Merge remote-tracking branch 'origin/main' into litellm_streaming_buffer_release_on_scan

.github/workflows/test-rust.yml

@@ -70,7 +70,7 @@ env:
 jobs:
   rust-lint:
     runs-on: ubuntu-latest
-    timeout-minutes: 10
+    timeout-minutes: 15
     defaults:
       run:
         working-directory: litellm-rust
@@ -81,24 +81,48 @@ jobs:
 
       - run: rustup toolchain install --no-self-update
 
-      - run: cargo fmt --check
+      - run: cargo fmt --all --check
 
-      - uses: actions/cache@0057852bfaa89a56745cba8c7296529d2fc39830 # v4.3.0
+      - uses: Swatinem/rust-cache@6323deb102c322ba6fcbdcafc7e3dddab59af2b6 # v2.9.2
         with:
-          path: |
-            ~/.cargo/registry
-            ~/.cargo/git
-            litellm-rust/target
-          key: ${{ runner.os }}-cargo-${{ github.job }}-${{ hashFiles('rust-toolchain.toml', '.cargo/**', 'litellm-rust/Cargo.lock') }}
-          restore-keys: |
-            ${{ runner.os }}-cargo-${{ github.job }}-
+          workspaces: litellm-rust
+          cache-on-failure: true
 
       - run: cargo clippy --workspace --all-targets --locked -- -D warnings
 
   rust-test:
     runs-on: ubuntu-latest
-    timeout-minutes: 30
+    timeout-minutes: 20
+    defaults:
+      run:
+        working-directory: litellm-rust
+    steps:
+      - uses: actions/checkout@08eba0b27e820071cde6df949e0beb9ba4906955 # v4.3.0
+        with:
+          persist-credentials: false
 
+      - uses: actions/setup-python@a26af69be951a213d495a4c3e4e4022e16d87065 # v5.6.0
+        with:
+          python-version: "3.12"
+
+      - run: rustup toolchain install --no-self-update
+
+      - uses: taiki-e/install-action@d438492cf8a250514fa2d34b30bc3c0dc37c65ff # v2.87.8
+        with:
+          tool: cargo-nextest@0.9.143
+
+      - uses: Swatinem/rust-cache@6323deb102c322ba6fcbdcafc7e3dddab59af2b6 # v2.9.2
+        with:
+          workspaces: litellm-rust
+          cache-on-failure: true
+
+      - run: cargo nextest run --workspace --locked
+
+      - run: cargo test --workspace --doc --locked
+
+  rust-wheel:
+    runs-on: ubuntu-latest
+    timeout-minutes: 30
     steps:
       - uses: actions/checkout@08eba0b27e820071cde6df949e0beb9ba4906955 # v4.3.0
         with:
@@ -114,18 +138,10 @@ jobs:
 
       - run: rustup toolchain install --no-self-update
 
-      - uses: actions/cache@0057852bfaa89a56745cba8c7296529d2fc39830 # v4.3.0
+      - uses: Swatinem/rust-cache@6323deb102c322ba6fcbdcafc7e3dddab59af2b6 # v2.9.2
         with:
-          path: |
-            ~/.cargo/registry
-            ~/.cargo/git
-            litellm-rust/target
-          key: ${{ runner.os }}-cargo-${{ github.job }}-${{ hashFiles('rust-toolchain.toml', '.cargo/**', 'litellm-rust/Cargo.lock') }}
-          restore-keys: |
-            ${{ runner.os }}-cargo-${{ github.job }}-
-
-      - run: cargo test --workspace --locked
-        working-directory: litellm-rust
+          workspaces: litellm-rust
+          cache-on-failure: true
 
       - run: uv build --wheel --out-dir dist
 

litellm-rust/crates/python-bridge/src/lifecycle/mod.rs

@@ -599,6 +599,34 @@ mod tests {
 
     static PYTHON_GLOBALS: Mutex<()> = Mutex::new(());
 
+    fn install_lifecycle_module(py: Python<'_>) -> Bound<'_, PyModule> {
+        py.run(
+            pyo3::ffi::c_str!(
+                r#"
+import sys
+import types
+
+sys.modules.setdefault('litellm', types.ModuleType('litellm'))
+sys.modules.setdefault('litellm.rust_bridge', types.ModuleType('litellm.rust_bridge'))
+"#
+            ),
+            None,
+            None,
+        )
+        .unwrap();
+        let source = std::ffi::CString::new(include_str!(
+            "../../../../../litellm/rust_bridge/lifecycle.py"
+        ))
+        .unwrap();
+        PyModule::from_code(
+            py,
+            &source,
+            pyo3::ffi::c_str!("lifecycle.py"),
+            pyo3::ffi::c_str!("litellm.rust_bridge.lifecycle"),
+        )
+        .unwrap()
+    }
+
     fn install_logging_worker(py: Python<'_>, worker: &Bound<'_, PyAny>) -> PyResult<()> {
         py.import("litellm.litellm_core_utils.logging_worker")?
             .setattr("GLOBAL_LOGGING_WORKER", worker)
@@ -773,17 +801,7 @@ mod tests {
             .unwrap_or_else(|error| error.into_inner());
         Python::initialize();
         Python::attach(|py| {
-            let source = std::ffi::CString::new(include_str!(
-                "../../../../../litellm/rust_bridge/lifecycle.py"
-            ))
-            .unwrap();
-            PyModule::from_code(
-                py,
-                &source,
-                pyo3::ffi::c_str!("lifecycle.py"),
-                pyo3::ffi::c_str!("litellm.rust_bridge.lifecycle"),
-            )
-            .unwrap();
+            install_lifecycle_module(py);
             let route = SyntheticRoute(
                 PythonCallState::new(
                     py,
@@ -819,17 +837,7 @@ mod tests {
         Python::initialize();
         Python::attach(|py| {
             py.import("asyncio").unwrap();
-            let source = std::ffi::CString::new(include_str!(
-                "../../../../../litellm/rust_bridge/lifecycle.py"
-            ))
-            .unwrap();
-            let module = PyModule::from_code(
-                py,
-                &source,
-                pyo3::ffi::c_str!("lifecycle.py"),
-                pyo3::ffi::c_str!("litellm.rust_bridge.lifecycle"),
-            )
-            .unwrap();
+            let module = install_lifecycle_module(py);
             let locals = PyDict::new(py);
             locals
                 .set_item("drive", module.getattr("drive").unwrap())

litellm-rust/crates/python-bridge/src/marshal.rs

@@ -190,6 +190,7 @@ mod tests {
 
     #[test]
     fn required_shapes_preserve_nested_values_and_existing_errors() {
+        Python::initialize();
         let nested = json!([{"role": "user", "content": [{"type": "text", "text": "hi"}]}]);
         assert_eq!(
             Value::Array(required_array("messages", nested.clone()).unwrap()),

litellm-rust/crates/token-counter/src/tiktoken.rs

@@ -195,14 +195,21 @@ mod tests {
     }
 
     #[test]
-    fn long_repeated_runs_stay_cheap() {
+    fn long_repeated_runs_cost_close_to_linear() {
         let ranks = ranks();
         let mut scratch = MergeScratch::default();
-        let piece = vec![b' '; 1 << 20];
-        let started = std::time::Instant::now();
-        let count = ranks.count_piece(&piece, &mut scratch);
-        assert!(count > 0);
-        assert!(started.elapsed().as_secs() < 5, "{:?}", started.elapsed());
+        let mut time = |len: usize| {
+            let piece = vec![b' '; len];
+            let started = std::time::Instant::now();
+            assert!(ranks.count_piece(&piece, &mut scratch) > 0);
+            started.elapsed()
+        };
+        let small = (0..3).map(|_| time(1 << 14)).min().unwrap();
+        let large = time(1 << 18);
+        assert!(
+            large < small * 64,
+            "{small:?} for 2^14 bytes, {large:?} for 2^18"
+        );
     }
 
     #[test]

litellm/integrations/opentelemetry.py

@@ -5,6 +5,7 @@ from collections.abc import Callable, Iterable, Mapping
 from concurrent.futures import ThreadPoolExecutor
 from dataclasses import dataclass, field
 from datetime import datetime
+from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, TypedDict, cast
 
 import litellm
@@ -20,7 +21,9 @@ from litellm.integrations.opentelemetry_utils.gen_ai_semconv import (
     OTELSemconvCategory,
     parse_semconv_opt_in,
 )
+from litellm.integrations.otel.model.baggage import promoted_metadata
 from litellm.integrations.otel.model.db_endpoint import db_span_attributes
+from litellm.integrations.otel.model.metadata import flatten_metadata
 from litellm.integrations.otel.model.semconv import Metric
 from litellm.litellm_core_utils.internal_call_metadata import is_unbilled_non_inference_call_from_params
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps
@@ -288,6 +291,7 @@ class OpenTelemetryConfig:
     # under ``litellm.team.metadata``. Empty by default so none of a team's
     # metadata leaves the process until explicitly allowlisted.
     baggage_team_metadata_keys: list[str] = field(default_factory=list)
+    baggage_metadata_keys: list[str] = field(default_factory=list)
     # Prometheus-style include/exclude control over which attributes are stamped
     # on emitted metrics, to cap metric cardinality.
     attributes: OTELMetricAttributeFilter | None = None
@@ -314,6 +318,9 @@ class OpenTelemetryConfig:
         self.baggage_team_metadata_keys = _normalize_team_metadata_keys(
             self.baggage_team_metadata_keys
         ) or _normalize_team_metadata_keys(os.getenv("LITELLM_OTEL_BAGGAGE_TEAM_METADATA_KEYS"))
+        self.baggage_metadata_keys = _normalize_team_metadata_keys(
+            self.baggage_metadata_keys
+        ) or _normalize_team_metadata_keys(os.getenv("LITELLM_OTEL_BAGGAGE_METADATA_KEYS"))
 
     @classmethod
     def from_env(cls):
@@ -366,11 +373,14 @@ class OpenTelemetry(OTELGenAISemconvMixin, CustomLogger):
         **kwargs,
     ):
         team_metadata_keys_override: Final = kwargs.pop("baggage_team_metadata_keys", None)
+        metadata_keys_override: Final = kwargs.pop("baggage_metadata_keys", None)
         metric_attributes_override: Final = kwargs.pop("attributes", None)
         if config is None:
             config = OpenTelemetryConfig.from_env()
         if team_metadata_keys_override is not None:
             config.baggage_team_metadata_keys = _normalize_team_metadata_keys(team_metadata_keys_override)
+        if metadata_keys_override is not None:
+            config.baggage_metadata_keys = _normalize_team_metadata_keys(metadata_keys_override)
         if metric_attributes_override is not None:
             config.attributes = _build_metric_attribute_filter(metric_attributes_override)
 
@@ -1542,6 +1552,11 @@ class OpenTelemetry(OTELGenAISemconvMixin, CustomLogger):
         if team_metadata:
             self.safe_set_attribute(span=span, key=TEAM_METADATA_ATTRIBUTE, value=team_metadata)
 
+        if self.config.baggage_metadata_keys:
+            flat_metadata: Final = MappingProxyType(dict(flatten_metadata(metadata)))
+            for key, value in promoted_metadata(flat_metadata, tuple(self.config.baggage_metadata_keys)).items():
+                self.safe_set_attribute(span=span, key=key, value=value)
+
         model_group: Final = standard_logging_payload.get("model_group")
         if model_group:
             self.safe_set_attribute(span=span, key=MODEL_GROUP_ATTRIBUTE, value=model_group)

litellm/integrations/otel/logger.py

@@ -33,6 +33,7 @@ from litellm.integrations.otel.model.metadata import (
     LLMCallEvent,
     RequestIdentity,
     auth_metadata,
+    metadata_from_request_data,
     model_from_request_data,
 )
 from litellm.integrations.otel.model.payloads import (
@@ -679,7 +680,12 @@ class OpenTelemetryV2(CustomLogger):
     #  / errors are the FastAPI instrumentor's job, so we don't touch it here.
     # ====================================================================== #
 
-    def seed_request_identity(self, user_api_key_dict: object, model: str | None = None) -> None:
+    def seed_request_identity(
+        self,
+        user_api_key_dict: object,
+        model: str | None = None,
+        request_metadata: Mapping[str, object] | None = None,
+    ) -> None:
         """Attach request-identity Baggage to the current context + server span.
 
         Seeding identity into Baggage makes **every** span emitted afterwards for
@@ -691,7 +697,7 @@ class OpenTelemetryV2(CustomLogger):
         isn't determined yet, which is correct.
         """
         try:
-            identity: Final = RequestIdentity.from_user_api_key_auth(user_api_key_dict)
+            identity: Final = RequestIdentity.from_user_api_key_auth(user_api_key_dict, request_metadata)
             bag: Final = promoted_baggage(
                 identity,
                 model,
@@ -743,6 +749,7 @@ class OpenTelemetryV2(CustomLogger):
         self.seed_request_identity(
             user_api_key_dict,
             model=model_from_request_data(data),
+            request_metadata=metadata_from_request_data(data),
         )
         return data
 

litellm/integrations/otel/model/baggage.py

@@ -15,9 +15,10 @@ never promoted whole.
 
 import json
 from collections.abc import Callable, Mapping
+from types import MappingProxyType
 from typing import Final
 
-from litellm.integrations.otel.model.metadata import RequestIdentity
+from litellm.integrations.otel.model.metadata import REQUESTER_METADATA_PATH, RequestIdentity
 from litellm.integrations.otel.model.semconv import GenAI, LiteLLM
 
 # Attribute key -> value extractor over (identity, request_model,
@@ -79,17 +80,23 @@ def promoted_baggage(
     ``team_metadata_keys`` selects sub-keys of the team's metadata to promote
     under ``litellm.team.metadata``. Empty values are dropped.
     """
-    out: Final[dict[str, str]] = {}
-    for key, extract in _PROMOTABLE.items():
-        if key in promoted_keys:
-            value = extract(identity, request_model, team_metadata_keys)
-            if value:
-                out[key] = value
-    for meta_key in metadata_keys:
-        value = identity.metadata.get(meta_key)
-        if value:
-            out[f"{LiteLLM.METADATA_PREFIX}{meta_key}"] = value
-    return out
+    identity_values: Final = {
+        key: value
+        for key, extract in _PROMOTABLE.items()
+        if key in promoted_keys and (value := extract(identity, request_model, team_metadata_keys))
+    }
+    return {**identity_values, **promoted_metadata(identity.metadata, metadata_keys)}
+
+
+def promoted_metadata(metadata: Mapping[str, str], metadata_keys: tuple[str, ...]) -> Mapping[str, str]:
+    """Allowlisted entries of a flattened metadata mapping under ``litellm.metadata.*``."""
+    return MappingProxyType(
+        {
+            f"{LiteLLM.METADATA_PREFIX}{meta_key.removeprefix(REQUESTER_METADATA_PATH)}": value
+            for meta_key in metadata_keys
+            if (value := metadata.get(meta_key))
+        }
+    )
 
 
 def _filtered_team_metadata_json(

litellm/integrations/otel/model/config.py

@@ -210,7 +210,10 @@ class OpenTelemetryV2Config(BaseSettings):
         validation_alias=AliasChoices("baggage_metadata_keys", "LITELLM_OTEL_BAGGAGE_METADATA_KEYS"),
         description=(
             "Metadata sub-keys promoted under the ``litellm.metadata.*`` "
-            "namespace. Configure via the ``LITELLM_OTEL_BAGGAGE_METADATA_KEYS`` "
+            "namespace. A dotted path such as ``requester_metadata.trace_id`` "
+            "reads the caller's nested ``metadata.trace_id`` and is promoted as "
+            "``litellm.metadata.trace_id``; other dotted keys keep their full path. "
+            "Configure via the ``LITELLM_OTEL_BAGGAGE_METADATA_KEYS`` "
             "env var (comma-separated) or "
             "``callback_settings.otel.baggage_metadata_keys`` in config.yaml."
         ),

litellm/integrations/otel/model/metadata.py

@@ -49,6 +49,8 @@ if TYPE_CHECKING:
     from litellm.types.utils import StandardLoggingPayload
 
 LANGFUSE_TRACE_NAME_HEADER: Final = "langfuse_trace_name"
+REQUESTER_METADATA_KEY: Final = "requester_metadata"
+REQUESTER_METADATA_PATH: Final = f"{REQUESTER_METADATA_KEY}."
 
 
 @dataclass(frozen=True)
@@ -78,7 +80,7 @@ class RequestIdentity:
         model, not just the user-facing one.
         """
         raw_meta: Final = cast(Mapping[str, object], payload.get("metadata") or {})
-        metadata = {key: str(value) for key, value in raw_meta.items() if isinstance(value, (str, bool, int, float))}
+        metadata: Final = MappingProxyType(dict(flatten_metadata(raw_meta)))
         return cls(
             call_id=as_str(payload.get("litellm_call_id")) or as_str(payload.get("id")),
             # StandardLoggingMetadata's canonical key is ``user_api_key_team_id``;
@@ -95,7 +97,9 @@ class RequestIdentity:
         )
 
     @classmethod
-    def from_user_api_key_auth(cls, auth: object) -> RequestIdentity:
+    def from_user_api_key_auth(
+        cls, auth: object, request_metadata: Mapping[str, object] | None = None
+    ) -> RequestIdentity:
         """Identity from a ``UserAPIKeyAuth`` (duck-typed to keep this module
         free of a proxy import).
 
@@ -103,11 +107,13 @@ class RequestIdentity:
         guardrail, or service span is created — so the whole request's spans
         inherit identity, not just the LLM-call span. Metadata sub-keys use the
         ``user_api_key_*`` names that ``baggage.DEFAULT_BAGGAGE_METADATA_KEYS``
-        promotes.
+        promotes; ``request_metadata`` (the caller's ``requester_metadata``
+        snapshot) is flattened to dotted keys so ``requester_metadata.<key>``
+        resolves too.
         """
         get: Final = lambda name: getattr(auth, name, None)  # noqa: E731
-        metadata: Final = {
-            meta_key: str(value)
+        auth_meta: Final = tuple(
+            (meta_key, str(value))
             for meta_key, attr in (
                 ("user_api_key_user_id", "user_id"),
                 ("user_api_key_org_id", "org_id"),
@@ -115,7 +121,9 @@ class RequestIdentity:
                 ("user_api_key_end_user_id", "end_user_id"),
             )
             if (value := get(attr))
-        }
+        )
+        request_meta: Final = flatten_metadata(request_metadata) if request_metadata is not None else ()
+        metadata: Final = MappingProxyType(dict((*request_meta, *auth_meta)))
         return cls(
             team_id=as_str(get("team_id")),
             team_alias=as_str(get("team_alias")),
@@ -351,6 +359,35 @@ def model_from_request_data(data: object) -> str | None:
     return None
 
 
+def metadata_from_request_data(data: object) -> Mapping[str, object] | None:
+    """The caller's ``requester_metadata`` snapshot from a pre-call ``data`` dict, keyed under its wrapper.
+
+    The proxy stores it under ``metadata`` or ``litellm_metadata`` depending on the route;
+    the proxy-owned siblings (``user_api_key_*``, ``requester_ip_address``) are not read.
+    """
+    top: Final = _as_str_mapping(data)
+    if top is None:
+        return None
+    snapshots: Final = tuple(
+        snapshot
+        for name in ("metadata", "litellm_metadata")
+        if (nested := _as_str_mapping(top.get(name))) is not None
+        and (snapshot := _as_str_mapping(nested.get(REQUESTER_METADATA_KEY))) is not None
+    )
+    return MappingProxyType({REQUESTER_METADATA_KEY: snapshots[0]}) if snapshots else None
+
+
+def flatten_metadata(raw: Mapping[str, object]) -> Iterator[tuple[str, str]]:
+    """Scalar leaves of a nested metadata mapping, keyed by their dotted path."""
+    stack: Final = list(tuple(raw.items())[::-1])  # mutable-ok: iterative worklist keeps the walk off the call stack
+    while stack:
+        key, value = stack.pop()
+        if (nested := _as_str_mapping(value)) is not None:
+            stack.extend(tuple((f"{key}.{sub_key}", sub_value) for sub_key, sub_value in nested.items())[::-1])
+        elif isinstance(value, (str, bool, int, float)):
+            yield key, str(value)
+
+
 def resolve_provider_model(payload: StandardLoggingPayload) -> str | None:
     """The model litellm dispatched to the provider, from the payload.
 

litellm/llms/bedrock/vector_stores/transformation.py

@@ -1,3 +1,4 @@
+from collections.abc import Mapping
 from copy import deepcopy
 from typing import TYPE_CHECKING, Any, Final, cast
 from urllib.parse import urlparse
@@ -14,6 +15,7 @@ from litellm.types.integrations.rag.bedrock_knowledgebase import (
     BedrockKBResponse,
     BedrockKBRetrievalConfiguration,
     BedrockKBRetrievalQuery,
+    BedrockKBUserContext,
 )
 from litellm.types.router import GenericLiteLLMParams
 from litellm.types.vector_stores import (
@@ -242,10 +244,29 @@ class BedrockVectorStoreConfig(BaseVectorStoreConfig, BaseAWSLLM):
             retrieval_config.setdefault("vectorSearchConfiguration", {})["filter"] = filters
         if retrieval_config:
             request_body["retrievalConfiguration"] = cast(BedrockKBRetrievalConfiguration, retrieval_config)
+        user_context: Final = self._user_context(extra_body=extra_body, litellm_params=litellm_params)
+        if user_context is not None:
+            request_body["userContext"] = user_context
 
         litellm_logging_obj.model_call_details["query"] = query
         return url, request_body
 
+    @staticmethod
+    def _user_context(
+        extra_body: Mapping[str, object] | None, litellm_params: Mapping[str, object]
+    ) -> BedrockKBUserContext | None:
+        sources: Final = tuple(source for source in (extra_body, litellm_params) if isinstance(source, Mapping))
+        found: Final = next(
+            (
+                source[key]
+                for source in sources
+                for key in ("userContext", "user_context")
+                if source.get(key) is not None
+            ),
+            None,
+        )
+        return None if found is None else cast(BedrockKBUserContext, found)
+
     def sign_request(
         self,
         headers: dict,

litellm/llms/fireworks_ai/chat/transformation.py

@@ -49,6 +49,17 @@ if TYPE_CHECKING:
     import tiktoken
 
 
+def _map_reasoning_effort(value: object) -> object:
+    effort: Final[object] = cast(Mapping[str, object], value).get("effort") if isinstance(value, Mapping) else value
+    if effort is True:
+        return "medium"
+    if effort is False:
+        return "none"
+    if effort == "auto":
+        return None
+    return effort
+
+
 def _extract_fireworks_hidden_params(payload: dict) -> dict:
     """
     Collect Fireworks-specific response fields (perf_metrics, prompt_token_ids,
@@ -327,12 +338,9 @@ class FireworksAIConfig(FireworksAIMixin, OpenAIGPTConfig):
             elif param == "max_completion_tokens":
                 optional_params["max_tokens"] = value
             elif param == "reasoning_effort":
-                if value is True:
-                    optional_params["reasoning_effort"] = "medium"
-                elif value is False:
-                    optional_params["reasoning_effort"] = "none"
-                elif value != "auto":
-                    optional_params["reasoning_effort"] = value
+                effort = _map_reasoning_effort(value)
+                if effort is not None:
+                    optional_params["reasoning_effort"] = effort
             elif param in supported_openai_params:
                 if value is not None:
                     optional_params[param] = value

litellm/proxy/auth/user_api_key_auth.py

@@ -2571,6 +2571,13 @@ def _token_can_vouch_for_team(valid_token: UserAPIKeyAuth, lookup_error: BaseExc
     return PrismaDBExceptionHandler.should_allow_request_on_db_unavailable()
 
 
+def is_no_auth_dev_mode(master_key: str | None, general_settings: Mapping[str, object]) -> bool:
+    return master_key is None and not any(
+        general_settings.get(flag, False)
+        for flag in ("enable_jwt_auth", "enable_oauth2_auth", "enable_oauth2_proxy_auth")
+    )
+
+
 @tracer.wrap()
 async def _run_centralized_common_checks(
     user_api_key_auth_obj: UserAPIKeyAuth,
@@ -2630,11 +2637,7 @@ async def _run_centralized_common_checks(
     # Running common_checks would block every admin route on these
     # deployments where that was previously not the contract. If any
     # authn is enabled (JWT, OAuth2, OAuth2-proxy), authz must run.
-    if master_key is None and not (
-        general_settings.get("enable_jwt_auth", False)
-        or general_settings.get("enable_oauth2_auth", False)
-        or general_settings.get("enable_oauth2_proxy_auth", False)
-    ):
+    if is_no_auth_dev_mode(master_key, general_settings):
         return
 
     if user_custom_auth is not None and not general_settings.get("custom_auth_run_common_checks", False):

litellm/proxy/hooks/key_management_event_hooks.py

@@ -21,6 +21,7 @@ from litellm.proxy._types import (
     UserAPIKeyAuth,
 )
 from litellm.proxy.utils import _hash_token_if_needed
+from litellm.secret_managers.base_secret_manager import BaseSecretManager
 
 # NOTE: This is the prefix for all virtual keys stored in AWS Secrets Manager
 LITELLM_PREFIX_STORED_VIRTUAL_KEYS: Final = "litellm/"
@@ -100,6 +101,7 @@ class KeyManagementEventHooks:
         Post /key/update processing hook
 
         Handles the following:
+        - Renaming the key's secret in the secret manager when the alias changes
         - Storing Audit Logs for key update
         """
         from litellm.proxy.management_helpers.audit_logs import (
@@ -109,6 +111,16 @@ class KeyManagementEventHooks:
         )
         from litellm.proxy.proxy_server import litellm_proxy_admin_name
 
+        if data.key_alias is not None and data.key_alias != existing_key_row.key_alias:
+            try:
+                await KeyManagementEventHooks._rename_virtual_key_in_secret_manager(
+                    current_secret_name=existing_key_row.key_alias or f"virtual-key-{existing_key_row.token}",
+                    new_secret_name=data.key_alias,
+                    team_id=existing_key_row.team_id,
+                )
+            except Exception as e:
+                verbose_proxy_logger.warning("Failed to rename virtual key in secret manager: %s", e)
+
         if is_audit_logging_enabled():
             updated_fields: Final = {
                 **data.model_dump(exclude_none=True),
@@ -153,10 +165,11 @@ class KeyManagementEventHooks:
         from litellm.proxy.proxy_server import litellm_proxy_admin_name
 
         # Store the generated key in the secret manager - non-blocking, independent operation
-        if data is not None and response.token_id is not None:
+        if response.token_id is not None:
             try:
                 initial_secret_name: Final = existing_key_row.key_alias or f"virtual-key-{existing_key_row.token}"
-                new_secret_name: Final = response.key_alias or data.key_alias or initial_secret_name
+                requested_alias: Final = data.key_alias if data is not None else None
+                new_secret_name: Final = response.key_alias or requested_alias or initial_secret_name
                 verbose_proxy_logger.info(
                     "Updating secret in secret manager: secret_name=%s",
                     new_secret_name,
@@ -305,21 +318,66 @@ class KeyManagementEventHooks:
             new_secret_value: New value of the virtual key (example: sk-1234)
             team_id: Optional team ID to get team-specific secret manager settings
         """
-        if litellm._key_management_settings is not None:
-            if litellm._key_management_settings.store_virtual_keys is True:
-                from litellm.secret_managers.base_secret_manager import (
-                    BaseSecretManager,
-                )
+        secret_manager: Final = KeyManagementEventHooks._stored_virtual_key_secret_manager()
+        if secret_manager is None:
+            return
+        optional_params: Final = await KeyManagementEventHooks._get_secret_manager_optional_params(team_id)
+        await secret_manager.async_rotate_secret(
+            current_secret_name=KeyManagementEventHooks._get_secret_name(current_secret_name),
+            new_secret_name=KeyManagementEventHooks._get_secret_name(new_secret_name),
+            new_secret_value=new_secret_value,
+            optional_params=optional_params,
+        )
 
-                # store the key in the secret manager
-                if isinstance(litellm.secret_manager_client, BaseSecretManager):
-                    optional_params: Final = await KeyManagementEventHooks._get_secret_manager_optional_params(team_id)
-                    await litellm.secret_manager_client.async_rotate_secret(
-                        current_secret_name=KeyManagementEventHooks._get_secret_name(current_secret_name),
-                        new_secret_name=KeyManagementEventHooks._get_secret_name(new_secret_name),
-                        new_secret_value=new_secret_value,
-                        optional_params=optional_params,
-                    )
+    @staticmethod
+    def _stored_virtual_key_secret_manager() -> BaseSecretManager | None:
+        """
+        The secret manager client that stores virtual keys, or None when virtual keys are not stored in one
+        """
+        if litellm._key_management_settings is None or litellm._key_management_settings.store_virtual_keys is not True:
+            return None
+        if not isinstance(litellm.secret_manager_client, BaseSecretManager):
+            return None
+        return litellm.secret_manager_client
+
+    @staticmethod
+    async def _rename_virtual_key_in_secret_manager(
+        current_secret_name: str,
+        new_secret_name: str,
+        team_id: str | None = None,
+    ) -> None:
+        """
+        Move a virtual key to a new secret name, keeping its current value
+
+        Args:
+            current_secret_name: Current name of the virtual key
+            new_secret_name: New name of the virtual key
+            team_id: Optional team ID to get team-specific secret manager settings
+        """
+        secret_manager: Final = KeyManagementEventHooks._stored_virtual_key_secret_manager()
+        if secret_manager is None:
+            return
+        optional_params: Final = await KeyManagementEventHooks._get_secret_manager_optional_params(team_id)
+        current_secret_value: Final = await secret_manager.async_read_secret(
+            secret_name=KeyManagementEventHooks._get_secret_name(current_secret_name),
+            optional_params=optional_params,
+        )
+        if current_secret_value is None:
+            verbose_proxy_logger.warning(
+                "Secret %s not found in secret manager, skipping rename to %s", current_secret_name, new_secret_name
+            )
+            return
+        verbose_proxy_logger.info(
+            "Renaming secret in secret manager: current_secret_name=%s new_secret_name=%s",
+            current_secret_name,
+            new_secret_name,
+        )
+        await secret_manager.async_rotate_secret(
+            current_secret_name=KeyManagementEventHooks._get_secret_name(current_secret_name),
+            new_secret_name=KeyManagementEventHooks._get_secret_name(new_secret_name),
+            new_secret_value=current_secret_value,
+            optional_params=optional_params,
+        )
 
     @staticmethod
     def _get_secret_name(secret_name: str) -> str:

litellm/proxy/pass_through_endpoints/llm_passthrough_endpoints.py

@@ -45,6 +45,7 @@ from litellm.proxy.auth.handle_jwt import JWTHandler
 from litellm.proxy.auth.route_checks import RouteChecks
 from litellm.proxy.auth.user_api_key_auth import (
     _get_bearer_token,
+    is_no_auth_dev_mode,
     user_api_key_auth,
     user_api_key_auth_websocket,
 )
@@ -709,8 +710,7 @@ async def anthropic_proxy_route(
     endpoint_func: Final = create_pass_through_route(
         endpoint=endpoint,
         target=str(updated_url),
-        custom_headers=auth_header if auth_header is not None else {},
-        _forward_headers=True,
+        custom_headers=_upstream_headers_for_anthropic_route(request, user_api_key_dict, auth_header),
         is_streaming_request=is_streaming_request,
     )  # dynamically construct pass-through endpoint based on incoming path
     received_value: Final = await endpoint_func(
@@ -1989,6 +1989,19 @@ _HEADERS_NEVER_FORWARDED_TO_VERTEX: Final = frozenset({"content-length", "host"}
     SpecialHeaders.litellm_credential_header_names() - _VERTEX_UPSTREAM_CREDENTIAL_HEADERS
 )
 
+_CREDENTIALLESS_ANTHROPIC_MISSING_CREDENTIAL_DETAIL: Final = (
+    "No Anthropic credential is configured on this proxy and the request carried no upstream "
+    "Anthropic credential. The LiteLLM virtual key is not forwarded to Anthropic. Configure an "
+    "Anthropic credential (ANTHROPIC_API_KEY or ANTHROPIC_AUTH_TOKEN, or a model with "
+    "use_in_pass_through: true), or send your own Anthropic API key in the x-api-key header or "
+    "your own Anthropic OAuth token in the Authorization header."
+)
+
+_ANTHROPIC_UPSTREAM_CREDENTIAL_HEADERS: Final = frozenset({"authorization", "x-api-key"})
+_HEADERS_NEVER_FORWARDED_TO_ANTHROPIC: Final = frozenset({"content-length", "host", "accept-encoding"}) | (
+    SpecialHeaders.litellm_credential_header_names() - _ANTHROPIC_UPSTREAM_CREDENTIAL_HEADERS
+)
+
 
 _MAPPED_ROUTE_CALLER_KEY_HEADER: Final = "litellm_user_api_key"
 
@@ -2026,8 +2039,11 @@ def _is_authenticated_caller_jwt(value: str, jwt_claims: Mapping[str, object]) -
 
 
 def _is_authenticated_caller_secret(value: str, user_api_key_dict: UserAPIKeyAuth) -> bool:
-    """Whether a header value is the master key, the JWT that authenticated, or the key stored as ``api_key``."""
-    from litellm.proxy.proxy_server import master_key
+    """Whether a header value is the master key, the JWT that authenticated, or the key stored as ``api_key``.
+
+    A proxy in no-auth dev mode without custom auth authenticated nothing, so none of the caller's values is one.
+    """
+    from litellm.proxy.proxy_server import general_settings, master_key, user_custom_auth
 
     normalized: Final = _normalize_credential_value(value)
     if master_key is not None and hmac.compare_digest(normalized.encode(), master_key.encode()):
@@ -2035,35 +2051,54 @@ def _is_authenticated_caller_secret(value: str, user_api_key_dict: UserAPIKeyAut
     jwt_claims: Final = user_api_key_dict.jwt_claims
     if jwt_claims and _is_authenticated_caller_jwt(normalized, jwt_claims):
         return True
+    if is_no_auth_dev_mode(master_key, general_settings) and user_custom_auth is None:
+        return False
     authenticated_key: Final = user_api_key_dict.api_key
     if authenticated_key is None:
         return False
-    if master_key is None and not normalized.startswith("sk-"):
-        return False
     stored_representation: Final = UserAPIKeyAuth._safe_hash_litellm_api_key(normalized)  # pyright: ignore[reportPrivateUsage]  # the exact transform auth applied when it stored api_key
     return hmac.compare_digest(stored_representation.encode(), authenticated_key.encode())
 
 
+def _caller_headers_without_litellm_secrets(
+    request: Request, user_api_key_dict: UserAPIKeyAuth, never_forwarded: frozenset[str]
+) -> Mapping[str, str]:
+    incoming: Final = _safe_get_request_headers(request)
+    dropped_by_name: Final = never_forwarded.union(
+        (_MAPPED_ROUTE_CALLER_KEY_HEADER, *_operator_configured_caller_key_header_names())
+    )
+    return MappingProxyType(
+        {
+            name: value
+            for name, value in incoming.items()
+            if name not in dropped_by_name and not _is_authenticated_caller_secret(value, user_api_key_dict)
+        }
+    )
+
+
 def _forwarded_headers_for_credentialless_vertex_passthrough(
     request: Request, user_api_key_dict: UserAPIKeyAuth
 ) -> Mapping[str, str]:
     """Caller headers to forward on the bring-your-own-credentials Vertex branch, minus LiteLLM secrets."""
-    incoming: Final = _safe_get_request_headers(request)
-    never_forwarded: Final = _HEADERS_NEVER_FORWARDED_TO_VERTEX.union(
-        (_MAPPED_ROUTE_CALLER_KEY_HEADER, *_operator_configured_caller_key_header_names())
+    forwarded: Final = _caller_headers_without_litellm_secrets(
+        request, user_api_key_dict, _HEADERS_NEVER_FORWARDED_TO_VERTEX
     )
-    forwarded: Final = MappingProxyType(
-        {
-            name: value
-            for name, value in incoming.items()
-            if name not in never_forwarded and not _is_authenticated_caller_secret(value, user_api_key_dict)
-        }
-    )
-    if "authorization" not in forwarded and "x-goog-api-key" not in forwarded:
+    if _VERTEX_UPSTREAM_CREDENTIAL_HEADERS.isdisjoint(forwarded):
         raise HTTPException(status_code=401, detail=_CREDENTIALLESS_VERTEX_MISSING_CREDENTIAL_DETAIL)
     return forwarded
 
 
+def _upstream_headers_for_anthropic_route(
+    request: Request, user_api_key_dict: UserAPIKeyAuth, proxy_auth_header: Mapping[str, str] | None
+) -> Mapping[str, str]:
+    caller_headers: Final = _caller_headers_without_litellm_secrets(
+        request, user_api_key_dict, _HEADERS_NEVER_FORWARDED_TO_ANTHROPIC
+    )
+    if proxy_auth_header is None and _ANTHROPIC_UPSTREAM_CREDENTIAL_HEADERS.isdisjoint(caller_headers):
+        raise HTTPException(status_code=401, detail=_CREDENTIALLESS_ANTHROPIC_MISSING_CREDENTIAL_DETAIL)
+    return MappingProxyType({**caller_headers, **(proxy_auth_header or {})})
+
+
 async def _prepare_vertex_auth_headers(
     request: Request,
     vertex_credentials: VertexPassThroughCredentials | None,

litellm/types/integrations/rag/bedrock_knowledgebase.py

@@ -1,6 +1,6 @@
 from typing import Any, Literal
 
-from typing_extensions import TypedDict
+from typing_extensions import ReadOnly, TypedDict
 
 
 class BedrockKBLocation(TypedDict, total=False):
@@ -127,6 +127,10 @@ class BedrockKBGuardrailConfiguration(TypedDict, total=False):
     guardrailVersion: str | None
 
 
+class BedrockKBUserContext(TypedDict):
+    userId: ReadOnly[str]
+
+
 class BedrockKBRequest(TypedDict, total=False):
     """Complete request structure for Bedrock Knowledge Base retrieval."""
 
@@ -134,6 +138,7 @@ class BedrockKBRequest(TypedDict, total=False):
     nextToken: str | None
     retrievalConfiguration: BedrockKBRetrievalConfiguration | None
     retrievalQuery: BedrockKBRetrievalQuery
+    userContext: ReadOnly[BedrockKBUserContext | None]
 
 
 #########################################################################

tests/test_litellm/integrations/otel/test_otel_v2_baggage.py

@@ -168,6 +168,46 @@ def test_allowlisted_metadata_subkey_promoted_blob_excluded():
     assert all("private_note" not in k for k in span.attributes)
 
 
+def test_nested_metadata_key_promoted_under_caller_path():
+    """A dotted allowlist entry reads the nested caller metadata the proxy stores
+    under ``requester_metadata`` and lands on the LLM-call span under the caller's
+    own path (``litellm.metadata.trace_id``, ``litellm.metadata.nested.deep``);
+    a pre-existing flat dotted key keeps its full name, and unlisted siblings and
+    the blob stay out."""
+    engine, exporter = _engine_and_exporter()
+    payload = _payload()
+    payload["metadata"]["a.b"] = "flat"
+    payload["metadata"]["requester_metadata"] = {
+        "trace_id": "abc",
+        "attempt": 0,
+        "empty": "",
+        "nested": {"deep": "x", "skipped": "y"},
+    }
+    data = LLMCallSpanData.from_standard_logging_payload(payload)
+    bag = promoted_baggage(
+        data.identity,
+        data.request_model,
+        BAGGAGE_PROMOTED_KEYS,
+        metadata_keys=(
+            "requester_metadata.trace_id",
+            "requester_metadata.attempt",
+            "requester_metadata.empty",
+            "requester_metadata.nested.deep",
+            "a.b",
+        ),
+    )
+    engine.emit(SpanRole.LLM_CALL, data, ctx_mod.set_request_baggage(bag))
+    (span,) = exporter.get_finished_spans()
+    assert span.attributes[f"{LiteLLM.METADATA_PREFIX}trace_id"] == "abc"
+    assert span.attributes[f"{LiteLLM.METADATA_PREFIX}attempt"] == "0"
+    assert span.attributes[f"{LiteLLM.METADATA_PREFIX}nested.deep"] == "x"
+    assert span.attributes[f"{LiteLLM.METADATA_PREFIX}a.b"] == "flat"
+    assert f"{LiteLLM.METADATA_PREFIX}empty" not in span.attributes
+    assert f"{LiteLLM.METADATA_PREFIX}deep" not in span.attributes
+    assert f"{LiteLLM.METADATA_PREFIX}nested.skipped" not in span.attributes
+    assert not any(k.startswith(f"{LiteLLM.METADATA_PREFIX}requester_metadata") for k in span.attributes)
+
+
 def test_http_attributes_never_promoted():
     """Even if http.* is present in baggage, the processor must not stamp it on
     child spans (it belongs on the SERVER span only)."""

tests/test_litellm/integrations/otel/test_otel_v2_logger.py

@@ -1623,17 +1623,22 @@ def test_provider_model_and_team_metadata_on_real_boundary_flow():
 def test_pre_call_hook_seeds_baggage_onto_server_and_child_spans():
     """The pre-call hook seeds identity Baggage in the request context so the
     server span (stamped directly) AND later child spans (service here, via the
-    Baggage processor) carry identity — not just the LLM-call span."""
+    Baggage processor) carry identity — not just the LLM-call span. Only the
+    caller's ``requester_metadata`` is read from the request dict, so a proxy-owned
+    sibling such as ``requester_ip_address`` is not stamped from here even though
+    the default allowlist names it, and an unlisted caller key is not promoted."""
     logger, exporter = _logger()
     server = logger._emitter.start_span(
         SpanRole.PROXY_REQUEST, LITELLM_PROXY_REQUEST_SPAN_NAME
     )
+    data = {
+        "model": "gpt-4o",
+        "metadata": {"requester_ip_address": "127.0.0.1", "requester_metadata": {"trace_id": "abc"}},
+    }
 
     async def _flow():
         # pre-call seeds baggage + stamps the active server span
-        await logger.async_pre_call_hook(
-            _Auth(), None, {"model": "gpt-4o"}, "completion"
-        )
+        await logger.async_pre_call_hook(_Auth(), None, data, "completion")
         # a later service call (same task) must inherit the identity
         await logger.async_service_success_hook(
             payload=_ServicePayload("redis", "set"), parent_otel_span=server
@@ -1653,6 +1658,46 @@ def test_pre_call_hook_seeds_baggage_onto_server_and_child_spans():
         srv.attributes[LiteLLM.TEAM_ID] == "t1"
     )  # stamped directly on the server span
     assert srv.attributes[f"{LiteLLM.METADATA_PREFIX}user_api_key_user_id"] == "u1"
+    assert not any(
+        k in (f"{LiteLLM.METADATA_PREFIX}requester_ip_address", f"{LiteLLM.METADATA_PREFIX}trace_id")
+        for s in (redis, srv)
+        for k in s.attributes
+    )
+
+
+def test_pre_call_hook_promotes_nested_request_metadata_key():
+    """``baggage_metadata_keys: [requester_metadata.trace_id]`` reads the caller's
+    ``metadata.trace_id`` (snapshotted by the proxy under ``requester_metadata``)
+    and stamps ``litellm.metadata.trace_id`` on the server, LLM-call and service
+    spans of the request; unlisted siblings are not promoted."""
+    cfg = OpenTelemetryV2Config(exporter="in_memory", baggage_metadata_keys=["requester_metadata.trace_id"])
+    exporter = InMemorySpanExporter()
+    logger = OpenTelemetryV2(config=cfg, tracer_provider=providers.build_tracer_provider(cfg, exporter=exporter))
+    server = logger._emitter.start_span(SpanRole.PROXY_REQUEST, LITELLM_PROXY_REQUEST_SPAN_NAME)
+    data = {"model": "gpt-4o", "metadata": {"requester_metadata": {"trace_id": "abc", "nested": {"deep": "x"}}}}
+    kwargs = _kwargs()
+
+    async def _flow():
+        await logger.async_pre_call_hook(_Auth(), None, data, "completion")
+        logger.log_pre_api_call(model="gpt-4o", messages=[], kwargs=kwargs)
+        await logger.async_log_success_event(kwargs, None, None, None)
+        await logger.async_service_success_hook(payload=_ServicePayload("redis", "set"), parent_otel_span=server)
+
+    with trace.use_span(server, end_on_exit=False):
+        asyncio.run(_flow())
+    server.end()
+
+    spans = {s.name: s for s in exporter.get_finished_spans()}
+    key = f"{LiteLLM.METADATA_PREFIX}trace_id"
+    assert spans[LITELLM_PROXY_REQUEST_SPAN_NAME].attributes[key] == "abc"
+    assert spans["chat gpt-4o"].attributes[key] == "abc"
+    assert spans["redis set"].attributes[key] == "abc"
+    assert data == {"model": "gpt-4o", "metadata": {"requester_metadata": {"trace_id": "abc", "nested": {"deep": "x"}}}}
+    assert not any(
+        k.startswith(f"{LiteLLM.METADATA_PREFIX}requester_metadata") or k.endswith("deep")
+        for s in spans.values()
+        for k in s.attributes
+    )
 
 
 # --------------------------------------------------------------------------- #

tests/test_litellm/integrations/test_opentelemetry.py

@@ -5581,6 +5581,38 @@ class TestOpenTelemetryInferenceIdentityAttributes(unittest.TestCase):
         otel.set_attributes(span, kwargs, {"model": "azure/gpt-4o"})
         assert "http.route" not in self._attr(span, exp)
 
+    def test_nested_metadata_key_promoted_under_caller_path(self):
+        """``baggage_metadata_keys: [requester_metadata.trace_id]`` stamps the
+        caller's nested metadata value as ``litellm.metadata.trace_id`` and a deeper
+        path keeps its dotted name; unlisted siblings stay inside the
+        ``metadata.requester_metadata`` blob."""
+        otel = OpenTelemetry(
+            config=OpenTelemetryConfig(
+                baggage_metadata_keys=["requester_metadata.trace_id", "requester_metadata.nested.deep"]
+            )
+        )
+        kwargs = self._kwargs()
+        kwargs["standard_logging_object"]["metadata"]["requester_metadata"] = {
+            "trace_id": "abc",
+            "nested": {"deep": "x", "skipped": "y"},
+        }
+        span, exp = self._span()
+        otel.set_attributes(span, kwargs, {"model": "azure/gpt-4o"})
+        attrs = self._attr(span, exp)
+        assert attrs["litellm.metadata.trace_id"] == "abc"
+        assert attrs["litellm.metadata.nested.deep"] == "x"
+        assert "litellm.metadata.deep" not in attrs
+        assert "litellm.metadata.nested.skipped" not in attrs
+        assert not any(k.startswith("litellm.metadata.requester_metadata") for k in attrs)
+
+    def test_metadata_keys_default_to_none_promoted(self):
+        otel = OpenTelemetry()
+        kwargs = self._kwargs()
+        kwargs["standard_logging_object"]["metadata"]["requester_metadata"] = {"trace_id": "abc"}
+        span, exp = self._span()
+        otel.set_attributes(span, kwargs, {"model": "azure/gpt-4o"})
+        assert not any(k.startswith("litellm.metadata.") for k in self._attr(span, exp))
+
     def test_team_metadata_json_helper(self):
         keys = ["a", "b"]
         assert OpenTelemetry._team_metadata_json(None, keys) is None
@@ -5631,6 +5663,11 @@ class TestOpenTelemetryTeamMetadataKeysConfig(unittest.TestCase):
             cfg = OpenTelemetryConfig(baggage_team_metadata_keys=["from_arg"])
             assert cfg.baggage_team_metadata_keys == ["from_arg"]
 
+    def test_metadata_keys_from_kwargs_and_env(self):
+        with patch.dict("os.environ", {"LITELLM_OTEL_BAGGAGE_METADATA_KEYS": "requester_metadata.trace_id, a.b"}):
+            assert OpenTelemetryConfig().baggage_metadata_keys == ["requester_metadata.trace_id", "a.b"]
+        assert OpenTelemetry(baggage_metadata_keys="x.y").config.baggage_metadata_keys == ["x.y"]
+
 
 class TestOpenTelemetryMetricAttributeFiltering(unittest.TestCase):
     """LIT-3600: include/exclude control over which attributes are stamped on

tests/test_litellm/llms/bedrock/vector_stores/test_bedrock_vector_store_transformation.py

@@ -1,3 +1,4 @@
+from typing import Final
 from unittest.mock import MagicMock
 
 from litellm.llms.bedrock.vector_stores.transformation import BedrockVectorStoreConfig
@@ -82,6 +83,7 @@ def test_transform_search_request_uses_only_retrieval_config_from_extra_body():
         == "HYBRID"
     )
     assert "unrelatedField" not in body
+    assert "userContext" not in body
 
 
 def test_transform_search_request_does_not_mutate_extra_body_and_overrides_number_of_results():
@@ -152,3 +154,44 @@ def test_transform_search_request_overrides_filter_without_mutating_extra_body()
         ]["value"]
         == "a"
     )
+
+
+def _search_body(extra_body: dict[str, object] | None, litellm_params: dict[str, object]) -> dict[str, object]:
+    config: Final = BedrockVectorStoreConfig()
+    mock_log: Final = MagicMock()
+    mock_log.model_call_details = {}
+    _, body = config.transform_search_vector_store_request(
+        vector_store_id="kb123",
+        query="hello",
+        vector_store_search_optional_params={"max_num_results": 3},
+        api_base="https://bedrock-agent-runtime.us-west-2.amazonaws.com/knowledgebases",
+        litellm_logging_obj=mock_log,
+        litellm_params=litellm_params,
+        extra_body=extra_body,
+    )
+    return body
+
+
+def test_transform_search_request_forwards_user_context_from_extra_body():
+    body = _search_body(extra_body={"userContext": {"userId": "alice@example.com"}}, litellm_params={})
+
+    assert body["userContext"] == {"userId": "alice@example.com"}
+    assert body["retrievalConfiguration"] == {"vectorSearchConfiguration": {"numberOfResults": 3}}
+
+
+def test_transform_search_request_forwards_top_level_user_context_from_litellm_params():
+    body = _search_body(
+        extra_body=None,
+        litellm_params={"vector_store_id": "kb123", "user_context": {"userId": "bob@example.com"}},
+    )
+
+    assert body["userContext"] == {"userId": "bob@example.com"}
+
+
+def test_transform_search_request_prefers_extra_body_user_context_over_top_level():
+    body = _search_body(
+        extra_body={"userContext": {"userId": "alice@example.com"}},
+        litellm_params={"userContext": {"userId": "bob@example.com"}},
+    )
+
+    assert body["userContext"] == {"userId": "alice@example.com"}

tests/test_litellm/llms/fireworks_ai/chat/test_fireworks_ai_chat_transformation.py

@@ -1189,6 +1189,28 @@ def test_reasoning_effort_integer_passthrough():
     assert isinstance(result["reasoning_effort"], int)
 
 
+def test_reasoning_effort_dict_from_anthropic_adapter_flattened_to_effort_string():
+    config = FireworksAIConfig()
+    result = config.map_openai_params(
+        {"reasoning_effort": {"effort": "medium", "summary": "detailed"}},
+        {},
+        _REASONING_MODEL,
+        drop_params=False,
+    )
+    assert result["reasoning_effort"] == "medium"
+
+
+def test_reasoning_effort_dict_without_effort_key_dropped():
+    config = FireworksAIConfig()
+    result = config.map_openai_params(
+        {"reasoning_effort": {"summary": "detailed"}},
+        {},
+        _REASONING_MODEL,
+        drop_params=False,
+    )
+    assert "reasoning_effort" not in result
+
+
 def test_reasoning_effort_auto_dropped_to_model_default():
     config = FireworksAIConfig()
     result = config.map_openai_params(

tests/test_litellm/proxy/hooks/test_key_management_event_hooks.py

@@ -416,6 +416,45 @@ class TestRotateVirtualKeyInSecretManager:
             assert call_kwargs["new_secret_name"] == "test-key-alias-new"
             assert call_kwargs["new_secret_value"] == "sk-new-key"
 
+    @pytest.mark.parametrize("key_alias", ["test-key-alias", None])
+    @pytest.mark.asyncio
+    async def test_rotated_hook_without_request_body_syncs_secret_manager(
+        self, monkeypatch: pytest.MonkeyPatch, key_alias: str | None
+    ):
+        import litellm
+        from litellm.proxy._types import GenerateKeyResponse, LiteLLM_VerificationToken
+        from litellm.secret_managers.base_secret_manager import BaseSecretManager
+        from litellm.types.secret_managers.main import KeyManagementSettings, KeyManagementSystem
+
+        mock_secret_manager: Final = MagicMock(spec=BaseSecretManager)
+        mock_secret_manager.async_rotate_secret = AsyncMock(return_value={"status": "success"})
+        monkeypatch.setattr(litellm, "secret_manager_client", mock_secret_manager)
+        monkeypatch.setattr(litellm, "_key_management_system", KeyManagementSystem.AWS_SECRET_MANAGER)
+        monkeypatch.setattr(
+            litellm,
+            "_key_management_settings",
+            KeyManagementSettings(store_virtual_keys=True, prefix_for_stored_virtual_keys="litellm/"),
+        )
+        monkeypatch.setattr(litellm, "store_audit_logs", False)
+
+        existing_key_row: Final = LiteLLM_VerificationToken(token="hashed-old-token", key_alias=key_alias)
+        response: Final = GenerateKeyResponse(token_id="hashed-new-token", key="sk-new-key", key_alias=key_alias)
+
+        await KeyManagementEventHooks.async_key_rotated_hook(
+            data=None,
+            existing_key_row=existing_key_row,
+            response=response,
+            user_api_key_dict=MagicMock(),
+        )
+
+        expected_secret_name: Final = f"litellm/{key_alias or 'virtual-key-hashed-old-token'}"
+        mock_secret_manager.async_rotate_secret.assert_awaited_once_with(
+            current_secret_name=expected_secret_name,
+            new_secret_name=expected_secret_name,
+            new_secret_value="sk-new-key",
+            optional_params=None,
+        )
+
     @pytest.mark.asyncio
     async def test_rotate_virtual_key_when_store_virtual_keys_disabled(self):
         """Test that rotation is skipped when store_virtual_keys is False."""
@@ -474,6 +513,112 @@ class TestRotateVirtualKeyInSecretManager:
         mock_secret_manager.async_rotate_secret.assert_not_called()
 
 
+class TestKeyUpdatedSecretManagerSync:
+
+    @staticmethod
+    def _configure_secret_manager(
+        monkeypatch: pytest.MonkeyPatch, stored_value: str | None, store_virtual_keys: bool = True
+    ) -> MagicMock:
+        import litellm
+        from litellm.secret_managers.base_secret_manager import BaseSecretManager
+        from litellm.types.secret_managers.main import KeyManagementSettings, KeyManagementSystem
+
+        mock_secret_manager: Final = MagicMock(spec=BaseSecretManager)
+        mock_secret_manager.async_read_secret = AsyncMock(return_value=stored_value)
+        mock_secret_manager.async_rotate_secret = AsyncMock(return_value={"status": "success"})
+        monkeypatch.setattr(litellm, "secret_manager_client", mock_secret_manager)
+        monkeypatch.setattr(litellm, "_key_management_system", KeyManagementSystem.AWS_SECRET_MANAGER)
+        monkeypatch.setattr(
+            litellm,
+            "_key_management_settings",
+            KeyManagementSettings(store_virtual_keys=store_virtual_keys, prefix_for_stored_virtual_keys="litellm/"),
+        )
+        monkeypatch.setattr(litellm, "store_audit_logs", False)
+        return mock_secret_manager
+
+    @pytest.mark.parametrize("existing_alias", ["old-alias", None])
+    @pytest.mark.asyncio
+    async def test_updated_hook_renames_secret_when_alias_changes(
+        self, monkeypatch: pytest.MonkeyPatch, existing_alias: str | None
+    ):
+        from litellm.proxy._types import LiteLLM_VerificationToken, UpdateKeyRequest
+
+        mock_secret_manager: Final = self._configure_secret_manager(monkeypatch, stored_value="sk-stored-key")
+        existing_key_row: Final = LiteLLM_VerificationToken(token="hashed-token", key_alias=existing_alias)
+
+        await KeyManagementEventHooks.async_key_updated_hook(
+            data=UpdateKeyRequest(key="hashed-token", key_alias="new-alias"),
+            existing_key_row=existing_key_row,
+            response=MagicMock(),
+            user_api_key_dict=MagicMock(),
+        )
+
+        current_secret_name: Final = f"litellm/{existing_alias or 'virtual-key-hashed-token'}"
+        mock_secret_manager.async_read_secret.assert_awaited_once_with(
+            secret_name=current_secret_name, optional_params=None
+        )
+        mock_secret_manager.async_rotate_secret.assert_awaited_once_with(
+            current_secret_name=current_secret_name,
+            new_secret_name="litellm/new-alias",
+            new_secret_value="sk-stored-key",
+            optional_params=None,
+        )
+
+    @pytest.mark.parametrize("requested_alias", ["same-alias", None])
+    @pytest.mark.asyncio
+    async def test_updated_hook_leaves_secret_alone_when_alias_unchanged(
+        self, monkeypatch: pytest.MonkeyPatch, requested_alias: str | None
+    ):
+        from litellm.proxy._types import LiteLLM_VerificationToken, UpdateKeyRequest
+
+        mock_secret_manager: Final = self._configure_secret_manager(monkeypatch, stored_value="sk-stored-key")
+
+        await KeyManagementEventHooks.async_key_updated_hook(
+            data=UpdateKeyRequest(key="hashed-token", key_alias=requested_alias, max_budget=10.0),
+            existing_key_row=LiteLLM_VerificationToken(token="hashed-token", key_alias="same-alias"),
+            response=MagicMock(),
+            user_api_key_dict=MagicMock(),
+        )
+
+        mock_secret_manager.async_read_secret.assert_not_awaited()
+        mock_secret_manager.async_rotate_secret.assert_not_awaited()
+
+    @pytest.mark.asyncio
+    async def test_updated_hook_skips_rename_when_secret_missing(self, monkeypatch: pytest.MonkeyPatch):
+        from litellm.proxy._types import LiteLLM_VerificationToken, UpdateKeyRequest
+
+        mock_secret_manager: Final = self._configure_secret_manager(monkeypatch, stored_value=None)
+
+        await KeyManagementEventHooks.async_key_updated_hook(
+            data=UpdateKeyRequest(key="hashed-token", key_alias="new-alias"),
+            existing_key_row=LiteLLM_VerificationToken(token="hashed-token", key_alias="old-alias"),
+            response=MagicMock(),
+            user_api_key_dict=MagicMock(),
+        )
+
+        mock_secret_manager.async_rotate_secret.assert_not_awaited()
+
+    @pytest.mark.asyncio
+    async def test_updated_hook_ignores_alias_change_when_store_virtual_keys_disabled(
+        self, monkeypatch: pytest.MonkeyPatch
+    ):
+        from litellm.proxy._types import LiteLLM_VerificationToken, UpdateKeyRequest
+
+        mock_secret_manager: Final = self._configure_secret_manager(
+            monkeypatch, stored_value="sk-stored-key", store_virtual_keys=False
+        )
+
+        await KeyManagementEventHooks.async_key_updated_hook(
+            data=UpdateKeyRequest(key="hashed-token", key_alias="new-alias"),
+            existing_key_row=LiteLLM_VerificationToken(token="hashed-token", key_alias="old-alias"),
+            response=MagicMock(),
+            user_api_key_dict=MagicMock(),
+        )
+
+        mock_secret_manager.async_read_secret.assert_not_awaited()
+        mock_secret_manager.async_rotate_secret.assert_not_awaited()
+
+
 class TestKeyUpdatedAuditLogObjectId:
     """Tests that /key/update audit logs never store the raw virtual key (issue #31620)."""
 

tests/test_litellm/proxy/pass_through_endpoints/test_llm_pass_through_endpoints.py

@@ -28,6 +28,7 @@ from litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints import (
     BaseOpenAIPassThroughHandler,
     RouteChecks,
     _join_url_paths,
+    anthropic_proxy_route,
     azure_proxy_route,
     bedrock_llm_proxy_route,
     bedrock_proxy_route,
@@ -585,6 +586,7 @@ class TestVertexAIPassThroughHandler:
             "litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints.passthrough_endpoint_router",
             pass_through_router,
         )
+        monkeypatch.setattr("litellm.proxy.proxy_server.master_key", "sk-master-1234")
 
         endpoint = f"/v1/projects/{test_project}/locations/{test_location}/publishers/google/models/gemini-1.5-flash:generateContent"
 
@@ -4286,6 +4288,329 @@ class TestVertexCredentiallessPassthroughVirtualKeyLeak:
         assert "sk-master-1234" not in " ".join(f"{name}:{value}" for name, value in forwarded.items())
 
 
+class TestAnthropicPassthroughVirtualKeyLeak:
+    VKEY = "sk-litellm-victim-key"
+    PROXY_KEY = "sk-ant-api03-proxy-configured-key"
+    ENDPOINT = "v1/messages"
+
+    async def _run(
+        self,
+        monkeypatch,
+        headers: list[tuple[bytes, bytes]],
+        authenticated: UserAPIKeyAuth | None = None,
+        master_key: str | None = "sk-master-1234",
+        proxy_api_key: str | None = None,
+    ) -> tuple[HTTPException | None, dict | None]:
+        from litellm.proxy.pass_through_endpoints.pass_through_endpoints import HttpPassThroughEndpointHelpers
+        from litellm.proxy.pass_through_endpoints.passthrough_endpoint_router import (
+            PassthroughEndpointRouter,
+        )
+
+        monkeypatch.setattr("litellm.proxy.proxy_server.master_key", master_key)
+        monkeypatch.delenv("ANTHROPIC_AUTH_TOKEN", raising=False)
+        if proxy_api_key is None:
+            monkeypatch.delenv("ANTHROPIC_API_KEY", raising=False)
+        else:
+            monkeypatch.setenv("ANTHROPIC_API_KEY", proxy_api_key)
+        caller: Final = authenticated if authenticated is not None else UserAPIKeyAuth(api_key=self.VKEY)
+
+        async def receive():
+            return {"type": "http.request", "body": b"{}", "more_body": False}
+
+        request = Request(
+            {
+                "type": "http",
+                "method": "POST",
+                "path": f"/anthropic/{self.ENDPOINT}",
+                "headers": headers,
+                "query_string": b"",
+            },
+            receive=receive,
+        )
+
+        captured: dict = {}
+
+        def fake_create_pass_through_route(**kwargs):
+            captured.update(kwargs)
+            return AsyncMock(return_value={"status": "success"})
+
+        module = "litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints"
+        monkeypatch.setattr(f"{module}.passthrough_endpoint_router", PassthroughEndpointRouter(lambda: None))
+        raised: HTTPException | None = None
+        with (
+            mock.patch(f"{module}.create_pass_through_route", side_effect=fake_create_pass_through_route),
+            mock.patch(f"{module}.user_api_key_auth", new=AsyncMock(return_value=caller)),
+        ):
+            try:
+                await anthropic_proxy_route(
+                    endpoint=self.ENDPOINT,
+                    request=request,
+                    fastapi_response=Response(),
+                    user_api_key_dict=caller,
+                )
+            except HTTPException as exc:
+                raised = exc
+
+        if not captured:
+            return raised, None
+        upstream: Final = HttpPassThroughEndpointHelpers.forward_headers_from_request(
+            request_headers=dict(request.headers),
+            headers=dict(captured["custom_headers"] or {}),
+            forward_headers=captured.get("_forward_headers", False),
+        )
+        return raised, upstream
+
+    @staticmethod
+    def _blob(forwarded: dict) -> str:
+        return " ".join(f"{name}:{value}" for name, value in forwarded.items())
+
+    @pytest.mark.asyncio
+    async def test_authorization_bearer_virtual_key_is_rejected_not_forwarded(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"authorization", f"Bearer {self.VKEY}".encode()), (b"content-type", b"application/json")],
+        )
+        assert forwarded is None, "credential-less request must never reach the upstream forwarder"
+        assert raised is not None and raised.status_code == 401
+        assert "ANTHROPIC_API_KEY" in str(raised.detail) and "use_in_pass_through" in str(raised.detail)
+
+    @pytest.mark.asyncio
+    async def test_x_api_key_virtual_key_is_rejected_not_forwarded(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"x-api-key", self.VKEY.encode()), (b"content-type", b"application/json")],
+        )
+        assert forwarded is None, "a virtual key that authenticated via x-api-key must be stripped, not forwarded"
+        assert raised is not None and raised.status_code == 401
+
+    @pytest.mark.asyncio
+    async def test_x_litellm_api_key_virtual_key_is_rejected_not_forwarded(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"x-litellm-api-key", self.VKEY.encode()), (b"content-type", b"application/json")],
+        )
+        assert forwarded is None, "credential-less request must never reach the upstream forwarder"
+        assert raised is not None and raised.status_code == 401
+
+    @pytest.mark.asyncio
+    async def test_master_key_in_authorization_is_rejected_not_forwarded(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"authorization", b"Bearer sk-master-1234"), (b"content-type", b"application/json")],
+            authenticated=UserAPIKeyAuth(api_key="sk-master-1234", user_role=LitellmUserRoles.PROXY_ADMIN),
+        )
+        assert forwarded is None, "the master key must never reach Anthropic"
+        assert raised is not None and raised.status_code == 401
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        ("header", "value"),
+        [
+            pytest.param(b"x-api-key", b"sk-ant-api03-callers-own-key", id="x-api-key"),
+            pytest.param(b"authorization", b"Bearer sk-ant-api03-callers-own-key", id="authorization"),
+        ],
+    )
+    async def test_without_a_master_key_the_callers_own_anthropic_key_still_forwards(
+        self, monkeypatch, header: bytes, value: bytes
+    ):
+        monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", {})
+        monkeypatch.setattr("litellm.proxy.proxy_server.user_custom_auth", None)
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(header, value), (b"anthropic-version", b"2023-06-01"), (b"content-type", b"application/json")],
+            authenticated=UserAPIKeyAuth(api_key="sk-ant-api03-callers-own-key", user_role=LitellmUserRoles.INTERNAL_USER),
+            master_key=None,
+        )
+        assert raised is None, "with no master key the proxy authenticated nothing, so nothing of the caller's is a LiteLLM secret"
+        assert forwarded is not None
+        assert forwarded.get(header.decode()) == value.decode()
+
+    @pytest.mark.asyncio
+    async def test_without_a_master_key_a_custom_auth_credential_is_still_stripped(self, monkeypatch):
+        monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", {})
+        monkeypatch.setattr("litellm.proxy.proxy_server.user_custom_auth", AsyncMock())
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"authorization", b"Bearer sk-custom-auth-token"), (b"anthropic-version", b"2023-06-01")],
+            authenticated=UserAPIKeyAuth(api_key="sk-custom-auth-token", user_role=LitellmUserRoles.INTERNAL_USER),
+            master_key=None,
+        )
+        assert raised is not None and raised.status_code == 401
+        assert forwarded is None
+
+    @pytest.mark.asyncio
+    async def test_without_a_master_key_an_oauth2_token_is_still_stripped(self, monkeypatch):
+        monkeypatch.setattr("litellm.proxy.proxy_server.general_settings", {"enable_oauth2_auth": True})
+        monkeypatch.setattr("litellm.proxy.proxy_server.user_custom_auth", None)
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"authorization", b"Bearer oauth2-access-token"), (b"anthropic-version", b"2023-06-01")],
+            authenticated=UserAPIKeyAuth(api_key="oauth2-access-token", user_role=LitellmUserRoles.INTERNAL_USER),
+            master_key=None,
+        )
+        assert raised is not None and raised.status_code == 401
+        assert forwarded is None
+
+    @pytest.mark.asyncio
+    async def test_byo_anthropic_oauth_token_still_forwards_without_virtual_key(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [
+                (b"x-litellm-api-key", self.VKEY.encode()),
+                (b"authorization", b"Bearer sk-ant-oat01-caller-oauth-token"),
+                (b"anthropic-version", b"2023-06-01"),
+                (b"content-type", b"application/json"),
+            ],
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("authorization") == "Bearer sk-ant-oat01-caller-oauth-token"
+        assert forwarded.get("anthropic-version") == "2023-06-01"
+        assert "x-litellm-api-key" not in forwarded
+        assert self.VKEY not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_byo_x_api_key_still_forwards_without_virtual_key(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [
+                (b"authorization", f"Bearer {self.VKEY}".encode()),
+                (b"x-api-key", b"sk-ant-api03-caller-own-key"),
+                (b"content-type", b"application/json"),
+            ],
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("x-api-key") == "sk-ant-api03-caller-own-key"
+        assert "authorization" not in forwarded
+        assert self.VKEY not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_custom_auth_caller_keeps_own_authorization_token(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"authorization", b"Bearer sk-ant-oat01-caller-oauth-token"), (b"content-type", b"application/json")],
+            authenticated=UserAPIKeyAuth(api_key=None),
+            master_key=None,
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("authorization") == "Bearer sk-ant-oat01-caller-oauth-token"
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize(
+        "credential_header",
+        sorted(SpecialHeaders.litellm_credential_header_names() - {"authorization", "x-api-key", "x-litellm-api-key"}),
+    )
+    async def test_every_non_anthropic_credential_header_is_dropped_by_name(self, monkeypatch, credential_header):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [
+                (b"x-litellm-api-key", self.VKEY.encode()),
+                (b"x-api-key", b"sk-ant-api03-caller-own-key"),
+                (credential_header.encode(), b"some-distinct-caller-secret-value"),
+                (b"content-type", b"application/json"),
+            ],
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("x-api-key") == "sk-ant-api03-caller-own-key"
+        assert credential_header not in forwarded
+        assert "x-litellm-api-key" not in forwarded
+        assert self.VKEY not in self._blob(forwarded)
+        assert "some-distinct-caller-secret-value" not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_virtual_key_in_operator_configured_header_is_stripped(self, monkeypatch):
+        with mock.patch.dict(  # test-quality-ok: general_settings is the real proxy config surface for litellm_key_header_name; no injection seam exists on this route
+            "litellm.proxy.proxy_server.general_settings",
+            {"litellm_key_header_name": "x-company-key"},
+        ):
+            raised, forwarded = await self._run(
+                monkeypatch,
+                [
+                    (b"x-company-key", f"Bearer {self.VKEY}".encode()),
+                    (b"x-api-key", b"sk-ant-api03-caller-own-key"),
+                    (b"content-type", b"application/json"),
+                ],
+            )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("x-api-key") == "sk-ant-api03-caller-own-key"
+        assert "x-company-key" not in forwarded
+        assert self.VKEY not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_proxy_credential_replaces_virtual_key_sent_as_bearer(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [
+                (b"authorization", f"Bearer {self.VKEY}".encode()),
+                (b"anthropic-version", b"2023-06-01"),
+                (b"content-type", b"application/json"),
+            ],
+            proxy_api_key=self.PROXY_KEY,
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("x-api-key") == self.PROXY_KEY
+        assert "authorization" not in forwarded
+        assert forwarded.get("anthropic-version") == "2023-06-01"
+        assert self.VKEY not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_proxy_credential_replaces_virtual_key_sent_as_x_api_key(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [(b"x-api-key", self.VKEY.encode()), (b"content-type", b"application/json")],
+            proxy_api_key=self.PROXY_KEY,
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("x-api-key") == self.PROXY_KEY
+        assert self.VKEY not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_proxy_credential_wins_over_callers_own_x_api_key(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [
+                (b"x-litellm-api-key", self.VKEY.encode()),
+                (b"x-api-key", b"sk-ant-api03-caller-own-key"),
+                (b"content-type", b"application/json"),
+            ],
+            proxy_api_key=self.PROXY_KEY,
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("x-api-key") == self.PROXY_KEY
+        assert "sk-ant-api03-caller-own-key" not in self._blob(forwarded)
+
+    @pytest.mark.asyncio
+    async def test_x_pass_and_hop_by_hop_handling_is_unchanged(self, monkeypatch):
+        raised, forwarded = await self._run(
+            monkeypatch,
+            [
+                (b"authorization", f"Bearer {self.VKEY}".encode()),
+                (b"x-pass-anthropic-beta", b"interleaved-thinking-2025-05-14"),
+                (b"x-pass-authorization", b"Bearer smuggled"),
+                (b"content-length", b"2"),
+                (b"host", b"proxy.internal"),
+                (b"accept-encoding", b"br"),
+                (b"user-agent", b"curl/8.7.1"),
+            ],
+            proxy_api_key=self.PROXY_KEY,
+        )
+        assert raised is None
+        assert forwarded is not None
+        assert forwarded.get("anthropic-beta") == "interleaved-thinking-2025-05-14"
+        assert forwarded.get("user-agent") == "curl/8.7.1"
+        assert "authorization" not in forwarded
+        assert "content-length" not in forwarded
+        assert "host" not in forwarded
+        assert "accept-encoding" not in forwarded
+
+
 class TestVertexPassthroughDefaultLocationOnShortRoutes:
     PROJECT = "test-project"
     SHORT_ROUTE = "publishers/google/models/gemini-2.5-flash:generateContent"

tests/test_litellm/vector_stores/test_main.py

@@ -7,6 +7,7 @@ executor, and it must never leak into litellm_params/kwargs where logging would
 model_dump() it (the #19550 serialization trap).
 """
 
+import json
 from unittest.mock import MagicMock, patch
 
 import pytest
@@ -15,6 +16,7 @@ import litellm.vector_stores.main as vector_stores_main
 from litellm.llms.base_llm.vector_store.transformation import (
     RouterVectorStoreEmbeddingExecutor,
 )
+from litellm.llms.custom_httpx.http_handler import HTTPHandler
 from litellm.vector_stores.main import search
 
 MOCK_SEARCH_RESPONSE = {
@@ -89,3 +91,26 @@ def test_search_router_not_in_litellm_params():
     litellm_params = mock_handler.call_args.kwargs["litellm_params"]
     assert "router" not in litellm_params.model_dump(exclude_none=True)
     assert getattr(litellm_params, "router", None) is None
+
+
+def test_search_forwards_top_level_user_context_to_bedrock_retrieve():
+    """Regression (LIT-4415): a top-level userContext, the shape the OpenAI SDK's extra_body
+    produces on the proxy path, reaches the Bedrock Retrieve request body."""
+    client = MagicMock(spec=HTTPHandler)
+    client.post.return_value = MagicMock(status_code=200, json=MagicMock(return_value={"retrievalResults": []}))
+
+    search(
+        vector_store_id="kb123",
+        query="q",
+        custom_llm_provider="bedrock",
+        aws_region_name="us-west-2",
+        aws_access_key_id="test-key-id",
+        aws_secret_access_key="test-secret-key",
+        userContext={"userId": "alice@example.com"},
+        client=client,
+        litellm_logging_obj=MagicMock(),
+    )
+
+    posted = json.loads(client.post.call_args.kwargs["data"])
+    assert posted["userContext"] == {"userId": "alice@example.com"}
+    assert posted["retrievalQuery"] == {"text": "q"}