SimpleNamespace(
+            access_key=f"AKIA-SYNTHETIC-{self.calls}",
+            secret_key="synthetic-secret",
+            token="synthetic-session-token",
+        )
+
+
+class _FakeResolver:
+    def __init__(self, credentials: _FakeCredentials | _RotatingFakeCredentials | None) -> None:
+        self.credentials = credentials
+        self.calls = 0
+
+    def __call__(self):
+        self.calls += 1
+        return self.credentials
+
+
+def test_elasticache_provider_signs_expected_query():
+    resolver = _FakeResolver(_FakeCredentials("AKIA-SYNTHETIC"))
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+        credentials_resolver=resolver,
+    )
+
+    user_name, token = provider.get_credentials()
+    parsed = urlsplit("https://" + token)
+    query = parse_qs(parsed.query)
+
+    assert user_name == "iam-user"
+    assert parsed.netloc == "cache.example.com"
+    assert query["Action"] == ["connect"]
+    assert query["User"] == ["iam-user"]
+    assert query["X-Amz-Expires"] == ["900"]
+    assert "elasticache" in query["X-Amz-Credential"][0]
+    assert query["X-Amz-Credential"][0].split("/")[2] == "us-east-1"
+    assert not token.startswith("https://")
+
+
+def test_elasticache_provider_resolves_credentials_once_but_refreshes_signature():
+    rotating_credentials = _RotatingFakeCredentials()
+    resolver = _FakeResolver(rotating_credentials)
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+        credentials_resolver=resolver,
+    )
+
+    first = provider.get_credentials()
+    second = provider.get_credentials()
+    async_result = asyncio.run(provider.get_credentials_async())
+
+    assert first[0] == second[0] == async_result[0] == "iam-user"
+    assert first[1] != second[1]
+    assert async_result[1] != second[1]
+    assert resolver.calls == 1
+    assert rotating_credentials.calls == 3
+
+
+def test_elasticache_provider_uses_botocore_session_credentials(monkeypatch):
+    credentials = _FakeCredentials("AKIA-SYNTHETIC")
+    monkeypatch.setattr("botocore.session.get_session", lambda: SimpleNamespace(get_credentials=lambda: credentials))
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+    )
+
+    user_name, token = provider.get_credentials()
+
+    assert user_name == "iam-user"
+    assert "AKIA-SYNTHETIC" in token
+
+
+def test_elasticache_provider_reports_missing_botocore(monkeypatch):
+    original_import = builtins.__import__
+
+    def import_without_botocore(name, *args, **kwargs):
+        if name == "botocore.session":
+            raise ImportError("synthetic missing dependency")
+        return original_import(name, *args, **kwargs)
+
+    monkeypatch.delitem(sys.modules, "botocore.session", raising=False)
+    monkeypatch.setattr(builtins, "__import__", import_without_botocore)
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+    )
+
+    with pytest.raises(ImportError, match="pip install boto3"):
+        provider.get_credentials()
+
+
+def test_elasticache_provider_reports_missing_credentials():
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+        credentials_resolver=_FakeResolver(None),
+    )
+
+    with pytest.raises(RuntimeError, match="Unable to resolve AWS credentials"):
+        provider.get_credentials()
+
+
+def test_elasticache_provider_reports_missing_signing_dependency(monkeypatch):
+    original_import = builtins.__import__
+
+    def import_without_botocore_auth(name, *args, **kwargs):
+        if name == "botocore.auth":
+            raise ImportError("synthetic missing dependency")
+        return original_import(name, *args, **kwargs)
+
+    monkeypatch.delitem(sys.modules, "botocore.auth", raising=False)
+    monkeypatch.setattr(builtins, "__import__", import_without_botocore_auth)
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+        credentials_resolver=_FakeResolver(_FakeCredentials("AKIA-SYNTHETIC")),
+    )
+
+    with pytest.raises(ImportError, match="pip install boto3"):
+        provider.get_credentials()
+
+
+def test_elasticache_provider_recovers_after_a_failed_resolution():
+    resolver = _FakeResolver(None)
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache.example.com",
+        region="us-east-1",
+        credentials_resolver=resolver,
+    )
+
+    with pytest.raises(RuntimeError, match="Unable to resolve AWS credentials"):
+        provider.get_credentials()
+
+    resolver.credentials = _FakeCredentials("AKIA-SYNTHETIC")
+    user_name, token = provider.get_credentials()
+
+    assert user_name == "iam-user"
+    assert token
+    assert resolver.calls == 2
+
+
+@pytest.mark.parametrize(
+    "provider_kwargs, expected_operation_params",
+    [
+        pytest.param({}, frozenset({"Action", "User"}), id="default_is_self_designed"),
+        pytest.param({"is_serverless": False}, frozenset({"Action", "User"}), id="self_designed"),
+        pytest.param({"is_serverless": True}, frozenset({"Action", "User", "ResourceType"}), id="serverless"),
+    ],
+)
+def test_elasticache_provider_signs_resource_type_only_for_serverless(provider_kwargs, expected_operation_params):
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="cache-name",
+        region="us-east-1",
+        credentials_resolver=_FakeResolver(_FakeCredentials("AKIA-SYNTHETIC")),
+        **provider_kwargs,
+    )
+
+    _, token = provider.get_credentials()
+    query_string = urlsplit("https://" + token).query
+    param_names = tuple(pair.split("=", 1)[0] for pair in query_string.split("&"))
+    first_auth_param = next(i for i, name in enumerate(param_names) if name.startswith("X-Amz-"))
+    query = parse_qs(query_string)
+
+    assert frozenset(param_names[:first_auth_param]) == expected_operation_params
+    assert all(name.startswith("X-Amz-") for name in param_names[first_auth_param:])
+    assert query.get("ResourceType") == (["ServerlessCache"] if "ResourceType" in expected_operation_params else None)
+    assert query["X-Amz-Signature"]
+
+
+def test_elasticache_provider_lowercases_the_cache_name():
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name="iam-user",
+        cache_name="Mixed-Case-Cache",
+        region="us-east-1",
+        credentials_resolver=_FakeResolver(_FakeCredentials("AKIA-SYNTHETIC")),
+    )
+
+    _, token = provider.get_credentials()
+
+    assert urlsplit("https://" + token).netloc == "mixed-case-cache"
+
+
+def test_elasticache_provider_encodes_reserved_characters_in_the_user_name():
+    user_name = "iam user/with+reserved&chars"
+    provider = ElastiCacheIAMCredentialProvider(
+        user_name=user_name,
+        cache_name="cache-name",
+        region="us-east-1",
+        credentials_resolver=_FakeResolver(_FakeCredentials("AKIA-SYNTHETIC")),
+    )
+
+    returned_user_name, token = provider.get_credentials()
+    query = parse_qs(urlsplit("https://" + token).query)
+
+    assert returned_user_name == user_name
+    assert query["User"] == [user_name]
+    assert query["Action"] == ["connect"]
diff --git a/tests/test_litellm/test_router.py b/tests/test_litellm/test_router.py
index bc79c5f6589..def67ccf88b 100644
--- a/tests/test_litellm/test_router.py
+++ b/tests/test_litellm/test_router.py
@@ -19,6 +19,8 @@ import respx
 
 
 import litellm
+from litellm.caching.caching import DualCache
+from litellm.caching.redis_cache import _redis_circuit_breaker_guard
 from litellm import Router
 from litellm.exceptions import MidStreamFallbackError
 from litellm.integrations.custom_guardrail import CustomGuardrail
@@ -42,7 +44,7 @@ from litellm.router import (
     _is_retriable_anthropic_status,
 )
 from litellm.router_strategy import simple_shuffle
-from litellm.types.router import DeploymentTypedDict, RetryPolicy
+from litellm.types.router import Deployment, DeploymentTypedDict, LiteLLM_Params, ModelInfo, RetryPolicy
 
 
 def test_update_kwargs_does_not_mutate_defaults_and_merges_metadata():
@@ -5049,6 +5051,41 @@ def test_get_deployment_model_info_base_model_merge_priority():
     print("✓ Base model merge priority test passed!")
 
 
+@pytest.mark.parametrize(
+    "model, litellm_params, endpoint, expected",
+    [
+        (
+            "gpt",
+            {"model": "azure_ai/gpt-5.4-mini", "api_base": "https://my-resource.services.ai.azure.com", "api_key": "key"},
+            "gpt/openai/deployments/gpt-5.4-mini/chat/completions",
+            "gpt-5.4-mini/openai/deployments/gpt-5.4-mini/chat/completions",
+        ),
+        (
+            "aws/anthropic/bedrock-claude",
+            {"model": "bedrock/us.anthropic.claude-haiku-4-5-20251001-v1:0"},
+            "/model/aws/anthropic/bedrock-claude/invoke",
+            "/model/us.anthropic.claude-haiku-4-5-20251001-v1:0/invoke",
+        ),
+        (
+            "my-gemini",
+            {"model": "gemini/gemini-3.1-pro-preview", "api_key": "key"},
+            "v1beta/models/my-gemini:streamGenerateContent",
+            "v1beta/models/gemini-3.1-pro-preview:streamGenerateContent",
+        ),
+    ],
+)
+def test_add_deployment_model_to_endpoint_rewrites_the_model_group_only_as_whole_path_segments(
+    model, litellm_params, endpoint, expected
+):
+    router = litellm.Router(model_list=[{"model_name": model, "litellm_params": litellm_params}])
+
+    result = router._add_deployment_model_to_endpoint_for_llm_passthrough_route(
+        kwargs={"endpoint": endpoint}, model=model, model_name=litellm_params["model"]
+    )
+
+    assert result["endpoint"] == expected
+
+
 def test_add_deployment_model_to_endpoint_for_llm_passthrough_route():
     """
     Test that _add_deployment_model_to_endpoint_for_llm_passthrough_route correctly strips bedrock provider prefix
@@ -8173,6 +8210,204 @@ def test_get_configured_token_limits_coerces_numeric_strings():
     assert router.get_configured_token_limits("quoted-limits-model") == (32000, 8000)
 
 
+def test_get_model_listing_info_prefers_base_model_over_litellm_params_model():
+    """The cost-map key comes from base_model when set, so a deployment pointing at an
+    opaque backend name still resolves the real catalog entry."""
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "bedrock-claude-opus-5",
+                "litellm_params": {"model": "bedrock/eu.anthropic.claude-opus-5"},
+                "model_info": {"base_model": "eu.anthropic.claude-opus-5"},
+            }
+        ]
+    )
+
+    info = router.get_model_listing_info("bedrock-claude-opus-5")
+    assert info is not None
+    assert info.cost_map_keys == ("eu.anthropic.claude-opus-5",)
+
+
+def test_get_model_listing_info_falls_back_to_litellm_params_model():
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "bedrock-claude-opus-5",
+                "litellm_params": {"model": "bedrock/eu.anthropic.claude-opus-5"},
+            }
+        ]
+    )
+
+    info = router.get_model_listing_info("bedrock-claude-opus-5")
+    assert info is not None
+    assert info.cost_map_keys == ("bedrock/eu.anthropic.claude-opus-5",)
+
+
+def test_get_model_listing_info_ignores_blank_base_model():
+    """A base_model set to an empty string is absent, not a cost-map key."""
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "bedrock-claude-opus-5",
+                "litellm_params": {"model": "bedrock/eu.anthropic.claude-opus-5"},
+                "model_info": {"base_model": ""},
+            }
+        ]
+    )
+
+    info = router.get_model_listing_info("bedrock-claude-opus-5")
+    assert info is not None
+    assert info.cost_map_keys == ("bedrock/eu.anthropic.claude-opus-5",)
+
+
+def test_get_model_listing_info_returns_none_for_unknown_name():
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "no-limits-model",
+                "litellm_params": {"model": "openai/some-unmapped-model"},
+            }
+        ]
+    )
+
+    assert router.get_model_listing_info("not-a-real-model") is None
+
+
+def test_get_model_listing_info_carries_configured_limits():
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "my-custom-model",
+                "litellm_params": {"model": "openai/some-unmapped-model"},
+                "model_info": {"max_input_tokens": 32000, "max_output_tokens": 8000},
+            }
+        ]
+    )
+
+    info = router.get_model_listing_info("my-custom-model")
+    assert info is not None
+    assert (info.max_input_tokens, info.max_output_tokens) == (32000, 8000)
+
+
+def test_widest_configured_limit_ignores_absent_and_malformed_values():
+    model_infos = (
+        {"max_input_tokens": 32000},
+        {},
+        {"max_input_tokens": "not-a-number"},
+        {"max_input_tokens": "128000"},
+        {"max_output_tokens": 4096},
+    )
+
+    assert litellm.Router._widest_configured_limit(model_infos, "max_input_tokens") == 128000
+    assert litellm.Router._widest_configured_limit(model_infos, "max_output_tokens") == 4096
+    assert litellm.Router._widest_configured_limit((), "max_input_tokens") is None
+
+
+def test_get_model_listing_info_dedupes_interchangeable_deployments():
+    """The ordinary group is N deployments of one model, so it yields exactly one key."""
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "gpt-4o",
+                "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-a"},
+            },
+            {
+                "model_name": "gpt-4o",
+                "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-b"},
+            },
+        ]
+    )
+
+    info = router.get_model_listing_info("gpt-4o")
+    assert info is not None
+    assert info.cost_map_keys == ("openai/gpt-4o",)
+
+
+def test_get_model_listing_info_collects_every_model_in_a_mixed_group():
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "house-claude",
+                "litellm_params": {"model": "anthropic/claude-3-haiku-20240307"},
+            },
+            {
+                "model_name": "house-claude",
+                "litellm_params": {"model": "bedrock/eu.anthropic.claude-opus-5"},
+            },
+        ]
+    )
+
+    info = router.get_model_listing_info("house-claude")
+    assert info is not None
+    assert info.cost_map_keys == (
+        "anthropic/claude-3-haiku-20240307",
+        "bedrock/eu.anthropic.claude-opus-5",
+    )
+
+
+def test_get_model_listing_info_reports_widest_configured_limits_in_a_mixed_group():
+    """Matches how get_model_group_info aggregates for the Admin UI, so the two agree."""
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "house-model",
+                "litellm_params": {"model": "openai/some-unmapped-model"},
+                "model_info": {"max_input_tokens": 32000, "max_output_tokens": 4096},
+            },
+            {
+                "model_name": "house-model",
+                "litellm_params": {"model": "openai/another-unmapped-model"},
+                "model_info": {"max_input_tokens": 128000, "max_output_tokens": 16384},
+            },
+        ]
+    )
+
+    info = router.get_model_listing_info("house-model")
+    assert info is not None
+    assert (info.max_input_tokens, info.max_output_tokens) == (128000, 16384)
+
+
+def test_get_model_listing_info_reads_base_model_from_litellm_params():
+    """base_model resolution mirrors get_router_model_info, which also accepts it there."""
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "azure-deployment",
+                "litellm_params": {
+                    "model": "azure/my-azure-deployment-name",
+                    "base_model": "azure/gpt-4o",
+                    "api_key": "sk-a",
+                    "api_base": "https://example.openai.azure.com",
+                },
+            }
+        ]
+    )
+
+    info = router.get_model_listing_info("azure-deployment")
+    assert info is not None
+    assert info.cost_map_keys == ("azure/gpt-4o",)
+
+
+def test_get_model_listing_info_skips_wildcard_pattern_matching():
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "bedrock/*",
+                "litellm_params": {"model": "bedrock/*"},
+                "model_info": {"max_input_tokens": 12345},
+            }
+        ]
+    )
+
+    with patch.object(
+        router.pattern_router, "route", side_effect=AssertionError("pattern route called")
+    ):
+        assert (
+            router.get_model_listing_info("bedrock/anthropic.claude-3-5-sonnet-20240620-v1:0")
+            is None
+        )
+
+
 def test_get_configured_mode_reads_deployment_model_info():
     router = litellm.Router(
         model_list=[
@@ -10003,13 +10238,6 @@ class TestTaggedAutoRouterOnSharedModelName:
     def test_deployment_without_litellm_params_mapping_is_not_a_marker(self):
         assert litellm.Router._is_strategy_marker_deployment({"model_name": "gpt4o"}) is False
 
-    def test_model_name_has_plain_deployments_reflects_the_pool(self):
-        mixed = self._router(marker_tags=["route"], include_plain_sibling=True, enable_tag_filtering=True)
-        marker_only = self._router(marker_tags=["route"], include_plain_sibling=False, enable_tag_filtering=True)
-
-        assert mixed._model_name_has_plain_deployments("gpt4o") is True
-        assert marker_only._model_name_has_plain_deployments("gpt4o") is False
-
 
 class TestAutoRouterSharedModelNameConnectionParams:
     """A plain deployment sharing its model_name with an `auto_router/` marker must not have
@@ -10618,6 +10846,300 @@ class TestModelGroupAliasReachesPreRoutingStrategies:
             )
 
 
+class TestTeamPublicNameReachesPreRoutingStrategies:
+    """A team-scoped strategy router is stored under an internal `model_name_{team}_{uuid}` with the
+    caller-facing name in `model_info.team_public_model_name`, and the four registries key on that
+    internal name. A team key asks for the public name, so the hook has to resolve it to the team's
+    marker through the same team-first resolution the deployment path uses, and a resolution that
+    yields only markers is not callable on any path (LIT-7363)."""
+
+    MARKER_TIMEOUT = 42.0
+    REGISTRY_NAMES = ("auto_routers", "complexity_routers", "adaptive_routers", "quality_routers")
+    TEAM = "team-a"
+    OTHER_TEAM = "team-b"
+    PUBLIC_NAME = "smart-route"
+    INTERNAL_NAME = "model_name_team-a_0b3c"
+    SIBLING_INTERNAL_NAME = "model_name_team-a_9e1d"
+
+    class _RewriteStrategy:
+        def __init__(self, rewrite_to: str = "gemini-flash"):
+            self.rewrite_to = rewrite_to
+
+        async def async_pre_routing_hook(
+            self, model, request_kwargs, messages=None, input=None, specific_deployment=False
+        ):
+            from litellm.types.router import PreRoutingHookResponse
+
+            return PreRoutingHookResponse(model=self.rewrite_to, messages=messages)
+
+    @classmethod
+    def _team_marker(cls, internal_name: str, tags: list[str] | None = None) -> dict:
+        tiers = dict.fromkeys(("SIMPLE", "MEDIUM", "COMPLEX", "REASONING"), "gemini-flash")
+        return {
+            "model_name": internal_name,
+            "litellm_params": {
+                "model": "auto_router/complexity_router",
+                "complexity_router_config": {"tiers": tiers},
+                "complexity_router_default_model": "gemini-flash",
+                "timeout": cls.MARKER_TIMEOUT,
+                **({"tags": tags} if tags else {}),
+            },
+            "model_info": {"team_id": cls.TEAM, "team_public_model_name": cls.PUBLIC_NAME},
+        }
+
+    @classmethod
+    def _router(
+        cls,
+        registrations: dict[str, "TestTeamPublicNameReachesPreRoutingStrategies._RewriteStrategy"],
+        registry_name: str = "complexity_routers",
+        extra_deployments: tuple[dict, ...] = (),
+        markers: tuple[dict, ...] | None = None,
+        enable_tag_filtering: bool = False,
+    ) -> "litellm.Router":
+        from litellm.types.router import TaggedPreRoutingStrategy
+
+        markers = markers if markers is not None else (cls._team_marker(cls.INTERNAL_NAME),)
+        tier = {
+            "model_name": "gemini-flash",
+            "litellm_params": {"model": "gemini/gemini-3.6-flash", "mock_response": "routed by the tier"},
+        }
+        router = litellm.Router(
+            model_list=[*markers, tier, *extra_deployments],
+            enable_tag_filtering=enable_tag_filtering,
+        )
+        tags_by_name = {m["model_name"]: tuple(m["litellm_params"].get("tags") or ()) for m in markers}
+        for name in cls.REGISTRY_NAMES:
+            setattr(router, name, {})
+        setattr(
+            router,
+            registry_name,
+            {
+                name: [TaggedPreRoutingStrategy(tags=tags_by_name[name], strategy=strategy)]
+                for name, strategy in registrations.items()
+            },
+        )
+        return router
+
+    @staticmethod
+    def _messages() -> list[dict[str, str]]:
+        return [{"role": "user", "content": "What is the capital of France?"}]
+
+    @classmethod
+    def _team_request(cls, team_id: str | None = "team-a", tags: list[str] | None = None) -> dict:
+        metadata = {**({"user_api_key_team_id": team_id} if team_id else {}), **({"tags": tags} if tags else {})}
+        return {"metadata": metadata}
+
+    @pytest.mark.parametrize("registry_name", REGISTRY_NAMES)
+    @pytest.mark.asyncio
+    async def test_team_key_dispatches_to_the_strategy_registered_under_the_internal_name(self, registry_name):
+        router = self._router({self.INTERNAL_NAME: self._RewriteStrategy()}, registry_name=registry_name)
+
+        response = await router.async_pre_routing_hook(
+            model=self.PUBLIC_NAME, request_kwargs=self._team_request(), messages=self._messages()
+        )
+
+        assert response is not None
+        assert response.model == "gemini-flash"
+
+    @pytest.mark.asyncio
+    async def test_team_key_deployment_selection_lands_on_the_tier_and_forwards_the_marker_params(self):
+        router = self._router({self.INTERNAL_NAME: self._RewriteStrategy()})
+        request_kwargs = self._team_request()
+
+        deployment = await router.async_get_available_deployment(
+            model=self.PUBLIC_NAME, request_kwargs=request_kwargs, messages=self._messages()
+        )
+
+        assert deployment["litellm_params"]["model"] == "gemini/gemini-3.6-flash"
+        assert request_kwargs["timeout"] == self.MARKER_TIMEOUT
+
+    @pytest.mark.asyncio
+    async def test_another_team_never_reaches_the_strategy_or_the_marker(self):
+        router = self._router({self.INTERNAL_NAME: self._RewriteStrategy()})
+
+        assert (
+            await router.async_pre_routing_hook(
+                model=self.PUBLIC_NAME, request_kwargs=self._team_request(self.OTHER_TEAM), messages=self._messages()
+            )
+            is None
+        )
+        with pytest.raises(litellm.BadRequestError):
+            await router.async_get_available_deployment(
+                model=self.PUBLIC_NAME, request_kwargs=self._team_request(self.OTHER_TEAM), messages=self._messages()
+            )
+
+    @pytest.mark.asyncio
+    async def test_sibling_team_markers_select_by_request_tag_then_default(self):
+        router = self._router(
+            {
+                self.INTERNAL_NAME: self._RewriteStrategy("cn-model"),
+                self.SIBLING_INTERNAL_NAME: self._RewriteStrategy("us-model"),
+            },
+            markers=(
+                self._team_marker(self.INTERNAL_NAME, tags=["cn"]),
+                self._team_marker(self.SIBLING_INTERNAL_NAME, tags=["us", "default"]),
+            ),
+        )
+
+        async def routed(tags: list[str] | None) -> str | None:
+            response = await router.async_pre_routing_hook(
+                model=self.PUBLIC_NAME, request_kwargs=self._team_request(tags=tags), messages=self._messages()
+            )
+            return response.model if response else None
+
+        assert await routed(["cn"]) == "cn-model"
+        assert await routed(["us"]) == "us-model"
+        assert await routed(None) == "us-model"
+
+    @pytest.mark.asyncio
+    async def test_team_public_name_shadows_a_global_model_for_that_team_only(self):
+        router = self._router(
+            {self.INTERNAL_NAME: self._RewriteStrategy()},
+            extra_deployments=({"model_name": self.PUBLIC_NAME, "litellm_params": {"model": "openai/gpt-4o"}},),
+        )
+
+        async def routed(request_kwargs: dict) -> str | None:
+            response = await router.async_pre_routing_hook(
+                model=self.PUBLIC_NAME, request_kwargs=request_kwargs, messages=self._messages()
+            )
+            return response.model if response else None
+
+        async def selected(request_kwargs: dict) -> str:
+            deployment = await router.async_get_available_deployment(
+                model=self.PUBLIC_NAME, request_kwargs=request_kwargs, messages=self._messages()
+            )
+            return deployment["litellm_params"]["model"]
+
+        assert await routed(self._team_request()) == "gemini-flash"
+        assert await selected(self._team_request()) == "gemini/gemini-3.6-flash"
+        for request_kwargs in (self._team_request(None), self._team_request(self.OTHER_TEAM)):
+            assert await routed(request_kwargs) is None
+            assert await selected(request_kwargs) == "openai/gpt-4o"
+
+    @pytest.mark.asyncio
+    async def test_tag_filtering_hands_untagged_team_requests_to_the_team_plain_sibling(self):
+        plain_sibling = {
+            "model_name": self.SIBLING_INTERNAL_NAME,
+            "litellm_params": {"model": "openai/gpt-4o"},
+            "model_info": {"team_id": self.TEAM, "team_public_model_name": self.PUBLIC_NAME},
+        }
+        router = self._router(
+            {self.INTERNAL_NAME: self._RewriteStrategy()},
+            markers=(self._team_marker(self.INTERNAL_NAME, tags=["route"]),),
+            extra_deployments=(plain_sibling,),
+            enable_tag_filtering=True,
+        )
+
+        tagged = await router.async_pre_routing_hook(
+            model=self.PUBLIC_NAME, request_kwargs=self._team_request(tags=["route"]), messages=self._messages()
+        )
+        assert tagged is not None and tagged.model == "gemini-flash"
+        for _ in range(20):
+            deployment = await router.async_get_available_deployment(
+                model=self.PUBLIC_NAME, request_kwargs=self._team_request(), messages=self._messages()
+            )
+            assert deployment["litellm_params"]["model"] == "openai/gpt-4o"
+
+    @pytest.mark.asyncio
+    async def test_marker_only_team_resolution_is_rejected_as_uncallable(self):
+        import re
+
+        from litellm.types.router import RouterErrors
+
+        router = self._router({})
+
+        with pytest.raises(
+            litellm.BadRequestError, match=re.escape(RouterErrors.only_strategy_marker_deployments.value)
+        ):
+            await router.async_get_available_deployment(
+                model=self.PUBLIC_NAME, request_kwargs=self._team_request(), messages=self._messages()
+            )
+
+    @pytest.mark.asyncio
+    async def test_proxy_admin_without_a_team_reaches_the_team_strategy_by_public_name(self):
+        router = self._router({self.INTERNAL_NAME: self._RewriteStrategy()})
+        request_kwargs = {"metadata": {"user_api_key_auth": SimpleNamespace(user_role="proxy_admin")}}
+
+        response = await router.async_pre_routing_hook(
+            model=self.PUBLIC_NAME, request_kwargs=request_kwargs, messages=self._messages()
+        )
+
+        assert response is not None
+        assert response.model == "gemini-flash"
+    @pytest.mark.asyncio
+    async def test_strategy_resolution_agrees_with_the_deployment_path_for_every_principal(self):
+        router = self._router(
+            {self.INTERNAL_NAME: self._RewriteStrategy()},
+            extra_deployments=({"model_name": "shared-name", "litellm_params": {"model": "openai/gpt-4o"}},),
+        )
+        principals = {
+            "team": self._team_request(),
+            "other-team": self._team_request(self.OTHER_TEAM),
+            "no-team": self._team_request(None),
+            "admin": {"metadata": {"user_api_key_auth": SimpleNamespace(user_role="proxy_admin")}},
+        }
+        for principal, request_kwargs in principals.items():
+            for model in (self.PUBLIC_NAME, "shared-name", "gemini-flash", "missing"):
+                resolved = [d["model_name"] for d in router.deployments_for_request(model, request_kwargs)]
+                callable_names = [
+                    name
+                    for name, deployment in zip(resolved, router.deployments_for_request(model, request_kwargs))
+                    if not router._is_strategy_marker_deployment(deployment)
+                ]
+                if resolved and not callable_names:
+                    with pytest.raises(litellm.BadRequestError, match="strategy router marker"):
+                        router._common_checks_available_deployment(model=model, request_kwargs=request_kwargs)
+                elif not resolved:
+                    with pytest.raises(litellm.BadRequestError):
+                        router._common_checks_available_deployment(model=model, request_kwargs=request_kwargs)
+                else:
+                    _, deployments = router._common_checks_available_deployment(
+                        model=model, request_kwargs=request_kwargs
+                    )
+                    assert [d["model_name"] for d in deployments] == callable_names, (principal, model)
+
+    def test_drop_strategy_markers_keeps_plain_deployments_and_rejects_marker_only_sets(self):
+        router = self._router({})
+        marker = router.model_list[0]
+        plain = {"model_name": "plain", "litellm_params": {"model": "openai/gpt-4o"}}
+
+        assert router._drop_strategy_markers("x", [marker, plain]) == [plain]
+        assert router._drop_strategy_markers("x", [plain]) == [plain]
+        assert router._drop_strategy_markers("x", []) == []
+        with pytest.raises(litellm.BadRequestError, match="strategy router marker"):
+            router._drop_strategy_markers("x", [marker])
+
+    def test_team_deployments_across_teams_unions_one_team_and_rejects_two(self):
+        other_team_marker = {
+            **self._team_marker(self.SIBLING_INTERNAL_NAME),
+            "model_info": {"team_id": self.OTHER_TEAM, "team_public_model_name": self.PUBLIC_NAME},
+        }
+        one_team = self._router({})
+        two_teams = self._router({}, markers=(self._team_marker(self.INTERNAL_NAME), other_team_marker))
+
+        assert [d["model_name"] for d in one_team._team_deployments_across_teams(self.PUBLIC_NAME)] == [
+            self.INTERNAL_NAME
+        ]
+        assert one_team._team_deployments_across_teams("missing") == []
+        with pytest.raises(litellm.BadRequestError, match="multiple teams"):
+            two_teams._team_deployments_across_teams(self.PUBLIC_NAME)
+
+
+    def test_compression_policy_follows_the_same_resolution_for_every_principal(self):
+        from litellm.proxy.guardrails.auto_router_compression import AutoRouterCompressionPolicy, policy_for_model
+
+        marker = self._team_marker(self.INTERNAL_NAME)
+        marker["litellm_params"]["auto_router_routing_compression"] = "headroom-team"
+        router = self._router({}, markers=(marker,))
+        admin = {"metadata": {"user_api_key_auth": SimpleNamespace(user_role="proxy_admin")}}
+        expected = AutoRouterCompressionPolicy(routing="headroom-team", model=None)
+
+        assert policy_for_model(router, self.PUBLIC_NAME, self._team_request(), ()) == expected
+        assert policy_for_model(router, self.PUBLIC_NAME, admin, ()) == expected
+        assert policy_for_model(router, self.PUBLIC_NAME, self._team_request(self.OTHER_TEAM), ()) is None
+        assert policy_for_model(router, self.PUBLIC_NAME, self._team_request(None), ()) is None
+
+
 class TestAutoRouterCompressionDecoupling:
     """An auto router's `auto_router_routing_compression` / `auto_router_model_compression`
     decouple what the routing decision sees from what the model call sees. The one
@@ -13850,6 +14372,49 @@ async def test_router_retry_policy_controls_upstream_attempt_count(
     assert upstream.call_count == expected_upstream_calls
 
 
+@pytest.mark.asyncio
+async def test_generic_call_keeps_the_deployment_name_of_an_azure_ai_model_on_an_azure_openai_host(monkeypatch):
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    router = litellm.Router(
+        model_list=[
+            {
+                "model_name": "aoai-gpt",
+                "litellm_params": {
+                    "model": "azure_ai/gpt-5.4-mini",
+                    "api_base": "https://my-resource.openai.azure.com",
+                    "api_key": "deployment-key",
+                },
+            }
+        ]
+    )
+
+    with respx.mock(assert_all_called=True) as respx_mock:
+        upstream = respx_mock.post(host="my-resource.openai.azure.com", path__regex=r"^/openai/.*responses$").mock(
+            return_value=httpx.Response(
+                200,
+                json={
+                    "id": "resp_1",
+                    "object": "response",
+                    "created_at": 1,
+                    "status": "completed",
+                    "model": "gpt-5.4-mini",
+                    "output": [
+                        {
+                            "type": "message",
+                            "id": "msg_1",
+                            "role": "assistant",
+                            "status": "completed",
+                            "content": [{"type": "output_text", "text": "hi", "annotations": []}],
+                        }
+                    ],
+                },
+            )
+        )
+        await router.aresponses(model="aoai-gpt", input="hi")
+
+    assert json.loads(upstream.calls.last.request.content)["model"] == "gpt-5.4-mini"
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "retry_policy,upstream_error",
@@ -14728,3 +15293,100 @@ def test_router_stays_quiet_when_a_deployment_drop_params_is_a_flag(value, caplo
         )
 
     assert "is not a flag value" not in caplog.text
+
+
+def test_get_candidate_model_ids_for_route_covers_model_name_and_pattern():
+    """
+    get_candidate_model_ids_for_route resolves a route the way the router does, so a
+    pre-call check can tell a genuine cross-group route from same-group unavailability.
+    A concrete model group returns its member ids; a wildcard/pattern deployment is
+    included for a concrete model it matches, which the bare model_name index misses.
+    The unprefixed-name case must resolve through get_deployments_by_pattern (which retries
+    the provider-qualified form), not a bare pattern_router.route that only sees the literal
+    name. Regression guard for the LIT-7195 tier-change discriminator's team/pattern gaps.
+    """
+    router = Router(
+        model_list=[
+            {
+                "model_name": "grp",
+                "litellm_params": {"model": "openai/gpt-4o", "api_key": "sk-a", "api_base": "https://x.invalid"},
+                "model_info": {"id": "dep-a"},
+            },
+            {
+                "model_name": "grp",
+                "litellm_params": {"model": "openai/gpt-4o-mini", "api_key": "sk-b", "api_base": "https://x.invalid"},
+                "model_info": {"id": "dep-b"},
+            },
+            {
+                "model_name": "openai/*",
+                "litellm_params": {"model": "openai/*", "api_key": "sk-c", "api_base": "https://x.invalid"},
+                "model_info": {"id": "dep-wild"},
+            },
+        ]
+    )
+
+    assert router.get_candidate_model_ids_for_route(model="grp") == frozenset({"dep-a", "dep-b"})
+    assert "dep-wild" in router.get_candidate_model_ids_for_route(model="openai/gpt-4o-some-new-model")
+    # unprefixed name whose provider resolves to openai: only get_deployments_by_pattern's
+    # provider-qualified retry matches "openai/*"; a bare route() on the literal name misses it
+    assert "dep-wild" in router.get_candidate_model_ids_for_route(model="gpt-5")
+
+
+def test_deployment_ids_stringifies_ids_and_skips_entries_without_a_model_info_id():
+    deployments = (
+        {"model_info": {"id": "a"}},
+        {"model_info": {"id": 2}},
+        {"model_info": {}},
+        {"no_model_info": True},
+    )
+    assert Router._deployment_ids(deployments) == frozenset({"a", "2"})
+
+
+def test_cached_model_info_lookups_match_uncached_and_reset_on_model_list_change():
+    def deployment(max_output_tokens: int) -> Deployment:
+        return Deployment(
+            model_name="grp",
+            litellm_params=LiteLLM_Params(model="openai/gpt-4o", api_key="sk-a"),
+            model_info=ModelInfo(id="dep-a", max_output_tokens=max_output_tokens),
+        )
+
+    router = Router(model_list=[deployment(100).model_dump()])
+
+    assert router.cached_model_group_info("grp") == router.get_model_group_info("grp")
+    first = router.cached_deployment_model_info("dep-a", "openai/gpt-4o")
+    assert first == router.get_deployment_model_info(model_id="dep-a", model_name="openai/gpt-4o")
+    assert router.cached_deployment_model_info("dep-a", "openai/gpt-4o") is first
+
+    router.upsert_deployment(deployment(200))
+
+    assert router.cached_deployment_model_info("dep-a", "openai/gpt-4o")["max_output_tokens"] == 200
+    assert router.cached_model_group_info("grp").max_output_tokens == 200
+
+
+class _OpenBreakerRedis:
+    def __init__(self) -> None:
+        from litellm.caching.redis_cache import RedisCircuitBreaker
+
+        self._circuit_breaker = RedisCircuitBreaker(failure_threshold=3, recovery_timeout=60)
+        for _ in range(3):
+            self._circuit_breaker.record_failure()
+
+    @_redis_circuit_breaker_guard
+    async def async_get_cache(self, key, **kwargs):
+        raise AssertionError("never reached")
+
+
+@pytest.mark.asyncio
+async def test_an_open_circuit_breaker_skips_the_session_binding_without_a_warning(caplog):
+    router = litellm.Router(
+        model_list=[{"model_name": "haiku", "litellm_params": {"model": "anthropic/claude-haiku-4-5", "api_key": "k"}}]
+    )
+    router._claude_code_session_router_cache = DualCache(redis_cache=_OpenBreakerRedis())  # pyright: ignore[reportArgumentType]  # duck-typed Redis double
+    caplog.clear()
+
+    with caplog.at_level(logging.DEBUG, logger="LiteLLM Router"):
+        binding = await router._get_claude_code_session_router_binding("quiet-session")
+
+    assert binding is None
+    assert [record.getMessage() for record in caplog.records if record.levelno >= logging.WARNING] == []
+    assert any("circuit breaker is open" in record.getMessage() for record in caplog.records)
diff --git a/tests/test_litellm/test_router/test_io_token_rate_limits.py b/tests/test_litellm/test_router/test_io_token_rate_limits.py
index a5a68271111..3cef1c7bb63 100644
--- a/tests/test_litellm/test_router/test_io_token_rate_limits.py
+++ b/tests/test_litellm/test_router/test_io_token_rate_limits.py
@@ -1039,3 +1039,31 @@ class TestContextSlotRetention:
         assert deployment is not None
         router._update_kwargs_with_deployment(deployment=deployment.model_dump(), kwargs=kwargs)
         assert get_io_token_rate_limit_request_kwargs() is kwargs
+
+
+@pytest.mark.asyncio
+async def test_the_deployment_itpm_reservation_counts_the_request_off_the_event_loop():
+    from litellm.utils import get_utc_datetime
+    from tests.large_text import text
+    from tests.test_litellm.litellm_core_utils.event_loop_lag import (
+        assert_loop_stayed_free,
+        timed_with_loop_lags,
+        warm_tokenizer,
+    )
+
+    dual_cache = DualCache()
+    check = ModelRateLimitingCheck(dual_cache=dual_cache)
+    warm_tokenizer("anthropic/claude-fable-5")
+    deployment = {
+        "litellm_params": {"model": "anthropic/claude-fable-5", "itpm": 10_000_000},
+        "model_info": {"id": "io-loop-id"},
+        "model_name": "claude",
+    }
+    set_io_token_rate_limit_request_kwargs({"messages": [{"role": "user", "content": text * 100}], "metadata": {}})
+
+    _, took, lags = await timed_with_loop_lags(lambda: check.async_pre_call_check(deployment))
+
+    minute = get_utc_datetime().strftime("%H-%M")
+    reserved = await dual_cache.async_get_cache(key=f"global_router:io-loop-id:anthropic/claude-fable-5:itpm:{minute}")
+    assert reserved > 100_000
+    assert_loop_stayed_free(took, lags)
diff --git a/tests/test_litellm/test_router_model_cost_isolation.py b/tests/test_litellm/test_router_model_cost_isolation.py
index 30b265905f3..bd38eecd1c6 100644
--- a/tests/test_litellm/test_router_model_cost_isolation.py
+++ b/tests/test_litellm/test_router_model_cost_isolation.py
@@ -2361,3 +2361,31 @@ def test_a_config_deployment_dropped_for_a_permanent_reason_is_not_retried_on_re
 
     assert router.get_model_names() == ["control-model"]
     assert router.deployment_names == names_after_boot
+
+
+def test_price_data_reload_refreshes_the_cached_model_group_and_deployment_info(monkeypatch):
+    """
+    Budget reservation reads pricing through the router's lru-cached group and
+    deployment lookups. A reload swaps the catalog without touching model_list, so
+    unless the replay clears those caches the next reservation prices against the
+    old catalog until some unrelated model-list change happens to evict it.
+    """
+    router = Router(
+        model_list=[
+            {
+                "model_name": "grp",
+                "litellm_params": {"model": "openai/gpt-4o", "api_key": "k"},
+                "model_info": {"id": "dep-a"},
+            }
+        ]
+    )
+    old_price = router.cached_model_group_info("grp").input_cost_per_token
+    assert router.cached_deployment_model_info("dep-a", "openai/gpt-4o")["input_cost_per_token"] == old_price
+
+    new_price = old_price * 10
+    fresh_catalog = copy.deepcopy(litellm.model_cost)
+    fresh_catalog["gpt-4o"]["input_cost_per_token"] = new_price
+    _simulate_price_data_reload_with_provider_sets(monkeypatch, fresh_catalog)
+
+    assert router.cached_model_group_info("grp").input_cost_per_token == new_price
+    assert router.cached_deployment_model_info("dep-a", "openai/gpt-4o")["input_cost_per_token"] == new_price
diff --git a/tests/test_litellm/test_utils.py b/tests/test_litellm/test_utils.py
index fee5e3a2e4c..7753cb7d770 100644
--- a/tests/test_litellm/test_utils.py
+++ b/tests/test_litellm/test_utils.py
@@ -1,11 +1,16 @@
 import asyncio
+import contextlib
 import json
 import logging
 import os
+import queue
+import threading
 from datetime import datetime, timedelta, timezone
+from collections.abc import Iterator
 from typing import Final
 from unittest.mock import AsyncMock, MagicMock, patch
 
+import httpx
 import pytest
 import respx
 from jsonschema import validate
@@ -13,6 +18,7 @@ from jsonschema import validate
 
 import litellm
 from litellm._internal_context import is_internal_call
+from litellm.constants import DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT
 from litellm._logging import (
     CorrelationContextFilter,
     JsonFormatter,
@@ -54,6 +60,12 @@ from litellm.utils import (
 # Adds the parent directory to the system path
 
 
+def test_cloudflare_model_info_includes_rpm(local_model_cost_map: None) -> None:
+    assert litellm.get_model_info("cloudflare/@cf/meta/llama-3.1-8b-instruct-fp8")["rpm"] == 300
+    assert litellm.get_model_info("cloudflare/@cf/moonshotai/kimi-k2.6")["rpm"] == 20
+    assert litellm.get_model_info("cloudflare/@cf/openai/whisper-large-v3-turbo")["rpm"] == 720
+
+
 def test_get_utc_datetime_returns_current_aware_utc_time() -> None:
     before: Final = datetime.now(timezone.utc)
     result: Final = litellm.utils.get_utc_datetime()
@@ -808,6 +820,7 @@ def validate_model_cost_values(model_data, exceptions=None):
         "input_cost_per_second",
         "output_cost_per_second",
         "output_cost_per_second_480p",
+        "output_cost_per_second_720p",
         "output_cost_per_second_1080p",
         "output_cost_per_second_4k",
         "input_cost_per_query",
@@ -1031,6 +1044,7 @@ def test_aaamodel_prices_and_context_window_json_is_valid():
                 "output_cost_per_pixel": {"type": "number"},
                 "output_cost_per_second": {"type": "number"},
                 "output_cost_per_second_480p": {"type": "number"},
+                "output_cost_per_second_720p": {"type": "number"},
                 "output_cost_per_second_1080p": {"type": "number"},
                 "output_cost_per_second_4k": {"type": "number"},
                 "output_cost_per_token": {"type": "number"},
@@ -1403,23 +1417,35 @@ def test_supports_tool_choice_simple_tests():
         is True
     )
 
-    assert (
-        litellm.utils.supports_tool_choice(model="us.amazon.nova-micro-v1:0") is False
-    )
-    assert (
-        litellm.utils.supports_tool_choice(model="bedrock/us.amazon.nova-micro-v1:0")
-        is False
-    )
-    assert (
-        litellm.utils.supports_tool_choice(
-            model="us.amazon.nova-micro-v1:0", custom_llm_provider="bedrock_converse"
-        )
-        is False
-    )
-
     assert litellm.utils.supports_tool_choice(model="perplexity/sonar") is False
 
 
+@pytest.mark.usefixtures("local_model_cost_map")
+@pytest.mark.parametrize(
+    "model",
+    [
+        "amazon.nova-lite-v1:0",
+        "amazon.nova-micro-v1:0",
+        "amazon.nova-pro-v1:0",
+        "apac.amazon.nova-lite-v1:0",
+        "apac.amazon.nova-micro-v1:0",
+        "apac.amazon.nova-pro-v1:0",
+        "bedrock/us-gov-east-1/amazon.nova-pro-v1:0",
+        "bedrock/us-gov-west-1/amazon.nova-lite-v1:0",
+        "bedrock/us-gov-west-1/amazon.nova-micro-v1:0",
+        "bedrock/us-gov-west-1/amazon.nova-pro-v1:0",
+        "eu.amazon.nova-lite-v1:0",
+        "eu.amazon.nova-micro-v1:0",
+        "eu.amazon.nova-pro-v1:0",
+        "us.amazon.nova-lite-v1:0",
+        "us.amazon.nova-micro-v1:0",
+        "us.amazon.nova-pro-v1:0",
+    ],
+)
+def test_amazon_nova_v1_understanding_models_support_tool_choice(model: str) -> None:
+    assert litellm.utils.supports_tool_choice(model=model) is True
+
+
 def test_check_provider_match():
     """
     Test the _check_provider_match function for various provider scenarios
@@ -2382,6 +2408,28 @@ def test_register_model_with_scientific_notation():
     _invalidate_model_cost_lowercase_map()
 
 
+@respx.mock
+def test_register_model_url_fetch_uses_single_attempt(monkeypatch):
+    monkeypatch.delenv("LITELLM_LOCAL_MODEL_COST_MAP", raising=False)
+    monkeypatch.setattr(litellm, "model_cost", dict(litellm.model_cost))
+    before = dict(litellm.model_cost)
+    threads_before = {thread.name for thread in threading.enumerate()}
+    route = respx.get("https://example.invalid/custom_pricing.json").mock(
+        return_value=httpx.Response(503)
+    )
+
+    litellm.register_model(model_cost="https://example.invalid/custom_pricing.json")
+
+    threads_after = {thread.name for thread in threading.enumerate()}
+    assert route.call_count == 1
+    assert not (threads_after - threads_before) & {"litellm-model-cost-map-retry"}
+    assert not any(
+        thread.name == "litellm-model-cost-map-retry" and thread.is_alive()
+        for thread in threading.enumerate()
+    )
+    assert litellm.model_cost.keys() >= before.keys()
+
+
 def test_register_model_openrouter_without_slash():
     """
     Test that register_model handles openrouter models without '/' in the name.
@@ -6164,3 +6212,135 @@ def test_load_credentials_from_list_fills_kwargs_from_the_loaded_credential_with
         "api_key": "sk-from-db",
     }
     assert _credential_warnings(caplog) == []
+
+
+_MOCK_STREAM_ID: Final = "chatcmpl-mock-stream"
+_ChunkSnapshot = tuple[str, tuple[str | None, ...], Usage | None]
+
+
+def _snapshot(chunk: ModelResponseStream) -> _ChunkSnapshot:
+    return chunk.id, tuple(choice.delta.content for choice in chunk.choices), getattr(chunk, "usage", None)
+
+
+def _mock_stream_snapshots(mock_response: object, prompt_tokens: int | None) -> list[_ChunkSnapshot]:
+    from litellm.utils import mock_completion_streaming_obj
+
+    return [
+        _snapshot(chunk)
+        for chunk in mock_completion_streaming_obj(
+            ModelResponseStream(id=_MOCK_STREAM_ID, model="gpt-5.4-mini"),
+            mock_response=mock_response,
+            model="gpt-5.4-mini",
+            prompt_tokens=prompt_tokens,
+        )
+    ]
+
+
+async def _async_mock_stream_snapshots(mock_response: object, prompt_tokens: int | None) -> list[_ChunkSnapshot]:
+    from litellm.utils import async_mock_completion_streaming_obj
+
+    return [
+        _snapshot(chunk)
+        async for chunk in async_mock_completion_streaming_obj(
+            ModelResponseStream(id=_MOCK_STREAM_ID, model="gpt-5.4-mini"),
+            mock_response=mock_response,
+            model="gpt-5.4-mini",
+            prompt_tokens=prompt_tokens,
+        )
+    ]
+
+
+_CONTENT_SNAPSHOTS: Final = [(_MOCK_STREAM_ID, (content,), None) for content in ("hel", "lo ", "wor", "ld")]
+
+
+def _assert_trailing_usage_chunk(snapshots: list[_ChunkSnapshot], prompt_tokens: int) -> None:
+    assert snapshots[:-1] == _CONTENT_SNAPSHOTS
+    chunk_id, choices, usage = snapshots[-1]
+    assert chunk_id == _MOCK_STREAM_ID
+    assert choices == ()
+    assert usage is not None
+    assert usage.prompt_tokens == prompt_tokens
+    assert usage.completion_tokens == DEFAULT_MOCK_RESPONSE_COMPLETION_TOKEN_COUNT
+    assert usage.total_tokens == prompt_tokens + usage.completion_tokens
+
+
+@pytest.mark.parametrize("prompt_tokens", (51234, 0))
+def test_mock_completion_streaming_obj_emits_usage_chunk_with_admission_prompt_tokens(prompt_tokens: int) -> None:
+    _assert_trailing_usage_chunk(_mock_stream_snapshots("hello world", prompt_tokens), prompt_tokens)
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("prompt_tokens", (51234, 0))
+async def test_async_mock_completion_streaming_obj_emits_usage_chunk_with_admission_prompt_tokens(
+    prompt_tokens: int,
+) -> None:
+    _assert_trailing_usage_chunk(await _async_mock_stream_snapshots("hello world", prompt_tokens), prompt_tokens)
+
+
+def test_mock_completion_streaming_obj_emits_no_usage_chunk_without_admission_prompt_tokens() -> None:
+    assert _mock_stream_snapshots("hello world", None) == _CONTENT_SNAPSHOTS
+
+
+@pytest.mark.asyncio
+async def test_async_mock_completion_streaming_obj_emits_no_usage_chunk_without_admission_prompt_tokens() -> None:
+    assert await _async_mock_stream_snapshots("hello world", None) == _CONTENT_SNAPSHOTS
+
+
+def test_mock_completion_streaming_obj_passes_prebuilt_stream_chunk_through_without_usage_chunk() -> None:
+    prebuilt: Final = ModelResponseStream(
+        model="gpt-5.4-mini", choices=[StreamingChoices(index=0, delta=Delta(role="assistant", content="prebuilt"))]
+    )
+
+    assert _mock_stream_snapshots(prebuilt, 51234) == [(prebuilt.id, ("prebuilt",), None)]
+
+
+@pytest.mark.asyncio
+async def test_async_mock_completion_streaming_obj_raises_mock_exception_before_usage_chunk() -> None:
+    mock_exception: Final = litellm.MockException(
+        status_code=500, message="boom", llm_provider="openai", model="gpt-5.4-mini"
+    )
+    with pytest.raises(litellm.MockException):
+        await _async_mock_stream_snapshots(mock_exception, 51234)
+
+
+
+@contextlib.contextmanager
+def _recording_hidden_params_at_submit(submit_target: str) -> "Iterator[queue.SimpleQueue[dict[str, object]]]":
+    seen: Final = queue.SimpleQueue()
+
+    def record_submit(_fn, *args, **_kwargs):
+        response: Final = next(arg for arg in args if isinstance(arg, litellm.ModelResponse))
+        seen.put(dict(response._hidden_params))
+        return MagicMock()
+
+    with patch(submit_target, side_effect=record_submit):
+        yield seen
+
+
+@pytest.mark.asyncio
+async def test_acompletion_finishes_response_metadata_before_handing_the_response_to_the_logging_thread(monkeypatch):
+    monkeypatch.setattr(litellm, "success_callback", [lambda kwargs, response, start_time, end_time: None])
+    with _recording_hidden_params_at_submit("litellm.litellm_core_utils.litellm_logging.executor.submit") as seen:
+        await litellm.acompletion(
+            model="gpt-5.5",
+            messages=[{"role": "user", "content": "hi"}],
+            mock_response="Hello there!",
+            num_retries=0,
+        )
+    snapshot: Final = seen.get_nowait()
+    assert snapshot["litellm_call_id"]
+    assert snapshot["response_cost"] is not None
+    assert snapshot["api_base"]
+
+
+def test_completion_finishes_response_metadata_before_handing_the_response_to_the_logging_thread():
+    with _recording_hidden_params_at_submit("litellm.utils.executor.submit") as seen:
+        litellm.completion(
+            model="gpt-5.5",
+            messages=[{"role": "user", "content": "hi"}],
+            mock_response="Hello there!",
+        )
+    snapshot: Final = seen.get_nowait()
+    assert snapshot["litellm_call_id"]
+    assert snapshot["response_cost"] is not None
+    assert snapshot["api_base"]
diff --git a/tests/test_litellm/test_video_generation.py b/tests/test_litellm/test_video_generation.py
index 2a60ff9c4b5..f3cd4618078 100644
--- a/tests/test_litellm/test_video_generation.py
+++ b/tests/test_litellm/test_video_generation.py
@@ -532,6 +532,32 @@ class TestVideoGeneration:
         assert abs(cost_for("runwayml/seedance2_5", "480p", 8.0) - 1.6) < 0.001
         assert abs(cost_for("runwayml/gen4.5", None, 8.0) - 0.96) < 0.001
 
+    def test_completion_cost_xai_imagine_video_720p_tier_from_cost_map(self, monkeypatch):
+        """720p xAI Imagine Video requests bill the published 720p rate, not the 480p base rate."""
+        from litellm.cost_calculator import completion_cost
+
+        local_map_path = os.path.join(
+            os.path.dirname(__file__), "..", "..", "model_prices_and_context_window.json"
+        )
+        with open(local_map_path, "r") as f:
+            monkeypatch.setattr(litellm, "model_cost", json.load(f))
+
+        def cost_for(model: str, resolution: str, duration: float) -> float:
+            mock_response = MagicMock()
+            mock_response.usage = {"duration_seconds": duration, "video_resolution": resolution}
+            type(mock_response)._hidden_params = {}
+            return completion_cost(
+                completion_response=mock_response,
+                model=model,
+                call_type="create_video",
+                custom_llm_provider="xai",
+            )
+
+        assert abs(cost_for("xai/grok-imagine-video", "720p", 10.0) - 0.7) < 0.001
+        assert abs(cost_for("xai/grok-imagine-video-1.5", "720p", 10.0) - 1.4) < 0.001
+        assert abs(cost_for("xai/grok-imagine-video-1.5", "480p", 10.0) - 0.8) < 0.001
+        assert abs(cost_for("xai/grok-imagine-video-1.5", "1080p", 10.0) - 2.5) < 0.001
+
     def test_completion_cost_veo_31_tiers_pin_published_rates(self, monkeypatch):
         """The gemini and vertex_ai veo 3.1 entries bill Google's published per-second tier rates."""
         from litellm.cost_calculator import completion_cost
diff --git a/tests/test_litellm/types/test_router.py b/tests/test_litellm/types/test_router.py
index fd933a9d993..7fcb76b638f 100644
--- a/tests/test_litellm/types/test_router.py
+++ b/tests/test_litellm/types/test_router.py
@@ -1,6 +1,7 @@
 import logging
 
 import pytest
+from pydantic import ValidationError
 
 from litellm.types.router import (
     SPECIAL_MODEL_INFO_PARAMS,
@@ -122,3 +123,26 @@ def test_drop_params_flags_and_strings_log_nothing(value, caplog):
     with caplog.at_level(logging.WARNING, logger="LiteLLM"):
         GenericLiteLLMParams(drop_params=value)
     assert caplog.text == ""
+
+
+def test_aws_session_tags_round_trip_as_sts_shaped_pairs():
+    """The deployment field keeps the exact Key/Value shape STS AssumeRole expects."""
+    params = LiteLLM_Params(
+        model="bedrock/anthropic.claude-opus-5",
+        aws_session_tags=[{"Key": "team", "Value": "genai"}, {"Key": "env", "Value": "prod"}],
+    )
+
+    assert params.model_dump(exclude_none=True)["aws_session_tags"] == [
+        {"Key": "team", "Value": "genai"},
+        {"Key": "env", "Value": "prod"},
+    ]
+
+
+@pytest.mark.parametrize(
+    "aws_session_tags",
+    ["team=genai", {"team": "genai"}, [{"key": "team", "value": "genai"}], [{"Key": "team"}]],
+    ids=["string", "flat-dict", "lowercase-keys", "missing-value"],
+)
+def test_aws_session_tags_reject_shapes_sts_would_refuse(aws_session_tags):
+    with pytest.raises(ValidationError, match="aws_session_tags"):
+        LiteLLM_Params(model="bedrock/anthropic.claude-opus-5", aws_session_tags=aws_session_tags)
diff --git a/tests/test_litellm_rust/README.md b/tests/test_litellm_rust/README.md
new file mode 100644
index 00000000000..4c117fb846b
--- /dev/null
+++ b/tests/test_litellm_rust/README.md
@@ -0,0 +1,13 @@
+# Rust OCR bridge tests
+
+This suite covers OCR requests through LiteLLM's compiled Rust extension. OCR behavior tests live under `ocr/`; reusable OCR request, callback, and recording-server fixtures live under `support/`
+
+A test name identifies the OCR entrypoint or callback under test and its expected observable result. Parameter IDs state the execution mode or credential case. Keep multiple assertions together only when they prove one request, mutation, failure, or callback lifecycle behavior. Record callback observations and assert them after the callback returns because production logging can swallow callback exceptions
+
+`ocr/test_requests.py` covers provider payloads, file preparation, endpoint and credential resolution, normalized responses, errors, timeouts, and Azure token-provider behavior. `ocr/test_callbacks.py` covers OCR callback inputs, mutations, ordering, context, failure handling, concurrency, and cleanup. `ocr/test_guardrails.py` covers OCR post-call blocking and response replacement. These contract modules call the Rust bridge directly. `ocr/test_dispatch.py` has the single public API dispatch test, covering enabled native dispatch and disabled Python dispatch. `test_ocr.py` is a strict smoke test of the compiled Rust OCR transport
+
+Run `make test-rust-extension` as the acceptance command. It builds a fresh wheel, installs that wheel into a temporary environment, requires `LITELLM_RUST=1`, and runs this suite with isolated Python imports
+
+Collection fails when `LITELLM_RUST=1` is set but the compiled `_native` module cannot be imported. The autouse fixture isolates callback and configuration state but does not select a backend. Native contract tests call `litellm.rust_bridge.ocr` directly, while the strict dispatch test explicitly enables and disables Rust and records which OCR entrypoint runs
+
+The OCR contract modules are non-strict expected failures until the retained callback implementation from #40070 lands. The public dispatch test remains strict. Passing contract cases appear as XPASS so staging coverage stays visible
diff --git a/tests/test_litellm_rust/conftest.py b/tests/test_litellm_rust/conftest.py
index 02d274bb405..b0c75d9d2f5 100644
--- a/tests/test_litellm_rust/conftest.py
+++ b/tests/test_litellm_rust/conftest.py
@@ -1,24 +1,132 @@
+import asyncio
 import os
+from collections.abc import AsyncIterator, Generator, Iterator
+from concurrent.futures import ThreadPoolExecutor
+from contextlib import ExitStack, contextmanager
+from types import ModuleType
+from typing import Final, cast
 
 import pytest
+import pytest_asyncio
+
+import litellm
+from litellm import utils
+from litellm.litellm_core_utils import litellm_logging
+from litellm.litellm_core_utils.logging_worker import GLOBAL_LOGGING_WORKER
+from litellm.rust_bridge.configuration import (  # pyright: ignore[reportPrivateUsage]  # preserve raw configuration state in test isolation
+    _CONFIGURATION,
+    _parse_env_bool,
+)
+from tests.test_litellm_rust.support.callback_recorder import drain_logging
+from tests.test_litellm_rust.support.recording_server import RecordingServer, recording_service
+
+CALLBACK_ATTRIBUTES: Final = (
+    "callbacks",
+    "input_callback",
+    "success_callback",
+    "failure_callback",
+    "_async_input_callback",
+    "_async_success_callback",
+    "_async_failure_callback",
+)
+EXPECTED_FAILURE_REASONS: Final = {
+    "ocr/test_callbacks.py": "requires the OCR callback lifecycle implementation from #40070",
+    "ocr/test_guardrails.py": "requires the OCR guardrail lifecycle implementation from #40070",
+    "ocr/test_requests.py": "requires the OCR request and Azure authentication implementation from #40070",
+}
 
 
-def pytest_collection_modifyitems(items):
-    rust_enabled = os.environ.get("LITELLM_RUST", "").strip().lower() in {
-        "1",
-        "true",
-        "yes",
-        "on",
-    }
-    if not rust_enabled:
-        skip = pytest.mark.skip(reason="requires LITELLM_RUST=1 and a compiled Rust extension")
+def _list_attribute(container: ModuleType, attribute: str) -> list[object]:
+    value: Final = getattr(container, attribute)
+    if not isinstance(value, list):
+        raise AssertionError(f"{container.__name__}.{attribute} is not a list")
+    return cast(list[object], value)
+
+
+@contextmanager
+def _isolated_list(container: ModuleType, attribute: str) -> Iterator[None]:
+    source: Final = _list_attribute(container, attribute)
+    original: Final = list(source)
+    source.clear()  # mutable-ok: test isolation mutates global registries by design
+    try:
+        yield
+    finally:
+        source.clear()
+        source.extend(original)
+        setattr(container, attribute, source)
+
+
+@contextmanager
+def _rebound(container: object, attribute: str, value: object) -> Iterator[None]:
+    original: Final[object] = getattr(container, attribute)
+    setattr(container, attribute, value)
+    try:
+        yield
+    finally:
+        setattr(container, attribute, original)
+
+
+@pytest_asyncio.fixture(autouse=True, loop_scope="function")
+async def isolate_ocr_test_state() -> AsyncIterator[None]:
+    with ExitStack() as stack:
+        for attribute in CALLBACK_ATTRIBUTES:
+            stack.enter_context(_isolated_list(litellm, attribute))
+        stack.enter_context(_isolated_list(litellm_logging, "_in_memory_loggers"))  # pyright: ignore[reportPrivateUsage]  # no public callback-cache accessor
+        stack.enter_context(_rebound(utils, "callback_list", []))  # rebind-ok: isolate legacy callback registry
+        stack.enter_context(_rebound(litellm, "cache", None))  # test-quality-ok: isolate process-global cache
+        stack.enter_context(_rebound(_CONFIGURATION, "override", None))
+        executor: Final = ThreadPoolExecutor(thread_name_prefix="rust-ocr-test-logging")
+        stack.enter_context(_rebound(utils, "executor", executor))
+        try:
+            yield
+        finally:
+            try:
+                await drain_logging()
+            finally:
+                await asyncio.to_thread(executor.shutdown, wait=True)
+                await GLOBAL_LOGGING_WORKER.stop()
+
+
+@pytest.fixture
+def recording_server() -> Generator[RecordingServer]:
+    with recording_service() as server:
+        yield server
+
+
+def pytest_collection_modifyitems(items: list[pytest.Item]) -> None:
+    for item in items:
+        if "test_litellm_rust" not in item.path.parts:
+            continue
+        relative_path: Final = "/".join(item.path.parts[item.path.parts.index("test_litellm_rust") + 1 :])
+        reason: Final = EXPECTED_FAILURE_REASONS.get(relative_path)
+        if reason is not None:
+            item.add_marker(pytest.mark.xfail(reason=reason, strict=False))
+
+    if not _parse_env_bool(os.environ.get("LITELLM_RUST")):
+        skip: Final = pytest.mark.skip(reason="requires LITELLM_RUST=1 and a compiled Rust extension")
         for item in items:
-            item.add_marker(skip)
+            if "test_litellm_rust" in item.path.parts:
+                item.add_marker(skip)
         return
 
     try:
         from litellm.rust_bridge import _native  # noqa: F401  # validates the installed extension
     except ImportError as error:
-        raise pytest.UsageError(
-            "LITELLM_RUST=1 requires a compiled litellm.rust_bridge._native extension"
-        ) from error
+        raise pytest.UsageError("LITELLM_RUST=1 requires a compiled litellm.rust_bridge._native extension") from error
+
+
+@pytest.fixture
+def isolated_azure_auth(monkeypatch: pytest.MonkeyPatch) -> None:
+    for name in (
+        "AZURE_AI_API_KEY",
+        "AZURE_AI_API_BASE",
+        "AZURE_AD_TOKEN",
+        "AZURE_TENANT_ID",
+        "AZURE_CLIENT_ID",
+        "AZURE_CLIENT_SECRET",
+        "AZURE_USERNAME",
+        "AZURE_PASSWORD",
+    ):
+        monkeypatch.delenv(name, raising=False)
+    monkeypatch.setattr(litellm, "api_key", None)
+    monkeypatch.setattr(litellm, "enable_azure_ad_token_refresh", False)
diff --git a/tests/test_litellm_rust/ocr/__init__.py b/tests/test_litellm_rust/ocr/__init__.py
new file mode 100644
index 00000000000..8b137891791
--- /dev/null
+++ b/tests/test_litellm_rust/ocr/__init__.py
@@ -0,0 +1 @@
+
diff --git a/tests/test_litellm_rust/ocr/test_callbacks.py b/tests/test_litellm_rust/ocr/test_callbacks.py
new file mode 100644
index 00000000000..b08446412c0
--- /dev/null
+++ b/tests/test_litellm_rust/ocr/test_callbacks.py
@@ -0,0 +1,513 @@
+import asyncio
+import copy
+import queue
+import threading
+from typing import Final
+
+import pytest
+
+import litellm
+from litellm.integrations.custom_logger import CustomLogger
+from litellm.llms.base_llm.ocr.transformation import OCRResponse
+from tests.test_litellm_rust.support.callback_recorder import RecordingLogger
+from tests.test_litellm_rust.support.requests import (
+    OCR_DOCUMENT,
+    OCR_RESPONSE,
+    call_native_aocr,
+    call_native_ocr,
+    request_body,
+    request_headers,
+)
+from tests.test_litellm_rust.support.recording_server import RecordingServer, ResponseSpec
+
+pytestmark = pytest.mark.requires_rust_extension
+
+
+@pytest.fixture
+def ocr_server(recording_server: RecordingServer) -> RecordingServer:
+    recording_server.default_response = ResponseSpec(body=OCR_RESPONSE)
+    return recording_server
+
+
+def call_native_ocr_with_callbacks(server: RecordingServer, callbacks: list[CustomLogger], **kwargs: object):
+    return call_native_ocr(server, callbacks=callbacks, **kwargs)
+
+
+async def call_native_aocr_with_callbacks(server: RecordingServer, callbacks: list[CustomLogger], **kwargs: object):
+    return await call_native_aocr(server, callbacks=callbacks, **kwargs)
+
+
+def test_native_ocr_pre_call_callback_receives_transformed_provider_request(ocr_server: RecordingServer) -> None:
+    observations: Final = []
+
+    class Observe(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            observations.append((model, copy.deepcopy(kwargs["additional_args"])))
+
+    call_native_ocr_with_callbacks(ocr_server, [Observe()], pages=[0])
+
+    assert len(observations) == 1
+    model, additional_args = observations[0]
+    assert model == "mistral-ocr-latest"
+    assert additional_args["api_base"] == f"{ocr_server.base_url}/v1/ocr"
+    assert additional_args["complete_input_dict"] == {
+        "model": "mistral-ocr-latest",
+        "document": OCR_DOCUMENT,
+        "pages": [0],
+    }
+
+
+@pytest.mark.parametrize("raise_after_edit", [False, True], ids=["callback-returns", "callback-raises"])
+def test_native_ocr_pre_call_body_edit_reaches_next_callback_and_provider(
+    ocr_server: RecordingServer, raise_after_edit: bool
+) -> None:
+    observed: Final = []
+
+    class Edit(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            request_body(kwargs)["include_image_base64"] = True
+            if raise_after_edit:
+                raise RuntimeError("pre-call callback failed")
+
+    class Observe(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            observed.append(copy.deepcopy(request_body(kwargs)))
+
+    call_native_ocr_with_callbacks(ocr_server, [Edit(), Observe()], include_image_base64=False)
+
+    assert observed[0]["include_image_base64"] is True
+    assert ocr_server.requests[0].body["include_image_base64"] is True
+
+
+def test_native_ocr_pre_call_header_edit_reaches_next_callback_and_provider(ocr_server: RecordingServer) -> None:
+    observed: Final = []
+
+    class Edit(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            request_headers(kwargs)["x-audit-tag"] = "reviewed"
+
+    class Observe(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            observed.append(dict(request_headers(kwargs)))
+
+    call_native_ocr_with_callbacks(ocr_server, [Edit(), Observe()])
+
+    assert observed[0]["x-audit-tag"] == "reviewed"
+    assert ocr_server.requests[0].headers["x-audit-tag"] == "reviewed"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+async def test_native_ocr_pre_call_nested_document_edit_updates_caller_callback_and_provider_references(
+    ocr_server: RecordingServer, asynchronous: bool
+) -> None:
+    original: Final = dict(OCR_DOCUMENT)
+    replacement_url: Final = "data:application/pdf;base64,ZGVm"
+    retained: Final = []
+    aliases: Final = []
+
+    class Retain(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            aliases.append(request_body(kwargs)["document"] is original)
+            retained.append(request_body(kwargs)["document"])
+
+    class Edit(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            original["document_url"] = replacement_url
+
+    arguments: Final = {
+        "model": "mistral/mistral-ocr-latest",
+        "document": original,
+        "api_key": "test-key",
+        "api_base": ocr_server.base_url,
+        "callbacks": [Retain(), Edit()],
+    }
+    response: Final = (
+        await call_native_aocr(ocr_server, **arguments)
+        if asynchronous
+        else call_native_ocr(ocr_server, **arguments)
+    )
+
+    assert aliases == [True]
+    assert retained[0]["document_url"] == replacement_url
+    assert original["document_url"] == replacement_url
+    assert ocr_server.requests[0].body["document"]["document_url"] == replacement_url
+    assert response.pages[0].markdown == "native OCR response"
+
+
+def test_native_ocr_pre_call_document_replacement_does_not_mutate_original_document(
+    ocr_server: RecordingServer,
+) -> None:
+    original: Final = dict(OCR_DOCUMENT)
+    replacement: Final = {"type": "document_url", "document_url": "data:application/pdf;base64,ZGVm"}
+    retained: Final = []
+
+    class RetainAndReplace(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            body = request_body(kwargs)
+            retained.append(body["document"])
+            body["document"] = replacement
+
+    call_native_ocr(
+        ocr_server,
+        document=original,
+        callbacks=[RetainAndReplace()],
+    )
+
+    assert retained[0] is original
+    assert original["document_url"] == OCR_DOCUMENT["document_url"]
+    assert ocr_server.requests[0].body["document"] == replacement
+
+
+def test_native_ocr_pre_call_body_rebinding_is_visible_to_callbacks_but_not_provider(
+    ocr_server: RecordingServer,
+) -> None:
+    observed: Final = []
+
+    class Rebind(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            kwargs["additional_args"]["complete_input_dict"] = {"replacement": True}
+
+    class Observe(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            observed.append(request_body(kwargs))
+
+    call_native_ocr_with_callbacks(ocr_server, [Rebind(), Observe()])
+
+    assert observed == [{"replacement": True}]
+    assert ocr_server.requests[0].body == {"model": "mistral-ocr-latest", "document": OCR_DOCUMENT}
+
+
+def test_native_ocr_callback_retained_body_observes_later_callback_mutation(ocr_server: RecordingServer) -> None:
+    queued: Final = []
+
+    class QueuePayload(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            queued.append(request_body(kwargs))
+
+    class Edit(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            request_body(kwargs)["queued-edit"] = True
+
+    call_native_ocr_with_callbacks(ocr_server, [QueuePayload(), Edit()])
+
+    assert queued[0]["queued-edit"] is True
+
+
+def test_native_ocr_success_callback_receives_state_added_by_pre_call_callback(ocr_server: RecordingServer) -> None:
+    token: Final = object()
+    terminal_tokens: queue.SimpleQueue[object] = queue.SimpleQueue()
+    finished: Final = threading.Event()
+
+    class Stash(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            kwargs["test-token"] = token
+
+        def log_success_event(self, kwargs, response_obj, start_time, end_time):
+            terminal_tokens.put(kwargs["test-token"])
+            finished.set()
+
+    call_native_ocr_with_callbacks(ocr_server, [Stash()])
+
+    assert finished.wait(10)
+    assert terminal_tokens.get_nowait() is token
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_success_callback_receives_call_id_metadata_and_response(
+    ocr_server: RecordingServer,
+) -> None:
+    recorder: Final = RecordingLogger()
+
+    await call_native_aocr_with_callbacks(
+        ocr_server,
+        [recorder],
+        litellm_call_id="ocr-success",
+        metadata={"source": "callback-test"},
+    )
+    events: Final = await recorder.wait_for_async("async_log_success_event")
+
+    assert len(events) == 1
+    assert events[0].call_type == "aocr"
+    assert events[0].kwargs["litellm_call_id"] == "ocr-success"
+    assert events[0].kwargs["litellm_params"]["metadata"]["source"] == "callback-test"
+    assert events[0].response.pages[0].markdown == "native OCR response"
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_failure_callbacks_receive_call_type_error_and_no_response(
+    ocr_server: RecordingServer,
+) -> None:
+    ocr_server.enqueue(ResponseSpec(body={"message": "provider unavailable"}, status=500))
+    observations: Final = []
+
+    class Observe(CustomLogger):
+        def log_failure_event(self, kwargs, response_obj, start_time, end_time):
+            observations.append(("sync", kwargs["call_type"], kwargs["exception"], response_obj))
+
+        async def async_log_failure_event(self, kwargs, response_obj, start_time, end_time):
+            observations.append(("async", kwargs["call_type"], kwargs["exception"], response_obj))
+
+    with pytest.raises(litellm.InternalServerError):
+        await call_native_aocr_with_callbacks(ocr_server, [Observe()])
+
+    assert [observation[0] for observation in observations] == ["sync", "async"]
+    assert all(observation[1] == "aocr" for observation in observations)
+    assert all(isinstance(observation[2], litellm.InternalServerError) for observation in observations)
+    assert all(observation[3] is None for observation in observations)
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_pre_call_callback_runs_on_caller_loop_and_thread(ocr_server: RecordingServer) -> None:
+    caller_loop: Final = asyncio.get_running_loop()
+    caller_thread: Final = threading.current_thread()
+    recorder: Final = RecordingLogger()
+
+    await call_native_aocr_with_callbacks(ocr_server, [recorder])
+
+    events: Final = await recorder.wait_for_async("log_pre_api_call")
+    assert len(events) == 1
+    assert events[0].loop is caller_loop
+    assert events[0].thread is caller_thread
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_failure_callbacks_receive_state_added_by_pre_call_callback(
+    ocr_server: RecordingServer,
+) -> None:
+    ocr_server.enqueue(ResponseSpec(body={"message": "provider unavailable"}, status=500))
+    token: Final = object()
+    observed: Final = []
+
+    class TrackInFlightRequest(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            kwargs["request-token"] = token
+
+        def log_failure_event(self, kwargs, response_obj, start_time, end_time):
+            observed.append(("sync", kwargs["request-token"]))
+
+        async def async_log_failure_event(self, kwargs, response_obj, start_time, end_time):
+            observed.append(("async", kwargs["request-token"]))
+
+    with pytest.raises(litellm.InternalServerError):
+        await call_native_aocr_with_callbacks(ocr_server, [TrackInFlightRequest()])
+
+    assert [event for event, _ in observed] == ["sync", "async"]
+    assert all(observed_token is token for _, observed_token in observed)
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_callback_error_does_not_mask_provider_error_or_skip_later_failure_callbacks(
+    ocr_server: RecordingServer,
+) -> None:
+    ocr_server.enqueue(ResponseSpec(body={"message": "provider unavailable"}, status=500))
+    recorder: Final = RecordingLogger()
+
+    class FailingCallback(CustomLogger):
+        def log_failure_event(self, kwargs, response_obj, start_time, end_time):
+            raise RuntimeError("failure callback failed")
+
+        async def async_log_failure_event(self, kwargs, response_obj, start_time, end_time):
+            raise RuntimeError("failure callback failed")
+
+    with pytest.raises(litellm.InternalServerError) as caught:
+        await call_native_aocr_with_callbacks(ocr_server, [FailingCallback(), recorder])
+
+    sync_events: Final = tuple(event for event in recorder.events if event.name == "log_failure_event")
+    async_events: Final = tuple(event for event in recorder.events if event.name == "async_log_failure_event")
+    assert len(sync_events) == 1
+    assert len(async_events) == 1
+    assert sync_events[0].kwargs["exception"] is caught.value
+    assert async_events[0].kwargs["exception"] is caught.value
+    assert "async_log_success_event" not in recorder.names
+
+
+def test_native_ocr_dispatches_each_callback_phase_once_when_logger_is_registered_multiple_times(
+    ocr_server: RecordingServer,
+) -> None:
+    recorder: Final = RecordingLogger()
+
+    call_native_ocr_with_callbacks(
+        ocr_server,
+        [recorder, recorder],
+        success_callback=[recorder],
+        failure_callback=[recorder],
+    )
+    recorder.wait_for("log_success_event")
+
+    assert recorder.names.count("log_pre_api_call") == 1
+    assert recorder.names.count("logging_hook") == 1
+    assert recorder.names.count("log_success_event") == 1
+    assert "log_failure_event" not in recorder.names
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+async def test_native_azure_ocr_resolves_token_before_pre_call_on_caller_context(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    asynchronous: bool,
+) -> None:
+    from contextvars import ContextVar
+    context: Final = ContextVar("azure-token-context", default="missing")
+    context.set("caller")
+    caller_thread: Final = threading.current_thread()
+    caller_loop: Final = asyncio.get_running_loop()
+    observations: Final = []
+
+    class Provider:
+        def __call__(self) -> str:
+            assert context.get() == "caller"
+            assert threading.current_thread() is caller_thread
+            assert asyncio.get_running_loop() is caller_loop
+            observations.append("token")
+            return "caller-token"
+
+    class Edit(CustomLogger):
+        def log_pre_api_call(self, model, _messages, kwargs):
+            assert request_headers(kwargs)["Authorization"] == "Bearer caller-token"
+            observations.append("pre_call")
+            request_headers(kwargs)["Authorization"] = "Bearer edited"
+
+    provider: Final = Provider()
+    arguments: Final = {
+        "model": "azure_ai/mistral-ocr-latest",
+        "api_key": None,
+        "azure_ad_token_provider": provider,
+        "callbacks": [Edit()],
+    }
+    response: Final = (
+        await call_native_aocr(ocr_server, **arguments)
+        if asynchronous
+        else call_native_ocr(ocr_server, **arguments)
+    )
+    assert response.pages[0].markdown == "native OCR response"
+    assert observations == ["token", "pre_call"]
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer edited"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+async def test_native_azure_ocr_token_provider_can_make_nested_native_ocr_call(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    asynchronous: bool,
+) -> None:
+    ocr_server.expected_requests = 2
+    calls: Final = []
+
+    def provider() -> str:
+        calls.append("token")
+        nested: Final = call_native_ocr(ocr_server)
+        assert nested.pages[0].markdown == "native OCR response"
+        return "outer-token"
+
+    arguments: Final = {
+        "model": "azure_ai/mistral-ocr-latest",
+        "api_key": None,
+        "azure_ad_token_provider": provider,
+    }
+    response: Final = (
+        await call_native_aocr(ocr_server, **arguments)
+        if asynchronous
+        else call_native_ocr(ocr_server, **arguments)
+    )
+    assert response.pages[0].markdown == "native OCR response"
+    assert calls == ["token"]
+    assert [request.headers["authorization"] for request in ocr_server.requests] == [
+        "Bearer test-key",
+        "Bearer outer-token",
+    ]
+
+
+@pytest.mark.asyncio
+async def test_concurrent_native_azure_ocr_calls_isolate_token_results_and_error(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+) -> None:
+    ocr_server.expected_requests = 2
+
+    async def request(token: str, fail: bool) -> object:
+        def provider() -> str:
+            if fail:
+                raise ValueError(token)
+            return token
+
+        return await call_native_aocr(
+            ocr_server,
+            model="azure_ai/mistral-ocr-latest",
+            api_key=None,
+            azure_ad_token_provider=provider,
+        )
+
+    responses: Final = await asyncio.gather(
+        request("first", False),
+        request("failed", True),
+        request("second", False),
+        return_exceptions=True,
+    )
+    assert isinstance(responses[0], OCRResponse)
+    assert isinstance(responses[1], litellm.APIConnectionError)
+    assert "Failed to get Azure AD token: failed" in str(responses[1])
+    assert isinstance(responses[2], OCRResponse)
+    assert sorted(request.headers["authorization"] for request in ocr_server.requests) == [
+        "Bearer first",
+        "Bearer second",
+    ]
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("outcome", ["success", "failure", "cancellation"])
+async def test_native_azure_ocr_releases_token_provider_after_terminal_outcome(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    outcome: str,
+) -> None:
+    import gc
+    import weakref
+    from tests.test_litellm_rust.support.callback_recorder import drain_logging
+    class Provider:
+        def __call__(self) -> str:
+            if outcome == "failure":
+                raise ValueError("unavailable")
+            return "caller-token"
+
+    async def invoke() -> weakref.ReferenceType[Provider]:
+        provider: Final = Provider()
+        reference: Final = weakref.ref(provider)
+        if outcome == "failure":
+            ocr_server.expected_requests = 0
+            with pytest.raises(litellm.APIConnectionError):
+                await call_native_aocr(
+                    ocr_server, model="azure_ai/mistral-ocr-latest", api_key=None, azure_ad_token_provider=provider
+                )
+        elif outcome == "cancellation":
+            ocr_server.enqueue(ResponseSpec(body=OCR_RESPONSE, delay=0.1))
+            task: Final = asyncio.create_task(
+                call_native_aocr(
+                    ocr_server,
+                    model="azure_ai/mistral-ocr-latest",
+                    api_key=None,
+                    azure_ad_token_provider=provider,
+                )
+            )
+            await ocr_server.wait_for_requests(1)
+            assert reference() is provider
+            task.cancel()
+            with pytest.raises(asyncio.CancelledError):
+                await task
+        else:
+            response: Final = await call_native_aocr(
+                ocr_server,
+                model="azure_ai/mistral-ocr-latest",
+                api_key=None,
+                azure_ad_token_provider=provider,
+            )
+            assert response.pages[0].markdown == "native OCR response"
+        return reference
+
+    reference: Final = await invoke()
+    await drain_logging()
+    await asyncio.sleep(0)
+    gc.collect()
+    assert reference() is None
diff --git a/tests/test_litellm_rust/ocr/test_dispatch.py b/tests/test_litellm_rust/ocr/test_dispatch.py
new file mode 100644
index 00000000000..a6c76bc5d0e
--- /dev/null
+++ b/tests/test_litellm_rust/ocr/test_dispatch.py
@@ -0,0 +1,44 @@
+from typing import Final
+from unittest.mock import Mock
+
+import pytest
+
+import litellm
+from litellm.llms.base_llm.ocr.transformation import OCRResponse
+from litellm.ocr import main as ocr_main
+from tests.test_litellm_rust.support.recording_server import RecordingServer, ResponseSpec
+from tests.test_litellm_rust.support.requests import OCR_DOCUMENT, OCR_MODEL, OCR_RESPONSE
+
+pytestmark = pytest.mark.requires_rust_extension
+
+
+@pytest.fixture
+def ocr_server(recording_server: RecordingServer) -> RecordingServer:
+    recording_server.default_response = ResponseSpec(body=OCR_RESPONSE)
+    return recording_server
+
+
+@pytest.mark.parametrize("rust_enabled", [True, False], ids=["enabled", "disabled"])
+def test_public_ocr_dispatches_according_to_rust_setting(
+    ocr_server: RecordingServer,
+    monkeypatch: pytest.MonkeyPatch,
+    rust_enabled: bool,
+) -> None:
+    rust_call: Final = Mock(wraps=ocr_main.rust_ocr_bridge.ocr)
+    python_call: Final = Mock(wraps=ocr_main.base_llm_http_handler.ocr)
+    monkeypatch.setattr(ocr_main.rust_ocr_bridge, "ocr", rust_call)
+    monkeypatch.setattr(ocr_main.base_llm_http_handler, "ocr", python_call)
+    litellm.rust(rust_enabled)
+
+    response: Final = litellm.ocr(
+        model=OCR_MODEL,
+        document=OCR_DOCUMENT,
+        api_key="test-key",
+        api_base=ocr_server.base_url,
+    )
+
+    assert isinstance(response, OCRResponse)
+    assert response.pages[0].markdown == "native OCR response"
+    assert rust_call.call_count == int(rust_enabled)
+    assert python_call.call_count == int(not rust_enabled)
+    assert len(ocr_server.requests) == 1
diff --git a/tests/test_litellm_rust/ocr/test_guardrails.py b/tests/test_litellm_rust/ocr/test_guardrails.py
new file mode 100644
index 00000000000..f6fc1c7cb8d
--- /dev/null
+++ b/tests/test_litellm_rust/ocr/test_guardrails.py
@@ -0,0 +1,74 @@
+from typing import Final
+
+import pytest
+from fastapi import HTTPException
+
+import litellm
+from litellm.integrations.custom_guardrail import CustomGuardrail
+from litellm.proxy.guardrails.guardrail_hooks.litellm_content_filter.content_filter import ContentFilterGuardrail
+from litellm.types.guardrails import BlockedWord, ContentFilterAction, GuardrailEventHooks
+from litellm.types.utils import CallTypes
+from tests.test_litellm_rust.support.callback_recorder import RecordingLogger
+from tests.test_litellm_rust.support.recording_server import RecordingServer, ResponseSpec
+from tests.test_litellm_rust.support.requests import OCR_RESPONSE, call_native_aocr
+
+pytestmark = pytest.mark.requires_rust_extension
+
+
+@pytest.fixture
+def ocr_server(recording_server: RecordingServer) -> RecordingServer:
+    recording_server.default_response = ResponseSpec(body=OCR_RESPONSE)
+    return recording_server
+
+
+class ReplaceOCRMarkdown(CustomGuardrail):
+    def __init__(self) -> None:
+        super().__init__(
+            guardrail_name="replace-ocr-markdown", event_hook=GuardrailEventHooks.post_call, default_on=True
+        )
+        self.call_types: list[CallTypes] = []
+
+    async def async_post_call_success_deployment_hook(self, request_data, response, call_type):
+        self.call_types.append(call_type)
+        reviewed_page: Final = response.pages[0].model_copy(update={"markdown": "Reviewed OCR"})
+        return response.model_copy(update={"pages": [reviewed_page]})
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_post_call_content_filter_blocks_matching_markdown(
+    ocr_server: RecordingServer,
+) -> None:
+    guardrail: Final = ContentFilterGuardrail(
+        guardrail_name="block-native-ocr-markdown",
+        event_hook=GuardrailEventHooks.post_call,
+        blocked_words=[BlockedWord(keyword="native OCR response", action=ContentFilterAction.BLOCK)],
+    )
+    litellm.callbacks.append(guardrail)
+
+    with pytest.raises(HTTPException, match="Content blocked") as blocked:
+        await call_native_aocr(ocr_server, guardrails=[guardrail.guardrail_name])
+
+    assert blocked.value.status_code == 400
+    assert len(ocr_server.requests) == 1
+
+
+@pytest.mark.asyncio
+async def test_native_aocr_post_call_replacement_reaches_caller_and_success_callback(
+    ocr_server: RecordingServer,
+) -> None:
+    guardrail: Final = ReplaceOCRMarkdown()
+    recorder: Final = RecordingLogger()
+    litellm.callbacks.append(guardrail)
+
+    response: Final = await call_native_aocr(
+        ocr_server,
+        callbacks=[recorder],
+        guardrails=[guardrail.guardrail_name],
+    )
+    success_events: Final = await recorder.wait_for_async("async_log_success_event")
+
+    assert guardrail.call_types == [CallTypes.aocr]
+    assert response.pages[0].markdown == "Reviewed OCR"
+    assert len(success_events) == 1
+    assert success_events[0].response.pages[0].markdown == "Reviewed OCR"
+    assert "guardrails" not in ocr_server.requests[0].body
diff --git a/tests/test_litellm_rust/ocr/test_requests.py b/tests/test_litellm_rust/ocr/test_requests.py
new file mode 100644
index 00000000000..d241fe08fc8
--- /dev/null
+++ b/tests/test_litellm_rust/ocr/test_requests.py
@@ -0,0 +1,434 @@
+from typing import Final
+
+import pytest
+
+import litellm
+from litellm.llms.base_llm.ocr.transformation import OCRResponse
+from tests.test_litellm_rust.support.callback_recorder import RecordingLogger
+from tests.test_litellm_rust.support.requests import (
+    OCR_DOCUMENT,
+    OCR_RESPONSE,
+    call_native_aocr,
+    call_native_ocr,
+)
+from tests.test_litellm_rust.support.recording_server import RecordingServer, ResponseSpec
+
+pytestmark = pytest.mark.requires_rust_extension
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+async def test_native_azure_ocr_uses_token_provider_result_as_bearer_token(
+    ocr_server: RecordingServer, isolated_azure_auth: None, asynchronous: bool
+) -> None:
+    calls: Final = []
+
+    def token_provider() -> str:
+        calls.append("token")
+        return "callback-token"
+
+    arguments: Final = {
+        "model": "azure_ai/mistral-ocr-latest",
+        "api_key": None,
+        "azure_ad_token_provider": token_provider,
+    }
+    response: Final = (
+        await call_native_aocr(ocr_server, **arguments) if asynchronous else call_native_ocr(ocr_server, **arguments)
+    )
+
+    assert calls == ["token"]
+    assert response.pages[0].markdown == "native OCR response"
+    assert_native_request(ocr_server)
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer callback-token"
+
+
+@pytest.fixture
+def ocr_server(recording_server: RecordingServer) -> RecordingServer:
+    recording_server.default_response = ResponseSpec(body=OCR_RESPONSE)
+    return recording_server
+
+
+def assert_native_request(server: RecordingServer) -> None:
+    assert len(server.requests) == 1
+    assert not server.requests[0].headers.get("user-agent", "").startswith("python-httpx")
+
+
+def test_native_ocr_sends_model_and_document_to_mistral_ocr_path(ocr_server: RecordingServer) -> None:
+    response: Final = call_native_ocr(ocr_server)
+
+    assert response.pages[0].markdown == "native OCR response"
+    assert_native_request(ocr_server)
+    assert ocr_server.requests[0].path == "/v1/ocr"
+    assert ocr_server.requests[0].body == {"model": "mistral-ocr-latest", "document": OCR_DOCUMENT}
+
+
+def test_native_ocr_prepares_file_document_like_python(ocr_server: RecordingServer) -> None:
+    response: Final = call_native_ocr(
+        ocr_server,
+        document={"type": "file", "file": b"%PDF-1.4", "mime_type": "application/pdf"},
+    )
+
+    assert response.pages[0].markdown == "native OCR response"
+    assert_native_request(ocr_server)
+    assert ocr_server.requests[0].body == {
+        "model": "mistral-ocr-latest",
+        "document": {
+            "type": "document_url",
+            "document_url": "data:application/pdf;base64,JVBERi0xLjQ=",
+        },
+    }
+
+
+def test_native_ocr_sends_pages_and_image_options(ocr_server: RecordingServer) -> None:
+    call_native_ocr(ocr_server, pages=[0, 2], include_image_base64=True)
+
+    assert ocr_server.requests[0].body["pages"] == [0, 2]
+    assert ocr_server.requests[0].body["include_image_base64"] is True
+
+
+def test_native_ocr_merges_custom_headers_with_authorization(ocr_server: RecordingServer) -> None:
+    call_native_ocr(ocr_server, extra_headers={"x-trace-id": "trace-1"})
+
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer test-key"
+    assert ocr_server.requests[0].headers["x-trace-id"] == "trace-1"
+
+
+def test_native_mistral_ocr_uses_environment_api_key_when_argument_is_missing(
+    ocr_server: RecordingServer, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setenv("MISTRAL_API_KEY", "environment-key")
+
+    call_native_ocr(ocr_server, api_key=None)
+
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer environment-key"
+
+
+def test_native_mistral_ocr_prefers_explicit_api_key_over_environment(
+    ocr_server: RecordingServer, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setenv("MISTRAL_API_KEY", "environment-key")
+
+    call_native_ocr(ocr_server)
+
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer test-key"
+
+
+def test_native_azure_ocr_uses_environment_endpoint_and_api_key(
+    ocr_server: RecordingServer, monkeypatch: pytest.MonkeyPatch
+) -> None:
+    monkeypatch.setenv("AZURE_AI_API_KEY", "azure-key")
+    monkeypatch.setenv("AZURE_AI_API_BASE", ocr_server.base_url)
+
+    call_native_ocr(ocr_server, model="azure_ai/pixtral-12b-2409", api_key=None, api_base=None)
+
+    assert_native_request(ocr_server)
+    assert ocr_server.requests[0].path == "/providers/mistral/azure/ocr"
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer azure-key"
+
+
+def test_native_vertex_ocr_builds_path_from_project_and_location(ocr_server: RecordingServer) -> None:
+    call_native_ocr(
+        ocr_server,
+        model="vertex_ai/mistral-ocr-2505",
+        api_key="vertex-token",
+        vertex_project="project-1",
+        vertex_location="us-central1",
+    )
+
+    assert_native_request(ocr_server)
+    assert ocr_server.requests[0].path == (
+        "/v1/projects/project-1/locations/us-central1/publishers/mistralai/models/mistral-ocr-2505:rawPredict"
+    )
+
+
+def test_native_ocr_normalizes_provider_response_model_and_usage(ocr_server: RecordingServer) -> None:
+    response: Final = call_native_ocr(ocr_server)
+
+    assert isinstance(response, OCRResponse)
+    assert response.model == "mistral-ocr-latest"
+    assert response.usage_info.pages_processed == 1
+
+
+def test_native_ocr_maps_provider_400_without_exposing_response_body(ocr_server: RecordingServer) -> None:
+    ocr_server.enqueue(ResponseSpec(body={"message": "invalid OCR request"}, status=400))
+
+    with pytest.raises(litellm.BadRequestError) as caught:
+        call_native_ocr(ocr_server)
+
+    assert caught.value.status_code == 400
+    assert caught.value.model == "mistral-ocr-latest"
+    assert caught.value.llm_provider == "mistral"
+    assert "invalid OCR request" not in str(caught.value)
+
+
+def test_native_ocr_raises_transport_error_when_request_exceeds_timeout(ocr_server: RecordingServer) -> None:
+    ocr_server.enqueue(ResponseSpec(body=OCR_RESPONSE, delay=0.2))
+
+    with pytest.raises(RuntimeError, match="OCR transport failed"):
+        call_native_ocr(ocr_server, timeout=0.01)
+
+    assert len(ocr_server.requests) == 1
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+@pytest.mark.parametrize(
+    "credentials, expected_token, expected_calls",
+    [
+        ({"api_key": "resource-key"}, "resource-key", 0),
+        ({"azure_ad_token": "static-token"}, "callback-1", 1),
+        ({"extra_headers": {"Authorization": "Bearer override"}}, "override", 1),
+    ],
+    ids=["api-key-skips-provider", "provider-overrides-static-token", "header-overrides-provider"],
+)
+async def test_native_azure_ocr_applies_python_credential_precedence(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    asynchronous: bool,
+    credentials: dict[str, object],
+    expected_token: str,
+    expected_calls: int,
+) -> None:
+    calls: Final = []
+
+    def token_provider() -> str:
+        calls.append("token")
+        return f"callback-{len(calls)}"
+
+    arguments: Final = {
+        "model": "azure_ai/mistral-ocr-latest",
+        "api_key": None,
+        "azure_ad_token_provider": token_provider,
+        **credentials,
+    }
+    response: Final = (
+        await call_native_aocr(ocr_server, **arguments) if asynchronous else call_native_ocr(ocr_server, **arguments)
+    )
+    assert response.pages[0].markdown == "native OCR response"
+    assert len(calls) == expected_calls
+    assert len(ocr_server.requests) == 1
+    assert ocr_server.requests[0].headers["authorization"] == f"Bearer {expected_token}"
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+async def test_native_azure_ocr_calls_token_provider_for_each_request(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    asynchronous: bool,
+) -> None:
+    calls: Final = []
+    ocr_server.expected_requests = 2
+
+    def token_provider() -> str:
+        calls.append("token")
+        return f"callback-{len(calls)}"
+
+    for _ in range(2):
+        arguments: Final = {
+            "model": "azure_ai/mistral-ocr-latest",
+            "api_key": None,
+            "azure_ad_token_provider": token_provider,
+        }
+        response: Final = (
+            await call_native_aocr(ocr_server, **arguments)
+            if asynchronous
+            else call_native_ocr(ocr_server, **arguments)
+        )
+        assert response.pages[0].markdown == "native OCR response"
+    assert len(calls) == 2
+    assert [request.headers["authorization"] for request in ocr_server.requests] == [
+        "Bearer callback-1",
+        "Bearer callback-2",
+    ]
+
+
+class TokenAbort(BaseException):
+    pass
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("asynchronous", [False, True], ids=["sync", "async"])
+@pytest.mark.parametrize(
+    "failure",
+    ["non_string", "type_error", "ordinary", "abort"],
+    ids=["non-string-result", "type-error", "value-error", "base-exception"],
+)
+async def test_native_azure_ocr_token_provider_failure_prevents_pre_call_callback_and_request(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    asynchronous: bool,
+    failure: str,
+) -> None:
+    ocr_server.expected_requests = 0
+    calls: Final = []
+    recorder: Final = RecordingLogger()
+    original: Final = {
+        "type_error": TypeError("token type"),
+        "ordinary": ValueError("token unavailable"),
+        "abort": TokenAbort("abort"),
+    }
+
+    def token_provider() -> object:
+        calls.append("token")
+        if failure == "non_string":
+            return 123
+        raise original[failure]
+
+    arguments: Final = {
+        "model": "azure_ai/mistral-ocr-latest",
+        "api_key": None,
+        "azure_ad_token_provider": token_provider,
+        "callbacks": [recorder],
+    }
+    expected: Final = TokenAbort if failure == "abort" else litellm.APIConnectionError
+    with pytest.raises(expected) as caught:
+        await call_native_aocr(ocr_server, **arguments) if asynchronous else call_native_ocr(ocr_server, **arguments)
+    assert calls == ["token"]
+    assert ocr_server.requests == []
+    assert "log_pre_api_call" not in recorder.names
+    if failure == "ordinary":
+        assert "Failed to get Azure AD token: token unavailable" in str(caught.value)
+        assert isinstance(caught.value.__context__, RuntimeError)
+        assert caught.value.__context__.__cause__ is original[failure]
+    elif failure == "abort":
+        assert caught.value is original[failure]
+    elif failure == "type_error":
+        assert caught.value.__context__ is original[failure]
+    else:
+        assert isinstance(caught.value.__context__, TypeError)
+
+
+@pytest.mark.parametrize(
+    "configuration",
+    [
+        {"azure_ad_token": "oidc/assertion", "client_id": "client", "tenant_id": "tenant"},
+        {"model": "azure_ai/doc-intelligence/prebuilt-read"},
+    ],
+    ids=["oidc-assertion", "document-intelligence-model"],
+)
+def test_native_azure_ocr_rejects_unsupported_configuration_before_token_or_callbacks(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+    configuration: dict[str, object],
+) -> None:
+    ocr_server.expected_requests = 0
+    calls: Final = []
+    recorder: Final = RecordingLogger()
+
+    def provider() -> str:
+        calls.append("token")
+        return "unused"
+
+    arguments: Final = {
+        "model": "azure_ai/mistral-ocr-latest",
+        "api_key": None,
+        "azure_ad_token_provider": provider,
+        "callbacks": [recorder],
+        **configuration,
+    }
+    with pytest.raises(NotImplementedError):
+        call_native_ocr(ocr_server, **arguments)
+    assert calls == []
+    assert recorder.events == ()
+    assert ocr_server.requests == []
+
+
+@pytest.mark.asyncio
+async def test_native_azure_ocr_validates_endpoint_before_calling_token_provider(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+) -> None:
+    ocr_server.expected_requests = 0
+    calls: Final = []
+
+    def provider() -> str:
+        calls.append("token")
+        return "unused"
+
+    with pytest.raises(litellm.APIConnectionError, match="Missing Azure AI API Base"):
+        await call_native_aocr(
+            ocr_server,
+            model="azure_ai/mistral-ocr-latest",
+            api_key=None,
+            api_base=None,
+            azure_ad_token_provider=provider,
+        )
+    assert calls == []
+    assert ocr_server.requests == []
+
+
+@pytest.mark.asyncio
+async def test_native_azure_ocr_does_not_fall_back_to_static_token_after_empty_provider_result(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+) -> None:
+    ocr_server.expected_requests = 0
+
+    def provider() -> str:
+        return ""
+
+    with pytest.raises(litellm.APIConnectionError, match="Missing Azure AI credentials"):
+        await call_native_aocr(
+            ocr_server,
+            model="azure_ai/mistral-ocr-latest",
+            api_key=None,
+            azure_ad_token="static-token",
+            azure_ad_token_provider=provider,
+        )
+    assert ocr_server.requests == []
+
+
+@pytest.mark.asyncio
+async def test_native_azure_ocr_ignores_falsey_token_provider_and_uses_static_token(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+) -> None:
+    calls: Final = []
+
+    class Provider:
+        def __bool__(self) -> bool:
+            return False
+
+        def __call__(self) -> str:
+            calls.append("token")
+            return "unused"
+
+    response: Final = await call_native_aocr(
+        ocr_server,
+        model="azure_ai/mistral-ocr-latest",
+        api_key=None,
+        azure_ad_token="static-token",
+        azure_ad_token_provider=Provider(),
+    )
+    assert response.pages[0].markdown == "native OCR response"
+    assert calls == []
+    assert ocr_server.requests[0].headers["authorization"] == "Bearer static-token"
+
+
+@pytest.mark.asyncio
+async def test_native_azure_ocr_rejects_coroutine_returned_by_sync_token_provider(
+    ocr_server: RecordingServer,
+    isolated_azure_auth: None,
+) -> None:
+    ocr_server.expected_requests = 0
+    calls: Final = []
+
+    async def acquire() -> str:
+        calls.append("awaited")
+        return "unused"
+
+    coroutine: Final = acquire()
+
+    def provider() -> object:
+        return coroutine
+
+    try:
+        with pytest.raises(litellm.APIConnectionError, match="Azure AD token must be a string"):
+            await call_native_aocr(
+                ocr_server, model="azure_ai/mistral-ocr-latest", api_key=None, azure_ad_token_provider=provider
+            )
+    finally:
+        coroutine.close()
+    assert calls == []
+    assert ocr_server.requests == []
diff --git a/tests/test_litellm_rust/support/__init__.py b/tests/test_litellm_rust/support/__init__.py
new file mode 100644
index 00000000000..8b137891791
--- /dev/null
+++ b/tests/test_litellm_rust/support/__init__.py
@@ -0,0 +1 @@
+
diff --git a/tests/test_litellm_rust/support/callback_recorder.py b/tests/test_litellm_rust/support/callback_recorder.py
new file mode 100644
index 00000000000..6de011b1414
--- /dev/null
+++ b/tests/test_litellm_rust/support/callback_recorder.py
@@ -0,0 +1,101 @@
+import asyncio
+import copy
+import threading
+import time
+from dataclasses import dataclass
+from typing import Final
+
+from litellm.integrations.custom_logger import CustomLogger
+from litellm.litellm_core_utils.logging_worker import GLOBAL_LOGGING_WORKER, LoggingWorker
+
+
+async def drain_logging(worker: LoggingWorker = GLOBAL_LOGGING_WORKER) -> None:
+    await asyncio.sleep(0)
+    worker.start()
+    await asyncio.wait_for(worker.flush(), timeout=10)
+
+
+@dataclass(frozen=True, slots=True)
+class HookEvent:
+    name: str
+    call_type: str | None
+    thread: threading.Thread
+    loop: asyncio.AbstractEventLoop | None
+    kwargs: object
+    response: object
+
+
+class RecordingLogger(CustomLogger):
+    def __init__(self) -> None:
+        super().__init__()
+        self._events: list[HookEvent] = []
+        self._condition = threading.Condition()
+
+    @property
+    def events(self) -> tuple[HookEvent, ...]:
+        with self._condition:
+            return tuple(self._events)
+
+    @property
+    def names(self) -> tuple[str, ...]:
+        return tuple(event.name for event in self.events)
+
+    def _record(self, name: str, kwargs: object = None, response: object = None) -> None:
+        details: Final = kwargs if isinstance(kwargs, dict) else {}
+        try:
+            snapshot: Final = copy.deepcopy(details)
+        except Exception:
+            snapshot = dict(details)
+        if "exception" in details:
+            snapshot["exception"] = details["exception"]
+        try:
+            loop: Final = asyncio.get_running_loop()
+        except RuntimeError:
+            loop = None
+        event: Final = HookEvent(
+            name=name,
+            call_type=details.get("call_type"),
+            thread=threading.current_thread(),
+            loop=loop,
+            kwargs=snapshot,
+            response=response,
+        )
+        with self._condition:
+            self._events.append(event)
+            self._condition.notify_all()
+
+    def wait_for(self, name: str, count: int = 1, timeout: float = 10) -> tuple[HookEvent, ...]:
+        deadline: Final = time.monotonic() + timeout
+        with self._condition:
+            while sum(event.name == name for event in self._events) < count:
+                remaining: Final = deadline - time.monotonic()
+                if remaining <= 0:
+                    raise TimeoutError(f"Timed out waiting for {count} {name} events; saw {self.names}")
+                self._condition.wait(remaining)
+            return tuple(event for event in self._events if event.name == name)
+
+    async def wait_for_async(self, name: str, count: int = 1, timeout: float = 10) -> tuple[HookEvent, ...]:
+        await asyncio.wait_for(asyncio.to_thread(self.wait_for, name, count, timeout), timeout=timeout + 1)
+        from litellm.litellm_core_utils.logging_worker import GLOBAL_LOGGING_WORKER
+
+        await asyncio.wait_for(GLOBAL_LOGGING_WORKER.flush(), timeout=timeout)
+        return tuple(event for event in self.events if event.name == name)
+
+    def log_pre_api_call(self, model, _messages, kwargs):
+        self._record("log_pre_api_call", kwargs)
+
+    def log_success_event(self, kwargs, response_obj, start_time, end_time):
+        self._record("log_success_event", kwargs, response_obj)
+
+    async def async_log_success_event(self, kwargs, response_obj, start_time, end_time):
+        self._record("async_log_success_event", kwargs, response_obj)
+
+    def log_failure_event(self, kwargs, response_obj, start_time, end_time):
+        self._record("log_failure_event", kwargs, response_obj)
+
+    async def async_log_failure_event(self, kwargs, response_obj, start_time, end_time):
+        self._record("async_log_failure_event", kwargs, response_obj)
+
+    def logging_hook(self, kwargs, result, call_type):
+        self._record("logging_hook", kwargs, result)
+        return kwargs, result
diff --git a/tests/test_litellm_rust/support/recording_server.py b/tests/test_litellm_rust/support/recording_server.py
new file mode 100644
index 00000000000..5a9b9497c6e
--- /dev/null
+++ b/tests/test_litellm_rust/support/recording_server.py
@@ -0,0 +1,108 @@
+import asyncio
+import copy
+import json
+import threading
+import time
+from collections.abc import Iterator
+from contextlib import contextmanager
+from dataclasses import dataclass, field
+from http.server import BaseHTTPRequestHandler, ThreadingHTTPServer
+from typing import Final
+
+
+@dataclass
+class RecordedRequest:
+    method: str
+    path: str
+    headers: dict[str, str]
+    raw_body: bytes
+    body: object | None
+
+
+@dataclass
+class ResponseSpec:
+    body: object
+    status: int = 200
+    headers: dict[str, str] = field(default_factory=dict)
+    delay: float = 0
+
+
+@dataclass
+class RecordingServer:
+    server: ThreadingHTTPServer
+    requests: list[RecordedRequest]
+    responses: list[ResponseSpec]
+    default_response: ResponseSpec
+    expected_requests: int | None = 1
+
+    @property
+    def base_url(self) -> str:
+        host, port = self.server.server_address
+        return f"http://{host}:{port}"
+
+    def enqueue(self, response: ResponseSpec) -> None:
+        self.responses.append(response)
+
+    async def wait_for_requests(self, count: int) -> None:
+        async with asyncio.timeout(2):
+            while len(self.requests) < count:
+                await asyncio.sleep(0.01)
+
+
+@contextmanager
+def recording_service() -> Iterator[RecordingServer]:
+    requests: list[RecordedRequest] = []
+    responses: list[ResponseSpec] = []
+
+    class Handler(BaseHTTPRequestHandler):
+        def _handle(self) -> None:
+            content_length: Final = int(self.headers.get("Content-Length", "0"))
+            raw_body: Final = self.rfile.read(content_length) if content_length else b""
+            body: Final = json.loads(raw_body) if raw_body else None
+            requests.append(
+                RecordedRequest(
+                    method=self.command,
+                    path=self.path,
+                    headers={name.lower(): value for name, value in self.headers.items()},
+                    raw_body=raw_body,
+                    body=body,
+                )
+            )
+            response: Final = responses.pop(0) if responses else copy.deepcopy(recording_server.default_response)
+            if response.delay:
+                time.sleep(response.delay)
+            payload: Final = json.dumps(response.body).encode()
+            self.send_response(response.status)
+            self.send_header("Content-Type", "application/json")
+            self.send_header("Content-Length", str(len(payload)))
+            for name, value in response.headers.items():
+                self.send_header(name, value)
+            self.end_headers()
+            try:
+                self.wfile.write(payload)
+            except (BrokenPipeError, ConnectionResetError):
+                pass
+
+        do_POST = _handle
+
+        def log_message(self, format: str, *args: object) -> None:
+            pass
+
+    server: Final = ThreadingHTTPServer(("127.0.0.1", 0), Handler)
+    thread: Final = threading.Thread(target=server.serve_forever, kwargs={"poll_interval": 0.01}, daemon=True)
+    thread.start()
+    try:
+        recording_server = RecordingServer(
+            server=server,
+            requests=requests,
+            responses=responses,
+            default_response=ResponseSpec(body={}),
+        )
+        yield recording_server
+    finally:
+        server.shutdown()
+        server.server_close()
+        thread.join()
+        if recording_server.expected_requests is not None:
+            assert len(recording_server.requests) == recording_server.expected_requests
+        assert recording_server.responses == []
diff --git a/tests/test_litellm_rust/support/requests.py b/tests/test_litellm_rust/support/requests.py
new file mode 100644
index 00000000000..d681d752ffd
--- /dev/null
+++ b/tests/test_litellm_rust/support/requests.py
@@ -0,0 +1,59 @@
+from typing import Final
+
+import litellm
+from litellm.llms.base_llm.ocr.transformation import OCRResponse
+from litellm.rust_bridge import ocr as native_ocr
+from tests.test_litellm_rust.support.recording_server import RecordingServer
+
+OCR_DOCUMENT: Final = {"type": "document_url", "document_url": "data:application/pdf;base64,YWJj"}
+OCR_MODEL: Final = "mistral/mistral-ocr-latest"
+OCR_RESPONSE: Final = {
+    "pages": [{"index": 0, "markdown": "native OCR response", "images": [], "dimensions": None}],
+    "model": "mistral-ocr-latest",
+    "usage_info": {"pages_processed": 1, "doc_size_bytes": 3},
+}
+
+
+def ocr_arguments(server: RecordingServer, **kwargs: object) -> dict[str, object]:
+    return {
+        "model": OCR_MODEL,
+        "document": dict(OCR_DOCUMENT),
+        "api_key": "test-key",
+        "api_base": server.base_url,
+        **kwargs,
+    }
+
+
+def call_ocr(server: RecordingServer, **kwargs: object) -> OCRResponse:
+    response: Final = litellm.ocr(**ocr_arguments(server, **kwargs))
+    if not isinstance(response, OCRResponse):
+        raise TypeError(f"Expected OCRResponse, got {type(response).__name__}")
+    return response
+
+
+async def call_aocr(server: RecordingServer, **kwargs: object) -> OCRResponse:
+    return await litellm.aocr(**ocr_arguments(server, **kwargs))
+
+
+def call_native_ocr(server: RecordingServer, **kwargs: object) -> OCRResponse:
+    return native_ocr.ocr(ocr_arguments(server, **kwargs))
+
+
+async def call_native_aocr(server: RecordingServer, **kwargs: object) -> OCRResponse:
+    return await native_ocr.aocr(ocr_arguments(server, **kwargs))
+
+
+def request_body(kwargs: dict[str, object]) -> dict[str, object]:
+    additional_args = kwargs["additional_args"]
+    assert isinstance(additional_args, dict)
+    body = additional_args["complete_input_dict"]
+    assert isinstance(body, dict)
+    return body
+
+
+def request_headers(kwargs: dict[str, object]) -> dict[str, object]:
+    additional_args = kwargs["additional_args"]
+    assert isinstance(additional_args, dict)
+    headers = additional_args["headers"]
+    assert isinstance(headers, dict)
+    return headers
diff --git a/tests/test_litellm_rust/test_ocr.py b/tests/test_litellm_rust/test_ocr.py
index d5b1fce1139..1293de9ee0e 100644
--- a/tests/test_litellm_rust/test_ocr.py
+++ b/tests/test_litellm_rust/test_ocr.py
@@ -1,31 +1,34 @@
 import json
 import threading
+from collections.abc import Generator
+from dataclasses import dataclass
 from http.server import BaseHTTPRequestHandler, ThreadingHTTPServer
+from typing import Final
 
 import pytest
 
-import litellm
+from litellm.rust_bridge import ocr as rust_ocr_bridge
 
 pytestmark = pytest.mark.requires_rust_extension
 
 
+@dataclass(frozen=True, slots=True)
+class RecordedOCRRequest:
+    body: object
+
+
 @pytest.fixture
-def ocr_server():
-    requests = []
+def ocr_server() -> Generator[tuple[ThreadingHTTPServer, list[RecordedOCRRequest]]]:
+    requests: Final[list[RecordedOCRRequest]] = []
 
     class Handler(BaseHTTPRequestHandler):
-        def do_POST(self):
+        def do_POST(self) -> None:
             requests.append(
-                {
-                    "headers": {name.lower(): value for name, value in self.headers.items()},
-                    "body": json.loads(self.rfile.read(int(self.headers["Content-Length"]))),
-                }
+                RecordedOCRRequest(
+                    body=json.loads(self.rfile.read(int(self.headers["Content-Length"]))),
+                )
             )
-            if self.headers.get("User-Agent", "").startswith("python-httpx"):
-                self.send_response(418)
-                self.end_headers()
-                return
-            response = json.dumps(
+            response: Final = json.dumps(
                 {
                     "pages": [{"index": 0, "markdown": "native OCR response", "images": [], "dimensions": None}],
                     "model": "mistral-ocr-latest",
@@ -38,11 +41,11 @@ def ocr_server():
             self.end_headers()
             self.wfile.write(response)
 
-        def log_message(self, format, *args):
+        def log_message(self, format: str, *args: object) -> None:
             pass
 
-    server = ThreadingHTTPServer(("127.0.0.1", 0), Handler)
-    thread = threading.Thread(target=lambda: server.serve_forever(poll_interval=0.01), daemon=True)
+    server: Final = ThreadingHTTPServer(("127.0.0.1", 0), Handler)
+    thread: Final = threading.Thread(target=lambda: server.serve_forever(poll_interval=0.01), daemon=True)
     thread.start()
     try:
         yield server, requests
@@ -52,21 +55,29 @@ def ocr_server():
         thread.join()
 
 
-def test_ocr_with_rust_extension(ocr_server):
+def test_native_ocr_with_compiled_rust_extension(
+    ocr_server: tuple[ThreadingHTTPServer, list[RecordedOCRRequest]],
+) -> None:
     server, requests = ocr_server
-    host, port = server.server_address
+    address: Final = server.server_address
+    host: Final = str(address[0])
+    port: Final = int(address[1])
 
-    response = litellm.ocr(
-        model="mistral/mistral-ocr-latest",
+    response: Final = rust_ocr_bridge.ocr(
+        model="mistral-ocr-latest",
         document={"type": "document_url", "document_url": "data:application/pdf;base64,YWJj"},
         api_key="test-key",
         api_base=f"http://{host}:{port}",
+        custom_llm_provider="mistral",
+        extra_headers=None,
+        optional_params={},
+        timeout=None,
     )
 
-    assert response.pages[0].markdown == "native OCR response"
+    assert response is not None
+    assert response["pages"][0]["markdown"] == "native OCR response"
     assert len(requests) == 1
-    assert not requests[0]["headers"].get("user-agent", "").startswith("python-httpx")
-    assert requests[0]["body"] == {
-            "model": "mistral-ocr-latest",
-            "document": {"type": "document_url", "document_url": "data:application/pdf;base64,YWJj"},
+    assert requests[0].body == {
+        "model": "mistral-ocr-latest",
+        "document": {"type": "document_url", "document_url": "data:application/pdf;base64,YWJj"},
     }
diff --git a/ui/litellm-dashboard/eslint-suppressions.json b/ui/litellm-dashboard/eslint-suppressions.json
index 76ac60a6453..e2a08a40bcb 100644
--- a/ui/litellm-dashboard/eslint-suppressions.json
+++ b/ui/litellm-dashboard/eslint-suppressions.json
@@ -2325,11 +2325,6 @@
       "count": 4
     }
   },
-  "src/components/view_logs/LogDetailsDrawer/LogDetailContent.tsx": {
-    "no-nested-ternary": {
-      "count": 3
-    }
-  },
   "src/components/view_logs/LogDetailsDrawer/LogDetailsDrawer.tsx": {
     "no-nested-ternary": {
       "count": 2
diff --git a/ui/litellm-dashboard/package-lock.json b/ui/litellm-dashboard/package-lock.json
index 44360e94392..1f459bc50ea 100644
--- a/ui/litellm-dashboard/package-lock.json
+++ b/ui/litellm-dashboard/package-lock.json
@@ -11402,9 +11402,9 @@
       }
     },
     "node_modules/smol-toml": {
-      "version": "1.6.1",
-      "resolved": "https://registry.npmjs.org/smol-toml/-/smol-toml-1.6.1.tgz",
-      "integrity": "sha512-dWUG8F5sIIARXih1DTaQAX4SsiTXhInKf1buxdY9DIg4ZYPZK5nGM1VRIYmEbDbsHt7USo99xSLFu5Q1IqTmsg==",
+      "version": "1.8.0",
+      "resolved": "https://registry.npmjs.org/smol-toml/-/smol-toml-1.8.0.tgz",
+      "integrity": "sha512-kCZr2V3ch9i00x8zXRhjUNVcjG9ijES5dDudkXvUVCT5QlJNQWElSJdZqyPemffHoLNUYwOcou0Fy+ojN0uHSQ==",
       "dev": true,
       "license": "BSD-3-Clause",
       "engines": {
diff --git a/ui/litellm-dashboard/public/assets/logos/pointfive.png b/ui/litellm-dashboard/public/assets/logos/pointfive.png
new file mode 100644
index 00000000000..4b7a6b8939e
Binary files /dev/null and b/ui/litellm-dashboard/public/assets/logos/pointfive.png differ
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/access-groups/_components/AccessGroupsDetailsPage.tsx b/ui/litellm-dashboard/src/app/(dashboard)/access-groups/_components/AccessGroupsDetailsPage.tsx
index 1eeebe4ebba..118a8655d5a 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/access-groups/_components/AccessGroupsDetailsPage.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/access-groups/_components/AccessGroupsDetailsPage.tsx
@@ -54,7 +54,7 @@ function ResourceBadge({
   fallback,
 }: {
   resource: AccessGroupResource;
-  href: string;
+  href?: string;
   fallback: (id: string) => string;
 }) {
   const badge = (
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalSection.test.tsx b/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalSection.test.tsx
index 64363da9933..1f73671caae 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalSection.test.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalSection.test.tsx
@@ -1,3 +1,4 @@
+import { QueryClient, QueryClientProvider } from "@tanstack/react-query";
 import { fireEvent, render, screen, within } from "@testing-library/react";
 import userEvent from "@testing-library/user-event";
 import React from "react";
@@ -14,7 +15,9 @@ vi.mock("./useShadowEval", () => ({
 }));
 
 const authorizedRoleMock = vi.fn(() => ({ accessToken: "token", isViewOnly: false }));
-vi.mock("@/app/(dashboard)/hooks/useAuthorized", () => ({ default: () => authorizedRoleMock() }));
+vi.mock("@/app/(dashboard)/hooks/useAuthorized", () => ({
+  default: () => ({ userId: "test-user-id", userRole: "Admin", ...authorizedRoleMock() }),
+}));
 
 vi.mock("@/app/(dashboard)/hooks/keys/useKeys", () => ({
   useInfiniteKeys: vi.fn(() => ({
@@ -68,27 +71,33 @@ vi.mock("@/app/(dashboard)/hooks/users/useUsers", () => ({
   })),
 }));
 
-vi.mock("@/app/(dashboard)/hooks/models/useModels", () => ({
+vi.mock("@/app/(dashboard)/hooks/models/useModels", async (importOriginal) => ({
+  ...(await importOriginal<typeof import("@/app/(dashboard)/hooks/models/useModels")>()),
   useAutoRouters: vi.fn(() => ({
     data: [
       { model_name: "claude-auto", litellm_params: { model: "auto_router/claude-auto" } },
       { model_name: "gpt-auto", litellm_params: { model: "auto_router/gpt-auto" } },
     ],
   })),
-  usePlainModelGroups: vi.fn(() => new Set(["prod-claude"])),
+  usePlainModelGroups: vi.fn(() => new Set(["prod-claude", "prod-judge"])),
+  usePlainChatModelGroups: vi.fn(() => new Set(["prod-claude", "prod-judge"])),
+  usePlainChatModelDeployments: vi.fn(() => [
+    {
+      model_name: "prod-judge",
+      litellm_params: { model: "anthropic/claude-sonnet-5" },
+      model_info: { mode: "chat" },
+    },
+  ]),
 }));
 
-vi.mock("@/app/(dashboard)/hooks/models/useModelCostMap", () => ({
-  useModelCostMap: vi.fn(() => ({
-    data: {
-      "claude-sonnet-5": { litellm_provider: "anthropic", mode: "chat" },
-      "gpt-4o": { litellm_provider: "openai", mode: "chat" },
-      "gemini/gemini-2.5-pro": { litellm_provider: "gemini", mode: "chat" },
-      "text-embedding-3-large": { litellm_provider: "openai", mode: "embedding" },
-    },
-  })),
+vi.mock("@/components/networking", async (importOriginal) => ({
+  ...(await importOriginal<typeof import("@/components/networking")>()),
+  modelInfoCall: vi.fn(),
 }));
 
+import { usePlainChatModelGroups, usePlainModelGroups } from "@/app/(dashboard)/hooks/models/useModels";
+import { modelInfoCall } from "@/components/networking";
+
 import ShadowEvalSection, { shadowedTargetLabel } from "./ShadowEvalSection";
 import {
   useShadowEvalJob,
@@ -107,7 +116,7 @@ const job = (overrides: Partial<ShadowEvalJob> = {}): ShadowEvalJob => ({
   models: [],
   direction: "forward",
   baseline_model: null,
-  judge_model: "anthropic/claude-sonnet-5",
+  judge_model: "prod-judge",
   shadow_percentage: 10,
   targets: [
     {
@@ -249,6 +258,85 @@ describe("ShadowEvalSection", () => {
     if (defaultKeysImpl) vi.mocked(useInfiniteKeys).mockImplementation(defaultKeysImpl);
   });
 
+  it("labels only configured judge recommendations", async () => {
+    const user = userEvent.setup();
+    mockHooks({});
+    render(<ShadowEvalSection />);
+
+    await user.click(screen.getByPlaceholderText("Select a judge model"));
+    expect(screen.getByRole("option", { name: /prod-judge.*Recommended/ })).toBeInTheDocument();
+    expect(screen.queryByRole("option", { name: /openai\/gpt-4o/ })).not.toBeInTheDocument();
+
+    await user.keyboard("{Escape}");
+    await chooseSelectOption(
+      user,
+      screen.getByText("Adoption check: key's traffic vs the router"),
+      "Regression check: router's picks vs a baseline",
+    );
+    await user.click(screen.getByPlaceholderText("Select a baseline model"));
+    expect(screen.getByRole("option", { name: "prod-judge", exact: true })).toBeInTheDocument();
+    expect(screen.queryByText("Recommended")).not.toBeInTheDocument();
+  });
+
+  it("keeps custom models selectable through the real model hooks without widening chat choices to traffic filters", async () => {
+    const hooks = await vi.importActual<typeof import("@/app/(dashboard)/hooks/models/useModels")>(
+      "@/app/(dashboard)/hooks/models/useModels",
+    );
+    const client = new QueryClient({ defaultOptions: { queries: { retry: false } } });
+    const deployments = [
+      { model_name: "custom-chat", litellm_params: { model: "openai/private-chat" } },
+      { model_name: "custom-judge", litellm_params: { model: "openai/private-judge" }, model_info: { mode: null } },
+      {
+        model_name: "embedding",
+        litellm_params: { model: "openai/private-embedding" },
+        model_info: { mode: "embedding" },
+      },
+      {
+        model_name: "responses-only",
+        litellm_params: { model: "openai/private-responses" },
+        model_info: { mode: "responses" },
+      },
+      { model_name: "auto-router", litellm_params: { model: "auto_router/complexity_router" } },
+    ];
+    vi.mocked(modelInfoCall).mockResolvedValue({ data: deployments, total_pages: 1 });
+    const user = userEvent.setup();
+    const { start } = mockHooks({});
+    await vi.mocked(usePlainModelGroups).withImplementation(hooks.usePlainModelGroups, async () => {
+      await vi.mocked(usePlainChatModelGroups).withImplementation(hooks.usePlainChatModelGroups, async () => {
+        render(
+          <QueryClientProvider client={client}>
+            <ShadowEvalSection />
+          </QueryClientProvider>,
+        );
+        await chooseSelectOption(user, screen.getByPlaceholderText("Every model the targets use"), "responses-only");
+        await chooseSelectOption(user, screen.getByPlaceholderText("Every model the targets use"), "custom-chat");
+        await chooseSelectOption(
+          user,
+          screen.getByText("Adoption check: key's traffic vs the router"),
+          "Regression check: router's picks vs a baseline",
+        );
+        await user.click(screen.getByPlaceholderText("Search keys by alias"));
+        await user.click(within(await screen.findByTestId("paginated-multi-select-list")).getByText("prod-alpha"));
+        await chooseSelectOption(user, screen.getByPlaceholderText("Select up to 4 auto-routers"), "gpt-auto");
+        await user.click(screen.getByPlaceholderText("Select a judge model"));
+        expect(screen.getAllByRole("option")).toHaveLength(2);
+        expect(screen.getByRole("option", { name: "custom-chat", exact: true })).toBeInTheDocument();
+        expect(screen.getByRole("option", { name: "custom-judge", exact: true })).toBeInTheDocument();
+        await user.click(screen.getByRole("option", { name: "custom-judge", exact: true }));
+        await user.click(screen.getByPlaceholderText("Select a baseline model"));
+        expect(screen.getAllByRole("option")).toHaveLength(2);
+        expect(screen.getByRole("option", { name: "custom-chat", exact: true })).toBeInTheDocument();
+        expect(screen.getByRole("option", { name: "custom-judge", exact: true })).toBeInTheDocument();
+        await user.click(screen.getByRole("option", { name: "custom-chat", exact: true }));
+        await user.click(screen.getByText("Start shadow eval"));
+        expect(start.mutate).toHaveBeenCalledWith(
+          expect.objectContaining({ judge_model: "custom-judge", baseline_model: "custom-chat", models: [] }),
+        );
+      });
+    });
+    client.clear();
+  });
+
   it("offers the start form while the list is still loading", () => {
     mockHooks({ isPending: true });
     render(<ShadowEvalSection />);
@@ -444,7 +532,8 @@ describe("ShadowEvalSection", () => {
     expect(screen.getByText("Start shadow eval")).toBeDisabled();
 
     await user.click(screen.getByPlaceholderText("Select a judge model"));
-    await user.click(await screen.findByRole("option", { name: /anthropic\/claude-sonnet-5/ }));
+    expect(screen.queryByRole("option", { name: /openai\/gpt-4o/ })).not.toBeInTheDocument();
+    await user.click(await screen.findByRole("option", { name: /prod-judge/ }));
     await user.click(screen.getByText("Start shadow eval"));
 
     const expectedBody = {
@@ -457,7 +546,7 @@ describe("ShadowEvalSection", () => {
       shadow_percentage: 10,
       duration_days: 7,
       max_budget: 10,
-      judge_model: "anthropic/claude-sonnet-5",
+      judge_model: "prod-judge",
     };
     expect(start.mutate).toHaveBeenCalledWith(expectedBody);
   });
@@ -474,7 +563,7 @@ describe("ShadowEvalSection", () => {
     await user.click(within(teamList).getByText("engineering"));
     await chooseSelectOption(user, screen.getByPlaceholderText("Select up to 4 auto-routers"), "gpt-auto");
     await user.click(screen.getByPlaceholderText("Select a judge model"));
-    await user.click(await screen.findByRole("option", { name: /anthropic\/claude-sonnet-5/ }));
+    await user.click(await screen.findByRole("option", { name: /prod-judge/ }));
     await user.click(screen.getByText("Start shadow eval"));
 
     const expectedBody = {
@@ -487,7 +576,7 @@ describe("ShadowEvalSection", () => {
       shadow_percentage: 10,
       duration_days: 7,
       max_budget: 10,
-      judge_model: "anthropic/claude-sonnet-5",
+      judge_model: "prod-judge",
     };
     expect(start.mutate).toHaveBeenCalledWith(expectedBody);
   });
@@ -503,7 +592,7 @@ describe("ShadowEvalSection", () => {
     await chooseSelectOption(user, screen.getByPlaceholderText("Every model the targets use"), "prod-claude");
     await chooseSelectOption(user, screen.getByPlaceholderText("Select up to 4 auto-routers"), "gpt-auto");
     await user.click(screen.getByPlaceholderText("Select a judge model"));
-    await user.click(await screen.findByRole("option", { name: /anthropic\/claude-sonnet-5/ }));
+    await user.click(await screen.findByRole("option", { name: /prod-judge/ }));
     await user.click(screen.getByText("Start shadow eval"));
 
     expect(start.mutate).toHaveBeenCalledWith(
@@ -524,20 +613,23 @@ describe("ShadowEvalSection", () => {
     expect(screen.queryByPlaceholderText("Select a baseline model")).not.toBeInTheDocument();
     expect(screen.getByPlaceholderText("Every model the targets use")).toBeInTheDocument();
 
-    await user.click(screen.getByText("Adoption check: key's traffic vs the router"));
-    await user.click(await screen.findByText("Regression check: router's picks vs a baseline"));
+    await chooseSelectOption(
+      user,
+      screen.getByText("Adoption check: key's traffic vs the router"),
+      "Regression check: router's picks vs a baseline",
+    );
     expect(screen.queryByPlaceholderText("Every model the targets use")).not.toBeInTheDocument();
     await user.click(screen.getByPlaceholderText("Search keys by alias"));
     const keyList = await screen.findByTestId("paginated-multi-select-list");
     await user.click(within(keyList).getByText("prod-alpha"));
     await chooseSelectOption(user, screen.getByPlaceholderText("Select up to 4 auto-routers"), "gpt-auto");
     await user.click(screen.getByPlaceholderText("Select a judge model"));
-    await user.click(await screen.findByRole("option", { name: /anthropic\/claude-sonnet-5/ }));
+    await user.click(await screen.findByRole("option", { name: /prod-judge/ }));
 
     expect(screen.getByText("Start shadow eval")).toBeDisabled();
 
     await user.click(screen.getByPlaceholderText("Select a baseline model"));
-    expect(await screen.findByRole("option", { name: /openai\/gpt-4o/ })).toBeInTheDocument();
+    expect(screen.queryByRole("option", { name: /openai\/gpt-4o/ })).not.toBeInTheDocument();
     await user.click(screen.getByRole("option", { name: /prod-claude/ }));
     await user.click(screen.getByText("Start shadow eval"));
 
@@ -552,7 +644,7 @@ describe("ShadowEvalSection", () => {
       shadow_percentage: 10,
       duration_days: 7,
       max_budget: 10,
-      judge_model: "anthropic/claude-sonnet-5",
+      judge_model: "prod-judge",
     };
     expect(start.mutate).toHaveBeenCalledWith(expectedBody);
   });
@@ -574,7 +666,7 @@ describe("ShadowEvalSection", () => {
       screen.getByText("Every router sees the same sampled requests, judged against the same live responses"),
     ).toBeInTheDocument();
     await user.click(screen.getByPlaceholderText("Select a judge model"));
-    await user.click(await screen.findByRole("option", { name: /anthropic\/claude-sonnet-5/ }));
+    await user.click(await screen.findByRole("option", { name: /prod-judge/ }));
     await user.click(screen.getByText("Start shadow eval"));
 
     const expectedBody = {
@@ -587,7 +679,7 @@ describe("ShadowEvalSection", () => {
       shadow_percentage: 10,
       duration_days: 7,
       max_budget: 10,
-      judge_model: "anthropic/claude-sonnet-5",
+      judge_model: "prod-judge",
     };
     expect(start.mutate).toHaveBeenCalledWith(expectedBody);
   });
@@ -605,10 +697,13 @@ describe("ShadowEvalSection", () => {
     await user.click(await screen.findByText("gpt-auto"));
     await user.click(routerInput);
     await user.click(await screen.findByText("claude-auto"));
-    await user.click(screen.getByText("Adoption check: key's traffic vs the router"));
-    await user.click(await screen.findByText("Regression check: router's picks vs a baseline"));
+    await chooseSelectOption(
+      user,
+      screen.getByText("Adoption check: key's traffic vs the router"),
+      "Regression check: router's picks vs a baseline",
+    );
     await user.click(screen.getByPlaceholderText("Select a judge model"));
-    await user.click(await screen.findByRole("option", { name: /anthropic\/claude-sonnet-5/ }));
+    await user.click(await screen.findByRole("option", { name: /prod-judge/ }));
     await user.click(screen.getByPlaceholderText("Select a baseline model"));
     await user.click(screen.getByRole("option", { name: /prod-claude/ }));
 
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalStartForm.tsx b/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalStartForm.tsx
index 2eb5fa9c945..d85d26a21a8 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalStartForm.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/cost-optimization/_components/ShadowEvalStartForm.tsx
@@ -5,8 +5,13 @@ import React, { useMemo, useState } from "react";
 import { useInfiniteKeys } from "@/app/(dashboard)/hooks/keys/useKeys";
 import { useInfiniteUsers } from "@/app/(dashboard)/hooks/users/useUsers";
 import useAuthorized from "@/app/(dashboard)/hooks/useAuthorized";
-import { useModelCostMap } from "@/app/(dashboard)/hooks/models/useModelCostMap";
-import { useAutoRouters, usePlainModelGroups } from "@/app/(dashboard)/hooks/models/useModels";
+import {
+  useAutoRouters,
+  usePlainChatModelDeployments,
+  usePlainChatModelGroups,
+  usePlainModelGroups,
+} from "@/app/(dashboard)/hooks/models/useModels";
+import { buildModelAvailability, deploymentRefsFromModelInfo, resolveAvailableModels } from "@/lib/autorouter_presets";
 import { MultiSelect } from "@/components/shared/MultiSelect";
 import { PaginatedMultiSelect } from "@/components/shared/PaginatedMultiSelect";
 import TeamMultiSelect from "@/components/common_components/team_multi_select";
@@ -24,53 +29,8 @@ type ShadowEvalDirection = ShadowEvalJob["direction"];
 
 const MAX_ROUTERS = 4;
 const MAX_MODELS = 100;
-
 const RECOMMENDED_JUDGE_MODELS = ["anthropic/claude-sonnet-5", "openai/gpt-4o", "gemini/gemini-2.5-pro"] as const;
 
-interface CostMapEntry {
-  litellm_provider?: string;
-  mode?: string;
-}
-
-const useChatModelNames = (): string[] => {
-  const { data: costMap } = useModelCostMap();
-  return useMemo(() => {
-    if (!costMap) return [];
-    const chatModels = Object.entries(costMap as Record<string, CostMapEntry>)
-      .filter(([, value]) => value?.mode === "chat" && value?.litellm_provider)
-      .map(([key, value]) => (key.startsWith(`${value.litellm_provider}/`) ? key : `${value.litellm_provider}/${key}`));
-    return [...new Set(chatModels)].toSorted((a, b) => a.localeCompare(b));
-  }, [costMap]);
-};
-
-const useJudgeModelOptions = (): SearchSelectOption[] => {
-  const chatModels = useChatModelNames();
-  return useMemo(() => {
-    const pinned: SearchSelectOption[] = RECOMMENDED_JUDGE_MODELS.map((model) => ({
-      label: model,
-      value: model,
-      sublabel: "Recommended",
-    }));
-    const pinnedNames = new Set<string>(RECOMMENDED_JUDGE_MODELS);
-    const rest = chatModels.filter((model) => !pinnedNames.has(model)).map((model) => ({ label: model, value: model }));
-    return [...pinned, ...rest];
-  }, [chatModels]);
-};
-
-const useBaselineModelOptions = (): SearchSelectOption[] => {
-  const configuredGroups = usePlainModelGroups();
-  const chatModels = useChatModelNames();
-  return useMemo(() => {
-    const configured = [...configuredGroups]
-      .toSorted((a, b) => a.localeCompare(b))
-      .map((model) => ({ label: model, value: model, sublabel: "Configured on this gateway" }));
-    const rest = chatModels
-      .filter((model) => !configuredGroups.has(model))
-      .map((model) => ({ label: model, value: model }));
-    return [...configured, ...rest];
-  }, [configuredGroups, chatModels]);
-};
-
 const DIRECTION_OPTIONS: readonly { value: ShadowEvalDirection; label: string }[] = [
   { value: "forward", label: "Adoption check: key's traffic vs the router" },
   { value: "reverse", label: "Regression check: router's picks vs a baseline" },
@@ -276,13 +236,32 @@ export const StartForm: React.FC = () => {
   const [judgeModel, setJudgeModel] = useState("");
   const [maxBudget, setMaxBudget] = useState("10");
   const { data: autoRouters } = useAutoRouters();
-  const judgeModelOptions = useJudgeModelOptions();
-  const baselineModelOptions = useBaselineModelOptions();
   const configuredGroups = usePlainModelGroups();
+  const chatGroups = usePlainChatModelGroups();
+  const chatDeployments = usePlainChatModelDeployments();
   const modelOptions = useMemo<SearchSelectOption[]>(
     () => [...configuredGroups].toSorted((a, b) => a.localeCompare(b)).map((name) => ({ label: name, value: name })),
     [configuredGroups],
   );
+  const chatOptions = useMemo(
+    () => modelOptions.filter((option) => chatGroups.has(option.value)),
+    [modelOptions, chatGroups],
+  );
+  const chatAvailability = useMemo(
+    () => buildModelAvailability(chatGroups, deploymentRefsFromModelInfo(chatDeployments)),
+    [chatDeployments, chatGroups],
+  );
+  const recommendedJudgeModels = useMemo(
+    () => new Set(RECOMMENDED_JUDGE_MODELS.flatMap((model) => resolveAvailableModels(model, chatAvailability))),
+    [chatAvailability],
+  );
+  const judgeOptions = useMemo(
+    () =>
+      chatOptions.map((option) =>
+        recommendedJudgeModels.has(option.value) ? { ...option, sublabel: "Recommended" } : option,
+      ),
+    [chatOptions, recommendedJudgeModels],
+  );
   const start = useStartShadowEval();
 
   const routerOptions = useMemo<SearchSelectOption[]>(() => {
@@ -434,7 +413,7 @@ export const StartForm: React.FC = () => {
           {direction === "reverse" && (
             <Field label="Baseline model">
               <SearchSelect
-                options={baselineModelOptions}
+                options={chatOptions}
                 value={baselineModel}
                 onValueChange={setBaselineModel}
                 placeholder="Select a baseline model"
@@ -444,7 +423,7 @@ export const StartForm: React.FC = () => {
           )}
           <Field label="Judge model" className="sm:col-span-2">
             <SearchSelect
-              options={judgeModelOptions}
+              options={judgeOptions}
               value={judgeModel}
               onValueChange={setJudgeModel}
               placeholder="Select a judge model"
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails.ts b/ui/litellm-dashboard/src/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails.ts
index 307fa9e1691..44d9092df34 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails.ts
@@ -14,6 +14,7 @@ export interface HealthReadinessDetailsResponse {
   log_level?: string;
   is_detailed_debug?: boolean;
   show_no_redis_warning?: boolean;
+  show_env_credential_login_warning?: boolean;
 }
 
 const fetchHealthReadinessDetails = async (accessToken: string): Promise<HealthReadinessDetailsResponse> => {
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.test.ts b/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.test.ts
index cfafe82ee30..6489bc2171d 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.test.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.test.ts
@@ -5,17 +5,19 @@ import { beforeEach, describe, expect, it, vi } from "vitest";
 import {
   isAutoRouterDeployment,
   selectAutoRouterModelGroups,
-  selectPlainModelGroups,
+  selectPlainChatModelGroups,
   useAllProxyModels,
   useAutoRouterModelGroups,
   useAutoRouters,
   useInfiniteModelInfo,
   useModelHub,
   useModelsInfo,
+  usePlainChatModelGroups,
   useSelectedTeamModels,
   useUserModels,
   type AllProxyModelsResponse,
   type AutoRouterCandidateDeployment,
+  type AutoRouterDeployment,
   type PaginatedModelInfoResponse,
   type ProxyModel,
 } from "./useModels";
@@ -984,29 +986,45 @@ describe("selectAutoRouterModelGroups", () => {
   });
 });
 
-describe("selectPlainModelGroups", () => {
-  it("keeps only non-auto-router model groups", () => {
-    const deployments: AutoRouterCandidateDeployment[] = [
-      { model_name: "smart-router", litellm_params: { model: "auto_router/complexity_router" } },
-      { model_name: "claude-haiku", litellm_params: { model: "anthropic/claude-haiku-4-5" } },
-      { model_name: "claude-sonnet", litellm_params: { model: "anthropic/claude-sonnet-4-5" } },
-      { model_name: "cheap-router", litellm_params: { model: "auto_router/adaptive_router" } },
+describe("selectPlainChatModelGroups", () => {
+  it("keeps chat-capable groups when mode metadata is absent or any sibling is compatible", () => {
+    const deployments: AutoRouterDeployment[] = [
+      { model_name: "no-info" },
+      { model_name: "null-info", model_info: null },
+      { model_name: "empty-info", model_info: {} },
+      { model_name: "missing-mode", model_info: { db_model: false } },
+      { model_name: "null-mode", model_info: { mode: null } },
+      { model_name: "empty-mode", model_info: { mode: "" } },
+      { model_name: "chat", model_info: { mode: "chat", db_model: true } },
+      { model_name: "completion", model_info: { mode: "completion" } },
+      { model_name: "chat-and-missing", model_info: { mode: "chat" } },
+      { model_name: "chat-and-missing" },
+      { model_name: "chat-then-embedding", model_info: { mode: "chat" } },
+      { model_name: "chat-then-embedding", model_info: { mode: "embedding" } },
+      { model_name: "embedding-then-chat", model_info: { mode: "embedding" } },
+      { model_name: "embedding-then-chat", model_info: { mode: "chat" } },
+      { model_name: "embedding-only", model_info: { mode: "embedding" } },
+      { model_name: "speech-only", model_info: { mode: "speech" } },
+      { model_name: "shared-router", litellm_params: { model: "openai/gpt-4o" } },
+      { model_name: "shared-router", litellm_params: { model: "auto_router/complexity_router" } },
+      { model_name: "", model_info: { mode: "chat" } },
     ];
 
-    expect(selectPlainModelGroups(deployments)).toEqual(new Set(["claude-haiku", "claude-sonnet"]));
-  });
-
-  it("drops a group name that also fronts an auto-router deployment", () => {
-    const deployments: AutoRouterCandidateDeployment[] = [
-      { model_name: "shared-name", litellm_params: { model: "auto_router/complexity_router" } },
-      { model_name: "shared-name", litellm_params: { model: "anthropic/claude-sonnet-4-5" } },
-    ];
-
-    expect(selectPlainModelGroups(deployments)).toEqual(new Set());
-  });
-
-  it("drops deployments that have no public model_name", () => {
-    expect(selectPlainModelGroups([{ model_name: "", litellm_params: { model: "openai/gpt-4o" } }])).toEqual(new Set());
+    expect(selectPlainChatModelGroups(deployments)).toEqual(
+      new Set([
+        "no-info",
+        "null-info",
+        "empty-info",
+        "missing-mode",
+        "null-mode",
+        "empty-mode",
+        "chat",
+        "completion",
+        "chat-and-missing",
+        "chat-then-embedding",
+        "embedding-then-chat",
+      ]),
+    );
   });
 });
 
@@ -1103,6 +1121,47 @@ describe("useAutoRouterModelGroups", () => {
     expect(modelInfoCall).toHaveBeenCalledWith("test-access-token", "test-user-id", "Admin", 3, 1000);
   });
 
+  it("uses every page for configured chat groups and keeps custom deployments without mode metadata", async () => {
+    (modelInfoCall as any).mockImplementation((_t: string, _u: string, _r: string, page: number) =>
+      Promise.resolve(
+        page === 1
+          ? {
+              data: [
+                { model_name: "configured-chat", model_info: { mode: "chat" } },
+                { model_name: "embedding-only", model_info: { mode: "embedding" } },
+              ],
+              total_pages: 2,
+            }
+          : {
+              data: [
+                { model_name: "custom-no-mode", model_info: { db_model: true } },
+                { model_name: "speech-only", model_info: { mode: "speech" } },
+              ],
+              total_pages: 2,
+            },
+      ),
+    );
+
+    const { result } = renderHook(() => usePlainChatModelGroups(), { wrapper });
+
+    await waitFor(() => expect(result.current.size).toBe(2));
+    expect(result.current).toEqual(new Set(["configured-chat", "custom-no-mode"]));
+    expect(modelInfoCall).toHaveBeenCalledTimes(2);
+  });
+
+  it("returns an empty chat group set while loading and after failure", async () => {
+    (modelInfoCall as any).mockReturnValueOnce(new Promise(() => {}));
+    const loading = renderHook(() => usePlainChatModelGroups(), { wrapper });
+    expect(loading.result.current).toEqual(new Set());
+    loading.unmount();
+
+    queryClient.clear();
+    (modelInfoCall as any).mockRejectedValueOnce(new Error("boom"));
+    const failed = renderHook(() => usePlainChatModelGroups(), { wrapper });
+    await waitFor(() => expect(modelInfoCall).toHaveBeenCalledTimes(2));
+    expect(failed.result.current).toEqual(new Set());
+  });
+
   it("returns an empty set before the model list resolves", () => {
     (modelInfoCall as any).mockReturnValue(new Promise(() => {}));
 
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.ts b/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.ts
index b3a783a71dc..579ee7ff81a 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/hooks/models/useModels.ts
@@ -2,6 +2,7 @@ import { useQuery, useInfiniteQuery, useQueryClient, UseQueryResult } from "@tan
 import { createQueryKeys } from "../common/queryKeysFactory";
 import { modelInfoCall, modelHubCall, modelAvailableCall } from "@/components/networking";
 import useAuthorized from "../useAuthorized";
+import { EndpointType, isModeCompatibleWithEndpoint } from "@/components/chat_ui/mode_endpoint_mapping";
 
 export interface ProxyModel {
   id: string;
@@ -87,6 +88,7 @@ export const useModelsInfo = (
 const AUTO_ROUTER_MODEL_PREFIX = "auto_router/";
 const AUTO_ROUTER_LOOKUP_PAGE_SIZE = 1000;
 const NO_AUTO_ROUTERS: ReadonlySet<string> = new Set<string>();
+const NO_DEPLOYMENTS: AutoRouterDeployment[] = [];
 
 export interface AutoRouterCandidateDeployment {
   model_name?: string | null;
@@ -96,6 +98,7 @@ export interface AutoRouterCandidateDeployment {
 export interface AutoRouterDeployment extends AutoRouterCandidateDeployment {
   litellm_params?: {
     model?: string | null;
+    base_model?: string | null;
     complexity_router_config?: unknown;
     complexity_router_default_model?: string | null;
     auto_router_config?: unknown;
@@ -111,6 +114,7 @@ export interface AutoRouterDeployment extends AutoRouterCandidateDeployment {
     /** False for config.yaml-defined deployments, which the update and delete routes refuse. */
     db_model?: boolean | null;
     base_model?: string | null;
+    mode?: string | null;
     created_at?: string | null;
     updated_at?: string | null;
     team_id?: string | null;
@@ -142,6 +146,22 @@ export const selectPlainModelGroups = (deployments: AutoRouterCandidateDeploymen
   );
 };
 
+export const selectPlainChatModelDeployments = (deployments: AutoRouterDeployment[]): AutoRouterDeployment[] => {
+  const plainGroups = selectPlainModelGroups(deployments);
+  return deployments.filter(
+    (deployment) =>
+      plainGroups.has(deployment.model_name ?? "") &&
+      isModeCompatibleWithEndpoint(deployment.model_info?.mode, EndpointType.CHAT),
+  );
+};
+
+export const selectPlainChatModelGroups = (deployments: AutoRouterDeployment[]): ReadonlySet<string> =>
+  new Set(
+    selectPlainChatModelDeployments(deployments)
+      .map((deployment) => deployment.model_name)
+      .filter((name): name is string => Boolean(name)),
+  );
+
 export const fetchAllModelDeployments = async (
   accessToken: string,
   userId: string,
@@ -180,37 +200,32 @@ export const autoRouterListKey = (userId: string | null, userRole: string | null
     },
   });
 
-export const useAutoRouterModelGroups = (): ReadonlySet<string> => {
+const useDeployments = <TSelected>(
+  select: (deployments: AutoRouterDeployment[]) => TSelected,
+): UseQueryResult<TSelected, Error> => {
   const { accessToken, userId, userRole } = useAuthorized();
-  const { data } = useQuery<AutoRouterDeployment[], Error, ReadonlySet<string>>({
+  return useQuery<AutoRouterDeployment[], Error, TSelected>({
     queryKey: autoRouterListKey(userId, userRole),
     queryFn: async () => await fetchAllModelDeployments(accessToken!, userId!, userRole!),
     enabled: Boolean(accessToken && userId && userRole),
-    select: selectAutoRouterModelGroups,
+    select,
   });
-  return data ?? NO_AUTO_ROUTERS;
 };
 
-export const usePlainModelGroups = (): ReadonlySet<string> => {
-  const { accessToken, userId, userRole } = useAuthorized();
-  const { data } = useQuery<AutoRouterDeployment[], Error, ReadonlySet<string>>({
-    queryKey: autoRouterListKey(userId, userRole),
-    queryFn: async () => await fetchAllModelDeployments(accessToken!, userId!, userRole!),
-    enabled: Boolean(accessToken && userId && userRole),
-    select: selectPlainModelGroups,
-  });
-  return data ?? NO_AUTO_ROUTERS;
-};
+export const useAutoRouterModelGroups = (): ReadonlySet<string> =>
+  useDeployments(selectAutoRouterModelGroups).data ?? NO_AUTO_ROUTERS;
 
-export const useAutoRouters = (): UseQueryResult<AutoRouterDeployment[], Error> => {
-  const { accessToken, userId, userRole } = useAuthorized();
-  return useQuery<AutoRouterDeployment[], Error, AutoRouterDeployment[]>({
-    queryKey: autoRouterListKey(userId, userRole),
-    queryFn: async () => await fetchAllModelDeployments(accessToken!, userId!, userRole!),
-    enabled: Boolean(accessToken && userId && userRole),
-    select: selectAutoRouterDeployments,
-  });
-};
+export const usePlainModelGroups = (): ReadonlySet<string> =>
+  useDeployments(selectPlainModelGroups).data ?? NO_AUTO_ROUTERS;
+
+export const usePlainChatModelGroups = (): ReadonlySet<string> =>
+  useDeployments(selectPlainChatModelGroups).data ?? NO_AUTO_ROUTERS;
+
+export const usePlainChatModelDeployments = (): AutoRouterDeployment[] =>
+  useDeployments(selectPlainChatModelDeployments).data ?? NO_DEPLOYMENTS;
+
+export const useAutoRouters = (): UseQueryResult<AutoRouterDeployment[], Error> =>
+  useDeployments(selectAutoRouterDeployments);
 
 export const useInvalidateAutoRouters = (): (() => Promise<void>) => {
   const queryClient = useQueryClient();
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.test.ts b/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.test.ts
index 960afe7392c..5448b7182d7 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.test.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.test.ts
@@ -81,7 +81,7 @@ describe("useOrganizations", () => {
       userRole: "Admin",
       token: "test-token",
       userEmail: "test@example.com",
-      premiumUser: false,
+      premiumUser: true,
       disabledPersonalKeyCreation: null,
       showSSOBanner: false,
     });
@@ -181,7 +181,7 @@ describe("useOrganizations", () => {
       userRole: "Admin",
       token: null,
       userEmail: "test@example.com",
-      premiumUser: false,
+      premiumUser: true,
       disabledPersonalKeyCreation: null,
       showSSOBanner: false,
     });
@@ -197,6 +197,26 @@ describe("useOrganizations", () => {
     expect(organizationListCall).not.toHaveBeenCalled();
   });
 
+  it("does not call the organization API when the session is not premium", async () => {
+    mockUseAuthorized.mockReturnValue({
+      accessToken: "test-access-token",
+      userId: "test-user-id",
+      userRole: "Admin",
+      token: "test-token",
+      userEmail: "test@example.com",
+      premiumUser: false,
+      disabledPersonalKeyCreation: null,
+      showSSOBanner: false,
+    });
+
+    const { result } = renderHook(() => useOrganizations(), { wrapper });
+
+    expect(result.current.isLoading).toBe(false);
+    expect(result.current.data).toBeUndefined();
+    expect(result.current.isFetched).toBe(false);
+    expect(organizationListCall).not.toHaveBeenCalled();
+  });
+
   it("should not execute query when userId is missing", async () => {
     // Mock missing userId
     mockUseAuthorized.mockReturnValue({
@@ -205,7 +225,7 @@ describe("useOrganizations", () => {
       userRole: "Admin",
       token: "test-token",
       userEmail: "test@example.com",
-      premiumUser: false,
+      premiumUser: true,
       disabledPersonalKeyCreation: null,
       showSSOBanner: false,
     });
@@ -229,7 +249,7 @@ describe("useOrganizations", () => {
       userRole: null,
       token: "test-token",
       userEmail: "test@example.com",
-      premiumUser: false,
+      premiumUser: true,
       disabledPersonalKeyCreation: null,
       showSSOBanner: false,
     });
@@ -253,7 +273,7 @@ describe("useOrganizations", () => {
       userRole: null,
       token: null,
       userEmail: "test@example.com",
-      premiumUser: false,
+      premiumUser: true,
       disabledPersonalKeyCreation: null,
       showSSOBanner: false,
     });
@@ -335,7 +355,7 @@ describe("useOrganization", () => {
       userRole: "Admin",
       token: "test-token",
       userEmail: "test@example.com",
-      premiumUser: false,
+      premiumUser: true,
       disabledPersonalKeyCreation: null,
       showSSOBanner: false,
     });
@@ -356,6 +376,26 @@ describe("useOrganization", () => {
     expect(result.current.isLoading).toBe(false);
   });
 
+  it("does not call the organization info API when the session is not premium", () => {
+    mockUseAuthorized.mockReturnValue({
+      accessToken: "test-access-token",
+      userId: "test-user-id",
+      userRole: "Admin",
+      token: "test-token",
+      userEmail: "test@example.com",
+      premiumUser: false,
+      disabledPersonalKeyCreation: null,
+      showSSOBanner: false,
+    });
+
+    const { result } = renderHook(() => useOrganization("org-1"), { wrapper });
+
+    expect(result.current.isLoading).toBe(false);
+    expect(result.current.data).toBeUndefined();
+    expect(result.current.isFetched).toBe(false);
+    expect(organizationInfoCall).not.toHaveBeenCalled();
+  });
+
   it("falls through to the detail API call when no cached list contains the organization", async () => {
     (organizationInfoCall as any).mockResolvedValue(mockOrganizations[0]);
     queryClient.setQueryData(organizationKeys.list({ filters: { org_id: "org-2" } }), [mockOrganizations[1]]);
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.ts b/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.ts
index 734c1986f8f..98053fdf038 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.ts
+++ b/ui/litellm-dashboard/src/app/(dashboard)/hooks/organizations/useOrganizations.ts
@@ -11,9 +11,10 @@ export interface OrganizationListFilters {
 }
 
 export const useOrganizations = (filters?: OrganizationListFilters): UseQueryResult<Organization[]> => {
-  const { accessToken, userId, userRole } = useAuthorized();
+  const { accessToken, userId, userRole, premiumUser } = useAuthorized();
   const orgId = filters?.org_id || null;
   const orgAlias = filters?.org_alias || null;
+  const hasSession = Boolean(accessToken && userId && userRole);
   return useQuery<Organization[]>({
     queryKey: organizationKeys.list(
       orgId || orgAlias
@@ -21,16 +22,16 @@ export const useOrganizations = (filters?: OrganizationListFilters): UseQueryRes
         : {},
     ),
     queryFn: async () => await organizationListCall(accessToken!, orgId, orgAlias),
-    enabled: Boolean(accessToken && userId && userRole),
+    enabled: hasSession && premiumUser === true,
   });
 };
 
 export const useOrganization = (organizationID?: string) => {
   const queryClient = useQueryClient();
-  const { accessToken } = useAuthorized();
+  const { accessToken, premiumUser } = useAuthorized();
   return useQuery<Organization>({
     queryKey: organizationKeys.detail(organizationID!),
-    enabled: Boolean(accessToken && organizationID),
+    enabled: Boolean(accessToken && organizationID) && premiumUser === true,
 
     queryFn: async () => {
       if (!accessToken || !organizationID) {
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/layout.test.tsx b/ui/litellm-dashboard/src/app/(dashboard)/layout.test.tsx
index 7f1f4cc4bd5..3fe34610260 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/layout.test.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/layout.test.tsx
@@ -29,6 +29,10 @@ vi.mock("@/components/NoRedisWarningBanner", () => ({
   NoRedisWarningBanner: () => null,
 }));
 
+vi.mock("@/components/EnvCredentialLoginWarningBanner", () => ({
+  EnvCredentialLoginWarningBanner: () => null,
+}));
+
 vi.mock("@/components/LicenseExpiryBanner", () => ({
   LicenseExpiryBanner: () => null,
 }));
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/layout.tsx b/ui/litellm-dashboard/src/app/(dashboard)/layout.tsx
index 98f2a36d6f3..fa6df7f176a 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/layout.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/layout.tsx
@@ -10,6 +10,7 @@ import SidebarProvider from "@/app/(dashboard)/components/SidebarProvider";
 import { useRouter, useSearchParams } from "next/navigation";
 import { DebugWarningBanner } from "@/components/DebugWarningBanner";
 import { NoRedisWarningBanner } from "@/components/NoRedisWarningBanner";
+import { EnvCredentialLoginWarningBanner } from "@/components/EnvCredentialLoginWarningBanner";
 import { LicenseExpiryBanner } from "@/components/LicenseExpiryBanner";
 import { UserBanner } from "@/components/UserBanner";
 import { uiHref } from "@/utils/uiHref";
@@ -113,6 +114,7 @@ function DashboardShell({ children }: { children: React.ReactNode }) {
         <Navbar accessToken={accessToken} isPublicPage={false} />
         <DebugWarningBanner accessToken={accessToken} />
         <NoRedisWarningBanner accessToken={accessToken} />
+        <EnvCredentialLoginWarningBanner accessToken={accessToken} />
         <LicenseExpiryBanner accessToken={accessToken} />
         <UserBanner accessToken={accessToken} />
         <main className="flex min-h-0 flex-1 overflow-hidden">
@@ -132,6 +134,7 @@ function DashboardShell({ children }: { children: React.ReactNode }) {
         <DashboardHeader />
         <DebugWarningBanner accessToken={accessToken} />
         <NoRedisWarningBanner accessToken={accessToken} />
+        <EnvCredentialLoginWarningBanner accessToken={accessToken} />
         <LicenseExpiryBanner accessToken={accessToken} />
         <UserBanner accessToken={accessToken} />
         <main className="min-w-0 flex-1 overflow-y-auto">{children}</main>
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/editToolPreview.test.ts b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/editToolPreview.test.ts
new file mode 100644
index 00000000000..c7147466d43
--- /dev/null
+++ b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/editToolPreview.test.ts
@@ -0,0 +1,105 @@
+import { describe, expect, it } from "vitest";
+import { getEditToolPreview } from "./editToolPreview";
+
+const saved = {
+  url: "https://example.com/mcp",
+  transport: "http",
+  auth_type: "basic",
+  static_headers: [{ header: "X-Tenant", value: "original" }],
+};
+
+describe("getEditToolPreview", () => {
+  it("keeps saved discovery for unchanged settings and unrelated edits", () => {
+    expect(getEditToolPreview({ ...saved, server_name: "renamed" }, saved)).toEqual({ kind: "saved" });
+  });
+
+  it("previews URL changes with the existing server credential left for server-side inheritance", () => {
+    expect(getEditToolPreview({ ...saved, url: "https://example.com/corrected-mcp" }, saved)).toEqual({
+      kind: "preview",
+      config: {
+        url: "https://example.com/corrected-mcp",
+        transport: "http",
+        auth_type: "basic",
+        static_headers: { "X-Tenant": "original" },
+        credentials: undefined,
+      },
+    });
+  });
+
+  it.each(["https://other.example/mcp", "http://example.com/mcp", "https://example.com:8443/mcp"])(
+    "requires explicit credentials for a changed origin: %s",
+    (url) => {
+      expect(getEditToolPreview({ ...saved, url, static_headers: [] }, saved)).toEqual({
+        kind: "incomplete",
+        message: expect.stringContaining("origin changed"),
+      });
+      const explicit = { ...saved, url, static_headers: [], credentials: { auth_value: "new:secret" } };
+      expect(getEditToolPreview(explicit, saved).kind).toBe("preview");
+    },
+  );
+
+  it("does not automatically send saved static headers to a new origin", () => {
+    expect(getEditToolPreview({ ...saved, url: "https://other.example/mcp", auth_type: "none" }, saved).kind).toBe(
+      "incomplete",
+    );
+  });
+
+  it("uses edited static headers and only the static auth value", () => {
+    expect(
+      getEditToolPreview(
+        {
+          ...saved,
+          static_headers: [{ header: "X-Tenant", value: "corrected" }],
+          credentials: { auth_value: "user:password", access_token: "old-oauth-token", client_secret: "old-client" },
+        },
+        saved,
+      ),
+    ).toEqual({
+      kind: "preview",
+      config: {
+        url: saved.url,
+        transport: "http",
+        auth_type: "basic",
+        static_headers: { "X-Tenant": "corrected" },
+        credentials: { auth_value: "user:password" },
+      },
+    });
+  });
+
+  it.each(["", "https://", "file:///tmp/server"])("does not connect to an incomplete or unsupported URL: %s", (url) => {
+    expect(getEditToolPreview({ ...saved, url }, saved)).toEqual({ kind: "incomplete" });
+  });
+
+  it("waits for a static header value before connecting", () => {
+    const values = { ...saved, static_headers: [{ header: "X-Tenant", value: "" }] };
+    expect(getEditToolPreview(values, saved)).toEqual({ kind: "incomplete" });
+  });
+
+  it("waits for credentials when switching from None to Basic Auth", () => {
+    expect(getEditToolPreview(saved, { ...saved, auth_type: "none" })).toEqual({ kind: "incomplete" });
+  });
+
+  it("does not forward old credentials when switching to None", () => {
+    const result = getEditToolPreview(
+      { ...saved, auth_type: "none", credentials: { auth_value: "old-secret" } },
+      saved,
+    );
+    expect(result.kind).toBe("preview");
+    if (result.kind === "preview") expect(result.config.credentials).toBeUndefined();
+  });
+
+  it.each(["oauth2", "true_passthrough", "oauth_delegate", "oauth2_token_exchange", "oauth2_id_jag", "aws_sigv4"])(
+    "preserves the existing discovery path for %s",
+    (auth_type) => {
+      expect(getEditToolPreview({ ...saved, auth_type, url: "https://changed.example/mcp" }, saved)).toEqual({
+        kind: "saved",
+      });
+    },
+  );
+
+  it("keeps stdio and OpenAPI on their existing discovery path", () => {
+    for (const transport of ["stdio", "openapi"]) {
+      expect(getEditToolPreview({ ...saved, transport }, saved)).toEqual({ kind: "saved" });
+    }
+  });
+});
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/editToolPreview.ts b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/editToolPreview.ts
new file mode 100644
index 00000000000..6dea7d7d18e
--- /dev/null
+++ b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/editToolPreview.ts
@@ -0,0 +1,67 @@
+import { AUTH_TYPE, TRANSPORT } from "@/components/mcp_tools/types";
+import { AUTH_TYPES_REQUIRING_AUTH_VALUE, reduceStaticHeaders } from "./createServerPayload";
+
+const connectionConfig = (values: Readonly<Record<string, unknown>>) => {
+  const credentials = values.credentials;
+  const authValue =
+    credentials && typeof credentials === "object" && "auth_value" in credentials ? credentials.auth_value : undefined;
+  const needsAuthValue =
+    typeof values.auth_type === "string" && AUTH_TYPES_REQUIRING_AUTH_VALUE.includes(values.auth_type);
+  return {
+    url: typeof values.url === "string" ? values.url : "",
+    transport: typeof values.transport === "string" ? values.transport : "",
+    auth_type: typeof values.auth_type === "string" ? values.auth_type : "",
+    static_headers: Object.fromEntries(
+      Object.entries(reduceStaticHeaders(values.static_headers)).sort(([a], [b]) => a.localeCompare(b)),
+    ),
+    credentials:
+      needsAuthValue && typeof authValue === "string" && authValue.trim() ? { auth_value: authValue } : undefined,
+  };
+};
+
+type EditToolPreview =
+  | { readonly kind: "saved" }
+  | { readonly kind: "incomplete"; readonly message?: string }
+  | { readonly kind: "preview"; readonly config: ReturnType<typeof connectionConfig> };
+
+export const getEditToolPreview = (
+  values: Readonly<Record<string, unknown>>,
+  initialValues: Readonly<Record<string, unknown>>,
+): EditToolPreview => {
+  const staticAuth =
+    values.auth_type === AUTH_TYPE.NONE ||
+    (typeof values.auth_type === "string" && AUTH_TYPES_REQUIRING_AUTH_VALUE.includes(values.auth_type));
+  if (!staticAuth || ![TRANSPORT.HTTP, TRANSPORT.SSE].includes(String(values.transport))) {
+    return { kind: "saved" };
+  }
+
+  const config = connectionConfig(values);
+  if (JSON.stringify(config) === JSON.stringify(connectionConfig(initialValues))) {
+    return { kind: "saved" };
+  }
+
+  const missingNewCredential =
+    config.auth_type !== initialValues.auth_type &&
+    AUTH_TYPES_REQUIRING_AUTH_VALUE.includes(config.auth_type) &&
+    config.credentials === undefined;
+  const validUrl = URL.canParse(config.url) && ["http:", "https:"].includes(new URL(config.url).protocol);
+  const incompleteHeaders = Object.values(config.static_headers).some((value) => !value.trim());
+  if (!validUrl || missingNewCredential || incompleteHeaders) {
+    return { kind: "incomplete" };
+  }
+  const savedConfig = connectionConfig(initialValues);
+  const changedOrigin =
+    !URL.canParse(savedConfig.url) || new URL(config.url).origin !== new URL(savedConfig.url).origin;
+  const reusesHeader = Object.entries(config.static_headers).some(
+    ([key, value]) => savedConfig.static_headers[key] === value,
+  );
+  const needsSavedCredential = AUTH_TYPES_REQUIRING_AUTH_VALUE.includes(config.auth_type) && !config.credentials;
+  if (changedOrigin && (needsSavedCredential || reusesHeader)) {
+    return {
+      kind: "incomplete",
+      message:
+        "The server origin changed. Enter credentials and replace or remove saved static headers to preview tools.",
+    };
+  }
+  return { kind: "preview", config };
+};
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.integration.test.tsx b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.integration.test.tsx
index a9664191f3f..f3cd37cc580 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.integration.test.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.integration.test.tsx
@@ -1,6 +1,9 @@
 import React from "react";
 import { describe, it, expect, vi, beforeEach } from "vitest";
-import { render, screen, waitFor, act } from "@testing-library/react";
+import { render, screen, waitFor, act, fireEvent } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+
+import { selectOption } from "./testUtils";
 
 import MCPServerEdit from "./mcp_server_edit";
 import * as networking from "@/components/networking";
@@ -27,10 +30,6 @@ vi.mock("./mcp_server_cost_config", () => ({
   default: () => <div data-testid="mcp-cost-config" />,
 }));
 
-vi.mock("./mcp_tool_configuration", () => ({
-  default: () => <div data-testid="mcp-tool-config" />,
-}));
-
 const BASE: MCPServer = {
   server_id: "srv_1",
   server_name: "srv",
@@ -369,3 +368,105 @@ describe("mcp_server_edit save payload contract", () => {
     }
   });
 });
+
+describe("MCPServerEdit live tool preview", () => {
+  beforeEach(() => {
+    vi.resetAllMocks();
+    vi.mocked(networking.listMCPTools).mockResolvedValue({
+      tools: [],
+      error: "connection_error",
+      message: "Saved credentials rejected",
+    });
+    vi.mocked(networking.testMCPToolsListRequest).mockResolvedValue({
+      tools: [
+        { name: "echo", description: "Echo the supplied message", inputSchema: { type: "object", properties: {} } },
+      ],
+    });
+  });
+
+  const renderEditor = (server: MCPServer = BASE) =>
+    render(
+      <MCPServerEdit
+        mcpServer={server}
+        accessToken="access-token"
+        userID="user-1"
+        onCancel={vi.fn()}
+        onSuccess={vi.fn()}
+        availableAccessGroups={[]}
+      />,
+    );
+
+  it("replaces the saved connection failure with tools after correcting Basic Auth without saving", async () => {
+    renderEditor();
+    expect(await screen.findByText("Saved credentials rejected")).toBeInTheDocument();
+    await selectOption("Authentication", "Basic Auth");
+    fireEvent.change(screen.getByLabelText("Authentication Value"), { target: { value: "preview:correct" } });
+    expect(screen.queryByText("Saved credentials rejected")).not.toBeInTheDocument();
+    expect(screen.getByText("Loading tools...")).toBeInTheDocument();
+    expect(networking.testMCPToolsListRequest).not.toHaveBeenCalled();
+    fireEvent.click(await screen.findByRole("button", { name: "Flat List" }));
+    expect(screen.getByText("echo")).toBeInTheDocument();
+    const expectedConfig = {
+      server_id: BASE.server_id,
+      url: BASE.url,
+      auth_type: "basic",
+      credentials: { auth_value: "preview:correct" },
+    };
+    expect(networking.testMCPToolsListRequest).toHaveBeenCalledExactlyOnceWith(
+      "access-token",
+      expect.objectContaining(expectedConfig),
+    );
+    expect(networking.updateMCPServer).not.toHaveBeenCalled();
+  });
+
+  it("refreshes tools when a static header is corrected", async () => {
+    renderEditor({ ...BASE, static_headers: { "X-Preview-Key": "wrong" } });
+    expect(await screen.findByText("Saved credentials rejected")).toBeInTheDocument();
+    fireEvent.change(screen.getByPlaceholderText("Header value"), { target: { value: "correct" } });
+    fireEvent.click(await screen.findByRole("button", { name: "Flat List" }));
+    expect(screen.getByText("echo")).toBeInTheDocument();
+    expect(networking.testMCPToolsListRequest).toHaveBeenCalledExactlyOnceWith(
+      "access-token",
+      expect.objectContaining({ static_headers: { "X-Preview-Key": "correct" } }),
+    );
+  });
+
+  it("coalesces URL edits and ignores an older failed preview after the latest preview succeeds", async () => {
+    const user = userEvent.setup();
+    const older = Promise.withResolvers<{ tools: never[]; error: string; message: string }>();
+    vi.mocked(networking.testMCPToolsListRequest).mockImplementationOnce(() => older.promise);
+    renderEditor();
+    expect(await screen.findByText("Saved credentials rejected")).toBeInTheDocument();
+    fireEvent.change(screen.getByLabelText("MCP Server URL"), { target: { value: "https://first.example/mcp" } });
+    await waitFor(() => expect(networking.testMCPToolsListRequest).toHaveBeenCalledTimes(1));
+    await user.clear(screen.getByLabelText("MCP Server URL"));
+    await user.type(screen.getByLabelText("MCP Server URL"), "https://latest.example/mcp");
+    expect(networking.testMCPToolsListRequest).toHaveBeenCalledTimes(1);
+    fireEvent.click(await screen.findByRole("button", { name: "Flat List" }));
+    expect(screen.getByText("echo")).toBeInTheDocument();
+    expect(networking.testMCPToolsListRequest).toHaveBeenCalledTimes(2);
+    expect(networking.testMCPToolsListRequest).toHaveBeenLastCalledWith(
+      "access-token",
+      expect.objectContaining({ url: "https://latest.example/mcp" }),
+    );
+    await act(async () => older.resolve({ tools: [], error: "connection_error", message: "Older request failed" }));
+    expect(screen.getByText("echo")).toBeInTheDocument();
+    expect(screen.queryByText("Older request failed")).not.toBeInTheDocument();
+  });
+
+  it("ignores a saved-record response after editing and restores saved discovery when changes are reverted", async () => {
+    const saved = Promise.withResolvers<{ tools: never[]; error: string; message: string }>();
+    vi.mocked(networking.listMCPTools).mockImplementationOnce(() => saved.promise);
+    renderEditor();
+    await waitFor(() => expect(networking.listMCPTools).toHaveBeenCalledTimes(1));
+    fireEvent.change(screen.getByLabelText("MCP Server URL"), { target: { value: "https://correct.example/mcp" } });
+    fireEvent.click(await screen.findByRole("button", { name: "Flat List" }));
+    expect(screen.getByText("echo")).toBeInTheDocument();
+    await act(async () => saved.resolve({ tools: [], error: "connection_error", message: "Stale saved response" }));
+    expect(screen.getByText("echo")).toBeInTheDocument();
+    expect(screen.queryByText("Stale saved response")).not.toBeInTheDocument();
+    fireEvent.change(screen.getByLabelText("MCP Server URL"), { target: { value: BASE.url } });
+    expect(await screen.findByText("Saved credentials rejected")).toBeInTheDocument();
+    expect(networking.listMCPTools).toHaveBeenCalledTimes(2);
+  });
+});
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.tsx b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.tsx
index 8793c45371a..2a37029a2c4 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_server_edit.tsx
@@ -52,6 +52,7 @@ import EnvVarsSection from "./EnvVarsSection";
 import { validateMCPServerUrl, validateMCPServerName, normalizeToolOverrideMap } from "./utils";
 import { EditServerFormValues, buildEditServerPayload, editPayloadErrorMessage } from "./editServerPayload";
 import { toast } from "@/lib/toast";
+import { getEditToolPreview } from "./editToolPreview";
 import { useMcpOAuthFlow } from "@/hooks/useMcpOAuthFlow";
 import {
   MountedFormField,
@@ -449,14 +450,30 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
     }
   }, [mcpServer]);
 
-  // Fetch tools when component mounts for a saved server
+  const toolPreview = getEditToolPreview(allFieldsValue(form), initialValues);
+  const toolPreviewKey = JSON.stringify(toolPreview);
+
   useEffect(() => {
-    if (!mcpServer.server_id || mcpServer.server_id.trim() === "") {
+    const controller = new AbortController();
+    setTools([]);
+    setToolsError(null);
+    setIsLoadingTools(false);
+    if (!accessToken || !mcpServer.server_id) return;
+    if (toolPreview.kind === "incomplete") {
+      setToolsError(toolPreview.message ?? "Complete the URL, authentication, and header settings to load tools.");
       return;
     }
-    fetchTools();
+    setIsLoadingTools(true);
+    const timer = setTimeout(
+      () => fetchTools(() => !controller.signal.aborted),
+      toolPreview.kind === "preview" ? 500 : 0,
+    );
+    return () => {
+      controller.abort();
+      clearTimeout(timer);
+    };
     // eslint-disable-next-line react-hooks/exhaustive-deps
-  }, [mcpServer, accessToken, userID, oauthTokenResponse?.access_token]);
+  }, [mcpServer, accessToken, userID, oauthTokenResponse?.access_token, toolPreviewKey]);
 
   // Invalidate a token authorized in this edit session once any mint-relevant field diverges from the
   // identity it was minted against (url, auth_type, oauth_flow_type, client creds/scopes, or the
@@ -519,6 +536,7 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
   const previewWithStagedInteractiveToken = async (
     isPassthrough: boolean,
     isBrowserHeldTokenMode: boolean,
+    isCurrent: () => boolean,
   ): Promise<boolean> => {
     const stagedToken =
       !isPassthrough && !isBrowserHeldTokenMode && getEffectiveAuthType() === AUTH_TYPE.OAUTH2
@@ -550,6 +568,7 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
         registration_url: values.registration_url,
       };
       const toolsResponse = await testMCPToolsListRequest(accessToken, previewConfig, stagedToken);
+      if (!isCurrent()) return true;
       if (toolsResponse.tools && !toolsResponse.error) {
         setTools(toolsResponse.tools);
       } else {
@@ -557,15 +576,16 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
         setToolsError(toolsResponse.message || "Failed to load tools");
       }
     } catch (error) {
+      if (!isCurrent()) return true;
       setTools([]);
       setToolsError(error instanceof Error ? error.message : "Failed to load tools");
     } finally {
-      setIsLoadingTools(false);
+      if (isCurrent()) setIsLoadingTools(false);
     }
     return true;
   };
 
-  const fetchTools = async () => {
+  const fetchTools = async (isCurrent: () => boolean) => {
     if (!accessToken || !mcpServer.server_id) return;
 
     // OBO/M2M/static auth is attached server-side from the stored credential, so
@@ -574,6 +594,7 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
     // same way the Tools playground does.
     let customHeaders: Record<string, string> | undefined;
     const isPassthrough =
+      toolPreview.kind === "saved" &&
       getMcpOAuthMode({
         auth_type: mcpServer.auth_type,
         oauth2_flow: mcpServer.oauth2_flow,
@@ -581,9 +602,10 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
       }) === "passthrough";
     const isBrowserHeldTokenMode = isClientForwardedTokenMode(getEffectiveAuthType());
 
-    if (await previewWithStagedInteractiveToken(isPassthrough, isBrowserHeldTokenMode)) {
+    if (await previewWithStagedInteractiveToken(isPassthrough, isBrowserHeldTokenMode, isCurrent)) {
       return;
     }
+    if (!isCurrent()) return;
     if (isPassthrough || isBrowserHeldTokenMode) {
       const token =
         oauthTokenResponse?.access_token ??
@@ -591,6 +613,7 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
           ? getToken(mcpServer.server_id, userID)?.access_token ?? null
           : null);
       if (!token) {
+        setIsLoadingTools(false);
         setTools([]);
         setToolsError(
           isBrowserHeldTokenMode
@@ -608,7 +631,15 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
     try {
       // include_disabled_tools: configuring the allowlist needs the full server
       // catalog, so tools toggled off still render (as unchecked) instead of vanishing.
-      const toolsResponse = await listMCPTools(accessToken, mcpServer.server_id, customHeaders, true);
+      const toolsResponse =
+        toolPreview.kind === "preview"
+          ? await testMCPToolsListRequest(accessToken, {
+              ...toolPreview.config,
+              server_id: mcpServer.server_id,
+              server_name: mcpServer.server_name || mcpServer.alias,
+            })
+          : await listMCPTools(accessToken, mcpServer.server_id, customHeaders, true);
+      if (!isCurrent()) return;
 
       if (toolsResponse.tools && !toolsResponse.error) {
         setTools(toolsResponse.tools);
@@ -617,10 +648,11 @@ const MCPServerEdit: React.FC<MCPServerEditProps> = ({
         setToolsError(toolsResponse.message || "Failed to load tools");
       }
     } catch (error) {
+      if (!isCurrent()) return;
       setTools([]);
       setToolsError(error instanceof Error ? error.message : "Failed to load tools");
     } finally {
-      setIsLoadingTools(false);
+      if (isCurrent()) setIsLoadingTools(false);
     }
   };
 
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_tool_configuration.tsx b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_tool_configuration.tsx
index 274bdf63e32..a3d62de9941 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_tool_configuration.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/mcp-servers/_components/mcp_tool_configuration.tsx
@@ -433,7 +433,7 @@ const MCPToolConfiguration: React.FC<MCPToolConfigurationProps> = ({
         {isLoadingTools && (
           <div className="flex items-center justify-center gap-3 py-6">
             <UiLoadingSpinner className="size-6 text-muted-foreground" />
-            <p className="text-sm">Loading tools from spec...</p>
+            <p className="text-sm">Loading tools...</p>
           </div>
         )}
 
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.test.tsx b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.test.tsx
index f07b66efdf8..bf6b092a2b0 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.test.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.test.tsx
@@ -5,6 +5,7 @@ import { beforeEach, describe, expect, it, vi } from "vitest";
 import ChatUI from "./ChatUI";
 import * as fetchModelsModule from "@/components/llm_calls/fetch_models";
 import { makeOpenAIChatCompletionRequest } from "@/components/llm_calls/chat_completion";
+import { makeAnthropicMessagesRequest } from "../../llm_calls/anthropic_messages";
 
 vi.mock("@/components/llm_calls/fetch_models", () => ({
   fetchAvailableModels: vi.fn(),
@@ -14,6 +15,10 @@ vi.mock("@/components/llm_calls/chat_completion", () => ({
   makeOpenAIChatCompletionRequest: vi.fn().mockResolvedValue(undefined),
 }));
 
+vi.mock("../../llm_calls/anthropic_messages", () => ({
+  makeAnthropicMessagesRequest: vi.fn().mockResolvedValue(undefined),
+}));
+
 vi.mock("@/components/networking", () => ({
   tagListCall: vi.fn().mockResolvedValue({}),
   vectorStoreListCall: vi.fn().mockResolvedValue({ data: [] }),
@@ -32,6 +37,8 @@ beforeEach(() => {
 
 const CHAT_REQUEST_ARG_COUNT = 26;
 const STREAMING_ENABLED_ARG_INDEX = 25;
+const MESSAGES_REQUEST_ARG_COUNT = 19;
+const MESSAGES_STREAMING_ENABLED_ARG_INDEX = 18;
 
 async function openComboboxByPlaceholder(placeholder: string) {
   const user = userEvent.setup();
@@ -378,6 +385,52 @@ describe("ChatUI", () => {
     expect(requestArgs[STREAMING_ENABLED_ARG_INDEX]).toBe(false);
   });
 
+  it("should send the /v1/messages request non-streaming after Stream responses is unchecked", async () => {
+    const user = userEvent.setup();
+    render(
+      <ChatUI
+        accessToken="1234567890"
+        token="1234567890"
+        userRole="user"
+        userID="1234567890"
+        disabledPersonalKeyCreation={false}
+      />,
+    );
+
+    await waitFor(() => {
+      expect(screen.getByText("Test Key")).toBeInTheDocument();
+    });
+
+    await selectComboboxOption("Select an endpoint", "/v1/messages");
+    await selectComboboxOption("Select a Model", "Model 1");
+
+    await user.click(await screen.findByTestId("model-settings-button"));
+
+    const streamingCheckbox = await screen.findByRole("checkbox", { name: /Stream responses/i });
+    expect(streamingCheckbox).toBeChecked();
+    await user.click(streamingCheckbox);
+
+    await waitFor(() => {
+      expect(screen.getByRole("checkbox", { name: /Stream responses/i })).not.toBeChecked();
+    });
+
+    const messageInput = screen.getByPlaceholderText("Type your message... (Shift+Enter for new line)");
+    await act(async () => {
+      fireEvent.change(messageInput, { target: { value: "hello" } });
+    });
+    await act(async () => {
+      fireEvent.keyDown(messageInput, { key: "Enter", code: "Enter" });
+    });
+
+    await waitFor(() => {
+      expect(makeAnthropicMessagesRequest).toHaveBeenCalledTimes(1);
+    });
+
+    const requestArgs = vi.mocked(makeAnthropicMessagesRequest).mock.calls[0];
+    expect(requestArgs).toHaveLength(MESSAGES_REQUEST_ARG_COUNT);
+    expect(requestArgs[MESSAGES_STREAMING_ENABLED_ARG_INDEX]).toBe(false);
+  });
+
   it("should force streaming in simplified mode even when the playground setting is off", async () => {
     sessionStorage.setItem("streamingEnabled", "false");
 
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.tsx b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.tsx
index 35378d3d4e7..eca9e2323ae 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/ChatUI.tsx
@@ -1025,6 +1025,7 @@ const ChatUI: React.FC<ChatUIProps> = ({
             mcpServers,
             mcpServerToolRestrictions,
             mcpToolsets,
+            streamingEnabled,
           );
         } else if (endpointType === EndpointType.EMBEDDINGS) {
           await makeOpenAIEmbeddingsRequest(
@@ -1174,7 +1175,10 @@ const ChatUI: React.FC<ChatUIProps> = ({
     return !model.mode || model.mode === "chat";
   };
 
-  const supportsStreamingToggle = endpointType === EndpointType.CHAT || endpointType === EndpointType.RESPONSES;
+  const supportsStreamingToggle =
+    endpointType === EndpointType.CHAT ||
+    endpointType === EndpointType.RESPONSES ||
+    endpointType === EndpointType.ANTHROPIC_MESSAGES;
   const modelsForEndpoint = useMemo(
     () => filterModelsForEndpoint(modelInfo, endpointType as EndpointType),
     [modelInfo, endpointType],
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/EndpointUtils.tsx b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/EndpointUtils.tsx
index 8fd4a57dbfd..87d569f6490 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/EndpointUtils.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/components/chat_ui/EndpointUtils.tsx
@@ -1,7 +1,9 @@
 import { ModelGroup } from "@/components/llm_calls/fetch_models";
-import { EndpointType, getEndpointType, ModelMode } from "@/components/chat_ui/mode_endpoint_mapping";
-
-const KNOWN_MODEL_MODES = new Set<string>(Object.values(ModelMode));
+import {
+  EndpointType,
+  getEndpointType,
+  isModeCompatibleWithEndpoint,
+} from "@/components/chat_ui/mode_endpoint_mapping";
 
 export const determineEndpointType = (selectedModel: string, modelInfo: ModelGroup[]): EndpointType => {
   const selectedModelInfo = modelInfo.find((option) => option.model_group === selectedModel);
@@ -13,31 +15,8 @@ export const determineEndpointType = (selectedModel: string, modelInfo: ModelGro
   return EndpointType.CHAT;
 };
 
-export const isModelCompatibleWithEndpoint = (model: ModelGroup, endpointType: EndpointType): boolean => {
-  if (!model.mode) {
-    return true;
-  }
-
-  if (!KNOWN_MODEL_MODES.has(model.mode)) {
-    return false;
-  }
-
-  const optionEndpoint = getEndpointType(model.mode);
-
-  if (
-    endpointType === EndpointType.RESPONSES ||
-    endpointType === EndpointType.ANTHROPIC_MESSAGES ||
-    endpointType === EndpointType.INTERACTIONS
-  ) {
-    return optionEndpoint === endpointType || optionEndpoint === EndpointType.CHAT;
-  }
-
-  if (endpointType === EndpointType.IMAGE_EDITS) {
-    return optionEndpoint === endpointType || optionEndpoint === EndpointType.IMAGE;
-  }
-
-  return optionEndpoint === endpointType;
-};
+export const isModelCompatibleWithEndpoint = (model: ModelGroup, endpointType: EndpointType): boolean =>
+  isModeCompatibleWithEndpoint(model.mode, endpointType);
 
 export const filterModelsForEndpoint = (models: ModelGroup[], endpointType: EndpointType): ModelGroup[] =>
   models.filter((model) => isModelCompatibleWithEndpoint(model, endpointType));
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.test.tsx b/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.test.tsx
index 96ace129f87..9f030d8b2d4 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.test.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.test.tsx
@@ -7,13 +7,27 @@ vi.mock("@/components/networking", () => ({
 }));
 
 const mockMessagesStream = vi.fn();
+const mockMessagesCreate = vi.fn();
 
 vi.mock("@anthropic-ai/sdk", () => ({
   default: vi.fn(function () {
-    return { messages: { stream: mockMessagesStream } };
+    return { messages: { stream: mockMessagesStream, create: mockMessagesCreate } };
   }),
 }));
 
+const NON_STREAMING_ARGS = [
+  undefined, // traceId
+  undefined, // vector_store_ids
+  undefined, // guardrails
+  undefined, // policies
+  undefined, // selectedMCPServers
+  undefined, // customBaseUrl
+  undefined, // mcpServers
+  undefined, // mcpServerToolRestrictions
+  undefined, // mcpToolsets
+  false, // streamingEnabled
+] as const;
+
 describe("anthropic_messages prompt cache usage", () => {
   const captureUsage = async (usage: Record<string, unknown>): Promise<TokenUsage> => {
     async function* mockStream() {
@@ -59,3 +73,53 @@ describe("anthropic_messages prompt cache usage", () => {
     expect(usageData.promptTokens).toBe(5000);
   });
 });
+
+describe("anthropic_messages non-streaming", () => {
+  afterEach(() => {
+    vi.clearAllMocks();
+  });
+
+  it("sends stream:false through messages.create and renders the full reply at once", async () => {
+    mockMessagesCreate.mockResolvedValue({
+      content: [
+        { type: "thinking", thinking: "considering" },
+        { type: "text", text: "OK" },
+      ],
+      usage: { input_tokens: 12, output_tokens: 3, cache_read_input_tokens: 7 },
+    });
+    const updateTextUI = vi.fn();
+    const onReasoningContent = vi.fn();
+    const onUsageData = vi.fn();
+
+    await makeAnthropicMessagesRequest(
+      [{ role: "user", content: "Hello" }],
+      updateTextUI,
+      "claude-haiku-4-5",
+      "test-token",
+      undefined,
+      undefined,
+      onReasoningContent,
+      undefined,
+      onUsageData,
+      ...NON_STREAMING_ARGS,
+    );
+
+    expect(mockMessagesStream).not.toHaveBeenCalled();
+    expect(mockMessagesCreate).toHaveBeenCalledTimes(1);
+    expect(mockMessagesCreate.mock.calls[0][0]).toMatchObject({ model: "claude-haiku-4-5", stream: false });
+    expect(updateTextUI).toHaveBeenCalledWith("assistant", "OK", "claude-haiku-4-5");
+    expect(onReasoningContent).toHaveBeenCalledWith("considering");
+    const expectedUsage: TokenUsage = { completionTokens: 3, promptTokens: 12, totalTokens: 15, cacheReadTokens: 7 };
+    expect(onUsageData).toHaveBeenCalledWith(expectedUsage);
+  });
+
+  it("keeps streaming as the default when the flag is omitted", async () => {
+    async function* emptyStream() {}
+    mockMessagesStream.mockReturnValue(emptyStream());
+
+    await makeAnthropicMessagesRequest([{ role: "user", content: "Hello" }], vi.fn(), "claude-haiku-4-5", "test-token");
+
+    expect(mockMessagesCreate).not.toHaveBeenCalled();
+    expect(mockMessagesStream.mock.calls[0][0]).toMatchObject({ stream: true });
+  });
+});
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.tsx b/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.tsx
index 14afa013768..9dd2f675c44 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/playground/llm_calls/anthropic_messages.tsx
@@ -7,6 +7,13 @@ import { getProxyBaseUrl } from "@/components/networking";
 import { toast } from "@/lib/toast";
 import { extractPromptCacheTokens } from "@/utils/promptCacheUsage";
 
+const toTokenUsage = (usage: Anthropic.Usage): TokenUsage => ({
+  completionTokens: usage.output_tokens,
+  promptTokens: usage.input_tokens,
+  totalTokens: usage.input_tokens + usage.output_tokens,
+  ...extractPromptCacheTokens(usage),
+});
+
 export async function makeAnthropicMessagesRequest(
   messages: MessageType[],
   updateTextUI: (role: string, delta: string, model?: string) => void,
@@ -26,6 +33,7 @@ export async function makeAnthropicMessagesRequest(
   mcpServers?: MCPServer[],
   mcpServerToolRestrictions?: Record<string, string[]>,
   mcpToolsets?: MCPToolset[],
+  streamingEnabled: boolean = true,
 ) {
   if (!accessToken) {
     throw new Error("Virtual Key is required");
@@ -58,7 +66,7 @@ export async function makeAnthropicMessagesRequest(
     const requestBody: any = {
       model: selectedModel,
       messages: messages.map((m) => ({ role: m.role, content: m.content })),
-      stream: true,
+      stream: streamingEnabled,
       max_tokens: 1024,
       // @ts-ignore - litellm specific parameter
       litellm_trace_id: traceId,
@@ -74,6 +82,20 @@ export async function makeAnthropicMessagesRequest(
     if (vector_store_ids) requestBody.vector_store_ids = vector_store_ids;
     if (guardrails) requestBody.guardrails = guardrails;
     if (policies) requestBody.policies = policies;
+
+    if (!streamingEnabled) {
+      const message: Anthropic.Message = await client.messages.create({ ...requestBody, stream: false }, { signal });
+      for (const block of message.content) {
+        if (block.type === "text") {
+          updateTextUI("assistant", block.text, selectedModel);
+        } else if (block.type === "thinking" && onReasoningContent) {
+          onReasoningContent(block.thinking);
+        }
+      }
+      onUsageData?.(toTokenUsage(message.usage));
+      return;
+    }
+
     // Use the streaming helper method for cleaner async iteration
     // @ts-ignore - The SDK types might not include all litellm-specific parameters
     const stream = client.messages.stream(requestBody, { signal });
@@ -105,14 +127,7 @@ export async function makeAnthropicMessagesRequest(
 
       // Process usage data from message_delta events
       if (messageStreamEvent.type === "message_delta" && (messageStreamEvent as any).usage && onUsageData) {
-        const usage = (messageStreamEvent as any).usage;
-        const usageData: TokenUsage = {
-          completionTokens: usage.output_tokens,
-          promptTokens: usage.input_tokens,
-          totalTokens: usage.input_tokens + usage.output_tokens,
-          ...extractPromptCacheTokens(usage),
-        };
-        onUsageData(usageData);
+        onUsageData(toTokenUsage((messageStreamEvent as any).usage));
       }
     }
   } catch (error) {
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.test.tsx b/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.test.tsx
index 1058d4d0466..6507855d0c7 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.test.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.test.tsx
@@ -20,21 +20,25 @@ const DEFAULT_PROPS = {
   onSuccess: vi.fn(),
 };
 
-const URL_PLACEHOLDER = "https://github.com/org/repo or https://gitlab.com/org/repo";
+const URL_PLACEHOLDER = "https://github.com/org/repo or https://bucket.s3.amazonaws.com/my-skill.zip";
 const SUBPATH_PLACEHOLDER = "plugins/my-skill";
+const SHA256_PLACEHOLDER = "64 hex characters";
+const S3_ZIP_URL = "https://skills-bucket.s3.us-east-1.amazonaws.com/plugins/s3-skill-1.0.0.zip";
+const DIGEST = "e3b0c44298fc1c149afbf4c8996fb92427ae41e4649b934ca495991b7852b855";
 
 describe("AddPluginForm", () => {
   beforeEach(() => {
     vi.clearAllMocks();
   });
 
-  it("renders the host-agnostic repository URL input and subfolder field", () => {
+  it("renders the host-agnostic source URL input and subfolder field, hiding the digest until a zip is entered", () => {
     renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
 
-    expect(screen.getByText("Repository URL")).toBeInTheDocument();
+    expect(screen.getByText("Source URL")).toBeInTheDocument();
     expect(screen.getByPlaceholderText(URL_PLACEHOLDER)).toBeInTheDocument();
     expect(screen.getByText("Subfolder path (Optional)")).toBeInTheDocument();
     expect(screen.getByPlaceholderText(SUBPATH_PLACEHOLDER)).toBeInTheDocument();
+    expect(screen.queryByPlaceholderText(SHA256_PLACEHOLDER)).not.toBeInTheDocument();
   });
 
   it("shows GitHub repo preview for a plain repo URL", async () => {
@@ -255,6 +259,85 @@ describe("AddPluginForm", () => {
     });
   });
 
+  it("shows a zip archive preview, disables the subfolder field, and reveals the digest field", async () => {
+    renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
+
+    await typeUrl(S3_ZIP_URL);
+
+    expect(await screen.findByText(/Zip archive/)).toBeInTheDocument();
+    expect(screen.getByPlaceholderText(SUBPATH_PLACEHOLDER)).toBeDisabled();
+    expect(screen.getByText("A zip archive is installed as a whole, so this field is disabled")).toBeInTheDocument();
+    expect(screen.getByPlaceholderText(SHA256_PLACEHOLDER)).toBeInTheDocument();
+    expect((screen.getByPlaceholderText("my-skill") as HTMLInputElement).value).toBe("s3-skill-1-0-0");
+  });
+
+  it("submits an archive source without a digest when the field is left empty", async () => {
+    renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
+
+    await typeUrl(S3_ZIP_URL);
+    await submit();
+
+    await waitFor(() => {
+      expect(mockRegister).toHaveBeenCalledWith(
+        "sk-test",
+        expect.objectContaining({ source: { source: "archive", url: S3_ZIP_URL } }),
+      );
+    });
+  });
+
+  it("submits an archive source pinned to the lowercased digest", async () => {
+    renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
+
+    await typeUrl(S3_ZIP_URL);
+    await act(async () => {
+      fireEvent.change(screen.getByPlaceholderText(SHA256_PLACEHOLDER), {
+        target: { value: ` ${DIGEST.toUpperCase()} ` },
+      });
+    });
+    await submit();
+
+    await waitFor(() => {
+      expect(mockRegister).toHaveBeenCalledWith(
+        "sk-test",
+        expect.objectContaining({ source: { source: "archive", url: S3_ZIP_URL, sha256: DIGEST } }),
+      );
+    });
+  });
+
+  it("drops the digest once the archive URL changes so a stale checksum is never sent for a new file", async () => {
+    renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
+
+    await typeUrl(S3_ZIP_URL);
+    await act(async () => {
+      fireEvent.change(screen.getByPlaceholderText(SHA256_PLACEHOLDER), { target: { value: DIGEST } });
+    });
+    const otherZipUrl = S3_ZIP_URL.replace("1.0.0", "1.1.0");
+    await typeUrl(otherZipUrl);
+
+    expect(screen.getByPlaceholderText(SHA256_PLACEHOLDER)).toHaveValue("");
+    await submit();
+
+    await waitFor(() => {
+      expect(mockRegister).toHaveBeenCalledWith(
+        "sk-test",
+        expect.objectContaining({ source: { source: "archive", url: otherZipUrl } }),
+      );
+    });
+  });
+
+  it("blocks submission and shows the digest error for a malformed sha256", async () => {
+    renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
+
+    await typeUrl(S3_ZIP_URL);
+    await act(async () => {
+      fireEvent.change(screen.getByPlaceholderText(SHA256_PLACEHOLDER), { target: { value: "not-a-digest" } });
+    });
+    await submit();
+
+    expect(await screen.findByText("SHA-256 must be a 64-character hex digest")).toBeInTheDocument();
+    expect(mockRegister).not.toHaveBeenCalled();
+  });
+
   it("surfaces the backend error message when registration fails", async () => {
     mockRegister.mockRejectedValueOnce(new Error("Plugin 'claude-code' already exists"));
     renderWithProviders(<AddPluginForm {...DEFAULT_PROPS} />);
diff --git a/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.tsx b/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.tsx
index 70669ffc0cc..e420038b124 100644
--- a/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.tsx
+++ b/ui/litellm-dashboard/src/app/(dashboard)/skills/_components/add_plugin_form.tsx
@@ -26,6 +26,7 @@ import {
   parseKeywords,
   parseSkillSource,
   isValidSubPath,
+  isValidSha256,
   SkillSourcePreview,
 } from "@/components/claude_code_plugins/helpers";
 import { PluginAuthor, PluginSource, SkillRegisterRequest } from "@/components/claude_code_plugins/types";
@@ -39,13 +40,14 @@ interface AddPluginFormProps {
 }
 
 const addPluginShape = {
-  skillUrl: z.string().min(1, "Please enter a repository URL"),
+  skillUrl: z.string().min(1, "Please enter a repository or zip archive URL"),
   subPath: z
     .string()
     .refine(
       (value) => !value || isValidSubPath(value),
       "Subfolder must be a relative path like plugins/my-skill (letters, numbers, dots, hyphens, underscores)",
     ),
+  sha256: z.string().refine(isValidSha256, "SHA-256 must be a 64-character hex digest"),
   name: z
     .string()
     .min(1, "Please enter skill name")
@@ -69,6 +71,7 @@ type AddPluginFormValues = z.infer<typeof addPluginSchema>;
 const EMPTY_VALUES: AddPluginFormValues = {
   skillUrl: "",
   subPath: "",
+  sha256: "",
   name: "",
   domain: "",
   namespace: "",
@@ -89,11 +92,19 @@ const buildAuthor = (values: AddPluginFormValues): PluginAuthor | undefined => {
   return email ? { name, email } : { name };
 };
 
+const archiveUrlOf = (preview: SkillSourcePreview | null): string | undefined =>
+  preview?.parsed.source === "archive" ? preview.parsed.url : undefined;
+
+const withArchiveDigest = (source: PluginSource, sha256: string): PluginSource => {
+  const digest = sha256.trim();
+  return source.source === "archive" && digest ? { ...source, sha256: digest.toLowerCase() } : source;
+};
+
 const buildRegisterRequest = (values: AddPluginFormValues, source: PluginSource): SkillRegisterRequest => {
   const author = buildAuthor(values);
   return {
     name: values.name.trim(),
-    source,
+    source: withArchiveDigest(source, values.sha256),
     ...(values.version ? { version: values.version.trim() } : {}),
     ...(values.description ? { description: values.description.trim() } : {}),
     ...(author ? { author } : {}),
@@ -115,6 +126,16 @@ const PREDEFINED_CATEGORIES = [
   "Documentation",
 ];
 
+const SUB_PATH_LOCK_REASON = {
+  "git-subdir": "The URL already points to a subfolder, so this field is disabled",
+  archive: "A zip archive is installed as a whole, so this field is disabled",
+} as const;
+
+type SubPathLock = keyof typeof SUB_PATH_LOCK_REASON;
+
+const subPathLockFor = (source: PluginSource["source"] | undefined): SubPathLock | null =>
+  source === "git-subdir" || source === "archive" ? source : null;
+
 const labelWithHint = (label: string, hint: string): React.ReactNode => (
   <>
     {label}
@@ -129,15 +150,18 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
   const form = useZodForm(addPluginSchema, { defaultValues: EMPTY_VALUES });
   const [isSubmitting, setIsSubmitting] = useState(false);
   const [urlPreview, setUrlPreview] = useState<SkillSourcePreview | null>(null);
-  const [urlEncodesSubdir, setUrlEncodesSubdir] = useState(false);
+  const [subPathLock, setSubPathLock] = useState<SubPathLock | null>(null);
 
   const recomputePreview = (skillUrl: string, subPath: string) => {
-    const encodesSubdir = parseSkillSource(skillUrl)?.parsed.source === "git-subdir";
-    setUrlEncodesSubdir(encodesSubdir);
-    if (encodesSubdir && form.getValues("subPath")) {
+    const lock = subPathLockFor(parseSkillSource(skillUrl)?.parsed.source);
+    setSubPathLock(lock);
+    if (lock && form.getValues("subPath")) {
       form.setValue("subPath", "");
     }
-    const preview = parseSkillSource(skillUrl, encodesSubdir ? undefined : subPath);
+    const preview = parseSkillSource(skillUrl, lock ? undefined : subPath);
+    if (archiveUrlOf(preview) !== archiveUrlOf(urlPreview) && form.getValues("sha256")) {
+      form.setValue("sha256", "");
+    }
     setUrlPreview(preview);
     if (preview && !form.getValues("name")) {
       form.setValue("name", preview.suggestedName);
@@ -151,7 +175,7 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
     }
 
     if (!urlPreview) {
-      toast.error("Please enter a valid repository URL");
+      toast.error("Please enter a valid repository or zip archive URL");
       return;
     }
 
@@ -176,7 +200,7 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
       toast.success("Skill registered successfully");
       form.reset(EMPTY_VALUES);
       setUrlPreview(null);
-      setUrlEncodesSubdir(false);
+      setSubPathLock(null);
       onSuccess();
       onClose();
     } catch (error) {
@@ -190,7 +214,7 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
   const handleCancel = () => {
     form.reset(EMPTY_VALUES);
     setUrlPreview(null);
-    setUrlEncodesSubdir(false);
+    setSubPathLock(null);
     onClose();
   };
 
@@ -207,15 +231,15 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
                 control={form.control}
                 name="skillUrl"
                 label={labelWithHint(
-                  "Repository URL",
-                  "Paste an HTTPS git repository URL from GitHub, GitLab, Bitbucket, or a self-hosted host. E.g. github.com/org/repo, gitlab.com/org/repo, or github.com/org/repo/tree/main/my-skill",
+                  "Source URL",
+                  "Paste an HTTPS git repository URL from GitHub, GitLab, Bitbucket, or a self-hosted host (e.g. github.com/org/repo or github.com/org/repo/tree/main/my-skill), or an HTTPS link to a .zip archive of the skill hosted on S3 or any static file server.",
                 )}
               >
                 {({ ref, onChange, ...field }) => (
                   <Input
                     {...field}
                     ref={ref}
-                    placeholder="https://github.com/org/repo or https://gitlab.com/org/repo"
+                    placeholder="https://github.com/org/repo or https://bucket.s3.amazonaws.com/my-skill.zip"
                     className="rounded-lg"
                     onChange={(event) => {
                       onChange(event);
@@ -232,9 +256,7 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
                   "Subfolder path (Optional)",
                   "Path within the repository where the skill lives (e.g., plugins/my-skill). Leave empty if the skill is at the repo root.",
                 )}
-                description={
-                  urlEncodesSubdir ? "The URL already points to a subfolder, so this field is disabled" : undefined
-                }
+                description={subPathLock ? SUB_PATH_LOCK_REASON[subPathLock] : undefined}
               >
                 {({ ref, onChange, ...field }) => (
                   <Input
@@ -246,11 +268,26 @@ const AddPluginForm: React.FC<AddPluginFormProps> = ({ visible, onClose, accessT
                       onChange(event);
                       recomputePreview(form.getValues("skillUrl"), event.target.value);
                     }}
-                    disabled={urlEncodesSubdir}
+                    disabled={subPathLock !== null}
                   />
                 )}
               </FormField>
 
+              {urlPreview?.parsed.source === "archive" && (
+                <FormField
+                  control={form.control}
+                  name="sha256"
+                  label={labelWithHint(
+                    "Archive SHA-256 (Optional)",
+                    "Hex digest of the zip file. Claude Code refuses to install the archive if its checksum does not match.",
+                  )}
+                >
+                  {({ ref, ...field }) => (
+                    <Input {...field} ref={ref} placeholder="64 hex characters" className="rounded-lg font-mono" />
+                  )}
+                </FormField>
+              )}
+
               {urlPreview && (
                 <div className="rounded-lg border border-info/20 bg-info/10 px-3 py-2 text-sm text-info">
                   Detected: {urlPreview.label}
diff --git a/ui/litellm-dashboard/src/components/AIHub/SkillHubTableColumns.tsx b/ui/litellm-dashboard/src/components/AIHub/SkillHubTableColumns.tsx
index 2a1530cc352..1104e2c7485 100644
--- a/ui/litellm-dashboard/src/components/AIHub/SkillHubTableColumns.tsx
+++ b/ui/litellm-dashboard/src/components/AIHub/SkillHubTableColumns.tsx
@@ -26,7 +26,7 @@ function getSkillSourceLink(skill: Plugin): { url: string; label: string } | nul
     const url = src.path ? `${src.url}/tree/main/${src.path}` : src.url;
     return { url, label: url.replace("https://github.com/", "") };
   }
-  if (src?.source === "url" && src.url) {
+  if ((src?.source === "url" || src?.source === "archive") && src.url) {
     return { url: src.url, label: src.url.replace(/^https?:\/\//, "") };
   }
   return null;
diff --git a/ui/litellm-dashboard/src/components/EnvCredentialLoginWarningBanner.test.tsx b/ui/litellm-dashboard/src/components/EnvCredentialLoginWarningBanner.test.tsx
new file mode 100644
index 00000000000..535694f14da
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/EnvCredentialLoginWarningBanner.test.tsx
@@ -0,0 +1,76 @@
+import { renderWithProviders, screen } from "../../tests/test-utils";
+import { vi } from "vitest";
+import { EnvCredentialLoginWarningBanner } from "./EnvCredentialLoginWarningBanner";
+import type { HealthReadinessDetailsResponse } from "@/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails";
+import type { UseQueryResult } from "@tanstack/react-query";
+
+vi.mock("@/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails", () => ({
+  useHealthReadinessDetails: vi.fn(),
+}));
+vi.mock("@/contexts/AuthContext", () => ({
+  useAuth: vi.fn(),
+}));
+
+import { useHealthReadinessDetails } from "@/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails";
+import { useAuth } from "@/contexts/AuthContext";
+
+const mockDetails = (data: Partial<HealthReadinessDetailsResponse> | undefined) => {
+  vi.mocked(useHealthReadinessDetails).mockReturnValue({ data } as UseQueryResult<HealthReadinessDetailsResponse>);
+};
+
+const mockRole = (userRole: string) => {
+  vi.mocked(useAuth).mockReturnValue({ userRole } as ReturnType<typeof useAuth>);
+};
+
+describe("EnvCredentialLoginWarningBanner", () => {
+  it("should warn an admin when env-credential login is enabled", () => {
+    mockRole("Admin");
+    mockDetails({ status: "healthy", show_env_credential_login_warning: true });
+    renderWithProviders(<EnvCredentialLoginWarningBanner accessToken="token" />);
+    expect(screen.getByRole("alert")).toBeInTheDocument();
+    expect(screen.getByText("Environment-credential login is enabled")).toBeInTheDocument();
+  });
+
+  it("should tell the admin to create a regular admin account before disabling", () => {
+    mockRole("Admin");
+    mockDetails({ status: "healthy", show_env_credential_login_warning: true });
+    renderWithProviders(<EnvCredentialLoginWarningBanner accessToken="token" />);
+    expect(screen.getByText(/First create a regular admin account/i)).toBeInTheDocument();
+    expect(screen.getByText("general_settings.disable_env_credential_login: true")).toBeInTheDocument();
+  });
+
+  it("should warn an admin viewer too", () => {
+    mockRole("Admin Viewer");
+    mockDetails({ status: "healthy", show_env_credential_login_warning: true });
+    renderWithProviders(<EnvCredentialLoginWarningBanner accessToken="token" />);
+    expect(screen.getByRole("alert")).toBeInTheDocument();
+  });
+
+  it("should render nothing for a non-admin even when the proxy reports the warning", () => {
+    mockRole("Internal User");
+    mockDetails({ status: "healthy", show_env_credential_login_warning: true });
+    const { container } = renderWithProviders(<EnvCredentialLoginWarningBanner accessToken="token" />);
+    expect(container).toBeEmptyDOMElement();
+  });
+
+  it("should render nothing when env-credential login is disabled", () => {
+    mockRole("Admin");
+    mockDetails({ status: "healthy", show_env_credential_login_warning: false });
+    const { container } = renderWithProviders(<EnvCredentialLoginWarningBanner accessToken="token" />);
+    expect(container).toBeEmptyDOMElement();
+  });
+
+  it("should render nothing when readiness details are unavailable", () => {
+    mockRole("Admin");
+    mockDetails(undefined);
+    const { container } = renderWithProviders(<EnvCredentialLoginWarningBanner accessToken={null} />);
+    expect(container).toBeEmptyDOMElement();
+  });
+
+  it("should pass the access token to the readiness hook", () => {
+    mockRole("Admin");
+    mockDetails(undefined);
+    renderWithProviders(<EnvCredentialLoginWarningBanner accessToken="my-token" />);
+    expect(useHealthReadinessDetails).toHaveBeenCalledWith("my-token");
+  });
+});
diff --git a/ui/litellm-dashboard/src/components/EnvCredentialLoginWarningBanner.tsx b/ui/litellm-dashboard/src/components/EnvCredentialLoginWarningBanner.tsx
new file mode 100644
index 00000000000..3a9d50011f1
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/EnvCredentialLoginWarningBanner.tsx
@@ -0,0 +1,35 @@
+"use client";
+
+import React from "react";
+import { TriangleAlert } from "lucide-react";
+import { useHealthReadinessDetails } from "@/app/(dashboard)/hooks/healthReadiness/useHealthReadinessDetails";
+import { useAuth } from "@/contexts/AuthContext";
+import { isAdminRole } from "@/utils/roles";
+
+export const EnvCredentialLoginWarningBanner: React.FC<{ accessToken: string | null }> = ({ accessToken }) => {
+  const { userRole } = useAuth();
+  const { data: healthData } = useHealthReadinessDetails(accessToken);
+
+  if (!isAdminRole(userRole) || !healthData?.show_env_credential_login_warning) {
+    return null;
+  }
+
+  return (
+    <div
+      role="alert"
+      className="flex items-start gap-3 border-b border-destructive/40 bg-destructive/10 px-4 py-3 text-sm text-destructive"
+    >
+      <TriangleAlert className="mt-0.5 size-5 shrink-0" aria-hidden="true" />
+      <div>
+        <p className="font-semibold">Environment-credential login is enabled</p>
+        <p>
+          Anyone with <code className="font-mono">UI_USERNAME</code>/<code className="font-mono">UI_PASSWORD</code> (or
+          the master key, when <code className="font-mono">UI_PASSWORD</code> is unset) can sign in as a proxy admin
+          with a shared static secret. First create a regular admin account with its own password, then set{" "}
+          <code className="font-mono">general_settings.disable_env_credential_login: true</code> to turn this login path
+          off.
+        </p>
+      </div>
+    </div>
+  );
+};
diff --git a/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTable.test.tsx b/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTable.test.tsx
index 040fa463f9c..af3f98b746b 100644
--- a/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTable.test.tsx
+++ b/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTable.test.tsx
@@ -89,6 +89,65 @@ describe("PassThroughEndpointsTable", () => {
     expect(onDeleteClick).toHaveBeenCalledWith("ep-1");
   });
 
+  it("should disable edit and delete for config-defined endpoints", async () => {
+    const user = userEvent.setup();
+    const onEndpointClick = vi.fn();
+    const onDeleteClick = vi.fn();
+    const configEndpoint: passThroughItem = {
+      id: "ep-config",
+      path: "/from-config",
+      target: "https://config.example.com",
+      headers: {},
+      is_from_config: true,
+    };
+    render(
+      <PassThroughEndpointsTable
+        {...defaultProps}
+        endpoints={[configEndpoint]}
+        onEndpointClick={onEndpointClick}
+        onDeleteClick={onDeleteClick}
+      />,
+    );
+
+    await user.click(screen.getByTestId("endpoint-actions-ep-config"));
+    const editItem = await screen.findByTestId("endpoint-action-edit");
+    const deleteItem = await screen.findByTestId("endpoint-action-delete");
+
+    expect(editItem).toHaveAttribute("data-disabled");
+    expect(deleteItem).toHaveAttribute("data-disabled");
+    expect(screen.getByTestId("endpoint-config-hint")).toHaveTextContent(
+      "This endpoint is defined in the config file and cannot be edited or deleted on the dashboard.",
+    );
+
+    await user.click(editItem);
+    await user.click(deleteItem);
+
+    expect(onEndpointClick).not.toHaveBeenCalled();
+    expect(onDeleteClick).not.toHaveBeenCalled();
+  });
+
+  it("should not show the config hint for DB endpoints", async () => {
+    const user = userEvent.setup();
+    render(<PassThroughEndpointsTable {...defaultProps} />);
+
+    await user.click(screen.getByTestId("endpoint-actions-ep-1"));
+    await screen.findByTestId("endpoint-action-delete");
+    expect(screen.queryByTestId("endpoint-config-hint")).not.toBeInTheDocument();
+  });
+
+  it("should label endpoint source as Config or DB", () => {
+    const configEndpoint: passThroughItem = {
+      id: "ep-config",
+      path: "/from-config",
+      target: "https://config.example.com",
+      headers: {},
+      is_from_config: true,
+    };
+    render(<PassThroughEndpointsTable {...defaultProps} endpoints={[...endpoints, configEndpoint]} />);
+    expect(screen.getByText("Config")).toBeInTheDocument();
+    expect(screen.getAllByText("DB")).toHaveLength(2);
+  });
+
   it("should disable edit and delete for endpoints without an id", async () => {
     const user = userEvent.setup();
     const onEndpointClick = vi.fn();
diff --git a/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTableColumns.tsx b/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTableColumns.tsx
index d22b274861a..5b18685a140 100644
--- a/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTableColumns.tsx
+++ b/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughEndpointsTableColumns.tsx
@@ -18,6 +18,9 @@ import { cn } from "@/lib/cva.config";
 
 import type { passThroughItem } from "./PassThroughSettings";
 
+const CONFIG_ENDPOINT_HINT =
+  "This endpoint is defined in the config file and cannot be edited or deleted on the dashboard.";
+
 function HeaderWithTooltip({ title, tooltip }: { title: string; tooltip: string }) {
   return (
     <div className="flex items-center gap-1">
@@ -73,6 +76,7 @@ interface EndpointRowActionsProps {
 
 function EndpointRowActions({ endpoint, onEndpointClick, onDeleteClick }: EndpointRowActionsProps) {
   const endpointId = endpoint.id;
+  const isFromConfig = endpoint.is_from_config ?? false;
   return (
     <DropdownMenu>
       <DropdownMenuTrigger
@@ -85,8 +89,8 @@ function EndpointRowActions({ endpoint, onEndpointClick, onDeleteClick }: Endpoi
       <DropdownMenuContent align="end" className="w-52">
         <DropdownMenuItem
           data-testid="endpoint-action-edit"
-          disabled={!endpointId}
-          onClick={() => endpointId && onEndpointClick(endpointId)}
+          disabled={isFromConfig || !endpointId}
+          onClick={() => !isFromConfig && endpointId && onEndpointClick(endpointId)}
         >
           <Pencil />
           Edit
@@ -95,12 +99,17 @@ function EndpointRowActions({ endpoint, onEndpointClick, onDeleteClick }: Endpoi
         <DropdownMenuItem
           variant="destructive"
           data-testid="endpoint-action-delete"
-          disabled={!endpointId}
-          onClick={() => endpointId && onDeleteClick(endpointId)}
+          disabled={isFromConfig || !endpointId}
+          onClick={() => !isFromConfig && endpointId && onDeleteClick(endpointId)}
         >
           <Trash2 />
           Delete
         </DropdownMenuItem>
+        {isFromConfig && (
+          <div data-testid="endpoint-config-hint" className="px-2 py-1.5 text-xs text-muted-foreground">
+            {CONFIG_ENDPOINT_HINT}
+          </div>
+        )}
       </DropdownMenuContent>
     </DropdownMenu>
   );
@@ -124,7 +133,9 @@ export const getPassThroughEndpointsTableColumns = ({
     enableSorting: false,
     cell: ({ row }) => {
       const endpointId = row.original.id;
-      if (!endpointId) return <span className="font-mono text-xs text-muted-foreground">—</span>;
+      if (!endpointId || row.original.is_from_config) {
+        return <span className="font-mono text-xs text-muted-foreground">—</span>;
+      }
       return (
         <IdentityCell
           title={endpointId}
@@ -134,6 +145,17 @@ export const getPassThroughEndpointsTableColumns = ({
       );
     },
   },
+  {
+    id: "source",
+    meta: { title: "Source", skeleton: "badge" },
+    header: "Source",
+    size: 100,
+    enableSorting: false,
+    cell: ({ row }) => {
+      const isFromConfig = row.original.is_from_config ?? false;
+      return <StatusBadge tone={isFromConfig ? "neutral" : "info"} label={isFromConfig ? "Config" : "DB"} />;
+    },
+  },
   {
     id: "path",
     accessorKey: "path",
diff --git a/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughSettings.tsx b/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughSettings.tsx
index 2dc6fdbd32c..8ef2766d412 100644
--- a/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughSettings.tsx
+++ b/ui/litellm-dashboard/src/components/PassThroughSettings/PassThroughSettings.tsx
@@ -1,4 +1,13 @@
 import React, { useState, useEffect } from "react";
+import {
+  AlertDialog,
+  AlertDialogCancel,
+  AlertDialogContent,
+  AlertDialogDescription,
+  AlertDialogFooter,
+  AlertDialogHeader,
+  AlertDialogTitle,
+} from "@/components/ui/alert-dialog";
 import { Button } from "@/components/ui/button";
 import { deletePassThroughEndpointsCall, getPassThroughEndpointsCall } from "../networking";
 import AddPassThroughEndpoint from "../add_pass_through";
@@ -25,6 +34,7 @@ export interface passThroughItem {
   methods?: string[];
   guardrails?: Record<string, { request_fields?: string[]; response_fields?: string[] } | null>;
   default_query_params?: Record<string, string>;
+  is_from_config?: boolean;
 }
 
 const PassThroughSettings: React.FC<PassThroughSettingsProps> = ({ accessToken, userRole, userID, premiumUser }) => {
@@ -133,42 +143,22 @@ const PassThroughSettings: React.FC<PassThroughSettingsProps> = ({ accessToken,
         onDeleteClick={handleDelete}
       />
 
-      {isDeleteModalOpen && (
-        <div className="fixed z-overlay inset-0 overflow-y-auto">
-          <div className="flex items-end justify-center min-h-screen pt-4 px-4 pb-20 text-center sm:block sm:p-0">
-            <div className="fixed inset-0 transition-opacity" aria-hidden="true">
-              <div className="absolute inset-0 bg-gray-500 opacity-75"></div>
-            </div>
-
-            <span className="hidden sm:inline-block sm:align-middle sm:h-screen" aria-hidden="true">
-              &#8203;
-            </span>
-
-            <div className="inline-block align-bottom bg-card rounded-lg text-left overflow-hidden shadow-xl transform transition-all sm:my-8 sm:align-middle sm:max-w-lg sm:w-full">
-              <div className="bg-card px-4 pt-5 pb-4 sm:p-6 sm:pb-4">
-                <div className="sm:flex sm:items-start">
-                  <div className="mt-3 text-center sm:mt-0 sm:ml-4 sm:text-left">
-                    <h3 className="text-lg leading-6 font-medium text-foreground">Delete Pass-Through Endpoint</h3>
-                    <div className="mt-2">
-                      <p className="text-sm text-muted-foreground">
-                        Are you sure you want to delete this pass-through endpoint? This action cannot be undone.
-                      </p>
-                    </div>
-                  </div>
-                </div>
-              </div>
-              <div className="bg-muted px-4 py-3 sm:px-6 sm:flex sm:flex-row-reverse">
-                <Button variant="destructive" onClick={confirmDelete} className="ml-2">
-                  Delete
-                </Button>
-                <Button variant="outline" onClick={cancelDelete}>
-                  Cancel
-                </Button>
-              </div>
-            </div>
-          </div>
-        </div>
-      )}
+      <AlertDialog open={isDeleteModalOpen} onOpenChange={(open) => !open && cancelDelete()}>
+        <AlertDialogContent>
+          <AlertDialogHeader>
+            <AlertDialogTitle>Delete Pass-Through Endpoint</AlertDialogTitle>
+            <AlertDialogDescription>
+              Are you sure you want to delete this pass-through endpoint? This action cannot be undone.
+            </AlertDialogDescription>
+          </AlertDialogHeader>
+          <AlertDialogFooter>
+            <AlertDialogCancel>Cancel</AlertDialogCancel>
+            <Button variant="destructive" onClick={confirmDelete}>
+              Delete
+            </Button>
+          </AlertDialogFooter>
+        </AlertDialogContent>
+      </AlertDialog>
     </div>
   );
 };
diff --git a/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTable.test.tsx b/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTable.test.tsx
index 3ef7dee01b0..a4d76e2cc06 100644
--- a/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTable.test.tsx
+++ b/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTable.test.tsx
@@ -97,6 +97,24 @@ describe("LoggingCallbacksTable", () => {
     expect(onDelete).toHaveBeenCalledWith(callback);
   });
 
+  it("shows a read-only label instead of the actions menu for runtime-only callback rows", () => {
+    render(
+      <LoggingCallbacksTable
+        callbacks={[
+          { name: "langfuse", type: "success" as const, variables: baseVars },
+          { name: "datadog", type: "success" as const, variables: baseVars, read_only: true },
+        ]}
+        availableCallbacks={{}}
+        onTest={vi.fn()}
+        onEdit={vi.fn()}
+        onDelete={vi.fn()}
+      />,
+    );
+    expect(screen.getByTestId("callback-actions-langfuse-success")).toBeInTheDocument();
+    expect(screen.queryByTestId("callback-actions-datadog-success")).not.toBeInTheDocument();
+    expect(screen.getAllByText("Read only")).toHaveLength(1);
+  });
+
   // Regression: `/get_callbacks` returns the same `name` twice when a
   // callback is registered for both success and failure (e.g. `generic_api`
   // → POST to spend-log on both 200 and 4xx/5xx). The UI used to ignore
diff --git a/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTableColumns.tsx b/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTableColumns.tsx
index 2263fe03b3d..950ef5de6e4 100644
--- a/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTableColumns.tsx
+++ b/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/LoggingCallbacksTableColumns.tsx
@@ -50,6 +50,16 @@ interface CallbackRowActionsProps {
 }
 
 function CallbackRowActions({ callback, onTest, onEdit, onDelete }: CallbackRowActionsProps) {
+  if (callback.read_only) {
+    return (
+      <span
+        className="text-xs text-muted-foreground"
+        title="Active callback that was not added through the dashboard. Edit it where it was configured."
+      >
+        Read only
+      </span>
+    );
+  }
   return (
     <DropdownMenu>
       <DropdownMenuTrigger
diff --git a/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/types.ts b/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/types.ts
index 5d265f95484..ae446f1a042 100644
--- a/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/types.ts
+++ b/ui/litellm-dashboard/src/components/Settings/LoggingAndAlerts/LoggingCallbacks/types.ts
@@ -8,6 +8,7 @@ export interface AlertingObject {
   // every row to render as "Success".
   type?: "success" | "failure" | "success_and_failure";
   variables: AlertingVariables;
+  read_only?: boolean;
 }
 
 export interface AlertingVariables {
diff --git a/ui/litellm-dashboard/src/components/TeamSSOSettings.test.tsx b/ui/litellm-dashboard/src/components/TeamSSOSettings.test.tsx
index 7b3153f6e13..4a042c32cda 100644
--- a/ui/litellm-dashboard/src/components/TeamSSOSettings.test.tsx
+++ b/ui/litellm-dashboard/src/components/TeamSSOSettings.test.tsx
@@ -8,6 +8,19 @@ import { toast } from "@/lib/toast";
 
 vi.mock("./networking");
 
+vi.mock("@/app/(dashboard)/hooks/useAuthorized", () => ({
+  default: () => ({
+    token: "test-token",
+    accessToken: "test-token",
+    userId: "test-user",
+    userEmail: "test-user@example.com",
+    userRole: "Admin",
+    premiumUser: true,
+    disabledPersonalKeyCreation: null,
+    showSSOBanner: false,
+  }),
+}));
+
 vi.mock("./common_components/budget_duration_dropdown", () => {
   const BudgetDurationDropdown = ({ value, onChange }: { value: string | null; onChange: (value: string) => void }) => (
     <select
diff --git a/ui/litellm-dashboard/src/components/Teams.test.tsx b/ui/litellm-dashboard/src/components/Teams.test.tsx
index c7df35197e6..70c30596c75 100644
--- a/ui/litellm-dashboard/src/components/Teams.test.tsx
+++ b/ui/litellm-dashboard/src/components/Teams.test.tsx
@@ -33,6 +33,14 @@ vi.mock("./mcp_server_management/MCPServerSelector", () => ({
   ),
 }));
 
+vi.mock("./skills/SkillSelector", () => ({
+  default: ({ onChange }: { onChange: (selected: string[]) => void }) => (
+    <button type="button" data-testid="select-private-skill" onClick={() => onChange(["private-skill"])}>
+      Select private skill
+    </button>
+  ),
+}));
+
 const can = vi.fn();
 vi.mock("@/app/(dashboard)/hooks/useCan", () => ({
   default: (...args: unknown[]) => can(...args),
@@ -1359,6 +1367,27 @@ describe("Teams - the exact bytes the create call sends", () => {
     });
   });
 
+  it("puts the selected skills into object_permission.skills and drops the form key", async () => {
+    await openCreateModal();
+    await openSection("Skill Settings", /Allowed Skills/);
+    fireEvent.click(screen.getByTestId("select-private-skill"));
+
+    const payload = await submit();
+
+    expect(payload.object_permission).toStrictEqual({ skills: ["private-skill"] });
+    expect(payload).not.toHaveProperty("object_permission_skills");
+  });
+
+  it("sends no object_permission when Skill Settings is opened but nothing is selected", async () => {
+    await openCreateModal();
+    await openSection("Skill Settings", /Allowed Skills/);
+
+    const payload = await submit();
+
+    expect(payload).not.toHaveProperty("object_permission");
+    expect(payload).not.toHaveProperty("object_permission_skills");
+  });
+
   it("includes selected MCP toolsets in the create object permission", async () => {
     await openCreateModal();
     await openSection("MCP Settings", /Allowed MCP Servers/);
diff --git a/ui/litellm-dashboard/src/components/Teams.tsx b/ui/litellm-dashboard/src/components/Teams.tsx
index c4060163c78..d2d18139893 100644
--- a/ui/litellm-dashboard/src/components/Teams.tsx
+++ b/ui/litellm-dashboard/src/components/Teams.tsx
@@ -50,6 +50,7 @@ import { Organization, getDefaultTeamSettings, getGuardrailsList, getPoliciesLis
 import NumericalInput from "./shared/numerical_input";
 import VectorStoreSelector from "./vector_store_management/VectorStoreSelector";
 import SearchToolSelector from "./search_tools/SearchToolSelector";
+import SkillSelector from "./skills/SkillSelector";
 import { Dialog, DialogContent, DialogHeader, DialogTitle } from "@/components/ui/dialog";
 
 interface TeamProps {
@@ -99,6 +100,7 @@ const teamCreateFieldsSchema = z.object({
   mcp_tool_permissions: z.record(z.string(), z.array(z.string())).optional(),
   allowed_agents_and_groups: z.object({ agents: z.array(z.string()), accessGroups: z.array(z.string()) }).optional(),
   object_permission_search_tools: z.array(z.string()).optional(),
+  object_permission_skills: z.array(z.string()).optional(),
 });
 
 type TeamCreateFormValues = z.infer<typeof teamCreateFieldsSchema>;
@@ -128,6 +130,7 @@ const EMPTY_TEAM_CREATE_VALUES: TeamCreateFormValues = {
   mcp_tool_permissions: {},
   allowed_agents_and_groups: undefined,
   object_permission_search_tools: undefined,
+  object_permission_skills: undefined,
 };
 
 const ADDITIONAL_SETTINGS_FIELDS = [
@@ -147,6 +150,7 @@ const ADDITIONAL_SETTINGS_FIELDS = [
 const MCP_SETTINGS_FIELDS = ["allowed_mcp_servers_and_groups", "mcp_tool_permissions"] as const;
 const AGENT_SETTINGS_FIELDS = ["allowed_agents_and_groups"] as const;
 const SEARCH_TOOL_SETTINGS_FIELDS = ["object_permission_search_tools"] as const;
+const SKILL_SETTINGS_FIELDS = ["object_permission_skills"] as const;
 
 const isParsableJson = (value: string | undefined): boolean => {
   if (!value) {
@@ -214,6 +218,7 @@ const Teams: React.FC<TeamProps> = ({ accessToken, userID, userRole, premiumUser
   const [mcpSettingsOpen, setMcpSettingsOpen] = useState(false);
   const [agentSettingsOpen, setAgentSettingsOpen] = useState(false);
   const [searchToolSettingsOpen, setSearchToolSettingsOpen] = useState(false);
+  const [skillSettingsOpen, setSkillSettingsOpen] = useState(false);
 
   const adminOrgs = useMemo(
     () => getAdminOrganizations(userRole, userID, organizations),
@@ -505,6 +510,14 @@ const Teams: React.FC<TeamProps> = ({ accessToken, userID, userRole, premiumUser
           delete formValues.object_permission_search_tools;
         }
 
+        if (Array.isArray(formValues.object_permission_skills) && formValues.object_permission_skills.length > 0) {
+          if (!formValues.object_permission) {
+            formValues.object_permission = {};
+          }
+          formValues.object_permission.skills = formValues.object_permission_skills;
+        }
+        delete formValues.object_permission_skills;
+
         // Add model_aliases if any are defined
         if (Object.keys(modelAliases).length > 0) {
           formValues.model_aliases = modelAliases;
@@ -540,6 +553,7 @@ const Teams: React.FC<TeamProps> = ({ accessToken, userID, userRole, premiumUser
       ...(mcpSettingsOpen ? [] : MCP_SETTINGS_FIELDS),
       ...(agentSettingsOpen ? [] : AGENT_SETTINGS_FIELDS),
       ...(searchToolSettingsOpen ? [] : SEARCH_TOOL_SETTINGS_FIELDS),
+      ...(skillSettingsOpen ? [] : SKILL_SETTINGS_FIELDS),
     ]);
     return Object.fromEntries(Object.entries(values).filter(([key]) => !unmounted.has(key)));
   };
@@ -1163,6 +1177,38 @@ const Teams: React.FC<TeamProps> = ({ accessToken, userID, userRole, premiumUser
                     </CollapsibleContent>
                   </Collapsible>
 
+                  <Collapsible
+                    open={skillSettingsOpen}
+                    onOpenChange={setSkillSettingsOpen}
+                    className="mt-8 mb-8 overflow-hidden rounded-lg border"
+                  >
+                    <CollapsibleTrigger className="group/section flex w-full items-center justify-between px-4 py-3 text-left">
+                      <b>Skill Settings</b>
+                      <ChevronDown className="size-5 shrink-0 text-muted-foreground transition-transform group-data-[panel-open]/section:rotate-180" />
+                    </CollapsibleTrigger>
+                    <CollapsibleContent className="px-4 pb-3">
+                      <FormField
+                        control={form.control}
+                        name="object_permission_skills"
+                        className="mt-4"
+                        label={labelWithHint(
+                          "Allowed Skills",
+                          "Enabled skills are visible to every team. Grant disabled (private) Claude Code plugins to this team here.",
+                        )}
+                        description="Private skills keys on this team may see in the Claude Code marketplace."
+                      >
+                        {({ value, onChange }) => (
+                          <SkillSelector
+                            onChange={onChange}
+                            value={value}
+                            accessToken={accessToken || ""}
+                            placeholder="Select skills (optional)"
+                          />
+                        )}
+                      </FormField>
+                    </CollapsibleContent>
+                  </Collapsible>
+
                   <Collapsible className="mt-8 mb-8 overflow-hidden rounded-lg border">
                     <CollapsibleTrigger className="group/section flex w-full items-center justify-between px-4 py-3 text-left">
                       <b>Logging Settings</b>
diff --git a/ui/litellm-dashboard/src/components/VirtualKeysPage/VirtualKeysTable.test.tsx b/ui/litellm-dashboard/src/components/VirtualKeysPage/VirtualKeysTable.test.tsx
index 881b0b93ff9..c303dba697b 100644
--- a/ui/litellm-dashboard/src/components/VirtualKeysPage/VirtualKeysTable.test.tsx
+++ b/ui/litellm-dashboard/src/components/VirtualKeysPage/VirtualKeysTable.test.tsx
@@ -473,6 +473,92 @@ it("should display 'Default Proxy Admin' for user_id when value is 'default_user
   });
 });
 
+describe("entity links out of the key rows", () => {
+  const keyRow = async () => (await screen.findByText("Test Key Alias")).closest("tr") as HTMLElement;
+
+  const enableColumn = async (user: ReturnType<typeof userEvent.setup>, title: string) => {
+    await user.click(screen.getByRole("button", { name: "Columns" }));
+    await user.click(await screen.findByText(title));
+    await user.keyboard("{Escape}");
+  };
+
+  const enableCreatedByColumn = (user: ReturnType<typeof userEvent.setup>) => enableColumn(user, "Created By");
+
+  it("points the User and Team cells at their detail pages", async () => {
+    renderWithProviders(<VirtualKeysTable />);
+
+    const row = await keyRow();
+    expect(within(row).getByRole("link", { name: "user@example.com" })).toHaveAttribute(
+      "href",
+      "/ui/users?user=user-1",
+    );
+    expect(within(row).getByRole("link", { name: "Test Team" })).toHaveAttribute("href", "/ui/teams?team=team-1");
+  });
+
+  it("points the Organization cell at the org's detail page", async () => {
+    mockUseKeys.mockReturnValue(keysResult([{ ...mockKey, org_id: "org-1" }]));
+    const user = userEvent.setup();
+    renderWithProviders(<VirtualKeysTable />);
+    await enableColumn(user, "Organization");
+
+    const row = await keyRow();
+    expect(within(row).getByRole("link", { name: "Test Organization" })).toHaveAttribute(
+      "href",
+      "/ui/organizations?org=org-1",
+    );
+  });
+
+  it("points the Created By cell at the creator's detail page", async () => {
+    mockUseKeys.mockReturnValue(
+      keysResult([
+        {
+          ...mockKey,
+          created_by: "creator-1",
+          created_by_user: { user_id: "creator-1", user_email: "creator@example.com", user_alias: "The Creator" },
+        },
+      ]),
+    );
+    const user = userEvent.setup();
+    renderWithProviders(<VirtualKeysTable />);
+    await enableCreatedByColumn(user);
+
+    const row = await keyRow();
+    expect(within(row).getByRole("link", { name: "The Creator" })).toHaveAttribute("href", "/ui/users?user=creator-1");
+  });
+
+  it("leaves the default_user_id placeholder unlinked even once it resolves to a named user", async () => {
+    const placeholder = { user_id: "default_user_id", user_email: "admin@example.com", user_alias: "Proxy Admin" };
+    mockUseKeys.mockReturnValue(
+      keysResult([
+        {
+          ...mockKey,
+          user_id: placeholder.user_id,
+          user_email: placeholder.user_email,
+          user: placeholder,
+          created_by: placeholder.user_id,
+          created_by_user: placeholder,
+        },
+      ]),
+    );
+    const user = userEvent.setup();
+    renderWithProviders(<VirtualKeysTable />);
+    await enableCreatedByColumn(user);
+
+    const row = await keyRow();
+    expect(within(row).getAllByText("Proxy Admin")).toHaveLength(2);
+    expect(within(row).queryByRole("link", { name: "Proxy Admin" })).not.toBeInTheDocument();
+  });
+
+  it("leaves the litellm-dashboard session team unlinked", async () => {
+    mockUseKeys.mockReturnValue(keysResult([{ ...mockKey, team_id: "litellm-dashboard" }]));
+    renderWithProviders(<VirtualKeysTable />);
+
+    const row = await keyRow();
+    expect(within(row).getByText("litellm-dashboard")).toBeInTheDocument();
+    expect(within(row).queryByRole("link", { name: "litellm-dashboard" })).not.toBeInTheDocument();
+  });
+});
+
 it("should render table without crashing when models is null", async () => {
   mockUseKeys.mockReturnValue(keysResult([{ ...mockKey, models: null as unknown as string[] }]));
 
diff --git a/ui/litellm-dashboard/src/components/VirtualKeysPage/keyTableColumns.tsx b/ui/litellm-dashboard/src/components/VirtualKeysPage/keyTableColumns.tsx
index 0865fe76519..6eea77ae827 100644
--- a/ui/litellm-dashboard/src/components/VirtualKeysPage/keyTableColumns.tsx
+++ b/ui/litellm-dashboard/src/components/VirtualKeysPage/keyTableColumns.tsx
@@ -9,15 +9,17 @@ import { HoverCard, HoverCardContent, HoverCardTrigger } from "@/components/ui/h
 import { Skeleton } from "@/components/ui/skeleton";
 import {
   DateCell,
+  ENTITY_CELL_TITLE_CLASSES,
   IdCell,
   IdentityCell,
   ModelsCell,
   SpendBudgetCell,
   StatusBadge,
+  UserPopoverCell,
   type StatusTone,
 } from "@/components/shared/table_cells";
+import { orgDetailHref, teamDetailHref } from "@/utils/entityLinks";
 
-import DefaultProxyAdminTag from "../common_components/DefaultProxyAdminTag";
 import { KeyResponse, Team } from "../key_team_helpers/key_list";
 import { Organization } from "../networking";
 
@@ -62,67 +64,6 @@ const getKeyStatus = (key: KeyResponse): KeyStatus => {
   };
 };
 
-const UserPopoverCell = ({
-  userAlias,
-  userEmail,
-  userId,
-  width,
-}: {
-  userAlias: string | null;
-  userEmail: string | null;
-  userId: string | null;
-  width: number;
-}) => {
-  const displayValue = userAlias || userEmail || userId;
-  const isDefaultAdmin = userId === "default_user_id";
-
-  const popoverContent = (
-    <div className="flex flex-col gap-2 text-xs min-w-[200px] max-w-[300px]">
-      {[
-        { label: "User Alias", value: userAlias },
-        { label: "User Email", value: userEmail },
-        { label: "User ID", value: userId },
-      ].map(({ label, value }) => (
-        <div key={label} className="flex flex-col min-w-0">
-          <span className="text-muted-foreground">{label}</span>
-          {value ? (
-            <IdCell value={value} variant="plain" copyable className="max-w-full" />
-          ) : (
-            <span className="font-mono">-</span>
-          )}
-        </div>
-      ))}
-    </div>
-  );
-
-  if (isDefaultAdmin && !userAlias && !userEmail) {
-    return (
-      <HoverCard>
-        <HoverCardTrigger render={<span className="cursor-default" />}>
-          <DefaultProxyAdminTag userId={userId} />
-        </HoverCardTrigger>
-        <HoverCardContent align="start">{popoverContent}</HoverCardContent>
-      </HoverCard>
-    );
-  }
-
-  return (
-    <HoverCard>
-      <HoverCardTrigger
-        render={
-          <span
-            className="font-mono text-xs truncate block cursor-default"
-            style={{ maxWidth: width, overflow: "hidden" }}
-          />
-        }
-      >
-        {displayValue || "-"}
-      </HoverCardTrigger>
-      <HoverCardContent align="start">{popoverContent}</HoverCardContent>
-    </HoverCard>
-  );
-};
-
 const InfoHeader = ({ label, tooltip }: { label: string; tooltip: string }) => (
   <span className="flex items-center gap-1">
     {label}
@@ -201,12 +142,12 @@ export const getKeyTableColumns = ({
       const teamId = info.getValue() as string | null;
       if (!teamId) return "-";
       const team = allTeams.find((t) => t.team_id === teamId);
-      const displayValue = team?.team_alias || teamId;
-      const width = info.cell.column.getSize();
       return (
-        <span className="font-mono text-xs truncate block" style={{ maxWidth: width, overflow: "hidden" }}>
-          {displayValue}
-        </span>
+        <IdentityCell
+          title={team?.team_alias || teamId}
+          titleClassName={ENTITY_CELL_TITLE_CLASSES}
+          href={teamDetailHref(teamId)}
+        />
       );
     },
   },
@@ -221,12 +162,12 @@ export const getKeyTableColumns = ({
       const orgId = info.getValue() as string | null;
       if (!orgId) return "-";
       const org = organizations.find((o) => o.organization_id === orgId);
-      const displayValue = org?.organization_alias || orgId;
-      const width = info.cell.column.getSize();
       return (
-        <span className="font-mono text-xs truncate block" style={{ maxWidth: width, overflow: "hidden" }}>
-          {displayValue}
-        </span>
+        <IdentityCell
+          title={org?.organization_alias || orgId}
+          titleClassName={ENTITY_CELL_TITLE_CLASSES}
+          href={orgDetailHref(orgId)}
+        />
       );
     },
   },
diff --git a/ui/litellm-dashboard/src/components/add_model/add_auto_router_tab.test.tsx b/ui/litellm-dashboard/src/components/add_model/add_auto_router_tab.test.tsx
index 014854ac712..f6e619c5e84 100644
--- a/ui/litellm-dashboard/src/components/add_model/add_auto_router_tab.test.tsx
+++ b/ui/litellm-dashboard/src/components/add_model/add_auto_router_tab.test.tsx
@@ -1046,9 +1046,7 @@ describe("AddAutoRouterTab", () => {
       await waitFor(() => expect(handleAddAutoRouterSubmit).toHaveBeenCalled());
       expect(vi.mocked(handleAddAutoRouterSubmit).mock.calls.at(-1)?.[0]).toMatchObject({
         complexity_router_config: {
-          tier_model_configs: {
-            REASONING: [{ model_name: "claude-opus-5", litellm_params: { reasoning_effort: "high" } }],
-          },
+          tier_model_configs: ANTHROPIC_PRESET.complexity_router_config.tier_model_configs,
         },
       });
     });
diff --git a/ui/litellm-dashboard/src/components/callback_info_helpers.tsx b/ui/litellm-dashboard/src/components/callback_info_helpers.tsx
index dfa35de1b34..8e343e1a6e0 100644
--- a/ui/litellm-dashboard/src/components/callback_info_helpers.tsx
+++ b/ui/litellm-dashboard/src/components/callback_info_helpers.tsx
@@ -9,6 +9,7 @@ import langsmithLogo from "../../public/assets/logos/langsmith.png";
 import newrelicLogo from "../../public/assets/logos/newrelic.png";
 import openmeterLogo from "../../public/assets/logos/openmeter.png";
 import otelLogo from "../../public/assets/logos/otel.png";
+import pointfiveLogo from "../../public/assets/logos/pointfive.png";
 
 interface CallbackConfig {
   id: string;
@@ -162,6 +163,17 @@ export const CALLBACK_CONFIGS: CallbackConfig[] = [
     },
     description: "OpenTelemetry Logging Integration",
   },
+  {
+    id: "pointfive",
+    displayName: "PointFive",
+    logo: pointfiveLogo.src,
+    supports_key_team_logging: false,
+    dynamic_params: {
+      POINTFIVE_API_KEY: "password",
+      POINTFIVE_API_URL: "text",
+    },
+    description: "PointFive Logging Integration",
+  },
   {
     id: "s3",
     displayName: "S3",
diff --git a/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.test.tsx b/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.test.tsx
index f31e1839739..4ba6d8d50b4 100644
--- a/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.test.tsx
+++ b/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.test.tsx
@@ -51,4 +51,23 @@ describe("ResponseMetrics prompt cache chips", () => {
 
     expect(screen.queryByText(/Response Cache/)).not.toBeInTheDocument();
   });
+
+  it("does not render the Cost chip when a persisted cost is null", () => {
+    render(<ResponseMetrics usage={{ promptTokens: 1, cost: null as unknown as number }} />);
+
+    expect(screen.queryByText(/Cost:/)).not.toBeInTheDocument();
+    expect(screen.getByText("In: 1")).toBeInTheDocument();
+  });
+
+  it("does not render the Cost chip for NaN", () => {
+    render(<ResponseMetrics usage={{ ...baseUsage, cost: Number.NaN }} />);
+
+    expect(screen.queryByText(/Cost:/)).not.toBeInTheDocument();
+  });
+
+  it("renders the Cost chip for a finite cost", () => {
+    render(<ResponseMetrics usage={{ ...baseUsage, cost: 0.000063 }} />);
+
+    expect(screen.getByText("Cost: $0.000063")).toBeInTheDocument();
+  });
 });
diff --git a/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.tsx b/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.tsx
index ec62d0618d7..bb7debc7aee 100644
--- a/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.tsx
+++ b/ui/litellm-dashboard/src/components/chat_ui/ResponseMetrics.tsx
@@ -159,7 +159,7 @@ const ResponseMetrics: React.FC<ResponseMetricsProps> = ({ timeToFirstToken, tot
         />
       )}
 
-      {usage?.cost !== undefined && (
+      {typeof usage?.cost === "number" && Number.isFinite(usage.cost) && (
         <MetricItem
           label="Cost"
           tooltip="Cost"
diff --git a/ui/litellm-dashboard/src/components/chat_ui/mode_endpoint_mapping.tsx b/ui/litellm-dashboard/src/components/chat_ui/mode_endpoint_mapping.tsx
index 930ded5d1a5..b46200ccbf2 100644
--- a/ui/litellm-dashboard/src/components/chat_ui/mode_endpoint_mapping.tsx
+++ b/ui/litellm-dashboard/src/components/chat_ui/mode_endpoint_mapping.tsx
@@ -57,3 +57,20 @@ export const getEndpointType = (mode: string): EndpointType => {
   // else default to chat
   return EndpointType.CHAT;
 };
+
+export const isModeCompatibleWithEndpoint = (mode: string | null | undefined, endpointType: EndpointType): boolean => {
+  if (!mode) return true;
+  if (!Object.values(ModelMode).includes(mode as ModelMode)) return false;
+  const optionEndpoint = getEndpointType(mode);
+  if (
+    endpointType === EndpointType.RESPONSES ||
+    endpointType === EndpointType.ANTHROPIC_MESSAGES ||
+    endpointType === EndpointType.INTERACTIONS
+  ) {
+    return optionEndpoint === endpointType || optionEndpoint === EndpointType.CHAT;
+  }
+  if (endpointType === EndpointType.IMAGE_EDITS) {
+    return optionEndpoint === endpointType || optionEndpoint === EndpointType.IMAGE;
+  }
+  return optionEndpoint === endpointType;
+};
diff --git a/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.test.ts b/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.test.ts
index 1d07ca09df5..4713fcbc55b 100644
--- a/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.test.ts
+++ b/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.test.ts
@@ -17,6 +17,7 @@ import {
   formatKeywords,
   parseSkillSource,
   isValidSubPath,
+  isValidSha256,
   buildMarketplaceSettingsSnippet,
 } from "./helpers";
 import { MarketplacePluginEntry } from "./types";
@@ -114,6 +115,12 @@ describe("getSourceDisplayText", () => {
     );
   });
 
+  it("shows the archive url for an archive source", () => {
+    expect(getSourceDisplayText({ source: "archive", url: "https://bucket.s3.amazonaws.com/skill.zip" })).toBe(
+      "https://bucket.s3.amazonaws.com/skill.zip",
+    );
+  });
+
   it("returns unknown for missing data", () => {
     expect(getSourceDisplayText({ source: "github" })).toBe("Unknown source");
   });
@@ -140,6 +147,12 @@ describe("getSourceLink", () => {
     );
   });
 
+  it("returns the archive url for an archive source", () => {
+    expect(getSourceLink({ source: "archive", url: "https://bucket.s3.amazonaws.com/skill.zip" })).toBe(
+      "https://bucket.s3.amazonaws.com/skill.zip",
+    );
+  });
+
   it("returns null when no repo or url", () => {
     expect(getSourceLink({ source: "github" })).toBeNull();
   });
@@ -329,6 +342,20 @@ describe("isValidUrl", () => {
   });
 });
 
+describe("isValidSha256", () => {
+  it("accepts an empty digest and a 64-character hex digest in either case", () => {
+    expect(isValidSha256("")).toBe(true);
+    expect(isValidSha256("a".repeat(64))).toBe(true);
+    expect(isValidSha256(" " + "ABCDEF0123456789".repeat(4) + " ")).toBe(true);
+  });
+
+  it("rejects wrong length and non-hex digests", () => {
+    expect(isValidSha256("a".repeat(63))).toBe(false);
+    expect(isValidSha256("a".repeat(65))).toBe(false);
+    expect(isValidSha256("g".repeat(64))).toBe(false);
+  });
+});
+
 describe("parseKeywords", () => {
   it("splits comma-separated keywords", () => {
     expect(parseKeywords("a, b, c")).toEqual(["a", "b", "c"]);
@@ -445,6 +472,39 @@ describe("parseSkillSource", () => {
     expect(parseSkillSource("not a url")).toBeNull();
   });
 
+  it("parses an S3 zip URL into an archive source and names the skill after the file", () => {
+    expect(parseSkillSource("https://skills-bucket.s3.us-east-1.amazonaws.com/plugins/My_Skill-1.0.0.zip")).toEqual({
+      parsed: { source: "archive", url: "https://skills-bucket.s3.us-east-1.amazonaws.com/plugins/My_Skill-1.0.0.zip" },
+      label: "Zip archive — skills-bucket.s3.us-east-1.amazonaws.com/plugins/My_Skill-1.0.0.zip",
+      suggestedName: "my-skill-1-0-0",
+    });
+  });
+
+  it("keeps the query string of a zip URL so versioned or signed object links still resolve", () => {
+    expect(parseSkillSource("https://bucket.s3.amazonaws.com/skill.ZIP?versionId=abc")?.parsed).toEqual({
+      source: "archive",
+      url: "https://bucket.s3.amazonaws.com/skill.ZIP?versionId=abc",
+    });
+  });
+
+  it("ignores the subfolder for a zip URL since the archive is installed whole", () => {
+    expect(parseSkillSource("https://artifacts.example.com/skill.zip", "plugins/x")?.parsed).toEqual({
+      source: "archive",
+      url: "https://artifacts.example.com/skill.zip",
+    });
+  });
+
+  it("rejects a plain http zip URL", () => {
+    expect(parseSkillSource("http://artifacts.example.com/skill.zip")).toBeNull();
+  });
+
+  it("treats a github zip download URL as an archive rather than a repo path", () => {
+    expect(parseSkillSource("https://github.com/org/repo/releases/download/v1/skill.zip")?.parsed).toEqual({
+      source: "archive",
+      url: "https://github.com/org/repo/releases/download/v1/skill.zip",
+    });
+  });
+
   it("suggests a kebab-friendly name from the last path segment", () => {
     expect(parseSkillSource("github.com/org/my-awesome-skill")?.suggestedName).toBe("my-awesome-skill");
     expect(parseSkillSource("github.com/org/repo/tree/main/plugins/cool-skill")?.suggestedName).toBe("cool-skill");
diff --git a/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.ts b/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.ts
index 5b3d4f20c1e..6f673d67f87 100644
--- a/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.ts
+++ b/ui/litellm-dashboard/src/components/claude_code_plugins/helpers.ts
@@ -23,6 +23,12 @@ const GITHUB_HOST = "github.com";
 
 const SKILL_FILE_EXTENSION_REGEX = /\.(md|markdown|txt|json|ya?ml|toml)$/i;
 
+const ZIP_ARCHIVE_REGEX = /\.zip$/i;
+
+export const SHA256_REGEX = /^[0-9a-fA-F]{64}$/;
+
+export const isValidSha256 = (digest: string): boolean => digest.trim() === "" || SHA256_REGEX.test(digest.trim());
+
 // WHATWG normalizes obfuscated IPv4 (e.g. 2130706433, 0x7f.0.0.1) to dotted-decimal, so this
 // catches every IPv4 form; bracketed IPv6 is rejected separately.
 const IPV4_HOST_REGEX = /^\d{1,3}(\.\d{1,3}){3}$/;
@@ -160,16 +166,26 @@ const parseRawGitSource = (url: URL, subPath?: string): SkillSourcePreview | nul
   };
 };
 
+const parseArchiveSource = (url: URL): SkillSourcePreview => ({
+  parsed: { source: "archive", url: url.href },
+  label: `Zip archive — ${url.host}${url.pathname}`,
+  suggestedName: toKebabCase(lastSegment(url.pathname).replace(ZIP_ARCHIVE_REGEX, "")),
+});
+
 /**
- * Parse any git-accessible repository URL into a registerable skill source.
- * GitHub URLs keep their `github`/`git-subdir` shorthand; every other host is
- * treated as a raw repo URL, with an optional subfolder turning it into git-subdir.
+ * Parse any git-accessible repository URL or https zip archive URL into a registerable skill
+ * source. A `.zip` path is an `archive` source (S3, Artifactory, any static host). GitHub URLs
+ * keep their `github`/`git-subdir` shorthand; every other host is treated as a raw repo URL,
+ * with an optional subfolder turning it into git-subdir.
  */
 export const parseSkillSource = (rawUrl: string, subPath?: string): SkillSourcePreview | null => {
   const url = parseRepoUrl(rawUrl);
   if (!url) {
     return null;
   }
+  if (ZIP_ARCHIVE_REGEX.test(url.pathname)) {
+    return parseArchiveSource(url);
+  }
   if (url.hostname.replace(/^www\./, "") === GITHUB_HOST) {
     return parseGitHubSource(url, subPath);
   }
@@ -245,7 +261,7 @@ export const getSourceDisplayText = (source: PluginSource): string => {
   if (source.source === "git-subdir" && source.url && source.path) {
     return `${source.url} @ ${source.path}`;
   }
-  if (source.source === "url" && source.url) {
+  if ((source.source === "url" || source.source === "archive") && source.url) {
     return source.url;
   }
   return "Unknown source";
@@ -258,10 +274,8 @@ export const getSourceLink = (source: PluginSource): string | null => {
   if (source.source === "github" && source.repo) {
     return `https://github.com/${source.repo}`;
   }
-  if ((source.source === "url" || source.source === "git-subdir") && source.url) {
-    return source.url;
-  }
-  return null;
+  const linksToUrl = source.source === "url" || source.source === "git-subdir" || source.source === "archive";
+  return linksToUrl && source.url ? source.url : null;
 };
 
 /**
diff --git a/ui/litellm-dashboard/src/components/claude_code_plugins/skill_detail.tsx b/ui/litellm-dashboard/src/components/claude_code_plugins/skill_detail.tsx
index 7cbbb08b623..b37204c6073 100644
--- a/ui/litellm-dashboard/src/components/claude_code_plugins/skill_detail.tsx
+++ b/ui/litellm-dashboard/src/components/claude_code_plugins/skill_detail.tsx
@@ -26,7 +26,7 @@ const SkillDetail: React.FC<SkillDetailProps> = ({ skill, onBack }) => {
     const src = skill.source;
     if (src.source === "github" && src.repo) return `https://github.com/${src.repo}`;
     if (src.source === "git-subdir" && src.url) return src.path ? `${src.url}/tree/main/${src.path}` : src.url;
-    if (src.source === "url" && src.url) return src.url;
+    if ((src.source === "url" || src.source === "archive") && src.url) return src.url;
     return null;
   })();
 
diff --git a/ui/litellm-dashboard/src/components/claude_code_plugins/types.ts b/ui/litellm-dashboard/src/components/claude_code_plugins/types.ts
index d16c880749b..98f80fd2959 100644
--- a/ui/litellm-dashboard/src/components/claude_code_plugins/types.ts
+++ b/ui/litellm-dashboard/src/components/claude_code_plugins/types.ts
@@ -8,10 +8,11 @@ import type { components } from "@/lib/http/schema";
 // Kept hand-written: the backend types `source` as Dict[str, str], so the generated type is a
 // loose string map; this discriminant union is what the parser and display helpers rely on.
 export interface PluginSource {
-  source: "github" | "url" | "git-subdir";
+  source: "github" | "url" | "git-subdir" | "archive";
   repo?: string; // Format: "org/repo" for GitHub
   url?: string; // Full URL for other sources
   path?: string; // Subdirectory path for git-subdir
+  sha256?: string;
 }
 
 export type PluginAuthor = components["schemas"]["PluginAuthor"];
diff --git a/ui/litellm-dashboard/src/components/common_components/DefaultProxyAdminTag.tsx b/ui/litellm-dashboard/src/components/common_components/DefaultProxyAdminTag.tsx
index 9ec24bb929b..308f722a8f2 100644
--- a/ui/litellm-dashboard/src/components/common_components/DefaultProxyAdminTag.tsx
+++ b/ui/litellm-dashboard/src/components/common_components/DefaultProxyAdminTag.tsx
@@ -1,13 +1,12 @@
 import { Badge } from "@/components/ui/badge";
-
-const DEFAULT_USER_ID = "default_user_id";
+import { DEFAULT_PROXY_ADMIN_USER_ID } from "@/utils/sentinels";
 
 interface DefaultProxyAdminTagProps {
   userId: string | null | undefined;
 }
 
 export default function DefaultProxyAdminTag({ userId }: DefaultProxyAdminTagProps) {
-  if (userId === DEFAULT_USER_ID) {
+  if (userId === DEFAULT_PROXY_ADMIN_USER_ID) {
     return <Badge variant="secondary">Default Proxy Admin</Badge>;
   }
 
diff --git a/ui/litellm-dashboard/src/components/common_components/LabeledField.tsx b/ui/litellm-dashboard/src/components/common_components/LabeledField.tsx
index 9f45b05f306..99046cfa84d 100644
--- a/ui/litellm-dashboard/src/components/common_components/LabeledField.tsx
+++ b/ui/litellm-dashboard/src/components/common_components/LabeledField.tsx
@@ -2,6 +2,7 @@ import React from "react";
 import CopyButton from "@/components/shared/CopyButton";
 import { EntityLink } from "@/components/shared/EntityLink";
 import { cx } from "@/lib/cva.config";
+import { DEFAULT_PROXY_ADMIN_USER_ID } from "@/utils/sentinels";
 import DefaultProxyAdminTag from "./DefaultProxyAdminTag";
 
 interface LabeledFieldProps {
@@ -24,7 +25,7 @@ export default function LabeledField({
   defaultUserIdCheck = false,
 }: LabeledFieldProps) {
   const isEmpty = !value;
-  const isDefaultUser = defaultUserIdCheck && value === "default_user_id";
+  const isDefaultUser = defaultUserIdCheck && value === DEFAULT_PROXY_ADMIN_USER_ID;
   const displayValue = isEmpty ? "-" : value;
   const isCopyable = copyable && !isEmpty && !isDefaultUser;
   const isLink = href != null && !isEmpty && !isDefaultUser;
diff --git a/ui/litellm-dashboard/src/components/llm_calls/chat_completion.test.tsx b/ui/litellm-dashboard/src/components/llm_calls/chat_completion.test.tsx
index 08b02cacb21..ec477441586 100644
--- a/ui/litellm-dashboard/src/components/llm_calls/chat_completion.test.tsx
+++ b/ui/litellm-dashboard/src/components/llm_calls/chat_completion.test.tsx
@@ -468,6 +468,18 @@ describe("chat_completion prompt cache usage", () => {
     expect(usageData).not.toHaveProperty("cacheReadTokens");
     expect(usageData).not.toHaveProperty("cacheCreationTokens");
   });
+
+  it("omits cost when the provider reports a non-numeric value", async () => {
+    const usageData = await captureUsage({ cost: "not-a-number" });
+
+    expect(usageData).toEqual(expect.not.objectContaining({ cost: expect.anything() }));
+  });
+
+  it("omits cost when the provider reports a blank value", async () => {
+    const usageData = await captureUsage({ cost: "  " });
+
+    expect(usageData).toEqual(expect.not.objectContaining({ cost: expect.anything() }));
+  });
 });
 
 describe("chat_completion response cache", () => {
diff --git a/ui/litellm-dashboard/src/components/llm_calls/chat_completion.tsx b/ui/litellm-dashboard/src/components/llm_calls/chat_completion.tsx
index cd0852bc06e..ffa2877fbd9 100644
--- a/ui/litellm-dashboard/src/components/llm_calls/chat_completion.tsx
+++ b/ui/litellm-dashboard/src/components/llm_calls/chat_completion.tsx
@@ -5,6 +5,7 @@ import { VectorStoreSearchResponse } from "../chat_ui/types";
 import { getProxyBaseUrl } from "@/components/networking";
 import { MCPServer, MCPToolset, type MCPEvent } from "@/components/mcp_tools/types";
 import { extractPromptCacheTokens } from "@/utils/promptCacheUsage";
+import { parseUsageCost } from "./usage_cost";
 
 const completionAsSingleChunk = (completion: ChatCompletion): ChatCompletionChunk =>
   ({
@@ -243,9 +244,9 @@ export async function makeOpenAIChatCompletionRequest(
           usageData.reasoningTokens = chunkWithUsage.usage.completion_tokens_details.reasoning_tokens;
         }
 
-        // Extract cost from usage object if available
-        if (chunkWithUsage.usage.cost !== undefined && chunkWithUsage.usage.cost !== null) {
-          usageData.cost = parseFloat(chunkWithUsage.usage.cost);
+        const parsedCost = parseUsageCost(chunkWithUsage.usage.cost);
+        if (parsedCost !== undefined) {
+          usageData.cost = parsedCost;
         }
 
         onUsageData(usageData);
diff --git a/ui/litellm-dashboard/src/components/llm_calls/responses_api.test.tsx b/ui/litellm-dashboard/src/components/llm_calls/responses_api.test.tsx
index ae5e224cfbf..290c8b0b619 100644
--- a/ui/litellm-dashboard/src/components/llm_calls/responses_api.test.tsx
+++ b/ui/litellm-dashboard/src/components/llm_calls/responses_api.test.tsx
@@ -233,6 +233,64 @@ describe("responses_api", () => {
     expect(onUsageData).toHaveBeenCalledWith(expect.not.objectContaining({ cost: expect.anything() }), "");
   });
 
+  it("should omit cost when the proxy reports a non-numeric cost", async () => {
+    async function* streamWithNonNumericCost() {
+      yield {
+        type: "response.completed",
+        response: {
+          id: "resp_non_numeric_cost",
+          usage: { output_tokens: 12, input_tokens: 12, total_tokens: 24, cost: "not-a-number" },
+        },
+      };
+    }
+    mockResponsesCreate.mockResolvedValueOnce(streamWithNonNumericCost());
+
+    const onUsageData = vi.fn();
+
+    await makeOpenAIResponsesRequest(
+      messages,
+      mockUpdateTextUI,
+      "gpt-4",
+      "test-token",
+      undefined,
+      undefined,
+      undefined,
+      undefined,
+      onUsageData,
+    );
+
+    expect(onUsageData).toHaveBeenCalledWith(expect.not.objectContaining({ cost: expect.anything() }), "");
+  });
+
+  it("should omit cost when the proxy reports a blank cost", async () => {
+    async function* streamWithBlankCost() {
+      yield {
+        type: "response.completed",
+        response: {
+          id: "resp_blank_cost",
+          usage: { output_tokens: 12, input_tokens: 12, total_tokens: 24, cost: "  " },
+        },
+      };
+    }
+    mockResponsesCreate.mockResolvedValueOnce(streamWithBlankCost());
+
+    const onUsageData = vi.fn();
+
+    await makeOpenAIResponsesRequest(
+      messages,
+      mockUpdateTextUI,
+      "gpt-4",
+      "test-token",
+      undefined,
+      undefined,
+      undefined,
+      undefined,
+      onUsageData,
+    );
+
+    expect(onUsageData).toHaveBeenCalledWith(expect.not.objectContaining({ cost: expect.anything() }), "");
+  });
+
   it("should replay MCP output items as events for a non-streaming response", async () => {
     mockResponsesCreate.mockReturnValueOnce(
       nonStreamingResponse({
diff --git a/ui/litellm-dashboard/src/components/llm_calls/responses_api.tsx b/ui/litellm-dashboard/src/components/llm_calls/responses_api.tsx
index 7ab76488504..ce54c7c6b40 100644
--- a/ui/litellm-dashboard/src/components/llm_calls/responses_api.tsx
+++ b/ui/litellm-dashboard/src/components/llm_calls/responses_api.tsx
@@ -4,6 +4,7 @@ import { TokenUsage } from "../chat_ui/ResponseMetrics";
 import { getProxyBaseUrl } from "@/components/networking";
 import { toast } from "@/lib/toast";
 import { extractPromptCacheTokens } from "@/utils/promptCacheUsage";
+import { parseUsageCost } from "./usage_cost";
 import type { MCPEvent } from "@/components/mcp_tools/types";
 import { MCPServer, MCPToolset } from "@/components/mcp_tools/types";
 import {
@@ -311,8 +312,9 @@ export async function makeOpenAIResponsesRequest(
               usageData.reasoningTokens = reasoningTokens;
             }
 
-            if (usage.cost !== undefined && usage.cost !== null) {
-              usageData.cost = Number(usage.cost);
+            const parsedCost = parseUsageCost(usage.cost);
+            if (parsedCost !== undefined) {
+              usageData.cost = parsedCost;
             }
 
             onUsageData(usageData, mcpToolUsed);
diff --git a/ui/litellm-dashboard/src/components/llm_calls/usage_cost.test.ts b/ui/litellm-dashboard/src/components/llm_calls/usage_cost.test.ts
new file mode 100644
index 00000000000..ee1021c0629
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/llm_calls/usage_cost.test.ts
@@ -0,0 +1,39 @@
+import { describe, expect, it } from "vitest";
+import { parseUsageCost } from "./usage_cost";
+
+describe("parseUsageCost", () => {
+  it("keeps finite numbers, including zero", () => {
+    expect(parseUsageCost(0)).toBe(0);
+    expect(parseUsageCost(0.000063)).toBe(0.000063);
+  });
+
+  it("keeps numeric strings", () => {
+    expect(parseUsageCost("0.00019")).toBe(0.00019);
+    expect(parseUsageCost(" 0.00019 ")).toBe(0.00019);
+  });
+
+  it("drops blank strings instead of fabricating a zero cost", () => {
+    expect(parseUsageCost("")).toBeUndefined();
+    expect(parseUsageCost("   ")).toBeUndefined();
+    expect(parseUsageCost("\t\n")).toBeUndefined();
+  });
+
+  it("drops strings with a numeric prefix instead of truncating them", () => {
+    expect(parseUsageCost("1oops")).toBeUndefined();
+    expect(parseUsageCost("0.5 USD")).toBeUndefined();
+  });
+
+  it("drops non-finite numbers", () => {
+    expect(parseUsageCost(Number.NaN)).toBeUndefined();
+    expect(parseUsageCost(Number.POSITIVE_INFINITY)).toBeUndefined();
+  });
+
+  it("drops values that are not numbers or strings", () => {
+    expect(parseUsageCost(null)).toBeUndefined();
+    expect(parseUsageCost(undefined)).toBeUndefined();
+    expect(parseUsageCost(true)).toBeUndefined();
+    expect(parseUsageCost([])).toBeUndefined();
+    expect(parseUsageCost(["0.5"])).toBeUndefined();
+    expect(parseUsageCost({ total_cost: 0.5 })).toBeUndefined();
+  });
+});
diff --git a/ui/litellm-dashboard/src/components/llm_calls/usage_cost.ts b/ui/litellm-dashboard/src/components/llm_calls/usage_cost.ts
new file mode 100644
index 00000000000..79f56dcb2df
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/llm_calls/usage_cost.ts
@@ -0,0 +1,23 @@
+/**
+ * Providers and upstream gateways report `usage.cost` unvalidated: it arrives as a number, a numeric
+ * string, an empty string, or something non-numeric. A cost that does not resolve to a finite number
+ * must be dropped rather than coerced, because `NaN` survives `JSON.stringify` as `null` and crashes
+ * the metrics row on the next load.
+ */
+export function parseUsageCost(rawCost: unknown): number | undefined {
+  if (typeof rawCost === "number") {
+    return Number.isFinite(rawCost) ? rawCost : undefined;
+  }
+
+  if (typeof rawCost !== "string") {
+    return undefined;
+  }
+
+  const trimmed = rawCost.trim();
+  if (trimmed === "") {
+    return undefined;
+  }
+
+  const parsed = Number(trimmed);
+  return Number.isFinite(parsed) ? parsed : undefined;
+}
diff --git a/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.test.tsx b/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.integration.test.tsx
similarity index 61%
rename from ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.test.tsx
rename to ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.integration.test.tsx
index d6e614da5eb..b1174d1d37d 100644
--- a/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.test.tsx
+++ b/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.integration.test.tsx
@@ -1,5 +1,5 @@
 import React from "react";
-import { render, screen } from "@testing-library/react";
+import { fireEvent, render, screen } from "@testing-library/react";
 import userEvent from "@testing-library/user-event";
 import { describe, it, expect } from "vitest";
 import MCPToolArgumentsForm, { MCPToolArgumentsFormRef } from "./MCPToolArgumentsForm";
@@ -26,6 +26,118 @@ const submitError = async (ref: React.RefObject<MCPToolArgumentsFormRef | null>)
 };
 
 describe("MCPToolArgumentsForm", () => {
+  it("keeps dotted arguments separate from a same-prefix object and converts their values", async () => {
+    const ref = renderForm({
+      type: "object",
+      properties: {
+        "filter.category": { type: "string" },
+        filter: { type: "object" },
+        "page.limit": { type: "integer" },
+        query: { type: "string" },
+      },
+      required: ["filter.category"],
+    });
+
+    fireEvent.change(screen.getByRole("textbox", { name: "filter.category *" }), {
+      target: { value: "invoices" },
+    });
+    fireEvent.change(screen.getByRole("textbox", { name: "filter" }), {
+      target: { value: '{"category":"receipts","metadata":{"region":"eu"}}' },
+    });
+    fireEvent.change(screen.getByRole("spinbutton", { name: "page.limit" }), { target: { value: "7" } });
+    fireEvent.change(screen.getByRole("textbox", { name: "query" }), { target: { value: "September" } });
+
+    const expected = {
+      "filter.category": "invoices",
+      filter: { category: "receipts", metadata: { region: "eu" } },
+      "page.limit": 7,
+      query: "September",
+    };
+    await expect(submit(ref)).resolves.toEqual(expected);
+  });
+
+  it("shows required validation on the literal dotted field and accepts a correction", async () => {
+    const ref = renderForm({
+      type: "object",
+      properties: { "filter.category": { type: "string" } },
+      required: ["filter.category"],
+    });
+
+    expect(await submitError(ref)).toEqual({
+      errorFields: [{ name: ["filter.category"], errors: ["Please enter filter.category"] }],
+    });
+    expect(await screen.findByText("Please enter filter.category")).toBeInTheDocument();
+    expect(screen.getByRole("textbox", { name: "filter.category *" })).toHaveAttribute("aria-invalid", "true");
+
+    fireEvent.change(screen.getByRole("textbox", { name: "filter.category *" }), {
+      target: { value: "invoices" },
+    });
+    await expect(submit(ref)).resolves.toEqual({ "filter.category": "invoices" });
+  });
+
+  it("validates JSON for dotted arguments inside params and preserves their literal names", async () => {
+    const ref = renderForm({
+      type: "object",
+      properties: {
+        params: {
+          type: "object",
+          properties: { "filter.options": { type: "object" } },
+          required: ["filter.options"],
+        },
+      },
+      required: [],
+    });
+    const field = screen.getByRole("textbox", { name: "filter.options *" });
+    fireEvent.change(field, { target: { value: "invalid" } });
+
+    expect(await submitError(ref)).toEqual({
+      errorFields: [{ name: ["filter.options"], errors: ["Invalid JSON"] }],
+    });
+    expect(await screen.findByText("Invalid JSON")).toBeInTheDocument();
+
+    fireEvent.change(field, { target: { value: '{"region":"eu"}' } });
+    await expect(submit(ref)).resolves.toEqual({ params: { "filter.options": { region: "eu" } } });
+  });
+
+  it("resets dotted defaults and positional values when the selected tool changes", async () => {
+    const ref = React.createRef<MCPToolArgumentsFormRef>();
+    const { rerender } = render(
+      <MCPToolArgumentsForm
+        ref={ref}
+        tool={toolWith({
+          type: "object",
+          properties: { "filter.category": { type: "string", default: "invoices" } },
+          required: [],
+        })}
+      />,
+    );
+    expect(screen.getByRole("textbox", { name: "filter.category" })).toHaveValue("invoices");
+    await expect(submit(ref)).resolves.toEqual({ "filter.category": "invoices" });
+    fireEvent.change(screen.getByRole("textbox", { name: "filter.category" }), {
+      target: { value: "edited" },
+    });
+    await expect(submit(ref)).resolves.toEqual({ "filter.category": "edited" });
+
+    rerender(
+      <MCPToolArgumentsForm
+        ref={ref}
+        tool={{
+          ...toolWith({
+            type: "object",
+            properties: {
+              query: { type: "string", default: "new tool" },
+              "filter.category": { type: "string", default: "receipts" },
+            },
+            required: [],
+          }),
+          name: "another_tool",
+        }}
+      />,
+    );
+    expect(screen.getByRole("textbox", { name: "filter.category" })).toHaveValue("receipts");
+    await expect(submit(ref)).resolves.toEqual({ query: "new tool", "filter.category": "receipts" });
+  });
+
   it("returns typed values for a string, integer, number and boolean field", async () => {
     const user = userEvent.setup();
     const ref = renderForm({
diff --git a/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.tsx b/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.tsx
index ca8c5697e6e..ab3213d9b37 100644
--- a/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.tsx
+++ b/ui/litellm-dashboard/src/components/mcp_tools/MCPToolArgumentsForm.tsx
@@ -1,6 +1,6 @@
 import React, { forwardRef, useImperativeHandle, useMemo } from "react";
 import { CircleHelp } from "lucide-react";
-import { useForm, type Resolver } from "react-hook-form";
+import { useForm, type Resolver, type ResolverResult } from "react-hook-form";
 import { FieldGroup } from "@/components/ui/field";
 import { FormField } from "@/components/shared/form/FormField";
 import { Input } from "@/components/ui/input";
@@ -9,7 +9,10 @@ import { Textarea } from "@/components/ui/textarea";
 import { Tooltip, TooltipContent, TooltipProvider, TooltipTrigger } from "@/components/ui/tooltip";
 import { MCPTool, InputSchema, InputSchemaProperty } from "./types";
 
-type ToolFormValues = Record<string, unknown>;
+type ToolFormValues = { args: unknown[] };
+
+const argumentValues = (schema: InputSchema, values: ToolFormValues): Record<string, unknown> =>
+  Object.fromEntries(Object.keys(schema.properties ?? {}).map((key, index) => [key, values.args[index]]));
 
 const STRING_SCHEMA_MESSAGES: Readonly<Record<string, string>> = { input: "Please enter input for this tool" };
 
@@ -38,7 +41,7 @@ type FieldError = { type: string; message: string };
 const collectErrors = (
   actualSchema: InputSchema,
   requiredMessages: Readonly<Record<string, string>>,
-  values: ToolFormValues,
+  values: Record<string, unknown>,
 ): Record<string, FieldError> => {
   const entries = Object.entries(actualSchema.properties ?? {}).flatMap<[string, FieldError]>(([key, prop]) => {
     const value = values[key];
@@ -56,9 +59,19 @@ const collectErrors = (
 
 const buildResolver =
   (actualSchema: InputSchema, requiredMessages: Readonly<Record<string, string>> = {}): Resolver<ToolFormValues> =>
-  (values) => {
-    const errors = collectErrors(actualSchema, requiredMessages, values);
-    return Object.keys(errors).length > 0 ? { values: {}, errors } : { values, errors: {} };
+  (values): ResolverResult<ToolFormValues> => {
+    const errors = collectErrors(actualSchema, requiredMessages, argumentValues(actualSchema, values));
+    if (Object.keys(errors).length === 0) return { values, errors: {} };
+    return {
+      values: {},
+      errors: {
+        args: Object.fromEntries(
+          Object.keys(actualSchema.properties ?? {}).flatMap((key, index) =>
+            Object.hasOwn(errors, key) ? [[index, errors[key]]] : [],
+          ),
+        ),
+      },
+    };
   };
 
 const labelFor = (key: string, prop: InputSchemaProperty, required: boolean): React.ReactNode => (
@@ -238,10 +251,7 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
     }, [schema]);
 
     const defaultValues = useMemo<ToolFormValues>(
-      () =>
-        Object.fromEntries(
-          Object.entries(actualSchema.properties ?? {}).map(([key, prop]) => [key, getInitialValueForField(prop)]),
-        ),
+      () => ({ args: Object.values(actualSchema.properties ?? {}).map(getInitialValueForField) }),
       [actualSchema],
     );
 
@@ -255,7 +265,7 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
 
     useImperativeHandle(ref, () => ({
       getSubmitValues: async () => {
-        const values = form.getValues();
+        const values = argumentValues(actualSchema, form.getValues());
         const errors = collectErrors(actualSchema, requiredMessages, values);
         if (Object.keys(errors).length > 0) {
           await form.trigger();
@@ -286,14 +296,16 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
           <FieldGroup>
             <FormField
               control={form.control}
-              name="input"
+              name="args.0"
               label={
                 <span>
                   Input <span className="text-destructive">*</span>
                 </span>
               }
             >
-              {(field) => <Input {...field} value={field.value as string} placeholder="Enter input for this tool" />}
+              {(field) => (
+                <Input {...field} value={(field.value as string) ?? ""} placeholder="Enter input for this tool" />
+              )}
             </FormField>
           </FieldGroup>
         </form>
@@ -318,13 +330,13 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
           className={className}
         >
           <FieldGroup>
-            {Object.entries(actualSchema.properties).map(([key, prop]) => {
+            {Object.entries(actualSchema.properties).map(([key, prop], index) => {
               const required = actualSchema.required?.includes(key) ?? false;
               return (
                 <FormField
                   key={`${tool.name}-${key}`}
                   control={form.control}
-                  name={key}
+                  name={`args.${index}`}
                   label={labelFor(key, prop, required)}
                 >
                   {(field) => {
@@ -375,7 +387,7 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
                           {...field}
                           type="number"
                           step={prop.type === "integer" ? 1 : undefined}
-                          value={field.value as number | string}
+                          value={(field.value as number | string) ?? ""}
                           placeholder={prop.description || `Enter ${key}`}
                         />
                       );
@@ -385,7 +397,7 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
                         <Textarea
                           {...field}
                           rows={prop.type === "object" ? 4 : 3}
-                          value={field.value as string}
+                          value={(field.value as string) ?? ""}
                           spellCheck={false}
                           className="font-mono"
                           placeholder={
@@ -398,7 +410,7 @@ const MCPToolArgumentsForm = forwardRef<MCPToolArgumentsFormRef, MCPToolArgument
                     return (
                       <Input
                         {...field}
-                        value={field.value as string}
+                        value={(field.value as string) ?? ""}
                         placeholder={prop.description || `Enter ${key}`}
                       />
                     );
diff --git a/ui/litellm-dashboard/src/components/object_permissions_view.tsx b/ui/litellm-dashboard/src/components/object_permissions_view.tsx
index e90645a9e9f..ae46729222a 100644
--- a/ui/litellm-dashboard/src/components/object_permissions_view.tsx
+++ b/ui/litellm-dashboard/src/components/object_permissions_view.tsx
@@ -30,6 +30,7 @@ export function ObjectPermissionsView({
   const agents = objectPermission?.agents || [];
   const agentAccessGroups = objectPermission?.agent_access_groups || [];
   const searchTools = objectPermission?.search_tools || [];
+  const skills = objectPermission?.skills || [];
 
   const content = (
     <div className={variant === "card" ? "grid grid-cols-1 @xl:grid-cols-2 @4xl:grid-cols-3 gap-6" : "space-y-4"}>
@@ -58,6 +59,16 @@ export function ObjectPermissionsView({
           <p className="mt-1 block text-xs break-words text-foreground">{searchTools.join(", ")}</p>
         )}
       </div>
+      <div className="min-w-0 rounded-md border border-border p-4">
+        <p className="text-sm font-medium text-foreground">Skills</p>
+        {skills.length === 0 ? (
+          <p className="mt-1 block text-xs text-muted-foreground">
+            No private skills granted. Only enabled (public) Claude Code plugins are visible.
+          </p>
+        ) : (
+          <p className="mt-1 block text-xs break-words text-foreground">{skills.join(", ")}</p>
+        )}
+      </div>
     </div>
   );
 
diff --git a/ui/litellm-dashboard/src/components/organisms/createKeyPayload.test.ts b/ui/litellm-dashboard/src/components/organisms/createKeyPayload.test.ts
index 8b7283370a2..fef94cc3c2b 100644
--- a/ui/litellm-dashboard/src/components/organisms/createKeyPayload.test.ts
+++ b/ui/litellm-dashboard/src/components/organisms/createKeyPayload.test.ts
@@ -301,6 +301,16 @@ describe("object_permission", () => {
     ).toStrictEqual(aliasOnly({ object_permission: { agents: ["a-1"], agent_access_groups: ["ag-1"] } }));
   });
 
+  it("moves the selected skills under object_permission and off the top level", () => {
+    expect(payloadOf(build({ key_alias: "my-key", allowed_skills: ["private-skill"] }))).toStrictEqual(
+      aliasOnly({ object_permission: { skills: ["private-skill"] } }),
+    );
+  });
+
+  it("sends no object_permission for an empty skill selection", () => {
+    expect(payloadOf(build({ key_alias: "my-key", allowed_skills: [] }))).toStrictEqual(aliasOnly());
+  });
+
   it("merges every source into a single object_permission", () => {
     const everySource = {
       key_alias: "my-key",
@@ -308,6 +318,7 @@ describe("object_permission", () => {
       allowed_mcp_servers_and_groups: { servers: ["s-1"], accessGroups: ["g-1"], toolsets: ["t-1"] },
       mcp_tool_permissions: { "s-1": ["read"] },
       allowed_agents_and_groups: { agents: ["a-1"], accessGroups: ["ag-1"] },
+      allowed_skills: ["private-skill"],
     };
     expect(payloadOf(build(everySource))).toStrictEqual(
       aliasOnly({
@@ -319,6 +330,7 @@ describe("object_permission", () => {
           mcp_tool_permissions: { "s-1": ["read"] },
           agents: ["a-1"],
           agent_access_groups: ["ag-1"],
+          skills: ["private-skill"],
         },
       }),
     );
diff --git a/ui/litellm-dashboard/src/components/organisms/createKeyPayload.ts b/ui/litellm-dashboard/src/components/organisms/createKeyPayload.ts
index a528dbaeb2c..37a973d5def 100644
--- a/ui/litellm-dashboard/src/components/organisms/createKeyPayload.ts
+++ b/ui/litellm-dashboard/src/components/organisms/createKeyPayload.ts
@@ -112,6 +112,7 @@ interface PermissionSources {
   readonly toolPermissions: unknown | undefined;
   readonly extraMcpAccessGroups: unknown[] | undefined;
   readonly agents: AgentSelection | undefined;
+  readonly skills: unknown[] | undefined;
 }
 
 const readPermissionSources = (values: Record<string, unknown>): PermissionSources => ({
@@ -120,6 +121,7 @@ const readPermissionSources = (values: Record<string, unknown>): PermissionSourc
   toolPermissions: readToolPermissions(values.mcp_tool_permissions),
   extraMcpAccessGroups: nonEmptyList(values.allowed_mcp_access_groups),
   agents: readAgentSelection(values.allowed_agents_and_groups),
+  skills: nonEmptyList(values.allowed_skills),
 });
 
 const buildObjectPermission = ({
@@ -128,6 +130,7 @@ const buildObjectPermission = ({
   toolPermissions,
   extraMcpAccessGroups,
   agents,
+  skills,
 }: PermissionSources): Record<string, unknown> | undefined => {
   const permission: Record<string, unknown> = {
     ...(vectorStores && { vector_stores: vectorStores }),
@@ -138,6 +141,7 @@ const buildObjectPermission = ({
     ...(extraMcpAccessGroups && { mcp_access_groups: extraMcpAccessGroups }),
     ...(agents?.agents && { agents: agents.agents }),
     ...(agents?.accessGroups && { agent_access_groups: agents.accessGroups }),
+    ...(skills && { skills }),
   };
   return Object.keys(permission).length > 0 ? permission : undefined;
 };
@@ -148,6 +152,7 @@ const consumedSourceKeys = (
 ): ReadonlySet<string> =>
   new Set<string>([
     "mcp_tool_permissions",
+    "allowed_skills",
     ...(values.disable_global_guardrails ? [] : ["disable_global_guardrails"]),
     ...(vectorStores ? ["allowed_vector_store_ids"] : []),
     ...(mcp ? ["allowed_mcp_servers_and_groups"] : []),
diff --git a/ui/litellm-dashboard/src/components/organisms/create_key_button.integration.test.tsx b/ui/litellm-dashboard/src/components/organisms/create_key_button.integration.test.tsx
index 3471ef00eb0..2bf39bf4cd7 100644
--- a/ui/litellm-dashboard/src/components/organisms/create_key_button.integration.test.tsx
+++ b/ui/litellm-dashboard/src/components/organisms/create_key_button.integration.test.tsx
@@ -84,6 +84,13 @@ vi.mock("../networking", async (importOriginal) => {
     getPossibleUserRoles: vi.fn().mockResolvedValue({}),
     userFilterUICall: vi.fn().mockResolvedValue([]),
     getAgentsList: vi.fn().mockResolvedValue({ agents: [] }),
+    getClaudeCodePluginsList: vi.fn().mockResolvedValue({
+      plugins: [
+        { name: "public-skill", enabled: true },
+        { name: "private-skill", enabled: false },
+      ],
+      count: 2,
+    }),
     getPassThroughEndpointsCall: vi.fn().mockResolvedValue({ endpoints: [] }),
     vectorStoreListCall: vi.fn().mockResolvedValue({ data: [] }),
     listMCPTools: vi.fn().mockResolvedValue(emptyMcpTools),
@@ -109,6 +116,7 @@ const OPENAPI_SCHEMA = {
 const SECTIONS = {
   mcp: /MCP Settings/i,
   agent: /Agent Settings/i,
+  skill: /Skill Settings/i,
   logging: /Logging Settings/i,
   router: /Router Settings/i,
   aliases: /Model Aliases/i,
@@ -164,6 +172,7 @@ const ROUTER_SETTINGS_DEFAULT = {
 const SECTION_PAYLOAD_ADDITIONS: Record<keyof typeof SECTIONS, Record<string, unknown>> = {
   mcp: { allowed_mcp_servers_and_groups: { servers: [], accessGroups: [] } },
   agent: { allowed_agents_and_groups: undefined },
+  skill: {},
   logging: {},
   router: { router_settings: ROUTER_SETTINGS_DEFAULT },
   aliases: {},
@@ -329,6 +338,21 @@ describe("CreateKey", () => {
       expect(Object.keys(serialised).sort()).toStrictEqual([...wireKeys].sort());
     });
 
+    it("moves a picked private skill under object_permission.skills and off the top level", async () => {
+      await openModal();
+      await nameTheKey();
+      await openSection(/Optional Settings/i);
+      await openSection(SECTIONS.skill);
+      await userEvent.click(await screen.findByRole("combobox", { name: "Select skills (optional)" }));
+      await userEvent.click(await screen.findByRole("option", { name: "private-skill (private)" }));
+      await userEvent.keyboard("{Escape}");
+      await submit();
+
+      const payload = await createdPayload();
+      expect(payload.object_permission).toStrictEqual({ skills: ["private-skill"] });
+      expect(payload).not.toHaveProperty("allowed_skills");
+    });
+
     it("omits a budget typed into a section the user closed again, rather than sending it as null", async () => {
       await openModal();
       await nameTheKey();
diff --git a/ui/litellm-dashboard/src/components/organisms/create_key_button.tsx b/ui/litellm-dashboard/src/components/organisms/create_key_button.tsx
index 16ea99ea94c..831cb0cf6a6 100644
--- a/ui/litellm-dashboard/src/components/organisms/create_key_button.tsx
+++ b/ui/litellm-dashboard/src/components/organisms/create_key_button.tsx
@@ -27,6 +27,7 @@ import React, { useEffect, useMemo, useRef, useState } from "react";
 import { type Control, useForm, useWatch, type UseFormSetValue } from "react-hook-form";
 import { rolesWithWriteAccess } from "../../utils/roles";
 import AgentSelector from "../agent_management/AgentSelector";
+import SkillSelector from "../skills/SkillSelector";
 import AccessGroupSelector from "../common_components/AccessGroupSelector";
 import BudgetDurationDropdown from "../common_components/budget_duration_dropdown";
 import SchemaFormFields from "../common_components/check_openapi_schema";
@@ -1557,6 +1558,36 @@ const CreateKey: React.FC<CreateKeyProps> = ({ team, teams, data, addKey, autoOp
                         </CollapsibleContent>
                       </Collapsible>
 
+                      <Collapsible className="mt-4 mb-4 overflow-hidden rounded-lg border">
+                        <CollapsibleTrigger className={SECTION_HEADER_CLASS}>
+                          <b>Skill Settings</b>
+                          <ChevronDown className={SECTION_CHEVRON_CLASS} />
+                        </CollapsibleTrigger>
+                        <CollapsibleContent className="px-4 pb-3">
+                          <MountedFormField
+                            label={
+                              <span>
+                                Allowed Skills{" "}
+                                <SimpleTooltip content="Enabled skills are visible to every key. Grant disabled (private) Claude Code plugins to this key here">
+                                  <Info className="ml-1 inline size-3.5 align-text-bottom" />
+                                </SimpleTooltip>
+                              </span>
+                            }
+                            name="allowed_skills"
+                            help="Select private skills this key can access in the Claude Code marketplace"
+                          >
+                            {(control) => (
+                              <SkillSelector
+                                onChange={control.onChange}
+                                value={control.value as string[] | undefined}
+                                accessToken={accessToken}
+                                placeholder="Select skills (optional)"
+                              />
+                            )}
+                          </MountedFormField>
+                        </CollapsibleContent>
+                      </Collapsible>
+
                       {premiumUser ? (
                         <Collapsible className="mt-4 mb-4 overflow-hidden rounded-lg border">
                           <CollapsibleTrigger className={SECTION_HEADER_CLASS}>
diff --git a/ui/litellm-dashboard/src/components/shared/EntityLink.test.tsx b/ui/litellm-dashboard/src/components/shared/EntityLink.test.tsx
index a02f1699c30..3d6fc9a435b 100644
--- a/ui/litellm-dashboard/src/components/shared/EntityLink.test.tsx
+++ b/ui/litellm-dashboard/src/components/shared/EntityLink.test.tsx
@@ -25,6 +25,12 @@ describe("EntityLink", () => {
     expect(push).toHaveBeenCalledWith("/ui/users?user=u1");
   });
 
+  it("renders the label as plain text when there is no href to point at", () => {
+    render(<EntityLink>default_user_id</EntityLink>);
+    expect(screen.queryByRole("link")).not.toBeInTheDocument();
+    expect(screen.getByText("default_user_id")).toBeInTheDocument();
+  });
+
   it("leaves modified clicks to the browser so new-tab shortcuts keep working", async () => {
     const user = userEvent.setup();
     render(<EntityLink href="/ui/users?user=u1">alice</EntityLink>);
diff --git a/ui/litellm-dashboard/src/components/shared/EntityLink.tsx b/ui/litellm-dashboard/src/components/shared/EntityLink.tsx
index 4054b929943..4885835a42c 100644
--- a/ui/litellm-dashboard/src/components/shared/EntityLink.tsx
+++ b/ui/litellm-dashboard/src/components/shared/EntityLink.tsx
@@ -19,12 +19,24 @@ export function useEntityLinkClick(href: string): (e: React.MouseEvent) => void
 }
 
 interface EntityLinkProps {
-  href: string;
+  href?: string;
   className?: string;
   children: React.ReactNode;
 }
 
 export function EntityLink({ href, className, children }: EntityLinkProps) {
+  if (!href) {
+    return <span className={cn("inline-block min-w-0 max-w-full truncate font-semibold", className)}>{children}</span>;
+  }
+
+  return (
+    <LinkedEntity href={href} className={className}>
+      {children}
+    </LinkedEntity>
+  );
+}
+
+function LinkedEntity({ href, className, children }: EntityLinkProps & { href: string }) {
   const handleClick = useEntityLinkClick(href);
 
   return (
diff --git a/ui/litellm-dashboard/src/components/shared/table_cells/UserPopoverCell.tsx b/ui/litellm-dashboard/src/components/shared/table_cells/UserPopoverCell.tsx
new file mode 100644
index 00000000000..eb786e45541
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/shared/table_cells/UserPopoverCell.tsx
@@ -0,0 +1,62 @@
+"use client";
+
+import DefaultProxyAdminTag from "@/components/common_components/DefaultProxyAdminTag";
+import { HoverCard, HoverCardContent, HoverCardTrigger } from "@/components/ui/hover-card";
+import { userDetailHref } from "@/utils/entityLinks";
+import { DEFAULT_PROXY_ADMIN_USER_ID } from "@/utils/sentinels";
+
+import { IdCell } from "./id_cell";
+import { IdentityCell } from "./identity_cell";
+
+export const ENTITY_CELL_TITLE_CLASSES = "font-mono text-xs font-normal";
+
+interface UserPopoverCellProps {
+  userAlias: string | null;
+  userEmail: string | null;
+  userId: string | null;
+  width: number;
+}
+
+export function UserPopoverCell({ userAlias, userEmail, userId, width }: UserPopoverCellProps) {
+  const displayValue = userAlias || userEmail || userId;
+  const isDefaultAdmin = userId === DEFAULT_PROXY_ADMIN_USER_ID;
+
+  const popoverContent = (
+    <div className="flex flex-col gap-2 text-xs min-w-[200px] max-w-[300px]">
+      {[
+        { label: "User Alias", value: userAlias },
+        { label: "User Email", value: userEmail },
+        { label: "User ID", value: userId },
+      ].map(({ label, value }) => (
+        <div key={label} className="flex flex-col min-w-0">
+          <span className="text-muted-foreground">{label}</span>
+          {value ? (
+            <IdCell value={value} variant="plain" copyable copyLabel={`Copy ${label}`} className="max-w-full" />
+          ) : (
+            <span className="font-mono">-</span>
+          )}
+        </div>
+      ))}
+    </div>
+  );
+
+  const trigger =
+    isDefaultAdmin && !userAlias && !userEmail ? (
+      <DefaultProxyAdminTag userId={userId} />
+    ) : (
+      <IdentityCell
+        title={displayValue || "-"}
+        titleClassName={ENTITY_CELL_TITLE_CLASSES}
+        href={userId ? userDetailHref(userId) : undefined}
+      />
+    );
+
+  return (
+    <HoverCard>
+      <HoverCardTrigger render={<span className="block" style={{ maxWidth: width, overflow: "hidden" }} />}>
+        {trigger}
+      </HoverCardTrigger>
+      <HoverCardContent align="start">{popoverContent}</HoverCardContent>
+    </HoverCard>
+  );
+}
diff --git a/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.test.tsx b/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.test.tsx
index 395c1815dd0..c715210fdde 100644
--- a/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.test.tsx
+++ b/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.test.tsx
@@ -71,6 +71,14 @@ describe("IdCell", () => {
     expect(rowClick).not.toHaveBeenCalled();
   });
 
+  it("names the copy button after the field it copies", async () => {
+    const user = userEvent.setup();
+    render(<IdCell value="alice@example.com" copyable copyLabel="Copy User Email" />);
+    expect(screen.queryByRole("button", { name: "Copy ID" })).not.toBeInTheDocument();
+    await user.click(screen.getByRole("button", { name: "Copy User Email" }));
+    expect(copyToClipboardMock).toHaveBeenCalledWith("alice@example.com");
+  });
+
   it("passes dataTestId through to the id element", () => {
     render(<IdCell value="k-1" dataTestId="key-id-cell" />);
     expect(screen.getByTestId("key-id-cell")).toHaveTextContent("k-1");
diff --git a/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.tsx b/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.tsx
index 1b109a86106..33c7f835e64 100644
--- a/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.tsx
+++ b/ui/litellm-dashboard/src/components/shared/table_cells/id_cell.tsx
@@ -15,6 +15,7 @@ interface IdCellProps {
   variant?: IdCellVariant;
   onClick?: (value: string) => void;
   copyable?: boolean;
+  copyLabel?: string;
   truncate?: boolean;
   fallback?: string;
   tooltip?: React.ReactNode;
@@ -39,6 +40,7 @@ export function IdCell({
   variant = "pill",
   onClick,
   copyable = false,
+  copyLabel = "Copy ID",
   truncate = true,
   fallback = "-",
   tooltip,
@@ -80,7 +82,7 @@ export function IdCell({
       {withTooltip}
       <button
         type="button"
-        aria-label="Copy ID"
+        aria-label={copyLabel}
         className="shrink-0 cursor-pointer text-muted-foreground hover:text-foreground"
         onClick={(event) => {
           event.stopPropagation();
diff --git a/ui/litellm-dashboard/src/components/shared/table_cells/index.ts b/ui/litellm-dashboard/src/components/shared/table_cells/index.ts
index 99b54f9aad0..34e3701eed4 100644
--- a/ui/litellm-dashboard/src/components/shared/table_cells/index.ts
+++ b/ui/litellm-dashboard/src/components/shared/table_cells/index.ts
@@ -13,3 +13,4 @@ export { ModelsCell } from "./models_cell";
 export { MoneyCell } from "./money_cell";
 export { SpendBudgetCell } from "./spend_budget_cell";
 export { StatusBadge, type StatusTone } from "./status_badge";
+export { UserPopoverCell, ENTITY_CELL_TITLE_CLASSES } from "./UserPopoverCell";
diff --git a/ui/litellm-dashboard/src/components/skills/SkillSelector.test.tsx b/ui/litellm-dashboard/src/components/skills/SkillSelector.test.tsx
new file mode 100644
index 00000000000..59aff7c25de
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/skills/SkillSelector.test.tsx
@@ -0,0 +1,54 @@
+import userEvent from "@testing-library/user-event";
+import { beforeEach, describe, expect, it, vi } from "vitest";
+import { renderWithProviders, screen } from "../../../tests/test-utils";
+import { getClaudeCodePluginsList } from "../networking";
+import SkillSelector from "./SkillSelector";
+
+vi.mock("../networking", () => ({
+  getClaudeCodePluginsList: vi.fn(),
+}));
+
+describe("SkillSelector", () => {
+  beforeEach(() => {
+    vi.clearAllMocks();
+    vi.mocked(getClaudeCodePluginsList).mockResolvedValue({
+      plugins: [
+        { name: "public-skill", enabled: true },
+        { name: "private-skill", enabled: false },
+      ],
+      count: 2,
+    });
+  });
+
+  it("should list marketplace plugins and mark disabled ones as private", async () => {
+    const user = userEvent.setup();
+    renderWithProviders(<SkillSelector accessToken="token" onChange={vi.fn()} />);
+
+    await user.click(screen.getByRole("combobox"));
+
+    expect(await screen.findByRole("option", { name: "public-skill" })).toBeInTheDocument();
+    expect(screen.getByRole("option", { name: "private-skill (private)" })).toBeInTheDocument();
+    expect(getClaudeCodePluginsList).toHaveBeenCalledWith("token");
+  });
+
+  it("should report the selected skill names", async () => {
+    const user = userEvent.setup();
+    const onChange = vi.fn();
+    renderWithProviders(<SkillSelector accessToken="token" onChange={onChange} />);
+
+    await user.click(screen.getByRole("combobox"));
+    await user.click(await screen.findByRole("option", { name: "private-skill (private)" }));
+
+    expect(onChange).toHaveBeenCalledWith(["private-skill"]);
+  });
+
+  it("should clear all selected skills", async () => {
+    const user = userEvent.setup();
+    const onChange = vi.fn();
+    renderWithProviders(<SkillSelector accessToken="" value={["public-skill"]} onChange={onChange} />);
+
+    await user.click(screen.getByRole("button", { name: "Clear all skills" }));
+
+    expect(onChange).toHaveBeenCalledWith([]);
+  });
+});
diff --git a/ui/litellm-dashboard/src/components/skills/SkillSelector.tsx b/ui/litellm-dashboard/src/components/skills/SkillSelector.tsx
new file mode 100644
index 00000000000..b21c8b7e872
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/skills/SkillSelector.tsx
@@ -0,0 +1,109 @@
+import React, { useEffect, useState } from "react";
+import {
+  Combobox,
+  ComboboxChip,
+  ComboboxChips,
+  ComboboxChipsInput,
+  ComboboxClear,
+  ComboboxContent,
+  ComboboxEmpty,
+  ComboboxItem,
+  ComboboxList,
+  ComboboxValue,
+  useComboboxAnchor,
+} from "@/components/ui/combobox";
+import { cn } from "@/lib/cva.config";
+import { getClaudeCodePluginsList } from "../networking";
+
+export interface SkillSelectorProps {
+  onChange: (selected: string[]) => void;
+  value?: string[];
+  className?: string;
+  accessToken: string;
+  placeholder?: string;
+  disabled?: boolean;
+}
+
+interface SkillOption {
+  readonly name: string;
+  readonly enabled: boolean;
+}
+
+const readSkillOptions = (data: unknown): SkillOption[] => {
+  const plugins = (data as { plugins?: unknown[] } | undefined)?.plugins;
+  if (!Array.isArray(plugins)) return [];
+  return plugins.flatMap((plugin) => {
+    const record = plugin as { name?: unknown; enabled?: unknown };
+    return typeof record.name === "string" && record.name.length > 0
+      ? [{ name: record.name, enabled: record.enabled !== false }]
+      : [];
+  });
+};
+
+const SkillSelector: React.FC<SkillSelectorProps> = ({
+  onChange,
+  value,
+  className,
+  accessToken,
+  placeholder = "Select skills (optional)",
+  disabled = false,
+}) => {
+  const anchor = useComboboxAnchor();
+  const [options, setOptions] = useState<SkillOption[]>([]);
+  const [loading, setLoading] = useState(false);
+
+  useEffect(() => {
+    const load = async () => {
+      if (!accessToken) return;
+      setLoading(true);
+      try {
+        setOptions(readSkillOptions(await getClaudeCodePluginsList(accessToken)));
+      } catch (e) {
+        console.error("Failed to load skills:", e);
+      } finally {
+        setLoading(false);
+      }
+    };
+    load();
+  }, [accessToken]);
+
+  return (
+    <Combobox
+      multiple
+      items={options.map((option) => option.name)}
+      value={value ?? []}
+      onValueChange={(selected: string[]) => onChange(selected)}
+      disabled={disabled}
+    >
+      <ComboboxChips render={<div ref={anchor} />} className={cn("w-full", className)} aria-busy={loading}>
+        <ComboboxValue>
+          {(selected: string[]) =>
+            selected.map((skill) => (
+              <ComboboxChip key={skill} aria-label={skill}>
+                {skill}
+              </ComboboxChip>
+            ))
+          }
+        </ComboboxValue>
+        <ComboboxChipsInput placeholder={placeholder} aria-label={placeholder} disabled={disabled} />
+        {value && value.length > 0 && <ComboboxClear aria-label="Clear all skills" disabled={disabled} />}
+      </ComboboxChips>
+      <ComboboxContent anchor={anchor}>
+        <ComboboxEmpty>{loading ? "Loading skills…" : "No skills found"}</ComboboxEmpty>
+        <ComboboxList>
+          {(skill: string) => {
+            const isPrivate = options.some((option) => option.name === skill && !option.enabled);
+            return (
+              <ComboboxItem key={skill} value={skill} aria-label={isPrivate ? `${skill} (private)` : skill}>
+                {skill}
+                {isPrivate && <span className="ml-2 text-xs text-muted-foreground">private</span>}
+              </ComboboxItem>
+            );
+          }}
+        </ComboboxList>
+      </ComboboxContent>
+    </Combobox>
+  );
+};
+
+export default SkillSelector;
diff --git a/ui/litellm-dashboard/src/components/team/TeamInfo.test.tsx b/ui/litellm-dashboard/src/components/team/TeamInfo.test.tsx
index b286c8c1303..a25ca28651a 100644
--- a/ui/litellm-dashboard/src/components/team/TeamInfo.test.tsx
+++ b/ui/litellm-dashboard/src/components/team/TeamInfo.test.tsx
@@ -52,6 +52,7 @@ vi.mock("@/components/networking", () => ({
   listMCPTools: vi.fn().mockResolvedValue({ tools: [] }),
   vectorStoreListCall: vi.fn().mockResolvedValue({ data: [] }),
   getAgentsList: vi.fn().mockResolvedValue({ agents: [] }),
+  getClaudeCodePluginsList: vi.fn().mockResolvedValue({ plugins: [], count: 0 }),
 }));
 
 const can = vi.fn();
@@ -1990,6 +1991,7 @@ describe("TeamInfoView - the exact bytes the update call sends", () => {
     agents: [],
     agent_access_groups: [],
     vector_stores: ["vs-1"],
+    skills: [],
   };
 
   it("leaves every team member key out of the request body for an untouched save with both sections closed", async () => {
@@ -2052,6 +2054,47 @@ describe("TeamInfoView - the exact bytes the update call sends", () => {
     expect(objectPermission.agent_access_groups).toStrictEqual([]);
   });
 
+  it("resends the stored skills when the selector is left untouched", async () => {
+    const user = userEvent.setup({ delay: null });
+    vi.mocked(networking.teamInfoCall).mockResolvedValue(
+      createMockTeamData({ models: ["gpt-4"], object_permission: { skills: ["private-skill"] } }),
+    );
+    vi.mocked(networking.teamUpdateCall).mockResolvedValue({ data: {}, team_id: "123" } as any);
+
+    renderWithProviders(<TeamInfoView {...props} />);
+    await waitFor(() => expect(screen.queryAllByText("Test Team").length).toBeGreaterThan(0));
+    await user.click(screen.getByRole("tab", { name: "Settings" }));
+    await user.click(await screen.findByRole("button", { name: /edit settings/i }));
+    await screen.findByLabelText("Team Name");
+
+    const payload = await save(user);
+
+    const objectPermission = wireBody(payload).object_permission as Record<string, unknown>;
+    expect(objectPermission.skills).toStrictEqual(["private-skill"]);
+  });
+
+  it("sends an empty skills array after the last skill chip is removed", async () => {
+    const user = userEvent.setup({ delay: null });
+    vi.mocked(networking.teamInfoCall).mockResolvedValue(
+      createMockTeamData({ models: ["gpt-4"], object_permission: { skills: ["private-skill"] } }),
+    );
+    vi.mocked(networking.teamUpdateCall).mockResolvedValue({ data: {}, team_id: "123" } as any);
+
+    renderWithProviders(<TeamInfoView {...props} />);
+    await waitFor(() => expect(screen.queryAllByText("Test Team").length).toBeGreaterThan(0));
+    await user.click(screen.getByRole("tab", { name: "Settings" }));
+    await user.click(await screen.findByRole("button", { name: /edit settings/i }));
+    await screen.findByLabelText("Team Name");
+
+    await user.click(within(screen.getByLabelText("private-skill")).getByRole("button"));
+    expect(screen.queryByLabelText("private-skill")).not.toBeInTheDocument();
+
+    const payload = await save(user);
+
+    const objectPermission = wireBody(payload).object_permission as Record<string, unknown>;
+    expect(objectPermission.skills).toStrictEqual([]);
+  });
+
   it("sends an empty vector_stores array after the last vector store chip is removed", async () => {
     const user = userEvent.setup({ delay: null });
     await openEditor(user);
diff --git a/ui/litellm-dashboard/src/components/team/TeamInfo.tsx b/ui/litellm-dashboard/src/components/team/TeamInfo.tsx
index 4947cec1441..988e2e082aa 100644
--- a/ui/litellm-dashboard/src/components/team/TeamInfo.tsx
+++ b/ui/litellm-dashboard/src/components/team/TeamInfo.tsx
@@ -89,6 +89,7 @@ import ObjectPermissionsView from "../object_permissions_view";
 import NumericalInput from "../shared/numerical_input";
 import VectorStoreSelector from "../vector_store_management/VectorStoreSelector";
 import SearchToolSelector from "../search_tools/SearchToolSelector";
+import SkillSelector from "../skills/SkillSelector";
 import EditLoggingSettings from "./EditLoggingSettings";
 import RouterSettingsAccordion, { RouterSettingsAccordionRef } from "../common_components/RouterSettingsAccordion";
 import MemberModal from "./EditMembership";
@@ -371,6 +372,7 @@ const teamUpdateFieldsSchema = z.object({
   mcp_tool_permissions: z.record(z.string(), z.array(z.string())).optional(),
   agents_and_groups: z.object({ agents: z.array(z.string()), accessGroups: z.array(z.string()) }).optional(),
   object_permission_search_tools: z.array(z.string()).optional(),
+  object_permission_skills: z.array(z.string()).optional(),
   organization_id: z.string().nullish(),
   logging_settings: z.array(z.unknown()).optional(),
   secret_manager_settings: z.string().optional(),
@@ -419,6 +421,7 @@ const EMPTY_TEAM_UPDATE_VALUES: TeamUpdateFormValues = {
   mcp_tool_permissions: {},
   agents_and_groups: { agents: [], accessGroups: [] },
   object_permission_search_tools: [],
+  object_permission_skills: [],
   organization_id: null,
   logging_settings: [],
   secret_manager_settings: "",
@@ -485,6 +488,7 @@ const toTeamFormValues = (info: TeamInfoRecord, effectiveGuardrails: string[]):
     accessGroups: info.object_permission?.agent_access_groups || [],
   },
   object_permission_search_tools: info.object_permission?.search_tools || [],
+  object_permission_skills: info.object_permission?.skills || [],
   organization_id: info.organization_id,
   logging_settings: info.metadata?.logging || [],
   secret_manager_settings: info.metadata?.secret_manager_settings
@@ -1047,6 +1051,10 @@ const TeamInfoView: React.FC<TeamInfoProps> = ({
         updateData.object_permission.search_tools = values.object_permission_search_tools;
       }
 
+      if (Array.isArray(values.object_permission_skills)) {
+        updateData.object_permission.skills = values.object_permission_skills;
+      }
+
       // Pass access_group_ids to the update request
       if (values.access_group_ids !== undefined) {
         updateData.access_group_ids = values.access_group_ids;
@@ -1848,6 +1856,24 @@ const TeamInfoView: React.FC<TeamInfoProps> = ({
                     </CollapsibleContent>
                   </Collapsible>
 
+                  <FormField
+                    control={form.control}
+                    name="object_permission_skills"
+                    label={labelWithHint(
+                      "Skills",
+                      "Enabled skills are visible to every team. Grant disabled (private) Claude Code plugins to this team here.",
+                    )}
+                  >
+                    {({ value, onChange }) => (
+                      <SkillSelector
+                        onChange={onChange}
+                        value={value}
+                        accessToken={accessToken || ""}
+                        placeholder="Select skills (optional)"
+                      />
+                    )}
+                  </FormField>
+
                   <FormField control={form.control} name="organization_id" label="Organization">
                     {({ id, value, onChange }) => (
                       <SearchSelect
diff --git a/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.test.tsx b/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.test.tsx
index 0d9d0988aa1..08408fb4ff4 100644
--- a/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.test.tsx
+++ b/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.test.tsx
@@ -10,6 +10,8 @@ vi.mock("@/app/(dashboard)/hooks/keys/useKeys", () => ({
   useKeys: vi.fn(),
 }));
 
+vi.mock("next/navigation", () => ({ useRouter: () => ({ push: vi.fn() }) }));
+
 vi.mock("../key_team_helpers/fetch_available_models_team_key", () => ({
   getModelDisplayName: vi.fn((model: string) => model),
 }));
@@ -384,4 +386,66 @@ describe("TeamVirtualKeysTable", () => {
       expect(screen.getByText("Key Info View")).toBeInTheDocument();
     });
   });
+
+  describe("entity links out of the key rows", () => {
+    const renderRow = async (key: KeyResponse, organization: Organization | null = null) => {
+      mockUseKeys.mockReturnValue({
+        data: { keys: [key], total_count: 1, current_page: 1, total_pages: 1 } as KeysResponse,
+        isPending: false,
+        isFetching: false,
+        refetch: vi.fn(),
+      } as any);
+      renderWithProviders(<TeamVirtualKeysTable {...defaultProps} organization={organization} />);
+      await screen.findByText(key.key_alias as string);
+      return screen.getByRole("row", { name: new RegExp(key.key_alias as string) });
+    };
+
+    it("points the Organization ID cell at the org's detail page", async () => {
+      const row = await renderRow(createMockKey({ organization_id: null }), mockOrganization);
+      expect(within(row).getByRole("link", { name: "org-123" })).toHaveAttribute(
+        "href",
+        "/ui/organizations?org=org-123",
+      );
+    });
+
+    it("points the User Email and User ID cells at the owning user's detail page", async () => {
+      const row = await renderRow(
+        createMockKey({ user_id: "user-1", user: { user_id: "user-1", user_email: "alice@example.com" } }),
+      );
+      expect(within(row).getByRole("link", { name: "alice@example.com" })).toHaveAttribute(
+        "href",
+        "/ui/users?user=user-1",
+      );
+      expect(within(row).getByRole("link", { name: "user-1" })).toHaveAttribute("href", "/ui/users?user=user-1");
+    });
+
+    it("points the Created By cell at the creator's detail page", async () => {
+      const row = await renderRow(
+        createMockKey({
+          created_by: "creator-1",
+          created_by_user: { user_id: "creator-1", user_email: "creator@example.com", user_alias: "The Creator" },
+        }),
+      );
+      expect(within(row).getByRole("link", { name: "The Creator" })).toHaveAttribute(
+        "href",
+        "/ui/users?user=creator-1",
+      );
+    });
+
+    it("leaves the default_user_id placeholder unlinked in the User ID and Created By cells", async () => {
+      const placeholder = { user_id: "default_user_id", user_email: "admin@example.com", user_alias: "Proxy Admin" };
+      const ownedAndCreatedByPlaceholder = {
+        user_id: placeholder.user_id,
+        user: placeholder,
+        created_by: placeholder.user_id,
+        created_by_user: placeholder,
+      };
+      const row = await renderRow(createMockKey(ownedAndCreatedByPlaceholder));
+      expect(within(row).getByText("Default Proxy Admin")).toBeInTheDocument();
+      expect(within(row).getByText("Proxy Admin")).toBeInTheDocument();
+      expect(within(row).queryByRole("link", { name: "Proxy Admin" })).not.toBeInTheDocument();
+      expect(within(row).queryByRole("link", { name: placeholder.user_email })).not.toBeInTheDocument();
+      expect(within(row).queryByRole("link", { name: "Default Proxy Admin" })).not.toBeInTheDocument();
+    });
+  });
 });
diff --git a/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.tsx b/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.tsx
index b0380255b95..5b1b71e060e 100644
--- a/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.tsx
+++ b/ui/litellm-dashboard/src/components/team/TeamVirtualKeysTable.tsx
@@ -1,8 +1,14 @@
 "use client";
 import { useKeys } from "@/app/(dashboard)/hooks/keys/useKeys";
 import { SimpleTooltip } from "@/components/ui/tooltip";
-import CopyButton from "@/components/shared/CopyButton";
-import { DateCell, IdCell, MoneyCell } from "@/components/shared/table_cells";
+import {
+  DateCell,
+  ENTITY_CELL_TITLE_CLASSES,
+  IdCell,
+  IdentityCell,
+  MoneyCell,
+  UserPopoverCell,
+} from "@/components/shared/table_cells";
 import {
   DataTable,
   DataTableFilterDrawer,
@@ -11,8 +17,9 @@ import {
   DataTableToolbar,
 } from "@/components/shared/DataTable";
 import { Badge } from "@/components/ui/badge";
-import { HoverCard, HoverCardContent, HoverCardTrigger } from "@/components/ui/hover-card";
 import { Input } from "@/components/ui/input";
+import { orgDetailHref, userDetailHref } from "@/utils/entityLinks";
+import { DEFAULT_PROXY_ADMIN_USER_ID } from "@/utils/sentinels";
 import { DEBOUNCE_WAIT_MS } from "@/utils/debounceConstants";
 import { useDebouncedValue } from "@tanstack/react-pacer/debouncer";
 import { ColumnDef, ColumnFiltersState, OnChangeFn, PaginationState, SortingState } from "@tanstack/react-table";
@@ -168,7 +175,15 @@ export function TeamVirtualKeysTable({ teamId, teamAlias, organization }: TeamVi
         header: "Organization ID",
         size: 140,
         enableSorting: false,
-        cell: (info) => (info.getValue() ? info.renderValue() : "-"),
+        cell: (info) => {
+          const orgId = info.getValue() as string | null;
+          if (!orgId) return "-";
+          return (
+            <SimpleTooltip content={orgId}>
+              <IdentityCell title={orgId} titleClassName={ENTITY_CELL_TITLE_CLASSES} href={orgDetailHref(orgId)} />
+            </SimpleTooltip>
+          );
+        },
       },
       {
         id: "user_email",
@@ -179,9 +194,14 @@ export function TeamVirtualKeysTable({ teamId, teamAlias, organization }: TeamVi
         cell: (info) => {
           const user = info.getValue() as { user_email?: string } | undefined;
           const value = user?.user_email;
+          const userId = info.row.original.user_id;
           return (
             <SimpleTooltip content={value}>
-              <span className="block max-w-full truncate font-mono text-xs">{value ?? "-"}</span>
+              <IdentityCell
+                title={value ?? "-"}
+                titleClassName={ENTITY_CELL_TITLE_CLASSES}
+                href={value && userId ? userDetailHref(userId) : undefined}
+              />
             </SimpleTooltip>
           );
         },
@@ -194,10 +214,16 @@ export function TeamVirtualKeysTable({ teamId, teamAlias, organization }: TeamVi
         enableSorting: false,
         cell: (info) => {
           const userId = info.getValue() as string | null;
-          const displayValue = userId === "default_user_id" ? "Default Proxy Admin" : userId;
+          if (userId === DEFAULT_PROXY_ADMIN_USER_ID) {
+            return <DefaultProxyAdminTag userId={userId} />;
+          }
           return (
-            <SimpleTooltip content={displayValue}>
-              <span className="block max-w-full truncate font-mono text-xs">{displayValue ?? "-"}</span>
+            <SimpleTooltip content={userId}>
+              <IdentityCell
+                title={userId ?? "-"}
+                titleClassName={ENTITY_CELL_TITLE_CLASSES}
+                href={userId ? userDetailHref(userId) : undefined}
+              />
             </SimpleTooltip>
           );
         },
@@ -221,53 +247,13 @@ export function TeamVirtualKeysTable({ teamId, teamAlias, organization }: TeamVi
           const userId = info.getValue() as string | null;
           if (!userId) return "-";
           const { created_by_user } = info.row.original;
-          const userAlias = created_by_user?.user_alias ?? null;
-          const userEmail = created_by_user?.user_email ?? null;
-          const isDefaultAdmin = userId === "default_user_id";
-          const displayValue = userAlias || userEmail || userId;
-
-          const popoverContent = (
-            <div className="flex min-w-[200px] max-w-[300px] flex-col gap-2 text-xs">
-              {[
-                { label: "User Alias", value: userAlias },
-                { label: "User Email", value: userEmail },
-                { label: "User ID", value: userId },
-              ].map(({ label, value }) => (
-                <div key={label} className="flex flex-col min-w-0">
-                  <span className="text-muted-foreground">{label}</span>
-                  {value ? (
-                    <span className="flex items-center gap-1">
-                      <span className="min-w-0 flex-1 truncate font-mono text-xs">{value}</span>
-                      <CopyButton value={value} label={`Copy ${label}`} />
-                    </span>
-                  ) : (
-                    <span className="font-mono">-</span>
-                  )}
-                </div>
-              ))}
-            </div>
-          );
-
-          if (isDefaultAdmin && !userAlias && !userEmail) {
-            return (
-              <HoverCard>
-                <HoverCardTrigger render={<span className="cursor-default" />}>
-                  <DefaultProxyAdminTag userId={userId} />
-                </HoverCardTrigger>
-                <HoverCardContent align="start">{popoverContent}</HoverCardContent>
-              </HoverCard>
-            );
-          }
-
           return (
-            <HoverCard>
-              <HoverCardTrigger
-                render={<span className="block max-w-full cursor-default truncate font-mono text-xs" />}
-              >
-                {displayValue}
-              </HoverCardTrigger>
-              <HoverCardContent align="start">{popoverContent}</HoverCardContent>
-            </HoverCard>
+            <UserPopoverCell
+              userAlias={created_by_user?.user_alias ?? null}
+              userEmail={created_by_user?.user_email ?? null}
+              userId={userId}
+              width={130}
+            />
           );
         },
       },
diff --git a/ui/litellm-dashboard/src/components/templates/KeyEditViewControls.tsx b/ui/litellm-dashboard/src/components/templates/KeyEditViewControls.tsx
index 2bbbc2bd48b..f5d5562ccfe 100644
--- a/ui/litellm-dashboard/src/components/templates/KeyEditViewControls.tsx
+++ b/ui/litellm-dashboard/src/components/templates/KeyEditViewControls.tsx
@@ -4,8 +4,10 @@ import { Select, SelectContent, SelectItem, SelectTrigger, SelectValue } from "@
 import { Tooltip, TooltipContent, TooltipTrigger } from "@/components/ui/tooltip";
 import { CircleHelp } from "lucide-react";
 import { FormField } from "@/components/shared/form/FormField";
+import AgentSelector from "../agent_management/AgentSelector";
 import NumericalInput from "../shared/numerical_input";
-import { KeyEditFormValues } from "./keyEditFormValues";
+import SkillSelector from "../skills/SkillSelector";
+import { AgentsAndGroups, KeyEditFormValues } from "./keyEditFormValues";
 
 export const labelWithHint = (label: React.ReactNode, hint: string): React.ReactNode => (
   <>
@@ -53,6 +55,36 @@ export const KeyTypeSelect = ({
   </Select>
 );
 
+const SKILLS_HINT =
+  "Enabled skills are visible to every key. Grant disabled (private) Claude Code plugins to this key here.";
+
+export const KeyAgentAndSkillFields = ({
+  control,
+  accessToken,
+}: {
+  control: Control<KeyEditFormValues>;
+  accessToken: string;
+}) => (
+  <>
+    <FormField control={control} name="agents_and_groups" label="Agents / Access Groups">
+      {({ value, onChange }) => (
+        <AgentSelector
+          onChange={onChange}
+          value={value as AgentsAndGroups | undefined}
+          accessToken={accessToken}
+          placeholder="Select agents or access groups (optional)"
+        />
+      )}
+    </FormField>
+
+    <FormField control={control} name="skills" label={labelWithHint("Skills", SKILLS_HINT)}>
+      {({ value, onChange }) => (
+        <SkillSelector onChange={onChange} value={value as string[] | undefined} accessToken={accessToken} />
+      )}
+    </FormField>
+  </>
+);
+
 export const KeyBudgetNumberField = ({
   control,
   name,
diff --git a/ui/litellm-dashboard/src/components/templates/KeyInfoView.handleKeyUpdate.test.tsx b/ui/litellm-dashboard/src/components/templates/KeyInfoView.handleKeyUpdate.test.tsx
index 8a42ecff50c..522af5a85ad 100644
--- a/ui/litellm-dashboard/src/components/templates/KeyInfoView.handleKeyUpdate.test.tsx
+++ b/ui/litellm-dashboard/src/components/templates/KeyInfoView.handleKeyUpdate.test.tsx
@@ -366,6 +366,45 @@ describe("KeyInfoView handleKeyUpdate mcp_toolsets", () => {
   });
 });
 
+describe("KeyInfoView handleKeyUpdate skills", () => {
+  it("should forward the skills the edit form supplies into object_permission and drop the form key", async () => {
+    renderView(true);
+
+    fireEvent.click(screen.getByText("Settings"));
+    fireEvent.click(screen.getByText("Edit Settings"));
+    (globalThis as any).__TEST_FORM_VALUES = {
+      token: "tok_123",
+      skills: ["private-skill"],
+    };
+
+    fireEvent.click(screen.getByText("Mock Submit"));
+
+    await waitFor(() => expect(keyUpdateCallMock).toHaveBeenCalled());
+
+    const [, sentPayload] = keyUpdateCallMock.mock.calls[0];
+    expect(sentPayload.object_permission.skills).toEqual(["private-skill"]);
+    expect(sentPayload).not.toHaveProperty("skills");
+  });
+
+  it("should send an explicit empty skills list when the form clears every skill", async () => {
+    renderView(true);
+
+    fireEvent.click(screen.getByText("Settings"));
+    fireEvent.click(screen.getByText("Edit Settings"));
+    (globalThis as any).__TEST_FORM_VALUES = {
+      token: "tok_123",
+      skills: [],
+    };
+
+    fireEvent.click(screen.getByText("Mock Submit"));
+
+    await waitFor(() => expect(keyUpdateCallMock).toHaveBeenCalled());
+
+    const [, sentPayload] = keyUpdateCallMock.mock.calls[0];
+    expect(sentPayload.object_permission.skills).toEqual([]);
+  });
+});
+
 describe("KeyInfoView handleKeyUpdate budget_duration", () => {
   it("should send a canonical budget_duration through unchanged", async () => {
     renderView(true);
diff --git a/ui/litellm-dashboard/src/components/templates/keyEditFormValues.ts b/ui/litellm-dashboard/src/components/templates/keyEditFormValues.ts
index f24fb6e5a86..fec8e749143 100644
--- a/ui/litellm-dashboard/src/components/templates/keyEditFormValues.ts
+++ b/ui/litellm-dashboard/src/components/templates/keyEditFormValues.ts
@@ -46,6 +46,7 @@ export interface KeyEditFormValues {
   mcp_servers_and_groups?: McpServersAndGroups;
   mcp_tool_permissions?: Record<string, string[]>;
   agents_and_groups?: AgentsAndGroups;
+  skills?: string[];
   organization_id?: string | null;
   team_id?: string | null;
   logging_settings?: unknown[];
@@ -102,6 +103,7 @@ export const toKeyEditFormValues = (keyData: KeyResponse): KeyEditFormValues =>
     agents: keyData.object_permission?.agents || [],
     accessGroups: keyData.object_permission?.agent_access_groups || [],
   },
+  skills: keyData.object_permission?.skills || [],
   organization_id: keyData.organization_id,
   team_id: keyData.team_id,
   logging_settings: extractLoggingSettings(keyData.metadata),
@@ -148,6 +150,7 @@ export const keyEditFormSchema = z.object({
   mcp_servers_and_groups: z.custom<McpServersAndGroups | undefined>(),
   mcp_tool_permissions: z.custom<Record<string, string[]> | undefined>(),
   agents_and_groups: z.custom<AgentsAndGroups | undefined>(),
+  skills: z.custom<string[] | undefined>(),
   organization_id: z.custom<string | null | undefined>(),
   team_id: z.custom<string | null | undefined>(),
   logging_settings: z.custom<unknown[] | undefined>(),
@@ -196,6 +199,7 @@ export const toSubmittedValues = (
   mcp_servers_and_groups: values.mcp_servers_and_groups,
   mcp_tool_permissions: values.mcp_tool_permissions,
   agents_and_groups: values.agents_and_groups,
+  skills: values.skills,
   organization_id: values.organization_id,
   team_id: values.team_id,
   logging_settings: values.logging_settings,
diff --git a/ui/litellm-dashboard/src/components/templates/key_edit_view.test.tsx b/ui/litellm-dashboard/src/components/templates/key_edit_view.test.tsx
index 35e9268e1c2..b2c2a381b42 100644
--- a/ui/litellm-dashboard/src/components/templates/key_edit_view.test.tsx
+++ b/ui/litellm-dashboard/src/components/templates/key_edit_view.test.tsx
@@ -59,6 +59,7 @@ vi.mock("../networking", async () => {
       agents: [],
     }),
     getAgentAccessGroups: vi.fn().mockResolvedValue([]),
+    getClaudeCodePluginsList: vi.fn().mockResolvedValue({ plugins: [], count: 0 }),
   };
 });
 
@@ -135,6 +136,14 @@ vi.mock("../agent_management/AgentSelector", () => ({
   ),
 }));
 
+vi.mock("../skills/SkillSelector", () => ({
+  default: ({ onChange }: { onChange: (selected: string[]) => void }) => (
+    <button type="button" data-testid="skill-selector" onClick={() => onChange(["private-skill"])}>
+      pick skill
+    </button>
+  ),
+}));
+
 vi.mock("../common_components/AccessGroupSelector", () => ({
   default: ({ value = [], onChange }: { value?: string[]; onChange?: (v: string[]) => void }) => (
     <input
@@ -1907,6 +1916,7 @@ describe("KeyEditView", () => {
     mcp_servers_and_groups: { servers: [], accessGroups: [], toolsets: [] },
     mcp_tool_permissions: {},
     agents_and_groups: { agents: [], accessGroups: [] },
+    skills: [],
     organization_id: null,
     team_id: null,
     logging_settings: [],
@@ -2241,6 +2251,36 @@ describe("KeyEditView", () => {
       expect(onSubmitMock.mock.calls[0][0].agents_and_groups.agents).toEqual(["agent-1"]);
     });
 
+    it("carries a picked skill into the payload", async () => {
+      const onSubmitMock = vi.fn().mockResolvedValue(undefined);
+      renderForPayload(onSubmitMock);
+      await screen.findByRole("button", { name: /save changes/i });
+
+      await userEvent.click(screen.getByRole("button", { name: "pick skill" }));
+      await userEvent.click(screen.getByRole("button", { name: /save changes/i }));
+
+      await waitFor(() => {
+        expect(onSubmitMock).toHaveBeenCalled();
+      });
+      expect(onSubmitMock.mock.calls[0][0].skills).toEqual(["private-skill"]);
+    });
+
+    it("preloads the stored skills into the payload when the selector is left untouched", async () => {
+      const onSubmitMock = vi.fn().mockResolvedValue(undefined);
+      renderForPayload(onSubmitMock, {
+        ...MOCK_KEY_DATA,
+        object_permission: { ...MOCK_KEY_DATA.object_permission, skills: ["stored-skill"] },
+      } as KeyResponse);
+      await screen.findByRole("button", { name: /save changes/i });
+
+      await userEvent.click(screen.getByRole("button", { name: /save changes/i }));
+
+      await waitFor(() => {
+        expect(onSubmitMock).toHaveBeenCalled();
+      });
+      expect(onSubmitMock.mock.calls[0][0].skills).toEqual(["stored-skill"]);
+    });
+
     it("carries an added logging integration into the payload", async () => {
       const onSubmitMock = vi.fn().mockResolvedValue(undefined);
       renderForPayload(onSubmitMock);
diff --git a/ui/litellm-dashboard/src/components/templates/key_edit_view.tsx b/ui/litellm-dashboard/src/components/templates/key_edit_view.tsx
index b1bbbeed6f9..e464dfe5008 100644
--- a/ui/litellm-dashboard/src/components/templates/key_edit_view.tsx
+++ b/ui/litellm-dashboard/src/components/templates/key_edit_view.tsx
@@ -15,7 +15,6 @@ import { FormField } from "@/components/shared/form/FormField";
 import React, { useEffect, useRef, useState } from "react";
 import { hasCapability } from "../../utils/capabilities";
 import { isProxyAdminRole, rolesWithWriteAccess } from "../../utils/roles";
-import AgentSelector from "../agent_management/AgentSelector";
 import AccessGroupSelector from "../common_components/AccessGroupSelector";
 import BudgetDurationDropdown from "../common_components/budget_duration_dropdown";
 import { mapInternalToDisplayNames } from "../callback_info_helpers";
@@ -32,9 +31,8 @@ import {
   modelSentinelOptions,
   parseAllowedRoutes,
 } from "./keyEditFieldNormalizers";
-import { KeyBudgetNumberField, KeyTypeSelect, labelWithHint } from "./KeyEditViewControls";
+import { KeyAgentAndSkillFields, KeyBudgetNumberField, KeyTypeSelect, labelWithHint } from "./KeyEditViewControls";
 import {
-  AgentsAndGroups,
   KeyEditFormValues,
   keyEditFormSchema,
   McpServersAndGroups,
@@ -762,16 +760,7 @@ export function KeyEditView({
             />
           </div>
 
-          <FormField control={form.control} name="agents_and_groups" label="Agents / Access Groups">
-            {({ value, onChange }) => (
-              <AgentSelector
-                onChange={onChange}
-                value={value as AgentsAndGroups | undefined}
-                accessToken={accessToken || ""}
-                placeholder="Select agents or access groups (optional)"
-              />
-            )}
-          </FormField>
+          <KeyAgentAndSkillFields control={form.control} accessToken={accessToken || ""} />
 
           <FormField
             control={form.control}
diff --git a/ui/litellm-dashboard/src/components/templates/key_info_view.tsx b/ui/litellm-dashboard/src/components/templates/key_info_view.tsx
index 969decb6613..8d48e85bc28 100644
--- a/ui/litellm-dashboard/src/components/templates/key_info_view.tsx
+++ b/ui/litellm-dashboard/src/components/templates/key_info_view.tsx
@@ -277,6 +277,14 @@ export default function KeyInfoView({
         delete formValues.agents_and_groups;
       }
 
+      if (formValues.skills !== undefined) {
+        formValues.object_permission = {
+          ...formValues.object_permission,
+          skills: formValues.skills || [],
+        };
+        delete formValues.skills;
+      }
+
       formValues.max_budget = mapEmptyStringToNull(formValues.max_budget);
       formValues.tpm_limit = mapEmptyStringToNull(formValues.tpm_limit);
       formValues.rpm_limit = mapEmptyStringToNull(formValues.rpm_limit);
diff --git a/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/ClassifierAuditView.test.tsx b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/ClassifierAuditView.test.tsx
new file mode 100644
index 00000000000..86e98de5557
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/ClassifierAuditView.test.tsx
@@ -0,0 +1,56 @@
+import { render, screen, within } from "@testing-library/react";
+import userEvent from "@testing-library/user-event";
+import { describe, expect, it, vi } from "vitest";
+import { ClassifierAuditView } from "./ClassifierAuditView";
+
+vi.mock("./JsonViewer", () => ({
+  JsonViewer: ({ data }: { data: unknown }) => <pre>{JSON.stringify(data)}</pre>,
+}));
+
+describe("ClassifierAuditView", () => {
+  it("separates and copies the provider input, source request, and returned verdict", async () => {
+    const user = userEvent.setup();
+    const input = { system: "classification rubric", messages: [{ role: "user", content: "classify this" }] };
+    render(
+      <ClassifierAuditView
+        request={{ classifier_input: input, originating_request_masked: { input: "source-only", api_key: "REDACTED" } }}
+        response={{ tier: "SIMPLE", reason: "a greeting" }}
+      />,
+    );
+    const classifier = within(screen.getByRole("region", { name: "Classifier input" }));
+    expect(classifier.getByText(/classification rubric/)).toBeInTheDocument();
+    expect(classifier.queryByText(/source-only/)).not.toBeInTheDocument();
+    expect(
+      within(screen.getByRole("region", { name: "Originating request, credentials masked" })).getByText(/source-only/),
+    ).toBeInTheDocument();
+    expect(
+      within(screen.getByRole("region", { name: "Classifier response" })).getByText(/a greeting/),
+    ).toBeInTheDocument();
+    await user.click(classifier.getByRole("button", { name: "Copy Classifier input" }));
+    expect(await navigator.clipboard.readText()).toBe(JSON.stringify(input, null, 2));
+  });
+
+  it("does not present legacy source messages as captured classifier input", () => {
+    render(<ClassifierAuditView request={{ messages: [{ content: "legacy source" }] }} response={undefined} />);
+    expect(screen.getAllByText("Not captured or message logging disabled")).toHaveLength(3);
+    expect(screen.queryByRole("button", { name: "Copy Classifier input" })).not.toBeInTheDocument();
+  });
+
+  it("labels truncated input without marking a complete source request as truncated", () => {
+    render(
+      <ClassifierAuditView
+        request={{
+          classifier_input: { system: "partial rubric...litellm_truncated" },
+          originating_request_masked: { input: "source" },
+        }}
+        response={{ tier: "SIMPLE" }}
+      />,
+    );
+    expect(within(screen.getByRole("region", { name: "Classifier input" })).getByRole("status")).toHaveTextContent(
+      "This stored copy is truncated",
+    );
+    expect(
+      within(screen.getByRole("region", { name: "Originating request, credentials masked" })).queryByRole("status"),
+    ).not.toBeInTheDocument();
+  });
+});
diff --git a/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/ClassifierAuditView.tsx b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/ClassifierAuditView.tsx
new file mode 100644
index 00000000000..913700efa9b
--- /dev/null
+++ b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/ClassifierAuditView.tsx
@@ -0,0 +1,52 @@
+import CopyButton from "@/components/shared/CopyButton";
+import { Card, CardContent, CardHeader, CardTitle } from "@/components/ui/card";
+import type { ReactNode } from "react";
+import { JsonViewer } from "./JsonViewer";
+
+interface ClassifierAuditViewProps {
+  request: Record<string, unknown>;
+  response: unknown;
+}
+
+export function ClassifierAuditView({ request, response }: ClassifierAuditViewProps) {
+  return (
+    <div className="mb-6 space-y-4">
+      <AuditField title="Classifier input" value={request.classifier_input}>
+        Provider request payload. A cached call or disabled message logging may have no capture.
+      </AuditField>
+      <AuditField title="Originating request, credentials masked" value={request.originating_request_masked}>
+        Comparison only. This source request was not appended to the classifier input.
+      </AuditField>
+      <AuditField title="Classifier response" value={response}>
+        The returned verdict and any explanation supplied by the classifier. Later routing rules may change the tier.
+      </AuditField>
+    </div>
+  );
+}
+
+function AuditField({ title, value, children }: { title: string; value: unknown; children: ReactNode }) {
+  const serialized = JSON.stringify(value);
+  const truncated = serialized?.includes("litellm_truncated") ?? false;
+
+  return (
+    <Card size="sm" role="region" aria-label={title}>
+      <CardHeader>
+        <CardTitle>{title}</CardTitle>
+        {value != null && <CopyButton value={JSON.stringify(value, null, 2)} label={`Copy ${title}`} />}
+      </CardHeader>
+      <CardContent>
+        <p className="mb-3 text-sm text-muted-foreground">{children}</p>
+        {truncated && (
+          <p role="status" className="mb-3 text-sm text-warning">
+            This stored copy is truncated. The complete payload is unavailable from the configured log storage.
+          </p>
+        )}
+        {value == null ? (
+          <p className="text-sm text-muted-foreground">Not captured or message logging disabled</p>
+        ) : (
+          <JsonViewer data={value} mode="formatted" />
+        )}
+      </CardContent>
+    </Card>
+  );
+}
diff --git a/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.test.tsx b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.integration.test.tsx
similarity index 89%
rename from ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.test.tsx
rename to ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.integration.test.tsx
index e0d6a1d41e0..721525268b3 100644
--- a/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.test.tsx
+++ b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.integration.test.tsx
@@ -272,6 +272,59 @@ describe("LogDetailContent", () => {
     expect(screen.queryByRole("tab", { name: "Request" })).not.toBeInTheDocument();
   });
 
+  it.each(["object", "serialized", "messages only", "null captures"])(
+    "preserves request inspection and copying for classifier logs with %s data",
+    async (shape) => {
+      const user = userEvent.setup();
+      const messages = [{ role: "user", content: "legacy classifier prompt" }];
+      const request = {
+        messages,
+        temperature: 0.5,
+        ...(shape === "null captures" ? { classifier_input: null, originating_request_masked: null } : {}),
+      };
+      const storedRequest = shape === "serialized" ? JSON.stringify(request) : request;
+      const logEntry: Partial<LogEntry> = {
+        call_type: "acompletion",
+        messages,
+        proxy_server_request: shape === "messages only" ? undefined : storedRequest,
+        metadata: { status: "success", internal_call_origin: "autorouter_classifier" },
+      };
+      render(<LogDetailContent logEntry={createLogEntry(logEntry)} />);
+
+      expect(screen.getByText("legacy classifier prompt")).toBeInTheDocument();
+      expect(screen.queryByRole("region", { name: "Classifier input" })).not.toBeInTheDocument();
+      await user.click(screen.getByRole("tab", { name: "JSON", exact: true }));
+      await user.click(screen.getByRole("button", { name: "Copy JSON", exact: true }));
+      expect(await navigator.clipboard.readText()).toBe(
+        JSON.stringify(shape === "messages only" ? messages : request, null, 2),
+      );
+    },
+  );
+
+  it.each([
+    ["classifier_input", "acompletion"],
+    ["originating_request_masked", "acompletion"],
+    ["classifier_input", "aresponses"],
+    ["originating_request_masked", "responses"],
+  ])("shows partial classifier audits when only %s is captured for %s", (field, callType) => {
+    render(
+      <LogDetailContent
+        logEntry={createLogEntry({
+          call_type: callType,
+          proxy_server_request: JSON.stringify({
+            [field]: { messages: [{ role: "user", content: "captured prompt" }] },
+          }),
+          metadata: { status: "success", internal_call_origin: "autorouter_classifier" },
+        })}
+      />,
+    );
+
+    expect(screen.getByRole("region", { name: "Classifier input" })).toBeInTheDocument();
+    expect(screen.getByRole("region", { name: "Originating request, credentials masked" })).toBeInTheDocument();
+    expect(screen.getByText("Not captured or message logging disabled")).toBeInTheDocument();
+    expect(screen.queryByText("Request & Response")).not.toBeInTheDocument();
+  });
+
   it("should display Request and Response tabs when JSON view is selected", async () => {
     const user = userEvent.setup();
     render(<LogDetailContent logEntry={createLogEntry()} />);
diff --git a/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.tsx b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.tsx
index 186cb66592b..b5a3412a96f 100644
--- a/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.tsx
+++ b/ui/litellm-dashboard/src/components/view_logs/LogDetailsDrawer/LogDetailContent.tsx
@@ -48,6 +48,8 @@ import {
 } from "./constants";
 import { ToolsSection } from "../ToolsSection";
 import { PrettyMessagesView } from "./PrettyMessagesView";
+import { ClassifierAuditView } from "./ClassifierAuditView";
+import { AUTOROUTER_CLASSIFIER_ORIGIN } from "./ClassifyTag";
 
 export interface LogDetailContentProps {
   logEntry: LogEntry;
@@ -68,6 +70,12 @@ export function LogDetailContent({ logEntry, isLoadingDetails = false, accessTok
   const metadata = logEntry.metadata || {};
   const hasError = metadata.status === "failure";
   const errorInfo = hasError ? metadata.error_information : null;
+  const isClassifier =
+    metadata.internal_call_origin === AUTOROUTER_CLASSIFIER_ORIGIN &&
+    ["completion", "acompletion", "responses", "aresponses"].includes(logEntry.call_type);
+  const rawRequest = formatData(logEntry.proxy_server_request || logEntry.messages);
+  const hasClassifierAudit =
+    isClassifier && (rawRequest?.classifier_input != null || rawRequest?.originating_request_masked != null);
 
   const hasMessages = checkHasMessages(logEntry.messages);
   const hasResponse = checkHasResponse(logEntry.response);
@@ -88,10 +96,6 @@ export function LogDetailContent({ logEntry, isLoadingDetails = false, accessTok
   // Vector store data
   const hasVectorStoreData = checkHasVectorStoreData(metadata);
 
-  const getRawRequest = () => {
-    return formatData(logEntry.proxy_server_request || logEntry.messages);
-  };
-
   const getFormattedResponse = () => {
     if (hasError && errorInfo) {
       return {
@@ -196,11 +200,15 @@ export function LogDetailContent({ logEntry, isLoadingDetails = false, accessTok
             Loading request &amp; response data...
           </div>
         </div>
-      ) : (
+      ) : null}
+      {!isLoadingDetails && hasClassifierAudit && (
+        <ClassifierAuditView request={rawRequest} response={getFormattedResponse()} />
+      )}
+      {!isLoadingDetails && !hasClassifierAudit && (
         <RequestResponseSection
           hasResponse={hasResponse}
           hasError={hasError}
-          getRawRequest={getRawRequest}
+          getRawRequest={() => rawRequest}
           getFormattedResponse={getFormattedResponse}
           logEntry={logEntry}
         />
@@ -541,22 +549,20 @@ function MetricsSection({ logEntry, metadata }: { logEntry: LogEntry; metadata:
             )}
 
             <DescriptionItem label="Retries">
-              {metadata?.attempted_retries !== undefined && metadata?.attempted_retries !== null ? (
-                metadata.attempted_retries > 0 ? (
-                  <>
-                    {metadata.attempted_retries}
-                    {metadata.max_retries !== undefined && metadata.max_retries !== null
-                      ? ` / ${metadata.max_retries}`
-                      : ""}
-                  </>
-                ) : (
-                  <Badge variant="secondary" className="bg-success/15 text-success">
-                    None
-                  </Badge>
-                )
-              ) : (
-                "-"
+              {metadata?.attempted_retries != null && metadata.attempted_retries > 0 && (
+                <>
+                  {metadata.attempted_retries}
+                  {metadata.max_retries !== undefined && metadata.max_retries !== null
+                    ? ` / ${metadata.max_retries}`
+                    : ""}
+                </>
               )}
+              {metadata?.attempted_retries != null && metadata.attempted_retries <= 0 && (
+                <Badge variant="secondary" className="bg-success/15 text-success">
+                  None
+                </Badge>
+              )}
+              {metadata?.attempted_retries == null && "-"}
             </DescriptionItem>
 
             <DescriptionItem label="Start Time">
@@ -602,16 +608,10 @@ function RequestResponseSection({
   const totalTokens = promptTokens + completionTokens;
   const costBreakdown = logEntry.metadata?.cost_breakdown;
   const useCostBreakdown = costBreakdown?.input_cost !== undefined && costBreakdown?.output_cost !== undefined;
-  const inputCost = useCostBreakdown
-    ? costBreakdown!.input_cost ?? 0
-    : totalTokens > 0
-      ? (totalSpend * promptTokens) / totalTokens
-      : 0;
-  const outputCost = useCostBreakdown
-    ? costBreakdown!.output_cost ?? 0
-    : totalTokens > 0
-      ? (totalSpend * completionTokens) / totalTokens
-      : 0;
+  const estimatedInputCost = totalTokens > 0 ? (totalSpend * promptTokens) / totalTokens : 0;
+  const estimatedOutputCost = totalTokens > 0 ? (totalSpend * completionTokens) / totalTokens : 0;
+  const inputCost = useCostBreakdown ? costBreakdown!.input_cost ?? 0 : estimatedInputCost;
+  const outputCost = useCostBreakdown ? costBreakdown!.output_cost ?? 0 : estimatedOutputCost;
 
   return (
     <div className="bg-card rounded-lg shadow-sm w-full max-w-full overflow-hidden mb-6">
diff --git a/ui/litellm-dashboard/src/lib/autorouter_presets.test.ts b/ui/litellm-dashboard/src/lib/autorouter_presets.test.ts
index 8a5f83adbdf..fed11454c23 100644
--- a/ui/litellm-dashboard/src/lib/autorouter_presets.test.ts
+++ b/ui/litellm-dashboard/src/lib/autorouter_presets.test.ts
@@ -13,6 +13,7 @@ import {
   buildModelAvailability,
   deploymentRefsFromModelInfo,
   normalizeModelName,
+  resolveAvailableModels,
 } from "./autorouter_presets";
 import { DEFAULT_MATCH_THRESHOLD } from "@/components/add_model/SemanticKeywordMatching";
 import { DEFAULT_ESCALATION_KEYWORDS } from "@/components/add_model/EscalationKeywords";
@@ -380,6 +381,18 @@ describe("autorouter_presets", () => {
       expect(availability.underlyingIndex.size).toBe(0);
     });
 
+    it("returns every configured group serving the same underlying model", () => {
+      const availability = buildModelAvailability(
+        ["z-group", "a-group"],
+        [
+          { modelGroup: "z-group", underlyingModels: ["anthropic/claude-sonnet-5"] },
+          { modelGroup: "a-group", underlyingModels: ["bedrock/us.anthropic.claude-sonnet-5-v1:0"] },
+        ],
+      );
+
+      expect(resolveAvailableModels("anthropic/claude-sonnet-5", availability)).toEqual(["a-group", "z-group"]);
+    });
+
     it("breaks ties between groups serving the same model deterministically, alphabetically", () => {
       const availability = buildModelAvailability(
         ["z-group", "a-group"],
diff --git a/ui/litellm-dashboard/src/lib/autorouter_presets.ts b/ui/litellm-dashboard/src/lib/autorouter_presets.ts
index f2df55fc310..02096cada41 100644
--- a/ui/litellm-dashboard/src/lib/autorouter_presets.ts
+++ b/ui/litellm-dashboard/src/lib/autorouter_presets.ts
@@ -159,16 +159,19 @@ export const deploymentRefsFromModelInfo = (
     return row.model_name && underlyingModels.length > 0 ? [{ modelGroup: row.model_name, underlyingModels }] : [];
   });
 
-export const resolveAvailableModel = (requiredModel: string, availability: ModelAvailability): string | undefined => {
+export const resolveAvailableModels = (requiredModel: string, availability: ModelAvailability): readonly string[] => {
   const { modelGroups, underlyingIndex } = availability;
-  if (modelGroups.has(requiredModel)) return requiredModel;
+  if (modelGroups.has(requiredModel)) return [requiredModel];
   const normalized = normalizeModelName(requiredModel);
-  const groupMatch = Array.from(modelGroups).find((available) => normalizeModelName(available) === normalized);
-  if (groupMatch !== undefined) return groupMatch;
+  const groupMatches = Array.from(modelGroups).filter((available) => normalizeModelName(available) === normalized);
+  if (groupMatches.length > 0) return groupMatches;
   const key = normalizeUnderlyingModel(requiredModel);
-  return key === null ? undefined : underlyingIndex.get(key)?.[0];
+  return key === null ? [] : underlyingIndex.get(key) ?? [];
 };
 
+export const resolveAvailableModel = (requiredModel: string, availability: ModelAvailability): string | undefined =>
+  resolveAvailableModels(requiredModel, availability)[0];
+
 export const getMissingModels = (
   config: Parameters<typeof getRequiredModels>[0],
   availability: ModelAvailability,
diff --git a/ui/litellm-dashboard/src/lib/http/schema.d.ts b/ui/litellm-dashboard/src/lib/http/schema.d.ts
index 83b0d58f2b2..29435c31aee 100644
--- a/ui/litellm-dashboard/src/lib/http/schema.d.ts
+++ b/ui/litellm-dashboard/src/lib/http/schema.d.ts
@@ -2110,12 +2110,17 @@ export interface paths {
          *     - claude plugin marketplace add <url>
          *     - claude plugin install <name>@<marketplace>
          *
+         *     Without `key` the catalog holds the enabled (public) plugins. With `?key=sk-...`
+         *     the key is authenticated and the catalog also holds the disabled plugins granted
+         *     to it through `object_permission.skills` on the key or its team.
+         *
          *     Returns:
          *         Marketplace catalog with list of available plugins and their git sources.
          *
          *     Example:
          *         ```bash
          *         claude plugin marketplace add http://localhost:4000/claude-code/marketplace.json
+         *         claude plugin marketplace add "http://localhost:4000/claude-code/marketplace.json?key=sk-..."
          *         claude plugin install my-plugin@litellm
          *         ```
          */
@@ -2152,8 +2157,8 @@ export interface paths {
          * @description Register a new plugin in the LiteLLM marketplace.
          *
          *     LiteLLM acts as a registry/discovery layer. Plugins are hosted on
-         *     GitHub/GitLab/Bitbucket. Claude Code will clone from the git source
-         *     when users install.
+         *     GitHub/GitLab/Bitbucket or as a zip archive on any https host (e.g. S3).
+         *     Claude Code clones the git source or downloads the archive when users install.
          *
          *     This endpoint is create-only and never overwrites. If a plugin with
          *     the same name already exists it returns 409 Conflict; use
@@ -2163,7 +2168,7 @@ export interface paths {
          *
          *     Parameters:
          *         - name: Plugin name (kebab-case)
-         *         - source: Git source reference (github, url, or git-subdir format)
+         *         - source: Plugin source reference (github, url, git-subdir, or archive format)
          *         - version: Semantic version (optional)
          *         - description: Plugin description (optional)
          *         - author: Author information (optional)
@@ -2229,7 +2234,7 @@ export interface paths {
          *
          *     Parameters:
          *         - plugin_name: Name of the plugin to update (path parameter)
-         *         - source: Git source reference (github, url, or git-subdir format)
+         *         - source: Plugin source reference (github, url, git-subdir, or archive format)
          *         - version: Semantic version (optional)
          *         - description: Plugin description (optional)
          *         - author: Author information (optional)
@@ -3318,11 +3323,14 @@ export interface paths {
          *     - model: Model name (e.g., "gpt-4", "claude-3-opus")
          *     - input_tokens: Expected input tokens per request
          *     - output_tokens: Expected output tokens per request
+         *     - cache_read_input_tokens: Cache-read tokens per request, counted within input_tokens (optional)
+         *     - cache_creation_input_tokens: Cache-write tokens per request, counted within input_tokens (optional)
+         *     - reasoning_tokens: Reasoning tokens per request, counted within output_tokens (optional)
          *     - num_requests_per_day: Number of requests per day (optional)
          *     - num_requests_per_month: Number of requests per month (optional)
          *
          *     Returns cost breakdown including:
-         *     - Per-request costs (input, output, margin)
+         *     - Per-request costs (input, output, margin, plus the cache-read, cache-write and reasoning shares)
          *     - Daily costs (if num_requests_per_day provided)
          *     - Monthly costs (if num_requests_per_month provided)
          *
@@ -3331,7 +3339,9 @@ export interface paths {
          *     {
          *         "model": "gpt-4",
          *         "input_tokens": 1000,
+         *         "cache_read_input_tokens": 800,
          *         "output_tokens": 500,
+         *         "reasoning_tokens": 200,
          *         "num_requests_per_day": 100,
          *         "num_requests_per_month": 3000
          *     }
@@ -23708,6 +23718,15 @@ export interface components {
             /** @description The decision record this request would have written to its log row */
             routing_decision: components["schemas"]["StandardLoggingRoutingDecision"];
         };
+        /** AwsSessionTag */
+        AwsSessionTag: {
+            /** Key */
+            Key: string;
+            /** Value */
+            Value: string;
+        } & {
+            [key: string]: unknown;
+        };
         /** BaseLitellmParams */
         BaseLitellmParams: {
             /**
@@ -25865,6 +25884,11 @@ export interface components {
              * @description If True, disables the optimistic per-request budget reservation introduced in v1.84.0. WARNING: This weakens hard budget enforcement. Without the reservation, a burst of concurrent requests from a single key can each pass the read-time spend check before any of them is charged, allowing a configured budget to be exceeded under high concurrency. Budgets are still evaluated on every request at read time, so an already-exhausted budget is still rejected. Enable only if your deployment is experiencing phantom BudgetExceededError responses caused by leaked reservations (see GitHub issue #27639). An INFO notice is logged once per worker at config load while this flag is active as a reminder that hard enforcement is relaxed.
              */
             disable_budget_reservation?: boolean | null;
+            /**
+             * Disable Env Credential Login
+             * @description If True, disables signing in to the Admin UI with the environment credentials: UI_USERNAME/UI_PASSWORD, or the master key when UI_PASSWORD is unset (that fallback means env-credential login is always live by default). Database users with passwords are unaffected. LOCKOUT RISK: create at least one proxy admin user with a password before enabling, or nobody can sign in to the UI. A locked-out admin can still administer the proxy over the API with the master key, and can unset this setting and restart the proxy to restore env-credential login. Default is False.
+             */
+            disable_env_credential_login?: boolean | null;
             /**
              * Disable Password Login When Sso Enabled
              * @description If True and SSO is configured (MICROSOFT_CLIENT_ID, GOOGLE_CLIENT_ID, GENERIC_CLIENT_ID, or SAML_IDP_METADATA_URL/XML), disables username/password login on /login, /v2/login, and /v3/login so SSO is the only way to reach the Admin UI. An admin locked out of the UI can still administer the proxy over the API with the master key; unset this setting and restart the proxy to restore UI username/password login. Default is False.
@@ -26347,6 +26371,31 @@ export interface components {
          *     independently of the response-cache backend in `litellm_settings.cache_params`.
          */
         CoordinationRedisParams: {
+            /**
+             * Aws Iam Auth
+             * @description enable AWS ElastiCache IAM authentication
+             */
+            aws_iam_auth?: boolean | string | null;
+            /**
+             * Aws Iam Cache Name
+             * @description AWS ElastiCache cache name
+             */
+            aws_iam_cache_name?: string | null;
+            /**
+             * Aws Iam Region
+             * @description AWS region for ElastiCache IAM authentication
+             */
+            aws_iam_region?: string | null;
+            /**
+             * Aws Iam Serverless
+             * @description the ElastiCache cache is serverless rather than a self-designed cluster
+             */
+            aws_iam_serverless?: boolean | string | null;
+            /**
+             * Aws Iam User Name
+             * @description AWS ElastiCache IAM user name
+             */
+            aws_iam_user_name?: string | null;
             /**
              * Host
              * @description Redis hostname
@@ -26468,6 +26517,18 @@ export interface components {
          * @description Request body for /cost/estimate endpoint.
          */
         CostEstimateRequest: {
+            /**
+             * Cache Creation Input Tokens
+             * @description Input tokens written to the prompt cache; counted within input_tokens
+             * @default 0
+             */
+            cache_creation_input_tokens: number;
+            /**
+             * Cache Read Input Tokens
+             * @description Input tokens read from the prompt cache; counted within input_tokens
+             * @default 0
+             */
+            cache_read_input_tokens: number;
             /**
              * Input Tokens
              * @description Expected input tokens per request
@@ -26493,17 +26554,65 @@ export interface components {
              * @description Expected output tokens per request
              */
             output_tokens: number;
+            /**
+             * Reasoning Tokens
+             * @description Reasoning tokens the model emits; counted within output_tokens
+             * @default 0
+             */
+            reasoning_tokens: number;
         };
         /**
          * CostEstimateResponse
          * @description Response body for /cost/estimate endpoint.
          */
         CostEstimateResponse: {
+            /**
+             * Cache Creation Cost Per Request
+             * @description Cache-write share of input_cost_per_request
+             * @default 0
+             */
+            cache_creation_cost_per_request: number;
+            /**
+             * Cache Creation Input Token Cost
+             * @description Rate billed per cache-write token
+             */
+            cache_creation_input_token_cost?: number | null;
+            /**
+             * Cache Creation Input Tokens
+             * @default 0
+             */
+            cache_creation_input_tokens: number;
+            /**
+             * Cache Read Cost Per Request
+             * @description Cache-read share of input_cost_per_request
+             * @default 0
+             */
+            cache_read_cost_per_request: number;
+            /**
+             * Cache Read Input Token Cost
+             * @description Rate billed per cache-read token
+             */
+            cache_read_input_token_cost?: number | null;
+            /**
+             * Cache Read Input Tokens
+             * @default 0
+             */
+            cache_read_input_tokens: number;
             /**
              * Cost Per Request
              * @description Total cost per request (includes margin)
              */
             cost_per_request: number;
+            /**
+             * Daily Cache Creation Cost
+             * @description Cache-write share of daily_input_cost
+             */
+            daily_cache_creation_cost?: number | null;
+            /**
+             * Daily Cache Read Cost
+             * @description Cache-read share of daily_input_cost
+             */
+            daily_cache_read_cost?: number | null;
             /**
              * Daily Cost
              * @description Total daily cost (includes margin)
@@ -26524,12 +26633,20 @@ export interface components {
              * @description Daily output token cost
              */
             daily_output_cost?: number | null;
+            /**
+             * Daily Reasoning Cost
+             * @description Reasoning share of daily_output_cost
+             */
+            daily_reasoning_cost?: number | null;
             /**
              * Input Cost Per Request
              * @description Input token cost per request (before margin)
              */
             input_cost_per_request: number;
-            /** Input Cost Per Token */
+            /**
+             * Input Cost Per Token
+             * @description Rate billed per input token
+             */
             input_cost_per_token?: number | null;
             /** Input Tokens */
             input_tokens: number;
@@ -26541,6 +26658,16 @@ export interface components {
             margin_cost_per_request: number;
             /** Model */
             model: string;
+            /**
+             * Monthly Cache Creation Cost
+             * @description Cache-write share of monthly_input_cost
+             */
+            monthly_cache_creation_cost?: number | null;
+            /**
+             * Monthly Cache Read Cost
+             * @description Cache-read share of monthly_input_cost
+             */
+            monthly_cache_read_cost?: number | null;
             /**
              * Monthly Cost
              * @description Total monthly cost (includes margin)
@@ -26561,21 +26688,45 @@ export interface components {
              * @description Monthly output token cost
              */
             monthly_output_cost?: number | null;
+            /**
+             * Monthly Reasoning Cost
+             * @description Reasoning share of monthly_output_cost
+             */
+            monthly_reasoning_cost?: number | null;
             /** Num Requests Per Day */
             num_requests_per_day?: number | null;
             /** Num Requests Per Month */
             num_requests_per_month?: number | null;
+            /**
+             * Output Cost Per Reasoning Token
+             * @description Rate billed per reasoning token
+             */
+            output_cost_per_reasoning_token?: number | null;
             /**
              * Output Cost Per Request
              * @description Output token cost per request (before margin)
              */
             output_cost_per_request: number;
-            /** Output Cost Per Token */
+            /**
+             * Output Cost Per Token
+             * @description Rate billed per output token
+             */
             output_cost_per_token?: number | null;
             /** Output Tokens */
             output_tokens: number;
             /** Provider */
             provider?: string | null;
+            /**
+             * Reasoning Cost Per Request
+             * @description Reasoning share of output_cost_per_request
+             * @default 0
+             */
+            reasoning_cost_per_request: number;
+            /**
+             * Reasoning Tokens
+             * @default 0
+             */
+            reasoning_tokens: number;
         };
         /** CreateCredentialItem */
         CreateCredentialItem: {
@@ -29212,6 +29363,8 @@ export interface components {
             models?: string[] | null;
             /** Search Tools */
             search_tools?: string[] | null;
+            /** Skills */
+            skills?: string[] | null;
             /** Vector Stores */
             vector_stores?: string[] | null;
         };
@@ -29265,6 +29418,8 @@ export interface components {
              * @default []
              */
             search_tools: string[] | null;
+            /** Skills */
+            skills?: string[] | null;
             /**
              * Vector Stores
              * @default []
@@ -29426,6 +29581,8 @@ export interface components {
             aws_secret_access_key?: string | null;
             /** Aws Session Name */
             aws_session_name?: string | null;
+            /** Aws Session Tags */
+            aws_session_tags?: components["schemas"]["AwsSessionTag"][] | null;
             /** Aws Session Token */
             aws_session_token?: string | null;
             /** Aws Sts Endpoint */
@@ -29629,6 +29786,8 @@ export interface components {
             output_cost_per_second_480p?: number | null;
             /** Output Cost Per Second 4K */
             output_cost_per_second_4k?: number | null;
+            /** Output Cost Per Second 720P */
+            output_cost_per_second_720p?: number | null;
             /** Output Cost Per Token */
             output_cost_per_token?: number | null;
             /** Output Cost Per Token Above 128K Tokens */
@@ -33513,7 +33672,7 @@ export interface components {
             name: string;
             /**
              * Source
-             * @description Git source reference
+             * @description Plugin source reference
              */
             source: {
                 [key: string]: string;
@@ -34762,7 +34921,7 @@ export interface components {
          * @description Request body for registering a plugin in the marketplace.
          *
          *     LiteLLM acts as a registry/discovery layer. Plugins are hosted on
-         *     GitHub/GitLab/Bitbucket and referenced by their git source.
+         *     GitHub/GitLab/Bitbucket or as a zip archive on any https host and referenced by their source.
          */
         RegisterPluginRequest: {
             /** @description Plugin author */
@@ -34804,10 +34963,11 @@ export interface components {
             namespace?: string | null;
             /**
              * Source
-             * @description Git source reference. Supported formats:
+             * @description Plugin source reference. Supported formats:
              *     - GitHub: {'source': 'github', 'repo': 'org/repo'}
              *     - Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}
              *     - Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}
+             *     - Zip archive on any https host (e.g. S3): {'source': 'archive', 'url': 'https://bucket.s3.amazonaws.com/plugin.zip', 'sha256': '<optional hex digest>'}
              */
             source: {
                 [key: string]: string;
@@ -34904,7 +35064,7 @@ export interface components {
             classification_prompt?: string | null;
             /**
              * Classifier Context Budget Chars
-             * @description Maximum characters of prior-turn text quoted to the LLM classifier, across the whole context window, per classification call. Turns are taken newest first and quoted whole while they fit, so a conversation small enough to quote entirely is never cut; once the budget runs out the older turns are dropped whole and only the turn straddling the boundary is truncated, into whatever space is left. The current ask and the caller's system prompt sit outside this budget and are always sent in full, as does the numbering each quoted turn carries. A budget under 120 leaves no room to quote a turn and suppresses the block; set classifier_context_window_size to 0 to turn context off deliberately. Only applies when classifier_type is 'llm'.
+             * @description Maximum characters of prior-turn text quoted to the LLM classifier, across the whole context window, per classification call. Turns are taken newest first and quoted whole while they fit, so a conversation small enough to quote entirely is never cut; once the budget runs out the older turns are dropped whole and only the turn straddling the boundary is truncated, into whatever space is left. The current ask and, except for Claude Code requests, the extracted system-role text sit outside this budget and are sent in full, as does the numbering each quoted turn carries. A budget under 120 leaves no room to quote a turn and suppresses the block; set classifier_context_window_size to 0 to turn context off deliberately. Only applies when classifier_type is 'llm'.
              * @default 8000
              */
             classifier_context_budget_chars: number;
@@ -34921,7 +35081,7 @@ export interface components {
             classifier_context_per_turn_chars?: number | null;
             /**
              * Classifier Context Window Size
-             * @description Number of prior user turns (tool output and harness reminders excluded) to include as context in the LLM classifier prompt, so a follow-up like 'now do the same for the streaming path' is classified against what it refers to. Counts turns of both roles when classifier_context_include_assistant_turns is enabled. These turns are sent to the classifier model, which may be a different deployment or provider than the routed completion model; that call already carries the current user ask and the caller's system prompt in full. Set to 0 to send neither prior turns nor any conversation context beyond the current ask. Only applies when classifier_type is 'llm'.
+             * @description Number of prior user turns (tool output and harness reminders excluded) to include as context in the LLM classifier prompt, so a follow-up like 'now do the same for the streaming path' is classified against what it refers to. Counts turns of both roles when classifier_context_include_assistant_turns is enabled. These turns are sent to the classifier model, which may be a different deployment or provider than the routed completion model; that call carries the current user ask and, except for Claude Code requests, the extracted system-role text in full. Claude Code system text is omitted to avoid classifying harness instructions; the routed completion still receives it. Set to 0 to send neither prior turns nor any conversation context beyond the current ask. Only applies when classifier_type is 'llm'.
              * @default 3
              */
             classifier_context_window_size: number;
@@ -35096,7 +35256,7 @@ export interface components {
             reasoning_override_min_score?: number | null;
             /**
              * Reminder Markers
-             * @description Override the delimiter pairs used to recognize and strip harness-injected reminder blocks before classification. A harness that wraps injected context differently per agent type (main, subagent, cron) lists every pair it emits. Replaces, rather than adds to, the built-in default of ('<system-reminder>', '</system-reminder>'), so a harness that also emits that pair lists it too. Matching is case-insensitive.
+             * @description Override the delimiter pairs used to recognize and strip harness-injected reminder blocks before classification. A harness that wraps injected context differently per agent type (main, subagent, cron) lists every pair it emits. Replaces, rather than adds to, the built-in system-reminder pair and the Codex envelope pairs enabled for Codex user agents, so list every built-in pair your harness also emits. Matching is case-insensitive.
              */
             reminder_markers?: components["schemas"]["ReminderMarkerPair"][] | null;
             /**
@@ -38086,10 +38246,11 @@ export interface components {
             namespace?: string | null;
             /**
              * Source
-             * @description Git source reference. Supported formats:
+             * @description Plugin source reference. Supported formats:
              *     - GitHub: {'source': 'github', 'repo': 'org/repo'}
              *     - Git URL: {'source': 'url', 'url': 'https://github.com/org/repo.git'}
              *     - Git Subdir: {'source': 'git-subdir', 'url': 'https://github.com/org/repo.git', 'path': 'plugins/plugin-name'}
+             *     - Zip archive on any https host (e.g. S3): {'source': 'archive', 'url': 'https://bucket.s3.amazonaws.com/plugin.zip', 'sha256': '<optional hex digest>'}
              */
             source: {
                 [key: string]: string;
@@ -39617,6 +39778,8 @@ export interface components {
             aws_secret_access_key?: string | null;
             /** Aws Session Name */
             aws_session_name?: string | null;
+            /** Aws Session Tags */
+            aws_session_tags?: components["schemas"]["AwsSessionTag"][] | null;
             /** Aws Session Token */
             aws_session_token?: string | null;
             /** Aws Sts Endpoint */
@@ -39820,6 +39983,8 @@ export interface components {
             output_cost_per_second_480p?: number | null;
             /** Output Cost Per Second 4K */
             output_cost_per_second_4k?: number | null;
+            /** Output Cost Per Second 720P */
+            output_cost_per_second_720p?: number | null;
             /** Output Cost Per Token */
             output_cost_per_token?: number | null;
             /** Output Cost Per Token Above 128K Tokens */
@@ -43075,7 +43240,9 @@ export interface operations {
     };
     get_marketplace_claude_code_marketplace_json_get: {
         parameters: {
-            query?: never;
+            query?: {
+                key?: string | null;
+            };
             header?: never;
             path?: never;
             cookie?: never;
@@ -43091,6 +43258,15 @@ export interface operations {
                     "application/json": unknown;
                 };
             };
+            /** @description Validation Error */
+            422: {
+                headers: {
+                    [name: string]: unknown;
+                };
+                content: {
+                    "application/json": components["schemas"]["HTTPValidationError"];
+                };
+            };
         };
     };
     list_plugins_claude_code_plugins_get: {
@@ -49283,7 +49459,7 @@ export interface operations {
         parameters: {
             query: {
                 /** @description Specify the service being hit. */
-                service: ("slack_budget_alerts" | "langfuse" | "langfuse_otel" | "slack" | "ms_teams" | "openmeter" | "webhook" | "email" | "braintrust" | "datadog" | "datadog_llm_observability" | "generic_api" | "arize" | "galileo" | "newrelic" | "sqs") | string;
+                service: ("slack_budget_alerts" | "langfuse" | "langfuse_otel" | "slack" | "ms_teams" | "openmeter" | "webhook" | "email" | "braintrust" | "datadog" | "datadog_llm_observability" | "generic_api" | "arize" | "galileo" | "newrelic" | "pointfive" | "sqs") | string;
             };
             header?: never;
             path?: never;
diff --git a/ui/litellm-dashboard/src/utils/entityLinks.test.ts b/ui/litellm-dashboard/src/utils/entityLinks.test.ts
index 47161a903ed..231413b213a 100644
--- a/ui/litellm-dashboard/src/utils/entityLinks.test.ts
+++ b/ui/litellm-dashboard/src/utils/entityLinks.test.ts
@@ -2,7 +2,29 @@ import { describe, expect, it, vi } from "vitest";
 
 vi.mock("@/components/networking", () => ({ serverRootPath: "" }));
 
-import { modelGroupHref } from "./entityLinks";
+import { modelGroupHref, teamDetailHref, userDetailHref } from "./entityLinks";
+
+describe("userDetailHref", () => {
+  it("targets the users page filtered to the encoded user id", () => {
+    expect(userDetailHref("user-1")).toMatch(/\/users\?user=user-1$/);
+    expect(userDetailHref("a b/c")).toMatch(/\?user=a%20b%2Fc$/);
+  });
+
+  it("returns no href for the proxy admin placeholder, which has no user page", () => {
+    expect(userDetailHref("default_user_id")).toBeUndefined();
+  });
+});
+
+describe("teamDetailHref", () => {
+  it("targets the teams page filtered to the encoded team id", () => {
+    expect(teamDetailHref("team-1")).toMatch(/\/teams\?team=team-1$/);
+    expect(teamDetailHref("a b/c")).toMatch(/\?team=a%20b%2Fc$/);
+  });
+
+  it("returns no href for the Admin UI session team, which has no team page", () => {
+    expect(teamDetailHref("litellm-dashboard")).toBeUndefined();
+  });
+});
 
 describe("modelGroupHref", () => {
   it("targets the models page filtered to the encoded model group", () => {
diff --git a/ui/litellm-dashboard/src/utils/entityLinks.ts b/ui/litellm-dashboard/src/utils/entityLinks.ts
index b8c70bdda48..33f2aa34976 100644
--- a/ui/litellm-dashboard/src/utils/entityLinks.ts
+++ b/ui/litellm-dashboard/src/utils/entityLinks.ts
@@ -1,3 +1,4 @@
+import { DEFAULT_PROXY_ADMIN_USER_ID, UI_TEAM_ID } from "@/utils/sentinels";
 import { uiHref } from "@/utils/uiHref";
 
 const MODEL_GRANT_SENTINELS: ReadonlySet<string> = new Set([
@@ -6,7 +7,8 @@ const MODEL_GRANT_SENTINELS: ReadonlySet<string> = new Set([
   "no-default-models",
 ]);
 
-export function teamDetailHref(teamId: string): string {
+export function teamDetailHref(teamId: string): string | undefined {
+  if (teamId === UI_TEAM_ID) return undefined;
   return `${uiHref("teams")}?team=${encodeURIComponent(teamId)}`;
 }
 
@@ -14,7 +16,8 @@ export function keyDetailHref(keyToken: string): string {
   return `${uiHref("api-keys")}?key=${encodeURIComponent(keyToken)}`;
 }
 
-export function userDetailHref(userId: string): string {
+export function userDetailHref(userId: string): string | undefined {
+  if (userId === DEFAULT_PROXY_ADMIN_USER_ID) return undefined;
   return `${uiHref("users")}?user=${encodeURIComponent(userId)}`;
 }
 
diff --git a/ui/litellm-dashboard/src/utils/sentinels.ts b/ui/litellm-dashboard/src/utils/sentinels.ts
new file mode 100644
index 00000000000..da6d09dfdd7
--- /dev/null
+++ b/ui/litellm-dashboard/src/utils/sentinels.ts
@@ -0,0 +1,3 @@
+export const DEFAULT_PROXY_ADMIN_USER_ID = "default_user_id";
+
+export const UI_TEAM_ID = "litellm-dashboard";
diff --git a/uv.lock b/uv.lock
index 0fe787645a2..cedc505acdf 100644
--- a/uv.lock
+++ b/uv.lock
@@ -10,7 +10,7 @@ resolution-markers = [
 ]
 
 [options]
-exclude-newer = "2026-09-06T00:40:30.433549Z"
+exclude-newer = "2026-09-07T23:09:03.362777Z"
 exclude-newer-span = "P3D"
 
 [manifest]
@@ -4772,7 +4772,7 @@ source = { editable = "enterprise" }
 
 [[package]]
 name = "litellm-proxy-extras"
-version = "0.4.95"
+version = "0.4.96"
 source = { editable = "litellm-proxy-extras" }
 
 [[package]]
diff --git a/whitelisted_bedrock_models.txt b/whitelisted_bedrock_models.txt
index 578edddec8d..6124cb41044 100644
--- a/whitelisted_bedrock_models.txt
+++ b/whitelisted_bedrock_models.txt
@@ -6,6 +6,7 @@ ai21.jamba-instruct-v1:0
 twelvelabs.pegasus-1-2-v1:0
 us.twelvelabs.pegasus-1-2-v1:0
 eu.twelvelabs.pegasus-1-2-v1:0
+global.twelvelabs.pegasus-1-2-v1:0
 amazon.titan-text-express-v1
 amazon.titan-text-lite-v1
 amazon.titan-text-premier-v1:0