diff --git a/litellm/litellm_core_utils/streaming_handler.py b/litellm/litellm_core_utils/streaming_handler.py
index 651b169a9b2..f6340426c1b 100644
--- a/litellm/litellm_core_utils/streaming_handler.py
+++ b/litellm/litellm_core_utils/streaming_handler.py
@@ -191,7 +191,7 @@ class CustomStreamWrapper:
         custom_llm_provider: str | None = None,
         stream_options=None,
         make_call: Callable | None = None,
-        _response_headers: dict | None = None,
+        _response_headers: dict | httpx.Headers | None = None,
     ):
         self.model = model
         self.make_call = make_call
diff --git a/litellm/llms/bedrock/chat/converse_handler.py b/litellm/llms/bedrock/chat/converse_handler.py
index 3a093e1f939..ca5f1298360 100644
--- a/litellm/llms/bedrock/chat/converse_handler.py
+++ b/litellm/llms/bedrock/chat/converse_handler.py
@@ -35,7 +35,7 @@ def make_sync_call(
     json_mode: bool | None = False,
     fake_stream: bool = False,
     stream_chunk_size: int | None = None,
-):
+) -> tuple[Any, httpx.Headers]:
     if client is None:
         client = _get_httpx_client()  # Create a new client if none provided
 
@@ -76,7 +76,7 @@ def make_sync_call(
         additional_args={"complete_input_dict": data},
     )
 
-    return completion_stream
+    return completion_stream, response.headers
 
 
 class BedrockConverseLLM(BaseAWSLLM):
@@ -134,7 +134,7 @@ class BedrockConverseLLM(BaseAWSLLM):
             },
         )
 
-        completion_stream: Final = await make_call(
+        completion_stream, response_headers = await make_call(
             client=client,
             api_base=api_base,
             headers=dict(prepped.headers),
@@ -151,6 +151,7 @@ class BedrockConverseLLM(BaseAWSLLM):
             model=model,
             custom_llm_provider="bedrock",
             logging_obj=logging_obj,
+            _response_headers=response_headers,
         )
         return streaming_response
 
@@ -232,7 +233,7 @@ class BedrockConverseLLM(BaseAWSLLM):
         except httpx.TimeoutException:
             raise BedrockError(status_code=408, message="Timeout error occurred.")
 
-        return litellm.AmazonConverseConfig()._transform_response(
+        transformed_response: Final = litellm.AmazonConverseConfig()._transform_response(
             model=model,
             response=response,
             model_response=model_response,
@@ -244,6 +245,8 @@ class BedrockConverseLLM(BaseAWSLLM):
             optional_params=optional_params,
             encoding=encoding,
         )
+        transformed_response.set_provider_response_headers(response.headers)
+        return transformed_response
 
     def completion(
         self,
@@ -541,7 +544,7 @@ class BedrockConverseLLM(BaseAWSLLM):
             client = client
 
         if stream is not None and stream is True:
-            completion_stream: Final = make_sync_call(
+            completion_stream, response_headers = make_sync_call(
                 client=(client if client is not None and isinstance(client, HTTPHandler) else None),
                 api_base=proxy_endpoint_url,
                 headers=prepped.headers,
@@ -558,6 +561,7 @@ class BedrockConverseLLM(BaseAWSLLM):
                 model=model,
                 custom_llm_provider="bedrock",
                 logging_obj=logging_obj,
+                _response_headers=response_headers,
             )
 
             return streaming_response
@@ -578,7 +582,7 @@ class BedrockConverseLLM(BaseAWSLLM):
         except httpx.TimeoutException:
             raise BedrockError(status_code=408, message="Timeout error occurred.")
 
-        return litellm.AmazonConverseConfig()._transform_response(
+        sync_transformed_response: Final = litellm.AmazonConverseConfig()._transform_response(
             model=model,
             response=response,
             model_response=model_response,
@@ -590,3 +594,5 @@ class BedrockConverseLLM(BaseAWSLLM):
             optional_params=optional_params,
             encoding=encoding,
         )
+        sync_transformed_response.set_provider_response_headers(response.headers)
+        return sync_transformed_response
diff --git a/litellm/llms/bedrock/chat/invoke_handler.py b/litellm/llms/bedrock/chat/invoke_handler.py
index 2a125e38a82..ce89c6c23e2 100644
--- a/litellm/llms/bedrock/chat/invoke_handler.py
+++ b/litellm/llms/bedrock/chat/invoke_handler.py
@@ -163,7 +163,7 @@ async def make_call(
     json_mode: bool | None = False,
     bedrock_invoke_provider: litellm.BEDROCK_INVOKE_PROVIDERS_LITERAL | None = None,
     stream_chunk_size: int | None = None,
-):
+) -> tuple[Any, httpx.Headers]:
     try:
         if client is None:
             client = get_async_httpx_client(
@@ -225,7 +225,7 @@ async def make_call(
             additional_args={"complete_input_dict": data},
         )
 
-        return completion_stream
+        return completion_stream, response.headers
     except httpx.HTTPStatusError as err:
         error_code: Final = err.response.status_code
         raise BedrockError(status_code=error_code, message=err.response.text)
@@ -248,7 +248,7 @@ def make_sync_call(
     json_mode: bool | None = False,
     bedrock_invoke_provider: litellm.BEDROCK_INVOKE_PROVIDERS_LITERAL | None = None,
     stream_chunk_size: int | None = None,
-):
+) -> tuple[Any, httpx.Headers]:
     try:
         if client is None:
             client = _get_httpx_client(
@@ -309,7 +309,7 @@ def make_sync_call(
             additional_args={"complete_input_dict": data},
         )
 
-        return completion_stream
+        return completion_stream, response.headers
     except httpx.HTTPStatusError as err:
         error_code: Final = err.response.status_code
         raise BedrockError(status_code=error_code, message=err.response.text)
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 76f91aa9115..333326a766b 100644
--- a/litellm/llms/bedrock/chat/invoke_transformations/base_invoke_transformation.py
+++ b/litellm/llms/bedrock/chat/invoke_transformations/base_invoke_transformation.py
@@ -1,7 +1,6 @@
 import copy
 import json
 import time
-from functools import partial
 from typing import TYPE_CHECKING, Any, Final, cast, get_args
 
 import httpx
@@ -446,24 +445,24 @@ class AmazonInvokeConfig(BaseConfig, BaseAWSLLM):
         json_mode: bool | None = None,
         signed_json_body: bytes | None = None,
     ) -> CustomStreamWrapper:
+        completion_stream, response_headers = await make_call(
+            client=client,
+            api_base=api_base,
+            headers=headers,
+            data=json.dumps(data),
+            model=model,
+            messages=messages,
+            logging_obj=logging_obj,
+            fake_stream=True if "ai21" in api_base else False,
+            bedrock_invoke_provider=self.get_bedrock_invoke_provider(model),
+            json_mode=json_mode,
+        )
         streaming_response: Final = CustomStreamWrapper(
-            completion_stream=None,
-            make_call=partial(
-                make_call,
-                client=client,
-                api_base=api_base,
-                headers=headers,
-                data=json.dumps(data),
-                model=model,
-                messages=messages,
-                logging_obj=logging_obj,
-                fake_stream=True if "ai21" in api_base else False,
-                bedrock_invoke_provider=self.get_bedrock_invoke_provider(model),
-                json_mode=json_mode,
-            ),
+            completion_stream=completion_stream,
             model=model,
             custom_llm_provider="bedrock",
             logging_obj=logging_obj,
+            _response_headers=response_headers,
         )
         return streaming_response
 
@@ -481,27 +480,28 @@ class AmazonInvokeConfig(BaseConfig, BaseAWSLLM):
         json_mode: bool | None = None,
         signed_json_body: bytes | None = None,
     ) -> CustomStreamWrapper:
-        if client is None or isinstance(client, AsyncHTTPHandler):
-            client = _get_httpx_client(params={})
+        sync_client: Final = (
+            _get_httpx_client(params={}) if client is None or isinstance(client, AsyncHTTPHandler) else client
+        )
+        completion_stream, response_headers = make_sync_call(
+            client=sync_client,
+            api_base=api_base,
+            headers=headers,
+            data=json.dumps(data),
+            signed_json_body=signed_json_body,
+            model=model,
+            messages=messages,
+            logging_obj=logging_obj,
+            fake_stream=True if "ai21" in api_base else False,
+            bedrock_invoke_provider=self.get_bedrock_invoke_provider(model),
+            json_mode=json_mode,
+        )
         streaming_response: Final = CustomStreamWrapper(
-            completion_stream=None,
-            make_call=partial(
-                make_sync_call,
-                client=client,
-                api_base=api_base,
-                headers=headers,
-                data=json.dumps(data),
-                signed_json_body=signed_json_body,
-                model=model,
-                messages=messages,
-                logging_obj=logging_obj,
-                fake_stream=True if "ai21" in api_base else False,
-                bedrock_invoke_provider=self.get_bedrock_invoke_provider(model),
-                json_mode=json_mode,
-            ),
+            completion_stream=completion_stream,
             model=model,
             custom_llm_provider="bedrock",
             logging_obj=logging_obj,
+            _response_headers=response_headers,
         )
         return streaming_response
 
diff --git a/litellm/llms/custom_httpx/llm_http_handler.py b/litellm/llms/custom_httpx/llm_http_handler.py
index 9a950d7f920..8c98c526da1 100644
--- a/litellm/llms/custom_httpx/llm_http_handler.py
+++ b/litellm/llms/custom_httpx/llm_http_handler.py
@@ -635,6 +635,7 @@ class BaseLLMHTTPHandler:
                 model=model,
                 custom_llm_provider=custom_llm_provider,
                 logging_obj=logging_obj,
+                _response_headers=headers,
             )
 
         if client is None or not isinstance(client, HTTPHandler):
@@ -798,6 +799,7 @@ class BaseLLMHTTPHandler:
             model=model,
             custom_llm_provider=custom_llm_provider,
             logging_obj=logging_obj,
+            _response_headers=_response_headers,
         )
         return streamwrapper
 
diff --git a/litellm/llms/sagemaker/chat/transformation.py b/litellm/llms/sagemaker/chat/transformation.py
index 99543e7add1..37ddd813d6f 100644
--- a/litellm/llms/sagemaker/chat/transformation.py
+++ b/litellm/llms/sagemaker/chat/transformation.py
@@ -54,7 +54,30 @@ class SagemakerChatConfig(OpenAIGPTConfig, BaseAWSLLM):
         api_key: str | None = None,
         api_base: str | None = None,
     ) -> dict:
-        return headers
+        inference_component_name: Final = optional_params.get("model_id")
+        if not isinstance(inference_component_name, str):
+            return headers
+        return {**headers, "X-Amzn-SageMaker-Inference-Component": inference_component_name}
+
+    def transform_request(
+        self,
+        model: str,
+        messages: list[AllMessageValues],  # mutable-ok: matches the base chat transform signature
+        optional_params: dict,  # mutable-ok: matches the base chat transform signature
+        litellm_params: dict,  # mutable-ok: matches the base chat transform signature
+        headers: dict,  # mutable-ok: matches the base chat transform signature
+    ) -> dict:  # mutable-ok: the handler sends this body straight to httpx
+        request: Final = super().transform_request(
+            model=model,
+            messages=messages,
+            optional_params=optional_params,
+            litellm_params=litellm_params,
+            headers=headers,
+        )
+        served_model_name: Final = litellm_params.get("hf_model_name")
+        if not isinstance(served_model_name, str):
+            return request
+        return {**request, "model": served_model_name}
 
     def get_complete_url(
         self,
diff --git a/litellm/model_prices_and_context_window_backup.json b/litellm/model_prices_and_context_window_backup.json
index 79bc0b4b76c..91c10d13e8e 100644
--- a/litellm/model_prices_and_context_window_backup.json
+++ b/litellm/model_prices_and_context_window_backup.json
@@ -49489,6 +49489,16 @@
         "source": "https://docs.devin.ai/windsurf/plugins/cascade/models"
     },
     "cognition/swe-1.7": {
+        "input_cost_per_token": 5e-07,
+        "output_cost_per_token": 2.5e-06,
+        "cache_read_input_token_cost": 2e-07,
+        "litellm_provider": "cognition",
+        "mode": "chat",
+        "supports_function_calling": true,
+        "supports_prompt_caching": true,
+        "source": "https://docs.devin.ai/desktop/models"
+    },
+    "cognition/swe-1.7-lightning": {
         "input_cost_per_token": 2.5e-06,
         "output_cost_per_token": 1.25e-05,
         "cache_read_input_token_cost": 1e-06,
@@ -49496,7 +49506,7 @@
         "mode": "chat",
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "source": "https://docs.devin.ai/windsurf/plugins/cascade/models"
+        "source": "https://docs.devin.ai/desktop/models"
     },
     "pinstripes/ps/glm-4.5-air": {
         "max_tokens": 128000,
diff --git a/litellm/proxy/management_endpoints/team_endpoints.py b/litellm/proxy/management_endpoints/team_endpoints.py
index 82e22bb5bbf..a8e545a8551 100644
--- a/litellm/proxy/management_endpoints/team_endpoints.py
+++ b/litellm/proxy/management_endpoints/team_endpoints.py
@@ -2640,51 +2640,63 @@ async def _process_team_members(
     return updated_users, updated_team_memberships
 
 
+def _resolve_member_identity(member: Member, updated_users: Sequence[LiteLLM_UserTable]) -> Member:
+    """Return ``member`` with whichever of ``user_id`` / ``user_email`` the caller left out filled in.
+
+    The roster entry is a snapshot, so whatever is missing here is missing for good.
+    Resolution runs both ways off the user rows the add just touched: added by email
+    -> stamp the user_id, added by user_id -> stamp the email. A value the caller
+    supplied is never overwritten.
+    """
+    resolved_user_id: Final = member.user_id or next(
+        (
+            user.user_id
+            for user in updated_users
+            if member.user_email is not None and user.user_email == member.user_email
+        ),
+        None,
+    )
+    resolved_user_email: Final = member.user_email or next(
+        (
+            user.user_email
+            for user in updated_users
+            if resolved_user_id is not None and user.user_id == resolved_user_id and user.user_email is not None
+        ),
+        None,
+    )
+    return member.model_copy(
+        update={  # mutable-ok: pydantic update payload
+            "user_id": resolved_user_id,
+            "user_email": resolved_user_email,
+        }
+    )
+
+
+def _member_already_in_team(member: Member, complete_team_data: LiteLLM_TeamTable) -> bool:
+    return any(
+        (member.user_id is not None and existing_member.user_id == member.user_id)
+        or (member.user_email is not None and existing_member.user_email == member.user_email)
+        for existing_member in complete_team_data.members_with_roles
+    )
+
+
 async def _update_team_members_list(
     data: TeamMemberAddRequest,
     complete_team_data: LiteLLM_TeamTable,
     updated_users: list[LiteLLM_UserTable],
 ) -> None:
     """Update the team's members_with_roles list."""
-    if isinstance(data.member, Member):
-        new_member: Final = data.member.model_copy()
+    requested_members: Final[Sequence[Member]] = (
+        (data.member,) if isinstance(data.member, Member) else tuple(data.member)
+    )
+    resolved_members: Final = tuple(_resolve_member_identity(m, updated_users) for m in requested_members)
 
-        # get user id
-        if new_member.user_id is None and new_member.user_email is not None:
-            for user in updated_users:
-                if user.user_email is not None and user.user_email == new_member.user_email:
-                    new_member.user_id = user.user_id
-
-        # Check if member already exists in team before adding
-        member_already_exists = False
-        for existing_member in complete_team_data.members_with_roles:
-            if (new_member.user_id is not None and existing_member.user_id == new_member.user_id) or (
-                new_member.user_email is not None and existing_member.user_email == new_member.user_email
-            ):
-                member_already_exists = True
-                break
-
-        if not member_already_exists:
-            complete_team_data.members_with_roles.append(new_member)
-
-    elif isinstance(data.member, list):
-        for nm in data.member:
-            if nm.user_id is None and nm.user_email is not None:
-                for user in updated_users:
-                    if user.user_email is not None and user.user_email == nm.user_email:
-                        nm.user_id = user.user_id
-
-            # Check if member already exists in team before adding
-            member_already_exists = False
-            for existing_member in complete_team_data.members_with_roles:
-                if (nm.user_id is not None and existing_member.user_id == nm.user_id) or (
-                    nm.user_email is not None and existing_member.user_email == nm.user_email
-                ):
-                    member_already_exists = True
-                    break
-
-            if not member_already_exists:
-                complete_team_data.members_with_roles.append(nm)
+    # extend() consumes the generator as it appends, so a member already added by this
+    # same call is seen by the next _member_already_in_team check - the batch dedupes
+    # against itself exactly as the append-one-at-a-time loop this replaced did.
+    complete_team_data.members_with_roles.extend(  # rebind-ok: this helper's contract is to grow the caller's roster in place
+        m for m in resolved_members if not _member_already_in_team(m, complete_team_data)
+    )
 
 
 async def _add_team_members_to_team(
@@ -4086,6 +4098,39 @@ async def _add_team_member_budget_table(
     return team_info_response_object
 
 
+async def _hydrate_member_emails(
+    prisma_client: PrismaClient,
+    members: Sequence[Member],
+) -> tuple[Member, ...]:
+    """Fill in ``user_email`` for roster entries that were stored without one.
+
+    ``members_with_roles`` is a denormalized snapshot written at add-time, so an entry
+    stored with ``user_email=None`` keeps that null even once the user row has an email.
+    Look the missing ones up in ``LiteLLM_UserTable`` (one indexed query) and fill them
+    in. A stored email is never overwritten - the snapshot stays the source of truth
+    wherever it has a value.
+    """
+    missing_user_ids: Final = frozenset(m.user_id for m in members if not m.user_email and m.user_id is not None)
+    if not missing_user_ids:
+        return tuple(members)
+
+    user_rows: Final[Sequence[LiteLLM_UserTable]] = await _user_db(prisma_client).find_many(
+        where={  # mutable-ok: Prisma query filters are dict-shaped
+            "user_id": {  # mutable-ok: Prisma query filters are dict-shaped
+                "in": sorted(missing_user_ids)
+            }
+        }
+    )
+    email_by_user_id: Final = MappingProxyType({u.user_id: u.user_email for u in user_rows if u.user_email})
+
+    return tuple(
+        m.model_copy(update={"user_email": email_by_user_id[m.user_id]})  # mutable-ok: pydantic update payload
+        if not m.user_email and m.user_id in email_by_user_id
+        else m
+        for m in members
+    )
+
+
 async def _resolve_team_access_group_resources(
     _team_info: TeamInfoResponseObjectTeamTable,
 ) -> TeamInfoResponseObjectTeamTable:
@@ -4221,9 +4266,22 @@ async def team_info(
         # Resolve resources inherited from access groups
         resolved_team_info: Final = await _resolve_team_access_group_resources(_team_info)
 
+        # Fill in emails the add-time roster snapshot never captured
+        hydrated_members: Final = await _hydrate_member_emails(
+            prisma_client=prisma_client,
+            members=resolved_team_info.members_with_roles,
+        )
+        hydrated_team_info: Final = resolved_team_info.model_copy(
+            update={  # mutable-ok: pydantic update payload
+                # list(), not the tuple: model_copy skips validation, so the field has
+                # to be handed the list[Member] the response model declares.
+                "members_with_roles": list(hydrated_members)  # mutable-ok: declared list[Member]
+            }
+        )
+
         response_object: Final = TeamInfoResponseObject(
             team_id=team_id,
-            team_info=resolved_team_info,
+            team_info=hydrated_team_info,
             keys=keys,
             team_memberships=returned_tm,
         )
diff --git a/litellm/proxy/spend_tracking/spend_tracking_utils.py b/litellm/proxy/spend_tracking/spend_tracking_utils.py
index 822f03873b3..a9f1dc990db 100644
--- a/litellm/proxy/spend_tracking/spend_tracking_utils.py
+++ b/litellm/proxy/spend_tracking/spend_tracking_utils.py
@@ -10,6 +10,7 @@ from pydantic import BaseModel
 import litellm
 from litellm._logging import verbose_proxy_logger
 from litellm.constants import (
+    LITELLM_PROXY_MASTER_KEY_ALIAS,
     LITELLM_TRUNCATED_PAYLOAD_FIELD,
     LITELLM_TRUNCATION_DB_SAFEGUARD_NOTE,
     REDACTED_BY_LITELM_STRING,
@@ -21,6 +22,7 @@ from litellm.litellm_core_utils.core_helpers import (
     get_litellm_metadata_from_kwargs,
     reconstruct_model_name,
 )
+from litellm.litellm_core_utils.litellm_logging import is_valid_sha256_hash
 from litellm.litellm_core_utils.safe_json_dumps import safe_dumps, strip_null_bytes
 from litellm.proxy._types import SpendLogsMetadata, SpendLogsPayload
 from litellm.proxy.spend_tracking.spend_log_error_logger import spend_log_error
@@ -53,13 +55,6 @@ def _get_max_string_length_prompt_in_db() -> int:
         return DEFAULT_MAX_STRING_LENGTH_PROMPT_IN_DB
 
 
-def _hash_api_key_for_spend_log(api_key: str) -> str:
-    stripped: Final = api_key[7:] if api_key[:7].lower() == "bearer " else api_key
-    if stripped.startswith("sk-"):
-        return hash_token(stripped)
-    return stripped
-
-
 def _is_master_key(api_key: str | None, _master_key: str | None) -> bool:
     """
     Raw-only constant-time master-key comparison. The hashed form is never
@@ -70,6 +65,28 @@ def _is_master_key(api_key: str | None, _master_key: str | None) -> bool:
     return secrets.compare_digest(api_key, _master_key)
 
 
+_HASHED_JWT_RE = re.compile(r"hashed-jwt-[a-fA-F0-9]{64}")
+
+
+def _is_non_secret_key_value(value: str) -> bool:
+    return (
+        value == LITELLM_PROXY_MASTER_KEY_ALIAS
+        or is_valid_sha256_hash(value)
+        or _HASHED_JWT_RE.fullmatch(value) is not None
+    )
+
+
+def _redact_logged_api_key(value: str | None, *, already_redacted: bool = False) -> str | None:
+    if not isinstance(value, str) or not value:
+        return None
+    stripped: Final = re.sub(r"(?i)^bearer ", "", value)
+    if not stripped:
+        return None
+    if already_redacted and _is_non_secret_key_value(stripped):
+        return stripped
+    return hash_token(stripped)
+
+
 def _get_spend_logs_metadata(
     metadata: dict | None,
     applied_guardrails: list[str] | None = None,
@@ -123,9 +140,12 @@ def _get_spend_logs_metadata(
 
     # Filter the metadata dictionary to include only the specified keys
     clean_metadata: Final = SpendLogsMetadata(**{key: metadata.get(key) for key in SpendLogsMetadata.__annotations__})
-    raw_user_api_key: Final = clean_metadata.get("user_api_key")
-    if raw_user_api_key is not None and isinstance(raw_user_api_key, str):
-        clean_metadata["user_api_key"] = _hash_api_key_for_spend_log(raw_user_api_key)
+    _raw_key: Final = clean_metadata.get("user_api_key")
+    _trusted_hash: Final = metadata.get("user_api_key_hash")
+    _already_redacted: Final = (
+        isinstance(_trusted_hash, str) and _is_non_secret_key_value(_trusted_hash) and _trusted_hash == _raw_key
+    )
+    clean_metadata["user_api_key"] = _redact_logged_api_key(_raw_key, already_redacted=_already_redacted)
     clean_metadata["applied_guardrails"] = applied_guardrails
     clean_metadata["batch_models"] = batch_models
     clean_metadata["mcp_tool_call_metadata"] = mcp_tool_call_metadata
@@ -281,16 +301,23 @@ def get_logging_payload(kwargs, response_obj, start_time, end_time) -> SpendLogs
         standard_logging_prompt_tokens = standard_logging_payload.get("prompt_tokens", 0)
         standard_logging_completion_tokens = standard_logging_payload.get("completion_tokens", 0)
         standard_logging_total_tokens = standard_logging_payload.get("total_tokens", 0)
-    if api_key is not None and isinstance(api_key, str):
-        api_key = _hash_api_key_for_spend_log(api_key)
+    _trusted_hash = metadata.get("user_api_key_hash")
+    _key_already_redacted = (
+        isinstance(_trusted_hash, str) and _is_non_secret_key_value(_trusted_hash) and _trusted_hash == api_key
+    )
+    api_key = _redact_logged_api_key(api_key, already_redacted=_key_already_redacted) or ""
 
     if (
         standard_logging_payload is not None
     ):  # [TODO] migrate completely to sl payload. currently missing pass-through endpoint data
-        api_key = api_key or standard_logging_payload["metadata"].get("user_api_key_hash") or ""
+        api_key = (
+            api_key
+            or _redact_logged_api_key(
+                standard_logging_payload["metadata"].get("user_api_key_hash"), already_redacted=True
+            )
+            or ""
+        )
         end_user_id = end_user_id or standard_logging_payload["metadata"].get("user_api_key_end_user_id")
-    # BUG FIX: Don't overwrite api_key when standard_logging_payload is None
-    # The api_key was already extracted from metadata (line 243) and hashed (lines 256-259)
     request_tags = safe_dumps(metadata.get("tags", [])) if isinstance(metadata.get("tags", []), list) else "[]"
     if (
         standard_logging_payload is not None and standard_logging_payload.get("request_tags") is not None
diff --git a/litellm/types/utils.py b/litellm/types/utils.py
index e6138101899..d3effbdfd34 100644
--- a/litellm/types/utils.py
+++ b/litellm/types/utils.py
@@ -11,6 +11,7 @@ from typing import (
     get_args,
 )
 
+import httpx
 from openai._models import BaseModel as OpenAIObject
 from openai.types.audio.transcription_create_params import (
     FileTypes as FileTypes,
@@ -49,7 +50,7 @@ from litellm.types.llms.base import (
 )
 from litellm.types.mcp import MCPServerCostInfo
 
-from ..litellm_core_utils.core_helpers import map_finish_reason
+from ..litellm_core_utils.core_helpers import map_finish_reason, process_response_headers
 from .agents import LiteLLMSendMessageResponse
 from .guardrails import GuardrailEventHooks
 from .llms.anthropic_messages.anthropic_response import AnthropicMessagesResponse
@@ -1916,6 +1917,10 @@ class ModelResponseBase(OpenAIObject):
 
     _response_headers: dict | None = None
 
+    def set_provider_response_headers(self, headers: httpx.Headers) -> None:
+        """Surface a provider's raw response headers to the caller as `llm_provider-*` headers."""
+        self._hidden_params["additional_headers"] = process_response_headers(headers)
+
     def model_dump(self, **kwargs):
         """Default to exclude_unset to avoid Pydantic serializer warnings for OpenAIObject-derived types."""
         if "exclude_unset" not in kwargs and "exclude_none" not in kwargs:
diff --git a/model_prices_and_context_window.json b/model_prices_and_context_window.json
index 79bc0b4b76c..91c10d13e8e 100644
--- a/model_prices_and_context_window.json
+++ b/model_prices_and_context_window.json
@@ -49489,6 +49489,16 @@
         "source": "https://docs.devin.ai/windsurf/plugins/cascade/models"
     },
     "cognition/swe-1.7": {
+        "input_cost_per_token": 5e-07,
+        "output_cost_per_token": 2.5e-06,
+        "cache_read_input_token_cost": 2e-07,
+        "litellm_provider": "cognition",
+        "mode": "chat",
+        "supports_function_calling": true,
+        "supports_prompt_caching": true,
+        "source": "https://docs.devin.ai/desktop/models"
+    },
+    "cognition/swe-1.7-lightning": {
         "input_cost_per_token": 2.5e-06,
         "output_cost_per_token": 1.25e-05,
         "cache_read_input_token_cost": 1e-06,
@@ -49496,7 +49506,7 @@
         "mode": "chat",
         "supports_function_calling": true,
         "supports_prompt_caching": true,
-        "source": "https://docs.devin.ai/windsurf/plugins/cascade/models"
+        "source": "https://docs.devin.ai/desktop/models"
     },
     "pinstripes/ps/glm-4.5-air": {
         "max_tokens": 128000,
diff --git a/ruff-tests.toml b/ruff-tests.toml
index 6e77f4792a7..60438d355f0 100644
--- a/ruff-tests.toml
+++ b/ruff-tests.toml
@@ -20,6 +20,12 @@
 # PT012   a `pytest.raises` block that runs on past the raising call. Everything after
 #         that call is dead, so an `assert` sitting there is never checked. Keep the
 #         block to the call itself and put the assertions below it
+# PT011   `pytest.raises(Exception)` / `(ValueError)` / `(OSError)` with no `match=`. The
+#         block passes on any error that broad, so the TypeError a refactor introduced
+#         reads as the rejection under test. Pin the message the code actually raises
+# PT014   the same `parametrize` case listed twice. The copy re-runs an assertion that
+#         already passed and adds no coverage, and it usually marks a case someone meant
+#         to vary and forgot to edit
 #
 # No target-version here on purpose: it resolves from requires-python (>=3.10), so
 # 3.11-only builtins like BaseExceptionGroup are correctly flagged in a tree that
@@ -27,4 +33,4 @@
 
 line-length = 120
 
-lint.select = ["F821", "B011", "B015", "B017", "B018", "PT012", "PT015", "PLR0133", "PLW0127"]
+lint.select = ["F821", "B011", "B015", "B017", "B018", "PT011", "PT012", "PT014", "PT015", "PLR0133", "PLW0127"]
diff --git a/tests/enterprise/litellm_enterprise/integrations/test_prometheus.py b/tests/enterprise/litellm_enterprise/integrations/test_prometheus.py
index 0cd6055e09d..bdf73b6ab03 100644
--- a/tests/enterprise/litellm_enterprise/integrations/test_prometheus.py
+++ b/tests/enterprise/litellm_enterprise/integrations/test_prometheus.py
@@ -400,7 +400,7 @@ def test_invalid_metric_name_validation():
     litellm.prometheus_metrics_config = test_config
 
     # Creating PrometheusLogger should raise ValueError due to invalid metric
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Configuration validation failed') as exc_info:
         PrometheusLogger()
 
     # Verify error message contains information about invalid metric
@@ -429,7 +429,7 @@ def test_invalid_labels_validation():
     litellm.prometheus_metrics_config = test_config
 
     # Creating PrometheusLogger should raise ValueError due to invalid labels
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Configuration validation failed') as exc_info:
         PrometheusLogger()
 
     # Verify error message contains information about invalid labels
@@ -598,7 +598,7 @@ def test_invalid_exclude_metric_name_raises(reset_prometheus_exclude_settings):
     litellm.prometheus_exclude_labels = None
     litellm.prometheus_exclude_metrics = ["not_a_real_metric"]
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Prometheus exclude configuration validation failed') as exc_info:
         PrometheusLogger()
 
     assert "not_a_real_metric" in str(exc_info.value)
@@ -612,7 +612,7 @@ def test_invalid_exclude_label_name_raises(reset_prometheus_exclude_settings):
     litellm.prometheus_exclude_metrics = None
     litellm.prometheus_exclude_labels = ["not_a_real_label"]
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Prometheus exclude configuration validation failed') as exc_info:
         PrometheusLogger()
 
     assert "not_a_real_label" in str(exc_info.value)
diff --git a/tests/enterprise/litellm_enterprise/proxy/guardrails/test_bedrock_apply_guardrail.py b/tests/enterprise/litellm_enterprise/proxy/guardrails/test_bedrock_apply_guardrail.py
index f257b47404e..6b6b5d768dd 100644
--- a/tests/enterprise/litellm_enterprise/proxy/guardrails/test_bedrock_apply_guardrail.py
+++ b/tests/enterprise/litellm_enterprise/proxy/guardrails/test_bedrock_apply_guardrail.py
@@ -141,7 +141,7 @@ async def test_bedrock_apply_guardrail_api_failure():
         mock_api_request.side_effect = Exception("API connection failed")
 
         # Test the apply_guardrail method should raise an exception
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Bedrock guardrail failed: API connection failed') as exc_info:
             await guardrail.apply_guardrail(
                 inputs={"texts": ["This is a test message"]},
                 request_data={},
diff --git a/tests/enterprise/litellm_enterprise/proxy/hooks/test_managed_files.py b/tests/enterprise/litellm_enterprise/proxy/hooks/test_managed_files.py
index 714f3be6df9..2d845a445b5 100644
--- a/tests/enterprise/litellm_enterprise/proxy/hooks/test_managed_files.py
+++ b/tests/enterprise/litellm_enterprise/proxy/hooks/test_managed_files.py
@@ -1653,7 +1653,7 @@ async def test_afile_retrieve_raises_error_when_no_router_and_file_object_none()
 
     unified_file_id = "test-unified-file-id"
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='LiteLLM Managed File object with id=test-unified-file-id') as exc_info:
         await proxy_managed_files.afile_retrieve(
             file_id=unified_file_id,
             litellm_parent_otel_span=None,
@@ -1719,7 +1719,7 @@ async def test_afile_retrieve_raises_error_for_non_managed_file():
     # Mock get_unified_file_id to return None (file not found)
     proxy_managed_files.get_unified_file_id = AsyncMock(return_value=None)
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='LiteLLM Managed File object with id=non-existent-file-id') as exc_info:
         await proxy_managed_files.afile_retrieve(
             file_id="non-existent-file-id",
             litellm_parent_otel_span=None,
@@ -2027,7 +2027,7 @@ async def test_list_batches_from_managed_objects_table_provider_filter_raises_ex
     )
 
     # Filtering by provider should raise Exception
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="Filtering by 'provider' is not supported when using managed") as exc_info:
         await proxy_managed_files.list_user_batches(
             user_api_key_dict=UserAPIKeyAuth(user_id="test-user"),
             limit=10,
@@ -2053,7 +2053,7 @@ async def test_list_batches_from_managed_objects_table_target_model_name_filter_
     )
 
     # Filtering by provider should raise Exception
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="Filtering by 'target_model_names' is not supported when") as exc_info:
         await proxy_managed_files.list_user_batches(
             user_api_key_dict=UserAPIKeyAuth(user_id="test-user"),
             limit=10,
diff --git a/tests/enterprise/litellm_enterprise/proxy/management_endpoints/test_project_endpoints_prisma.py b/tests/enterprise/litellm_enterprise/proxy/management_endpoints/test_project_endpoints_prisma.py
index bd6637ffcac..ed6735a7126 100644
--- a/tests/enterprise/litellm_enterprise/proxy/management_endpoints/test_project_endpoints_prisma.py
+++ b/tests/enterprise/litellm_enterprise/proxy/management_endpoints/test_project_endpoints_prisma.py
@@ -448,7 +448,7 @@ def test_check_team_project_limits_models_not_in_team():
         models=["gpt-5.5", "claude-3"],  # claude-3 not in team
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="not in team's allowed models\\. Team allowed models") as exc_info:
         _check_team_project_limits(team_object=team, data=data)
 
     assert "claude-3" in str(exc_info.value.detail)
@@ -476,7 +476,7 @@ def test_check_team_project_limits_budget_exceeds_team():
         max_budget=150.0,  # exceeds team's 100.0
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Project max_budget') as exc_info:
         _check_team_project_limits(team_object=team, data=data)
 
     assert "exceeds team's max_budget" in str(exc_info.value.detail)
@@ -551,7 +551,7 @@ def test_check_team_project_limits_tpm_exceeds_team():
         tpm_limit=20000,  # exceeds team's 10000
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Project tpm_limit') as exc_info:
         _check_team_project_limits(team_object=team, data=data)
 
     assert "exceeds team's tpm_limit" in str(exc_info.value.detail)
@@ -577,7 +577,7 @@ def test_check_team_project_limits_negative_budget():
         max_budget=-10.0,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='max_budget cannot be negative\\. Received') as exc_info:
         _check_team_project_limits(team_object=team, data=data)
 
     assert "cannot be negative" in str(exc_info.value.detail)
@@ -604,7 +604,7 @@ def test_check_team_project_limits_soft_budget_gte_max():
         soft_budget=100.0,  # equal to max, should fail
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='must be strictly lower than max_budget') as exc_info:
         _check_team_project_limits(team_object=team, data=data)
 
     assert "must be strictly lower" in str(exc_info.value.detail)
diff --git a/tests/guardrails_tests/test_dynamoai_guardrails.py b/tests/guardrails_tests/test_dynamoai_guardrails.py
index 98f676a71d5..6f0ea00165b 100644
--- a/tests/guardrails_tests/test_dynamoai_guardrails.py
+++ b/tests/guardrails_tests/test_dynamoai_guardrails.py
@@ -61,7 +61,7 @@ async def test_dynamoai_blocks_content_with_block_action():
         guardrail.should_run_guardrail = MagicMock(return_value=True)
 
         # Test that the guardrail raises ValueError for blocked content
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='violation\\(s\\) detected') as exc_info:
             await guardrail.async_pre_call_hook(
                 data=request_data,
                 user_api_key_dict=UserAPIKeyAuth(),
diff --git a/tests/guardrails_tests/test_eu_ai_act_article5.py b/tests/guardrails_tests/test_eu_ai_act_article5.py
index 0903e6c5416..f7384667481 100644
--- a/tests/guardrails_tests/test_eu_ai_act_article5.py
+++ b/tests/guardrails_tests/test_eu_ai_act_article5.py
@@ -211,7 +211,7 @@ class TestEUAIActArticle5ConditionalMatching:
         # Apply guardrail
         if expected == "BLOCK":
             # Should raise an exception or return modified response indicating block
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='Content blocked: eu_ai_act_article') as exc_info:
                 await content_filter_guardrail.apply_guardrail(
                     inputs={"texts": [sentence]},
                     request_data=request_data,
diff --git a/tests/guardrails_tests/test_eu_ai_act_french_3_scenarios.py b/tests/guardrails_tests/test_eu_ai_act_french_3_scenarios.py
index 6b9774d9cde..221ca5aa6e6 100644
--- a/tests/guardrails_tests/test_eu_ai_act_french_3_scenarios.py
+++ b/tests/guardrails_tests/test_eu_ai_act_french_3_scenarios.py
@@ -83,7 +83,7 @@ class TestEUAIActFrench3Scenarios:
         print(f"{'='*70}\n")
 
         # Should raise an exception (blocked)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="prohibited_practices_fr conditional match 'concevoir \\+") as exc_info:
             await content_filter_guardrail.apply_guardrail(
                 inputs={"texts": [sentence]},
                 request_data=request_data,
@@ -123,7 +123,7 @@ class TestEUAIActFrench3Scenarios:
         print(f"{'='*70}\n")
 
         # Should raise an exception (blocked)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="prohibited_practices_fr conditional match 'créer \\+") as exc_info:
             await content_filter_guardrail.apply_guardrail(
                 inputs={"texts": [sentence]},
                 request_data=request_data,
@@ -194,7 +194,7 @@ class TestEUAIActFrench3Scenarios:
         print(f"{'='*70}\n")
 
         # Should raise an exception (blocked by conditional matching)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="prohibited_practices_fr conditional match 'développer \\+") as exc_info:
             await content_filter_guardrail.apply_guardrail(
                 inputs={"texts": [sentence]},
                 request_data=request_data,
@@ -278,7 +278,7 @@ class TestFrenchEdgeCases:
         request_data = {"messages": [{"role": "user", "content": sentence}]}
 
         # Should still block (no exception bypass)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="prohibited_practices_fr conditional match 'créer \\+ crédit") as exc_info:
             await content_filter_guardrail.apply_guardrail(
                 inputs={"texts": [sentence]},
                 request_data=request_data,
diff --git a/tests/guardrails_tests/test_sg_mas_ai_guardrails.py b/tests/guardrails_tests/test_sg_mas_ai_guardrails.py
index 668ee704692..e587d666a79 100644
--- a/tests/guardrails_tests/test_sg_mas_ai_guardrails.py
+++ b/tests/guardrails_tests/test_sg_mas_ai_guardrails.py
@@ -55,7 +55,7 @@ def _make_guardrail(yaml_filename: str, category_name: str) -> ContentFilterGuar
 
 async def _expect_block(guardrail: ContentFilterGuardrail, sentence: str, reason: str):
     request_data = {"messages": [{"role": "user", "content": sentence}]}
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Content blocked: sg_mas_') as exc_info:
         await guardrail.apply_guardrail(
             inputs={"texts": [sentence]},
             request_data=request_data,
diff --git a/tests/guardrails_tests/test_sg_pdpa_guardrails.py b/tests/guardrails_tests/test_sg_pdpa_guardrails.py
index fd7133bc745..42c3a15f9f6 100644
--- a/tests/guardrails_tests/test_sg_pdpa_guardrails.py
+++ b/tests/guardrails_tests/test_sg_pdpa_guardrails.py
@@ -62,7 +62,7 @@ def _make_guardrail(yaml_filename: str, category_name: str) -> ContentFilterGuar
 async def _expect_block(guardrail: ContentFilterGuardrail, sentence: str, reason: str):
     """Assert that the guardrail BLOCKS the sentence."""
     request_data = {"messages": [{"role": "user", "content": sentence}]}
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Content blocked: sg_pdpa_') as exc_info:
         await guardrail.apply_guardrail(
             inputs={"texts": [sentence]},
             request_data=request_data,
diff --git a/tests/litellm_utils_tests/test_hashicorp.py b/tests/litellm_utils_tests/test_hashicorp.py
index 9aff7ddc10e..fa39a045227 100644
--- a/tests/litellm_utils_tests/test_hashicorp.py
+++ b/tests/litellm_utils_tests/test_hashicorp.py
@@ -432,7 +432,7 @@ def test_hashicorp_get_url_rejects_path_traversal(monkeypatch, malicious_secret_
     monkeypatch.setenv("HCP_VAULT_TOKEN", "test-token-for-get-url-only")
     manager = HashicorpSecretManager()
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Invalid secret_name'):
         manager.get_url(malicious_secret_name)
 
 
diff --git a/tests/litellm_utils_tests/test_utils.py b/tests/litellm_utils_tests/test_utils.py
index 2b539b97c9b..3c73224d7a1 100644
--- a/tests/litellm_utils_tests/test_utils.py
+++ b/tests/litellm_utils_tests/test_utils.py
@@ -2147,7 +2147,7 @@ def test_validate_user_messages_invalid_content_type():
 
     messages = [{"content": [{"type": "invalid_type", "text": "Hello"}]}]
 
-    with pytest.raises(Exception) as e:
+    with pytest.raises(Exception, match='Please ensure all messages are valid OpenAI chat completion') as e:
         validate_chat_completion_user_messages(messages)
 
     assert "Invalid message" in str(e)
diff --git a/tests/litellm_utils_tests/test_validate_tool_choice.py b/tests/litellm_utils_tests/test_validate_tool_choice.py
index 0e6294a7cd4..07f8c9ed8f4 100644
--- a/tests/litellm_utils_tests/test_validate_tool_choice.py
+++ b/tests/litellm_utils_tests/test_validate_tool_choice.py
@@ -37,27 +37,27 @@ def test_validate_tool_choice_cursor_format():
 def test_validate_tool_choice_invalid_dict():
     """Test that invalid dict formats raise exceptions."""
     # Missing both type and function
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Invalid tool choice, tool_choice=\\{\\}\\. Please ensure') as exc_info:
         validate_chat_completion_tool_choice({})
     assert "Invalid tool choice" in str(exc_info.value)
 
     # Invalid type value
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="Invalid tool choice, tool_choice=\\{'type': 'invalid'\\}\\.") as exc_info:
         validate_chat_completion_tool_choice({"type": "invalid"})
     assert "Invalid tool choice" in str(exc_info.value)
 
     # Has type but missing function when type is "function"
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="Invalid tool choice, tool_choice=\\{'type': 'function'\\}\\.") as exc_info:
         validate_chat_completion_tool_choice({"type": "function"})
     assert "Invalid tool choice" in str(exc_info.value)
 
 
 def test_validate_tool_choice_invalid_type():
     """Test that invalid types raise exceptions."""
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="<class 'int'>\\. Expecting str, or dict\\. Please ensure") as exc_info:
         validate_chat_completion_tool_choice(123)
     assert "Got=<class 'int'>" in str(exc_info.value)
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="Invalid tool choice, tool_choice=\\[\\]\\. Got=<class 'list'>\\.") as exc_info:
         validate_chat_completion_tool_choice([])
     assert "Got=<class 'list'>" in str(exc_info.value)
diff --git a/tests/llm_responses_api_testing/test_responses_hooks.py b/tests/llm_responses_api_testing/test_responses_hooks.py
index 2344a62de4d..66dbb29dba5 100644
--- a/tests/llm_responses_api_testing/test_responses_hooks.py
+++ b/tests/llm_responses_api_testing/test_responses_hooks.py
@@ -295,7 +295,7 @@ async def test_responses_streaming_failure_triggers_failure_handlers():
         call_type=CallTypes.responses.value,
     )
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="boom"):
         iterator._process_chunk('{"delta": "chunk"}')
 
     # allow failure callbacks to run
diff --git a/tests/llm_translation/test_bedrock_completion.py b/tests/llm_translation/test_bedrock_completion.py
index 3303fafafb0..9534bc8de3c 100644
--- a/tests/llm_translation/test_bedrock_completion.py
+++ b/tests/llm_translation/test_bedrock_completion.py
@@ -1890,7 +1890,7 @@ def test_bedrock_completion_test_4(modify_params):
         ]
         assert transformed_messages == expected_messages
     else:
-        with pytest.raises(Exception) as e:
+        with pytest.raises(Exception, match=r"litellm\.modify_params") as e:
             litellm.completion(**data)
         assert "litellm.modify_params" in str(e.value)
 
diff --git a/tests/llm_translation/test_bedrock_moonshot.py b/tests/llm_translation/test_bedrock_moonshot.py
index a9f4a86b3b6..a82d1c6f029 100644
--- a/tests/llm_translation/test_bedrock_moonshot.py
+++ b/tests/llm_translation/test_bedrock_moonshot.py
@@ -12,6 +12,7 @@ This test suite verifies:
 """
 
 from base_llm_unit_tests import BaseLLMChatTest
+import httpx
 import pytest
 import sys
 import os
@@ -208,14 +209,6 @@ class TestBedrockMoonshotInvoke(BaseLLMChatTest):
         endpoint with the messages body. Iteration of the stream itself is
         not exercised here — moonshot streaming delegates to the OpenAI
         parser and is covered by the OpenAI test suite.
-
-        Note: bedrock invoke streaming cannot be intercepted by patching
-        the caller-supplied client, because ``CustomStreamWrapper.fetch_sync_stream``
-        at streaming_handler.py invokes the stored ``make_call`` partial with
-        ``client=litellm.module_level_client``, which overrides any client the
-        caller passed. Patch ``make_sync_call`` at its import site in
-        ``base_invoke_transformation`` so we observe the exact kwargs the
-        partial was built with at stream-wrapper construction time.
         """
         from litellm.utils import CustomStreamWrapper
 
@@ -225,7 +218,7 @@ class TestBedrockMoonshotInvoke(BaseLLMChatTest):
             captured.update(kwargs)
             # Return an empty iterator so the stream wrapper's iteration
             # doesn't try to parse real bytes.
-            return iter([])
+            return iter([]), httpx.Headers()
 
         with patch(
             "litellm.llms.bedrock.chat.invoke_transformations."
@@ -246,11 +239,6 @@ class TestBedrockMoonshotInvoke(BaseLLMChatTest):
                 aws_region_name="us-west-2",
             )
             assert isinstance(response, CustomStreamWrapper)
-            # Trigger fetch_sync_stream → make_call(...) → fake_make_sync_call.
-            try:
-                next(iter(response))
-            except StopIteration:
-                pass
 
         assert captured, "make_sync_call was never invoked"
         assert captured["api_base"].endswith("/invoke-with-response-stream")
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 cc493cc5a28..8c7390d3d04 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
@@ -982,7 +982,7 @@ def test_convert_to_model_response_object_with_real_error():
         },
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception) as exc_info:  # noqa: PT011  # message rides on .message, str() is empty
         convert_to_model_response_object(
             model_response_object=ModelResponse(),
             response_object=response_object,
@@ -1243,7 +1243,7 @@ def test_convert_to_model_response_object_with_error_code_only():
         },
     }
 
-    with pytest.raises(Exception) as exc_info:  # noqa: B017  # bare Exception raised, so status_code is the assertion
+    with pytest.raises(Exception) as exc_info:  # noqa: B017, PT011  # bare Exception, empty message, so status_code is the assertion
         convert_to_model_response_object(
             model_response_object=ModelResponse(),
             response_object=response_object,
@@ -1423,7 +1423,7 @@ def test_error_message_includes_function_args():
         "choices": [{"index": 0}],
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='in convert_to_model_response_object') as exc_info:
         convert_to_model_response_object(
             model_response_object=ModelResponse(),
             response_object=response_object,
diff --git a/tests/llm_translation/test_prompt_factory.py b/tests/llm_translation/test_prompt_factory.py
index c3519fcb40f..1b4c8a82cf4 100644
--- a/tests/llm_translation/test_prompt_factory.py
+++ b/tests/llm_translation/test_prompt_factory.py
@@ -1845,7 +1845,7 @@ def test_parse_tool_call_arguments_malformed_json():
         parse_tool_call_arguments,
     )
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="Failed to parse tool call arguments for tool 'load_skill") as exc_info:
         parse_tool_call_arguments(
             '{"skill_name": "pptx',
             tool_name="load_skill",
@@ -1877,7 +1877,7 @@ def test_convert_to_anthropic_tool_invoke_malformed_json():
         }
     ]
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="Failed to parse tool call arguments for tool 'bad_tool") as exc_info:
         convert_to_anthropic_tool_invoke(tool_calls)
 
     error_msg = str(exc_info.value)
@@ -2023,7 +2023,7 @@ def test_parse_tool_call_arguments_still_raises_for_unrepairable():
         parse_tool_call_arguments,
     )
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="Failed to parse tool call arguments for tool 'test_tool") as exc_info:
         parse_tool_call_arguments(
             '{"key": "unterminated',
             tool_name="test_tool",
diff --git a/tests/llm_translation/test_triton.py b/tests/llm_translation/test_triton.py
index 21887e8d848..f4a26360a6c 100644
--- a/tests/llm_translation/test_triton.py
+++ b/tests/llm_translation/test_triton.py
@@ -45,7 +45,7 @@ def test_split_embedding_by_shape_fails_with_shape_value_error():
             "data": [1, 2, 3, 4, 5, 6],
         }
     ]
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Shape must be of length'):
         TritonEmbeddingConfig.split_embedding_by_shape(
             data[0]["data"], data[0]["shape"]
         )
diff --git a/tests/llm_translation/test_unit_test_bedrock_invoke.py b/tests/llm_translation/test_unit_test_bedrock_invoke.py
index 14f08c759c5..39f02263f03 100644
--- a/tests/llm_translation/test_unit_test_bedrock_invoke.py
+++ b/tests/llm_translation/test_unit_test_bedrock_invoke.py
@@ -59,7 +59,7 @@ def test_transform_request_invalid_provider(bedrock_transformer):
     """Test request transformation with invalid provider"""
     messages = [{"role": "user", "content": "Hello"}]
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Bedrock Invoke HTTPX: Unknown provider=None') as exc_info:
         bedrock_transformer.transform_request(
             model="invalid.model",
             messages=messages,
diff --git a/tests/local_testing/test_auth_utils.py b/tests/local_testing/test_auth_utils.py
index 9aecb7e10e4..88e8c02a606 100644
--- a/tests/local_testing/test_auth_utils.py
+++ b/tests/local_testing/test_auth_utils.py
@@ -264,10 +264,6 @@ def test_get_end_user_id_from_request_body_backwards_compatibility():
             ["gpt-3.5-turbo", "gpt-4o-mini-general-deployment"],
         ),
         ({"model": "gpt-3.5-turbo"}, "gpt-3.5-turbo"),
-        (
-            {"model": "gpt-3.5-turbo, gpt-4o-mini-general-deployment"},
-            ["gpt-3.5-turbo", "gpt-4o-mini-general-deployment"],
-        ),
     ],
 )
 def test_get_model_from_request(request_data, expected_model):
diff --git a/tests/local_testing/test_exceptions.py b/tests/local_testing/test_exceptions.py
index edf847f4cef..8dd90cbfb37 100644
--- a/tests/local_testing/test_exceptions.py
+++ b/tests/local_testing/test_exceptions.py
@@ -1433,7 +1433,7 @@ async def test_exception_bubbling_up(sync_mode, stream_mode, model):
                 sync_stream=sync_mode,
             )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='litellm\\.BadRequestError: OpenAIException - Invalid value') as exc_info:
         await _call_with_bad_role()
 
     assert exc_info.value.code == "invalid_value"
diff --git a/tests/local_testing/test_file_types.py b/tests/local_testing/test_file_types.py
index db83ba0e74b..7fda81ebd45 100644
--- a/tests/local_testing/test_file_types.py
+++ b/tests/local_testing/test_file_types.py
@@ -23,13 +23,13 @@ class TestFileConsts:
     def test_get_file_extension_from_mime_type(self):
         assert get_file_extension_from_mime_type("audio/aac") == "aac"
         assert get_file_extension_from_mime_type("application/pdf") == "pdf"
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='Unknown extension for mime type: application'):
             get_file_extension_from_mime_type("application/unknown")
 
     def test_get_file_type_from_extension(self):
         assert get_file_type_from_extension("aac") == FileType.AAC
         assert get_file_type_from_extension("pdf") == FileType.PDF
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='Unknown file type for extension: unknown'):
             get_file_type_from_extension("unknown")
 
     def test_get_file_extension_for_file_type(self):
diff --git a/tests/local_testing/test_get_model_info.py b/tests/local_testing/test_get_model_info.py
index 385be25fb07..cef05050ac9 100644
--- a/tests/local_testing/test_get_model_info.py
+++ b/tests/local_testing/test_get_model_info.py
@@ -134,7 +134,6 @@ def test_get_model_info_bedrock_region():
         "ft:gpt-3.5-turbo:my-org:custom_suffix:id",
         "ft:gpt-4-0613:my-org:custom_suffix:id",
         "ft:davinci-002:my-org:custom_suffix:id",
-        "ft:gpt-4-0613:my-org:custom_suffix:id",
         "ft:babbage-002:my-org:custom_suffix:id",
         "gpt-35-turbo",
         "ada",
diff --git a/tests/local_testing/test_router_budget_limiter.py b/tests/local_testing/test_router_budget_limiter.py
index 48915137138..4ef99ec8c12 100644
--- a/tests/local_testing/test_router_budget_limiter.py
+++ b/tests/local_testing/test_router_budget_limiter.py
@@ -160,7 +160,7 @@ async def test_provider_budgets_e2e_test_expect_to_fail():
     await asyncio.sleep(2.5)
 
     for _ in range(3):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="Exceeded budget for provider") as exc_info:
             await router.acompletion(
                 messages=[{"role": "user", "content": "Hello, how are you?"}],
                 model="anthropic/claude-sonnet-4-5-20250929",
@@ -594,7 +594,7 @@ async def test_deployment_budgets_e2e_test_expect_to_fail():
     await asyncio.sleep(2.5)
 
     for _ in range(3):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="Exceeded budget for deployment") as exc_info:
             await router.acompletion(
                 messages=[{"role": "user", "content": "Hello, how are you?"}],
                 model="openai/gpt-4o-mini",
@@ -646,7 +646,7 @@ async def test_tag_budgets_e2e_test_expect_to_fail():
     await asyncio.sleep(2.5)
 
     for _ in range(3):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match=f"Exceeded budget for tag='{TAG_NAME}'") as exc_info:
             await router.acompletion(
                 messages=[{"role": "user", "content": "Hello, how are you?"}],
                 model="openai/gpt-4o-mini",
diff --git a/tests/local_testing/test_router_fallbacks.py b/tests/local_testing/test_router_fallbacks.py
index 15c6c5fec59..86dec406332 100644
--- a/tests/local_testing/test_router_fallbacks.py
+++ b/tests/local_testing/test_router_fallbacks.py
@@ -1430,7 +1430,7 @@ async def test_router_fallbacks_default_and_model_specific_fallbacks(sync_mode):
                 messages=[{"role": "user", "content": "Hey, how's it going?"}],
             )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='litellm\\.AuthenticationError: AuthenticationError') as exc_info:
         await _call_bad_model()
     assert isinstance(
         exc_info.value, litellm.AuthenticationError
diff --git a/tests/logging_callback_tests/test_standard_logging_payload.py b/tests/logging_callback_tests/test_standard_logging_payload.py
index d13cdf1337a..6a632c32fc2 100644
--- a/tests/logging_callback_tests/test_standard_logging_payload.py
+++ b/tests/logging_callback_tests/test_standard_logging_payload.py
@@ -293,7 +293,7 @@ def test_cleanup_timestamps():
     assert all(isinstance(x, float) for x in result)
 
     # Test invalid input
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="start_time is required, got=invalid of type <class 'str'>"):
         StandardLoggingPayloadSetup.cleanup_timestamps(
             "invalid", end_float, completion_float
         )
diff --git a/tests/multi_instance_e2e_tests/test_update_team_e2e.py b/tests/multi_instance_e2e_tests/test_update_team_e2e.py
index dfbfbd310ee..13091fd3df6 100644
--- a/tests/multi_instance_e2e_tests/test_update_team_e2e.py
+++ b/tests/multi_instance_e2e_tests/test_update_team_e2e.py
@@ -143,7 +143,7 @@ async def test_team_blocking_behavior_multi_instance():
         assert team_info_4001["blocked"] is True, "Team should be blocked after update"
 
         # 8. Make a chat completion request on port 4000 with a new prompt; expect it to be blocked.
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match="(?i)blocked") as excinfo:
             await chat_completion_on_port(
                 session,
                 key=key,
@@ -157,7 +157,7 @@ async def test_team_blocking_behavior_multi_instance():
         ), f"Expected error indicating team blocked, got: {error_msg}"
 
         # 9. Make a chat completion request on port 4000 with a new prompt; expect it to be blocked.
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match="(?i)blocked") as excinfo:
             await chat_completion_on_port(
                 session,
                 key=key,
@@ -171,7 +171,7 @@ async def test_team_blocking_behavior_multi_instance():
         ), f"Expected error indicating team blocked, got: {error_msg}"
 
         # 9. Repeat the chat completion request with another new prompt; expect it to be blocked.
-        with pytest.raises(Exception) as excinfo_second:
+        with pytest.raises(Exception, match="(?i)blocked") as excinfo_second:
             await chat_completion_on_port(
                 session,
                 key=key,
diff --git a/tests/ocr_tests/test_ocr_azure_document_intelligence.py b/tests/ocr_tests/test_ocr_azure_document_intelligence.py
index 5736bd797e3..e6a2e5e5735 100644
--- a/tests/ocr_tests/test_ocr_azure_document_intelligence.py
+++ b/tests/ocr_tests/test_ocr_azure_document_intelligence.py
@@ -101,7 +101,7 @@ class TestAzureDocumentIntelligencePagesParam:
             cfg.map_ocr_params({"pages": [True, False]}, {}, "prebuilt-layout")
 
     def test_map_ocr_params_unsupported_type_raises(self, cfg):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='based, Mistral-style\\) or a string like'):
             cfg.map_ocr_params({"pages": 5}, {}, "prebuilt-layout")
 
     def test_get_complete_url_appends_pages_query(self, cfg):
diff --git a/tests/otel_tests/test_e2e_model_access.py b/tests/otel_tests/test_e2e_model_access.py
index 5b5f2a89c8d..e5e93c0b179 100644
--- a/tests/otel_tests/test_e2e_model_access.py
+++ b/tests/otel_tests/test_e2e_model_access.py
@@ -3,6 +3,7 @@ import asyncio
 import aiohttp
 import json
 from httpx import AsyncClient
+from openai import PermissionDeniedError
 from typing import Any, Optional, List, Literal
 
 
@@ -134,7 +135,7 @@ async def test_model_access_update():
         await mock_chat_completion(session=session, key=key, model="openai/gpt-5.5")
 
         # Should fail with gpt-5-mini
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(PermissionDeniedError) as exc_info:
             await mock_chat_completion(
                 session=session, key=key, model="openai/gpt-5-mini"
             )
@@ -157,7 +158,7 @@ async def test_model_access_update():
         )
 
         # Non-OpenAI model should still fail
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(PermissionDeniedError) as exc_info:
             await mock_chat_completion(
                 session=session, key=key, model="anthropic/claude-2"
             )
@@ -254,7 +255,7 @@ async def test_team_model_access_update():
         await mock_chat_completion(session=session, key=key, model="openai/gpt-5.5")
 
         # Should fail with gpt-5-mini
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(PermissionDeniedError) as exc_info:
             await mock_chat_completion(
                 session=session, key=key, model="openai/gpt-5-mini"
             )
@@ -279,7 +280,7 @@ async def test_team_model_access_update():
         )
 
         # Non-OpenAI model should still fail
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(PermissionDeniedError) as exc_info:
             await mock_chat_completion(
                 session=session, key=key, model="anthropic/claude-2"
             )
diff --git a/tests/proxy_admin_ui_tests/test_key_management.py b/tests/proxy_admin_ui_tests/test_key_management.py
index 4c5a045509a..7e8494b77fc 100644
--- a/tests/proxy_admin_ui_tests/test_key_management.py
+++ b/tests/proxy_admin_ui_tests/test_key_management.py
@@ -1340,6 +1340,6 @@ async def test_team_model_alias(prisma_client, requested_model, should_pass):
         }, "Expected model aliases to be present"
     else:
         # Verify the key fails with non-aliased models
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(ProxyException) as exc_info:
             await user_api_key_auth(request=request, api_key=f"Bearer {generated_key}")
         assert exc_info.value.type == ProxyErrorTypes.key_model_access_denied
diff --git a/tests/proxy_admin_ui_tests/test_role_based_access.py b/tests/proxy_admin_ui_tests/test_role_based_access.py
index 9398428bd67..f9506fb694b 100644
--- a/tests/proxy_admin_ui_tests/test_role_based_access.py
+++ b/tests/proxy_admin_ui_tests/test_role_based_access.py
@@ -9,7 +9,7 @@ from litellm._uuid import uuid
 from datetime import datetime
 
 from dotenv import load_dotenv
-from fastapi import Request
+from fastapi import HTTPException, Request
 from fastapi.routing import APIRoute
 
 load_dotenv()
@@ -530,7 +530,7 @@ async def test_user_role_permissions(prisma_client, route, user_role, expected_r
             print(f"Auth passed as expected for {route} with role {user_role}")
         else:
             # Should raise an error
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises((ProxyException, HTTPException)) as exc_info:
                 await user_api_key_auth(request=request, api_key=bearer_token)
             print(f"Auth failed as expected for {route} with role {user_role}")
             print(f"Error message: {str(exc_info.value)}")
diff --git a/tests/proxy_unit_tests/test_auth_checks.py b/tests/proxy_unit_tests/test_auth_checks.py
index ffcbe472be7..ef3cbd0ae95 100644
--- a/tests/proxy_unit_tests/test_auth_checks.py
+++ b/tests/proxy_unit_tests/test_auth_checks.py
@@ -173,7 +173,7 @@ async def test_can_key_call_model(model, expect_to_work):
     if expect_to_work:
         await can_key_call_model(**args)
     else:
-        with pytest.raises(Exception) as e:
+        with pytest.raises(Exception, match='key not allowed to access model\\. This key can only access') as e:
             await can_key_call_model(**args)
 
         print(e)
@@ -958,7 +958,7 @@ async def test_can_key_call_model_with_aliases(model, alias_map, expect_to_work)
             llm_router=router,
         )
     else:
-        with pytest.raises(Exception) as e:
+        with pytest.raises(Exception, match='key not allowed to access model\\. This key can only access') as e:
             await can_key_call_model(
                 model=model,
                 llm_model_list=llm_model_list,
diff --git a/tests/proxy_unit_tests/test_jwt.py b/tests/proxy_unit_tests/test_jwt.py
index 4db47a1cde4..686d7021257 100644
--- a/tests/proxy_unit_tests/test_jwt.py
+++ b/tests/proxy_unit_tests/test_jwt.py
@@ -1583,7 +1583,7 @@ async def test_auth_jwt_mismatched_key_fails(monkeypatch):
 
     h = JWTHandler()
     with patch.object(h, "get_public_key", new=AsyncMock(return_value=rsa_jwk)):
-        with pytest.raises(Exception) as exc:
+        with pytest.raises(Exception, match='Validation fails: Expecting a PEM-formatted key\\.') as exc:
             await h.auth_jwt(token)
         assert "Validation fails" in str(exc.value)
 
@@ -1826,7 +1826,7 @@ async def test_multi_issuer_jwt_unknown_issuer_without_global_jwks_rejected(
         kid="issuer-key",
     )
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='Missing JWT Public Key URL from environment\\.') as exc:
         await jwt_handler.auth_jwt(token=token)
 
     assert "Missing JWT Public Key URL" in str(exc.value)
@@ -1857,7 +1857,7 @@ async def test_multi_issuer_jwt_rejects_wrong_audience(monkeypatch):
         kid="issuer-key",
     )
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match="Validation fails: Audience doesn't match") as exc:
         await jwt_handler.auth_jwt(token=token)
 
     assert "Validation fails" in str(exc.value)
@@ -1900,7 +1900,7 @@ async def test_multi_issuer_jwt_same_kid_does_not_cross_issuer_keys(monkeypatch)
         kid=shared_kid,
     )
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='Validation fails: Signature verification failed') as exc:
         await jwt_handler.auth_jwt(token=token)
 
     assert "Validation fails" in str(exc.value)
@@ -1953,7 +1953,7 @@ def test_multi_issuer_jwt_requires_audience_unless_explicitly_disabled(
     issuer = "https://issuer.example.com"
     jwks_url = f"{issuer}/keys"
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='must configure audience or set') as exc:
         LiteLLM_JWTAuth(
             issuers=[
                 {
diff --git a/tests/proxy_unit_tests/test_proxy_utils.py b/tests/proxy_unit_tests/test_proxy_utils.py
index 00ed6d13f63..de2a9282300 100644
--- a/tests/proxy_unit_tests/test_proxy_utils.py
+++ b/tests/proxy_unit_tests/test_proxy_utils.py
@@ -1026,7 +1026,7 @@ def test_enforced_params_check(
     from litellm.proxy.litellm_pre_call_utils import _enforced_params_check
 
     if expected_error:
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='in request body\\. This is a required param'):
             _enforced_params_check(
                 request_body=request_body,
                 general_settings=general_settings,
@@ -2626,7 +2626,7 @@ async def test_during_call_hook_parallel_execution_with_error():
     try:
         litellm.callbacks = [FailingGuardrail()]
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Guardrail violation detected!') as exc_info:
             await proxy_logging.during_call_hook(
                 data={
                     "model": "gpt-4",
diff --git a/tests/proxy_unit_tests/test_update_spend.py b/tests/proxy_unit_tests/test_update_spend.py
index 0d1d6dcf3c6..6b8973fbad2 100644
--- a/tests/proxy_unit_tests/test_update_spend.py
+++ b/tests/proxy_unit_tests/test_update_spend.py
@@ -166,7 +166,7 @@ async def test_update_spend_logs_non_connection_error():
     prisma_client.db.litellm_spendlogs.create_many = create_many_mock
 
     # Execute and verify it raises immediately without retrying
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Unexpected database error') as exc_info:
         await update_spend(prisma_client, None, proxy_logging_obj)
 
     # Verify error message
diff --git a/tests/router_unit_tests/test_router_helper_utils.py b/tests/router_unit_tests/test_router_helper_utils.py
index 1fef0f01df8..f81578dbd99 100644
--- a/tests/router_unit_tests/test_router_helper_utils.py
+++ b/tests/router_unit_tests/test_router_helper_utils.py
@@ -90,7 +90,7 @@ def test_routing_strategy_init_invalid_strategy(model_list):
     router = Router(model_list=model_list)
 
     # Test common mistake: "simple" instead of "simple-shuffle"
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="usage-based-routing', 'provider-budget-routing'\\]\\. Check") as exc_info:
         router.routing_strategy_init(
             routing_strategy="simple", routing_strategy_args={}
         )
@@ -106,7 +106,7 @@ def test_routing_strategy_init_invalid_strategy(model_list):
     assert "Router SDK" in error_msg
 
     # Test completely invalid strategy
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="usage-based-routing', 'provider-budget-routing'\\]\\. Check") as exc_info:
         router.routing_strategy_init(
             routing_strategy="not-a-real-strategy", routing_strategy_args={}
         )
diff --git a/tests/store_model_in_db_tests/test_mcp_servers.py b/tests/store_model_in_db_tests/test_mcp_servers.py
index e9c26221580..735d5d71ad3 100644
--- a/tests/store_model_in_db_tests/test_mcp_servers.py
+++ b/tests/store_model_in_db_tests/test_mcp_servers.py
@@ -471,7 +471,7 @@ def test_validate_mcp_server_name_direct():
     validate_mcp_server_name("valid name")
 
     # Test that invalid names with hyphens raise exceptions
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="Server name cannot contain '-'\\. Use an alternative") as exc_info:
         validate_mcp_server_name("invalid-name")
     assert "cannot contain" in str(exc_info.value)
 
diff --git a/tests/test_litellm/enterprise/enterprise_callbacks/send_emails/test_sendgrid_email.py b/tests/test_litellm/enterprise/enterprise_callbacks/send_emails/test_sendgrid_email.py
index 40439a78a49..5fe4b217e4f 100644
--- a/tests/test_litellm/enterprise/enterprise_callbacks/send_emails/test_sendgrid_email.py
+++ b/tests/test_litellm/enterprise/enterprise_callbacks/send_emails/test_sendgrid_email.py
@@ -104,7 +104,7 @@ async def test_send_email_missing_api_key():
     try:
         logger = SendGridEmailLogger()
 
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='SENDGRID_API_KEY is not set'):
             await logger.send_email(
                 from_email="test@example.com",
                 to_email=["recipient@example.com"],
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 6cc31f991a3..fcd03e77aa2 100644
--- a/tests/test_litellm/enterprise/proxy/test_managed_files_hook.py
+++ b/tests/test_litellm/enterprise/proxy/test_managed_files_hook.py
@@ -471,7 +471,7 @@ async def test_afile_content_error_reports_unified_id_not_provider_uri():
     mock_router.get_deployment_credentials_with_provider = MagicMock(return_value=None)
     mock_router.afile_content = AsyncMock(side_effect=Exception("deployment failed"))
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='LiteLLM Managed File object with') as exc_info:
         await managed_files.afile_content(
             file_id=unified_file_id,
             litellm_parent_otel_span=None,
diff --git a/tests/test_litellm/integrations/cloudzero/test_cloudzero_database.py b/tests/test_litellm/integrations/cloudzero/test_cloudzero_database.py
index 89a5028011c..7f930f90247 100644
--- a/tests/test_litellm/integrations/cloudzero/test_cloudzero_database.py
+++ b/tests/test_litellm/integrations/cloudzero/test_cloudzero_database.py
@@ -51,7 +51,7 @@ async def test_get_usage_data_rejects_invalid_limit(monkeypatch: pytest.MonkeyPa
     """limit must coerce to int or raise ValueError before hitting the DB."""
     db, query_mock = _setup_db(monkeypatch, [])
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='limit must be an integer'):
         await db.get_usage_data(limit="invalid")
 
     assert query_mock.await_count == 0
diff --git a/tests/test_litellm/integrations/cloudzero/test_cz_stream_api.py b/tests/test_litellm/integrations/cloudzero/test_cz_stream_api.py
index 440ce39e021..a715116e5ee 100644
--- a/tests/test_litellm/integrations/cloudzero/test_cz_stream_api.py
+++ b/tests/test_litellm/integrations/cloudzero/test_cz_stream_api.py
@@ -108,7 +108,7 @@ class TestCloudZeroStreamer:
         """Test _parse_and_convert_timestamp method with invalid timestamp."""
         streamer = CloudZeroStreamer("test-key", "test-connection")
 
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="Could not parse timestamp 'invalid-timestamp': Invalid"):
             streamer._parse_and_convert_timestamp("invalid-timestamp")
 
     def test_prepare_batch_payload(self):
diff --git a/tests/test_litellm/integrations/focus/test_focus_database.py b/tests/test_litellm/integrations/focus/test_focus_database.py
index d77af2dd170..5c13665f1f1 100644
--- a/tests/test_litellm/integrations/focus/test_focus_database.py
+++ b/tests/test_litellm/integrations/focus/test_focus_database.py
@@ -68,7 +68,7 @@ async def test_should_accept_string_timestamps(monkeypatch: pytest.MonkeyPatch):
 async def test_should_reject_invalid_limit(monkeypatch: pytest.MonkeyPatch):
     db, query_mock = _setup_db(monkeypatch, [])
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='limit must be an integer'):
         await db.get_usage_data(limit="invalid")
 
     assert query_mock.await_count == 0
diff --git a/tests/test_litellm/integrations/focus/test_s3_destination.py b/tests/test_litellm/integrations/focus/test_s3_destination.py
index f915b2c56a3..8e54b561f82 100644
--- a/tests/test_litellm/integrations/focus/test_s3_destination.py
+++ b/tests/test_litellm/integrations/focus/test_s3_destination.py
@@ -20,7 +20,7 @@ def _window(freq: str = "hourly", hour: int = 5) -> FocusTimeWindow:
 
 
 def test_should_require_bucket_name():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='bucket_name must be provided for S'):
         FocusS3Destination(prefix="focus", config={})
 
 
diff --git a/tests/test_litellm/integrations/gitlab/test_gitlab_client.py b/tests/test_litellm/integrations/gitlab/test_gitlab_client.py
index 4556950cd3e..529868ca06a 100644
--- a/tests/test_litellm/integrations/gitlab/test_gitlab_client.py
+++ b/tests/test_litellm/integrations/gitlab/test_gitlab_client.py
@@ -95,9 +95,9 @@ def enc_project(p):  # how client encodes project in urls
 # Constructor / config tests
 # -----------------------------
 def test_init_requires_project_and_token():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='project and access_token are required'):
         GitLabClient({"project": "p"})
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='project and access_token are required'):
         GitLabClient({"access_token": "t"})
 
 
@@ -127,7 +127,7 @@ def test_set_ref_updates_effective_ref():
     c = make_client(branch="main")
     c.set_ref("feature/x")
     assert c.ref == "feature/x"
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='ref must be a non-empty string'):
         c.set_ref("")
 
 
@@ -193,12 +193,12 @@ def test_get_file_content_permission_errors_are_mapped():
     raw_url = f"https://gitlab.example.com/api/v4/projects/{enc_project('group/sub/repo')}/repository/files/secure%2Ffile.prompt/raw?ref=main"
     # raise_for_status will be called, so return 403 response (not an exception from transport)
     c.http_handler.routes[raw_url] = FakeResponse(status_code=403)
-    with pytest.raises(Exception) as ei:
+    with pytest.raises(Exception, match="Check your GitLab permissions for project 'group") as ei:
         c.get_file_content("secure/file.prompt")
     assert "Access denied" in str(ei.value)
 
     c.http_handler.routes[raw_url] = FakeResponse(status_code=401)
-    with pytest.raises(Exception) as ei2:
+    with pytest.raises(Exception, match='Authentication failed\\. Check your GitLab token and') as ei2:
         c.get_file_content("secure/file.prompt")
     assert "Authentication failed" in str(ei2.value)
 
diff --git a/tests/test_litellm/integrations/levo/test_levo.py b/tests/test_litellm/integrations/levo/test_levo.py
index 98b0327dbf2..903be644671 100644
--- a/tests/test_litellm/integrations/levo/test_levo.py
+++ b/tests/test_litellm/integrations/levo/test_levo.py
@@ -198,7 +198,7 @@ class TestLevoIntegration(unittest.TestCase):
         """Test health check returns unhealthy status when required vars are missing."""
         # Try to create logger without required env vars
         # This should fail during config, but we can test health check logic
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='LEVOAI_API_KEY environment variable is required for Levo'):
             LevoLogger.get_levo_config()
 
     @patch.dict(
diff --git a/tests/test_litellm/integrations/otel/test_otel_v2_metrics.py b/tests/test_litellm/integrations/otel/test_otel_v2_metrics.py
index e1b8e4b5721..b810ffdc6be 100644
--- a/tests/test_litellm/integrations/otel/test_otel_v2_metrics.py
+++ b/tests/test_litellm/integrations/otel/test_otel_v2_metrics.py
@@ -554,7 +554,7 @@ def test_token_type_rejected_from_either_list(attributes, monkeypatch):
     recorder rather than silently ignored, so the misconfig is caught at all."""
     recorder = _recorder(monkeypatch, attributes)
     kwargs, response_obj, start, end = _build_call()
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='otel\\.attributes: gen_ai\\.token\\.type is a structural') as exc_info:
         recorder.record(kwargs, response_obj, start, end)
     # The dedicated discriminator guard, not the generic unknown-name path: assert
     # the specific reason so dropping that guard (and falling through to "unknown
diff --git a/tests/test_litellm/integrations/test_langfuse.py b/tests/test_litellm/integrations/test_langfuse.py
index 6e57a36c5b6..3c7dd51bff8 100644
--- a/tests/test_litellm/integrations/test_langfuse.py
+++ b/tests/test_litellm/integrations/test_langfuse.py
@@ -1163,7 +1163,7 @@ def test_max_langfuse_clients_limit():
         assert litellm.initialized_langfuse_clients == 2
 
         # Third client should fail with exception
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Max langfuse clients reached') as exc_info:
             logger3 = LangFuseLogger(
                 langfuse_public_key="test_key_3",
                 langfuse_secret="test_secret_3",
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 fffbc884782..08d8c17cc2e 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
@@ -1169,7 +1169,7 @@ def test_bedrock_image_processor_content_type_fallback_failure():
     # Test with URL without recognizable extension
     image_url = "https://example.com/unknown-file"
 
-    with pytest.raises(ValueError) as excinfo:
+    with pytest.raises(ValueError, match='Unable to determine content type from URL: https') as excinfo:
         BedrockImageProcessor._post_call_image_processing(mock_response, image_url)
 
     assert "Unable to determine content type" in str(excinfo.value)
diff --git a/tests/test_litellm/litellm_core_utils/test_initialize_dynamic_callback_params.py b/tests/test_litellm/litellm_core_utils/test_initialize_dynamic_callback_params.py
index 0dca4f3a1b1..956f86a9292 100644
--- a/tests/test_litellm/litellm_core_utils/test_initialize_dynamic_callback_params.py
+++ b/tests/test_litellm/litellm_core_utils/test_initialize_dynamic_callback_params.py
@@ -110,7 +110,7 @@ def test_top_level_kwargs_overrides_metadata_slots():
 def test_env_reference_at_top_level_raises_with_guidance():
     kwargs = {"langfuse_public_key": "os.environ/LANGFUSE_PUBLIC_KEY"}
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="Callback param 'langfuse_public_key' \\(from request body\\)") as exc_info:
         initialize_standard_callback_dynamic_params(kwargs)
 
     message = str(exc_info.value)
@@ -127,7 +127,7 @@ def test_env_reference_in_metadata_raises_with_guidance():
         }
     }
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match="Callback param 'langsmith_api_key' \\(from metadata\\) contains") as exc_info:
         initialize_standard_callback_dynamic_params(kwargs)
 
     message = str(exc_info.value)
diff --git a/tests/test_litellm/litellm_core_utils/test_llm_judge.py b/tests/test_litellm/litellm_core_utils/test_llm_judge.py
index 5c092caa7c3..a0a2311914b 100644
--- a/tests/test_litellm/litellm_core_utils/test_llm_judge.py
+++ b/tests/test_litellm/litellm_core_utils/test_llm_judge.py
@@ -27,7 +27,7 @@ def test_parse_json_verdict_tolerates_fences_and_prose(raw, expected):
 
 
 def test_parse_json_verdict_rejects_non_object():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='judge response is not a JSON object'):
         parse_json_verdict('["not", "an", "object"]')
     with pytest.raises((json.JSONDecodeError, ValueError)):
         parse_json_verdict("no json here at all")
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 456d4db4afe..fbdfcac1adc 100644
--- a/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
+++ b/tests/test_litellm/litellm_core_utils/test_streaming_handler.py
@@ -982,7 +982,7 @@ async def test_bedrock_validation_error_raises_directly(logging_obj: Logging):
         make_call=_raise_400,
     )
 
-    with pytest.raises(Exception) as excinfo:
+    with pytest.raises(Exception, match='litellm\\.BadRequestError: BedrockException') as excinfo:
         await response.__anext__()
     assert not isinstance(excinfo.value, MidStreamFallbackError)
     assert getattr(excinfo.value, "status_code", None) == 400
@@ -2722,7 +2722,7 @@ def test_dispatch_text_completion_codestral_requires_string(
     is a programming error and must surface loudly."""
     initialized_custom_stream_wrapper.custom_llm_provider = "text-completion-codestral"
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="chunk is not a string: \\{'not': 'a string'\\}"):
         _run_dispatch(initialized_custom_stream_wrapper, {"not": "a string"})
 
 
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 3c33ee13c3f..eec4b307c87 100644
--- a/tests/test_litellm/litellm_core_utils/test_token_counter.py
+++ b/tests/test_litellm/litellm_core_utils/test_token_counter.py
@@ -763,24 +763,6 @@ class TestTokenizerSelection(unittest.TestCase):
                 ],
             }
         ],
-        [
-            {
-                "role": "user",
-                "content": [
-                    {
-                        "type": "text",
-                        "text": "These are some sample images from a movie. Based on these images, what do you think the tone of the movie is?",
-                    },
-                    {
-                        "type": "text",
-                        "image_url": {
-                            "url": "https://gratisography.com/wp-content/uploads/2024/11/gratisography-augmented-reality-800x525.jpg",
-                            "detail": "high",
-                        },
-                    },
-                ],
-            }
-        ],
     ],
 )
 def test_bad_input_token_counter(model, messages):
@@ -1174,7 +1156,7 @@ def test_count_content_list_rejects_unknown_type():
     """
     from litellm.litellm_core_utils.token_counter import _count_content_list
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Error getting number of tokens from content list: Invalid') as exc_info:
         _count_content_list(
             count_function=len,
             content_list=[{"type": "totally_unknown_block"}],
diff --git a/tests/test_litellm/litellm_core_utils/test_url_utils.py b/tests/test_litellm/litellm_core_utils/test_url_utils.py
index cef09f3f2b0..751b548adcd 100644
--- a/tests/test_litellm/litellm_core_utils/test_url_utils.py
+++ b/tests/test_litellm/litellm_core_utils/test_url_utils.py
@@ -100,12 +100,12 @@ class TestEncodeUrlPathSegment:
 
     @pytest.mark.parametrize("value", ["", ".", "..", None])
     def test_rejects_empty_and_dot_segments(self, value):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="resource_id (is required|cannot be a dot path segment)"):
             encode_url_path_segment(value, field_name="resource_id")
 
     @pytest.mark.parametrize("value", ["../model", "model/../other", "/model"])
     def test_rejects_dot_segments_in_multi_segment_paths(self, value):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="model (is required|cannot be a dot path segment)"):
             encode_url_path_segments(value, field_name="model")
 
 
diff --git a/tests/test_litellm/llms/aiml/image_generation/test_aiml_image_generation_transformation.py b/tests/test_litellm/llms/aiml/image_generation/test_aiml_image_generation_transformation.py
index 7485f2121df..dd74379a883 100644
--- a/tests/test_litellm/llms/aiml/image_generation/test_aiml_image_generation_transformation.py
+++ b/tests/test_litellm/llms/aiml/image_generation/test_aiml_image_generation_transformation.py
@@ -113,7 +113,7 @@ def test_flux_style_request_still_remaps_to_legacy_fields():
 
 
 def test_openai_style_unsupported_param_raises_without_drop_params():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Supported parameters are'):
         AimlImageGenerationConfig().map_openai_params(
             non_default_params={"image_size": {"width": 1024, "height": 1024}},
             optional_params={},
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mcp_handler.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mcp_handler.py
index 654b0097546..f3cb2956aeb 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mcp_handler.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/messages/test_mcp_handler.py
@@ -61,7 +61,7 @@ def test_anthropic_messages_handler_skips_the_gateway_on_recursion():
         "litellm.llms.anthropic.experimental_pass_through.messages.mcp_handler.anthropic_messages_with_mcp",
         new=AsyncMock(return_value={"routed": True}),
     ) as routed:
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='anthropic_messages_handler is not implemented for sync calls'):
             anthropic_messages_handler(
                 max_tokens=100,
                 messages=[{"role": "user", "content": "hi"}],
@@ -80,7 +80,7 @@ def test_anthropic_messages_handler_leaves_native_tools_alone():
         "litellm.llms.anthropic.experimental_pass_through.messages.mcp_handler.anthropic_messages_with_mcp",
         new=AsyncMock(return_value={"routed": True}),
     ) as routed:
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='anthropic_messages_handler is not implemented for sync calls'):
             anthropic_messages_handler(
                 max_tokens=100,
                 messages=[{"role": "user", "content": "hi"}],
diff --git a/tests/test_litellm/llms/azure_ai/rerank/test_azure_ai_rerank_transformation.py b/tests/test_litellm/llms/azure_ai/rerank/test_azure_ai_rerank_transformation.py
index ffabce6e00c..602cbf68f3f 100644
--- a/tests/test_litellm/llms/azure_ai/rerank/test_azure_ai_rerank_transformation.py
+++ b/tests/test_litellm/llms/azure_ai/rerank/test_azure_ai_rerank_transformation.py
@@ -16,7 +16,7 @@ class TestAzureAIRerankConfigGetCompleteUrl:
         self.model = "azure_ai/cohere-rerank-v3-english"
 
     def test_api_base_required(self):
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Azure AI API Base is required\\. api_base=None\\. Set in') as exc_info:
             self.config.get_complete_url(api_base=None, model=self.model)
 
         assert "api_base=None" in str(exc_info.value)
@@ -31,7 +31,7 @@ class TestAzureAIRerankConfigGetCompleteUrl:
         ],
     )
     def test_api_base_requires_scheme(self, api_base):
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Azure AI API Base must be an absolute URL including scheme') as exc_info:
             self.config.get_complete_url(api_base=api_base, model=self.model)
 
         error_message = str(exc_info.value).lower()
diff --git a/tests/test_litellm/llms/bedrock/chat/test_invoke_handler.py b/tests/test_litellm/llms/bedrock/chat/test_invoke_handler.py
index ee50b9db015..e8964910c69 100644
--- a/tests/test_litellm/llms/bedrock/chat/test_invoke_handler.py
+++ b/tests/test_litellm/llms/bedrock/chat/test_invoke_handler.py
@@ -2,17 +2,20 @@ import os
 import sys
 from unittest.mock import AsyncMock, MagicMock
 
+import httpx
 import pytest
 
 sys.path.insert(
     0, os.path.abspath("../../../../..")
 )  # Adds the parent directory to the system path
 
+import litellm
 from litellm.llms.bedrock.chat.invoke_handler import (
     AWSEventStreamDecoder,
     make_call,
     make_sync_call,
 )
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
 
 
 def test_transform_thinking_blocks_with_redacted_content():
@@ -293,3 +296,50 @@ def test_make_sync_call_honors_explicit_stream_chunk_size():
 
     response.iter_bytes.assert_called_once_with(chunk_size=2048)
 
+
+def test_invoke_streaming_forwards_bedrock_response_headers():
+    response = MagicMock()
+    response.status_code = 200
+    response.iter_bytes = MagicMock(return_value=iter([]))
+    response.headers = httpx.Headers({"x-amzn-requestid": "req-789"})
+    client = HTTPHandler()
+    client.post = MagicMock(return_value=response)
+
+    stream = litellm.completion(
+        model="bedrock/invoke/anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        stream=True,
+        client=client,
+        aws_access_key_id="fake",
+        aws_secret_access_key="fake",
+        aws_region_name="us-east-1",
+    )
+
+    assert stream._hidden_params["additional_headers"]["llm_provider-x-amzn-requestid"] == "req-789"
+
+
+@pytest.mark.asyncio
+async def test_async_invoke_streaming_forwards_bedrock_response_headers():
+    async def _no_bytes(chunk_size=None):
+        return
+        yield b""
+
+    response = MagicMock()
+    response.status_code = 200
+    response.aiter_bytes = _no_bytes
+    response.headers = httpx.Headers({"x-amzn-requestid": "req-987"})
+    client = AsyncHTTPHandler()
+    client.post = AsyncMock(return_value=response)
+
+    stream = await litellm.acompletion(
+        model="bedrock/invoke/anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        stream=True,
+        client=client,
+        aws_access_key_id="fake",
+        aws_secret_access_key="fake",
+        aws_region_name="us-east-1",
+    )
+
+    assert stream._hidden_params["additional_headers"]["llm_provider-x-amzn-requestid"] == "req-987"
+
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 cfe9930e76e..b9f8283b78e 100644
--- a/tests/test_litellm/llms/bedrock/test_base_aws_llm.py
+++ b/tests/test_litellm/llms/bedrock/test_base_aws_llm.py
@@ -1944,7 +1944,7 @@ def test_role_assumption_access_denied_raises_when_different_role():
         with patch.object(
             base_aws_llm, "_is_already_running_as_role", return_value=False
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='An error occurred \\(AccessDenied\\) when calling the') as exc_info:
                 base_aws_llm._auth_with_aws_role(
                     aws_access_key_id=None,
                     aws_secret_access_key=None,
@@ -1969,7 +1969,7 @@ def test_role_assumption_non_access_denied_error_propagated():
     )
 
     with patch("boto3.client", return_value=mock_sts_client):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='An error occurred \\(MalformedPolicyDocument\\) when calling') as exc_info:
             base_aws_llm._auth_with_aws_role(
                 aws_access_key_id=None,
                 aws_secret_access_key=None,
diff --git a/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_responses_transformation.py b/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_responses_transformation.py
index 8281f3387d9..28c8e5c7ed6 100644
--- a/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_responses_transformation.py
+++ b/tests/test_litellm/llms/bedrock_mantle/test_bedrock_mantle_responses_transformation.py
@@ -109,7 +109,7 @@ class TestBedrockMantleResponsesURL:
         monkeypatch.delenv("BEDROCK_MANTLE_API_BASE", raising=False)
         monkeypatch.delenv("AWS_REGION", raising=False)
         cfg = BedrockMantleResponsesAPIConfig()
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="api\\.aws\\.attacker\\.example/'\\. Region names must contain only"):
             cfg.get_complete_url(
                 api_base=None,
                 litellm_params={
@@ -1418,7 +1418,7 @@ class TestBedrockMantleResponsesSigV4:
         signer.get_credentials = MagicMock(side_effect=NoCredentialsError())
         cfg = BedrockMantleResponsesAPIConfig(aws_signer=signer)
 
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Bedrock Mantle auth failed: no Bearer token and no usable') as exc:
             cfg.sign_request(
                 headers={},
                 optional_params={"aws_region_name": "us-east-2"},
@@ -1448,7 +1448,7 @@ class TestBedrockMantleResponsesSigV4:
         signer.get_credentials = MagicMock(side_effect=cred_error)
         cfg = BedrockMantleResponsesAPIConfig(aws_signer=signer)
 
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Bedrock Mantle auth failed: no Bearer token and no usable') as exc:
             cfg.sign_request(
                 headers={},
                 optional_params={"aws_region_name": "us-east-2"},
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 275fb460b9f..07910b0b56f 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
@@ -107,7 +107,7 @@ class TestBedrockMantleConfig:
         monkeypatch.delenv("BEDROCK_MANTLE_API_BASE", raising=False)
         monkeypatch.delenv("AWS_REGION", raising=False)
         cfg = BedrockMantleChatConfig()
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="api\\.aws\\.attacker\\.example/'\\. Region names must contain only"):
             cfg._get_openai_compatible_provider_info(
                 None,
                 None,
@@ -416,7 +416,7 @@ class TestBedrockMantleChatAuth:
         signer.get_credentials = MagicMock(side_effect=NoCredentialsError())
         cfg = BedrockMantleChatConfig(aws_signer=signer)
 
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Bedrock Mantle auth failed: no Bearer token and no usable') as exc:
             cfg.sign_request(
                 headers={},
                 optional_params={"aws_region_name": "us-east-2"},
diff --git a/tests/test_litellm/llms/bytez/chat/test_bytez_chat_transformation.py b/tests/test_litellm/llms/bytez/chat/test_bytez_chat_transformation.py
index e2421437720..94b8c51dd52 100644
--- a/tests/test_litellm/llms/bytez/chat/test_bytez_chat_transformation.py
+++ b/tests/test_litellm/llms/bytez/chat/test_bytez_chat_transformation.py
@@ -38,7 +38,7 @@ class TestBytezChatConfig:
         config = BytezChatConfig()
         headers = {}
 
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match='Missing api_key, make sure you pass in your api key') as excinfo:
             config.validate_environment(
                 headers=headers,
                 model=TEST_MODEL,
diff --git a/tests/test_litellm/llms/chat/test_converse_handler.py b/tests/test_litellm/llms/chat/test_converse_handler.py
index 2a3db5982ef..6f8a2788c38 100644
--- a/tests/test_litellm/llms/chat/test_converse_handler.py
+++ b/tests/test_litellm/llms/chat/test_converse_handler.py
@@ -1,14 +1,16 @@
+import json
 import os
 import sys
-from unittest.mock import MagicMock
+from unittest.mock import AsyncMock, MagicMock
 
+import httpx
 import pytest
 
 import litellm
 from litellm.llms.bedrock.chat import BedrockConverseLLM
 from litellm.llms.bedrock.chat.converse_handler import make_sync_call
 from litellm.llms.bedrock.common_utils import _get_all_bedrock_regions
-from litellm.llms.custom_httpx.http_handler import HTTPHandler
+from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler, HTTPHandler
 
 sys.path.insert(
     0, os.path.abspath("../../../../..")
@@ -202,6 +204,104 @@ def test_make_sync_call_honors_explicit_stream_chunk_size():
     response.iter_bytes.assert_called_once_with(chunk_size=2048)
 
 
+def _converse_response_body() -> dict:
+    return {
+        "output": {"message": {"role": "assistant", "content": [{"text": "hi"}]}},
+        "stopReason": "end_turn",
+        "usage": {"inputTokens": 1, "outputTokens": 1, "totalTokens": 2},
+    }
+
+
+def test_converse_completion_forwards_bedrock_response_headers():
+    mock_response = MagicMock()
+    mock_response.status_code = 200
+    mock_response.json = MagicMock(return_value=_converse_response_body())
+    mock_response.text = json.dumps(_converse_response_body())
+    mock_response.headers = httpx.Headers({"x-amzn-requestid": "req-123"})
+    client = HTTPHandler()
+    client.post = MagicMock(return_value=mock_response)
+
+    response = litellm.completion(
+        model="bedrock/converse/anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        client=client,
+        aws_access_key_id="fake",
+        aws_secret_access_key="fake",
+        aws_region_name="us-east-1",
+    )
+
+    assert response._hidden_params["additional_headers"]["llm_provider-x-amzn-requestid"] == "req-123"
+
+
+def test_converse_streaming_forwards_bedrock_response_headers():
+    mock_response = MagicMock()
+    mock_response.status_code = 200
+    mock_response.iter_bytes = MagicMock(return_value=iter([]))
+    mock_response.headers = httpx.Headers({"x-amzn-requestid": "req-456"})
+    client = HTTPHandler()
+    client.post = MagicMock(return_value=mock_response)
+
+    response = litellm.completion(
+        model="bedrock/converse/anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        stream=True,
+        client=client,
+        aws_access_key_id="fake",
+        aws_secret_access_key="fake",
+        aws_region_name="us-east-1",
+    )
+
+    assert response._hidden_params["additional_headers"]["llm_provider-x-amzn-requestid"] == "req-456"
+
+
+@pytest.mark.asyncio
+async def test_async_converse_completion_forwards_bedrock_response_headers():
+    mock_response = MagicMock()
+    mock_response.status_code = 200
+    mock_response.json = MagicMock(return_value=_converse_response_body())
+    mock_response.text = json.dumps(_converse_response_body())
+    mock_response.headers = httpx.Headers({"x-amzn-requestid": "req-abc"})
+    client = AsyncHTTPHandler()
+    client.post = AsyncMock(return_value=mock_response)
+
+    response = await litellm.acompletion(
+        model="bedrock/converse/anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        client=client,
+        aws_access_key_id="fake",
+        aws_secret_access_key="fake",
+        aws_region_name="us-east-1",
+    )
+
+    assert response._hidden_params["additional_headers"]["llm_provider-x-amzn-requestid"] == "req-abc"
+
+
+@pytest.mark.asyncio
+async def test_async_converse_streaming_forwards_bedrock_response_headers():
+    async def _no_bytes(chunk_size=None):
+        return
+        yield b""
+
+    mock_response = MagicMock()
+    mock_response.status_code = 200
+    mock_response.aiter_bytes = _no_bytes
+    mock_response.headers = httpx.Headers({"x-amzn-requestid": "req-def"})
+    client = AsyncHTTPHandler()
+    client.post = AsyncMock(return_value=mock_response)
+
+    response = await litellm.acompletion(
+        model="bedrock/converse/anthropic.claude-haiku-4-5-20251001-v1:0",
+        messages=[{"role": "user", "content": "hi"}],
+        stream=True,
+        client=client,
+        aws_access_key_id="fake",
+        aws_secret_access_key="fake",
+        aws_region_name="us-east-1",
+    )
+
+    assert response._hidden_params["additional_headers"]["llm_provider-x-amzn-requestid"] == "req-def"
+
+
 def test_completion_plumbs_stream_chunk_size_through_converse():
     iter_bytes_spy = _stream_completion_with_spied_iter_bytes(
         model="bedrock/anthropic.claude-3-5-sonnet-20240620-v1:0"
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 c568b82ebba..c87abbd8bc4 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
@@ -2369,3 +2369,79 @@ async def test_async_anthropic_messages_handler_carries_deployment_vertex_locati
 
     unconfigured_deployment = await logging_obj_after_handler(GenericLiteLLMParams())
     assert "vertex_location" not in unconfigured_deployment.litellm_params
+
+
+_GENERIC_STREAM_SSE = (
+    b'data: {"id":"chatcmpl-1","object":"chat.completion.chunk","created":1,'
+    b'"model":"test-model","choices":[{"index":0,"delta":{"content":"hi"},'
+    b'"finish_reason":null}]}\n\n'
+    b"data: [DONE]\n\n"
+)
+
+
+def _generic_stream_upstream_response() -> httpx.Response:
+    return httpx.Response(
+        200,
+        headers={
+            "x-request-id": "generic-req-123",
+            "x-ratelimit-remaining-requests": "42",
+        },
+        content=_GENERIC_STREAM_SSE,
+        request=httpx.Request("POST", "https://fake-vllm.test/v1/chat/completions"),
+    )
+
+
+def test_generic_http_handler_sync_streaming_forwards_provider_response_headers():
+    """
+    Regression test for the generic BaseLLMHTTPHandler streaming path used by
+    ~30 providers (deepseek, groq, hosted_vllm, databricks, openrouter, ...).
+
+    The sync `completion()` streaming branch builds the CustomStreamWrapper from
+    `make_sync_call`, which returns the upstream response headers alongside the
+    stream. Those headers must reach the caller as `llm_provider-*` entries in
+    `_hidden_params["additional_headers"]`, which is what the proxy merges into
+    the client-facing response headers.
+    """
+    mock_client = Mock(spec=HTTPHandler)
+    mock_client.post = Mock(return_value=_generic_stream_upstream_response())
+
+    response = litellm.completion(
+        model="hosted_vllm/test-model",
+        messages=[{"role": "user", "content": "Hello"}],
+        api_base="https://fake-vllm.test/v1",
+        api_key="sk-test",
+        stream=True,
+        client=mock_client,
+    )
+
+    additional_headers = response._hidden_params["additional_headers"]
+    assert additional_headers["llm_provider-x-request-id"] == "generic-req-123"
+    assert additional_headers["llm_provider-x-ratelimit-remaining-requests"] == "42"
+
+    assert "".join([chunk.choices[0].delta.content or "" for chunk in response]) == "hi"
+
+
+@pytest.mark.asyncio
+async def test_generic_http_handler_async_streaming_forwards_provider_response_headers():
+    """
+    Companion to the sync test above for `acompletion_stream_function`, which
+    builds its CustomStreamWrapper from `make_async_call_stream_helper`.
+    """
+    mock_client = AsyncMock(spec=AsyncHTTPHandler)
+    mock_client.post = AsyncMock(return_value=_generic_stream_upstream_response())
+
+    response = await litellm.acompletion(
+        model="hosted_vllm/test-model",
+        messages=[{"role": "user", "content": "Hello"}],
+        api_base="https://fake-vllm.test/v1",
+        api_key="sk-test",
+        stream=True,
+        client=mock_client,
+    )
+
+    additional_headers = response._hidden_params["additional_headers"]
+    assert additional_headers["llm_provider-x-request-id"] == "generic-req-123"
+    assert additional_headers["llm_provider-x-ratelimit-remaining-requests"] == "42"
+
+    collected = [chunk async for chunk in response]
+    assert "".join([chunk.choices[0].delta.content or "" for chunk in collected]) == "hi"
diff --git a/tests/test_litellm/llms/deepinfra/test_deepinfra_rerank_transformation.py b/tests/test_litellm/llms/deepinfra/test_deepinfra_rerank_transformation.py
index a5411078cf7..ae3c166e7aa 100644
--- a/tests/test_litellm/llms/deepinfra/test_deepinfra_rerank_transformation.py
+++ b/tests/test_litellm/llms/deepinfra/test_deepinfra_rerank_transformation.py
@@ -258,7 +258,7 @@ class TestDeepinfraRerankTransform:
         status_code = 401
         headers = {"content-type": "application/json"}
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Authentication failed') as exc_info:
             self.config.get_error_class(error_message, status_code, headers)
 
         # The method should raise a BaseLLMException
@@ -271,7 +271,7 @@ class TestDeepinfraRerankTransform:
         status_code = 404
         headers = {"content-type": "application/json"}
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Model not found') as exc_info:
             self.config.get_error_class(error_message, status_code, headers)
 
         # Should extract the nested error message
@@ -284,7 +284,7 @@ class TestDeepinfraRerankTransform:
         status_code = 503
         headers = {"content-type": "application/json"}
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Service unavailable') as exc_info:
             self.config.get_error_class(error_message, status_code, headers)
 
         # Should extract the string detail
@@ -296,7 +296,7 @@ class TestDeepinfraRerankTransform:
         status_code = 500
         headers = {"content-type": "application/json"}
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Invalid JSON error message') as exc_info:
             self.config.get_error_class(error_message, status_code, headers)
 
         # Should use the original error message when JSON parsing fails
diff --git a/tests/test_litellm/llms/fal_ai/image_generation/test_fal_ai_nano_banana_transformation.py b/tests/test_litellm/llms/fal_ai/image_generation/test_fal_ai_nano_banana_transformation.py
index 593593bfa73..c0f74eff51b 100644
--- a/tests/test_litellm/llms/fal_ai/image_generation/test_fal_ai_nano_banana_transformation.py
+++ b/tests/test_litellm/llms/fal_ai/image_generation/test_fal_ai_nano_banana_transformation.py
@@ -113,7 +113,7 @@ def test_response_format_is_ignored():
 
 
 def test_unsupported_param_raises_without_drop_params():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="Supported parameters are \\['n', 'response_format', 'size'\\]\\."):
         FalAINanoBananaConfig().map_openai_params(
             non_default_params={"style": "vivid"},
             optional_params={},
diff --git a/tests/test_litellm/llms/featherless_ai/chat/test_featherless_chat_transformation.py b/tests/test_litellm/llms/featherless_ai/chat/test_featherless_chat_transformation.py
index 4dc467575a0..bf40abd7016 100644
--- a/tests/test_litellm/llms/featherless_ai/chat/test_featherless_chat_transformation.py
+++ b/tests/test_litellm/llms/featherless_ai/chat/test_featherless_chat_transformation.py
@@ -44,7 +44,7 @@ class TestFeatherlessAIConfig:
         """Test error handling when API key is missing"""
         config = FeatherlessAIConfig()
 
-        with pytest.raises(ValueError) as excinfo:
+        with pytest.raises(ValueError, match='Missing Featherless AI API Key') as excinfo:
             config.validate_environment(
                 headers={},
                 model="featherless-ai/Qwerky-72B",
@@ -112,7 +112,7 @@ class TestFeatherlessAIConfig:
             "tool_choice": {"type": "function", "function": {"name": "get_weather"}}
         }
         optional_params = {}
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match="litellm\\.UnsupportedParamsError: Featherless AI doesn't") as excinfo:
             config.map_openai_params(
                 non_default_params=non_default_params,
                 optional_params=optional_params,
@@ -138,7 +138,7 @@ class TestFeatherlessAIConfig:
         assert "tools" not in result
 
         # Test with tools and drop_params=False
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match="litellm\\.UnsupportedParamsError: Featherless AI doesn't") as excinfo:
             config.map_openai_params(
                 non_default_params=non_default_params,
                 optional_params=optional_params,
diff --git a/tests/test_litellm/llms/fireworks_ai/rerank/test_fireworks_ai_rerank_transformation.py b/tests/test_litellm/llms/fireworks_ai/rerank/test_fireworks_ai_rerank_transformation.py
index 30bf5860dee..521ea4f8263 100644
--- a/tests/test_litellm/llms/fireworks_ai/rerank/test_fireworks_ai_rerank_transformation.py
+++ b/tests/test_litellm/llms/fireworks_ai/rerank/test_fireworks_ai_rerank_transformation.py
@@ -301,7 +301,7 @@ class TestFireworksAIRerankTransform:
         mock_logging = MagicMock()
         model_response = RerankResponse()
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Failed to parse response: Invalid JSON: line') as exc_info:
             self.config.transform_rerank_response(
                 model=self.model,
                 raw_response=mock_response,
diff --git a/tests/test_litellm/llms/gemini/image_edit/test_gemini_image_edit_transformation.py b/tests/test_litellm/llms/gemini/image_edit/test_gemini_image_edit_transformation.py
index 9b57e1991de..bd9b7006e58 100644
--- a/tests/test_litellm/llms/gemini/image_edit/test_gemini_image_edit_transformation.py
+++ b/tests/test_litellm/llms/gemini/image_edit/test_gemini_image_edit_transformation.py
@@ -244,7 +244,7 @@ class TestGeminiImageEditTransformation:
     def test_transform_image_edit_request_without_image_raises(self) -> None:
         optional_params = {}
 
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='Gemini image edit requires at least one image\\.'):
             self.config.transform_image_edit_request(
                 model=self.model,
                 prompt=self.prompt,
diff --git a/tests/test_litellm/llms/gemini/test_gemini_client_setup.py b/tests/test_litellm/llms/gemini/test_gemini_client_setup.py
index 51c6fedf5b8..48b010aca48 100644
--- a/tests/test_litellm/llms/gemini/test_gemini_client_setup.py
+++ b/tests/test_litellm/llms/gemini/test_gemini_client_setup.py
@@ -28,7 +28,7 @@ def test_gemini_completion_no_api_key():
                 del os.environ[key]
 
         # Test without mock_response to ensure actual API key validation
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='in _complete_vertex_ai_beta') as exc_info:
             completion(
                 model="gemini/gemini-1.5-flash",
                 messages=[{"role": "user", "content": "Test message"}],
@@ -60,7 +60,7 @@ def test_gemini_completion_no_api_key_with_mock():
         with patch("litellm.get_secret") as mock_get_secret:
             mock_get_secret.return_value = None
 
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='in _complete_vertex_ai_beta') as exc_info:
                 completion(
                     model="gemini/gemini-1.5-flash",
                     messages=[{"role": "user", "content": "Test message"}],
diff --git a/tests/test_litellm/llms/hosted_vllm/test_hosted_vllm_rerank_transformation.py b/tests/test_litellm/llms/hosted_vllm/test_hosted_vllm_rerank_transformation.py
index 6425e815db0..e6e6aa946d5 100644
--- a/tests/test_litellm/llms/hosted_vllm/test_hosted_vllm_rerank_transformation.py
+++ b/tests/test_litellm/llms/hosted_vllm/test_hosted_vllm_rerank_transformation.py
@@ -109,7 +109,7 @@ class TestHostedVLLMRerankTransform:
         )
         assert url2 == "https://api.example.com/rerank"
         # Raises if api_base is None
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='api_base must be provided for Hosted VLLM rerank'):
             self.config.get_complete_url(None, self.model)
 
     def test_transform_response(self):
diff --git a/tests/test_litellm/llms/langflow/chat/test_langflow_chat_transformation.py b/tests/test_litellm/llms/langflow/chat/test_langflow_chat_transformation.py
index b3c4e0f1858..0c241add77b 100644
--- a/tests/test_litellm/llms/langflow/chat/test_langflow_chat_transformation.py
+++ b/tests/test_litellm/llms/langflow/chat/test_langflow_chat_transformation.py
@@ -46,7 +46,7 @@ def test_langflow_config_get_complete_url():
 
 def test_langflow_config_get_complete_url_requires_api_base():
     config = LangFlowConfig()
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='api_base is required for LangFlow\\. Set it via'):
         config.get_complete_url(
             api_base=None,
             api_key=None,
diff --git a/tests/test_litellm/llms/modelscope/image_generation/test_modelscope_image_gen_transformation.py b/tests/test_litellm/llms/modelscope/image_generation/test_modelscope_image_gen_transformation.py
index 7f00f53c451..fbcec3d4d2e 100644
--- a/tests/test_litellm/llms/modelscope/image_generation/test_modelscope_image_gen_transformation.py
+++ b/tests/test_litellm/llms/modelscope/image_generation/test_modelscope_image_gen_transformation.py
@@ -154,7 +154,7 @@ class TestModelScopeImageGenerationTransformation:
         mock_get_secret.return_value = None
         headers = {}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='MODELSCOPE_API_KEY is not set\\. Please set it via') as exc_info:
             self.config.validate_environment(
                 headers=headers,
                 model=self.model,
@@ -367,7 +367,7 @@ class TestModelScopeImageGenerationTransformation:
 
         model_response = ImageResponse(data=[])
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='litellm\\.BadRequestError: ModelScope error: Invalid prompt') as exc_info:
             self.config.transform_image_generation_response(
                 model=self.model,
                 raw_response=mock_response,
@@ -393,7 +393,7 @@ class TestModelScopeImageGenerationTransformation:
 
         model_response = ImageResponse(data=[])
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='litellm\\.InternalServerError: Error parsing ModelScope') as exc_info:
             self.config.transform_image_generation_response(
                 model=self.model,
                 raw_response=mock_response,
diff --git a/tests/test_litellm/llms/novita/chat/test_novita_chat_transformation.py b/tests/test_litellm/llms/novita/chat/test_novita_chat_transformation.py
index 7a00b361252..ade5e4176e8 100644
--- a/tests/test_litellm/llms/novita/chat/test_novita_chat_transformation.py
+++ b/tests/test_litellm/llms/novita/chat/test_novita_chat_transformation.py
@@ -47,7 +47,7 @@ class TestNovitaConfig:
         """Test error handling when API key is missing"""
         config = NovitaConfig()
 
-        with pytest.raises(ValueError) as excinfo:
+        with pytest.raises(ValueError, match='Missing Novita AI API Key - A call is being made to novita') as excinfo:
             config.validate_environment(
                 headers={},
                 model="novita/meta-llama/llama-3.3-70b-instruct",
diff --git a/tests/test_litellm/llms/oci/chat/test_oci_chat_transformation.py b/tests/test_litellm/llms/oci/chat/test_oci_chat_transformation.py
index 8be0780d86f..5aa96a66d2d 100644
--- a/tests/test_litellm/llms/oci/chat/test_oci_chat_transformation.py
+++ b/tests/test_litellm/llms/oci/chat/test_oci_chat_transformation.py
@@ -98,7 +98,7 @@ class TestOCIChatConfig:
             config = OCIChatConfig()
             headers = {}
 
-            with pytest.raises(Exception) as excinfo:
+            with pytest.raises(Exception, match='Missing required parameters: oci_user, oci_fingerprint') as excinfo:
                 config.validate_environment(
                     headers=headers,
                     model=TEST_MODEL,
@@ -272,7 +272,7 @@ class TestOCIChatConfig:
             "oci_serving_mode": "INVALID_MODE",
         }
 
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match="kwarg `oci_serving_mode` must be either 'ON_DEMAND' or") as excinfo:
             config.transform_request(
                 model=TEST_MODEL_NAME,
                 messages=TEST_MESSAGES,  # type: ignore
@@ -892,7 +892,7 @@ class TestOCISignerSupport:
 
         optional_params = {"oci_signer": MockSigner(), "method": "INVALID"}
 
-        with pytest.raises(ValueError) as excinfo:
+        with pytest.raises(ValueError, match='Unsupported HTTP method: INVALID') as excinfo:
             config.sign_request(
                 headers={},
                 optional_params=optional_params,
@@ -1604,7 +1604,7 @@ class TestOCIKeyNormalization:
 
         # We can't fully test signing without a real key, but we can verify
         # the error message indicates the key was processed (not a type error)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='why-can-t-i-import-my-pem-file for more details\\.') as exc_info:
             sign_with_manual_credentials(
                 headers={},
                 optional_params=optional_params,
@@ -1630,7 +1630,7 @@ class TestOCIKeyNormalization:
             "oci_key": crlf_pem,
         }
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='why-can-t-i-import-my-pem-file for more details\\.') as exc_info:
             sign_with_manual_credentials(
                 headers={},
                 optional_params=optional_params,
@@ -1692,7 +1692,7 @@ class TestOCIValidateEnvironment:
 
     def test_missing_required_credentials_raises_error(self, config):
         """Test that missing required credentials raise an error."""
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Missing required parameters: oci_user, oci_fingerprint') as exc_info:
             config.validate_environment(
                 headers={},
                 model="oci/xai.grok-3",
@@ -1875,7 +1875,7 @@ class TestOCIImageUrlTransformation:
             }
         ]
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Prop `image_url` must be a string or an object with a `url`') as exc_info:
             adapt_messages_to_generic_oci_standard(messages)
 
         assert "image_url" in str(exc_info.value)
@@ -1899,7 +1899,7 @@ class TestOCIImageUrlTransformation:
             }
         ]
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Prop `image_url` must be a string or an object with a `url`') as exc_info:
             adapt_messages_to_generic_oci_standard(messages)
 
         assert "image_url" in str(exc_info.value)
diff --git a/tests/test_litellm/llms/openai_like/test_cognition_provider.py b/tests/test_litellm/llms/openai_like/test_cognition_provider.py
index c358d178f60..5c71b60e08a 100644
--- a/tests/test_litellm/llms/openai_like/test_cognition_provider.py
+++ b/tests/test_litellm/llms/openai_like/test_cognition_provider.py
@@ -111,33 +111,51 @@ class TestCognitionProviderIdentity:
 
 class TestCognitionCostTracking:
     @pytest.mark.parametrize(
-        "model, input_cost, output_cost",
+        "model, input_cost, output_cost, cache_read_cost",
         [
-            ("cognition/swe-1.6", 5e-07, 2.5e-06),
-            ("cognition/swe-1.7", 2.5e-06, 1.25e-05),
+            ("cognition/swe-1.6", 5e-07, 2.5e-06, 2e-07),
+            ("cognition/swe-1.7", 5e-07, 2.5e-06, 2e-07),
+            ("cognition/swe-1.7-lightning", 2.5e-06, 1.25e-05, 1e-06),
         ],
     )
-    def test_cost_map_entries(self, model: str, input_cost: float, output_cost: float):
+    def test_cost_map_entries(self, model: str, input_cost: float, output_cost: float, cache_read_cost: float):
         info = litellm.get_model_info(model=model)
 
         assert info["litellm_provider"] == "cognition"
         assert info["mode"] == "chat"
         assert info["input_cost_per_token"] == input_cost
         assert info["output_cost_per_token"] == output_cost
+        assert info["cache_read_input_token_cost"] == cache_read_cost
 
-    def test_cost_differs_from_openai_pricing(self):
+    @pytest.mark.parametrize(
+        "model, expected_prompt_cost, expected_completion_cost",
+        [
+            ("cognition/swe-1.7", 0.5, 2.5),
+            ("cognition/swe-1.7-lightning", 2.5, 12.5),
+        ],
+    )
+    def test_cost_differs_from_openai_pricing(
+        self, model: str, expected_prompt_cost: float, expected_completion_cost: float
+    ):
         """A cognition-prefixed model must never be priced off an OpenAI cost entry."""
         from litellm.cost_calculator import cost_per_token
 
         prompt_cost, completion_cost = cost_per_token(
-            model="cognition/swe-1.7",
+            model=model,
             prompt_tokens=1_000_000,
             completion_tokens=1_000_000,
             custom_llm_provider="cognition",
         )
 
-        assert prompt_cost == pytest.approx(2.5)
-        assert completion_cost == pytest.approx(12.5)
+        assert prompt_cost == pytest.approx(expected_prompt_cost)
+        assert completion_cost == pytest.approx(expected_completion_cost)
+
+    def test_lightning_is_five_times_the_standard_tier(self):
+        standard = litellm.get_model_info(model="cognition/swe-1.7")
+        lightning = litellm.get_model_info(model="cognition/swe-1.7-lightning")
+
+        assert lightning["input_cost_per_token"] == pytest.approx(standard["input_cost_per_token"] * 5)
+        assert lightning["output_cost_per_token"] == pytest.approx(standard["output_cost_per_token"] * 5)
 
     def test_supported_endpoints_matrix(self):
         matrix = json.loads((Path(litellm.__file__).parent / "provider_endpoints_support_backup.json").read_text())
@@ -170,6 +188,30 @@ class TestCognitionRouting:
             mock_response="hello from swe",
         )
 
+        usage = response.usage
+        expected = usage.prompt_tokens * 5e-07 + usage.completion_tokens * 2.5e-06
+        assert response._hidden_params["response_cost"] == pytest.approx(expected)
+
+    @pytest.mark.asyncio
+    async def test_router_spend_uses_the_lightning_entry_for_lightning(self):
+        """The Lightning tier is its own model, costed off its own entry."""
+        from litellm import Router
+
+        router = Router(
+            model_list=[
+                {
+                    "model_name": "swe-lightning",
+                    "litellm_params": {"model": "cognition/swe-1.7-lightning", "api_key": "sk-test"},
+                }
+            ]
+        )
+
+        response = await router.acompletion(
+            model="swe-lightning",
+            messages=[{"role": "user", "content": "hi"}],
+            mock_response="hello from swe lightning",
+        )
+
         usage = response.usage
         expected = usage.prompt_tokens * 2.5e-06 + usage.completion_tokens * 1.25e-05
         assert response._hidden_params["response_cost"] == pytest.approx(expected)
diff --git a/tests/test_litellm/llms/pg_vector/vector_stores/test_pg_vector_transformation.py b/tests/test_litellm/llms/pg_vector/vector_stores/test_pg_vector_transformation.py
index 56953a574d6..1d44b2bc278 100644
--- a/tests/test_litellm/llms/pg_vector/vector_stores/test_pg_vector_transformation.py
+++ b/tests/test_litellm/llms/pg_vector/vector_stores/test_pg_vector_transformation.py
@@ -42,7 +42,7 @@ class TestPGVectorStoreConfig:
         litellm_params = GenericLiteLLMParams()
         headers = {}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='PG Vector API key is required\\. Set PG_VECTOR_API_KEY') as exc_info:
             config.validate_environment(headers, litellm_params)
 
         assert "PG Vector API key is required" in str(exc_info.value)
@@ -84,7 +84,7 @@ class TestPGVectorStoreConfig:
         config = PGVectorStoreConfig()
         litellm_params = {}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='PG Vector API base URL is required\\. Set') as exc_info:
             config.get_complete_url(None, litellm_params)
 
         assert "PG Vector API base URL is required" in str(exc_info.value)
diff --git a/tests/test_litellm/llms/recraft/image_edit/test_recraft_image_edit_transformation.py b/tests/test_litellm/llms/recraft/image_edit/test_recraft_image_edit_transformation.py
index 0acabd05805..47811321133 100644
--- a/tests/test_litellm/llms/recraft/image_edit/test_recraft_image_edit_transformation.py
+++ b/tests/test_litellm/llms/recraft/image_edit/test_recraft_image_edit_transformation.py
@@ -167,7 +167,7 @@ class TestRecraftImageEditTransformation:
         mock_response.status_code = 500
         mock_response.headers = {}
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Error transforming image edit response: Invalid JSON: line') as exc_info:
             self.config.transform_image_edit_response(
                 model=self.model,
                 raw_response=mock_response,
diff --git a/tests/test_litellm/llms/recraft/image_generation/test_recraft_image_gen_transformation.py b/tests/test_litellm/llms/recraft/image_generation/test_recraft_image_gen_transformation.py
index 70311201969..ccc72dde7b8 100644
--- a/tests/test_litellm/llms/recraft/image_generation/test_recraft_image_gen_transformation.py
+++ b/tests/test_litellm/llms/recraft/image_generation/test_recraft_image_gen_transformation.py
@@ -64,7 +64,7 @@ class TestRecraftImageGenerationTransformation:
         non_default_params = {"n": 2, "unsupported_param": "value"}
         optional_params = {}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Supported parameters are') as exc_info:
             self.config.map_openai_params(
                 non_default_params=non_default_params,
                 optional_params=optional_params,
@@ -171,7 +171,7 @@ class TestRecraftImageGenerationTransformation:
         mock_get_secret.return_value = None
         headers = {}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='RECRAFT_API_KEY is not set') as exc_info:
             self.config.validate_environment(
                 headers=headers,
                 model=self.model,
@@ -248,7 +248,7 @@ class TestRecraftImageGenerationTransformation:
 
         model_response = ImageResponse(data=[])
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Error transforming image generation response: Invalid JSON') as exc_info:
             self.config.transform_image_generation_response(
                 model=self.model,
                 raw_response=mock_response,
diff --git a/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_transformation.py b/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_transformation.py
index 54e6f95c795..da6caca4f05 100644
--- a/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_transformation.py
+++ b/tests/test_litellm/llms/sagemaker/test_sagemaker_chat_transformation.py
@@ -19,6 +19,8 @@ from unittest.mock import MagicMock
 import httpx
 import pytest
 
+import litellm
+from litellm.llms.custom_httpx.http_handler import HTTPHandler
 from litellm.llms.sagemaker.chat.transformation import SagemakerChatConfig
 
 
@@ -233,3 +235,85 @@ def test_decoder_reassembles_frames_across_arbitrary_byte_boundaries(split_size)
     ]
 
     assert texts == [f"token{i} " for i in range(len(frames))]
+
+
+_INFERENCE_COMPONENT_HEADER = "X-Amzn-SageMaker-Inference-Component"
+
+_STUB_COMPLETION_RESPONSE = {
+    "id": "chatcmpl-test",
+    "object": "chat.completion",
+    "created": 1700000000,
+    "model": "served-model",
+    "choices": [{"index": 0, "message": {"role": "assistant", "content": "hi"}, "finish_reason": "stop"}],
+    "usage": {"prompt_tokens": 1, "completion_tokens": 1, "total_tokens": 2},
+}
+
+
+class _RequestCapturingHTTPHandler(HTTPHandler):
+    """Injected transport that records exactly what sagemaker_chat put on the wire."""
+
+    def __init__(self) -> None:
+        super().__init__()
+        self.request_headers: dict[str, str] = {}
+        self.request_body: dict = {}
+
+    def post(self, url: str, headers=None, data=None, **kwargs) -> httpx.Response:
+        self.request_headers = dict(headers or {})
+        self.request_body = json.loads(data)
+        return httpx.Response(200, json=_STUB_COMPLETION_RESPONSE, request=httpx.Request("POST", url))
+
+
+def _invoke_sagemaker_chat(monkeypatch, **extra_params) -> _RequestCapturingHTTPHandler:
+    """Drive one sagemaker_chat completion against an injected transport.
+
+    A Bedrock API key short-circuits SigV4 inside `BaseAWSLLM._sign_request`, which would hide
+    whether the inference-component header is really covered by the signature, so it is cleared.
+    """
+    monkeypatch.delenv("AWS_BEARER_TOKEN_BEDROCK", raising=False)
+    client = _RequestCapturingHTTPHandler()
+    litellm.completion(
+        model="sagemaker_chat/my-endpoint",
+        messages=[{"role": "user", "content": "hi"}],
+        aws_access_key_id="AKIATESTTESTTESTTEST",
+        aws_secret_access_key="test-secret-key",
+        aws_region_name="us-east-1",
+        client=client,
+        **extra_params,
+    )
+    return client
+
+
+def test_model_id_is_sent_as_a_signed_inference_component_header(monkeypatch):
+    """`model_id` names an inference component and must reach SageMaker as a signed header.
+
+    Endpoints backed by inference components reject any request without
+    `X-Amzn-SageMaker-Inference-Component` with HTTP 400 INFERENCE_COMPONENT_NAME_MISSING, so the
+    header has to be built before `sign_request` runs and end up inside SignedHeaders.
+    """
+    client = _invoke_sagemaker_chat(monkeypatch, model_id="my-inference-component")
+
+    assert client.request_headers[_INFERENCE_COMPONENT_HEADER] == "my-inference-component"
+    assert "x-amzn-sagemaker-inference-component" in client.request_headers["Authorization"]
+
+
+def test_no_inference_component_header_when_model_id_is_unset(monkeypatch):
+    """Plain endpoints must not receive the header at all, not even an empty one."""
+    client = _invoke_sagemaker_chat(monkeypatch)
+
+    assert not any(name.lower() == _INFERENCE_COMPONENT_HEADER.lower() for name in client.request_headers)
+
+
+def test_hf_model_name_becomes_the_body_model(monkeypatch):
+    """`hf_model_name` names the served model, and containers that validate the body's `model`
+    404 on the endpoint name, so it has to replace it rather than ride along as an extra field."""
+    client = _invoke_sagemaker_chat(monkeypatch, hf_model_name="org/served-model")
+
+    assert client.request_body["model"] == "org/served-model"
+    assert "hf_model_name" not in client.request_body
+
+
+def test_body_model_stays_the_endpoint_name_when_hf_model_name_is_unset(monkeypatch):
+    """Without `hf_model_name` the body must keep the model it has today."""
+    client = _invoke_sagemaker_chat(monkeypatch)
+
+    assert client.request_body["model"] == "my-endpoint"
diff --git a/tests/test_litellm/llms/stability/image_generation/test_stability_image_generation.py b/tests/test_litellm/llms/stability/image_generation/test_stability_image_generation.py
index 6f1a04e78d3..c5b3c8fbdc5 100644
--- a/tests/test_litellm/llms/stability/image_generation/test_stability_image_generation.py
+++ b/tests/test_litellm/llms/stability/image_generation/test_stability_image_generation.py
@@ -83,7 +83,7 @@ class TestStabilityImageGenerationConfig:
         non_default_params = {"unsupported_param": "value"}
         optional_params = {}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match="Supported parameters are \\['n', 'size',") as exc_info:
             self.config.map_openai_params(
                 non_default_params=non_default_params,
                 optional_params=optional_params,
@@ -168,7 +168,7 @@ class TestStabilityImageGenerationConfig:
 
     def test_validate_environment_raises_without_api_key(self):
         """Test that validate_environment raises error without API key"""
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='STABILITY_API_KEY is not set\\. Please set it via') as exc_info:
             self.config.validate_environment(
                 headers={},
                 model="stability/sd3",
@@ -251,7 +251,7 @@ class TestStabilityImageGenerationConfig:
         model_response = ImageResponse(data=[])
         mock_logging = MagicMock()
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Content was filtered by Stability AI safety systems') as exc_info:
             self.config.transform_image_generation_response(
                 model="stability/sd3",
                 raw_response=mock_response,
diff --git a/tests/test_litellm/llms/tinyfish/test_tinyfish_search.py b/tests/test_litellm/llms/tinyfish/test_tinyfish_search.py
index 2dcccb8ea7e..69afbb416aa 100644
--- a/tests/test_litellm/llms/tinyfish/test_tinyfish_search.py
+++ b/tests/test_litellm/llms/tinyfish/test_tinyfish_search.py
@@ -697,7 +697,7 @@ class TestErrorHandling:
             }
         }
         mock_response = _make_mock_response(body, status_code=400)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='TinyFish Search: query is required\\. See https') as exc_info:
             config.transform_search_response(
                 raw_response=mock_response, logging_obj=None
             )
@@ -713,7 +713,7 @@ class TestErrorHandling:
         mock_response = _make_mock_response(
             body, status_code=429, headers={"Retry-After": "60"}
         )
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='TinyFish Search: rate limit exceeded\\. See https') as exc_info:
             config.transform_search_response(
                 raw_response=mock_response, logging_obj=None
             )
@@ -728,7 +728,7 @@ class TestErrorHandling:
         config = TinyfishSearchConfig()
         body = {"errors": [{"code": "10000", "message": "Internal"}]}
         mock_response = _make_mock_response(body, status_code=502)
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='TinyFish Search') as exc_info:
             config.transform_search_response(
                 raw_response=mock_response, logging_obj=None
             )
@@ -742,7 +742,7 @@ class TestErrorHandling:
         mock_response = _make_mock_response(
             json_data=None, status_code=502, text="<html>Bad Gateway</html>"
         )
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='TinyFish Search: <html>Bad Gateway<') as exc_info:
             config.transform_search_response(
                 raw_response=mock_response, logging_obj=None
             )
@@ -756,7 +756,7 @@ class TestErrorHandling:
         mock_response = _make_mock_response(
             json_data=None, status_code=200, text="not json"
         )
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='TinyFish Search: Expected JSON response, got: not json\\.') as exc_info:
             config.transform_search_response(
                 raw_response=mock_response, logging_obj=None
             )
@@ -785,7 +785,7 @@ class TestErrorHandling:
         # check TinyFish's schema, not their own input.
         config = TinyfishSearchConfig()
         mock_response = _make_mock_response({"query": "x"})  # no `results` key
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='validation error for SearchResponse') as exc_info:
             config.transform_search_response(
                 raw_response=mock_response, logging_obj=None
             )
diff --git a/tests/test_litellm/llms/vertex_ai/files/test_vertex_ai_files_integration.py b/tests/test_litellm/llms/vertex_ai/files/test_vertex_ai_files_integration.py
index 272565990bd..8f9acafa49d 100644
--- a/tests/test_litellm/llms/vertex_ai/files/test_vertex_ai_files_integration.py
+++ b/tests/test_litellm/llms/vertex_ai/files/test_vertex_ai_files_integration.py
@@ -159,7 +159,7 @@ class TestVertexAIFilesIntegration:
         # This test ensures the type annotations and error messages include vertex_ai
 
         # Test that calling with unsupported provider raises appropriate error
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="unsupported_provider' is not a valid LlmProviders") as exc_info:
             litellm.file_content(
                 file_id="test-file-id",
                 custom_llm_provider="unsupported_provider",  # This should fail
diff --git a/tests/test_litellm/llms/vertex_ai/test_vertex_ai_common_utils.py b/tests/test_litellm/llms/vertex_ai/test_vertex_ai_common_utils.py
index b83d4742b64..c189cdd0ea7 100644
--- a/tests/test_litellm/llms/vertex_ai/test_vertex_ai_common_utils.py
+++ b/tests/test_litellm/llms/vertex_ai/test_vertex_ai_common_utils.py
@@ -33,7 +33,7 @@ def test_validate_vertex_location_accepts_valid(location):
     ["attacker.example/", "evil.com#", "us.attacker.example", "us/../..", "US", "us_central1", "-us", "", None],
 )
 def test_validate_vertex_location_rejects_invalid(location):
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="vertex_location is required|Invalid vertex_location format"):
         validate_vertex_location(location)
 
 
diff --git a/tests/test_litellm/llms/volcengine/responses/test_volcengine_responses_transformation.py b/tests/test_litellm/llms/volcengine/responses/test_volcengine_responses_transformation.py
index 891d1c15c61..7922331d19f 100644
--- a/tests/test_litellm/llms/volcengine/responses/test_volcengine_responses_transformation.py
+++ b/tests/test_litellm/llms/volcengine/responses/test_volcengine_responses_transformation.py
@@ -137,7 +137,7 @@ class TestVolcengineResponsesAPITransformation:
         monkeypatch.delenv("ARK_API_KEY", raising=False)
         monkeypatch.delenv("VOLCENGINE_API_KEY", raising=False)
 
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='Volcengine API key is required\\. Set ARK_API_KEY /'):
             config.validate_environment(headers={}, model="volcengine/demo", litellm_params={})
 
     def test_unsupported_params_are_dropped_with_extra_body(self):
diff --git a/tests/test_litellm/llms/volcengine/test_volcengine_embedding.py b/tests/test_litellm/llms/volcengine/test_volcengine_embedding.py
index 07298f03f86..1670dac0e9d 100644
--- a/tests/test_litellm/llms/volcengine/test_volcengine_embedding.py
+++ b/tests/test_litellm/llms/volcengine/test_volcengine_embedding.py
@@ -202,7 +202,7 @@ def test_volcengine_embedding_error_scenarios():
                 k: v for k, v in scenario.items() if k != "expected_error_pattern"
             }
 
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match=f"(?i){scenario['expected_error_pattern']}") as exc_info:
                 litellm.embedding(input=["test"], **test_params)
 
             # Verify error message contains expected pattern
diff --git a/tests/test_litellm/llms/voyage/rerank/test_voyage_rerank_transformation.py b/tests/test_litellm/llms/voyage/rerank/test_voyage_rerank_transformation.py
index 8f99609e3f5..f466b7e19b5 100644
--- a/tests/test_litellm/llms/voyage/rerank/test_voyage_rerank_transformation.py
+++ b/tests/test_litellm/llms/voyage/rerank/test_voyage_rerank_transformation.py
@@ -227,7 +227,7 @@ class TestVoyageRerankTransform:
         mock_logging = MagicMock()
         model_response = RerankResponse()
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Unauthorized') as exc_info:
             self.config.transform_rerank_response(
                 model=self.model,
                 raw_response=mock_response,
@@ -248,7 +248,7 @@ class TestVoyageRerankTransform:
         mock_logging = MagicMock()
         model_response = RerankResponse()
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Failed to parse response: Invalid JSON response') as exc_info:
             self.config.transform_rerank_response(
                 model=self.model,
                 raw_response=mock_response,
diff --git a/tests/test_litellm/llms/voyage/test_voyage_multimodal_embedding.py b/tests/test_litellm/llms/voyage/test_voyage_multimodal_embedding.py
index f283e7fe0df..f3e6885cbe6 100644
--- a/tests/test_litellm/llms/voyage/test_voyage_multimodal_embedding.py
+++ b/tests/test_litellm/llms/voyage/test_voyage_multimodal_embedding.py
@@ -195,7 +195,7 @@ class TestVoyageMultimodalEmbeddings:
 
         monkeypatch.setattr(module, "get_secret_str", lambda name: None)
         config = VoyageMultimodalEmbeddingConfig()
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Voyage API key is required for multimodal embeddings\\. Set') as exc_info:
             config.validate_environment(
                 {}, "voyage-multimodal-3.5", [], {}, {}, api_key=None
             )
@@ -207,7 +207,7 @@ class TestVoyageMultimodalEmbeddings:
         )
 
         config = VoyageMultimodalEmbeddingConfig()
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Voyage multimodal embeddings require a non-empty') as exc_info:
             config._normalize_content_item({"type": "image_url", "image_url": {}})
         assert "image_url" in str(exc_info.value)
 
diff --git a/tests/test_litellm/llms/xai/test_xai_key_fallback.py b/tests/test_litellm/llms/xai/test_xai_key_fallback.py
index 4c769c572ac..ec3eb83309c 100644
--- a/tests/test_litellm/llms/xai/test_xai_key_fallback.py
+++ b/tests/test_litellm/llms/xai/test_xai_key_fallback.py
@@ -168,7 +168,7 @@ def test_responses_config_raises_when_no_key_is_available(monkeypatch):
     monkeypatch.setattr(litellm, "api_key", None)
     monkeypatch.delenv("XAI_API_KEY", raising=False)
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='XAI API key is required\\. Set api_key, litellm\\.xai_key') as exc_info:
         XAIResponsesAPIConfig().validate_environment({}, "xai/grok-3-mini", None)
 
     error_message = str(exc_info.value)
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 0209abee510..d5936b2ae86 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
@@ -8185,7 +8185,7 @@ class TestGetUserObjectPermission:
                 return_value=None,
             ),
         ):
-            with pytest.raises(ValueError):
+            with pytest.raises(ValueError, match="user 'human-dangling' names object_permission_id"):
                 await MCPRequestHandler._get_user_object_permission(auth)
 
     async def test_no_user_id_places_no_ceiling(self):
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 34852850de6..b4d3782ba43 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
@@ -2695,13 +2695,6 @@ async def test_token_endpoint_respects_x_forwarded_host():
             "443",
             "https://internal.local",
         ),
-        (
-            "http://localhost:4000/",
-            "https",
-            "proxy.example.com",
-            "8443",
-            "https://proxy.example.com:8443",
-        ),
         (
             "http://localhost:4000/",
             "https",
diff --git a/tests/test_litellm/proxy/_experimental/mcp_server/test_short_mcp_tool_prefix.py b/tests/test_litellm/proxy/_experimental/mcp_server/test_short_mcp_tool_prefix.py
index 6e3ac014840..941e5deee93 100644
--- a/tests/test_litellm/proxy/_experimental/mcp_server/test_short_mcp_tool_prefix.py
+++ b/tests/test_litellm/proxy/_experimental/mcp_server/test_short_mcp_tool_prefix.py
@@ -79,7 +79,7 @@ class TestShortPrefixHelpers:
         assert compute_short_server_prefix("abc") != compute_short_server_prefix("abd")
 
     def test_short_prefix_requires_server_id(self):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='compute_short_server_prefix requires a non-empty server_id'):
             compute_short_server_prefix("")
 
     def test_flag_defaults_to_false(self):
diff --git a/tests/test_litellm/proxy/auth/test_auth_checks.py b/tests/test_litellm/proxy/auth/test_auth_checks.py
index 6b40fa1b324..762d2cbf3c7 100644
--- a/tests/test_litellm/proxy/auth/test_auth_checks.py
+++ b/tests/test_litellm/proxy/auth/test_auth_checks.py
@@ -268,7 +268,7 @@ def test_get_experimental_ui_login_jwt_auth_token_invalid(
     invalid_sso_user_defined_values,
 ):
     """Test generating JWT token with missing user role"""
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='User role is required for experimental UI login') as exc_info:
         ExperimentalUIJWTToken.get_experimental_ui_login_jwt_auth_token(
             invalid_sso_user_defined_values
         )
@@ -883,7 +883,7 @@ async def test_get_user_object_wraps_db_outage_as_valueerror_preserving_context(
     mock_cache.async_set_cache = AsyncMock()
 
     with patch("litellm.proxy.auth.auth_checks._should_check_db", return_value=True):
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match="User doesn't exist in db\\.") as exc_info:
             await get_user_object(
                 user_id="outage-contract-probe-user",
                 prisma_client=mock_prisma_client,
diff --git a/tests/test_litellm/proxy/auth/test_auth_hot_path_network_requests.py b/tests/test_litellm/proxy/auth/test_auth_hot_path_network_requests.py
index 22752f767ce..6b2d2babedc 100644
--- a/tests/test_litellm/proxy/auth/test_auth_hot_path_network_requests.py
+++ b/tests/test_litellm/proxy/auth/test_auth_hot_path_network_requests.py
@@ -1,521 +1,521 @@
-"""
-Test to count and track the number of network requests (DB queries, cache lookups)
-made on the hot path for keys that have team_id and user_id attached.
-
-This test ensures we don't regress on the number of network requests made during
-request authentication, which directly impacts proxy latency.
-
-The hot path covers auth functions called on every LLM API request:
-- get_key_object: lookup the API key
-- get_team_object: lookup the team (for keys with team_id)
-- get_user_object: lookup the user (for keys with user_id)
-- get_team_membership: lookup team member budget (when team_member_spend set)
-
-Each function does: cache read -> (on miss) DB query -> cache write.
-We count these to catch regressions in the number of network requests.
-
-NOTE: This test does NOT require proxy extras (apscheduler, etc.) because
-it tests at the auth_checks level, not the full proxy_server level.
-"""
-
-import os
-import sys
-import time
-from typing import Any, Dict, List, Optional
-from unittest.mock import AsyncMock, MagicMock
-
-import pytest
-
-sys.path.insert(0, os.path.abspath("../../.."))
-
-from litellm.caching.dual_cache import DualCache
-from litellm.caching.in_memory_cache import InMemoryCache
-from litellm.proxy._types import (
-    LiteLLM_TeamTableCachedObj,
-    LiteLLM_UserTable,
-    LitellmUserRoles,
-    UserAPIKeyAuth,
-    LiteLLM_TeamMembership,
-    hash_token,
-)
-from litellm.proxy.auth.auth_checks import (
-    get_key_object,
-    get_team_membership,
-    get_team_object,
-    get_user_object,
-)
-
-
-class CacheCallTracker:
-    """
-    Tracks cache read/write operations by wrapping DualCache methods.
-    This is used to count network-level operations on the hot path.
-    """
-
-    def __init__(self):
-        self.cache_reads: List[Dict[str, Any]] = []
-        self.cache_writes: List[Dict[str, Any]] = []
-        self.db_queries: List[Dict[str, Any]] = []
-
-    def get_summary(self) -> Dict[str, Any]:
-        return {
-            "total_cache_reads": len(self.cache_reads),
-            "total_cache_writes": len(self.cache_writes),
-            "total_db_queries": len(self.db_queries),
-            "total_network_requests": len(self.cache_reads)
-            + len(self.cache_writes)
-            + len(self.db_queries),
-            "cache_read_keys": [r["key"] for r in self.cache_reads],
-            "cache_write_keys": [w["key"] for w in self.cache_writes],
-            "db_query_details": self.db_queries,
-        }
-
-
-def _wrap_cache_with_tracker(cache: DualCache, tracker: CacheCallTracker) -> DualCache:
-    """Wrap a DualCache to track all reads and writes."""
-    original_async_get = cache.async_get_cache
-    original_async_set = cache.async_set_cache
-
-    async def tracked_async_get(key, *args, **kwargs):
-        result = await original_async_get(key, *args, **kwargs)
-        tracker.cache_reads.append(
-            {"key": key, "hit": result is not None, "method": "async_get_cache"}
-        )
-        return result
-
-    async def tracked_async_set(key, value, *args, **kwargs):
-        tracker.cache_writes.append({"key": key, "method": "async_set_cache"})
-        return await original_async_set(key, value, *args, **kwargs)
-
-    cache.async_get_cache = tracked_async_get
-    cache.async_set_cache = tracked_async_set
-    return cache
-
-
-def _create_valid_token(
-    api_key: str,
-    team_id: str,
-    user_id: str,
-    has_team_member_spend: bool = False,
-    org_id: Optional[str] = None,
-) -> UserAPIKeyAuth:
-    """Create a UserAPIKeyAuth with team_id and user_id set."""
-    hashed = hash_token(api_key)
-    return UserAPIKeyAuth(
-        token=hashed,
-        api_key=api_key,
-        team_id=team_id,
-        user_id=user_id,
-        org_id=org_id,
-        models=["gpt-4", "gpt-3.5-turbo"],
-        max_budget=100.0,
-        spend=10.0,
-        team_spend=50.0,
-        team_max_budget=1000.0,
-        team_models=["gpt-4", "gpt-3.5-turbo"],
-        team_member_spend=5.0 if has_team_member_spend else None,
-        last_refreshed_at=time.time(),
-        user_role=LitellmUserRoles.INTERNAL_USER,
-    )
-
-
-def _create_team_object(team_id: str) -> LiteLLM_TeamTableCachedObj:
-    """Create a team table object for caching."""
-    return LiteLLM_TeamTableCachedObj(
-        team_id=team_id,
-        models=["gpt-4", "gpt-3.5-turbo"],
-        max_budget=1000.0,
-        spend=50.0,
-        tpm_limit=10000,
-        rpm_limit=100,
-        last_refreshed_at=time.time(),
-    )
-
-
-def _create_user_object(user_id: str) -> LiteLLM_UserTable:
-    """Create a user table object for caching."""
-    return LiteLLM_UserTable(
-        user_id=user_id,
-        max_budget=500.0,
-        spend=25.0,
-        models=["gpt-4"],
-        tpm_limit=5000,
-        rpm_limit=50,
-        user_role=LitellmUserRoles.INTERNAL_USER,
-        user_email="test@example.com",
-    )
-
-
-# ============================================================================
-# TEST: get_key_object cache behavior
-# ============================================================================
-
-
-@pytest.mark.asyncio
-async def test_get_key_object_warm_cache():
-    """
-    Test get_key_object with a warm cache - should hit cache, no DB query.
-    """
-    api_key = "sk-test-key-warm"
-    team_id = "team-123"
-    user_id = "user-456"
-    hashed_token = hash_token(api_key)
-
-    valid_token = _create_valid_token(api_key, team_id, user_id)
-
-    # Create cache with pre-populated data
-    cache = DualCache(in_memory_cache=InMemoryCache())
-    await cache.async_set_cache(key=hashed_token, value=valid_token)
-
-    # Track cache operations
-    tracker = CacheCallTracker()
-    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
-
-    # Mock prisma client (should NOT be called for warm cache)
-    mock_prisma = MagicMock()
-    mock_prisma.get_data = AsyncMock()
-
-    result = await get_key_object(
-        hashed_token=hashed_token,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    summary = tracker.get_summary()
-
-    # Should have exactly 1 cache read
-    assert summary["total_cache_reads"] == 1
-    assert hashed_token in summary["cache_read_keys"]
-
-    # Prisma should NOT have been called
-    mock_prisma.get_data.assert_not_called()
-
-    # Result should be the cached token
-    assert result.token == hashed_token
-
-
-@pytest.mark.asyncio
-async def test_get_key_object_cold_cache():
-    """
-    Test get_key_object with a cold cache - should miss cache, query DB.
-    """
-    api_key = "sk-test-key-cold"
-    team_id = "team-123"
-    user_id = "user-456"
-    hashed_token = hash_token(api_key)
-
-    valid_token = _create_valid_token(api_key, team_id, user_id)
-
-    # Create empty cache
-    cache = DualCache(in_memory_cache=InMemoryCache())
-
-    tracker = CacheCallTracker()
-    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
-
-    # Mock prisma client to return token on DB query
-    mock_prisma = MagicMock()
-    mock_prisma.get_data = AsyncMock(return_value=valid_token)
-
-    await get_key_object(
-        hashed_token=hashed_token,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    summary = tracker.get_summary()
-
-    # Should have 1 cache read (miss) and at least 1 cache write (populate cache)
-    assert summary["total_cache_reads"] >= 1
-
-    # Prisma SHOULD have been called
-    mock_prisma.get_data.assert_called_once()
-
-
-# ============================================================================
-# TEST: get_team_object cache behavior
-# ============================================================================
-
-
-@pytest.mark.asyncio
-async def test_get_team_object_warm_cache():
-    """
-    Test get_team_object with a warm cache - should hit cache, no DB query.
-    """
-    team_id = "team-warm-123"
-    team_obj = _create_team_object(team_id)
-
-    cache = DualCache(in_memory_cache=InMemoryCache())
-    cache_key = f"team_id:{team_id}"
-    await cache.async_set_cache(key=cache_key, value=team_obj)
-
-    tracker = CacheCallTracker()
-    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
-
-    mock_prisma = MagicMock()
-    mock_prisma.db = MagicMock()
-    mock_prisma.db.litellm_teamtable = MagicMock()
-    mock_prisma.db.litellm_teamtable.find_unique = AsyncMock()
-
-    await get_team_object(
-        team_id=team_id,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    summary = tracker.get_summary()
-
-    assert summary["total_cache_reads"] >= 1
-    assert cache_key in summary["cache_read_keys"]
-
-    # DB should NOT have been called
-    mock_prisma.db.litellm_teamtable.find_unique.assert_not_called()
-
-
-# ============================================================================
-# TEST: get_user_object cache behavior
-# ============================================================================
-
-
-@pytest.mark.asyncio
-async def test_get_user_object_warm_cache():
-    """
-    Test get_user_object with a warm cache - should hit cache, no DB query.
-    """
-    user_id = "user-warm-456"
-    user_obj = _create_user_object(user_id)
-
-    cache = DualCache(in_memory_cache=InMemoryCache())
-    await cache.async_set_cache(key=user_id, value=user_obj)
-
-    tracker = CacheCallTracker()
-    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
-
-    mock_prisma = MagicMock()
-    mock_prisma.db = MagicMock()
-    mock_prisma.db.litellm_usertable = MagicMock()
-    mock_prisma.db.litellm_usertable.find_unique = AsyncMock()
-
-    await get_user_object(
-        user_id=user_id,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-        user_id_upsert=False,
-    )
-
-    summary = tracker.get_summary()
-
-    assert summary["total_cache_reads"] >= 1
-    assert user_id in summary["cache_read_keys"]
-
-    # DB should NOT have been called
-    mock_prisma.db.litellm_usertable.find_unique.assert_not_called()
-
-
-# ============================================================================
-# TEST: get_team_membership cache behavior
-# ============================================================================
-
-
-@pytest.mark.asyncio
-async def test_get_team_membership_warm_cache():
-    """
-    Test get_team_membership with a warm cache - should hit cache, no DB query.
-    """
-    user_id = "user-tm-456"
-    team_id = "team-tm-123"
-
-    membership_dict = {
-        "user_id": user_id,
-        "team_id": team_id,
-        "spend": 3.0,
-        "budget_id": None,
-        "litellm_budget_table": None,
-    }
-
-    cache = DualCache(in_memory_cache=InMemoryCache())
-    # Cache key format used by get_team_membership
-    cache_key = f"team_membership:{user_id}:{team_id}"
-    await cache.async_set_cache(key=cache_key, value=membership_dict)
-
-    tracker = CacheCallTracker()
-    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
-
-    mock_prisma = MagicMock()
-    mock_prisma.db = MagicMock()
-    mock_prisma.db.litellm_teammembership = MagicMock()
-    mock_prisma.db.litellm_teammembership.find_unique = AsyncMock()
-
-    await get_team_membership(
-        user_id=user_id,
-        team_id=team_id,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    summary = tracker.get_summary()
-
-    assert summary["total_cache_reads"] >= 1
-    assert cache_key in summary["cache_read_keys"]
-
-    # DB should NOT have been called
-    mock_prisma.db.litellm_teammembership.find_unique.assert_not_called()
-
-
-# ============================================================================
-# TEST: Document duplicate team membership cache key issue
-# ============================================================================
-
-
-@pytest.mark.asyncio
-async def test_team_membership_cache_key_duplication():
-    """
-    Document the team membership duplicate cache key issue:
-
-    Team membership is queried via TWO different cache keys:
-    1. "{team_id}_{user_id}" - used in user_api_key_auth.py:1048
-    2. "team_membership:{user_id}:{team_id}" - used in auth_checks.py:960 (get_team_membership)
-
-    This test documents that both keys refer to the same data but use different
-    cache key formats, potentially leading to duplicate lookups.
-    """
-    user_id = "user-dup-456"
-    team_id = "team-dup-123"
-
-    # The two different cache keys used for the same data
-    key_format_1 = f"{team_id}_{user_id}"  # user_api_key_auth format
-    key_format_2 = f"team_membership:{user_id}:{team_id}"  # auth_checks format
-
-    _ = {
-        "user_id": user_id,
-        "team_id": team_id,
-        "spend": 3.0,
-    }
-
-    # Document that these are different keys
-    assert (
-        key_format_1 != key_format_2
-    ), "Cache keys should be different (this is the bug)"
-
-    # Document that these are different keys
-    assert (
-        key_format_1 != key_format_2
-    ), "Cache keys should be different (this is the bug)"
-
-
-# ============================================================================
-# TEST: Full hot path network count summary
-# ============================================================================
-
-
-@pytest.mark.asyncio
-async def test_full_hot_path_network_count():
-    """
-    Summary test that counts all network operations when processing
-    a request with a key that has team_id and user_id attached.
-
-    This test verifies the baseline number of cache operations expected
-    on a fully warm cache path.
-    """
-    api_key = "sk-test-full-path"
-    team_id = "team-full-123"
-    user_id = "user-full-456"
-    hashed_token = hash_token(api_key)
-
-    # Create all objects
-    valid_token = _create_valid_token(
-        api_key, team_id, user_id, has_team_member_spend=True
-    )
-    team_obj = _create_team_object(team_id)
-    user_obj = _create_user_object(user_id)
-    membership_data = LiteLLM_TeamMembership(
-        user_id=user_id,
-        team_id=team_id,
-        spend=3.0,
-        budget_id=None,
-        litellm_budget_table=None,
-    )
-
-    # Pre-populate cache with all data
-    cache = DualCache(in_memory_cache=InMemoryCache())
-    await cache.async_set_cache(key=hashed_token, value=valid_token)
-    await cache.async_set_cache(key=f"team_id:{team_id}", value=team_obj)
-    await cache.async_set_cache(key=user_id, value=user_obj)
-    await cache.async_set_cache(
-        key=f"team_membership:{user_id}:{team_id}", value=membership_data.model_dump()
-    )
-    await cache.async_set_cache(
-        key=f"{team_id}_{user_id}", value=membership_data.model_dump()
-    )
-
-    # Create tracker AFTER populating cache
-    tracker = CacheCallTracker()
-    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
-
-    # Mock prisma (should not be called on warm cache)
-    mock_prisma = MagicMock()
-
-    # Call each function to simulate the hot path
-    await get_key_object(
-        hashed_token=hashed_token,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    await get_team_object(
-        team_id=team_id,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    await get_user_object(
-        user_id=user_id,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-        user_id_upsert=False,
-    )
-
-    await get_team_membership(
-        user_id=user_id,
-        team_id=team_id,
-        prisma_client=mock_prisma,
-        user_api_key_cache=tracked_cache,
-        parent_otel_span=None,
-        proxy_logging_obj=None,
-    )
-
-    summary = tracker.get_summary()
-
-    # Assertions for expected baseline
-    # On warm cache: 4 reads (key, team, user, team_membership)
-    assert (
-        summary["total_cache_reads"] == 4
-    ), f"Expected 4 cache reads on warm path, got {summary['total_cache_reads']}"
-
-    # No DB queries on warm cache
-    assert (
-        summary["total_db_queries"] == 0
-    ), f"Expected 0 DB queries on warm path, got {summary['total_db_queries']}"
-
-    # Total network requests should be exactly 4 on warm cache
-    assert (
-        summary["total_network_requests"] == 4
-    ), f"Expected 4 total network requests on warm path, got {summary['total_network_requests']}"
+"""
+Test to count and track the number of network requests (DB queries, cache lookups)
+made on the hot path for keys that have team_id and user_id attached.
+
+This test ensures we don't regress on the number of network requests made during
+request authentication, which directly impacts proxy latency.
+
+The hot path covers auth functions called on every LLM API request:
+- get_key_object: lookup the API key
+- get_team_object: lookup the team (for keys with team_id)
+- get_user_object: lookup the user (for keys with user_id)
+- get_team_membership: lookup team member budget (when team_member_spend set)
+
+Each function does: cache read -> (on miss) DB query -> cache write.
+We count these to catch regressions in the number of network requests.
+
+NOTE: This test does NOT require proxy extras (apscheduler, etc.) because
+it tests at the auth_checks level, not the full proxy_server level.
+"""
+
+import os
+import sys
+import time
+from typing import Any, Dict, List, Optional
+from unittest.mock import AsyncMock, MagicMock
+
+import pytest
+
+sys.path.insert(0, os.path.abspath("../../.."))
+
+from litellm.caching.dual_cache import DualCache
+from litellm.caching.in_memory_cache import InMemoryCache
+from litellm.proxy._types import (
+    LiteLLM_TeamTableCachedObj,
+    LiteLLM_UserTable,
+    LitellmUserRoles,
+    UserAPIKeyAuth,
+    LiteLLM_TeamMembership,
+    hash_token,
+)
+from litellm.proxy.auth.auth_checks import (
+    get_key_object,
+    get_team_membership,
+    get_team_object,
+    get_user_object,
+)
+
+
+class CacheCallTracker:
+    """
+    Tracks cache read/write operations by wrapping DualCache methods.
+    This is used to count network-level operations on the hot path.
+    """
+
+    def __init__(self):
+        self.cache_reads: List[Dict[str, Any]] = []
+        self.cache_writes: List[Dict[str, Any]] = []
+        self.db_queries: List[Dict[str, Any]] = []
+
+    def get_summary(self) -> Dict[str, Any]:
+        return {
+            "total_cache_reads": len(self.cache_reads),
+            "total_cache_writes": len(self.cache_writes),
+            "total_db_queries": len(self.db_queries),
+            "total_network_requests": len(self.cache_reads)
+            + len(self.cache_writes)
+            + len(self.db_queries),
+            "cache_read_keys": [r["key"] for r in self.cache_reads],
+            "cache_write_keys": [w["key"] for w in self.cache_writes],
+            "db_query_details": self.db_queries,
+        }
+
+
+def _wrap_cache_with_tracker(cache: DualCache, tracker: CacheCallTracker) -> DualCache:
+    """Wrap a DualCache to track all reads and writes."""
+    original_async_get = cache.async_get_cache
+    original_async_set = cache.async_set_cache
+
+    async def tracked_async_get(key, *args, **kwargs):
+        result = await original_async_get(key, *args, **kwargs)
+        tracker.cache_reads.append(
+            {"key": key, "hit": result is not None, "method": "async_get_cache"}
+        )
+        return result
+
+    async def tracked_async_set(key, value, *args, **kwargs):
+        tracker.cache_writes.append({"key": key, "method": "async_set_cache"})
+        return await original_async_set(key, value, *args, **kwargs)
+
+    cache.async_get_cache = tracked_async_get
+    cache.async_set_cache = tracked_async_set
+    return cache
+
+
+def _create_valid_token(
+    api_key: str,
+    team_id: str,
+    user_id: str,
+    has_team_member_spend: bool = False,
+    org_id: Optional[str] = None,
+) -> UserAPIKeyAuth:
+    """Create a UserAPIKeyAuth with team_id and user_id set."""
+    hashed = hash_token(api_key)
+    return UserAPIKeyAuth(
+        token=hashed,
+        api_key=api_key,
+        team_id=team_id,
+        user_id=user_id,
+        org_id=org_id,
+        models=["gpt-4", "gpt-3.5-turbo"],
+        max_budget=100.0,
+        spend=10.0,
+        team_spend=50.0,
+        team_max_budget=1000.0,
+        team_models=["gpt-4", "gpt-3.5-turbo"],
+        team_member_spend=5.0 if has_team_member_spend else None,
+        last_refreshed_at=time.time(),
+        user_role=LitellmUserRoles.INTERNAL_USER,
+    )
+
+
+def _create_team_object(team_id: str) -> LiteLLM_TeamTableCachedObj:
+    """Create a team table object for caching."""
+    return LiteLLM_TeamTableCachedObj(
+        team_id=team_id,
+        models=["gpt-4", "gpt-3.5-turbo"],
+        max_budget=1000.0,
+        spend=50.0,
+        tpm_limit=10000,
+        rpm_limit=100,
+        last_refreshed_at=time.time(),
+    )
+
+
+def _create_user_object(user_id: str) -> LiteLLM_UserTable:
+    """Create a user table object for caching."""
+    return LiteLLM_UserTable(
+        user_id=user_id,
+        max_budget=500.0,
+        spend=25.0,
+        models=["gpt-4"],
+        tpm_limit=5000,
+        rpm_limit=50,
+        user_role=LitellmUserRoles.INTERNAL_USER,
+        user_email="test@example.com",
+    )
+
+
+# ============================================================================
+# TEST: get_key_object cache behavior
+# ============================================================================
+
+
+@pytest.mark.asyncio
+async def test_get_key_object_warm_cache():
+    """
+    Test get_key_object with a warm cache - should hit cache, no DB query.
+    """
+    api_key = "sk-test-key-warm"
+    team_id = "team-123"
+    user_id = "user-456"
+    hashed_token = hash_token(api_key)
+
+    valid_token = _create_valid_token(api_key, team_id, user_id)
+
+    # Create cache with pre-populated data
+    cache = DualCache(in_memory_cache=InMemoryCache())
+    await cache.async_set_cache(key=hashed_token, value=valid_token)
+
+    # Track cache operations
+    tracker = CacheCallTracker()
+    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
+
+    # Mock prisma client (should NOT be called for warm cache)
+    mock_prisma = MagicMock()
+    mock_prisma.get_data = AsyncMock()
+
+    result = await get_key_object(
+        hashed_token=hashed_token,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    summary = tracker.get_summary()
+
+    # Should have exactly 1 cache read
+    assert summary["total_cache_reads"] == 1
+    assert hashed_token in summary["cache_read_keys"]
+
+    # Prisma should NOT have been called
+    mock_prisma.get_data.assert_not_called()
+
+    # Result should be the cached token
+    assert result.token == hashed_token
+
+
+@pytest.mark.asyncio
+async def test_get_key_object_cold_cache():
+    """
+    Test get_key_object with a cold cache - should miss cache, query DB.
+    """
+    api_key = "sk-test-key-cold"
+    team_id = "team-123"
+    user_id = "user-456"
+    hashed_token = hash_token(api_key)
+
+    valid_token = _create_valid_token(api_key, team_id, user_id)
+
+    # Create empty cache
+    cache = DualCache(in_memory_cache=InMemoryCache())
+
+    tracker = CacheCallTracker()
+    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
+
+    # Mock prisma client to return token on DB query
+    mock_prisma = MagicMock()
+    mock_prisma.get_data = AsyncMock(return_value=valid_token)
+
+    await get_key_object(
+        hashed_token=hashed_token,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    summary = tracker.get_summary()
+
+    # Should have 1 cache read (miss) and at least 1 cache write (populate cache)
+    assert summary["total_cache_reads"] >= 1
+
+    # Prisma SHOULD have been called
+    mock_prisma.get_data.assert_called_once()
+
+
+# ============================================================================
+# TEST: get_team_object cache behavior
+# ============================================================================
+
+
+@pytest.mark.asyncio
+async def test_get_team_object_warm_cache():
+    """
+    Test get_team_object with a warm cache - should hit cache, no DB query.
+    """
+    team_id = "team-warm-123"
+    team_obj = _create_team_object(team_id)
+
+    cache = DualCache(in_memory_cache=InMemoryCache())
+    cache_key = f"team_id:{team_id}"
+    await cache.async_set_cache(key=cache_key, value=team_obj)
+
+    tracker = CacheCallTracker()
+    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
+
+    mock_prisma = MagicMock()
+    mock_prisma.db = MagicMock()
+    mock_prisma.db.litellm_teamtable = MagicMock()
+    mock_prisma.db.litellm_teamtable.find_unique = AsyncMock()
+
+    await get_team_object(
+        team_id=team_id,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    summary = tracker.get_summary()
+
+    assert summary["total_cache_reads"] >= 1
+    assert cache_key in summary["cache_read_keys"]
+
+    # DB should NOT have been called
+    mock_prisma.db.litellm_teamtable.find_unique.assert_not_called()
+
+
+# ============================================================================
+# TEST: get_user_object cache behavior
+# ============================================================================
+
+
+@pytest.mark.asyncio
+async def test_get_user_object_warm_cache():
+    """
+    Test get_user_object with a warm cache - should hit cache, no DB query.
+    """
+    user_id = "user-warm-456"
+    user_obj = _create_user_object(user_id)
+
+    cache = DualCache(in_memory_cache=InMemoryCache())
+    await cache.async_set_cache(key=user_id, value=user_obj)
+
+    tracker = CacheCallTracker()
+    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
+
+    mock_prisma = MagicMock()
+    mock_prisma.db = MagicMock()
+    mock_prisma.db.litellm_usertable = MagicMock()
+    mock_prisma.db.litellm_usertable.find_unique = AsyncMock()
+
+    await get_user_object(
+        user_id=user_id,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+        user_id_upsert=False,
+    )
+
+    summary = tracker.get_summary()
+
+    assert summary["total_cache_reads"] >= 1
+    assert user_id in summary["cache_read_keys"]
+
+    # DB should NOT have been called
+    mock_prisma.db.litellm_usertable.find_unique.assert_not_called()
+
+
+# ============================================================================
+# TEST: get_team_membership cache behavior
+# ============================================================================
+
+
+@pytest.mark.asyncio
+async def test_get_team_membership_warm_cache():
+    """
+    Test get_team_membership with a warm cache - should hit cache, no DB query.
+    """
+    user_id = "user-tm-456"
+    team_id = "team-tm-123"
+
+    membership_dict = {
+        "user_id": user_id,
+        "team_id": team_id,
+        "spend": 3.0,
+        "budget_id": None,
+        "litellm_budget_table": None,
+    }
+
+    cache = DualCache(in_memory_cache=InMemoryCache())
+    # Cache key format used by get_team_membership
+    cache_key = f"team_membership:{user_id}:{team_id}"
+    await cache.async_set_cache(key=cache_key, value=membership_dict)
+
+    tracker = CacheCallTracker()
+    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
+
+    mock_prisma = MagicMock()
+    mock_prisma.db = MagicMock()
+    mock_prisma.db.litellm_teammembership = MagicMock()
+    mock_prisma.db.litellm_teammembership.find_unique = AsyncMock()
+
+    await get_team_membership(
+        user_id=user_id,
+        team_id=team_id,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    summary = tracker.get_summary()
+
+    assert summary["total_cache_reads"] >= 1
+    assert cache_key in summary["cache_read_keys"]
+
+    # DB should NOT have been called
+    mock_prisma.db.litellm_teammembership.find_unique.assert_not_called()
+
+
+# ============================================================================
+# TEST: Document duplicate team membership cache key issue
+# ============================================================================
+
+
+@pytest.mark.asyncio
+async def test_team_membership_cache_key_duplication():
+    """
+    Document the team membership duplicate cache key issue:
+
+    Team membership is queried via TWO different cache keys:
+    1. "{team_id}_{user_id}" - used in user_api_key_auth.py:1048
+    2. "team_membership:{user_id}:{team_id}" - used in auth_checks.py:960 (get_team_membership)
+
+    This test documents that both keys refer to the same data but use different
+    cache key formats, potentially leading to duplicate lookups.
+    """
+    user_id = "user-dup-456"
+    team_id = "team-dup-123"
+
+    # The two different cache keys used for the same data
+    key_format_1 = f"{team_id}_{user_id}"  # user_api_key_auth format
+    key_format_2 = f"team_membership:{user_id}:{team_id}"  # auth_checks format
+
+    _ = {
+        "user_id": user_id,
+        "team_id": team_id,
+        "spend": 3.0,
+    }
+
+    # Document that these are different keys
+    assert (
+        key_format_1 != key_format_2
+    ), "Cache keys should be different (this is the bug)"
+
+    # Document that these are different keys
+    assert (
+        key_format_1 != key_format_2
+    ), "Cache keys should be different (this is the bug)"
+
+
+# ============================================================================
+# TEST: Full hot path network count summary
+# ============================================================================
+
+
+@pytest.mark.asyncio
+async def test_full_hot_path_network_count():
+    """
+    Summary test that counts all network operations when processing
+    a request with a key that has team_id and user_id attached.
+
+    This test verifies the baseline number of cache operations expected
+    on a fully warm cache path.
+    """
+    api_key = "sk-test-full-path"
+    team_id = "team-full-123"
+    user_id = "user-full-456"
+    hashed_token = hash_token(api_key)
+
+    # Create all objects
+    valid_token = _create_valid_token(
+        api_key, team_id, user_id, has_team_member_spend=True
+    )
+    team_obj = _create_team_object(team_id)
+    user_obj = _create_user_object(user_id)
+    membership_data = LiteLLM_TeamMembership(
+        user_id=user_id,
+        team_id=team_id,
+        spend=3.0,
+        budget_id=None,
+        litellm_budget_table=None,
+    )
+
+    # Pre-populate cache with all data
+    cache = DualCache(in_memory_cache=InMemoryCache())
+    await cache.async_set_cache(key=hashed_token, value=valid_token)
+    await cache.async_set_cache(key=f"team_id:{team_id}", value=team_obj)
+    await cache.async_set_cache(key=user_id, value=user_obj)
+    await cache.async_set_cache(
+        key=f"team_membership:{user_id}:{team_id}", value=membership_data.model_dump()
+    )
+    await cache.async_set_cache(
+        key=f"{team_id}_{user_id}", value=membership_data.model_dump()
+    )
+
+    # Create tracker AFTER populating cache
+    tracker = CacheCallTracker()
+    tracked_cache = _wrap_cache_with_tracker(cache, tracker)
+
+    # Mock prisma (should not be called on warm cache)
+    mock_prisma = MagicMock()
+
+    # Call each function to simulate the hot path
+    await get_key_object(
+        hashed_token=hashed_token,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    await get_team_object(
+        team_id=team_id,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    await get_user_object(
+        user_id=user_id,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+        user_id_upsert=False,
+    )
+
+    await get_team_membership(
+        user_id=user_id,
+        team_id=team_id,
+        prisma_client=mock_prisma,
+        user_api_key_cache=tracked_cache,
+        parent_otel_span=None,
+        proxy_logging_obj=None,
+    )
+
+    summary = tracker.get_summary()
+
+    # Assertions for expected baseline
+    # On warm cache: 4 reads (key, team, user, team_membership)
+    assert (
+        summary["total_cache_reads"] == 4
+    ), f"Expected 4 cache reads on warm path, got {summary['total_cache_reads']}"
+
+    # No DB queries on warm cache
+    assert (
+        summary["total_db_queries"] == 0
+    ), f"Expected 0 DB queries on warm path, got {summary['total_db_queries']}"
+
+    # Total network requests should be exactly 4 on warm cache
+    assert (
+        summary["total_network_requests"] == 4
+    ), f"Expected 4 total network requests on warm path, got {summary['total_network_requests']}"
 
 
 # ============================================================================
@@ -540,7 +540,7 @@ async def test_get_user_object_missing_user_negative_cache():
     mock_prisma.db.litellm_usertable.find_unique = AsyncMock(return_value=None)
 
     for _ in range(3):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="User doesn't exist in db\\."):
             await get_user_object(
                 user_id=user_id,
                 prisma_client=mock_prisma,
@@ -570,7 +570,7 @@ async def test_get_user_object_missing_user_rechecks_after_expiry():
     mock_prisma.db.litellm_usertable = MagicMock()
     mock_prisma.db.litellm_usertable.find_unique = AsyncMock(return_value=None)
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="User doesn't exist in db\\."):
         await get_user_object(
             user_id=user_id,
             prisma_client=mock_prisma,
@@ -586,7 +586,7 @@ async def test_get_user_object_missing_user_rechecks_after_expiry():
         time.time() - (db_cache_expiry + 1),
     )
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="User doesn't exist in db\\."):
         await get_user_object(
             user_id=user_id,
             prisma_client=mock_prisma,
diff --git a/tests/test_litellm/proxy/auth/test_auth_utils.py b/tests/test_litellm/proxy/auth/test_auth_utils.py
index ecf7f89d487..9301176f3ed 100644
--- a/tests/test_litellm/proxy/auth/test_auth_utils.py
+++ b/tests/test_litellm/proxy/auth/test_auth_utils.py
@@ -1588,7 +1588,7 @@ class TestCheckCompleteCredentialsBlocksSSRF:
             "litellm.proxy.auth.auth_utils.validate_url",
             side_effect=SSRFError(f"blocked: {blocked_url}"),
         ):
-            with pytest.raises(ValueError) as exc_info:
+            with pytest.raises(ValueError, match='is rejected by the SSRF guard') as exc_info:
                 check_complete_credentials(
                     {
                         "model": "gpt-4",
@@ -2144,7 +2144,7 @@ class TestIsRequestBodySafeBlocksEndpointTargetingFields:
         ],
     )
     def test_endpoint_targeting_field_in_request_body_is_rejected(self, field):
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request') as exc:
             is_request_body_safe(
                 request_body={"model": "gpt-4", field: "https://attacker.example"},
                 general_settings={},
@@ -2165,7 +2165,7 @@ class TestIsRequestBodySafeBlocksEndpointTargetingFields:
         # on the blocklist into an SSRF / credential-exfil hole. Verify
         # that supplying an api_key (alongside the banned param) does NOT
         # bypass the gate — it can only be opened by an admin opt-in.
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request') as exc:
             is_request_body_safe(
                 request_body={
                     "model": "gpt-4",
@@ -2722,7 +2722,7 @@ class TestObservabilityCallbackBans:
         ],
     )
     def test_observability_field_in_request_body_root_is_rejected(self, field):
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request') as exc:
             is_request_body_safe(
                 request_body={"model": "gpt-4", field: "attacker-value"},
                 general_settings={},
@@ -2752,7 +2752,7 @@ class TestObservabilityCallbackBans:
         # Verifies the metadata walk: a value smuggled inside ``metadata``
         # or ``litellm_metadata`` is just as dangerous as the same field
         # at the body root, and must hit the same gate.
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request') as exc:
             is_request_body_safe(
                 request_body={
                     "model": "gpt-4",
@@ -2787,7 +2787,7 @@ class TestObservabilityCallbackBans:
         )
 
     def test_observability_field_in_litellm_params_metadata_is_rejected(self):
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request: turn_off_message_logging is not allowed') as exc:
             is_request_body_safe(
                 request_body={
                     "model": "gpt-4",
@@ -2814,7 +2814,7 @@ class TestObservabilityCallbackBans:
         # the ``isinstance(dict)`` guard.
         import json
 
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request: langfuse_host is not allowed in request') as exc:
             is_request_body_safe(
                 request_body={
                     "model": "gpt-4",
@@ -2887,7 +2887,7 @@ def test_model_level_allow_does_not_skip_subsequent_banned_params(monkeypatch):
         lambda model, param, request_body_value, llm_router: param == "api_base",
     )
 
-    with pytest.raises(ValueError) as exc:
+    with pytest.raises(ValueError, match='Rejected Request: langfuse_host is not allowed in request') as exc:
         is_request_body_safe(
             request_body={
                 "model": "gpt-4",
@@ -2958,7 +2958,7 @@ class TestPricingInjectionBlocked:
         ],
     )
     def test_pricing_field_rejected_by_default(self, field, value):
-        with pytest.raises(ValueError) as exc:
+        with pytest.raises(ValueError, match='Rejected Request') as exc:
             is_request_body_safe(
                 request_body={"model": "gpt-4", field: value},
                 general_settings={},
diff --git a/tests/test_litellm/proxy/auth/test_handle_jwt.py b/tests/test_litellm/proxy/auth/test_handle_jwt.py
index a9e12beb54b..99a0a4c0a8b 100644
--- a/tests/test_litellm/proxy/auth/test_handle_jwt.py
+++ b/tests/test_litellm/proxy/auth/test_handle_jwt.py
@@ -2589,7 +2589,7 @@ async def test_find_and_validate_raises_when_required_team_not_found():
     # Token without team info
     jwt_token = {"sub": "user-1"}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="No team found in token\\. Checked team_id field 'None' and") as exc_info:
         await JWTAuthManager.find_and_validate_specific_team_id(
             jwt_handler=jwt_handler,
             jwt_valid_token=jwt_token,
@@ -2916,7 +2916,7 @@ async def test_find_and_validate_specific_team_id_hints_bracket_notation():
     # token has roles as a list — dot-notation won't find anything
     token = {"roles": ["team1"]}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="is not supported\\. Use 'roles' instead — LiteLLM") as exc_info:
         await JWTAuthManager.find_and_validate_specific_team_id(
             jwt_handler=handler,
             jwt_valid_token=token,
@@ -2947,7 +2947,7 @@ async def test_find_and_validate_specific_team_id_hints_bracket_index_notation()
     handler = _make_jwt_handler("roles[0]")
     token = {"roles": ["team1"]}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="is not supported in team_id_jwt_field\\. Use 'roles' instead") as exc_info:
         await JWTAuthManager.find_and_validate_specific_team_id(
             jwt_handler=handler,
             jwt_valid_token=token,
@@ -2977,7 +2977,7 @@ async def test_find_and_validate_specific_team_id_no_hint_for_valid_field():
     handler = _make_jwt_handler("appid")
     token = {}  # no appid — triggers the "no team found" path
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="No team found in token\\. Checked team_id field 'appid' and") as exc_info:
         await JWTAuthManager.find_and_validate_specific_team_id(
             jwt_handler=handler,
             jwt_valid_token=token,
@@ -4807,7 +4807,7 @@ async def test_multi_issuer_jwt_unknown_issuer_falls_back_to_global_jwks(monkeyp
         kid="issuer-key",
     )
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='Missing JWT Public Key URL from environment\\.') as exc:
         await jwt_handler.auth_jwt(token=token)
 
     assert "Missing JWT Public Key URL from environment." in str(exc.value)
@@ -4838,7 +4838,7 @@ async def test_multi_issuer_jwt_rejects_wrong_audience(monkeypatch):
         kid="issuer-key",
     )
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match="Validation fails: Audience doesn't match") as exc:
         await jwt_handler.auth_jwt(token=token)
 
     assert "Validation fails" in str(exc.value)
@@ -4881,7 +4881,7 @@ async def test_multi_issuer_jwt_same_kid_does_not_cross_issuer_keys(monkeypatch)
         kid=shared_kid,
     )
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='Validation fails: Signature verification failed') as exc:
         await jwt_handler.auth_jwt(token=token)
 
     assert "Validation fails" in str(exc.value)
@@ -4936,7 +4936,7 @@ def test_multi_issuer_jwt_requires_audience_unless_explicitly_disabled(
     issuer = "https://issuer.example.com"
     jwks_url = f"{issuer}/keys"
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='must configure audience or set') as exc:
         LiteLLM_JWTAuth(
             issuers=[
                 {
@@ -4953,7 +4953,7 @@ def test_multi_issuer_jwt_rejects_audience_with_disable_audience_validation():
     issuer = "https://issuer.example.com"
     jwks_url = f"{issuer}/keys"
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='cannot set audience and disable_audience_validation=True') as exc:
         LiteLLM_JWTAuth(
             issuers=[
                 {
diff --git a/tests/test_litellm/proxy/auth/test_oauth2_proxy_hook.py b/tests/test_litellm/proxy/auth/test_oauth2_proxy_hook.py
index dcbfd281e01..2d81d48de1e 100644
--- a/tests/test_litellm/proxy/auth/test_oauth2_proxy_hook.py
+++ b/tests/test_litellm/proxy/auth/test_oauth2_proxy_hook.py
@@ -141,7 +141,7 @@ async def test_refuses_to_map_non_identity_fields(configure_proxy, privileged_fi
     configure_proxy(mappings={privileged_field: f"x-{privileged_field}"})
     request = _request_with_headers({f"x-{privileged_field}": "proxy_admin"})
 
-    with pytest.raises(ValueError) as exc:
+    with pytest.raises(ValueError, match='proxy auth refuses to map non-identity UserAPIKeyAuth') as exc:
         await handle_oauth2_proxy_request(request)
     assert privileged_field in str(exc.value)
 
diff --git a/tests/test_litellm/proxy/auth/test_route_checks.py b/tests/test_litellm/proxy/auth/test_route_checks.py
index 6d6e20e9c36..636c5480d67 100644
--- a/tests/test_litellm/proxy/auth/test_route_checks.py
+++ b/tests/test_litellm/proxy/auth/test_route_checks.py
@@ -42,7 +42,7 @@ def test_non_admin_config_update_route_rejected():
     request.query_params = {}
 
     # Test that calling /config/update route raises HTTPException with 403 status
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER.value,
@@ -134,7 +134,7 @@ def test_user_banner_update_rejected_for_non_admin():
     request = MagicMock(spec=Request)
     request.query_params = {}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER.value,
@@ -1814,7 +1814,7 @@ def test_internal_user_blocked_from_global_spend_routes(route):
     request = MagicMock(spec=Request)
     request.query_params = {}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER.value,
@@ -1843,7 +1843,7 @@ def test_internal_user_view_only_blocked_from_global_spend_routes(route):
     request = MagicMock(spec=Request)
     request.query_params = {}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER_VIEW_ONLY.value,
@@ -2046,7 +2046,7 @@ def test_internal_user_blocked_from_admin_viewer_logs_routes(route):
     if route not in INTERNAL_USER_BLOCKED_SUBSET:
         return
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER.value,
@@ -2530,7 +2530,7 @@ def test_non_admin_non_team_admin_cannot_access_config_update_but_can_attempt_re
     )
 
     # /config/update is still blocked
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER.value,
@@ -3188,7 +3188,7 @@ def test_internal_user_blocked_from_search_tool_writes(route):
     request = MagicMock(spec=Request)
     request.query_params = {}
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Only proxy admin can be used to generate, delete, update') as exc_info:
         RouteChecks.non_proxy_admin_allowed_routes_check(
             user_obj=user_obj,
             _user_role=LitellmUserRoles.INTERNAL_USER.value,
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 ab7e3d9701c..043bbb5b76a 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
@@ -5337,7 +5337,7 @@ async def test_random_non_sk_token_is_rejected(monkeypatch):
         patch("litellm.proxy.proxy_server.master_key", "sk-master"),
         patch("litellm.proxy.proxy_server.prisma_client", MagicMock()),
     ):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='LiteLLM Virtual Key expected\\.') as exc_info:
             await user_api_key_auth(
                 request=mock_request,
                 api_key="Bearer not-a-real-token",
@@ -5539,7 +5539,7 @@ async def test_real_jwt_still_requires_license_when_jwt_auth_enabled(monkeypatch
         patch("litellm.proxy.proxy_server.master_key", "sk-master"),
         patch("litellm.proxy.proxy_server.prisma_client", None),
     ):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='JWT Auth is an enterprise only feature\\. You must be a') as exc_info:
             await user_api_key_auth(
                 request=mock_request,
                 api_key=f"Bearer {jwt_token}",
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 eb40f54a1f3..be29269fe25 100644
--- a/tests/test_litellm/proxy/client/cli/test_auth_commands.py
+++ b/tests/test_litellm/proxy/client/cli/test_auth_commands.py
@@ -84,7 +84,7 @@ class TestPollingErrorSurfacing:
         }
 
         with patch("requests.get", return_value=mock_response) as mock_get, patch("time.sleep"):
-            with pytest.raises(ValueError) 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) 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) 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) 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) 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)
diff --git a/tests/test_litellm/proxy/client/cli/test_pkce_login.py b/tests/test_litellm/proxy/client/cli/test_pkce_login.py
index 70f481d5cfa..f58bd0ff412 100644
--- a/tests/test_litellm/proxy/client/cli/test_pkce_login.py
+++ b/tests/test_litellm/proxy/client/cli/test_pkce_login.py
@@ -622,7 +622,7 @@ def test_fresh_api_key_never_hands_out_a_rotated_key_it_could_not_save():
     def save(_record):
         raise OSError("disk full")
 
-    with pytest.raises(OSError):
+    with pytest.raises(OSError, match="disk full"):
         _fresh(STORED, save, http, now=lambda: 999_950.0)
 
 
diff --git a/tests/test_litellm/proxy/client/test_models.py b/tests/test_litellm/proxy/client/test_models.py
index b2485032a37..33f963b74af 100644
--- a/tests/test_litellm/proxy/client/test_models.py
+++ b/tests/test_litellm/proxy/client/test_models.py
@@ -472,14 +472,14 @@ def test_get_invalid_params():
     client = ModelsManagementClient(base_url="http://localhost:8000")
 
     # Test with no parameters
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Exactly one of model_id or model_name must be provided') as exc_info:
         client.get()
     assert "Exactly one of model_id or model_name must be provided" in str(
         exc_info.value
     )
 
     # Test with both parameters
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Exactly one of model_id or model_name must be provided') as exc_info:
         client.get(model_id="123", model_name="gpt-4")
     assert "Exactly one of model_id or model_name must be provided" in str(
         exc_info.value
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 515a7b27c7b..77ada4c11a9 100644
--- a/tests/test_litellm/proxy/common_utils/test_callback_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_callback_utils.py
@@ -586,7 +586,7 @@ def test_initialize_callbacks_on_proxy_rejects_class_valued_entry(probe_config_p
     silently never run the hook. Config load must fail instead."""
     entry = f"{_PROBE_MODULE_NAME}.FloorMaxTokens"
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='litellm_settings\\.callbacks entry') as exc_info:
         _load_callbacks([entry], probe_config_path)
 
     message = str(exc_info.value)
@@ -609,7 +609,7 @@ def test_initialize_callbacks_on_proxy_rejects_non_dispatchable_values(
 ):
     entry = f"{_PROBE_MODULE_NAME}.{attribute}"
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='litellm_settings\\.callbacks entry') as exc_info:
         _load_callbacks([entry], probe_config_path)
 
     message = str(exc_info.value)
@@ -621,7 +621,7 @@ def test_initialize_callbacks_on_proxy_rejects_non_dispatchable_values(
 def test_initialize_callbacks_on_proxy_rejects_class_valued_non_list_value(probe_config_path):
     entry = f"{_PROBE_MODULE_NAME}.FloorMaxTokens"
 
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='litellm_settings\\.callbacks entry') as exc_info:
         _load_callbacks(entry, probe_config_path)
 
     assert entry in str(exc_info.value)
diff --git a/tests/test_litellm/proxy/common_utils/test_path_utils.py b/tests/test_litellm/proxy/common_utils/test_path_utils.py
index c8d58fa8259..8936d910777 100644
--- a/tests/test_litellm/proxy/common_utils/test_path_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_path_utils.py
@@ -42,5 +42,5 @@ class TestSafeFilename:
             safe_filename("..")
 
     def test_empty_rejected(self):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='Empty or unsafe filename'):
             safe_filename("")
diff --git a/tests/test_litellm/proxy/common_utils/test_timezone_utils.py b/tests/test_litellm/proxy/common_utils/test_timezone_utils.py
index 7f686c53c95..dc3917cb48e 100644
--- a/tests/test_litellm/proxy/common_utils/test_timezone_utils.py
+++ b/tests/test_litellm/proxy/common_utils/test_timezone_utils.py
@@ -130,16 +130,16 @@ def test_parse_budget_reset_time_unset_defaults_to_midnight():
 
 
 def test_parse_budget_reset_time_invalid_string_raises():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="hour 'HH:MM' or 'HH:MM:SS' string, e\\.g\\."):
         parse_budget_reset_time("25:00")
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="Invalid budget_reset_time 'noon'; expected a"):
         parse_budget_reset_time("noon")
 
 
 def test_parse_budget_reset_time_non_string_raises():
     # Unquoted "12:00" in YAML parses to the int 720; it must fail loudly,
     # not silently fall back to midnight.
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="hour 'HH:MM' string, e\\.g\\."):
         parse_budget_reset_time(720)
 
 
diff --git a/tests/test_litellm/proxy/conftest.py b/tests/test_litellm/proxy/conftest.py
index 61752997f0f..65e12b7d777 100644
--- a/tests/test_litellm/proxy/conftest.py
+++ b/tests/test_litellm/proxy/conftest.py
@@ -18,6 +18,7 @@ from prisma.errors import ClientNotConnectedError
 _PROXY_MODULE_GLOBALS_TO_ISOLATE = (
     "master_key",
     "prisma_client",
+    "llm_router",
 )
 
 
@@ -56,7 +57,10 @@ def pytest_runtest_setup(item):
 
     Without this, a leaked value (e.g. master_key set by a sibling test)
     flips the auth short-circuit in user_api_key_auth and causes unrelated
-    tests in the same xdist worker to return 401 instead of 200.
+    tests in the same xdist worker to return 401 instead of 200. A leaked
+    llm_router does the same to anything that reads the running router out
+    of sys.modules, such as the PTU rollup's deployment scan, which then
+    counts a sibling test's deployments as if the proxy owned them.
 
     This must be a hook pair, not an autouse fixture: an autouse fixture in
     the root conftest requests monkeypatch, so monkeypatch's undo stack
diff --git a/tests/test_litellm/proxy/db/db_transaction_queue/test_spend_logs_partition_manager.py b/tests/test_litellm/proxy/db/db_transaction_queue/test_spend_logs_partition_manager.py
index e949afce57b..4ea655b8871 100644
--- a/tests/test_litellm/proxy/db/db_transaction_queue/test_spend_logs_partition_manager.py
+++ b/tests/test_litellm/proxy/db/db_transaction_queue/test_spend_logs_partition_manager.py
@@ -308,9 +308,9 @@ async def test_partition_maintenance_issues_nothing_when_the_budget_is_already_s
 
 
 def test_unsupported_interval_raises():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Unsupported partition interval: year'):
         period_start(date(2026, 6, 1), "year")
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Unsupported partition interval: year'):
         next_period_start(date(2026, 6, 1), "year")
 
 
diff --git a/tests/test_litellm/proxy/db/test_prisma_planned_engine_restart.py b/tests/test_litellm/proxy/db/test_prisma_planned_engine_restart.py
index c8e0338eeaa..95e794012ec 100644
--- a/tests/test_litellm/proxy/db/test_prisma_planned_engine_restart.py
+++ b/tests/test_litellm/proxy/db/test_prisma_planned_engine_restart.py
@@ -913,7 +913,7 @@ async def test_health_check_alerts_for_non_connection_errors_during_a_replacemen
         await _yield_to_loop()
         assert wrapper._reconnection_lock.locked() is True
 
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='malformed SELECT'):
             await client.health_check()
 
         gate.set()
diff --git a/tests/test_litellm/proxy/db/test_spend_log_tool_index.py b/tests/test_litellm/proxy/db/test_spend_log_tool_index.py
index 71073fd216e..9c4fbbf41aa 100644
--- a/tests/test_litellm/proxy/db/test_spend_log_tool_index.py
+++ b/tests/test_litellm/proxy/db/test_spend_log_tool_index.py
@@ -327,7 +327,7 @@ class TestFlushToolUsageTransactions:
     async def test_non_connection_errors_do_not_retry(self):
         prisma = MagicMock()
         prisma.db.batch_ = MagicMock(side_effect=ValueError("bad data"))
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="bad data"):
             await flush_tool_usage_transactions(prisma_client=prisma, transactions=[_transaction("r1")])
         prisma.db.batch_.assert_called_once()
 
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 3adf8b8407d..ceb59571389 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
@@ -56,7 +56,7 @@ def _patched(guardrail: BedrockGuardrail, http_response):
 
 
 def test_init_rejects_both_identifier_and_checks():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Bedrock guardrail accepts either'):
         BedrockGuardrail(guardrailIdentifier="gid", checks=CONTENT_FILTER_CHECKS)
 
 
@@ -304,7 +304,7 @@ async def test_truncated_pii_ignored_when_pii_check_not_configured():
 
 @pytest.mark.asyncio
 async def test_checks_with_guardrail_version_rejected():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Bedrock guardrail accepts either'):
         BedrockGuardrail(checks=CONTENT_FILTER_CHECKS, guardrailVersion="DRAFT")
 
 
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_enkryptai.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_enkryptai.py
index e6c94a4c3cd..d31f462a185 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_enkryptai.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_enkryptai.py
@@ -178,7 +178,7 @@ class TestEnkryptAIGuardrailHooks:
         with patch.object(
             enkryptai_guardrail.async_handler, "post", return_value=mock_response
         ):
-            with pytest.raises(ValueError) as exc_info:
+            with pytest.raises(ValueError, match='violation\\(s\\) detected') as exc_info:
                 await enkryptai_guardrail.async_pre_call_hook(
                     user_api_key_dict=mock_user_api_key_dict,
                     cache=MagicMock(),
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py
index 5be0d43c250..523ec1a37b4 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_generic_guardrail_api.py
@@ -767,7 +767,7 @@ class TestErrorHandling:
                 "API Error", request=MagicMock(), response=MagicMock(status_code=500)
             ),
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='Generic Guardrail API failed: API Error') as exc_info:
                 await generic_guardrail.apply_guardrail(
                     inputs={"texts": ["test"]},
                     request_data=mock_request_data_input,
@@ -786,7 +786,7 @@ class TestErrorHandling:
             "post",
             side_effect=httpx.RequestError("Connection failed", request=MagicMock()),
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='Generic Guardrail API failed: Connection failed') as exc_info:
                 await generic_guardrail.apply_guardrail(
                     inputs={"texts": ["test"]},
                     request_data=mock_request_data_input,
@@ -810,7 +810,7 @@ class TestErrorHandling:
             "post",
             side_effect=httpx.RequestError("Connection failed", request=MagicMock()),
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='Generic Guardrail API failed: Connection failed') as exc_info:
                 await guardrail.apply_guardrail(
                     inputs={"texts": ["test"]},
                     request_data=mock_request_data_input,
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_model_armor.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_model_armor.py
index 89b6af27719..14c0d2f9435 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_model_armor.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_model_armor.py
@@ -2334,7 +2334,7 @@ async def test_async_moderation_hook_api_error_fail_on_error_true():
         }
 
         # Should raise the exception since fail_on_error is True
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="API Error") as exc_info:
             await guardrail.async_moderation_hook(
                 data=request_data,
                 user_api_key_dict=mock_user_api_key_dict,
@@ -2374,7 +2374,7 @@ async def test_async_moderation_hook_api_error_fail_on_error_false():
 
         # Even with fail_on_error=False, the decorator may still raise the exception
         # This test verifies that the exception is properly logged and handled
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="API Error") as exc_info:
             await guardrail.async_moderation_hook(
                 data=request_data,
                 user_api_key_dict=mock_user_api_key_dict,
@@ -2865,7 +2865,7 @@ async def test_skip_unscannable_still_fails_closed_on_api_error():
         "post",
         AsyncMock(side_effect=Exception("model armor upstream 500")),
     ):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='model armor upstream') as exc_info:
             await guardrail.async_pre_call_hook(
                 user_api_key_dict=UserAPIKeyAuth(),
                 cache=MagicMock(spec=DualCache),
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 2284f2b678a..8f29ba66814 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
@@ -5652,7 +5652,7 @@ class TestPanwAirsTimeoutCoercion:
         assert isinstance(params.timeout, float)
 
     def test_litellm_params_rejects_garbage_timeout(self):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='validation error for LitellmParams'):
             LitellmParams(
                 guardrail="panw_prisma_airs",
                 mode="pre_call",
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_straiker.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_straiker.py
index a3d86034f70..81604e22c87 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_straiker.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_straiker.py
@@ -90,12 +90,12 @@ def test_config_model_wiring():
 
 
 def test_init_rejects_empty_api_key():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='api_key must be non-empty'):
         StraikerGuardrail(api_key="")
 
 
 def test_init_rejects_invalid_fallback():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="unreachable_fallback must be 'fail_open' or 'fail_closed';"):
         StraikerGuardrail(api_key="k", unreachable_fallback="nope")
 
 
@@ -109,7 +109,7 @@ def test_supported_hooks_limited_to_pre_and_post():
 
 
 def test_during_call_mode_rejected_at_init():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Event hook GuardrailEventHooks\\.during_call is not in the'):
         StraikerGuardrail(api_key="k", event_hook="during_call")
 
 
diff --git a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_tool_permission.py b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_tool_permission.py
index 4b381b67f0e..0c5addbc143 100644
--- a/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_tool_permission.py
+++ b/tests/test_litellm/proxy/guardrails/guardrail_hooks/test_tool_permission.py
@@ -124,7 +124,7 @@ class TestToolPermissionGuardrail:
         assert rule_id is None
 
     def test_rule_requires_name_or_type(self):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='validation error for ToolPermissionRule'):
             ToolPermissionGuardrail(
                 guardrail_name="invalid-rule",
                 rules=[{"id": "no_target", "decision": "allow"}],
@@ -1042,7 +1042,7 @@ class TestToolPermissionGuardrailInMemoryUpdate:
         assert guardrail._check_tool_permission("Secret")[0] is False
         assert guardrail._check_tool_permission("Other")[0] is True
 
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="Invalid regex for tool_name in rule 'bad': unterminated"):
             guardrail.update_in_memory_litellm_params(
                 LitellmParams(
                     guardrail="tool_permission",
diff --git a/tests/test_litellm/proxy/guardrails/test_llm_as_a_judge.py b/tests/test_litellm/proxy/guardrails/test_llm_as_a_judge.py
index 45dec4ddb2d..bd2553b3280 100644
--- a/tests/test_litellm/proxy/guardrails/test_llm_as_a_judge.py
+++ b/tests/test_litellm/proxy/guardrails/test_llm_as_a_judge.py
@@ -230,7 +230,7 @@ def test_parse_judge_verdict_reraises_when_no_json():
 
 def test_parse_judge_verdict_rejects_json_non_object():
     """Valid JSON that is not an object (e.g. a bare list) raises ValueError."""
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='judge response is not a JSON object'):
         _parse_judge_verdict("[1, 2, 3]")
 
 
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 78d2c3af0f3..35c0f8deaf1 100644
--- a/tests/test_litellm/proxy/hooks/test_sensitive_data_routing.py
+++ b/tests/test_litellm/proxy/hooks/test_sensitive_data_routing.py
@@ -227,7 +227,7 @@ class TestCustomGuardrailSensitiveDataRouting:
 
         request_data = {"model": "gpt-4"}
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Cannot route sensitive data without a session_id\\. Ensure') as exc_info:
             guardrail.raise_sensitive_data_route_exception(
                 route_to_model="on-premise-model",
                 request_data=request_data,
diff --git a/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py b/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py
index 8d03857c917..2839acab6b0 100644
--- a/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py
+++ b/tests/test_litellm/proxy/hooks/test_tpm_concurrent.py
@@ -150,7 +150,7 @@ async def test_no_leak_on_over_limit_rejection(rate_limiter):
         f"estimated={estimated}, limit={user_api_key_dict.tpm_limit}"
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Limit type: tokens\\. Current limit') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -685,7 +685,7 @@ async def test_contentless_request_reserves_minimum(rate_limiter):
         f"counter should be 2, got {counter_after_two}"
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Limit type: tokens\\. Current limit') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -1319,7 +1319,7 @@ async def test_project_otpm_rejects_multiple_completion_candidates(rate_limiter)
         "n": 10,
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -1347,7 +1347,7 @@ async def test_project_otpm_reserves_largest_conflicting_output_cap(rate_limiter
         "max_completion_tokens": 100,
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -1377,7 +1377,7 @@ async def test_project_otpm_rejects_google_genai_native_output_cap(
         project_metadata={"model_otpm_limit": {model: 50}},
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -1411,7 +1411,7 @@ async def test_project_otpm_rejects_google_genai_native_candidate_count(
         project_metadata={"model_otpm_limit": {model: 150}},
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -1500,7 +1500,7 @@ async def test_project_otpm_over_limit_rolls_back_itpm_reservation(rate_limiter)
         "max_tokens": 500,  # blows past the 10-token OTPM limit
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -2003,7 +2003,7 @@ async def test_otpm_rejection_does_not_double_refund_combined_tpm(rate_limiter):
         rate_limit_type="tokens",
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -2060,7 +2060,7 @@ async def test_project_itpm_rejects_pretokenized_embedding_input(
         "input": embedding_input,
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_itpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -2250,7 +2250,7 @@ async def test_itpm_reservation_accounts_for_audio_content_not_just_text(rate_li
         ],
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_itpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -2361,7 +2361,7 @@ async def test_itpm_rejects_large_audio_payload_that_would_pass_flat_estimate(
         ],
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_itpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -2622,7 +2622,7 @@ async def test_explicit_zero_output_responses_call_reserves_effective_provider_m
         },
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
@@ -2850,7 +2850,7 @@ async def test_otpm_rejection_releases_stashed_parallel_slot(rate_limiter):
         "rate_limit": {"tokens_per_unit": 5, "window_size": 60},
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_otpm') as exc_info:
         await handler._reserve_project_io_tokens_or_raise(
             descriptors=[otpm_descriptor],
             data=data,
@@ -3296,7 +3296,7 @@ async def test_rerank_query_and_documents_enforce_project_itpm(
         project_metadata={"model_itpm_limit": {"rerank-model": 100}},
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Rate limit exceeded for model_per_project_itpm') as exc_info:
         await handler.async_pre_call_hook(
             user_api_key_dict=user_api_key_dict,
             cache=cache,
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 d4e9ccdca5e..069cfa01178 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
@@ -10179,7 +10179,7 @@ async def test_update_key_creator_reassigned_key_blocked(monkeypatch):
     mock_request = MagicMock()
     mock_request.query_params = {}
 
-    with pytest.raises(Exception) as exc:
+    with pytest.raises(Exception, match='User can only create keys for themselves\\. Got') as exc:
         await update_key_fn(
             request=mock_request,
             data=UpdateKeyRequest(key=test_hashed_token, key_alias="hijacked"),
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 84dee5b05c5..01c0760bd27 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
@@ -2325,7 +2325,7 @@ class TestTemporaryMCPSessionEndpoints:
             "litellm.proxy.management_endpoints.mcp_management_endpoints.validate_and_normalize_mcp_server_payload",
             MagicMock(),
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='User does not have permission to create temporary mcp') as exc_info:
                 await add_session_mcp_server(
                     payload=payload,
                     user_api_key_dict=non_admin,
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 7e4596d154b..42e96ad8659 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
@@ -140,7 +140,7 @@ class TestModelManagementAuthChecks:
     @pytest.mark.asyncio
     async def test_can_user_make_team_model_call_non_premium_fails(self):
         """Test that non-premium users cannot make team model calls"""
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='You must be a LiteLLM Enterprise user to use this feature\\.') as exc_info:
             ModelManagementAuthChecks.can_user_make_team_model_call(
                 team_id="test_team",
                 user_api_key_dict=self.admin_user,
@@ -195,7 +195,7 @@ class TestModelManagementAuthChecks:
         )
         prisma_client = MockPrismaClient(team_exists=True)
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='You must be a LiteLLM Enterprise user to use this feature\\.') as exc_info:
             await ModelManagementAuthChecks.allow_team_model_action(
                 model_params=model_params,
                 user_api_key_dict=self.admin_user,
@@ -216,7 +216,7 @@ class TestModelManagementAuthChecks:
         )
         prisma_client = MockPrismaClient(team_exists=False)
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="Team id=nonexistent_team does not exist in db'\\}") as exc_info:
             await ModelManagementAuthChecks.allow_team_model_action(
                 model_params=model_params,
                 user_api_key_dict=self.admin_user,
@@ -257,7 +257,7 @@ class TestModelManagementAuthChecks:
         )
         prisma_client = MockPrismaClient(team_exists=True, user_admin=False)
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match="Team ID=test_team does not match the API key's team") as exc_info:
             await ModelManagementAuthChecks.can_user_make_model_call(
                 model_params=model_params,
                 user_api_key_dict=self.normal_user,
@@ -1483,7 +1483,7 @@ class TestTeamModelUpdate:
             "litellm.proxy.proxy_server.premium_user",
             True,
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match="does not match the API key's team ID=None, OR you are") as exc_info:
                 await _update_team_model_in_db(
                     db_model=db_model,
                     patch_data=patch_data,
@@ -3256,7 +3256,7 @@ class TestPatchModelBlockedAuthGate:
                 new=AsyncMock(return_value=None),
             ),
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match="Only proxy admins can change a model's blocked flag\\.") as exc_info:
                 await patch_model(
                     model_id="m1",
                     patch_data=updateDeployment(blocked=True),
diff --git a/tests/test_litellm/proxy/management_endpoints/test_ptu_model_settings.py b/tests/test_litellm/proxy/management_endpoints/test_ptu_model_settings.py
index 92a34b5ee7c..a1c38d26b9d 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_ptu_model_settings.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_ptu_model_settings.py
@@ -58,7 +58,7 @@ def test_model_info_accepts_valid_ptu_fields():
 
 
 def test_model_info_rejects_non_positive_count():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='value_error, input_value'):
         ModelInfo(
             id="x",
             team_id="t",
@@ -69,7 +69,7 @@ def test_model_info_rejects_non_positive_count():
 
 
 def test_model_info_rejects_negative_rate():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='value_error, input_value'):
         ModelInfo(
             id="x",
             team_id="t",
@@ -82,7 +82,7 @@ def test_model_info_rejects_negative_rate():
 def test_model_info_rejects_a_count_beyond_the_cap():
     """flat cost multiplies the count by a float, and an unbounded int overflows that
     conversion, which aborted the rollup for every team rather than skipping one model."""
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='validation error for ModelInfo'):
         ModelInfo(id="x", team_id="t", ptu_count=10**400, cost_per_ptu_per_hour=2.0)
 
 
@@ -95,12 +95,12 @@ def test_model_info_accepts_a_count_at_the_cap():
 def test_model_info_rejects_a_non_finite_rate(rate):
     """NaN compares False against every bound, so a bare `< 0` check let it through and the
     deployment then accrued a flat cost of nan."""
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='value_error, input_value'):
         ModelInfo(id="x", team_id="t", ptu_count=5, cost_per_ptu_per_hour=rate)
 
 
 def test_model_info_rejects_a_rate_beyond_the_cap():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='validation error for ModelInfo'):
         ModelInfo(id="x", team_id="t", ptu_count=5, cost_per_ptu_per_hour=ModelInfo.MAX_COST_PER_PTU_PER_HOUR * 2)
 
 
@@ -148,7 +148,7 @@ def test_validate_helper_passes_full_config():
 def test_model_info_rejects_effective_to_before_from():
     import datetime
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='validation error for ModelInfo'):
         ModelInfo(
             id="x",
             team_id="t",
@@ -186,7 +186,7 @@ def test_model_info_compares_mixed_naive_and_aware_timestamps():
     )
     assert info.ptu_effective_to is not None
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='validation error for ModelInfo'):
         ModelInfo(
             id="x",
             team_id="t",
@@ -698,7 +698,7 @@ class TestAddNewModelPtuGate:
         with ExitStack() as stack:
             for active_patch in patches:
                 stack.enter_context(active_patch)
-            with pytest.raises(Exception) as exc:
+            with pytest.raises(Exception, match='PTU cost attribution is disabled, so ptu_count') as exc:
                 await add_new_model(model_params=self._ptu_deployment("ptu-gate-model"), user_api_key_dict=admin)
 
         assert PTU_COST_ATTRIBUTION_ENV_VAR in str(exc.value)
@@ -1273,7 +1273,7 @@ class TestPtuDeploymentsAreNotBilledPerToken:
         with ExitStack() as stack:
             for active_patch in patches:
                 stack.enter_context(active_patch)
-            with pytest.raises(Exception) as exc:
+            with pytest.raises(Exception, match='A PTU deployment bills by reserved capacity, so') as exc:
                 await add_new_model(model_params=deployment, user_api_key_dict=admin)
 
         assert "input_cost_per_token" in str(exc.value)
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 0767288d0bc..e39b09ae073 100644
--- a/tests/test_litellm/proxy/management_endpoints/test_team_endpoints.py
+++ b/tests/test_litellm/proxy/management_endpoints/test_team_endpoints.py
@@ -10253,6 +10253,65 @@ async def test_team_info_returns_model_aliases():
     assert litellm_model_table.model_aliases == {"gpt-4o": "gpt-4o-team-1"}
 
 
+@pytest.mark.asyncio
+async def test_team_info_hydrates_member_emails_from_the_user_table():
+    """/team/info must fill in emails missing from the members_with_roles snapshot.
+
+    members_with_roles is written at add-time, so a member added by user_id alone
+    carries user_email=None forever. Without this join the Admin UI's member table
+    shows "-" for a user that has an email on their user row. A stored email is left
+    exactly as-is.
+    """
+    from fastapi import Request
+
+    from litellm.proxy.management_endpoints import team_endpoints
+
+    team_row = LiteLLM_TeamTable(
+        team_id="team-1",
+        members_with_roles=[
+            Member(user_id="no-email-on-roster", role="admin"),
+            Member(user_id="already-stored", user_email="stored@example.com", role="user"),
+        ],
+    )
+
+    mock_prisma = MagicMock()
+    mock_prisma.db.litellm_teamtable.find_unique = AsyncMock(return_value=team_row)
+    mock_prisma.get_data = AsyncMock(return_value=[])
+
+    find_many = AsyncMock(
+        return_value=[
+            LiteLLM_UserTable(
+                user_id="no-email-on-roster",
+                user_email="real@example.com",
+                max_budget=None,
+                spend=0.0,
+                models=[],
+            )
+        ]
+    )
+
+    with (
+        patch("litellm.proxy.proxy_server.prisma_client", mock_prisma),
+        patch.object(team_endpoints, "get_all_team_memberships", AsyncMock(return_value=[])),
+        patch.object(team_endpoints, "UserRepository") as repo,
+    ):
+        repo.return_value.table.find_many = find_many
+
+        response = await team_endpoints.team_info(
+            http_request=MagicMock(spec=Request),
+            team_id="team-1",
+            user_api_key_dict=UserAPIKeyAuth(user_role=LitellmUserRoles.PROXY_ADMIN),
+        )
+
+    members = response["team_info"].members_with_roles
+    assert [(m.user_id, m.user_email) for m in members] == [
+        ("no-email-on-roster", "real@example.com"),
+        ("already-stored", "stored@example.com"),
+    ]
+    # only the member actually missing an email is looked up
+    assert find_many.await_args.kwargs["where"] == {"user_id": {"in": ["no-email-on-roster"]}}
+
+
 @pytest.mark.asyncio
 async def test_update_model_table_clears_aliases_with_empty_map():
     """``model_aliases={}`` on /team/update must persist an empty map (json.dumps({}))
@@ -11369,6 +11428,141 @@ async def test_resolve_existing_member_user_ids_skips_the_query_when_no_user_ids
     repo.return_value.table.find_many.assert_not_awaited()
 
 
+def _user_row(user_id: str, user_email: str | None) -> LiteLLM_UserTable:
+    return LiteLLM_UserTable(
+        user_id=user_id, user_email=user_email, max_budget=None, spend=0.0, models=[]
+    )
+
+
+@pytest.mark.asyncio
+async def test_hydrate_member_emails_fills_in_emails_the_roster_snapshot_never_captured():
+    """A member added by user_id alone has user_email=None on the stored roster entry.
+
+    /team/info has to fill it in from the user row, or the UI renders "-" for a user
+    that plainly has an email.
+    """
+    from litellm.proxy.management_endpoints.team_endpoints import _hydrate_member_emails
+
+    find_many = AsyncMock(return_value=[_user_row("by-id", "found@example.com")])
+
+    with patch("litellm.proxy.management_endpoints.team_endpoints.UserRepository") as repo:
+        repo.return_value.table.find_many = find_many
+
+        hydrated = await _hydrate_member_emails(
+            prisma_client=MagicMock(),
+            members=[Member(user_id="by-id", role="admin")],
+        )
+
+    assert [(m.user_id, m.user_email, m.role) for m in hydrated] == [("by-id", "found@example.com", "admin")]
+    find_many.assert_awaited_once()
+    assert find_many.await_args.kwargs["where"] == {"user_id": {"in": ["by-id"]}}
+
+
+@pytest.mark.asyncio
+async def test_hydrate_member_emails_never_overwrites_a_stored_email():
+    """The snapshot wins wherever it has a value - hydration only fills blanks.
+
+    Overwriting would be a real behavior change to /team/info; filling a null is not.
+    """
+    from litellm.proxy.management_endpoints.team_endpoints import _hydrate_member_emails
+
+    find_many = AsyncMock(return_value=[_user_row("has-email", "current@example.com")])
+
+    with patch("litellm.proxy.management_endpoints.team_endpoints.UserRepository") as repo:
+        repo.return_value.table.find_many = find_many
+
+        hydrated = await _hydrate_member_emails(
+            prisma_client=MagicMock(),
+            members=[Member(user_id="has-email", user_email="stored@example.com", role="user")],
+        )
+
+    assert hydrated[0].user_email == "stored@example.com"
+    # nothing was missing, so no round-trip either
+    find_many.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_hydrate_member_emails_leaves_members_alone_when_the_user_row_has_no_email():
+    """A user row with no email leaves the member as-is rather than inventing one."""
+    from litellm.proxy.management_endpoints.team_endpoints import _hydrate_member_emails
+
+    with patch("litellm.proxy.management_endpoints.team_endpoints.UserRepository") as repo:
+        repo.return_value.table.find_many = AsyncMock(return_value=[_user_row("no-email", None)])
+
+        hydrated = await _hydrate_member_emails(
+            prisma_client=MagicMock(),
+            members=[Member(user_id="no-email", role="user"), Member(user_email="e@example.com", role="user")],
+        )
+
+    assert [m.user_email for m in hydrated] == [None, "e@example.com"]
+
+
+@pytest.mark.asyncio
+async def test_hydrate_member_emails_skips_the_query_when_every_member_has_one():
+    """No blanks means /team/info pays for no extra query."""
+    from litellm.proxy.management_endpoints.team_endpoints import _hydrate_member_emails
+
+    with patch("litellm.proxy.management_endpoints.team_endpoints.UserRepository") as repo:
+        repo.return_value.table.find_many = AsyncMock()
+
+        hydrated = await _hydrate_member_emails(
+            prisma_client=MagicMock(),
+            members=[Member(user_id="a", user_email="a@example.com", role="user")],
+        )
+
+    assert hydrated[0].user_email == "a@example.com"
+    repo.return_value.table.find_many.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_update_team_members_list_stamps_email_for_a_member_added_by_user_id():
+    """Identity resolution runs both ways, so new roster entries stop being born blank.
+
+    Previously only user_id was backfilled (from email); a member added by user_id
+    was written with user_email=None forever.
+    """
+    from litellm.proxy.management_endpoints.team_endpoints import (
+        _update_team_members_list,
+    )
+
+    mock_team = MagicMock(spec=LiteLLM_TeamTable)
+    mock_team.members_with_roles = []
+
+    await _update_team_members_list(
+        data=TeamMemberAddRequest(team_id="test-team-123", member=Member(user_id="new-user-123", role="user")),
+        complete_team_data=mock_team,
+        updated_users=[_user_row("new-user-123", "new@example.com")],
+    )
+
+    assert len(mock_team.members_with_roles) == 1
+    assert mock_team.members_with_roles[0].user_email == "new@example.com"
+
+
+@pytest.mark.asyncio
+async def test_update_team_members_list_stamps_email_for_each_member_in_a_bulk_add():
+    """Same both-ways resolution for the list branch."""
+    from litellm.proxy.management_endpoints.team_endpoints import (
+        _update_team_members_list,
+    )
+
+    mock_team = MagicMock(spec=LiteLLM_TeamTable)
+    mock_team.members_with_roles = []
+
+    await _update_team_members_list(
+        data=TeamMemberAddRequest(
+            team_id="test-team-123",
+            member=[Member(user_id="u1", role="user"), Member(user_email="u2@example.com", role="admin")],
+        ),
+        complete_team_data=mock_team,
+        updated_users=[_user_row("u1", "u1@example.com"), _user_row("u2", "u2@example.com")],
+    )
+
+    assert [(m.user_id, m.user_email) for m in mock_team.members_with_roles] == [
+        ("u1", "u1@example.com"),
+        ("u2", "u2@example.com"),
+    ]
+
+
 def test_pre_existing_user_ids_counts_ids_filled_in_by_member_resolution():
     """An id the member-resolution step filled in came from a matched row, so it pre-existed.
 
diff --git a/tests/test_litellm/proxy/management_endpoints/usage_endpoints/test_ai_usage_chat.py b/tests/test_litellm/proxy/management_endpoints/usage_endpoints/test_ai_usage_chat.py
index e8a74e41dae..3a32b3cc128 100644
--- a/tests/test_litellm/proxy/management_endpoints/usage_endpoints/test_ai_usage_chat.py
+++ b/tests/test_litellm/proxy/management_endpoints/usage_endpoints/test_ai_usage_chat.py
@@ -458,7 +458,7 @@ class TestUsageAiChatServiceAccountGuard:
             _resolve_fetch_kwargs,
         )
 
-        with pytest.raises(ValueError) as exc_info:
+        with pytest.raises(ValueError, match='Non-admin caller has user_id=None; refusing to issue an') as exc_info:
             _resolve_fetch_kwargs(
                 fn_name="get_usage_data",
                 fn_args={"start_date": "2025-01-01", "end_date": "2025-01-31"},
diff --git a/tests/test_litellm/proxy/management_helpers/test_team_metadata_validation.py b/tests/test_litellm/proxy/management_helpers/test_team_metadata_validation.py
index e4b031ade57..1acb8e7e016 100644
--- a/tests/test_litellm/proxy/management_helpers/test_team_metadata_validation.py
+++ b/tests/test_litellm/proxy/management_helpers/test_team_metadata_validation.py
@@ -671,7 +671,7 @@ async def test_non_callable_validator_is_rejected_with_clean_500():
 
 
 def test_parse_schema_duplicate_error_lists_offending_keys():
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='team_metadata_schema contains duplicate keys: app_name') as exc_info:
         parse_team_metadata_schema(
             [{"key": "cost_center"}, {"key": "app_name"}, {"key": "cost_center"}, {"key": "app_name"}]
         )
diff --git a/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py b/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py
index a05b8ae530c..6ce7af1e2ee 100644
--- a/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py
+++ b/tests/test_litellm/proxy/openai_files_endpoint/test_batch_guardrails.py
@@ -781,7 +781,7 @@ async def test_the_rewrite_closes_its_own_output_when_it_cannot_finish():
     original_read = bg._read_spooled
     bg._read_spooled = _boom
     try:
-        with pytest.raises(OSError):
+        with pytest.raises(OSError, match='no space left on device'):
             rewrite_batch_input_file(source, result)
     finally:
         bg.tempfile.SpooledTemporaryFile = real
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 f994fba371b..d3237f5f49d 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
@@ -2714,7 +2714,7 @@ class TestMilvusProxyRoute:
                 None
             )
 
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='Vector store not found for missing-store') as exc_info:
                 await milvus_proxy_route(
                     endpoint="vectors/search",
                     request=mock_request,
@@ -2779,7 +2779,7 @@ class TestMilvusProxyRoute:
                 mock_vector_store
             )
 
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='api_base not found in vector store configuration for') as exc_info:
                 await milvus_proxy_route(
                     endpoint="vectors/search",
                     request=mock_request,
@@ -2988,7 +2988,7 @@ class TestOpenAIPassthroughRoute:
             "litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints.passthrough_endpoint_router.get_credentials",
             return_value=None,
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match="Required 'OPENAI_API_KEY' in environment to make") as exc_info:
                 await openai_proxy_route(
                     endpoint="v1/chat/completions",
                     request=mock_request,
@@ -3177,7 +3177,7 @@ class TestCursorProxyRoute:
                 [],
             ),
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match='Cursor API key not found\\. Add Cursor credentials via') as exc_info:
                 await cursor_proxy_route(
                     endpoint="v0/agents",
                     request=mock_request,
diff --git a/tests/test_litellm/proxy/policy_engine/test_policy_versioning.py b/tests/test_litellm/proxy/policy_engine/test_policy_versioning.py
index ebebfde5cd3..b6633779326 100644
--- a/tests/test_litellm/proxy/policy_engine/test_policy_versioning.py
+++ b/tests/test_litellm/proxy/policy_engine/test_policy_versioning.py
@@ -157,7 +157,7 @@ class TestUpdatePolicyDraftOnly:
         prod_row = _make_row(policy_id="pid-1", version_status="production")
         prisma.db.litellm_policytable.find_unique = AsyncMock(return_value=prod_row)
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Error updating policy in DB: Only draft versions can be') as exc_info:
             await registry.update_policy_in_db(
                 policy_id="pid-1",
                 policy_request=PolicyUpdateRequest(description="new"),
@@ -341,7 +341,7 @@ class TestUpdateVersionStatus:
         draft = _make_row(policy_id="d-1", version_status="draft")
         prisma.db.litellm_policytable.find_unique = AsyncMock(return_value=draft)
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Error updating version status: Cannot promote draft') as exc_info:
             await registry.update_version_status(
                 policy_id="d-1",
                 new_status="production",
diff --git a/tests/test_litellm/proxy/proxy_server/test_proxy_config.py b/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
index 54ae279d005..47f01fe096d 100644
--- a/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
+++ b/tests/test_litellm/proxy/proxy_server/test_proxy_config.py
@@ -1504,7 +1504,7 @@ async def test_ProxyConfig__init_non_llm_configs_premium_invalid_worker_registry
 async def test_ProxyConfig__init_non_llm_configs_worker_registry_requires_premium(monkeypatch):
     monkeypatch.setattr("litellm.proxy.proxy_server.premium_user", False)
     pc = ProxyConfig()
-    with pytest.raises(ValueError) as exc_info:
+    with pytest.raises(ValueError, match='Trying to use `worker_registry`You must be a LiteLLM') as exc_info:
         await pc._init_non_llm_configs(
             config={
                 "worker_registry": [
@@ -1769,7 +1769,7 @@ def test_ProxyConfig_initialize_secret_manager_none_noop():
 
 def test_ProxyConfig_initialize_secret_manager_invalid_kms_raises():
     pc = ProxyConfig()
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Invalid Key Management System selected'):
         pc.initialize_secret_manager(key_management_system="not-a-real-kms")
 
 
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 15a3e6609f0..b2ec500d045 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
@@ -3263,7 +3263,7 @@ async def test_provider_budget_over(disable_budget_sync):
         model_list=MODEL_LIST,
     )
 
-    with pytest.raises(Exception) as e:
+    with pytest.raises(Exception, match='No deployments available - crossed budget: Exceeded budget') as e:
         await router.acompletion(
             model="azure-gpt-4o",
             messages=[{"role": "user", "content": "Hello, world!"}],
@@ -5096,7 +5096,7 @@ def test_resolve_spend_report_scope_missing_caller_value_400():
 
 @pytest.mark.parametrize("bad_column", ["metadata", "end_user", "evil; DROP TABLE", ""])
 def test_scoped_spend_report_sql_rejects_unknown_column(bad_column):
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Unsupported spend report scope column'):
         spend_management_endpoints._scoped_spend_report_sql(scope_column=bad_column)
 
 
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 9c97b2683b2..e9a22a75607 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
@@ -9,7 +9,6 @@ from typing import Any, Final, cast
 from typing_extensions import ReadOnly, TypedDict
 
 import pytest
-from fastapi.testclient import TestClient
 
 sys.path.insert(
     0, os.path.abspath("../../../..")
@@ -31,8 +30,8 @@ from litellm.proxy.spend_tracking.spend_tracking_utils import (
     _get_response_for_spend_logs_payload,
     _get_spend_logs_metadata,
     _get_vector_store_request_for_spend_logs_payload,
-    _hash_api_key_for_spend_log,
     _is_master_key,
+    _redact_logged_api_key,
     _redact_prompt_leaks_in_error_string,
     _sanitize_error_information_for_spend_logs,
     _sanitize_guardrail_information_for_spend_logs,
@@ -41,6 +40,7 @@ from litellm.proxy.spend_tracking.spend_tracking_utils import (
     get_logging_payload,
     get_spend_logs_id,
 )
+from litellm.proxy.utils import hash_token
 from litellm.types.utils import (
     StandardLoggingHiddenParams,
     StandardLoggingMetadata,
@@ -890,8 +890,6 @@ def test_get_logging_payload_api_key_preserved_when_standard_logging_payload_is_
     assert payload["model"] == "openai/gpt-4.1"
     assert payload["user"] == "test_user"
 
-    print(f"✅ Test passed! api_key preserved: {payload['api_key']}")
-
 
 @pytest.mark.asyncio
 @patch("litellm.proxy.proxy_server.master_key", "sk-master-key")
@@ -1039,18 +1037,6 @@ async def test_api_key_preserved_through_failure_hook_to_database():
     assert payload.get("model") == "gpt-3.5-turbo"
     assert payload.get("user") == "test_user"
 
-    print("\n" + "=" * 80)
-    print("✅ CRITICAL E2E TEST PASSED")
-    print("=" * 80)
-    print(f"Token: {data['token']}")
-    print(f"Payload api_key: {payload_api_key}")
-    print(f"Match: {data['token'] == payload_api_key}")
-    print("=" * 80)
-    print("Production incident bug is FIXED and protected:")
-    print("- Failed requests preserve api_key through entire flow")
-    print("- Both SpendLogs AND DailyUserSpend will have correct api_key")
-    print("=" * 80 + "\n")
-
 
 @patch("litellm.proxy.proxy_server.master_key", None)
 @patch("litellm.proxy.proxy_server.general_settings", {})
@@ -2593,6 +2579,219 @@ def test_sanitize_error_information_redacts_pydantic_assignment_form(
     assert REDACTED_BY_LITELM_STRING in sanitized["error_message"]
 
 
+# ── _redact_logged_api_key unit tests ──────────────────────────────────────
+
+
+def test_redact_logged_api_key_none_returns_none():
+    assert _redact_logged_api_key(None) is None
+
+
+def test_redact_logged_api_key_empty_string_returns_none():
+    assert _redact_logged_api_key("") is None
+
+
+def test_redact_logged_api_key_sk_key_is_hashed():
+    raw = "sk-1234secret"
+    result = _redact_logged_api_key(raw)
+    assert result == hash_token(raw)
+    assert result is not None
+    assert not result.startswith("sk-")
+    assert len(result) == 64
+
+
+def test_redact_logged_api_key_bearer_sk_equals_sk_hash():
+    raw = "sk-1234secret"
+    result_plain = _redact_logged_api_key(raw)
+    result_bearer = _redact_logged_api_key(f"Bearer {raw}")
+    assert result_bearer == result_plain
+
+
+def test_redact_logged_api_key_bearer_case_insensitive():
+    raw = "sk-1234secret"
+    result_lower = _redact_logged_api_key(f"bearer {raw}")
+    result_upper = _redact_logged_api_key(f"BEARER {raw}")
+    expected = hash_token(raw)
+    assert result_lower == expected
+    assert result_upper == expected
+
+
+def test_redact_logged_api_key_non_sk_raw_key_is_hashed():
+    raw = "anthropic-raw-key-xyz"
+    result = _redact_logged_api_key(raw)
+    assert result is not None
+    assert result != raw
+    assert len(result) == 64
+    assert result == hash_token(raw)
+
+
+def test_redact_logged_api_key_already_valid_sha256_passes_through_with_flag():
+    already_hashed = hash_token("sk-some-key")
+    assert len(already_hashed) == 64
+    result = _redact_logged_api_key(already_hashed, already_redacted=True)
+    assert result == already_hashed
+    assert hash_token(already_hashed) != result  # no double-hash
+
+
+def test_redact_logged_api_key_sha256_without_flag_is_hashed():
+    already_hashed = hash_token("sk-some-key")
+    assert len(already_hashed) == 64
+    result = _redact_logged_api_key(already_hashed)
+    assert result is not None
+    assert result != already_hashed
+    assert len(result) == 64
+    assert result == hash_token(already_hashed)
+
+
+def test_redact_logged_api_key_long_opaque_token_is_hashed():
+    raw = "x1" * 450
+    assert len(raw) == 900
+    result = _redact_logged_api_key(raw)
+    assert result is not None
+    assert result != raw
+    assert raw not in result
+    assert len(result) == 64
+    assert result == hash_token(raw)
+
+
+def test_redact_logged_api_key_hashed_jwt_passes_through():
+    jwt_hash = "hashed-jwt-" + "a" * 64
+    result = _redact_logged_api_key(jwt_hash, already_redacted=True)
+    assert result == jwt_hash
+
+
+def test_redact_logged_api_key_hashed_jwt_shape_without_provenance_is_hashed():
+    lookalike = "hashed-jwt-" + "a" * 64
+    result = _redact_logged_api_key(lookalike)
+    assert result == hash_token(lookalike)
+    assert result != lookalike
+
+
+def test_redact_logged_api_key_hashed_jwt_trailing_newline_is_hashed():
+    trailing = "hashed-jwt-" + "a" * 64 + "\n"
+    result = _redact_logged_api_key(trailing, already_redacted=True)
+    assert result == hash_token(trailing)
+    assert result != trailing
+
+
+def test_redact_logged_api_key_hashed_jwt_short_suffix_is_hashed():
+    short_jwt = "hashed-jwt-tooshort"
+    result = _redact_logged_api_key(short_jwt)
+    assert result is not None
+    assert result != short_jwt
+    assert len(result) == 64
+    assert result == hash_token(short_jwt)
+
+
+def test_redact_logged_api_key_master_key_alias_passes_through():
+    from litellm.constants import LITELLM_PROXY_MASTER_KEY_ALIAS
+
+    result = _redact_logged_api_key(LITELLM_PROXY_MASTER_KEY_ALIAS, already_redacted=True)
+    assert result == LITELLM_PROXY_MASTER_KEY_ALIAS
+
+
+def test_redact_logged_api_key_master_key_alias_without_provenance_is_hashed():
+    from litellm.constants import LITELLM_PROXY_MASTER_KEY_ALIAS
+
+    result = _redact_logged_api_key(LITELLM_PROXY_MASTER_KEY_ALIAS)
+    assert result == hash_token(LITELLM_PROXY_MASTER_KEY_ALIAS)
+    assert result != LITELLM_PROXY_MASTER_KEY_ALIAS
+
+
+def test_get_spend_logs_metadata_keeps_master_key_alias_readable():
+    from litellm.constants import LITELLM_PROXY_MASTER_KEY_ALIAS
+
+    meta = _get_spend_logs_metadata(
+        {
+            "user_api_key": LITELLM_PROXY_MASTER_KEY_ALIAS,
+            "user_api_key_hash": LITELLM_PROXY_MASTER_KEY_ALIAS,
+        }
+    )
+    assert meta["user_api_key"] == LITELLM_PROXY_MASTER_KEY_ALIAS
+
+
+def test_redact_logged_api_key_bearer_only_returns_none():
+    # "bearer " with nothing after stripping is equivalent to no key
+    assert _redact_logged_api_key("bearer ") is None
+    assert _redact_logged_api_key("Bearer ") is None
+    assert _redact_logged_api_key("BEARER ") is None
+
+
+# ── _get_spend_logs_metadata key-hash invariant tests ─────────────────────
+
+
+def test_get_spend_logs_metadata_sk_key_hashed():
+    raw = "sk-1234secret"
+    meta = _get_spend_logs_metadata({"user_api_key": raw})
+    assert meta["user_api_key"] == hash_token(raw)
+    assert meta["user_api_key"] is not None
+    result = meta["user_api_key"]
+    assert result is not None
+    assert not result.startswith("sk-")
+    assert len(result) == 64
+
+
+def test_get_spend_logs_metadata_bearer_sk_key_hashed_same_as_plain():
+    raw = "sk-1234secret"
+    meta_plain = _get_spend_logs_metadata({"user_api_key": raw})
+    meta_bearer = _get_spend_logs_metadata({"user_api_key": f"Bearer {raw}"})
+    assert meta_bearer["user_api_key"] == meta_plain["user_api_key"]
+
+
+def test_get_spend_logs_metadata_non_sk_raw_key_hashed():
+    raw = "anthropic-raw-key-xyz"
+    meta = _get_spend_logs_metadata({"user_api_key": raw})
+    result = meta["user_api_key"]
+    assert result is not None
+    assert result != raw
+    assert len(result) == 64
+
+
+def test_get_spend_logs_metadata_already_hashed_unchanged_with_provenance():
+    already_hashed = hash_token("sk-some-key")
+    meta = _get_spend_logs_metadata(
+        {"user_api_key": already_hashed, "user_api_key_hash": already_hashed}
+    )
+    assert meta["user_api_key"] == already_hashed
+    assert hash_token(already_hashed) != meta["user_api_key"]  # no double-hash
+
+
+def test_get_spend_logs_metadata_already_hashed_no_provenance_is_rehashed():
+    already_hashed = hash_token("sk-some-key")
+    meta = _get_spend_logs_metadata({"user_api_key": already_hashed})
+    assert meta["user_api_key"] != already_hashed
+    assert meta["user_api_key"] == hash_token(already_hashed)
+
+
+def test_get_spend_logs_metadata_provenance_bypass_requires_hash_match():
+    already_hashed = hash_token("sk-some-key")
+    different_hash = hash_token("sk-other-key")
+    meta = _get_spend_logs_metadata(
+        {"user_api_key": already_hashed, "user_api_key_hash": different_hash}
+    )
+    assert meta["user_api_key"] == hash_token(already_hashed)
+
+
+def test_get_spend_logs_metadata_hashed_jwt_unchanged():
+    jwt_hash = "hashed-jwt-" + "b" * 64
+    meta = _get_spend_logs_metadata({"user_api_key": jwt_hash, "user_api_key_hash": jwt_hash})
+    assert meta["user_api_key"] == jwt_hash
+
+
+def test_get_spend_logs_metadata_hashed_jwt_shape_without_provenance_is_hashed():
+    lookalike = "hashed-jwt-" + "b" * 64
+    meta = _get_spend_logs_metadata({"user_api_key": lookalike})
+    assert meta["user_api_key"] == hash_token(lookalike)
+    assert meta["user_api_key"] != lookalike
+
+
+def test_get_spend_logs_metadata_none_key_is_none():
+    meta = _get_spend_logs_metadata({"user_api_key": None})
+    assert meta["user_api_key"] is None
+
+
+# ── get_logging_payload key-hash invariant tests ───────────────────────────
+
+
 def test_get_logging_payload_uses_recovered_combined_usage_on_failure():
     """A request that fails mid-stream has no usable response_obj usage, but the
     streaming handler recovers the usage from the chunks already delivered and
@@ -2749,44 +2948,107 @@ def test_get_logging_payload_cache_hit_keeps_raw_litellm_call_id():
     assert json.loads(payload["metadata"])["litellm_call_id"] != payload["request_id"]
 
 
-class TestHashApiKeyForSpendLog:
+class TestSpendLogKeyRedaction:
     """Regression: plaintext API keys with Bearer prefix were stored in
     SpendLogs for failed requests (LIT-4121)"""
 
     def test_bearer_prefixed_sk_key_is_hashed(self):
         raw = "Bearer sk-WLi4iRn4JmbVlTaYw12IOA"
-        result = _hash_api_key_for_spend_log(raw)
+        result = _redact_logged_api_key(raw)
+        assert result is not None
         assert not result.startswith("Bearer")
         assert not result.startswith("sk-")
         assert len(result) == 64
 
     def test_bare_sk_key_is_hashed(self):
         raw = "sk-WLi4iRn4JmbVlTaYw12IOA"
-        result = _hash_api_key_for_spend_log(raw)
+        result = _redact_logged_api_key(raw)
+        assert result is not None
         assert not result.startswith("sk-")
         assert len(result) == 64
 
     def test_bearer_lowercase_is_handled(self):
         raw = "bearer sk-WLi4iRn4JmbVlTaYw12IOA"
-        result = _hash_api_key_for_spend_log(raw)
+        result = _redact_logged_api_key(raw)
+        assert result is not None
         assert not result.startswith("bearer")
         assert not result.startswith("sk-")
         assert len(result) == 64
 
     def test_already_hashed_key_unchanged(self):
         hashed = "bcfe8173f5447f10be0e7fb37aaa8b97829d5c9e0498232152f9d123456789ab"
-        assert _hash_api_key_for_spend_log(hashed) == hashed
+        assert _redact_logged_api_key(hashed, already_redacted=True) == hashed
 
-    def test_bearer_prefixed_non_sk_key_strips_prefix(self):
+    def test_bearer_prefixed_non_sk_key_is_hashed(self):
         raw = "Bearer some-other-token-format"
-        result = _hash_api_key_for_spend_log(raw)
-        assert result == "some-other-token-format"
+        result = _redact_logged_api_key(raw)
+        assert result == hash_token("some-other-token-format")
+        assert result is not None
         assert not result.startswith("Bearer")
 
     def test_bearer_and_bare_produce_same_hash(self):
         bare = "sk-WLi4iRn4JmbVlTaYw12IOA"
         bearer = "Bearer sk-WLi4iRn4JmbVlTaYw12IOA"
-        assert _hash_api_key_for_spend_log(bare) == _hash_api_key_for_spend_log(bearer)
+        assert _redact_logged_api_key(bare) == _redact_logged_api_key(bearer)
+
+
+@patch("litellm.proxy.proxy_server.master_key", None)
+@patch("litellm.proxy.proxy_server.general_settings", {})
+def test_get_logging_payload_non_sk_raw_key_both_fields_hashed():
+    raw = "anthropic-raw-key-xyz"
+    kwargs = {
+        "model": "openai/gpt-4.1",
+        "messages": [{"role": "user", "content": "Hello"}],
+        "call_type": "acompletion",
+        "litellm_params": {
+            "metadata": {
+                "user_api_key": raw,
+                "user_api_key_user_id": "test_user",
+                "user_api_key_team_id": "test_team",
+            }
+        },
+    }
+    payload = get_logging_payload(
+        kwargs=kwargs,
+        response_obj=Exception("error"),
+        start_time=datetime.datetime.now(timezone.utc),
+        end_time=datetime.datetime.now(timezone.utc),
+    )
+
+    assert payload["api_key"] != raw
+    assert len(payload["api_key"]) == 64
+
+    parsed_meta = json.loads(payload["metadata"])
+    assert parsed_meta["user_api_key"] != raw
+    assert parsed_meta["user_api_key"] is not None
+    assert len(parsed_meta["user_api_key"]) == 64
+
+
+def test_get_logging_payload_keeps_master_key_alias_readable():
+    from litellm.constants import LITELLM_PROXY_MASTER_KEY_ALIAS
+
+    kwargs = {
+        "model": "openai/gpt-4.1",
+        "messages": [{"role": "user", "content": "Hello"}],
+        "call_type": "acompletion",
+        "litellm_params": {
+            "metadata": {
+                "user_api_key": LITELLM_PROXY_MASTER_KEY_ALIAS,
+                "user_api_key_hash": LITELLM_PROXY_MASTER_KEY_ALIAS,
+                "user_api_key_user_id": "test_user",
+            }
+        },
+    }
+    payload = get_logging_payload(
+        kwargs=kwargs,
+        response_obj=Exception("error"),
+        start_time=datetime.datetime.now(timezone.utc),
+        end_time=datetime.datetime.now(timezone.utc),
+    )
+
+    assert payload["api_key"] == LITELLM_PROXY_MASTER_KEY_ALIAS
+    parsed_meta = json.loads(payload["metadata"])
+    assert parsed_meta["user_api_key"] == LITELLM_PROXY_MASTER_KEY_ALIAS
 
 
 @patch("litellm.proxy.proxy_server.master_key", None)
@@ -3291,3 +3553,69 @@ def test_get_logging_payload_falls_back_to_kwargs_model_when_slp_model_missing()
         end_time=datetime.datetime.now(timezone.utc),
     )
     assert payload["model"] == "azure_ai/model_router/model-router"
+
+
+@patch("litellm.proxy.proxy_server.master_key", None)
+@patch("litellm.proxy.proxy_server.general_settings", {})
+def test_get_logging_payload_empty_key_slp_none_is_empty_string_not_none_literal():
+    kwargs = {
+        "model": "openai/gpt-4.1",
+        "messages": [{"role": "user", "content": "Hello"}],
+        "call_type": "acompletion",
+        "litellm_params": {
+            "metadata": {
+                "user_api_key_user_id": "test_user",
+            }
+        },
+    }
+    payload = get_logging_payload(
+        kwargs=kwargs,
+        response_obj=Exception("error"),
+        start_time=datetime.datetime.now(timezone.utc),
+        end_time=datetime.datetime.now(timezone.utc),
+    )
+
+    assert payload["api_key"] == "", (
+        f"Expected empty string but got {payload['api_key']!r}; "
+        "dropping _redact_logged_api_key's 'or \"\"' guard would yield 'None' here"
+    )
+
+
+def test_get_spend_logs_metadata_sibling_fields_preserved():
+    raw = "anthropic-raw-key-xyz"
+    meta = _get_spend_logs_metadata(
+        {
+            "user_api_key": raw,
+            "user_api_key_alias": "my-alias",
+            "user_api_key_team_id": "team-123",
+        }
+    )
+    assert meta["user_api_key"] == hash_token(raw)
+    assert meta["user_api_key_alias"] == "my-alias"
+    assert meta["user_api_key_team_id"] == "team-123"
+
+
+def test_redact_logged_api_key_partial_sha256_is_hashed():
+    partial_hex = "a" * 63
+    result = _redact_logged_api_key(partial_hex)
+    assert result is not None
+    assert result != partial_hex
+    assert len(result) == 64
+    assert result == hash_token(partial_hex)
+
+
+def test_redact_logged_api_key_bearer_already_hashed_passes_through_with_flag():
+    already_hashed = hash_token("sk-some-key")
+    assert len(already_hashed) == 64
+    result = _redact_logged_api_key(f"Bearer {already_hashed}", already_redacted=True)
+    assert result == already_hashed
+    assert hash_token(already_hashed) != result
+
+
+def test_redact_logged_api_key_bearer_sha256_without_flag_is_hashed():
+    already_hashed = hash_token("sk-some-key")
+    assert len(already_hashed) == 64
+    result = _redact_logged_api_key(f"Bearer {already_hashed}")
+    assert result is not None
+    assert result != already_hashed
+    assert result == hash_token(already_hashed)
diff --git a/tests/test_litellm/proxy/test_common_request_processing.py b/tests/test_litellm/proxy/test_common_request_processing.py
index c693f5ab2cb..716fba370df 100644
--- a/tests/test_litellm/proxy/test_common_request_processing.py
+++ b/tests/test_litellm/proxy/test_common_request_processing.py
@@ -435,7 +435,7 @@ class TestProxyBaseLLMRequestProcessing:
 
         # Test with invalid header value (should raise ValueError when converting to float)
         headers_with_invalid = {"x-litellm-stream-timeout": "invalid"}
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="could not convert string to float: 'invalid"):
             LiteLLMProxyRequestSetup._get_stream_timeout_from_request(headers_with_invalid)
 
     @pytest.mark.asyncio
diff --git a/tests/test_litellm/proxy/test_enforce_user_param.py b/tests/test_litellm/proxy/test_enforce_user_param.py
index 6891123e70e..1001372aeb5 100644
--- a/tests/test_litellm/proxy/test_enforce_user_param.py
+++ b/tests/test_litellm/proxy/test_enforce_user_param.py
@@ -56,7 +56,7 @@ class TestEnforceUserParamPostGetFiltering:
             new_callable=AsyncMock,
             return_value=True,
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match="user' param not passed in\\. 'enforce_user_param'=True") as exc_info:
                 await common_checks(
                     request_body=request_body,
                     team_object=None,
@@ -175,7 +175,7 @@ class TestEnforceUserParamPostGetFiltering:
             new_callable=AsyncMock,
             return_value=True,
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match="user' param not passed in\\. 'enforce_user_param'=True") as exc_info:
                 await common_checks(
                     request_body=request_body,
                     team_object=None,
@@ -405,7 +405,7 @@ class TestEnforceUserParamEdgeCases:
             new_callable=AsyncMock,
             return_value=True,
         ):
-            with pytest.raises(Exception) as exc_info:
+            with pytest.raises(Exception, match="user' param not passed in\\. 'enforce_user_param'=True") as exc_info:
                 await common_checks(
                     request_body=request_body,
                     team_object=None,
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 b1071150f3b..636974d5deb 100644
--- a/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
+++ b/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
@@ -2279,12 +2279,12 @@ def test_get_num_retries_from_request():
 
     # Test case 7: Header present with invalid value (should raise ValueError when int() is called)
     headers_with_invalid = {"x-litellm-num-retries": "invalid"}
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='invalid literal for int\\(\\) with base'):
         LiteLLMProxyRequestSetup._get_num_retries_from_request(headers_with_invalid)
 
     # Test case 8: Header present with float string (should raise ValueError when int() is called)
     headers_with_float = {"x-litellm-num-retries": "3.5"}
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='invalid literal for int\\(\\) with base'):
         LiteLLMProxyRequestSetup._get_num_retries_from_request(headers_with_float)
 
     # Test case 9: Header present with negative number
@@ -2324,7 +2324,7 @@ def test_get_keepalive_seconds_from_request():
 
     # Header present with invalid value raises ValueError, matching the other
     # x-litellm-* numeric header helpers (_get_timeout_from_request, etc.)
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="could not convert string to float: 'not-a-number"):
         LiteLLMProxyRequestSetup._get_keepalive_seconds_from_request(
             {"x-litellm-keepalive-seconds": "not-a-number"}
         )
diff --git a/tests/test_litellm/proxy/test_proxy_server.py b/tests/test_litellm/proxy/test_proxy_server.py
index 75aa716bb85..83e9095c8ec 100644
--- a/tests/test_litellm/proxy/test_proxy_server.py
+++ b/tests/test_litellm/proxy/test_proxy_server.py
@@ -1507,7 +1507,7 @@ def test_team_info_masking():
         "langfuse_public_key": "public-test-key",
     }
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match="secr\\*\\*\\*\\*\\*\\*\\*-key', 'langfuse_public_key':") as exc_info:
         proxy_config._get_team_config(
             team_id="test_dev",
             all_teams_config=[team1_info],
diff --git a/tests/test_litellm/proxy/test_spend_log_cleanup.py b/tests/test_litellm/proxy/test_spend_log_cleanup.py
index ce0b6b755cc..bf1538183ab 100644
--- a/tests/test_litellm/proxy/test_spend_log_cleanup.py
+++ b/tests/test_litellm/proxy/test_spend_log_cleanup.py
@@ -82,10 +82,10 @@ def test_spend_log_cleanup_cron_scheduling():
     assert trigger_weekly is not None
 
     # Invalid cron expression should raise ValueError
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Wrong number of fields; got'):
         CronTrigger.from_crontab("invalid cron")
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='is higher than the maximum value'):
         CronTrigger.from_crontab("60 25 * * *")  # Invalid minute and hour
 
 
diff --git a/tests/test_litellm/proxy/test_team_org_move.py b/tests/test_litellm/proxy/test_team_org_move.py
index 2dc961bec85..064e9de550e 100644
--- a/tests/test_litellm/proxy/test_team_org_move.py
+++ b/tests/test_litellm/proxy/test_team_org_move.py
@@ -97,7 +97,7 @@ class TestValidateTeamOrgChange:
         team = _make_team(member_ids=["sso-user-001"])
         org = _make_org(members=[])
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Cannot move team to organization\\. Team has user_id') as exc_info:
             validate_team_org_change(
                 team=team, organization=org, llm_router=router, is_proxy_admin=False
             )
diff --git a/tests/test_litellm/proxy/utils/helpers/test_team_configs.py b/tests/test_litellm/proxy/utils/helpers/test_team_configs.py
index 0e0906892b0..185d4d26ff4 100644
--- a/tests/test_litellm/proxy/utils/helpers/test_team_configs.py
+++ b/tests/test_litellm/proxy/utils/helpers/test_team_configs.py
@@ -66,7 +66,7 @@ def test_is_valid_team_configs_short_circuits_when_team_id_none():
 def test_is_valid_team_configs_raises_on_model_not_in_team_models():
     team_config = {"models": ["gpt-4o"]}
     request_data = {"model": "claude-haiku"}
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='claude-haiku\\.  Valid models for team are') as exc_info:
         _is_valid_team_configs(
             team_id="team-1",
             team_config=team_config,
diff --git a/tests/test_litellm/proxy/utils/prisma_and_spend/test_proxy_update_spend.py b/tests/test_litellm/proxy/utils/prisma_and_spend/test_proxy_update_spend.py
index 7057a112c83..93c99c7fd04 100644
--- a/tests/test_litellm/proxy/utils/prisma_and_spend/test_proxy_update_spend.py
+++ b/tests/test_litellm/proxy/utils/prisma_and_spend/test_proxy_update_spend.py
@@ -561,7 +561,7 @@ async def test_update_spend_logs_does_not_requeue_non_transport_failures(
     proxy_logging.failure_handler = AsyncMock()
     mock_prisma_client.spend_log_transactions = []
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="bad payload"):
         await ProxyUpdateSpend.update_spend_logs(
             n_retry_times=1,
             prisma_client=mock_prisma_client,
diff --git a/tests/test_litellm/proxy/utils/proxy_logging/test_callback_capabilities_class.py b/tests/test_litellm/proxy/utils/proxy_logging/test_callback_capabilities_class.py
index 9452e8042bd..75a91177f00 100644
--- a/tests/test_litellm/proxy/utils/proxy_logging/test_callback_capabilities_class.py
+++ b/tests/test_litellm/proxy/utils/proxy_logging/test_callback_capabilities_class.py
@@ -181,7 +181,7 @@ def test_has_streaming_callbacks_error_when_resolution_fails(monkeypatch):
         "get_custom_logger_compatible_class",
         lambda *a, **kw: (_ for _ in ()).throw(ValueError("nope")),
     )
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="nope"):
         ProxyLogging.has_streaming_callbacks()
 
 
diff --git a/tests/test_litellm/responses/test_responses_websocket_all_providers.py b/tests/test_litellm/responses/test_responses_websocket_all_providers.py
index 2d523bfdeb3..e8333214ea8 100644
--- a/tests/test_litellm/responses/test_responses_websocket_all_providers.py
+++ b/tests/test_litellm/responses/test_responses_websocket_all_providers.py
@@ -84,7 +84,7 @@ class TestResponsesAPIWebSocketSupport:
 
     def test_azure_websocket_url_requires_api_base(self):
         config = AzureOpenAIResponsesAPIConfig()
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='api_base is required for Azure WebSocket'):
             config.get_websocket_url(api_base=None, litellm_params={})
 
     def test_azure_model_not_in_websocket_url(self):
diff --git a/tests/test_litellm/router_strategy/adaptive_router/test_bandit.py b/tests/test_litellm/router_strategy/adaptive_router/test_bandit.py
index ab322f0fb37..78390cc1193 100644
--- a/tests/test_litellm/router_strategy/adaptive_router/test_bandit.py
+++ b/tests/test_litellm/router_strategy/adaptive_router/test_bandit.py
@@ -100,7 +100,7 @@ def test_score_combines_quality_and_cost():
 
 
 def test_pick_best_empty_dict_raises():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='pick_best called with no models'):
         pick_best({}, {})
 
 
diff --git a/tests/test_litellm/router_strategy/test_router_tag_routing.py b/tests/test_litellm/router_strategy/test_router_tag_routing.py
index 73491490b14..60b1166de73 100644
--- a/tests/test_litellm/router_strategy/test_router_tag_routing.py
+++ b/tests/test_litellm/router_strategy/test_router_tag_routing.py
@@ -656,7 +656,7 @@ async def test_negation_all_excluded_raises():
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -699,7 +699,7 @@ async def test_negation_ban_only_cannot_escape_default_pool():
     # Sending only "!default" must NOT route to the paid deployment.
     # The base pool for ban-only is the default pool; banning the only
     # default deployment should raise rather than falling through to paid.
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -969,7 +969,7 @@ async def test_negation_exhausts_entire_fallback_chain():
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="primary",
             messages=[{"role": "user", "content": "hi"}],
@@ -1719,7 +1719,7 @@ async def test_required_and_unmatched_raises_by_default():
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -1751,7 +1751,7 @@ async def test_required_and_combined_with_positive_unmatched_raises_by_default()
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -1973,7 +1973,7 @@ async def test_negation_combined_with_positive_unmatched_raises_by_default():
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -2131,7 +2131,7 @@ async def test_mixed_constraint_survivor_unmatched_by_positive_tag_raises_by_def
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -2224,7 +2224,7 @@ async def test_allow_fail_open_denied_when_request_includes_unknown_tag():
         enable_tag_filtering=True,
     )
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gpt-4",
             messages=[{"role": "user", "content": "hi"}],
@@ -2538,7 +2538,7 @@ async def test_plain_tag_exhaustion_with_universal_default_tag_raises_by_default
         "litellm.router._async_get_cooldown_deployments",
         new=AsyncMock(return_value=["quality-high-1", "quality-high-2"]),
     ):
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
             await router.acompletion(
                 model="gpt-4",
                 messages=[{"role": "user", "content": "hi"}],
@@ -2767,7 +2767,7 @@ async def test_allow_fail_open_raises_when_inherited_constraint_alone_is_unsatis
     # allow_fail_open unset.
     router = _eu_region_router()
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="chat",
             messages=[{"role": "user", "content": "hi"}],
@@ -2941,7 +2941,7 @@ async def test_tagged_request_direct_to_plain_group_still_rejected():
     # tag filtering must reject exactly as before.
     router = _tagged_marker_router()
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gemini-flash",
             messages=[{"role": "user", "content": "hi"}],
@@ -2962,7 +2962,7 @@ async def test_caller_forged_consumption_stamp_is_neutralized_by_the_hook():
     # tag filtering runs.
     router = _tagged_marker_router()
 
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await router.acompletion(
             model="gemini-flash",
             messages=[{"role": "user", "content": "hi"}],
@@ -2984,7 +2984,7 @@ async def test_inherited_constraint_still_applies_to_the_routed_tier():
     # &region:eu comes from key/team policy (present in inherited_tags):
     # consuming the router-selecting "route" tag must not also discard the
     # inherited requirement, so a tier without the tag still raises...
-    with pytest.raises(Exception) as exc_info:
+    with pytest.raises(Exception, match='Not allowed to access model due to tags configuration\\.') as exc_info:
         await _tagged_marker_router().acompletion(
             model="gpt4o",
             messages=[{"role": "user", "content": "hi"}],
diff --git a/tests/test_litellm/sandbox/test_e2b_sandbox.py b/tests/test_litellm/sandbox/test_e2b_sandbox.py
index cc5b12156a1..e01b9120416 100644
--- a/tests/test_litellm/sandbox/test_e2b_sandbox.py
+++ b/tests/test_litellm/sandbox/test_e2b_sandbox.py
@@ -293,7 +293,7 @@ async def test_public_lifecycle_create_run_delete():
 
 @pytest.mark.asyncio
 async def test_unsupported_provider_raises():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match="not-a-provider' is not a valid SandboxProviders"):
         await litellm.acreate_sandbox(provider="not-a-provider")
 
 
diff --git a/tests/test_litellm/secret_managers/test_base_secret_manager.py b/tests/test_litellm/secret_managers/test_base_secret_manager.py
index cba6a99ab7f..e1ccb91c381 100644
--- a/tests/test_litellm/secret_managers/test_base_secret_manager.py
+++ b/tests/test_litellm/secret_managers/test_base_secret_manager.py
@@ -32,7 +32,7 @@ from litellm.secret_managers.base_secret_manager import raise_if_unsafe_secret_n
     ],
 )
 def test_raise_if_unsafe_secret_name_rejects_traversal_and_line_breaks(secret_name):
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Invalid secret_name'):
         raise_if_unsafe_secret_name(secret_name)
 
 
diff --git a/tests/test_litellm/test_github_close_low_quality_prs.py b/tests/test_litellm/test_github_close_low_quality_prs.py
index e3b653dde64..2a891ca72f5 100644
--- a/tests/test_litellm/test_github_close_low_quality_prs.py
+++ b/tests/test_litellm/test_github_close_low_quality_prs.py
@@ -697,7 +697,7 @@ class TestListOpenItemsNoCap:
 
     def test_list_open_items_rejects_unknown_kind(self, closer_module):
         shared = self._shared(closer_module)
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match="kind must be 'pr' or 'issue', got 'both"):
             shared.list_open_items("both", repo="o/r", fields="number")
 
     def test_fetch_open_prs_delegates_with_no_cap(self, closer_module, monkeypatch):
diff --git a/tests/test_litellm/test_github_triage_with_llm.py b/tests/test_litellm/test_github_triage_with_llm.py
index 96b77e80457..ddffb978b48 100644
--- a/tests/test_litellm/test_github_triage_with_llm.py
+++ b/tests/test_litellm/test_github_triage_with_llm.py
@@ -665,11 +665,11 @@ class TestParseVerdict:
         assert triage_module.parse_verdict(raw)["verdict"] == "pass"
 
     def test_should_raise_for_unparseable_text(self, triage_module):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='could not extract JSON from LLM response: not even close to'):
             triage_module.parse_verdict("not even close to json")
 
     def test_should_raise_for_empty(self, triage_module):
-        with pytest.raises(ValueError):
+        with pytest.raises(ValueError, match='empty LLM response'):
             triage_module.parse_verdict("")
 
 
diff --git a/tests/test_litellm/test_redact_string_in_error_paths.py b/tests/test_litellm/test_redact_string_in_error_paths.py
index 8eddc2b1a5a..1c4d91397d1 100644
--- a/tests/test_litellm/test_redact_string_in_error_paths.py
+++ b/tests/test_litellm/test_redact_string_in_error_paths.py
@@ -234,7 +234,7 @@ class TestRouterFallbackFailureTracebackRedaction:
                 raise ValueError(f"primary deployment failed api_key={secret}")
             except ValueError as original_exception:
                 with caplog.at_level(logging.DEBUG, logger="LiteLLM Router"):
-                    with pytest.raises(ValueError):
+                    with pytest.raises(ValueError, match='primary deployment failed api_key=sk-testsecretvalu'):
                         await router.async_function_with_fallbacks_common_utils(
                             e=original_exception,
                             disable_fallbacks=False,
diff --git a/tests/test_litellm/test_redis.py b/tests/test_litellm/test_redis.py
index 3aa4bc58f13..c645a67ef84 100644
--- a/tests/test_litellm/test_redis.py
+++ b/tests/test_litellm/test_redis.py
@@ -131,7 +131,7 @@ def test_get_redis_url_from_environment_missing_host_port(monkeypatch):
     monkeypatch.delenv("REDIS_PORT", raising=False)
 
     # Call the function and expect a ValueError
-    with pytest.raises(ValueError) as excinfo:
+    with pytest.raises(ValueError, match="Either 'REDIS_URL' or both 'REDIS_HOST' and 'REDIS_PORT") as excinfo:
         get_redis_url_from_environment()
 
     # Check the error message
@@ -149,7 +149,7 @@ def test_get_redis_url_from_environment_missing_port(monkeypatch):
     monkeypatch.setenv("REDIS_HOST", "redis-server")
 
     # Call the function and expect a ValueError
-    with pytest.raises(ValueError) as excinfo:
+    with pytest.raises(ValueError, match="Either 'REDIS_URL' or both 'REDIS_HOST' and 'REDIS_PORT") as excinfo:
         get_redis_url_from_environment()
 
     # Check the error message
diff --git a/tests/test_litellm/test_router.py b/tests/test_litellm/test_router.py
index b50dc92c220..a47525749f6 100644
--- a/tests/test_litellm/test_router.py
+++ b/tests/test_litellm/test_router.py
@@ -953,7 +953,7 @@ async def test_arouter_filter_team_based_models():
     assert result is not None
 
     # FAILS
-    with pytest.raises(Exception) as e:
+    with pytest.raises(Exception, match='No deployments available for selected model, Try again in') as e:
         result = await router.acompletion(
             model="gpt-3.5-turbo",
             messages=[{"role": "user", "content": "Hello, world!"}],
@@ -1225,7 +1225,7 @@ def test_add_invalid_provider_to_router():
         ],
     )
 
-    with pytest.raises(Exception) as e:
+    with pytest.raises(Exception, match='Unsupported provider - vertex_ai_eu') as e:
         router.add_deployment(
             Deployment(
                 model_name="vertex_ai/*",
@@ -1320,7 +1320,7 @@ async def test_router_ageneric_api_call_with_fallbacks_helper():
     with patch.object(router, "async_get_available_deployment") as mock_get_deployment:
         mock_get_deployment.side_effect = Exception("No deployment available")
 
-        with pytest.raises(Exception) as exc_info:
+        with pytest.raises(Exception, match='No deployment available') as exc_info:
             await router._ageneric_api_call_with_fallbacks_helper(
                 model="gpt-3.5-turbo",
                 original_generic_function=mock_generic_function,
@@ -1394,7 +1394,7 @@ async def test_router_ageneric_api_call_with_fallbacks_helper():
                 with patch.object(
                     router, "async_routing_strategy_pre_call_checks"
                 ) as mock_pre_call_checks:
-                    with pytest.raises(Exception) as exc_info:
+                    with pytest.raises(Exception, match='Mock failure') as exc_info:
                         await router._ageneric_api_call_with_fallbacks_helper(
                             model="gpt-3.5-turbo",
                             original_generic_function=mock_failing_function,
@@ -3737,7 +3737,7 @@ def test_count_pre_call_check_tokens_across_api_surfaces():
     assert string_input_tokens > 0
     assert list_input_tokens > 0
 
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='Either messages or input must be provided to count tokens'):
         router._count_pre_call_check_tokens(messages=None, input=None)
 
 
diff --git a/tests/test_litellm/test_router_model_cost_isolation.py b/tests/test_litellm/test_router_model_cost_isolation.py
index 5bb854c12e0..dc210f900bf 100644
--- a/tests/test_litellm/test_router_model_cost_isolation.py
+++ b/tests/test_litellm/test_router_model_cost_isolation.py
@@ -1706,7 +1706,7 @@ def test_an_incomplete_reservation_is_refused_rather_than_served(dropped):
     state the operator was trying to leave."""
     incomplete = {k: v for k, v in _PTU_MODEL_INFO.items() if k != dropped}
 
-    with pytest.raises(ValueError) as raised:
+    with pytest.raises(ValueError, match="PTU configuration on model 'gpt") as raised:
         _ptu_router(model_info=incomplete, litellm_params={"input_cost_per_token": 5e-06})
 
     assert "gpt-4o-ptu" in str(raised.value)
@@ -1726,7 +1726,7 @@ def test_the_refusal_reason_is_the_one_the_model_endpoint_answers_with(dropped,
     incomplete = {k: v for k, v in _PTU_MODEL_INFO.items() if k != dropped}
 
     assert ptu_config_error(incomplete) == expected
-    with pytest.raises(ValueError) as raised:
+    with pytest.raises(ValueError, match="PTU configuration on model 'gpt") as raised:
         _ptu_router(model_info=incomplete)
 
     assert expected in str(raised.value)
diff --git a/tests/test_litellm/test_utils.py b/tests/test_litellm/test_utils.py
index 041c60e0ba6..075b455e4b5 100644
--- a/tests/test_litellm/test_utils.py
+++ b/tests/test_litellm/test_utils.py
@@ -4370,7 +4370,7 @@ class TestVertexEmbeddingEncodingFormat:
         assert "encoding_format" not in optional_params
 
     def test_encoding_format_base64_still_rejected_without_drop_params(self):
-        with pytest.raises(Exception) as excinfo:
+        with pytest.raises(Exception, match='To drop these, set `litellm\\.drop_params=True` or for proxy') as excinfo:
             litellm.utils.get_optional_params_embeddings(
                 model="gemini-embedding-001",
                 encoding_format="base64",
diff --git a/tests/test_litellm/types/test_router.py b/tests/test_litellm/types/test_router.py
index 5ce5eca4954..accd3b32a0d 100644
--- a/tests/test_litellm/types/test_router.py
+++ b/tests/test_litellm/types/test_router.py
@@ -87,5 +87,5 @@ def test_pricing_strings_are_coerced_to_float():
 
 
 def test_invalid_pricing_is_rejected():
-    with pytest.raises(ValueError):
+    with pytest.raises(ValueError, match='validation error for ModelInfo'):
         ModelInfo(id="x", input_cost_per_token="free")