diff --git a/litellm/__init__.py b/litellm/__init__.py
index 261457d6889..ccfbf80369f 100644
--- a/litellm/__init__.py
+++ b/litellm/__init__.py
@@ -538,7 +538,7 @@ context_window_fallbacks: Optional[List] = None
 content_policy_fallbacks: Optional[List] = None
 allowed_fails: int = 3
 allow_dynamic_callback_disabling: bool = True
-num_retries_per_request: Optional[int] = None  # cap on Router retries of one model group; resets per fallback hop
+num_retries_per_request: Optional[int] = None  # for the request overall (incl. fallbacks + model retries)
 ####### SECRET MANAGERS #####################
 secret_manager_client: Optional[Any] = (
     None  # list of instantiated key management clients - e.g. azure kv, infisical, etc.
diff --git a/litellm/litellm_core_utils/core_helpers.py b/litellm/litellm_core_utils/core_helpers.py
index 6e76bf9d49e..15380bc5d57 100644
--- a/litellm/litellm_core_utils/core_helpers.py
+++ b/litellm/litellm_core_utils/core_helpers.py
@@ -309,8 +309,8 @@ def max_retries_per_request_hit(kwargs: Mapping[str, object], num_retries_per_re
     metadata: Final = kwargs.get(get_metadata_variable_name_from_kwargs(kwargs))
     if not isinstance(metadata, Mapping):
         return False
-    attempted_retries: Final = metadata.get("attempted_retries")
-    return type(attempted_retries) is int and 0 < attempted_retries and num_retries_per_request <= attempted_retries
+    retry_count: Final = metadata.get("request_retry_count")
+    return type(retry_count) is int and 0 < retry_count and num_retries_per_request <= retry_count
 
 
 def get_or_create_metadata_bucket(
diff --git a/litellm/llms/anthropic/chat/guardrail_translation/handler.py b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
index 656e9978eff..2ea20143f0c 100644
--- a/litellm/llms/anthropic/chat/guardrail_translation/handler.py
+++ b/litellm/llms/anthropic/chat/guardrail_translation/handler.py
@@ -20,6 +20,7 @@ from itertools import chain, repeat
 from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, Final, Protocol, cast, overload, runtime_checkable
 
+from pydantic import TypeAdapter, ValidationError
 from typing_extensions import ReadOnly, TypedDict, assert_never
 
 from litellm._logging import verbose_proxy_logger
@@ -104,9 +105,24 @@ class ToolResultBlockTextTarget:
     block_idx: int
 
 
-InputWriteBackTarget = (
-    MessageContentTarget | ContentBlockTextTarget | ToolResultStringTarget | ToolResultBlockTextTarget
-)
+@dataclass(frozen=True, slots=True)
+class SystemStringTarget:
+    pass
+
+
+@dataclass(frozen=True, slots=True)
+class SystemBlockTextTarget:
+    block_idx: int
+
+
+@dataclass(frozen=True, slots=True)
+class ToolUseInputTarget:
+    msg_idx: int
+    content_idx: int
+
+
+MessageTextTarget = MessageContentTarget | ContentBlockTextTarget | ToolResultStringTarget | ToolResultBlockTextTarget
+InputWriteBackTarget = SystemStringTarget | SystemBlockTextTarget | MessageTextTarget
 
 
 def _as_str_mapping(value: Mapping[str, object]) -> Mapping[str, object]:
@@ -147,10 +163,17 @@ class ScannedText:
     target: InputWriteBackTarget
 
 
+@dataclass(frozen=True, slots=True)
+class ScannedToolCall:
+    tool_call: ChatCompletionToolCallChunk
+    target: ToolUseInputTarget
+
+
 @dataclass(frozen=True, slots=True)
 class ExtractedInput:
     scanned: tuple[ScannedText, ...]
     images: tuple[str, ...]
+    tool_calls: tuple[ScannedToolCall, ...] = ()
 
 
 EMPTY_EXTRACTED_INPUT: Final = ExtractedInput(scanned=(), images=())
@@ -162,6 +185,74 @@ class _ToolCallShape:
     arguments: str
 
 
+def _is_client_tool_use(block: Mapping[str, object]) -> bool:
+    return (
+        block.get("type") == "tool_use"
+        and isinstance(block.get("id"), str)
+        and isinstance(block.get("name"), str)
+        and isinstance(block.get("input"), dict)
+    )
+
+
+def _write_back_system_block(system: object, block_idx: int, response: str) -> None:
+    if not isinstance(system, list):
+        return
+    text_blocks: Final = tuple(block for block in system if isinstance(block, dict) and block.get("type") == "text")
+    if block_idx < len(text_blocks):
+        text_blocks[block_idx]["text"] = (
+            response  # mutable-ok: guardrails rewrite the caller's request payload in place
+        )
+
+
+def _write_back_message_text(message: _WritableMessage, target: MessageTextTarget, response: str) -> None:
+    content: Final = message.get("content", None)
+    if content is None:
+        return
+    match target:
+        case MessageContentTarget():
+            if isinstance(content, str):
+                message["content"] = response  # mutable-ok: guardrails rewrite the caller's request payload in place
+        case ContentBlockTextTarget(content_idx=content_idx):
+            if isinstance(content, list):
+                content[content_idx]["text"] = (
+                    response  # mutable-ok: guardrails rewrite the caller's request payload in place
+                )
+        case ToolResultStringTarget(content_idx=content_idx):
+            if isinstance(content, list):
+                content[content_idx]["content"] = (
+                    response  # mutable-ok: guardrails rewrite the caller's request payload in place
+                )
+        case ToolResultBlockTextTarget(content_idx=content_idx, block_idx=block_idx):
+            if isinstance(content, list):
+                content[content_idx]["content"][block_idx]["text"] = (
+                    response  # mutable-ok: guardrails rewrite the caller's request payload in place
+                )
+        case _:
+            assert_never(target)
+
+
+_TOOL_USE_INPUT_ADAPTER: Final = TypeAdapter(dict[str, object])
+
+
+def _rewritten_tool_use_input(arguments: str) -> Mapping[str, object] | None:
+    try:
+        return _TOOL_USE_INPUT_ADAPTER.validate_json(arguments)
+    except ValidationError:
+        return None
+
+
+def _write_back_tool_use(
+    message: _WritableMessage, target: ToolUseInputTarget, shape: _ToolCallShape, rewritten_input: Mapping[str, object]
+) -> None:
+    content: Final = message.get("content", None)
+    block: Final = content[target.content_idx] if isinstance(content, list) else None
+    if not isinstance(block, dict):
+        return
+    block["input"] = rewritten_input  # mutable-ok: guardrails rewrite the caller's request payload in place
+    if shape.name is not None and shape.name != block.get("name"):
+        block["name"] = shape.name  # mutable-ok: guardrails rewrite the caller's request payload in place
+
+
 @dataclass(frozen=True, slots=True)
 class _SSEFieldRewrite:
     """One field of one nested section of a buffered SSE event, rewritten."""
@@ -453,9 +544,8 @@ class AnthropicMessagesHandler(BaseTranslation):
         skip_tool: Final = effective_skip_tool_message_for_guardrail(guardrail_to_apply)
         scan_only_tool_results: Final = effective_scan_only_tool_results_for_guardrail(guardrail_to_apply)
 
-        # Exclude only the trusted top-level prompt. In-sequence system entries are untrusted
-        # and must stay aligned with texts_to_check for positional masking. When the top-level
-        # prompt is included, the pre-existing count mismatch disables positional masking.
+        # The top-level prompt is translated on its own below so it can be hoisted in front of
+        # any mid-turn system entries and scanned first, aligned with that structured position.
         translation_source: Final = {  # mutable-ok: API message payload
             key: value for key, value in data.items() if key != "system"
         }
@@ -491,7 +581,12 @@ class AnthropicMessagesHandler(BaseTranslation):
             ]
         )
 
-        # Step 1: Extract all text content and images
+        # Step 1: Extract all text content, images, and tool calls
+        top_level_system_scanned: Final = (
+            ()
+            if hoisted_system_message is None or scan_only_tool_results
+            else self._extract_top_level_system_text(hoisted_system_message)
+        )
         extracted: Final = tuple(
             self._extract_input_text_and_images(
                 message=message,
@@ -502,17 +597,27 @@ class AnthropicMessagesHandler(BaseTranslation):
             )
             for msg_idx, message in enumerate(messages)
         )
-        scanned: Final = tuple(item for one_message in extracted for item in one_message.scanned)
+        scanned: Final = (
+            *top_level_system_scanned,
+            *(item for one_message in extracted for item in one_message.scanned),
+        )
         texts_to_check: Final = [item.text for item in scanned]  # mutable-ok: GenericGuardrailAPIInputs takes list[str]
         images_to_check: Final = [
             image for one_message in extracted for image in one_message.images
         ]  # mutable-ok: GenericGuardrailAPIInputs takes list[str]
+        scanned_tool_calls: Final = tuple(item for one_message in extracted for item in one_message.tool_calls)
+        tool_calls_to_check: Final = [
+            item.tool_call for item in scanned_tool_calls
+        ]  # mutable-ok: GenericGuardrailAPIInputs takes list[ChatCompletionToolCallChunk]
+        pre_guardrail_tool_calls: Final = _tool_call_shapes(tool_calls_to_check)
 
-        # Step 2: Apply guardrail to all texts in batch
-        if texts_to_check:
+        # Step 2: Apply guardrail to all texts and tool calls in batch
+        if texts_to_check or tool_calls_to_check:
             inputs: Final = GenericGuardrailAPIInputs(texts=texts_to_check)
             if images_to_check:
                 inputs["images"] = images_to_check
+            if tool_calls_to_check:
+                inputs["tool_calls"] = tool_calls_to_check
             if tools_to_check:
                 inputs["tools"] = tools_to_check
             original_structured_messages: Final = structured_messages
@@ -573,9 +678,16 @@ class AnthropicMessagesHandler(BaseTranslation):
             else:
                 if guardrailed_texts and len(guardrailed_texts) != len(scanned):
                     raise unappliable_request_rewrite(guardrail_to_apply.guardrail_name)
+                self._apply_guardrail_tool_calls_to_input(
+                    messages=messages,
+                    scanned_tool_calls=scanned_tool_calls,
+                    pre_guardrail_tool_calls=pre_guardrail_tool_calls,
+                    returned_tool_calls=guardrailed_inputs.get("tool_calls"),
+                    guardrail_name=guardrail_to_apply.guardrail_name,
+                )
                 # Step 3: Map guardrail responses back to original message structure
                 await self._apply_guardrail_responses_to_input(
-                    messages=messages,
+                    data=data,
                     responses=guardrailed_texts,
                     scanned=scanned,
                 )
@@ -601,6 +713,19 @@ class AnthropicMessagesHandler(BaseTranslation):
         hoisted: Final = probe.get("messages") or []  # mutable-ok: API message payload
         return hoisted[0] if hoisted else None
 
+    @staticmethod
+    def _extract_top_level_system_text(hoisted_system_message: AllMessageValues) -> tuple[ScannedText, ...]:
+        content: Final = hoisted_system_message.get("content")
+        if isinstance(content, str):
+            return (ScannedText(content, SystemStringTarget()),)
+        if not isinstance(content, list):
+            return ()
+        return tuple(
+            ScannedText(text_str, SystemBlockTextTarget(block_idx))
+            for block_idx, block in enumerate(content)
+            if isinstance(block, dict) and isinstance(text_str := block.get("text"), str)
+        )
+
     @staticmethod
     def _openai_system_message_to_anthropic(
         message: Mapping[str, object],
@@ -855,9 +980,25 @@ class AnthropicMessagesHandler(BaseTranslation):
             for content_idx, content_item in enumerate(content)
             if isinstance(content_item, dict)
         )
+        tool_use_blocks: Final = (
+            ()
+            if scan_only_tool_results
+            else tuple(
+                (content_idx, content_item)
+                for content_idx, content_item in enumerate(content)
+                if isinstance(content_item, dict) and _is_client_tool_use(content_item)
+            )
+        )
         return ExtractedInput(
             scanned=tuple(item for block in blocks for item in block.scanned),
             images=tuple(image for block in blocks for image in block.images),
+            tool_calls=tuple(
+                ScannedToolCall(
+                    tool_call=AnthropicConfig.convert_tool_use_to_openai_format(content_item, tool_call_idx),
+                    target=ToolUseInputTarget(msg_idx, content_idx),
+                )
+                for tool_call_idx, (content_idx, content_item) in enumerate(tool_use_blocks)
+            ),
         )
 
     @classmethod
@@ -943,43 +1084,59 @@ class AnthropicMessagesHandler(BaseTranslation):
 
     async def _apply_guardrail_responses_to_input(
         self,
-        messages: Sequence[_WritableMessage],
-        responses: list[str],
+        data: dict[str, object],  # mutable-ok: API message payload
+        responses: Sequence[str],
         scanned: tuple[ScannedText, ...],
     ) -> None:
         """
-        Apply guardrail responses back to input messages.
+        Apply guardrail responses back to the top-level system prompt and the input messages.
         """
+        raw_messages: Final = data.get("messages")
+        messages: Final[Sequence[_WritableMessage]] = raw_messages if isinstance(raw_messages, list) else ()
         for item, guardrail_response in zip(scanned, responses):
-            target = item.target
-            message = messages[target.msg_idx]
-            content = message.get("content", None)
-            if content is None:
-                continue
-
-            match target:
-                case MessageContentTarget():
-                    if isinstance(content, str):
-                        message["content"] = (
-                            guardrail_response  # mutable-ok: guardrails rewrite the caller's request payload in place
-                        )
-                case ContentBlockTextTarget(content_idx=content_idx):
-                    if isinstance(content, list):
-                        content[content_idx]["text"] = (
-                            guardrail_response  # mutable-ok: guardrails rewrite the caller's request payload in place
-                        )
-                case ToolResultStringTarget(content_idx=content_idx):
-                    if isinstance(content, list):
-                        content[content_idx]["content"] = (
-                            guardrail_response  # mutable-ok: guardrails rewrite the caller's request payload in place
-                        )
-                case ToolResultBlockTextTarget(content_idx=content_idx, block_idx=block_idx):
-                    if isinstance(content, list):
-                        content[content_idx]["content"][block_idx]["text"] = (
+            match item.target:
+                case SystemStringTarget():
+                    if isinstance(data.get("system"), str):
+                        data["system"] = (
                             guardrail_response  # mutable-ok: guardrails rewrite the caller's request payload in place
                         )
+                case SystemBlockTextTarget(block_idx=block_idx):
+                    _write_back_system_block(data.get("system"), block_idx, guardrail_response)
+                case (
+                    MessageContentTarget()
+                    | ContentBlockTextTarget()
+                    | ToolResultStringTarget()
+                    | ToolResultBlockTextTarget() as message_target
+                ):
+                    _write_back_message_text(messages[message_target.msg_idx], message_target, guardrail_response)
                 case _:
-                    assert_never(target)
+                    assert_never(item.target)
+
+    @staticmethod
+    def _apply_guardrail_tool_calls_to_input(
+        messages: Sequence[_WritableMessage],
+        scanned_tool_calls: tuple[ScannedToolCall, ...],
+        pre_guardrail_tool_calls: tuple[_ToolCallShape, ...],
+        returned_tool_calls: Sequence[object] | None,
+        guardrail_name: str | None,
+    ) -> None:
+        post_guardrail_tool_calls: Final = _tool_call_shapes(
+            returned_tool_calls
+            if returned_tool_calls is not None and len(returned_tool_calls) == len(pre_guardrail_tool_calls)
+            else tuple(item.tool_call for item in scanned_tool_calls)
+        )
+        rewritten: Final = tuple(
+            (item, after, _rewritten_tool_use_input(after.arguments))
+            for item, before, after in zip(scanned_tool_calls, pre_guardrail_tool_calls, post_guardrail_tool_calls)
+            if before != after
+        )
+        applicable: Final = tuple(
+            (item, after, rewritten_input) for item, after, rewritten_input in rewritten if rewritten_input is not None
+        )
+        if len(applicable) != len(rewritten):
+            raise unappliable_request_rewrite(guardrail_name)
+        for item, after, rewritten_input in applicable:
+            _write_back_tool_use(messages[item.target.msg_idx], item.target, after, rewritten_input)
 
     async def process_output_response(
         self,
diff --git a/litellm/llms/bedrock/base_aws_llm.py b/litellm/llms/bedrock/base_aws_llm.py
index f52c1cec6a8..385d5898569 100644
--- a/litellm/llms/bedrock/base_aws_llm.py
+++ b/litellm/llms/bedrock/base_aws_llm.py
@@ -11,6 +11,7 @@ from concurrent.futures import ThreadPoolExecutor
 from datetime import datetime
 from functools import partial
 from threading import Lock
+from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, ClassVar, Final, Literal, ParamSpec, TypeVar, cast, get_args, overload
 
 import httpx
@@ -96,6 +97,77 @@ def _assume_role_params(
             )
 
 
+_SecureTransportBool = TypedDict("_SecureTransportBool", {"aws:SecureTransport": ReadOnly[Literal["true"]]})
+
+
+class _SecureTransportCondition(TypedDict):
+    Bool: ReadOnly[_SecureTransportBool]
+
+
+class _SessionPolicyStatement(TypedDict):
+    Sid: ReadOnly[str]
+    Effect: ReadOnly[Literal["Allow"]]
+    Action: ReadOnly[tuple[str, ...]]
+    Resource: ReadOnly[Literal["*"]]
+    Condition: ReadOnly[_SecureTransportCondition]
+
+
+class WebIdentitySessionPolicy(TypedDict):
+    Version: ReadOnly[Literal["2012-10-17"]]
+    Statement: ReadOnly[tuple[_SessionPolicyStatement, ...]]
+
+
+_WEB_IDENTITY_SESSION_POLICY_ACTIONS: Final[Mapping[str, tuple[str, ...]]] = MappingProxyType(
+    {
+        "BedrockLiteLLM": (
+            "bedrock:InvokeModel",
+            "bedrock:InvokeModelWithResponseStream",
+            "bedrock:CountTokens",
+            "bedrock:Rerank",
+            "bedrock:Retrieve",
+            "bedrock:ListKnowledgeBases",
+            "bedrock:InvokeAgent",
+            "bedrock:ApplyGuardrail",
+            "bedrock:GetGuardrail",
+            "bedrock:ListGuardrails",
+        ),
+        "BedrockAgentCoreLiteLLM": (
+            "bedrock-agentcore:InvokeAgentRuntime",
+            "bedrock-agentcore:InvokeAgentRuntimeForUser",
+            "bedrock-agentcore:InvokeGateway",
+        ),
+        "ClaudePlatformLiteLLM": (
+            "aws-external-anthropic:CreateInference",
+            "aws-external-anthropic:CreateBatchInference",
+            "aws-external-anthropic:CancelBatchInference",
+            "aws-external-anthropic:DeleteBatchInference",
+            "aws-external-anthropic:CountTokens",
+            "aws-external-anthropic:Get*",
+            "aws-external-anthropic:List*",
+        ),
+        "BedrockMantleLiteLLM": ("bedrock-mantle:CreateInference",),
+    }
+)
+
+_SECURE_TRANSPORT_ONLY: Final = _SecureTransportCondition(Bool=_SecureTransportBool({"aws:SecureTransport": "true"}))
+
+
+def build_web_identity_session_policy() -> WebIdentitySessionPolicy:
+    return WebIdentitySessionPolicy(
+        Version="2012-10-17",
+        Statement=tuple(
+            _SessionPolicyStatement(
+                Sid=sid,
+                Effect="Allow",
+                Action=actions,
+                Resource="*",
+                Condition=_SECURE_TRANSPORT_ONLY,
+            )
+            for sid, actions in _WEB_IDENTITY_SESSION_POLICY_ACTIONS.items()
+        ),
+    )
+
+
 class BedrockRequestTarget(BaseModel):
     aws_region_name: str
     aws_bedrock_runtime_endpoint: str | None
@@ -940,60 +1012,12 @@ class BaseAWSLLM(SignsRequestsWithAWS):
         # auth only (static creds + IRSA take other code paths).
         # https://docs.aws.amazon.com/STS/latest/APIReference/API_AssumeRoleWithWebIdentity.html
         # https://boto3.amazonaws.com/v1/documentation/api/latest/reference/services/sts/client/assume_role_with_web_identity.html
-        bedrock_session_policy: Final = {
-            "Version": "2012-10-17",
-            "Statement": [
-                {
-                    "Sid": "BedrockLiteLLM",
-                    "Effect": "Allow",
-                    "Action": [
-                        "bedrock:InvokeModel",
-                        "bedrock:InvokeModelWithResponseStream",
-                        "bedrock:CountTokens",
-                        "bedrock:ApplyGuardrail",
-                        "bedrock:GetGuardrail",
-                        "bedrock:ListGuardrails",
-                    ],
-                    "Resource": "*",
-                    "Condition": {"Bool": {"aws:SecureTransport": "true"}},
-                },
-                # Claude Platform on AWS (added by #27678 for the
-                # ``bedrock/claude_platform/<model>`` route) lives under
-                # a separate IAM action namespace; without these entries
-                # the OIDC path 403s on every claude_platform request
-                # even with a fully permissive identity policy (#30200).
-                {
-                    "Sid": "ClaudePlatformLiteLLM",
-                    "Effect": "Allow",
-                    "Action": [
-                        "aws-external-anthropic:CreateInference",
-                        "aws-external-anthropic:CreateBatchInference",
-                        "aws-external-anthropic:CancelBatchInference",
-                        "aws-external-anthropic:DeleteBatchInference",
-                        "aws-external-anthropic:CountTokens",
-                        "aws-external-anthropic:Get*",
-                        "aws-external-anthropic:List*",
-                    ],
-                    "Resource": "*",
-                    "Condition": {"Bool": {"aws:SecureTransport": "true"}},
-                },
-                {
-                    "Sid": "BedrockMantleLiteLLM",
-                    "Effect": "Allow",
-                    "Action": [
-                        "bedrock-mantle:CreateInference",
-                    ],
-                    "Resource": "*",
-                    "Condition": {"Bool": {"aws:SecureTransport": "true"}},
-                },
-            ],
-        }
         assume_role_params: Final = {
             "RoleArn": aws_role_name,
             "RoleSessionName": aws_session_name,
             "WebIdentityToken": oidc_token,
             "DurationSeconds": 3600,
-            "Policy": json.dumps(bedrock_session_policy, separators=(",", ":")),
+            "Policy": json.dumps(build_web_identity_session_policy(), separators=(",", ":")),
         }
 
         # Add ExternalId parameter if provided
diff --git a/litellm/llms/gemini/realtime/transformation.py b/litellm/llms/gemini/realtime/transformation.py
index c92af7de145..79985569c5f 100644
--- a/litellm/llms/gemini/realtime/transformation.py
+++ b/litellm/llms/gemini/realtime/transformation.py
@@ -115,6 +115,19 @@ def _parse_setup(session_configuration_request: str) -> BidiGenerateContentSetup
     return envelope.get("setup", empty_setup)
 
 
+def _grounding_metadata_from_frame(frame: Mapping[str, object]) -> tuple[Mapping[str, object], ...]:
+    """Read ``serverContent.groundingMetadata`` off the frame that carries the turn's usage.
+
+    Live reports grounding in the server frames rather than in ``usageMetadata``, and it emits both
+    on the same frame, so the per-query charge is countable at the point usage is built.
+    """
+    server_content: Final = frame.get("serverContent")
+    if not isinstance(server_content, Mapping):
+        return ()
+    metadata: Final = server_content.get("groundingMetadata")
+    return (metadata,) if isinstance(metadata, Mapping) else ()
+
+
 # Google bills Live transcription at an estimated 25 audio tokens/sec of input and
 # 175 text tokens/min of output (ai.google.dev/gemini-api/docs/pricing).
 GEMINI_LIVE_TRANSCRIBE_AUDIO_TOKENS_PER_SECOND: Final = 25
@@ -323,7 +336,7 @@ class GeminiRealtimeConfig(BaseRealtimeConfig):
                 )
             elif key == "input_audio_transcription" and value is not None:
                 optional_params["inputAudioTranscription"] = {}
-            elif key == "turn_detection":
+            elif key == "turn_detection" and value is not None:
                 value_typed = cast(OpenAIRealtimeTurnDetection, value)
                 if (
                     isinstance(value_typed, dict)
@@ -1049,6 +1062,11 @@ class GeminiRealtimeConfig(BaseRealtimeConfig):
                     {**cast(dict, message), "usageMetadata": resolved_usage_metadata},
                 ),
             )
+            grounding_metadata: Final = _grounding_metadata_from_frame(message)
+            if grounding_metadata:
+                VertexGeminiConfig._set_grounding_usage_counters(  # pyright: ignore[reportPrivateUsage]  # shared with the chat path; no public alias exists yet
+                    _chat_completion_usage, grounding_metadata
+                )
         else:
             _chat_completion_usage = get_empty_usage()
 
diff --git a/litellm/proxy/client/cli/README.md b/litellm/proxy/client/cli/README.md
index cb867cf9e61..a5a2675ed6e 100644
--- a/litellm/proxy/client/cli/README.md
+++ b/litellm/proxy/client/cli/README.md
@@ -580,8 +580,8 @@ What the command changed is recorded in `~/.litellm/claude_configure_state.json`
 `lite configure claude`, `lite login --config-claude`, `lite up` and `lite autoroute up` also install a status line (`~/.litellm/statusline.py`, registered as `statusLine` in `~/.claude/settings.json` unless you already run one) that shows which model the auto-router actually served the last turn and, once the proxy has recorded the session, what the session cost against the router's savings baseline:
 
 ```
-claude-auto · Routed to: claude-haiku-4-5  -63% vs Claude Opus 5
-LiteLLM       ████████░░░░░░░░░░░░░░░░  $0.14
+Routed to: claude-haiku-4-5  -63% vs Claude Opus 5
+claude-auto   ████████░░░░░░░░░░░░░░░░  $0.14
 Claude Opus 5 ████████████████████████  $0.38
 ```
 
diff --git a/litellm/proxy/client/cli/commands/statusline_script.py b/litellm/proxy/client/cli/commands/statusline_script.py
index 5493586f627..47be3888a58 100644
--- a/litellm/proxy/client/cli/commands/statusline_script.py
+++ b/litellm/proxy/client/cli/commands/statusline_script.py
@@ -28,6 +28,7 @@ import os
 import sys
 import tempfile
 import time
+import unicodedata
 import urllib.error
 import urllib.request
 from collections.abc import Callable, Mapping
@@ -42,7 +43,6 @@ FETCH_TIMEOUT_SECONDS: Final = 3
 BAR_WIDTH: Final = 24
 BAR_FULL: Final = "\u2588"
 BAR_EMPTY: Final = "\u2591"
-SEPARATOR: Final = " \u00b7 "
 TRANSCRIPT_SCAN_LIMIT_BYTES: Final = 4 * 1024 * 1024
 CLAUDE_BASE_URL_ENV_KEYS: Final = ("ANTHROPIC_BASE_URL",)
 CLAUDE_API_KEY_ENV_KEYS: Final = ("ANTHROPIC_AUTH_TOKEN", "ANTHROPIC_API_KEY")
@@ -50,7 +50,6 @@ CODEX_BASE_URL_ENV_KEYS: Final = ("OPENAI_BASE_URL",)
 CODEX_API_KEY_ENV_KEYS: Final = ("OPENAI_API_KEY",)
 CODEX_STOP_EVENT: Final = "Stop"
 SYNTHETIC_MODEL: Final = "<synthetic>"
-LITELLM_LABEL: Final = "LiteLLM"
 RESET: Final = "\033[0m"
 BOLD: Final = "\033[1m"
 DIM: Final = "\033[90m"
@@ -302,31 +301,37 @@ def _bar(fraction: float, color: str, width: int, use_color: bool) -> str:
     return f"{color}{BAR_FULL * filled}{DIM}{BAR_EMPTY * (width - filled)}{RESET}"
 
 
+def _display_width(label: str) -> int:
+    return sum(
+        2 if unicodedata.east_asian_width(character) in ("W", "F") else 1
+        for character in label
+        if unicodedata.category(character) not in ("Mn", "Me")
+    )
+
+
 def render(model: str, session: Session | None, config_dir: Path, use_color: bool, bar_width: int = BAR_WIDTH) -> str:
     def paint(code: str, text: str) -> str:
         return f"{code}{text}{RESET}" if use_color else text
 
     routed: Final = paint(BOLD, f"Routed to: {model}")
-    if session is None:
+    if session is None or session.baseline_model is None or session.baseline_spend <= 0:
         return routed
-    header: Final = f"{session.router_name}{SEPARATOR}{routed}"
-    if session.baseline_model is None or session.baseline_spend <= 0:
-        return header
     reference: Final = baseline_label(session.baseline_model, config_dir)
     pct: Final = (session.baseline_spend - session.spend) / session.baseline_spend * 100
     delta: Final = paint(LITELLM_COLOR, f"{'-' if pct >= 0 else '+'}{abs(round(pct))}% vs {reference}")
     peak: Final = max(session.spend, session.baseline_spend)
-    label_width: Final = max(len(LITELLM_LABEL), len(reference))
+    label_width: Final = max(_display_width(session.router_name), _display_width(reference))
     rows: Final = (
-        (LITELLM_LABEL, session.spend, LITELLM_COLOR),
+        (session.router_name, session.spend, LITELLM_COLOR),
         (reference, session.baseline_spend, BASELINE_COLOR),
     )
     lines: Final = (
-        f"{paint(DIM, label.ljust(label_width))} {_bar(amount / peak, color, bar_width, use_color)} "
+        f"{paint(DIM, label + ' ' * (label_width - _display_width(label)))} "
+        f"{_bar(amount / peak, color, bar_width, use_color)} "
         f"{paint(DIM, f'${amount:.2f}')}"
         for label, amount, color in rows
     )
-    return "\n".join((f"{header}  {delta}", *lines))
+    return "\n".join((f"{routed}  {delta}", *lines))
 
 
 def color_enabled(env: Mapping[str, str]) -> bool:
diff --git a/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py b/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py
index 3bc0dfabefc..9002e2aea07 100644
--- a/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py
+++ b/litellm/proxy/guardrails/guardrail_hooks/panw_prisma_airs/panw_prisma_airs.py
@@ -1600,8 +1600,8 @@ class PanwPrismaAirsHandler(CustomGuardrail):
 
         Args:
             texts: Flattened text entries from the framework.
-            messages: Original request messages (request_data["messages"]),
-                      NOT structured_messages (which may have injected system content).
+            messages: The structured messages the framework flattened into ``texts``,
+                      hoisted top-level system prompt included, so positions line up.
 
         Returns a set of scannable indices, or None on count mismatch or no user/developer
         message (safety fallback to existing role-filter behavior).
@@ -1788,15 +1788,10 @@ class PanwPrismaAirsHandler(CustomGuardrail):
             structured_messages: Final = inputs.get("structured_messages")
             if structured_messages:
                 # For Anthropic /v1/messages: default to latest-user-only scanning.
-                # Uses request_data["messages"] (original format), NOT structured_messages
-                # (which has injected system content from adapter translation).
                 if self._use_latest_user_only(request_data, logging_obj):
-                    original_messages: Final = request_data.get("messages")
-                    if original_messages:
-                        scannable_indices = self._get_latest_user_text_indices(texts, original_messages)
+                    scannable_indices = self._get_latest_user_text_indices(texts, structured_messages)
                 # Fall through to existing role filtering if:
                 # - not Anthropic, OR flag explicitly False, OR
-                # - no original messages, OR
                 # - latest-user extraction returned None (no user / count mismatch)
                 if scannable_indices is None:
                     scannable_indices = self._get_scannable_text_indices(texts, structured_messages)
diff --git a/litellm/proxy/litellm_pre_call_utils.py b/litellm/proxy/litellm_pre_call_utils.py
index c55ac389fda..5ff039ca436 100644
--- a/litellm/proxy/litellm_pre_call_utils.py
+++ b/litellm/proxy/litellm_pre_call_utils.py
@@ -336,7 +336,7 @@ _CLIENT_PRICING_METADATA_FIELDS: Final = frozenset({"model_info", "standard_logg
 # and read by spend logs as fact; a client value has no legitimate meaning and no
 # key or team setting keeps it, so the strip is never gated.
 _ROUTER_RESERVED_METADATA_FIELDS: Final = frozenset(
-    {"attempted_fallbacks", "original_model_group", CLIENT_OUTPUT_CEILING_METADATA_KEY}
+    {"attempted_fallbacks", "original_model_group", "request_retry_count", CLIENT_OUTPUT_CEILING_METADATA_KEY}
 )
 _ALLOW_CLIENT_PRICING_OVERRIDE_METADATA_KEY: Final = "allow_client_pricing_override"
 
diff --git a/litellm/proxy/management_endpoints/key_management_endpoints.py b/litellm/proxy/management_endpoints/key_management_endpoints.py
index 0184da46c0f..f2fe7614d43 100644
--- a/litellm/proxy/management_endpoints/key_management_endpoints.py
+++ b/litellm/proxy/management_endpoints/key_management_endpoints.py
@@ -147,6 +147,7 @@ from litellm.types.proxy.management_endpoints.key_management_endpoints import (
     BulkUpdateKeyRequest,
     BulkUpdateKeyResponse,
     BulkUpdateTeamKeysRequest,
+    CustomKeyPolicyRequest,
     FailedKeyUpdate,
     KeySearchWhere,
     SuccessfulKeyUpdate,
@@ -285,6 +286,7 @@ def _config_table(prisma_client: PrismaClient) -> _ConfigTableActions:
 class _CustomKeyHooksModule(Protocol):
     user_custom_key_generate: Callable[..., Awaitable[Mapping[str, object]]] | None
     user_custom_key_update: Callable[..., Awaitable[Mapping[str, object]]] | None
+    user_custom_key_policy: Callable[..., Awaitable[Mapping[str, object]]] | None
 
 
 def _custom_key_generate_hook(
@@ -299,6 +301,161 @@ def _custom_key_update_hook(
     return hooks.user_custom_key_update
 
 
+def _custom_key_policy_hook(
+    hooks: _CustomKeyHooksModule,
+) -> Callable[..., Awaitable[Mapping[str, object]]] | None:
+    return hooks.user_custom_key_policy
+
+
+async def _enforce_custom_key_update_policy(
+    hook: Callable[..., Awaitable[Mapping[str, object]]] | None,
+    data: UpdateKeyRequest,
+) -> None:
+    if hook is None:
+        return
+    if not inspect.iscoroutinefunction(hook):
+        raise ValueError("user_custom_key_update must be a coroutine")
+    result: Final = await hook(data)
+    if not result.get("decision", True):
+        raise HTTPException(
+            status_code=status.HTTP_403_FORBIDDEN,
+            detail=result.get("message", "Authentication Failed - Custom Auth Rule"),
+        )
+
+
+async def _enforce_custom_key_policy(
+    hook: Callable[..., Awaitable[Mapping[str, object]]] | None,
+    build_policy_request: Callable[[], CustomKeyPolicyRequest],
+) -> None:
+    if hook is None:
+        return
+    if not inspect.iscoroutinefunction(hook):
+        raise ValueError("user_custom_key_policy must be a coroutine")
+    result: Final = await hook(build_policy_request())
+    if not result.get("decision", True):
+        raise HTTPException(
+            status_code=status.HTTP_403_FORBIDDEN,
+            detail=result.get("message", "Authentication Failed - Custom Auth Rule"),
+        )
+
+
+_KEY_UPDATE_JSON_STRING_COLUMNS: Final = frozenset({"router_settings", "budget_limits"})
+
+_KEY_METADATA_REQUEST_FIELDS: Final = frozenset(
+    (*LiteLLM_ManagementEndpoint_MetadataFields_Premium, *LiteLLM_ManagementEndpoint_MetadataFields)
+)
+
+
+def _decode_json_string_column(column: str, value: object) -> object:
+    if column in _KEY_UPDATE_JSON_STRING_COLUMNS and isinstance(value, str):
+        return json.loads(value)
+    return value
+
+
+def _verification_token_from_row(row: Mapping[str, object]) -> LiteLLM_VerificationToken:
+    org_id: Final = row["organization_id"] if "organization_id" in row else row.get("org_id")
+    return LiteLLM_VerificationToken.model_validate(MappingProxyType({**row, "org_id": org_id}))
+
+
+def _effective_key_after_update(
+    existing_key_row: LiteLLM_VerificationToken,
+    non_default_values: Mapping[str, object],
+) -> LiteLLM_VerificationToken:
+    overlay: Final = MappingProxyType(
+        {column: _decode_json_string_column(column, value) for column, value in non_default_values.items()}
+    )
+    return _verification_token_from_row(
+        MappingProxyType({**existing_key_row.model_dump(), **overlay, "object_permission": None})
+    )
+
+
+def _update_policy_request(
+    operation: Literal["update", "regenerate"],
+    existing_key_row: LiteLLM_VerificationToken,
+    non_default_values: Mapping[str, object],
+    request: UpdateKeyRequest | RegenerateKeyRequest,
+) -> CustomKeyPolicyRequest:
+    return CustomKeyPolicyRequest(
+        operation=operation,
+        existing_key=_verification_token_from_row(existing_key_row.model_dump()),
+        effective_key=_effective_key_after_update(
+            existing_key_row=existing_key_row, non_default_values=non_default_values
+        ),
+        request=request,
+    )
+
+
+def _generate_budget_windows(
+    budget_limits: Sequence[BudgetLimitEntry] | None,
+) -> tuple[Mapping[str, object], ...] | None:
+    if not budget_limits:
+        return None
+    return tuple(
+        MappingProxyType(
+            {
+                **window.model_dump(),
+                "reset_at": get_budget_reset_time(budget_duration=window.budget_duration).isoformat(),
+            }
+        )
+        for window in budget_limits
+    )
+
+
+def _effective_key_for_generate(data: GenerateKeyRequest, now: datetime) -> LiteLLM_VerificationToken:
+    requested: Final = data.model_dump(exclude_unset=True, exclude_none=True)
+    metadata_fields: Final = MappingProxyType(
+        {field: value for field, value in requested.items() if field in _KEY_METADATA_REQUEST_FIELDS}
+    )
+    column_fields: Final = MappingProxyType(
+        {field: value for field, value in requested.items() if field not in _KEY_METADATA_REQUEST_FIELDS}
+    )
+    metadata: Final = data.metadata or MappingProxyType({})
+    folded_metadata: Final = {**metadata, **metadata_fields}  # mutable-ok: encrypt_callback_vars needs a dict
+    columns: Final = handle_key_type(data, {**column_fields})  # mutable-ok: handle_key_type mutates in place
+    expires: Final = (
+        now + timedelta(seconds=duration_in_seconds(duration=data.duration)) if data.duration is not None else None
+    )
+    budget_reset_at: Final = (
+        get_budget_reset_time(budget_duration=data.budget_duration) if data.budget_duration is not None else None
+    )
+    key_rotation_at: Final = (
+        now + timedelta(seconds=duration_in_seconds(duration=data.rotation_interval))
+        if data.auto_rotate and data.rotation_interval
+        else None
+    )
+    return _verification_token_from_row(
+        MappingProxyType(
+            {
+                **columns,
+                "metadata": encrypt_callback_vars(folded_metadata),
+                "expires": expires,
+                "budget_reset_at": budget_reset_at,
+                "key_rotation_at": key_rotation_at,
+                "budget_limits": _generate_budget_windows(data.budget_limits),
+                "object_permission": None,
+            }
+        )
+    )
+
+
+_EMPTY_DURATION_MEANS_UNCHANGED: Final = frozenset({"duration", "budget_duration"})
+
+
+def _regenerate_request_as_update_request(key: str, data: RegenerateKeyRequest) -> UpdateKeyRequest | None:
+    changed_fields: Final = MappingProxyType(
+        {
+            field: value
+            for field, value in data.model_dump(exclude_unset=True).items()
+            if field in UpdateKeyRequest.model_fields
+            and field != "key"
+            and not (field in _EMPTY_DURATION_MEANS_UNCHANGED and value == "")
+        }
+    )
+    if not changed_fields:
+        return None
+    return UpdateKeyRequest(key=key, **changed_fields)
+
+
 class _LegacyDumpable(Protocol):
     def dict(self) -> Mapping[str, object]: ...
 
@@ -992,6 +1149,7 @@ async def _common_key_generation_helper(
     litellm_changed_by: str | None,
     team_table: LiteLLM_TeamTableCachedObj | None,
 ) -> GenerateKeyResponse:
+    from litellm.proxy import proxy_server
     from litellm.proxy.proxy_server import (
         litellm_proxy_admin_name,
         llm_router,
@@ -1140,6 +1298,16 @@ async def _common_key_generation_helper(
             "litellm.proxy.proxy_server.generate_key_fn(): Enterprise key management params not applied - %s", e
         )
 
+    await _enforce_custom_key_policy(
+        hook=_custom_key_policy_hook(proxy_server),
+        build_policy_request=lambda: CustomKeyPolicyRequest(
+            operation="generate",
+            existing_key=None,
+            effective_key=_effective_key_for_generate(data=data, now=datetime.now(timezone.utc)),
+            request=data,
+        ),
+    )
+
     # TODO: @ishaan-jaff: Migrate all budget tracking to use LiteLLM_BudgetTable
     _budget_id = data.budget_id
     if prisma_client is not None and data.soft_budget is not None:
@@ -2325,12 +2493,6 @@ async def prepare_key_update_data(
             # sentinel for Json? columns, so store the JSON literal null
             non_default_values["budget_limits"] = json.dumps(None)
 
-    if "object_permission" in non_default_values:
-        non_default_values = await _handle_update_object_permission(
-            data_json=non_default_values,
-            existing_key_row=existing_key_row,
-        )
-
     _metadata: Final = existing_key_row.metadata or {}
 
     # validate model_max_budget
@@ -2351,13 +2513,12 @@ async def prepare_key_update_data(
 async def _handle_update_object_permission(
     data_json: dict,
     existing_key_row: LiteLLM_VerificationToken,
+    prisma_client: PrismaClient,
 ) -> dict:
-    """
-    Handle the update of object permission.
-    """
-    from litellm.proxy.proxy_server import prisma_client
+    """Persist the requested object permission row and swap it for its id, only after the key policy allowed the write."""
+    if "object_permission" not in data_json:
+        return data_json
 
-    # Use the common helper to handle the object permission update
     object_permission_id: Final = await handle_update_object_permission_common(
         data_json=data_json,
         existing_object_permission_id=existing_key_row.object_permission_id,
@@ -2491,6 +2652,7 @@ async def _process_single_key_update(
     llm_router: Router | None,
     user_custom_key_update: Callable | None = None,
     existing_key_row: LiteLLM_VerificationToken | None = None,
+    user_custom_key_policy: Callable[..., Awaitable[Mapping[str, object]]] | None = None,
 ) -> dict[str, object]:
     """
     Process a single key update with all validations and checks.
@@ -2603,6 +2765,16 @@ async def _process_single_key_update(
         data=update_key_request, existing_key_row=existing_key_row, prisma_client=prisma_client, llm_router=llm_router
     )
 
+    await _enforce_custom_key_policy(
+        hook=user_custom_key_policy,
+        build_policy_request=lambda: _update_policy_request(
+            operation="update",
+            existing_key_row=existing_key_row,
+            non_default_values=non_default_values,
+            request=update_key_request,
+        ),
+    )
+
     # Update key in database
     if prisma_client is None:
         raise HTTPException(
@@ -2610,7 +2782,12 @@ async def _process_single_key_update(
             detail={"error": "Database not connected"},
         )
 
-    _data: Final = {**non_default_values, "token": update_key_request.key}
+    update_values: Final = await _handle_update_object_permission(
+        data_json=non_default_values,
+        existing_key_row=existing_key_row,
+        prisma_client=prisma_client,
+    )
+    _data: Final = {**update_values, "token": update_key_request.key}
     response: Final[Mapping[str, object] | None] = cast(  # cast-ok: every update_data branch returns a str-keyed dict
         "Mapping[str, object] | None",
         await prisma_client.update_data(token=update_key_request.key, data=_data),
@@ -3103,19 +3280,7 @@ async def update_key_fn(
             user_api_key_cache=user_api_key_cache,
         )
 
-        # Custom key update hook
-        custom_key_update_hook: Final[Callable[..., Awaitable[Mapping[str, object]]] | None] = _custom_key_update_hook(
-            proxy_server
-        )
-        if custom_key_update_hook is not None:
-            if inspect.iscoroutinefunction(custom_key_update_hook):
-                result: Final = await custom_key_update_hook(data)
-            else:
-                raise ValueError("user_custom_key_update must be a coroutine")
-            decision: Final = result.get("decision", True)
-            message: Final = result.get("message", "Authentication Failed - Custom Auth Rule")
-            if not decision:
-                raise HTTPException(status_code=status.HTTP_403_FORBIDDEN, detail=message)
+        await _enforce_custom_key_update_policy(hook=_custom_key_update_hook(proxy_server), data=data)
 
         # Enforce upperbound key params on update (don't fill defaults)
         _enforce_upperbound_key_params(data, fill_defaults=False)
@@ -3142,21 +3307,36 @@ async def update_key_fn(
             existing_key_alias=existing_key_row.key_alias,
         )
 
+        await _enforce_custom_key_policy(
+            hook=_custom_key_policy_hook(proxy_server),
+            build_policy_request=lambda: _update_policy_request(
+                operation="update",
+                existing_key_row=existing_key_row,
+                non_default_values=non_default_values,
+                request=data,
+            ),
+        )
+
         if prisma_client is None:
             raise Exception("Not connected to DB!")
 
+        update_values: Final = await _handle_update_object_permission(
+            data_json=non_default_values,
+            existing_key_row=existing_key_row,
+            prisma_client=prisma_client,
+        )
         changed_by: Final = user_api_key_dict.user_id or litellm_proxy_admin_name
         response: Final = (
             await _update_key_row_with_soft_budget(
                 prisma_client=prisma_client,
                 key=key,
                 data=data,
-                non_default_values=non_default_values,
+                non_default_values=update_values,
                 existing_key_row=existing_key_row,
                 changed_by=changed_by,
             )
             if "soft_budget" in data.model_fields_set
-            else await prisma_client.update_data(token=key, data=MappingProxyType({**non_default_values, "token": key}))
+            else await prisma_client.update_data(token=key, data=MappingProxyType({**update_values, "token": key}))
         )
 
         # Delete - key from cache, since it's been updated!
@@ -3291,6 +3471,7 @@ async def bulk_update_keys(
     )
 
     custom_key_update_hook: Final = _custom_key_update_hook(proxy_server)
+    custom_key_policy_hook: Final = _custom_key_policy_hook(proxy_server)
 
     if user_api_key_dict.user_role != LitellmUserRoles.PROXY_ADMIN.value:
         raise HTTPException(
@@ -3338,6 +3519,7 @@ async def bulk_update_keys(
                 proxy_logging_obj=proxy_logging_obj,
                 llm_router=llm_router,
                 user_custom_key_update=custom_key_update_hook,
+                user_custom_key_policy=custom_key_policy_hook,
             )
 
             successful_updates.append(
@@ -3455,6 +3637,7 @@ async def bulk_update_team_keys(
     )
 
     custom_key_update_hook: Final = _custom_key_update_hook(proxy_server)
+    custom_key_policy_hook: Final = _custom_key_policy_hook(proxy_server)
 
     if prisma_client is None:
         raise HTTPException(
@@ -3585,6 +3768,7 @@ async def bulk_update_team_keys(
                 proxy_logging_obj=proxy_logging_obj,
                 llm_router=llm_router,
                 user_custom_key_update=custom_key_update_hook,
+                user_custom_key_policy=custom_key_policy_hook,
                 existing_key_row=existing_by_token[db_token],
             )
 
@@ -5118,6 +5302,7 @@ async def _execute_virtual_key_regeneration(
     proxy_logging_obj: ProxyLogging,
 ) -> GenerateKeyResponse:
     """Generate new token, update DB, invalidate cache, and return response."""
+    from litellm.proxy import proxy_server
     from litellm.proxy.proxy_server import hash_token
 
     # Mirror the /key/update ownership rebind guard. See helper docstring.
@@ -5165,6 +5350,9 @@ async def _execute_virtual_key_regeneration(
 
     non_default_values = {}
     if data is not None:
+        update_request: Final = _regenerate_request_as_update_request(key=hashed_api_key, data=data)
+        if update_request is not None:
+            await _enforce_custom_key_update_policy(hook=_custom_key_update_hook(proxy_server), data=update_request)
         # Enforce upperbound key params on regenerate (don't fill defaults)
         _enforce_upperbound_key_params(data, fill_defaults=False)
         non_default_values = await prepare_key_update_data(
@@ -5175,7 +5363,21 @@ async def _execute_virtual_key_regeneration(
         if new_key_alias != key_in_db.key_alias:
             _validate_key_alias_format(key_alias=new_key_alias)
         verbose_proxy_logger.debug("non_default_values: %s", non_default_values)
-    update_data.update(non_default_values)
+    await _enforce_custom_key_policy(
+        hook=_custom_key_policy_hook(proxy_server),
+        build_policy_request=lambda: _update_policy_request(
+            operation="regenerate",
+            existing_key_row=key_in_db,
+            non_default_values=non_default_values,
+            request=data if data is not None else RegenerateKeyRequest(),
+        ),
+    )
+    update_values: Final = await _handle_update_object_permission(
+        data_json=non_default_values,
+        existing_key_row=key_in_db,
+        prisma_client=prisma_client,
+    )
+    update_data.update(update_values)
     jsonified_update_data: Final[Mapping[str, object]] = prisma_client.jsonify_object(data=update_data)
 
     # Snapshot before the token update: the FK cascade rewrites mapping rows to the new hash,
@@ -5185,6 +5387,13 @@ async def _execute_virtual_key_regeneration(
         prisma_client=prisma_client,
     )
 
+    await _persist_deleted_verification_tokens(
+        keys=[key_in_db],
+        prisma_client=prisma_client,
+        user_api_key_dict=user_api_key_dict,
+        litellm_changed_by=litellm_changed_by,
+    )
+
     # If grace period set, insert deprecated key so old key remains valid
     await _insert_deprecated_key(
         prisma_client=prisma_client,
@@ -5484,17 +5693,6 @@ async def regenerate_key_fn(
         if litellm_changed_by is not None and not isinstance(litellm_changed_by, str):
             litellm_changed_by = None
 
-        # Save the old key record to deleted table before regeneration.
-        # This preserves key_alias and team_id metadata for historical spend records.
-        # If this fails, abort the regeneration to avoid permanently losing the
-        # old hash→metadata mapping.
-        await _persist_deleted_verification_tokens(
-            keys=[_key_in_db],
-            prisma_client=prisma_client,
-            user_api_key_dict=user_api_key_dict,
-            litellm_changed_by=litellm_changed_by,
-        )
-
         return await _execute_virtual_key_regeneration(
             prisma_client=prisma_client,
             llm_router=llm_router,
diff --git a/litellm/proxy/pass_through_endpoints/llm_provider_handlers/vertex_ai_live_passthrough_logging_handler.py b/litellm/proxy/pass_through_endpoints/llm_provider_handlers/vertex_ai_live_passthrough_logging_handler.py
index e26f5f57532..0ff02b29c58 100644
--- a/litellm/proxy/pass_through_endpoints/llm_provider_handlers/vertex_ai_live_passthrough_logging_handler.py
+++ b/litellm/proxy/pass_through_endpoints/llm_provider_handlers/vertex_ai_live_passthrough_logging_handler.py
@@ -5,18 +5,105 @@ Handles cost tracking and logging for Vertex AI Live API WebSocket passthrough e
 Supports different modalities: text, audio, video, and web search.
 """
 
+from collections.abc import Mapping, Sequence
 from datetime import datetime
-from typing import Any, Final
+from itertools import chain, pairwise
+from types import MappingProxyType
+from typing import Final, Literal, TypeAlias
 
 from litellm._logging import verbose_proxy_logger
+from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
+from litellm.llms.vertex_ai.gemini.grounding_requests import GroundingRequests, calculate_grounding_requests
 from litellm.proxy.pass_through_endpoints.llm_provider_handlers.base_passthrough_logging_handler import (
     BasePassthroughLoggingHandler,
 )
 from litellm.proxy.pass_through_endpoints.llm_provider_handlers.openai_passthrough_logging_handler import (
     PassThroughEndpointLoggingTypedDict,
 )
-from litellm.types.utils import LlmProviders, ModelResponse, Usage
-from litellm.utils import get_model_info
+from litellm.types.utils import (
+    CompletionTokensDetailsWrapper,
+    CostBreakdown,
+    LlmProviders,
+    ModelResponse,
+    PromptTokensDetailsWrapper,
+    Usage,
+)
+
+_NO_GROUNDING: Final = GroundingRequests(web_search_requests=None, google_maps_grounding_requests=None)
+
+_AGGREGATED_FIELDS: Final = frozenset(
+    {
+        "promptTokenCount",
+        "candidatesTokenCount",
+        "totalTokenCount",
+        "toolUsePromptTokenCount",
+        "promptTokensDetails",
+        "candidatesTokensDetails",
+    }
+)
+
+
+def _detail_entries(raw: object) -> tuple[Mapping[str, object], ...]:
+    """Narrow one turn's ``*TokensDetails`` value to the entries that are actually shaped like one."""
+    return tuple(entry for entry in raw if isinstance(entry, Mapping)) if isinstance(raw, Sequence) else ()
+
+
+def _grounding_metadata(websocket_messages: Sequence[object]) -> tuple[Mapping[str, object], ...]:
+    """Collect every ``serverContent.groundingMetadata`` a session emitted.
+
+    Live reports grounding in the server frames, never in ``usageMetadata``, so the per-query
+    charge has to be counted here rather than derived from the token totals.
+    """
+    return tuple(
+        metadata
+        for message in websocket_messages
+        if isinstance(message, Mapping)
+        for server_content in (message.get("serverContent"),)
+        if isinstance(server_content, Mapping)
+        for metadata in (server_content.get("groundingMetadata"),)
+        if isinstance(metadata, Mapping)
+    )
+
+
+def _turns(websocket_messages: Sequence[object]) -> tuple[tuple[object, ...], ...]:
+    """Split a session at every ``usageMetadata`` frame; frames after the last one never got their usage."""
+    closes: Final = tuple(
+        index + 1
+        for index, message in enumerate(websocket_messages)
+        if isinstance(message, Mapping) and isinstance(message.get("usageMetadata"), dict)
+    )
+    return tuple(tuple(websocket_messages[start:end]) for start, end in pairwise((0, *closes)))
+
+
+def _session_grounding_requests(websocket_messages: Sequence[object]) -> GroundingRequests:
+    per_turn: Final = tuple(
+        calculate_grounding_requests(_grounding_metadata(turn)) for turn in _turns(websocket_messages)
+    )
+    web_search_requests: Final = sum(requests.web_search_requests or 0 for requests in per_turn)
+    google_maps_grounding_requests: Final = sum(requests.google_maps_grounding_requests or 0 for requests in per_turn)
+    return GroundingRequests(
+        web_search_requests=web_search_requests or None,
+        google_maps_grounding_requests=google_maps_grounding_requests or None,
+    )
+
+
+_SummedField: TypeAlias = Literal[
+    "input_cost",
+    "output_cost",
+    "tool_usage_cost",
+    "cache_read_cost",
+    "cache_creation_cost",
+    "reasoning_cost",
+    "original_cost",
+    "discount_amount",
+    "margin_fixed_amount",
+    "margin_total_amount",
+]
+
+
+def _summed(breakdowns: Sequence[CostBreakdown], field: _SummedField) -> float | None:
+    values: Final = tuple(value for breakdown in breakdowns if (value := breakdown.get(field)) is not None)
+    return sum(values) if values else None
 
 
 class VertexAILivePassthroughLoggingHandler(BasePassthroughLoggingHandler):
@@ -48,186 +135,110 @@ class VertexAILivePassthroughLoggingHandler(BasePassthroughLoggingHandler):
         """Return the LLM provider name."""
         return LlmProviders.VERTEX_AI
 
+    @staticmethod
+    def _resolve_detail_counts(
+        details: Sequence[Mapping[str, object]],
+        declared_total: object,
+    ) -> tuple[tuple[str, int], ...]:
+        """
+        Pair each of one turn's ``*TokensDetails`` entries with its token count.
+
+        Live sometimes names the modality that carries the rest of a turn without a
+        ``tokenCount``, and reading the absent key as zero drops those tokens from the
+        breakdown, so real audio ends up priced as text. A lone unpriced entry therefore takes
+        whatever the turn's declared count leaves over. Two or more cannot be told apart, so
+        they are left out and the cost calculator charges the remainder as text.
+        """
+        priced: Final = tuple(
+            (str(detail.get("modality", "TEXT")), count)
+            for detail in details
+            if isinstance(count := detail.get("tokenCount"), int)
+        )
+        unpriced: Final = tuple(
+            str(detail.get("modality", "TEXT")) for detail in details if not isinstance(detail.get("tokenCount"), int)
+        )
+        if len(unpriced) != 1 or not isinstance(declared_total, int):
+            return priced
+        residual: Final = declared_total - sum(count for _, count in priced)
+        return priced if residual <= 0 else (*priced, (unpriced[0], residual))
+
+    @staticmethod
+    def _sum_by_modality(counts: Sequence[tuple[str, int]]) -> Mapping[str, int]:
+        """Total the (modality, tokenCount) pairs of one or more turns per modality."""
+        return MappingProxyType({modality: sum(c for m, c in counts if m == modality) for modality, _ in counts})
+
+    @staticmethod
+    def _merged_modality_totals(
+        snapshots: Sequence[Mapping[str, object]],
+        count_key: str,
+        details_key: str,
+    ) -> Mapping[str, int]:
+        """Total every turn's per-modality counts, so the breakdown adds up the way the totals do."""
+        return VertexAILivePassthroughLoggingHandler._sum_by_modality(
+            tuple(
+                chain.from_iterable(
+                    VertexAILivePassthroughLoggingHandler._resolve_detail_counts(
+                        _detail_entries(snapshot.get(details_key)), snapshot.get(count_key)
+                    )
+                    for snapshot in snapshots
+                )
+            )
+        )
+
     @staticmethod
     def _extract_usage_metadata_from_websocket_messages(
-        websocket_messages: list[dict],
+        websocket_messages: Sequence[object],
     ) -> dict | None:
         """
         Extract and aggregate usage metadata from a list of WebSocket messages.
 
+        Live emits one ``usageMetadata`` per turn and Google charges per turn for every token in
+        the session context window, which is the current turn's tokens plus all accumulated
+        tokens from previous turns, so the turns add up rather than restating each other. See
+        the Live API note under https://cloud.google.com/vertex-ai/generative-ai/pricing.
+
         Args:
             websocket_messages: List of WebSocket messages from the Live API
 
         Returns:
             Dictionary containing aggregated usage metadata, or None if not found
         """
-        all_usage_metadata: Final = []
+        snapshots: Final = tuple(
+            metadata
+            for message in websocket_messages
+            if isinstance(message, Mapping)
+            for metadata in (message.get("usageMetadata"),)
+            if isinstance(metadata, dict)
+        )
 
-        # Collect all usage metadata messages
-        for message in websocket_messages:
-            if isinstance(message, dict) and "usageMetadata" in message:
-                all_usage_metadata.append(message["usageMetadata"])
-
-        if not all_usage_metadata:
+        if not snapshots:
             return None
 
-        # If only one usage metadata, return it as-is
-        if len(all_usage_metadata) == 1:
-            return all_usage_metadata[0]
-
-        # Aggregate multiple usage metadata messages
-        aggregated: Final[dict[str, Any]] = {
-            "promptTokenCount": 0,
-            "candidatesTokenCount": 0,
-            "totalTokenCount": 0,
-            "promptTokensDetails": [],
-            "candidatesTokensDetails": [],
+        prompt_totals: Final = VertexAILivePassthroughLoggingHandler._merged_modality_totals(
+            snapshots, "promptTokenCount", "promptTokensDetails"
+        )
+        candidate_totals: Final = VertexAILivePassthroughLoggingHandler._merged_modality_totals(
+            snapshots, "candidatesTokenCount", "candidatesTokensDetails"
+        )
+        return {
+            **{key: value for key, value in snapshots[0].items() if key not in _AGGREGATED_FIELDS},
+            "promptTokenCount": sum(snapshot.get("promptTokenCount", 0) for snapshot in snapshots),
+            "candidatesTokenCount": sum(snapshot.get("candidatesTokenCount", 0) for snapshot in snapshots),
+            "totalTokenCount": sum(snapshot.get("totalTokenCount", 0) for snapshot in snapshots),
+            "toolUsePromptTokenCount": sum(snapshot.get("toolUsePromptTokenCount", 0) for snapshot in snapshots),
+            "promptTokensDetails": [
+                {"modality": modality, "tokenCount": count} for modality, count in prompt_totals.items() if count > 0
+            ],
+            "candidatesTokensDetails": [
+                {"modality": modality, "tokenCount": count} for modality, count in candidate_totals.items() if count > 0
+            ],
         }
 
-        # Aggregate token counts
-        for usage in all_usage_metadata:
-            aggregated["promptTokenCount"] += usage.get("promptTokenCount", 0)
-            aggregated["candidatesTokenCount"] += usage.get("candidatesTokenCount", 0)
-            aggregated["totalTokenCount"] += usage.get("totalTokenCount", 0)
-
-        # Aggregate token details by modality
-        modality_totals: Final = {}
-
-        for usage in all_usage_metadata:
-            # Process prompt tokens details
-            for detail in usage.get("promptTokensDetails", []):
-                modality = detail.get("modality", "TEXT")
-                token_count = detail.get("tokenCount", 0)
-
-                if modality not in modality_totals:
-                    modality_totals[modality] = {"prompt": 0, "candidate": 0}
-                modality_totals[modality]["prompt"] += token_count
-
-            # Process candidate tokens details
-            for detail in usage.get("candidatesTokensDetails", []):
-                modality = detail.get("modality", "TEXT")
-                token_count = detail.get("tokenCount", 0)
-
-                if modality not in modality_totals:
-                    modality_totals[modality] = {"prompt": 0, "candidate": 0}
-                modality_totals[modality]["candidate"] += token_count
-
-        # Convert aggregated modality totals back to details format
-        for modality, totals in modality_totals.items():
-            if totals["prompt"] > 0:
-                aggregated["promptTokensDetails"].append({"modality": modality, "tokenCount": totals["prompt"]})
-            if totals["candidate"] > 0:
-                aggregated["candidatesTokensDetails"].append({"modality": modality, "tokenCount": totals["candidate"]})
-
-        # Add any additional fields from the first usage metadata
-        first_usage: Final = all_usage_metadata[0]
-        for key, value in first_usage.items():
-            if key not in aggregated:
-                aggregated[key] = value
-
-        return aggregated
-
-    @staticmethod
-    def _calculate_live_api_cost(
-        model: str,
-        usage_metadata: dict,
-        custom_llm_provider: str = "vertex_ai",
-    ) -> float:
-        """
-        Calculate cost for Vertex AI Live API based on usage metadata.
-
-        Args:
-            model: The model name (e.g., "gemini-2.0-flash-live-preview-04-09")
-            usage_metadata: Usage metadata from the Live API response
-            custom_llm_provider: The LLM provider (default: "vertex_ai")
-
-        Returns:
-            Total cost in USD
-        """
-        try:
-            # Get model pricing information
-            model_info: Final = get_model_info(model=model, custom_llm_provider=custom_llm_provider)
-
-            verbose_proxy_logger.debug("Vertex AI Live API model info for '%s': %s", model, model_info)
-
-            # Check if pricing info is available
-            if not model_info or not model_info.get("input_cost_per_token"):
-                verbose_proxy_logger.error("No pricing info found for %s in local model pricing database", model)
-                return 0.0
-
-            total_cost = 0.0
-
-            # Extract token counts from usage metadata
-            prompt_token_count: Final = usage_metadata.get("promptTokenCount", 0)
-            candidates_token_count: Final = usage_metadata.get("candidatesTokenCount", 0)
-
-            # Calculate base text token costs
-            input_cost_per_token: Final = model_info.get("input_cost_per_token", 0.0)
-            output_cost_per_token: Final = model_info.get("output_cost_per_token", 0.0)
-
-            total_cost += prompt_token_count * input_cost_per_token
-            total_cost += candidates_token_count * output_cost_per_token
-
-            # Handle modality-specific costs if present
-            prompt_tokens_details: Final = usage_metadata.get("promptTokensDetails", [])
-            candidates_tokens_details: Final = usage_metadata.get("candidatesTokensDetails", [])
-
-            # Process prompt tokens by modality
-            for detail in prompt_tokens_details:
-                modality = detail.get("modality", "TEXT")
-                token_count = detail.get("tokenCount", 0)
-
-                if modality == "AUDIO":
-                    audio_cost_per_token = model_info.get("input_cost_per_audio_token", 0.0)
-                    total_cost += token_count * audio_cost_per_token
-                elif modality == "VIDEO":
-                    # Video tokens are typically per second, but we'll treat as per token for now
-                    video_cost_per_token = model_info.get("input_cost_per_video_per_second", 0.0)
-                    total_cost += token_count * video_cost_per_token
-                # TEXT tokens are already handled above
-
-            # Process candidate tokens by modality
-            for detail in candidates_tokens_details:
-                modality = detail.get("modality", "TEXT")
-                token_count = detail.get("tokenCount", 0)
-
-                if modality == "AUDIO":
-                    audio_cost_per_token = model_info.get("output_cost_per_audio_token", 0.0)
-                    total_cost += token_count * audio_cost_per_token
-                elif modality == "VIDEO":
-                    # Video tokens are typically per second, but we'll treat as per token for now
-                    video_cost_per_token = model_info.get("output_cost_per_video_per_second", 0.0)
-                    total_cost += token_count * video_cost_per_token
-                # TEXT tokens are already handled above
-
-            # Handle web search costs if present
-            tool_use_prompt_token_count: Final = usage_metadata.get("toolUsePromptTokenCount", 0)
-            if tool_use_prompt_token_count > 0:
-                # Web search typically has a fixed cost per request
-                web_search_cost: Final = model_info.get("web_search_cost_per_request", 0.0)
-                if isinstance(web_search_cost, (int, float)) and web_search_cost > 0:
-                    total_cost += web_search_cost
-                else:
-                    # Fallback to token-based pricing for tool use
-                    total_cost += tool_use_prompt_token_count * input_cost_per_token
-
-            verbose_proxy_logger.debug(
-                f"Vertex AI Live API cost calculation - Model: {model}, "
-                f"Prompt tokens: {prompt_token_count}, "
-                f"Candidate tokens: {candidates_token_count}, "
-                f"Total cost: ${total_cost:.6f}"
-            )
-
-            return total_cost
-
-        except Exception as e:
-            verbose_proxy_logger.error("Error calculating Vertex AI Live API cost: %s", e)
-            return 0.0
-
     @staticmethod
     def _create_usage_object_from_metadata(
         usage_metadata: dict,
         model: str,
+        grounding_requests: GroundingRequests = _NO_GROUNDING,
     ) -> Usage:
         """
         Create a LiteLLM Usage object from Live API usage metadata.
@@ -235,48 +246,124 @@ class VertexAILivePassthroughLoggingHandler(BasePassthroughLoggingHandler):
         Args:
             usage_metadata: Usage metadata from the Live API response
             model: The model name
+            grounding_requests: The Search and Maps grounding requests summed over the session's
+                turns, matching the per-turn charge
 
         Returns:
             LiteLLM Usage object
         """
-        prompt_tokens: Final = usage_metadata.get("promptTokenCount", 0)
-        completion_tokens: Final = usage_metadata.get("candidatesTokenCount", 0)
-        total_tokens: Final = usage_metadata.get("totalTokenCount", 0)
+        prompt_by_modality: Final = VertexAILivePassthroughLoggingHandler._sum_by_modality(
+            VertexAILivePassthroughLoggingHandler._resolve_detail_counts(
+                _detail_entries(usage_metadata.get("promptTokensDetails")), usage_metadata.get("promptTokenCount")
+            )
+        )
+        candidates_by_modality: Final = VertexAILivePassthroughLoggingHandler._sum_by_modality(
+            VertexAILivePassthroughLoggingHandler._resolve_detail_counts(
+                _detail_entries(usage_metadata.get("candidatesTokensDetails")),
+                usage_metadata.get("candidatesTokenCount"),
+            )
+        )
 
-        # Create modality-specific token details if available
-        prompt_tokens_details: Final = usage_metadata.get("promptTokensDetails", [])
-        candidates_tokens_details: Final = usage_metadata.get("candidatesTokensDetails", [])
-
-        # Extract text tokens from details
-        text_prompt_tokens = 0
-        text_completion_tokens = 0
-
-        for detail in prompt_tokens_details:
-            if detail.get("modality") == "TEXT":
-                text_prompt_tokens = detail.get("tokenCount", 0)
-                break
-
-        for detail in candidates_tokens_details:
-            if detail.get("modality") == "TEXT":
-                text_completion_tokens = detail.get("tokenCount", 0)
-                break
-
-        # If no text tokens found in details, use total counts
-        if text_prompt_tokens == 0:
-            text_prompt_tokens = prompt_tokens
-        if text_completion_tokens == 0:
-            text_completion_tokens = completion_tokens
+        prompt_tokens: Final = usage_metadata.get("promptTokenCount", 0) or sum(prompt_by_modality.values())
+        completion_tokens: Final = usage_metadata.get("candidatesTokenCount", 0) or sum(candidates_by_modality.values())
 
         return Usage(
-            prompt_tokens=text_prompt_tokens,
-            completion_tokens=text_completion_tokens,
-            total_tokens=total_tokens,
+            prompt_tokens=prompt_tokens,
+            completion_tokens=completion_tokens,
+            total_tokens=usage_metadata.get("totalTokenCount", 0) or (prompt_tokens + completion_tokens),
+            prompt_tokens_details=PromptTokensDetailsWrapper(
+                text_tokens=prompt_by_modality.get("TEXT"),
+                audio_tokens=prompt_by_modality.get("AUDIO"),
+                image_tokens=prompt_by_modality.get("IMAGE"),
+                video_tokens=prompt_by_modality.get("VIDEO"),
+                tool_use_tokens=usage_metadata.get("toolUsePromptTokenCount") or None,
+                web_search_requests=grounding_requests.web_search_requests,
+                google_maps_grounding_requests=grounding_requests.google_maps_grounding_requests,
+            ),
+            completion_tokens_details=CompletionTokensDetailsWrapper(
+                text_tokens=candidates_by_modality.get("TEXT"),
+                audio_tokens=candidates_by_modality.get("AUDIO"),
+                image_tokens=candidates_by_modality.get("IMAGE"),
+                video_tokens=candidates_by_modality.get("VIDEO"),
+            ),
         )
 
+    def _session_usage(self, websocket_messages: Sequence[object], model: str) -> Usage | None:
+        usage_metadata: Final = self._extract_usage_metadata_from_websocket_messages(websocket_messages)
+        if usage_metadata is None:
+            return None
+        return self._create_usage_object_from_metadata(
+            usage_metadata=usage_metadata,
+            grounding_requests=_session_grounding_requests(websocket_messages),
+            model=model,
+        )
+
+    def _turn_cost(
+        self,
+        turn: Sequence[object],
+        model: str,
+        logging_obj: LiteLLMLoggingObj,
+    ) -> tuple[float, CostBreakdown] | None:
+        usage: Final = self._session_usage(turn, model)
+        if usage is None:
+            return None
+        cost: Final = logging_obj._response_cost_calculator(  # pyright: ignore[reportPrivateUsage]  # the call's own calculator keeps custom pricing and the deployment's region in step with the spend row
+            result=ModelResponse(model=model, usage=usage),
+            litellm_model_name=model,
+        )
+        if cost is None:
+            return None
+        breakdown: Final = logging_obj.cost_breakdown
+        return None if breakdown is None else (cost, breakdown)
+
+    def _session_cost(
+        self,
+        websocket_messages: Sequence[object],
+        model: str,
+        logging_obj: LiteLLMLoggingObj,
+    ) -> float | None:
+        """Price each turn on its own tokens and grounding, so two grounded turns pay the query fee twice.
+
+        The fixed cost margin is a flat per-request fee, so the session's single spend row carries it once
+        rather than once per turn.
+        """
+        turn_costs: Final = tuple(self._turn_cost(turn, model, logging_obj) for turn in _turns(websocket_messages))
+        priced: Final = tuple(turn_cost for turn_cost in turn_costs if turn_cost is not None)
+        if not priced or len(priced) != len(turn_costs):
+            return None
+        breakdowns: Final = tuple(breakdown for _, breakdown in priced)
+        first: Final = breakdowns[0]
+        fixed_margin: Final = first.get("margin_fixed_amount") or 0.0
+        duplicated_fixed_margin: Final = fixed_margin * (len(priced) - 1)
+        total_cost: Final = sum(cost for cost, _ in priced) - duplicated_fixed_margin
+        summed_margin_total: Final = _summed(breakdowns, "margin_total_amount")
+        margin_total_amount: Final = (
+            None if summed_margin_total is None else summed_margin_total - duplicated_fixed_margin
+        )
+        logging_obj.set_cost_breakdown(
+            input_cost=_summed(breakdowns, "input_cost") or 0.0,
+            output_cost=_summed(breakdowns, "output_cost") or 0.0,
+            total_cost=total_cost,
+            cost_for_built_in_tools_cost_usd_dollar=_summed(breakdowns, "tool_usage_cost") or 0.0,
+            original_cost=_summed(breakdowns, "original_cost"),
+            discount_percent=first.get("discount_percent"),
+            discount_amount=_summed(breakdowns, "discount_amount"),
+            margin_percent=first.get("margin_percent"),
+            margin_fixed_amount=first.get("margin_fixed_amount"),
+            margin_total_amount=margin_total_amount,
+            cache_read_cost=_summed(breakdowns, "cache_read_cost"),
+            cache_creation_cost=_summed(breakdowns, "cache_creation_cost"),
+            reasoning_cost=_summed(breakdowns, "reasoning_cost"),
+            service_tier=first.get("service_tier"),
+            data_residency=first.get("data_residency"),
+            vertex_location=first.get("vertex_location"),
+        )
+        return total_cost
+
     def vertex_ai_live_passthrough_handler(
         self,
-        websocket_messages: list[dict],
-        logging_obj,
+        websocket_messages: Sequence[object],
+        logging_obj: LiteLLMLoggingObj,
         url_route: str,
         start_time: datetime,
         end_time: datetime,
@@ -300,34 +387,25 @@ class VertexAILivePassthroughLoggingHandler(BasePassthroughLoggingHandler):
         """
         try:
             # Extract model from request body or kwargs
-            model: Final = kwargs.get("model", "gemini-2.0-flash-live-preview-04-09")
+            requested_model: Final = kwargs.get("model")
+            model: Final = (
+                requested_model if isinstance(requested_model, str) else "gemini-2.0-flash-live-preview-04-09"
+            )
             custom_llm_provider: Final = kwargs.get("custom_llm_provider", "vertex_ai")
             verbose_proxy_logger.debug(
                 "Vertex AI Live API model: %s, custom_llm_provider: %s", model, custom_llm_provider
             )
 
-            # Extract usage metadata from WebSocket messages
-            usage_metadata: Final = self._extract_usage_metadata_from_websocket_messages(websocket_messages)
+            usage: Final = self._session_usage(websocket_messages, model)
 
-            if not usage_metadata:
+            if usage is None:
                 verbose_proxy_logger.warning("No usage metadata found in Vertex AI Live API WebSocket messages")
                 return {
                     "result": None,
                     "kwargs": kwargs,
                 }
 
-            # Calculate cost using Live API specific pricing
-            response_cost: Final = self._calculate_live_api_cost(
-                model=model,
-                usage_metadata=usage_metadata,
-                custom_llm_provider=custom_llm_provider,
-            )
-
-            # Create Usage object for standard LiteLLM logging
-            usage: Final = self._create_usage_object_from_metadata(
-                usage_metadata=usage_metadata,
-                model=model,
-            )
+            response_cost: Final = self._session_cost(websocket_messages, model, logging_obj)
 
             # Create a mock ModelResponse for standard logging
             litellm_model_response: Final = ModelResponse(
@@ -338,9 +416,9 @@ class VertexAILivePassthroughLoggingHandler(BasePassthroughLoggingHandler):
                 usage=usage,
                 choices=[],
             )
+            if response_cost is not None:
+                litellm_model_response._hidden_params["response_cost"] = response_cost  # pyright: ignore[reportPrivateUsage]  # the logger reads the cost off the response's hidden params; the constructor's hidden_params kwarg is reset by pydantic
 
-            # Update kwargs with cost information
-            kwargs["response_cost"] = response_cost
             kwargs["model"] = model
             kwargs["custom_llm_provider"] = custom_llm_provider
 
@@ -348,12 +426,15 @@ class VertexAILivePassthroughLoggingHandler(BasePassthroughLoggingHandler):
             import re
 
             allowed_pattern: Final = re.compile(r"^[A-Za-z0-9._\-:]+$")
-            safe_model: Final = model if isinstance(model, str) and allowed_pattern.match(model) else "[REDACTED]"
+            safe_model: Final = model if allowed_pattern.match(model) else "[REDACTED]"
             verbose_proxy_logger.debug(
-                f"Vertex AI Live API passthrough cost tracking - "
-                f"Model: {safe_model}, Cost: ${response_cost:.6f}, "
-                f"Prompt tokens: {usage.prompt_tokens}, "
-                f"Completion tokens: {usage.completion_tokens}"
+                "Vertex AI Live API passthrough cost tracking - Model: %s, "
+                "Prompt tokens: %s %s, Completion tokens: %s %s",
+                safe_model,
+                usage.prompt_tokens,
+                usage.prompt_tokens_details,
+                usage.completion_tokens,
+                usage.completion_tokens_details,
             )
 
             return {
diff --git a/litellm/proxy/pass_through_endpoints/pass_through_endpoints.py b/litellm/proxy/pass_through_endpoints/pass_through_endpoints.py
index ea4ede7e513..b66c295d1aa 100644
--- a/litellm/proxy/pass_through_endpoints/pass_through_endpoints.py
+++ b/litellm/proxy/pass_through_endpoints/pass_through_endpoints.py
@@ -2090,6 +2090,22 @@ def _rewrite_vertex_live_setup_model(text_data: str, setup_model_rewriter: Calla
     return json.dumps({**message, "setup": {**setup, "model": rewritten_model}})  # mutable-ok: one-shot json payload
 
 
+def _resolved_vertex_live_setup(
+    setup_data: Mapping[str, object], setup_model_rewriter: Callable[[str], str] | None
+) -> Mapping[str, object]:
+    """
+    Give the model extractor the same fully qualified path the upstream will receive.
+
+    Clients may name a bare gateway alias, which the rewriter turns into a ``projects/...`` path before
+    it reaches Vertex. The extractor only reads a path containing ``/models/``, so running it on the raw
+    frame logs the session as ``unknown`` at no cost, which is precisely the supported client form
+    """
+    setup_model: Final = setup_data.get("model")
+    if setup_model_rewriter is None or not isinstance(setup_model, str):
+        return setup_data
+    return {**setup_data, "model": setup_model_rewriter(setup_model)}
+
+
 def _truncated_close_reason(reason: str) -> str:
     """
     Fit a close reason inside the byte budget a WebSocket close frame allows, without splitting a character
@@ -2314,7 +2330,9 @@ async def websocket_passthrough_request(
                                             setup_data,
                                         )
                                         if isinstance(setup_data, dict) and "model" in setup_data:
-                                            extracted_model = _extract_model_from_vertex_ai_setup(setup_data)
+                                            extracted_model = _extract_model_from_vertex_ai_setup(
+                                                _resolved_vertex_live_setup(setup_data, setup_model_rewriter)
+                                            )
                                             if extracted_model:
                                                 kwargs["model"] = extracted_model
                                                 kwargs["custom_llm_provider"] = "vertex_ai-language-models"
diff --git a/litellm/proxy/proxy_server.py b/litellm/proxy/proxy_server.py
index f81a3166a28..63c62099b25 100644
--- a/litellm/proxy/proxy_server.py
+++ b/litellm/proxy/proxy_server.py
@@ -928,6 +928,7 @@ def cleanup_router_config_variables():
         user_custom_auth_path, \
         user_custom_key_generate, \
         user_custom_key_update, \
+        user_custom_key_policy, \
         user_custom_sso, \
         user_custom_ui_sso_sign_in_handler, \
         use_background_health_checks, \
@@ -945,6 +946,7 @@ def cleanup_router_config_variables():
     user_custom_auth_path = None
     user_custom_key_generate = None
     user_custom_key_update = None
+    user_custom_key_policy = None
     TEAM_METADATA_VALIDATOR_REGISTRY.set(None)
     TEAM_METADATA_SCHEMA_REGISTRY.set(())
     user_custom_sso = None
@@ -2369,6 +2371,7 @@ user_custom_key_generate = None
 _pkce_no_redis_warning_emitted: bool = False
 _cp_no_redis_warning_emitted: bool = False
 user_custom_key_update = None
+user_custom_key_policy = None
 user_custom_sso = None
 user_custom_ui_sso_sign_in_handler = None
 use_background_health_checks = None
@@ -4256,6 +4259,7 @@ _DB_OVERLAY_REMOTE_MODULE_STR_FIELDS: Final[dict[str, tuple[str, ...]]] = {
         "custom_auth",
         "custom_key_generate",
         "custom_key_update",
+        "custom_key_policy",
         "custom_team_metadata_validate",
         "custom_sso",
         "custom_ui_sso_sign_in_handler",
@@ -5405,6 +5409,7 @@ class ProxyConfig:
             user_custom_auth_path, \
             user_custom_key_generate, \
             user_custom_key_update, \
+            user_custom_key_policy, \
             user_custom_sso, \
             user_custom_ui_sso_sign_in_handler, \
             use_background_health_checks, \
@@ -5942,6 +5947,10 @@ class ProxyConfig:
             if custom_key_update is not None:
                 user_custom_key_update = get_instance_fn(value=custom_key_update, config_file_path=config_file_path)
 
+            custom_key_policy: Final = general_settings.get("custom_key_policy", None)
+            if custom_key_policy is not None:
+                user_custom_key_policy = get_instance_fn(value=custom_key_policy, config_file_path=config_file_path)
+
             custom_team_metadata_validate: Final = general_settings.get("custom_team_metadata_validate", None)
             TEAM_METADATA_VALIDATOR_REGISTRY.set(
                 get_instance_fn(value=custom_team_metadata_validate, config_file_path=config_file_path)
diff --git a/litellm/realtime_api/main.py b/litellm/realtime_api/main.py
index 44c47af57f4..d67e4555a29 100644
--- a/litellm/realtime_api/main.py
+++ b/litellm/realtime_api/main.py
@@ -30,6 +30,7 @@ from litellm.types.router import GenericLiteLLMParams
 from litellm.types.utils import CallTypes, LlmProviders
 from litellm.utils import ProviderConfigManager
 
+from ..litellm_core_utils.credential_accessor import CredentialAccessor
 from ..litellm_core_utils.get_litellm_params import get_litellm_params
 from ..litellm_core_utils.litellm_logging import Logging as LiteLLMLogging
 from ..llms.azure.common_utils import get_azure_ad_token
@@ -54,6 +55,17 @@ xai_realtime: Final = XAIRealtime()
 vertex_llm_base: Final = VertexBase()
 base_llm_http_handler = BaseLLMHTTPHandler()
 _EMPTY_MODEL_PARAMS: Final[Mapping[str, Any]] = MappingProxyType({})
+_EMPTY_AUTH_HEADERS: Final[Mapping[str, str]] = MappingProxyType({})
+
+
+def _model_params_with_stored_credentials(model_params: Mapping[str, Any]) -> Mapping[str, Any]:
+    credential_name: Final = model_params.get("litellm_credential_name")
+    credential_values: Final = (
+        CredentialAccessor.get_credential_values(credential_name)
+        if isinstance(credential_name, str)
+        else _EMPTY_MODEL_PARAMS
+    )
+    return MappingProxyType({**credential_values, **model_params})
 
 
 def _with_resolved_session_model(session: dict[str, object], model_name: str) -> dict[str, object]:
@@ -591,13 +603,15 @@ def _azure_realtime_health_protocol(
 
 def _realtime_health_check_auth_headers(
     custom_llm_provider: str, api_key: str | None, model_params: Mapping[str, Any]
-) -> Mapping[str, str | None]:
-    if custom_llm_provider != "azure":
-        return MappingProxyType({"api-key": api_key})
-    return azure_realtime.get_auth_headers(
-        api_key=api_key,
-        azure_ad_token=(None if api_key else get_azure_ad_token(GenericLiteLLMParams(**model_params))),
-    )
+) -> Mapping[str, str]:
+    if custom_llm_provider == "azure":
+        return azure_realtime.get_auth_headers(
+            api_key=api_key,
+            azure_ad_token=(None if api_key else get_azure_ad_token(GenericLiteLLMParams(**model_params))),
+        )
+    if api_key is None:
+        return _EMPTY_AUTH_HEADERS
+    return MappingProxyType({"Authorization": f"Bearer {api_key}"})
 
 
 async def _realtime_health_check(
@@ -629,34 +643,46 @@ async def _realtime_health_check(
     """
     import websockets
 
+    resolved_params: Final = _model_params_with_stored_credentials(model_params or _EMPTY_MODEL_PARAMS)
+    resolved_api_key: Final = cast(  # cast-ok: provider parameters expose optional string credentials
+        str | None, api_key or resolved_params.get("api_key")
+    )
+    resolved_api_base: Final = cast(  # cast-ok: provider parameters expose optional string endpoints
+        str | None, api_base or resolved_params.get("api_base")
+    )
+    resolved_api_version: Final = cast(  # cast-ok: provider parameters expose optional string versions
+        str | None, api_version or resolved_params.get("api_version")
+    )
     url: str | None = None
     auth_headers: Final = _realtime_health_check_auth_headers(
         custom_llm_provider=custom_llm_provider,
-        api_key=api_key,
-        model_params=model_params or _EMPTY_MODEL_PARAMS,
+        api_key=resolved_api_key,
+        model_params=resolved_params,
     )
     if custom_llm_provider == "azure":
         resolved_protocol, azure_query_params = _azure_realtime_health_protocol(
             model=model,
             realtime_protocol=realtime_protocol,
-            model_params=model_params or _EMPTY_MODEL_PARAMS,
+            model_params=resolved_params,
         )
         url = azure_realtime._construct_url(
-            api_base=api_base or "",
+            api_base=resolved_api_base or "",
             model=model,
-            api_version=api_version or "2024-10-01-preview",
+            api_version=resolved_api_version or "2024-10-01-preview",
             realtime_protocol=resolved_protocol,
             query_params=azure_query_params,
         )
     elif custom_llm_provider == "openai":
         url = openai_realtime._construct_url(
-            api_base=api_base or "https://api.openai.com/",
+            api_base=resolved_api_base or "https://api.openai.com/",
             query_params={"model": model},
         )
     elif custom_llm_provider == "xai":
-        url = xai_realtime._construct_url(api_base=api_base or "https://api.x.ai/v1", query_params={"model": model})
+        url = xai_realtime._construct_url(
+            api_base=resolved_api_base or "https://api.x.ai/v1", query_params={"model": model}
+        )
     elif custom_llm_provider == "vertex_ai":
-        vertex_model_params: Final = model_params or {}
+        vertex_model_params: Final = dict(resolved_params)
         resolved_location: Final = vertex_llm_base.get_vertex_region(
             vertex_region=VertexBase.safe_get_vertex_ai_location(vertex_model_params),
             model=model,
@@ -675,19 +701,19 @@ async def _realtime_health_check(
             project=resolved_project,
             location=resolved_location,
         )
-        url = vertex_realtime_config.get_complete_url(api_base=api_base, model=model)
-        ssl_context = get_shared_realtime_ssl_context()
+        url = vertex_realtime_config.get_complete_url(api_base=resolved_api_base, model=model)
+        vertex_ssl_context: Final = get_shared_realtime_ssl_context()
         headers: Final = vertex_realtime_config.validate_environment(headers={}, model=model, api_key=None)
         async with websockets.connect(
             url,
             additional_headers=headers,
             max_size=REALTIME_WEBSOCKET_MAX_MESSAGE_SIZE_BYTES,
-            ssl=ssl_context,
+            ssl=vertex_ssl_context,
         ):
             return True
     else:
         raise ValueError(f"Unsupported model: {model}")
-    ssl_context = get_shared_realtime_ssl_context()
+    ssl_context: Final = get_shared_realtime_ssl_context()
     async with websockets.connect(
         url,
         additional_headers=auth_headers,
diff --git a/litellm/responses/litellm_completion_transformation/transformation.py b/litellm/responses/litellm_completion_transformation/transformation.py
index 4415b0cbbbb..01fb6cb483d 100644
--- a/litellm/responses/litellm_completion_transformation/transformation.py
+++ b/litellm/responses/litellm_completion_transformation/transformation.py
@@ -2831,6 +2831,22 @@ class LiteLLMCompletionResponsesConfig:
                 if cache_write_tokens is not None
                 else MappingProxyType({})
             )
+            # The cost path reads the grounding counters off the input details, and a realtime
+            # session's usage is rebuilt from its own response.done, so dropping them here bills
+            # no per-query grounding fee at all.
+            grounding_request_counts: Final[Mapping[str, int]] = MappingProxyType(
+                {
+                    counter: count
+                    for counter, count in (
+                        ("web_search_requests", getattr(prompt_details, "web_search_requests", None)),
+                        (
+                            "google_maps_grounding_requests",
+                            getattr(prompt_details, "google_maps_grounding_requests", None),
+                        ),
+                    )
+                    if count is not None
+                }
+            )
             response_usage.input_tokens_details = InputTokensDetails(
                 cached_tokens=prompt_details.cached_tokens if prompt_details.cached_tokens is not None else 0,
                 text_tokens=prompt_details.text_tokens,
@@ -2839,6 +2855,7 @@ class LiteLLMCompletionResponsesConfig:
                     cached_tokens_details if isinstance(cached_tokens_details, CachedTokensDetails) else None
                 ),
                 **cache_write_extra,
+                **grounding_request_counts,
             )
 
         # Translate completion_tokens_details to output_tokens_details
diff --git a/litellm/responses/utils.py b/litellm/responses/utils.py
index d63e3ddf0aa..41a3ded7022 100644
--- a/litellm/responses/utils.py
+++ b/litellm/responses/utils.py
@@ -1183,6 +1183,10 @@ class ResponseAPILoggingUtils:
                         response_api_usage.input_tokens_details, "cached_tokens_details", None
                     ),
                     cache_write_tokens=getattr(response_api_usage.input_tokens_details, "cache_write_tokens", None),
+                    web_search_requests=getattr(response_api_usage.input_tokens_details, "web_search_requests", None),
+                    google_maps_grounding_requests=getattr(
+                        response_api_usage.input_tokens_details, "google_maps_grounding_requests", None
+                    ),
                 )
         completion_tokens_details: CompletionTokensDetailsWrapper | None = None
         output_tokens_details: Final[OutputTokensDetails | None] = getattr(
diff --git a/litellm/router.py b/litellm/router.py
index 6751711d690..a414bdabf80 100644
--- a/litellm/router.py
+++ b/litellm/router.py
@@ -8377,7 +8377,8 @@ class Router:
 
     def log_retry(self, kwargs: dict, e: Exception) -> dict:
         """
-        When a retry or fallback happens, record which model group, deployment and attempt just failed and why
+        When a retry or fallback happens, record which model group, deployment and attempt just failed and why,
+        and count it toward the request-wide num_retries_per_request cap
         """
         from litellm.types.router import RetryAttemptRecord
 
@@ -8401,7 +8402,10 @@ class Router:
             else ()
         )
         breadcrumbs: Final = (*kept_breadcrumbs, attempt_record)
+        earlier: Final = request_metadata.get("request_retry_count")
+        request_retry_count: Final = (earlier if type(earlier) is int and 0 <= earlier else 0) + 1
         kwargs[_metadata_var]["previous_models"] = breadcrumbs  # rebind-ok: the logging object already holds this dict
+        kwargs[_metadata_var]["request_retry_count"] = request_retry_count  # rebind-ok: same dict, read by the cap
         return kwargs
 
     def _update_usage(self, deployment_id: str, parent_otel_span: Span | None) -> int:
diff --git a/litellm/types/proxy/management_endpoints/key_management_endpoints.py b/litellm/types/proxy/management_endpoints/key_management_endpoints.py
index 9fb5bea81e3..63bbaa5ba4e 100644
--- a/litellm/types/proxy/management_endpoints/key_management_endpoints.py
+++ b/litellm/types/proxy/management_endpoints/key_management_endpoints.py
@@ -1,9 +1,12 @@
 from datetime import datetime
-from typing import Any, Final, Literal
+from typing import Any, Final, Literal, TypeAlias
 
 from pydantic import BaseModel, ConfigDict, model_validator
 from typing_extensions import ReadOnly, TypedDict
 
+from litellm.models.verification_token import LiteLLM_VerificationToken
+from litellm.proxy._types import GenerateKeyRequest, RegenerateKeyRequest, UpdateKeyRequest
+from litellm.types.llms.base import LiteLLMPydanticObjectBase
 from litellm.types.proxy.management_endpoints.internal_user_endpoints import InsensitiveContains
 
 
@@ -123,3 +126,24 @@ class BulkUpdateTeamKeysRequest(BaseModel):
         if not has_key_ids and not self.all_keys_in_team:
             raise ValueError("Must provide either `key_ids` (non-empty) or `all_keys_in_team=True`.")
         return self
+
+
+CustomKeyPolicyOperation: TypeAlias = Literal["generate", "update", "regenerate"]
+
+
+class CustomKeyPolicyRequest(LiteLLMPydanticObjectBase):
+    """What `general_settings.custom_key_policy` receives.
+
+    `effective_key` is the verification token row as it will be written: the existing row overlaid with the
+    requested changes, with `duration` resolved to `expires` and `budget_duration` to `budget_reset_at`. Values the
+    proxy fills in after the policy stay at their defaults: `token`, `key_name`, `created_by`, `updated_by` and the
+    soft-budget `budget_id` on generate, the rotated token on regenerate, and the `object_permission` relation on
+    every operation (`object_permission_id` is set; read `request.object_permission` for the requested change).
+    """
+
+    model_config = ConfigDict(protected_namespaces=(), frozen=True)
+
+    operation: CustomKeyPolicyOperation
+    existing_key: LiteLLM_VerificationToken | None
+    effective_key: LiteLLM_VerificationToken
+    request: GenerateKeyRequest | UpdateKeyRequest | RegenerateKeyRequest
diff --git a/tests/e2e/e2e_http.py b/tests/e2e/e2e_http.py
index 67370c98274..e0a20495964 100644
--- a/tests/e2e/e2e_http.py
+++ b/tests/e2e/e2e_http.py
@@ -170,6 +170,7 @@ class StreamingResponse(BaseModel):
     # the consumed body is elided, so this is the only place they surface.
     stream_error: str | None = None
     stream_done: bool = False
+    stream_done_positions: tuple[int, ...] = ()
 
     @property
     def ok(self) -> bool:
@@ -647,6 +648,7 @@ def streaming_outcome(
         stream_events=[payload for payload, _ in events],
         stream_event_arrivals=[arrived for _, arrived in events],
         stream_done=any(payload == _SSE_DONE for payload, _ in payloads),
+        stream_done_positions=tuple(index for index, (payload, _) in enumerate(payloads) if payload == _SSE_DONE),
         stream_error=next(
             (line.decode(errors="replace")[:300] for line, _ in stamped if _is_stream_error_line(line)),
             None,
diff --git a/tests/e2e/llm_translation/test_chat_stream_contract_e2e.py b/tests/e2e/llm_translation/test_chat_stream_contract_e2e.py
index 4db2fe004c5..fdb76df703d 100644
--- a/tests/e2e/llm_translation/test_chat_stream_contract_e2e.py
+++ b/tests/e2e/llm_translation/test_chat_stream_contract_e2e.py
@@ -1,51 +1,90 @@
-"""Vendor §12.3: chat completions streaming SSE contract (LIT-4778).
-
-Asserts a streamed /chat/completions response is SSE, carries content chunks,
-and terminates with the OpenAI [DONE] sentinel.
-"""
-
 from __future__ import annotations
 
+from typing import Final
+
 import pytest
-from e2e_config import unique_marker
+from e2e_config import provider_edge_base, unique_marker
 from e2e_http import require_successful_call
 from lifecycle import ResourceManager
-from models import ChatBody, ChatMessage, LiteLLMParamsBody
+from models import ChatBody, ChatMessage, ChatStreamOptions, LiteLLMParamsBody, Usage
 from proxy_client import ProxyClient
+from pydantic import BaseModel
 
-pytestmark = pytest.mark.e2e
+pytestmark = [pytest.mark.e2e, pytest.mark.replayable]
+
+
+class _Delta(BaseModel):
+    content: str | None = None
+
+
+class _Choice(BaseModel):
+    index: int
+    delta: _Delta
+    finish_reason: str | None = None
+
+
+class _Chunk(BaseModel):
+    choices: tuple[_Choice, ...]
+    usage: Usage | None = None
 
 
 class TestChatStreamContract:
     @pytest.mark.covers("llm.chat_completions.openai.basic.stream.works")
     def test_chat_stream_is_sse_and_ends_with_done(self, proxy: ProxyClient, resources: ResourceManager) -> None:
-        model = f"e2e-chat-stream-{unique_marker()}"
-        model_id = proxy.create_model(
+        model: Final = f"e2e-chat-stream-{unique_marker()}"
+        base: Final = provider_edge_base("openai")
+        model_id: Final = proxy.create_model(
             model,
-            LiteLLMParamsBody(model="openai/gpt-4o-mini", api_key="os.environ/OPENAI_API_KEY"),
+            LiteLLMParamsBody(
+                model="openai/gpt-5.6",
+                api_key="os.environ/OPENAI_API_KEY",
+                api_base=f"{base}/v1" if base else None,
+            ),
         )
         resources.defer(lambda: proxy.delete_model(model_id))
-        key = resources.key()
-
-        result = proxy.chat_stream(
+        key: Final = resources.key()
+        expected: Final = "The amber kite crosses the quiet lake."
+        result: Final = proxy.chat_stream(
             key,
             ChatBody(
                 model=model,
                 messages=[
                     ChatMessage(
-                        role="user",
-                        content=f"Reply with the single word ok. {unique_marker()}",
+                        role="user", content=f"Repeat exactly this sentence, with no additional text: {expected}"
                     )
                 ],
                 stream=True,
-                max_completion_tokens=32,
-                temperature=0.0,
+                stream_options=ChatStreamOptions(include_usage=True),
+                max_completion_tokens=256,
+                reasoning_effort="none",
             ),
         )
         require_successful_call(result)
         assert result.is_streaming, f"expected SSE content-type, got {result.content_type!r}"
         assert result.stream_events, "stream returned no data events"
-        assert result.stream_done, (
-            f"stream must terminate with [DONE]; "
-            f"chunks={result.chunks} done={result.stream_done} events={len(result.stream_events)}"
+        assert not result.stream_error, f"stream errored: {result.stream_error}"
+        assert result.stream_done, "stream must terminate with [DONE]"
+        assert result.stream_done_positions == (len(result.stream_events),), "[DONE] must occur once after all events"
+        chunks: Final = tuple(_Chunk.model_validate_json(event) for event in result.stream_events)
+        text_positions: Final = tuple(
+            i for i, chunk in enumerate(chunks) if any(c.delta.content for c in chunk.choices)
         )
+        terminal_positions: Final = tuple(
+            i for i, chunk in enumerate(chunks) if any(c.finish_reason is not None for c in chunk.choices)
+        )
+        assert text_positions, "stream completed without meaningful text"
+        assert len(terminal_positions) == 1, "expected exactly one terminal choice"
+        assert text_positions[0] < terminal_positions[0], "meaningful text must arrive before termination"
+        assert text_positions[-1] <= terminal_positions[0], "text arrived after termination"
+        assert all(c.index == 0 for chunk in chunks for c in chunk.choices)
+        assert tuple(c.finish_reason for c in chunks[terminal_positions[0]].choices) == ("stop",)
+        text: Final = "".join(c.delta.content or "" for chunk in chunks for c in chunk.choices)
+        assert text.strip() == expected, f"streamed answer was altered or incomplete: {text!r}"
+        usage_positions: Final = tuple(i for i, chunk in enumerate(chunks) if chunk.usage is not None)
+        assert usage_positions == (len(chunks) - 1,), "expected one final usage chunk"
+        assert terminal_positions[0] < usage_positions[0], "usage must follow the terminal choice"
+        usage: Final = chunks[-1].usage
+        assert usage is not None
+        assert usage.prompt_tokens is not None and usage.prompt_tokens > 0
+        assert usage.completion_tokens is not None and usage.completion_tokens > 0
+        assert usage.total_tokens == usage.prompt_tokens + usage.completion_tokens
diff --git a/tests/e2e/llm_translation/test_messages_e2e.py b/tests/e2e/llm_translation/test_messages_e2e.py
index c731b52acd8..ca58c30d40c 100644
--- a/tests/e2e/llm_translation/test_messages_e2e.py
+++ b/tests/e2e/llm_translation/test_messages_e2e.py
@@ -21,7 +21,12 @@ from e2e_http import assert_client_error, require_successful_call, unwrap
 from endpoints_client import EndpointsClient, MessagesResult
 from lifecycle import ResourceManager
 from models import (
+    AnthropicAssistantTurn,
+    AnthropicContentBlock,
     AnthropicCustomTool,
+    AnthropicToolChoice,
+    AnthropicToolResultBlock,
+    AnthropicToolResultTurn,
     AnthropicMessagesBody,
     ChatMessage,
     JsonSchemaProperty,
@@ -29,7 +34,7 @@ from models import (
     SpendLogRow,
     ToolInputSchema,
 )
-from pydantic import BaseModel
+from pydantic import BaseModel, ConfigDict
 
 pytestmark = [pytest.mark.e2e, pytest.mark.replayable]
 
@@ -284,8 +289,139 @@ class TestAnthropicMessages:
         result = endpoints_client.proxy.transport.send(
             "/v1/messages",
             headers=endpoints_client.proxy.transport.bearer(key),
-            json=_OptionalMessagesBody(
-                messages=[ChatMessage(role="user", content="hi")], max_tokens=50
-            ),
+            json=_OptionalMessagesBody(messages=[ChatMessage(role="user", content="hi")], max_tokens=50),
         )
         assert_client_error(result, "messages missing model")
+
+
+class _BridgeDelta(BaseModel):
+    type: str | None = None
+    partial_json: str | None = None
+    stop_reason: str | None = None
+
+
+class _BridgeEvent(BaseModel):
+    type: str
+    index: int | None = None
+    content_block: AnthropicContentBlock | None = None
+    delta: _BridgeDelta | None = None
+
+
+class _ParcelInput(BaseModel):
+    model_config = ConfigDict(extra="forbid", strict=True)
+    parcel: str
+    shelf: int
+
+
+def _tool_from_stream(events: tuple[_BridgeEvent, ...]) -> AnthropicContentBlock:
+    starts: Final = tuple(
+        event
+        for event in events
+        if event.type == "content_block_start"
+        and event.content_block is not None
+        and event.content_block.type == "tool_use"
+    )
+    assert len(starts) == 1, "expected exactly one tool call"
+    start: Final = starts[0]
+    block: Final = start.content_block
+    assert block is not None and block.id and start.index is not None
+    fragments: Final = tuple(
+        event
+        for event in events
+        if event.type == "content_block_delta" and event.delta is not None and event.delta.type == "input_json_delta"
+    )
+    assert fragments, "tool stream contained no argument fragments"
+    assert all(event.index == start.index for event in fragments), "tool fragments changed index"
+    positions: Final = tuple(i for i, event in enumerate(events) if event in fragments)
+    stops: Final = tuple(
+        i for i, event in enumerate(events) if event.type == "content_block_stop" and event.index == start.index
+    )
+    assert len(stops) == 1 and events.index(start) < positions[0] <= positions[-1] < stops[0]
+    assert tuple(
+        event.delta.stop_reason for event in events if event.type == "message_delta" and event.delta is not None
+    ) == ("tool_use",)
+    terminal_positions: Final = tuple(i for i, event in enumerate(events) if event.type == "message_delta")
+    assert len(terminal_positions) == 1 and stops[0] < terminal_positions[0] < len(events) - 1
+    assert tuple(i for i, event in enumerate(events) if event.type == "message_stop") == (len(events) - 1,), (
+        "tool stream did not terminate exactly once"
+    )
+    arguments: Final = _ParcelInput.model_validate_json(
+        "".join(event.delta.partial_json or "" for event in fragments if event.delta is not None)
+    )
+    return AnthropicContentBlock(type="tool_use", id=block.id, name=block.name, input=arguments.model_dump())
+
+
+def _parcel_result(tool: AnthropicContentBlock, result: AnthropicToolResultBlock) -> AnthropicToolResultTurn:
+    assert tool.id and result.tool_use_id == tool.id, "tool result ID does not match the emitted call"
+    return AnthropicToolResultTurn(content=[result])
+
+
+def _request_tool(
+    client: EndpointsClient, key: str, request: AnthropicMessagesBody, stream: bool
+) -> AnthropicContentBlock:
+    if stream:
+        response: Final = client.proxy.messages_stream(key, request)
+        require_successful_call(response)
+        assert response.is_streaming and not response.stream_error
+        return _tool_from_stream(tuple(_BridgeEvent.model_validate_json(event) for event in response.stream_events))
+    response_body: Final = unwrap(client.proxy.messages(key, request))
+    blocks: Final = tuple(block for block in response_body.content or () if block.type == "tool_use")
+    assert len(blocks) == 1
+    return blocks[0]
+
+
+class TestOpenAIMessagesToolContinuation:
+    @pytest.mark.parametrize("stream", [True, False], ids=["stream", "nonstream"])
+    def test_required_tool_arguments_and_correlated_result(
+        self, endpoints_client: EndpointsClient, resources: ResourceManager, stream: bool
+    ) -> None:
+        model: Final = f"e2e-bridge-tool-{unique_marker()}"
+        base: Final = provider_edge_base("openai")
+        model_id: Final = endpoints_client.create_model(
+            model,
+            LiteLLMParamsBody(
+                model="openai/gpt-5.6", api_key="os.environ/OPENAI_API_KEY", api_base=f"{base}/v1" if base else None
+            ),
+        )
+        resources.defer(lambda: endpoints_client.delete_model(model_id))
+        key: Final = resources.key(models=[model])
+        tool: Final = AnthropicCustomTool(
+            name="locate_parcel",
+            description="Look up the receipt for a parcel on a shelf. Return the receipt verbatim.",
+            input_schema=ToolInputSchema(
+                properties={"parcel": JsonSchemaProperty(type="string"), "shelf": JsonSchemaProperty(type="integer")},
+                required=["parcel", "shelf"],
+            ),
+        )
+        question: Final = ChatMessage(
+            role="user",
+            content="Call locate_parcel with parcel exactly amber-kite and shelf exactly 7. After the tool result, reply with only the receipt returned by the tool.",
+        )
+        request: Final = AnthropicMessagesBody(
+            model=model,
+            max_tokens=2048,
+            messages=[question],
+            tools=[tool],
+            tool_choice=AnthropicToolChoice(type="tool", name=tool.name),
+            stream=stream,
+        )
+        emitted: Final = _request_tool(endpoints_client, key, request, stream)
+        assert emitted.id and emitted.name == "locate_parcel"
+        assert emitted.input == {"parcel": "amber-kite", "shelf": 7}, "required tool arguments were lost or changed"
+        receipt: Final = f"receipt-{unique_marker()}"
+        result_turn: Final = _parcel_result(emitted, AnthropicToolResultBlock(tool_use_id=emitted.id, content=receipt))
+        continuation: Final = unwrap(
+            endpoints_client.proxy.messages(
+                key,
+                AnthropicMessagesBody(
+                    model=model,
+                    max_tokens=2048,
+                    tools=[tool],
+                    tool_choice=AnthropicToolChoice(type="none"),
+                    messages=[question, AnthropicAssistantTurn(content=[emitted]), result_turn],
+                ),
+            )
+        )
+        answer: Final = "".join(block.text or "" for block in continuation.content or ())
+        assert answer.strip() == receipt, "continuation did not consume the correlated tool result"
+        assert all(block.type != "tool_use" for block in continuation.content or ())
diff --git a/tests/e2e/models.py b/tests/e2e/models.py
index 6fca1268ebc..ba6d0fe3334 100644
--- a/tests/e2e/models.py
+++ b/tests/e2e/models.py
@@ -283,10 +283,15 @@ class ChatToolResultTurn(BaseModel):
 type ChatTurn = ChatMessage | ChatAssistantTurn | ChatToolResultTurn
 
 
+class ChatStreamOptions(BaseModel):
+    include_usage: bool
+
+
 class ChatBody(BaseModel):
     model: str
     messages: Sequence[ChatTurn]
     stream: bool = False
+    stream_options: ChatStreamOptions | None = None
     max_tokens: int | None = None
     max_completion_tokens: int | None = None
     temperature: float | None = None
@@ -488,12 +493,18 @@ class AnthropicToolResultTurn(BaseModel):
 type AnthropicMessage = ChatMessage | AnthropicAssistantTurn | AnthropicToolResultTurn
 
 
+class AnthropicToolChoice(BaseModel):
+    type: Literal["auto", "any", "tool", "none"]
+    name: str | None = None
+
+
 class AnthropicMessagesBody(BaseModel):
     model: str
     messages: list[AnthropicMessage]
     max_tokens: int
     stream: bool | None = None
     tools: list[AnthropicTool] | None = None
+    tool_choice: AnthropicToolChoice | None = None
     guardrails: list[str] | None = None
     cache: dict[str, bool] | None = {"no-cache": True}
 
diff --git a/tests/e2e/quota_management/spend_tracking/spend_reconciliation.py b/tests/e2e/quota_management/spend_tracking/spend_reconciliation.py
new file mode 100644
index 00000000000..26809874aed
--- /dev/null
+++ b/tests/e2e/quota_management/spend_tracking/spend_reconciliation.py
@@ -0,0 +1,113 @@
+from concurrent.futures import ThreadPoolExecutor
+from dataclasses import dataclass
+from math import isclose
+from typing import Final
+
+from e2e_config import provider_edge_base, unique_marker
+from e2e_http import unwrap
+from lifecycle import ResourceManager
+from models import ChatBody, ChatMessage, ChatResponse, KeyGenerateBody, LiteLLMParamsBody, TeamNewBody
+from spend_e2e_client import SpendClient
+
+INPUT_RATE: Final = 0.00004
+OUTPUT_RATE: Final = 0.00008
+
+
+@dataclass(frozen=True)
+class TeamTraffic:
+    team_id: str
+    key: str
+    responses: tuple[ChatResponse, ...]
+
+    @property
+    def prompt_tokens(self) -> int:
+        return sum(response.usage.prompt_tokens or 0 for response in self.responses if response.usage)
+
+    @property
+    def completion_tokens(self) -> int:
+        return sum(response.usage.completion_tokens or 0 for response in self.responses if response.usage)
+
+    @property
+    def spend(self) -> float:
+        return self.prompt_tokens * INPUT_RATE + self.completion_tokens * OUTPUT_RATE
+
+
+def create_traffic(client: SpendClient, resources: ResourceManager) -> tuple[TeamTraffic, ...]:
+    base: Final = provider_edge_base("openai")
+    model: Final = f"e2e-reconciliation-{unique_marker()}"
+    model_id: Final = client.proxy.create_model(
+        model,
+        LiteLLMParamsBody(
+            model="openai/gpt-5.6-luna",
+            api_key="os.environ/OPENAI_API_KEY",
+            api_base=None if base is None else f"{base}/v1",
+            input_cost_per_token=INPUT_RATE,
+            output_cost_per_token=OUTPUT_RATE,
+        ),
+    )
+    resources.defer(lambda: client.proxy.delete_model(model_id))
+
+    def team_traffic() -> TeamTraffic:
+        team: Final = client.proxy.create_team(TeamNewBody(team_alias=f"e2e-spend-{unique_marker()}"))
+        resources.defer(lambda: client.proxy.delete_team(team))
+        key: Final = client.proxy.generate_key(KeyGenerateBody(team_id=team, models=[model]))
+        resources.defer(lambda: client.proxy.delete_key(key))
+
+        prompts: Final = tuple(f"Reply with one word. {index} {unique_marker()}" for index in range(7))
+
+        def call(index: int) -> ChatResponse:
+            response: Final = unwrap(
+                client.proxy.chat(
+                    key,
+                    ChatBody(
+                        model=model,
+                        messages=[ChatMessage(role="user", content=prompts[index])],
+                        max_completion_tokens=128,
+                    ),
+                )
+            )
+            assert response.id, "successful response must have an ID"
+            assert response.usage is not None, "successful response must have usage"
+            assert response.usage.prompt_tokens is not None and response.usage.prompt_tokens > 0
+            assert response.usage.completion_tokens is not None and response.usage.completion_tokens > 0
+            assert response.usage.total_tokens == response.usage.prompt_tokens + response.usage.completion_tokens
+            assert not response.usage.cache_creation_input_tokens
+            assert not response.usage.cache_read_input_tokens
+            assert not response.usage.prompt_tokens_details or not response.usage.prompt_tokens_details.cached_tokens
+            return response
+
+        sequential: Final = call(0)
+        with ThreadPoolExecutor(max_workers=6) as pool:
+            concurrent: Final = tuple(pool.map(call, range(1, 7)))
+        return TeamTraffic(team, key, (sequential, *concurrent))
+
+    return tuple(team_traffic() for _ in range(2))
+
+
+def assert_logs_match(client: SpendClient, traffic: TeamTraffic) -> None:
+    expected_ids: Final = frozenset(response.id for response in traffic.responses)
+    assert len(expected_ids) == len(traffic.responses), "responses must have distinct IDs"
+    rows: Final = client.poll_logs_for_key(
+        traffic.key,
+        min_rows=len(traffic.responses),
+        predicate=lambda values: frozenset(row.request_id for row in values) == expected_ids,
+    )
+    assert frozenset(row.request_id for row in rows) == expected_ids, "stored IDs must equal returned response IDs"
+    assert len(rows) == len(traffic.responses), "expected exactly one scoped spend row per response"
+    by_id: Final = {row.request_id: row for row in rows}
+
+    def assert_response(response: ChatResponse) -> None:
+        row: Final = by_id[response.id]
+        usage: Final = response.usage
+        assert usage is not None and usage.prompt_tokens is not None and usage.completion_tokens is not None
+        assert row.team_id == traffic.team_id
+        assert row.status == "success"
+        assert row.cache_hit != "True"
+        assert row.prompt_tokens == usage.prompt_tokens
+        assert row.completion_tokens == usage.completion_tokens
+        assert row.total_tokens == usage.total_tokens
+        expected_cost: Final = usage.prompt_tokens * INPUT_RATE + usage.completion_tokens * OUTPUT_RATE
+        assert row.spend is not None and isclose(row.spend, expected_cost, rel_tol=1e-6, abs_tol=1e-9)
+
+    for response in traffic.responses:
+        assert_response(response)
diff --git a/tests/e2e/quota_management/spend_tracking/test_spend_tracking_e2e.py b/tests/e2e/quota_management/spend_tracking/test_spend_tracking_e2e.py
index c5d76d44580..8a91e53e7d7 100644
--- a/tests/e2e/quota_management/spend_tracking/test_spend_tracking_e2e.py
+++ b/tests/e2e/quota_management/spend_tracking/test_spend_tracking_e2e.py
@@ -17,13 +17,13 @@ fails the test; a pricing or token-count drift does not.
 
 import time
 from collections.abc import Callable
-from concurrent.futures import ThreadPoolExecutor
+from math import isclose
+from typing import Final
 
 import pytest
-
-from e2e_http import Result, Success
+from e2e_http import Success
 from lifecycle import ResourceManager
-from models import ChatResponse, LiteLLMParamsBody, SpendLogs, SpendLogsParams
+from models import LiteLLMParamsBody, SpendLogs, SpendLogsParams
 from spend_e2e_client import SpendClient, SpendLogRow, is_ok, unique_marker, unwrap
 
 pytestmark = pytest.mark.e2e
@@ -280,51 +280,22 @@ def test_key_spend_equals_sum_of_logs(client: SpendClient, scoped_key: str) -> N
     ), f"key aggregate {key_spend} != sum of logs {logs_total}; rows: {_summarize(rows)}"
 
 
+@pytest.mark.replayable
 @pytest.mark.covers("quota_management.spend_tracking.concurrent_burst.loses_no_spend")
 def test_burst_of_concurrent_calls_loses_no_spend(
-    client: SpendClient, scoped_key: str
+    client: SpendClient, resources: ResourceManager
 ) -> None:
-    """Six concurrent calls on one key: every call lands its own spend row under a
-    distinct request_id and the key aggregate equals the sum of the rows.
-    Sequential accuracy is covered by test_key_spend_equals_sum_of_logs; this pins
-    the concurrent increment path (parallel writers racing on one key's counter),
-    where a lost update can never be reproduced by sequential calls."""
-    burst = 6
+    from spend_reconciliation import TeamTraffic, assert_logs_match, create_traffic
 
-    def call(idx: int) -> Result[ChatResponse]:
-        return client.chat(
-            scoped_key,
-            "gemini-2.5-flash",
-            f"burst call {idx} {unique_marker()}",
-            max_tokens=16,
-        )
+    traffic: Final = create_traffic(client, resources)
 
-    with ThreadPoolExecutor(max_workers=burst) as pool:
-        results = tuple(pool.map(call, range(burst)))
-    failed = [r for r in results if not is_ok(r)]
-    assert not failed, f"{len(failed)}/{burst} burst calls failed; first: {failed[0]}"
+    def assert_team(team: TeamTraffic) -> None:
+        assert_logs_match(client, team)
+        key_spend: Final = client.poll_key_spend(team.key, minimum=team.spend * 0.999999)
+        assert isclose(key_spend, team.spend, rel_tol=1e-6, abs_tol=1e-9)
 
-    rows = client.poll_logs_for_key(
-        scoped_key,
-        min_rows=burst,
-        predicate=lambda rs: len([r for r in rs if (r.spend or 0) > 0]) >= burst,
-    )
-    costed = [r for r in rows if (r.spend or 0) > 0]
-    assert len(costed) >= burst, (
-        f"only {len(costed)}/{burst} burst calls produced a costed row - "
-        f"rows lost under concurrency: {_summarize(rows)}"
-    )
-    request_ids = [r.request_id for r in costed]
-    assert len(set(request_ids)) == len(request_ids), (
-        f"concurrent rows collapsed onto shared request_ids: {_summarize(rows)}"
-    )
-
-    logs_total = sum((r.spend or 0) for r in rows)
-    key_spend = client.poll_key_spend(scoped_key, minimum=logs_total * 0.999)
-    assert _approx_equal(key_spend, logs_total), (
-        f"key aggregate {key_spend} != sum of {len(rows)} rows {logs_total} - "
-        f"spend increments lost under concurrency: {_summarize(rows)}"
-    )
+    for team in traffic:
+        assert_team(team)
 
 
 @pytest.mark.covers("quota_management.spend_tracking.pagination.keeps_total")
diff --git a/tests/e2e/quota_management/spend_tracking/test_team_daily_activity_e2e.py b/tests/e2e/quota_management/spend_tracking/test_team_daily_activity_e2e.py
index ed0a6af4ec9..ef635e59743 100644
--- a/tests/e2e/quota_management/spend_tracking/test_team_daily_activity_e2e.py
+++ b/tests/e2e/quota_management/spend_tracking/test_team_daily_activity_e2e.py
@@ -7,13 +7,18 @@ missing start/end dates are rejected.
 
 from __future__ import annotations
 
+import time
 from datetime import datetime, timedelta, timezone
+from math import isclose
+from typing import Final
 
 import pytest
 from e2e_http import ProbeResult
-from models import DateRangeParams
+from lifecycle import ResourceManager
+from proxy_client import Converged, await_converged
 from pydantic import BaseModel
 from spend_e2e_client import SpendClient
+from spend_reconciliation import TeamTraffic, assert_logs_match, create_traffic
 
 pytestmark = pytest.mark.e2e
 
@@ -24,22 +29,45 @@ class TeamDailyActivityParams(BaseModel):
     start_date: str | None = None
     end_date: str | None = None
     page: int = 1
+    page_size: int = 1
+    team_ids: str | None = None
 
 
 class TeamDailyActivityRow(BaseModel):
     date: str
     metrics: TeamDailyActivityMetrics
+    breakdown: TeamDailyActivityBreakdown
 
 
 class TeamDailyActivityMetrics(BaseModel):
     spend: float
     total_tokens: int
+    prompt_tokens: int
+    completion_tokens: int
+    api_requests: int
+    successful_requests: int
+    failed_requests: int
+
+
+class TeamDailyActivityEntity(BaseModel):
+    metrics: TeamDailyActivityMetrics
+
+
+class TeamDailyActivityBreakdown(BaseModel):
+    entities: dict[str, TeamDailyActivityEntity]
 
 
 class TeamDailyActivityMetadata(BaseModel):
     page: int
     total_pages: int
     has_more: bool
+    total_spend: float
+    total_prompt_tokens: int
+    total_completion_tokens: int
+    total_tokens: int
+    total_api_requests: int
+    total_successful_requests: int
+    total_failed_requests: int
 
 
 class TeamDailyActivityResponse(BaseModel):
@@ -47,32 +75,128 @@ class TeamDailyActivityResponse(BaseModel):
     metadata: TeamDailyActivityMetadata
 
 
-def _range_days(days: int) -> DateRangeParams:
-    end = datetime.now(timezone.utc).date()
-    start = end - timedelta(days=days)
-    return DateRangeParams(start_date=start.isoformat(), end_date=end.isoformat())
-
-
 def _probe(client: SpendClient, params: BaseModel) -> ProbeResult:
     return client.proxy.transport.probe(ROUTE, params=params)
 
 
 class TestTeamDailyActivity:
+    @pytest.mark.replayable
     @pytest.mark.covers("mgmt.team.daily_activity.happy_path")
-    @pytest.mark.parametrize("days", [1, 7, 30])
-    def test_valid_date_range_returns_results_and_metadata(self, client: SpendClient, days: int) -> None:
-        result = _probe(client, _range_days(days))
-        assert result.status_code == 200, (
-            f"{ROUTE} range={days}d must be 200, got {result.status_code}: {result.body[:600]}"
+    def test_valid_date_range_returns_results_and_metadata(
+        self, client: SpendClient, resources: ResourceManager
+    ) -> None:
+        started: Final = datetime.now(timezone.utc).date()
+        traffic: Final = create_traffic(client, resources)
+        for team in traffic:
+            assert_logs_match(client, team)
+        ended: Final = datetime.now(timezone.utc).date()
+        team_ids: Final = ",".join(team.team_id for team in traffic)
+
+        def fetch(
+            page: int, start: str = (started - timedelta(days=1)).isoformat(), end: str = ended.isoformat()
+        ) -> TeamDailyActivityResponse:
+            result: Final = _probe(
+                client,
+                TeamDailyActivityParams(
+                    start_date=start,
+                    end_date=end,
+                    page=page,
+                    page_size=1,
+                    team_ids=team_ids,
+                ),
+            )
+            assert result.status_code == 200, f"daily activity failed: {result.status_code} {result.body[:300]}"
+            return TeamDailyActivityResponse.model_validate_json(result.body)
+
+        def pages() -> tuple[TeamDailyActivityResponse, ...]:
+            first: Final = fetch(1)
+            assert first.metadata.total_pages <= len(traffic) * 2, "unexpected extra scoped daily groups"
+            return (first, *(fetch(page) for page in range(2, first.metadata.total_pages + 1)))
+
+        outcome: Final = await_converged(
+            pages,
+            converged=lambda values: (
+                sum(page.metadata.total_api_requests for page in values) >= sum(len(team.responses) for team in traffic)
+            ),
+            timeout=client.proxy.poll_timeout,
+            interval=client.proxy.poll_interval,
+            now=time.monotonic,
+            sleep=time.sleep,
         )
-        parsed = TeamDailyActivityResponse.model_validate_json(result.body)
-        assert parsed.metadata.page == 1
-        assert parsed.metadata.total_pages >= 1
-        if parsed.results:
-            first = parsed.results[0]
-            assert first.date
-            assert first.metrics.spend >= 0
-            assert first.metrics.total_tokens >= 0
+        observed: Final = outcome.result if isinstance(outcome, Converged) else outcome.last_result
+        assert observed is not None, "daily aggregation must return a response before the deadline"
+
+        assert len(observed) >= 2, "two teams must exercise a page boundary"
+
+        def assert_page(index: int, page: TeamDailyActivityResponse) -> None:
+            assert page.metadata.page == index
+            assert page.metadata.total_pages == len(observed)
+            assert page.metadata.has_more == (index < len(observed))
+            assert len(page.results) == 1, "each fetched daily group must appear in results"
+            row: Final = page.results[0]
+            assert started <= datetime.fromisoformat(row.date).date() <= ended
+            assert len(row.breakdown.entities) == 1
+            assert row.metrics.total_tokens == page.metadata.total_tokens
+            assert row.metrics.prompt_tokens == page.metadata.total_prompt_tokens
+            assert row.metrics.completion_tokens == page.metadata.total_completion_tokens
+            assert row.metrics.api_requests == page.metadata.total_api_requests
+            assert row.metrics.successful_requests == page.metadata.total_successful_requests
+            assert row.metrics.failed_requests == page.metadata.total_failed_requests
+            assert isclose(row.metrics.spend, page.metadata.total_spend, rel_tol=1e-6, abs_tol=1e-9)
+
+        for index, page in enumerate(observed, 1):
+            assert_page(index, page)
+
+        entities: Final = tuple(
+            (team_id, entity.metrics)
+            for page in observed
+            for row in page.results
+            for team_id, entity in row.breakdown.entities.items()
+        )
+        assert frozenset(team_id for team_id, _ in entities) == frozenset(team.team_id for team in traffic)
+
+        def assert_team(team: TeamTraffic) -> None:
+            metrics: Final = tuple(metrics for team_id, metrics in entities if team_id == team.team_id)
+            assert sum(m.api_requests for m in metrics) == len(team.responses)
+            assert sum(m.successful_requests for m in metrics) == len(team.responses)
+            assert sum(m.failed_requests for m in metrics) == 0
+            assert sum(m.prompt_tokens for m in metrics) == team.prompt_tokens
+            assert sum(m.completion_tokens for m in metrics) == team.completion_tokens
+            assert sum(m.total_tokens for m in metrics) == team.prompt_tokens + team.completion_tokens
+            assert isclose(sum(m.spend for m in metrics), team.spend, rel_tol=1e-6, abs_tol=1e-9)
+
+        for team in traffic:
+            assert_team(team)
+
+        assert isclose(
+            sum(page.metadata.total_spend for page in observed),
+            sum(team.spend for team in traffic),
+            rel_tol=1e-6,
+            abs_tol=1e-9,
+        )
+        assert sum(page.metadata.total_tokens for page in observed) == sum(
+            team.prompt_tokens + team.completion_tokens for team in traffic
+        )
+
+        for days in (7, 30):
+            assert (
+                tuple(fetch(page, (started - timedelta(days=days)).isoformat()) for page in range(1, len(observed) + 1))
+                == observed
+            ), f"{days}-day activity must preserve the same isolated groups and totals"
+
+        empty_date: Final = (started - timedelta(days=7)).isoformat()
+        empty: Final = fetch(1, empty_date, empty_date)
+        assert empty.results == []
+        assert empty.metadata.total_pages == 0
+        assert empty.metadata.page == 1
+        assert not empty.metadata.has_more
+        assert empty.metadata.total_spend == 0
+        assert empty.metadata.total_tokens == 0
+        assert empty.metadata.total_api_requests == 0
+        assert empty.metadata.total_prompt_tokens == 0
+        assert empty.metadata.total_completion_tokens == 0
+        assert empty.metadata.total_successful_requests == 0
+        assert empty.metadata.total_failed_requests == 0
 
     @pytest.mark.covers("mgmt.team.daily_activity.missing_start_date_rejected")
     def test_missing_start_date_is_rejected(self, client: SpendClient) -> None:
diff --git a/tests/pass_through_unit_tests/test_vertex_ai_live_passthrough.py b/tests/pass_through_unit_tests/test_vertex_ai_live_passthrough.py
index e2eb6d0b68b..8b3dc436b8f 100644
--- a/tests/pass_through_unit_tests/test_vertex_ai_live_passthrough.py
+++ b/tests/pass_through_unit_tests/test_vertex_ai_live_passthrough.py
@@ -6,12 +6,15 @@ including the logging handler, cost tracking, and WebSocket message processing.
 """
 
 import json
+from collections.abc import Sequence
 from datetime import datetime
 from unittest.mock import AsyncMock, Mock, patch, MagicMock
 from typing import Dict, List, Any, Optional
 
 import pytest
 import httpx
+import litellm
+from typing_extensions import NotRequired, ReadOnly, TypedDict
 
 # Add the parent directory to the system path
 
@@ -22,10 +25,16 @@ from litellm.proxy.pass_through_endpoints.success_handler import (
     PassThroughEndpointLogging,
 )
 from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
-from litellm.types.utils import LlmProviders
+from litellm.types.utils import CostBreakdown, LlmProviders, Usage
 from litellm.proxy._types import UserAPIKeyAuth
 
 
+class _LiveTurn(TypedDict):
+    prompt: ReadOnly[tuple[int, int]]
+    candidates: ReadOnly[tuple[int, int]]
+    candidate_audio_token_count_missing: NotRequired[ReadOnly[bool]]
+
+
 class TestVertexAILivePassthroughLoggingHandler:
     """Test the Vertex AI Live Passthrough Logging Handler"""
 
@@ -39,6 +48,7 @@ class TestVertexAILivePassthroughLoggingHandler:
         """Create a mock logging object"""
         mock = MagicMock(spec=LiteLLMLoggingObj)
         mock.model_call_details = {}
+        mock._response_cost_calculator.return_value = None
         return mock
 
     @pytest.fixture
@@ -201,88 +211,490 @@ class TestVertexAILivePassthroughLoggingHandler:
         assert text_prompt["tokenCount"] == 10
         assert audio_prompt["tokenCount"] == 10
 
-    @patch(
-        "litellm.proxy.pass_through_endpoints.llm_provider_handlers.vertex_ai_live_passthrough_logging_handler.get_model_info"
-    )
-    def test_calculate_cost_basic(self, mock_get_model_info, handler):
-        """Test basic cost calculation"""
-        mock_get_model_info.return_value = {
-            "input_cost_per_token": 0.000001,
-            "output_cost_per_token": 0.000002,
-        }
+    def test_usage_carries_every_modality(self, handler):
+        """Regression: the Usage object reported only TEXT, so audio and image billed as nothing.
 
+        prompt_tokens must be the full count and the details must name each modality,
+        because the cost calculator prices audio and image from *_tokens_details.
+        """
         usage_metadata = {
-            "promptTokenCount": 100,
-            "candidatesTokenCount": 50,
-            "totalTokenCount": 150,
-        }
-
-        cost = handler._calculate_live_api_cost("gemini-1.5-pro", usage_metadata)
-
-        # The cost calculation may include additional factors, so we check it's reasonable
-        expected_min_cost = (100 * 0.000001) + (50 * 0.000002)
-        assert cost >= expected_min_cost
-        assert cost > 0
-
-    @patch(
-        "litellm.proxy.pass_through_endpoints.llm_provider_handlers.vertex_ai_live_passthrough_logging_handler.get_model_info"
-    )
-    def test_calculate_cost_with_audio(self, mock_get_model_info, handler):
-        """Test cost calculation with audio tokens"""
-        mock_get_model_info.return_value = {
-            "input_cost_per_token": 0.000001,
-            "output_cost_per_token": 0.000002,
-            "input_cost_per_audio_token": 0.0001,
-            "output_cost_per_audio_token": 0.0002,
-        }
-
-        usage_metadata = {
-            "promptTokenCount": 100,
-            "candidatesTokenCount": 50,
-            "totalTokenCount": 150,
+            "promptTokenCount": 1300,
+            "candidatesTokenCount": 124,
+            "totalTokenCount": 1424,
             "promptTokensDetails": [
-                {"modality": "TEXT", "tokenCount": 80},
-                {"modality": "AUDIO", "tokenCount": 20},
+                {"modality": "TEXT", "tokenCount": 13},
+                {"modality": "AUDIO", "tokenCount": 127},
+                {"modality": "IMAGE", "tokenCount": 1160},
             ],
             "candidatesTokensDetails": [
-                {"modality": "TEXT", "tokenCount": 30},
-                {"modality": "AUDIO", "tokenCount": 20},
+                {"modality": "TEXT", "tokenCount": 29},
+                {"modality": "AUDIO", "tokenCount": 95},
             ],
         }
 
-        cost = handler._calculate_live_api_cost("gemini-1.5-pro", usage_metadata)
+        usage = handler._create_usage_object_from_metadata(
+            usage_metadata=usage_metadata, model="gemini-live-2.5-flash"
+        )
 
-        # Should include both text and audio costs
-        assert cost > 0
-        assert cost > (100 * 0.000001) + (
-            50 * 0.000002
-        )  # Should be higher due to audio
+        assert usage.prompt_tokens == 1300, "the full prompt count must survive, not just its text share"
+        assert usage.completion_tokens == 124
+        assert usage.prompt_tokens_details.text_tokens == 13
+        assert usage.prompt_tokens_details.audio_tokens == 127
+        assert usage.prompt_tokens_details.image_tokens == 1160
+        assert usage.completion_tokens_details.text_tokens == 29
+        assert usage.completion_tokens_details.audio_tokens == 95
 
-    @patch(
-        "litellm.proxy.pass_through_endpoints.llm_provider_handlers.vertex_ai_live_passthrough_logging_handler.get_model_info"
+    def test_usage_sums_repeated_modality_entries(self, handler):
+        """A modality can appear more than once across aggregated turns; sum, don't overwrite."""
+        usage = handler._create_usage_object_from_metadata(
+            usage_metadata={
+                "promptTokenCount": 40,
+                "candidatesTokenCount": 0,
+                "promptTokensDetails": [
+                    {"modality": "IMAGE", "tokenCount": 10},
+                    {"modality": "IMAGE", "tokenCount": 25},
+                    {"modality": "TEXT", "tokenCount": 5},
+                ],
+            },
+            model="gemini-live-2.5-flash",
+        )
+        assert usage.prompt_tokens_details.image_tokens == 35
+        assert usage.prompt_tokens_details.text_tokens == 5
+
+    NATIVE_AUDIO_MODEL = "gemini-live-2.5-flash-preview-native-audio-09-2025"
+
+    # A four-turn native-audio session. Google charges per turn for the whole session context
+    # window, so the prompt side repeats the accumulated audio while the candidates side reports
+    # only that turn's own response. The last turn names AUDIO and omits its tokenCount, which is
+    # the shape Live really emits at the end of a spoken answer.
+    AUDIO_SESSION: tuple[_LiveTurn, ...] = (
+        {"prompt": (14, 122), "candidates": (8, 20)},
+        {"prompt": (21, 182), "candidates": (5, 50)},
+        {"prompt": (24, 203), "candidates": (13, 27)},
+        {"prompt": (24, 203), "candidates": (0, 3), "candidate_audio_token_count_missing": True},
     )
-    def test_calculate_cost_with_web_search(self, mock_get_model_info, handler):
-        """Test cost calculation with web search (tool use)"""
-        mock_get_model_info.return_value = {
-            "input_cost_per_token": 0.000001,
-            "output_cost_per_token": 0.000002,
-            "web_search_cost_per_request": 0.01,
-        }
 
-        usage_metadata = {
-            "promptTokenCount": 100,
-            "candidatesTokenCount": 50,
-            "totalTokenCount": 150,
-            "toolUsePromptTokenCount": 10,
-        }
+    @staticmethod
+    def _live_messages(turns: Sequence[_LiveTurn]) -> list[dict[str, object]]:
+        """Wrap (text, audio) prompt/candidate pairs as the server messages a Live session emits."""
+        return [{"type": "session.created", "session": {"id": "s"}}] + [
+            {
+                "type": "response.done",
+                "usageMetadata": {
+                    "promptTokenCount": sum(turn["prompt"]),
+                    "candidatesTokenCount": sum(turn["candidates"]),
+                    "totalTokenCount": sum(turn["prompt"]) + sum(turn["candidates"]),
+                    "promptTokensDetails": [
+                        {"modality": "TEXT", "tokenCount": turn["prompt"][0]},
+                        {"modality": "AUDIO", "tokenCount": turn["prompt"][1]},
+                    ],
+                    "candidatesTokensDetails": (
+                        [{"modality": "AUDIO"}]
+                        if turn.get("candidate_audio_token_count_missing")
+                        else [
+                            {"modality": "TEXT", "tokenCount": turn["candidates"][0]},
+                            {"modality": "AUDIO", "tokenCount": turn["candidates"][1]},
+                        ]
+                    ),
+                },
+            }
+            for turn in turns
+        ]
 
-        cost = handler._calculate_live_api_cost("gemini-1.5-pro", usage_metadata)
+    @staticmethod
+    def _session_usage(
+        handler: VertexAILivePassthroughLoggingHandler,
+        mock_logging_obj: MagicMock,
+        messages: list[dict[str, object]],
+        model: str,
+    ) -> Usage:
+        result = handler.vertex_ai_live_passthrough_handler(
+            websocket_messages=messages,
+            logging_obj=mock_logging_obj,
+            url_route="/vertex_ai/live",
+            start_time=datetime.now(),
+            end_time=datetime.now(),
+            request_body={},
+            model=model,
+        )
+        assert result["result"] is not None, "the handler must produce a usage-bearing response to bill"
+        return result["result"].usage
 
-        # Should include web search cost
-        expected_base_cost = (100 * 0.000001) + (50 * 0.000002)
-        # The web search cost might be handled differently, so just check it's reasonable
-        assert cost >= expected_base_cost
-        assert cost > 0
+    @classmethod
+    def _session_cost(
+        cls,
+        handler: VertexAILivePassthroughLoggingHandler,
+        mock_logging_obj: MagicMock,
+        messages: list[dict[str, object]],
+        model: str,
+    ) -> float:
+        from litellm.cost_calculator import completion_cost
+        from litellm.types.utils import ModelResponse
+
+        usage = cls._session_usage(handler, mock_logging_obj, messages, model)
+        return completion_cost(
+            completion_response=ModelResponse(
+                id="x", object="chat.completion", created=0, model=model, usage=usage, choices=[]
+            ),
+            model=f"vertex_ai/{model}",
+            custom_llm_provider="vertex_ai",
+            call_type="acompletion",
+        )
+
+    @classmethod
+    def _expected_session_cost(cls, turns: Sequence[_LiveTurn]) -> float:
+        from litellm.utils import get_model_info
+
+        info = get_model_info(model=cls.NATIVE_AUDIO_MODEL, custom_llm_provider="vertex_ai")
+        return (
+            sum(turn["prompt"][0] for turn in turns) * info["input_cost_per_token"]
+            + sum(turn["prompt"][1] for turn in turns) * info["input_cost_per_audio_token"]
+            + sum(turn["candidates"][0] for turn in turns) * info["output_cost_per_token"]
+            + sum(turn["candidates"][1] for turn in turns) * info["output_cost_per_audio_token"]
+        )
+
+    def test_every_turn_of_a_session_is_billed(self, handler, mock_logging_obj):
+        """Google charges per turn for the whole context window, so every turn adds to the bill.
+
+        Billing one snapshot instead gives away all the other turns: on this session the
+        largest single turn is well under the session total, and its share of the audio is
+        priced 6x the text rate, so the gap is money rather than rounding.
+        """
+        turns = self.AUDIO_SESSION[:3]
+        cost = self._session_cost(handler, mock_logging_obj, self._live_messages(turns), self.NATIVE_AUDIO_MODEL)
+
+        assert cost == pytest.approx(self._expected_session_cost(turns), rel=1e-9)
+        widest_single_turn = max(self._expected_session_cost([turn]) for turn in turns)
+        assert cost > widest_single_turn, "billing one snapshot drops every other turn of the session"
+
+    def test_audio_named_without_a_token_count_bills_at_the_audio_rate(self, handler, mock_logging_obj):
+        """Live can name the modality carrying the rest of a turn and omit its tokenCount.
+
+        Reading the absent key as zero left those tokens inside candidatesTokenCount but outside
+        the breakdown, so the calculator charged real speech at the text output rate. At this
+        entry's rates the last turn's 3 audio tokens are $0.0000360 rather than $0.0000060.
+        """
+        turns = self.AUDIO_SESSION
+        usage = self._session_usage(handler, mock_logging_obj, self._live_messages(turns), self.NATIVE_AUDIO_MODEL)
+
+        assert usage.completion_tokens_details.audio_tokens == 100, "the unpriced entry takes the turn's residual"
+        assert usage.completion_tokens_details.text_tokens == 26
+        assert usage.completion_tokens == 126
+
+        cost = self._session_cost(handler, mock_logging_obj, self._live_messages(turns), self.NATIVE_AUDIO_MODEL)
+        assert cost == pytest.approx(self._expected_session_cost(turns), rel=1e-9)
+
+    TOOL_USE_PER_TURN = (100, 250, 400)
+
+    def _grounded_messages(self):
+        """The three-turn session again, with each turn's own toolUsePromptTokenCount attached."""
+        messages = self._live_messages(self.AUDIO_SESSION[:3])
+        head, turns = messages[0], messages[1:]
+        return [head] + [
+            {**message, "usageMetadata": {**message["usageMetadata"], "toolUsePromptTokenCount": tool_use}}
+            for message, tool_use in zip(turns, self.TOOL_USE_PER_TURN)
+        ]
+
+    def test_server_side_tool_use_prompt_tokens_are_summed_over_the_session(self, handler, mock_logging_obj):
+        """toolUsePromptTokenCount rode the unknown-key pass-through, so it took the first turn only.
+
+        Every other total beside it is summed across the session, and the first turn is the
+        smallest number in the series, so a grounded session logged far fewer tool-use tokens
+        than it used. This session's turns are deliberately distinct, so 750 can only come from
+        summing: first-turn selection gives 100, last-turn or max gives 400.
+        """
+        grounded = self._grounded_messages()
+
+        usage = self._session_usage(handler, mock_logging_obj, grounded, self.NATIVE_AUDIO_MODEL)
+        assert usage.prompt_tokens_details.tool_use_tokens == sum(self.TOOL_USE_PER_TURN)
+
+    @staticmethod
+    def _grounding_frame(metadata: dict[str, object]) -> dict[str, object]:
+        """One server frame carrying grounding metadata, the way Live reports it."""
+        return {"type": "response.done", "serverContent": {"groundingMetadata": metadata}}
+
+    def test_web_grounding_is_counted_so_it_can_be_billed(self, handler, mock_logging_obj):
+        """Live reports grounding in the server frames and never in usageMetadata.
+
+        Nothing read those frames, so web_search_requests stayed unset and the cost path's only
+        trigger for the per-query grounding charge never fired. Google bills a grounded Live
+        prompt on top of its tokens, so the whole fee was missing from the bill.
+        """
+        messages = [
+            self._grounding_frame(
+                {
+                    "webSearchQueries": ["who won the 2026 world cup final"],
+                    "groundingChunks": [{"web": {"uri": "https://example.com"}}],
+                }
+            ),
+            *self._live_messages(self.AUDIO_SESSION[:1]),
+        ]
+
+        usage = self._session_usage(handler, mock_logging_obj, messages, self.NATIVE_AUDIO_MODEL)
+
+        assert usage.prompt_tokens_details.web_search_requests == 1, "a grounded turn must report its query"
+        assert getattr(usage.prompt_tokens_details, "google_maps_grounding_requests", None) is None
+
+    def test_maps_grounding_is_counted_under_its_own_sku(self, handler, mock_logging_obj):
+        """Maps grounding is a separate SKU from web search, so it needs its own counter.
+
+        A maps-only turn carries grounding chunks but no webSearchQueries, so counting queries
+        alone would report nothing and bill nothing.
+        """
+        messages = [
+            self._grounding_frame({"groundingChunks": [{"maps": {"placeId": "abc123"}}]}),
+            *self._live_messages(self.AUDIO_SESSION[:1]),
+        ]
+
+        usage = self._session_usage(handler, mock_logging_obj, messages, self.NATIVE_AUDIO_MODEL)
+
+        assert usage.prompt_tokens_details.google_maps_grounding_requests == 1
+        assert getattr(usage.prompt_tokens_details, "web_search_requests", None) is None
+
+    def test_an_ungrounded_session_reports_no_grounding(self, handler, mock_logging_obj):
+        """The counters must stay absent when no tool ran, or every session pays a grounding fee."""
+        usage = self._session_usage(
+            handler, mock_logging_obj, self._live_messages(self.AUDIO_SESSION[:1]), self.NATIVE_AUDIO_MODEL
+        )
+
+        assert getattr(usage.prompt_tokens_details, "web_search_requests", None) is None
+        assert getattr(usage.prompt_tokens_details, "google_maps_grounding_requests", None) is None
+
+    def test_grounding_adds_its_query_fee_to_the_session_bill(self, handler, mock_logging_obj):
+        """The counter only matters if it reaches the bill, so assert against the cost, not the field.
+
+        Same tokens either way: the difference between the two sessions is the grounding fee alone.
+        """
+        turns = self.AUDIO_SESSION[:1]
+        plain = self._session_cost(handler, mock_logging_obj, self._live_messages(turns), self.NATIVE_AUDIO_MODEL)
+        grounded = self._session_cost(
+            handler,
+            mock_logging_obj,
+            [self._grounding_frame({"webSearchQueries": ["q"]}), *self._live_messages(turns)],
+            self.NATIVE_AUDIO_MODEL,
+        )
+
+        assert grounded > plain, "a grounded session must cost more than the same tokens ungrounded"
+
+    def _priced_logging_obj(self) -> LiteLLMLoggingObj:
+        """A real logging object, since the session's price is handed to it turn by turn."""
+        logging_obj = LiteLLMLoggingObj(
+            model=self.NATIVE_AUDIO_MODEL,
+            messages=[],
+            stream=True,
+            call_type="pass_through_endpoint",
+            start_time=datetime.now(),
+            litellm_call_id="live-session",
+            function_id="live",
+        )
+        logging_obj.update_environment_variables(
+            model=self.NATIVE_AUDIO_MODEL,
+            user="u",
+            optional_params={},
+            litellm_params={},
+            call_type="pass_through_endpoint",
+        )
+        logging_obj.model_call_details["custom_llm_provider"] = "vertex_ai"
+        return logging_obj
+
+    def _billed_session(
+        self, handler: VertexAILivePassthroughLoggingHandler, messages: list[dict[str, object]]
+    ) -> tuple[float, CostBreakdown]:
+        logging_obj = self._priced_logging_obj()
+        result = handler.vertex_ai_live_passthrough_handler(
+            websocket_messages=messages,
+            logging_obj=logging_obj,
+            url_route="/vertex_ai/live",
+            start_time=datetime.now(),
+            end_time=datetime.now(),
+            request_body={},
+            model=self.NATIVE_AUDIO_MODEL,
+            custom_llm_provider="vertex_ai",
+        )
+        assert result["result"] is not None, "the handler must produce a usage-bearing response to bill"
+        assert logging_obj.cost_breakdown is not None, "the session's price must reach the logging object"
+        return result["result"]._hidden_params["response_cost"], logging_obj.cost_breakdown
+
+    def test_each_grounded_turn_pays_its_own_query_fee(self, handler):
+        """Google charges the grounding fee per grounded prompt, not per session.
+
+        Summing the session into one usage collapsed two grounded turns into one query, so the
+        second question was answered for free. The bill now grows by one fee per grounded turn.
+        """
+        head, turn = self._live_messages(self.AUDIO_SESSION[:1])
+        grounding = self._grounding_frame({"webSearchQueries": ["q"]})
+
+        plain_cost, _ = self._billed_session(handler, [head, turn, turn])
+        one_cost, one_breakdown = self._billed_session(handler, [head, grounding, turn, turn])
+        two_cost, two_breakdown = self._billed_session(handler, [head, grounding, turn, grounding, turn])
+
+        fee = one_cost - plain_cost
+        assert fee > 0, "a grounded turn must cost more than the same tokens ungrounded"
+        assert two_cost - plain_cost == pytest.approx(2 * fee), "two grounded turns must pay the fee twice"
+        assert two_breakdown["total_cost"] == pytest.approx(two_cost)
+        assert two_breakdown["tool_usage_cost"] == pytest.approx(2 * one_breakdown["tool_usage_cost"])
+
+    def test_a_query_repeated_across_turns_is_reported_once_per_turn(self, handler):
+        """The reported query count must agree with the bill, which charges every grounded turn.
+
+        The session usage collapsed duplicate query strings across turns while the price was
+        per turn, so two turns asking the same question paid two fees yet reported one query.
+        Duplicates within one turn still collapse, since that turn ran one search.
+        """
+        head, turn = self._live_messages(self.AUDIO_SESSION[:1])
+        grounding = self._grounding_frame({"webSearchQueries": ["q"]})
+        logging_obj = self._priced_logging_obj()
+
+        result = handler.vertex_ai_live_passthrough_handler(
+            websocket_messages=[head, grounding, turn, grounding, turn],
+            logging_obj=logging_obj,
+            url_route="/vertex_ai/live",
+            start_time=datetime.now(),
+            end_time=datetime.now(),
+            request_body={},
+            model=self.NATIVE_AUDIO_MODEL,
+            custom_llm_provider="vertex_ai",
+        )
+        _, one_breakdown = self._billed_session(handler, [head, grounding, turn])
+        repeated_within_turn = handler._session_usage(
+            [head, self._grounding_frame({"webSearchQueries": ["q", "q"]}), turn], self.NATIVE_AUDIO_MODEL
+        )
+
+        assert result["result"].usage.prompt_tokens_details.web_search_requests == 2
+        assert logging_obj.cost_breakdown["tool_usage_cost"] == pytest.approx(2 * one_breakdown["tool_usage_cost"])
+        assert repeated_within_turn.prompt_tokens_details.web_search_requests == 1
+
+    def test_the_fixed_cost_margin_is_charged_once_per_session(self, handler):
+        """A fixed cost margin is a flat per-request fee, and a Live session is one spend row.
+
+        Pricing each turn on its own applied the fixed margin per turn, so a two-turn session paid it
+        twice. The session now carries the fixed margin once no matter how many turns it billed.
+        """
+        head, turn = self._live_messages(self.AUDIO_SESSION[:1])
+        grounding = self._grounding_frame({"webSearchQueries": ["q"]})
+        messages = [head, grounding, turn, grounding, turn]
+
+        plain_cost, _ = self._billed_session(handler, messages)
+
+        fixed_amount = 0.01
+        with patch.object(litellm, "cost_margin_config", {"vertex_ai": {"fixed_amount": fixed_amount}}):
+            margined_cost, breakdown = self._billed_session(handler, messages)
+
+        assert margined_cost - plain_cost == pytest.approx(
+            fixed_amount
+        ), "a two-turn session must add the fixed margin once, not once per billed turn"
+        assert breakdown["margin_fixed_amount"] == pytest.approx(fixed_amount)
+        assert breakdown["margin_total_amount"] == pytest.approx(fixed_amount)
+
+    def test_reporting_tool_use_tokens_does_not_move_the_bill(self, handler, mock_logging_obj):
+        """Deliberate boundary: these tokens are reported here, and priced nowhere.
+
+        generic_cost_per_token reads the input bill out of prompt_tokens_details, and falls
+        back to prompt_tokens only when the details carry no text or a cache hit overlaps them,
+        so adding tool-use tokens to prompt_tokens is worth nothing on an ordinary Live turn and
+        over-charges against the cache-overlap correction when it is not. Pricing them belongs
+        in the shared input-cost path, beside the modality terms that already read the details.
+        """
+        turns = self.AUDIO_SESSION[:3]
+        plain_cost = self._session_cost(handler, mock_logging_obj, self._live_messages(turns), self.NATIVE_AUDIO_MODEL)
+        grounded_cost = self._session_cost(
+            handler, mock_logging_obj, self._grounded_messages(), self.NATIVE_AUDIO_MODEL
+        )
+
+        assert plain_cost == pytest.approx(self._expected_session_cost(turns), rel=1e-9)
+        assert grounded_cost == pytest.approx(plain_cost, rel=1e-9), "reporting tool use must not move the bill"
+
+    def test_a_malformed_details_entry_does_not_cost_the_whole_session(self, handler, mock_logging_obj):
+        """A ``*TokensDetails`` value that is not a list of objects must not take the session down.
+
+        The handler's only error path returns no result at all, so one odd frame used to throw
+        while reading it and the whole session billed nothing. The good turns still bill.
+        """
+        turns = self.AUDIO_SESSION[:3]
+        messages = self._live_messages(turns)
+        mangled = [dict(message) for message in messages]
+        mangled[1]["usageMetadata"] = {**mangled[1]["usageMetadata"], "promptTokensDetails": "TEXT"}
+
+        usage = self._session_usage(handler, mock_logging_obj, mangled, self.NATIVE_AUDIO_MODEL)
+
+        surviving = turns[1:]
+        assert usage.prompt_tokens_details.audio_tokens == sum(turn["prompt"][1] for turn in surviving)
+        assert usage.prompt_tokens_details.text_tokens == sum(turn["prompt"][0] for turn in surviving)
+        assert usage.prompt_tokens == sum(sum(turn["prompt"]) for turn in turns), "the totals still cover every turn"
+
+        direct = handler._create_usage_object_from_metadata(
+            usage_metadata={
+                "promptTokenCount": 40,
+                "candidatesTokenCount": 12,
+                "promptTokensDetails": [{"modality": "AUDIO", "tokenCount": 40}, "AUDIO"],
+                "candidatesTokensDetails": {"modality": "TEXT", "tokenCount": 12},
+            },
+            model=self.NATIVE_AUDIO_MODEL,
+        )
+        assert direct.prompt_tokens_details.audio_tokens == 40, "the well-formed entry beside a bad one still counts"
+        assert direct.completion_tokens == 12
+
+    @pytest.mark.parametrize(
+        "label,prompt_details,candidate_details",
+        [
+            ("text only", [("TEXT", 6)], [("TEXT", 2)]),
+            ("audio in", [("TEXT", 13), ("AUDIO", 127)], [("TEXT", 18)]),
+            ("image in", [("TEXT", 10), ("IMAGE", 258)], [("TEXT", 24)]),
+            ("frames in", [("TEXT", 11), ("IMAGE", 1032)], [("TEXT", 26)]),
+            ("audio both ways", [("TEXT", 13), ("AUDIO", 127)], [("TEXT", 29), ("AUDIO", 95)]),
+        ],
+    )
+    def test_live_session_bills_each_modality_at_its_own_rate(self, handler, label, prompt_details, candidate_details):
+        """Every payload here is a real Vertex Live session's usageMetadata.
+
+        Before the fix these billed the text share only, from 1x (text) to 55x under.
+        The expected amount is derived from the entry's own rates rather than hardcoded,
+        so this stays correct as prices move, and it is asserted exactly, so dropping a
+        modality and double-charging one both fail.
+        """
+        from litellm.cost_calculator import completion_cost
+        from litellm.types.utils import ModelResponse
+        from litellm.utils import get_model_info
+
+        model = self.NATIVE_AUDIO_MODEL
+        info = get_model_info(model=model, custom_llm_provider="vertex_ai")
+
+        text_in = info["input_cost_per_token"]
+        audio_in = info.get("input_cost_per_audio_token") or text_in
+        image_in = info.get("input_cost_per_image_token") or text_in
+        text_out = info["output_cost_per_token"]
+        audio_out = info.get("output_cost_per_audio_token") or text_out
+        rate_in = {"TEXT": text_in, "AUDIO": audio_in, "IMAGE": image_in}
+        rate_out = {"TEXT": text_out, "AUDIO": audio_out}
+
+        expected = sum(c * rate_in[m] for m, c in prompt_details) + sum(c * rate_out[m] for m, c in candidate_details)
+
+        usage = handler._create_usage_object_from_metadata(
+            usage_metadata={
+                "promptTokenCount": sum(c for _, c in prompt_details),
+                "candidatesTokenCount": sum(c for _, c in candidate_details),
+                "promptTokensDetails": [{"modality": m, "tokenCount": c} for m, c in prompt_details],
+                "candidatesTokensDetails": [{"modality": m, "tokenCount": c} for m, c in candidate_details],
+            },
+            model=model,
+        )
+
+        cost = completion_cost(
+            completion_response=ModelResponse(
+                id="x", object="chat.completion", created=0, model=model, usage=usage, choices=[]
+            ),
+            model=f"vertex_ai/{model}",
+            custom_llm_provider="vertex_ai",
+            call_type="acompletion",
+        )
+
+        assert cost == pytest.approx(expected, rel=1e-9), label
+
+        text_only = sum(c for m, c in prompt_details if m == "TEXT") * text_in + sum(
+            c for m, c in candidate_details if m == "TEXT"
+        ) * text_out
+        if any(m != "TEXT" for m, _ in prompt_details + candidate_details) and audio_in != text_in:
+            assert cost > text_only, f"{label}: non-text modalities must add cost"
 
     def test_vertex_ai_live_passthrough_handler_integration(
         self, handler, mock_logging_obj, sample_websocket_messages
@@ -376,6 +788,7 @@ class TestVertexAILivePassthroughIntegration:
         """Create a mock logging object"""
         mock = MagicMock(spec=LiteLLMLoggingObj)
         mock.model_call_details = {}
+        mock._response_cost_calculator.return_value = None
         return mock
 
     @patch(
@@ -509,6 +922,7 @@ class TestVertexAILivePassthroughErrorHandling:
         """Create a mock logging object"""
         mock = MagicMock(spec=LiteLLMLoggingObj)
         mock.model_call_details = {}
+        mock._response_cost_calculator.return_value = None
         return mock
 
     def test_invalid_websocket_messages_format(self):
@@ -540,25 +954,24 @@ class TestVertexAILivePassthroughErrorHandling:
         result = handler._extract_usage_metadata_from_websocket_messages(messages)
         assert result is None
 
-    @patch(
-        "litellm.proxy.pass_through_endpoints.llm_provider_handlers.vertex_ai_live_passthrough_logging_handler.get_model_info"
-    )
-    def test_cost_calculation_with_missing_model_info(self, mock_get_model_info):
-        """Test cost calculation when model info is missing"""
+    def test_usage_without_modality_details(self):
+        """Older payloads carry only the totals; fall back to them rather than reporting zero."""
         handler = VertexAILivePassthroughLoggingHandler()
 
-        # Mock missing model info
-        mock_get_model_info.return_value = {}
+        usage = handler._create_usage_object_from_metadata(
+            usage_metadata={
+                "promptTokenCount": 100,
+                "candidatesTokenCount": 50,
+                "totalTokenCount": 150,
+            },
+            model="unknown-model",
+        )
 
-        usage_metadata = {
-            "promptTokenCount": 100,
-            "candidatesTokenCount": 50,
-            "totalTokenCount": 150,
-        }
-
-        # Should not raise an exception, should return 0 or handle gracefully
-        cost = handler._calculate_live_api_cost("unknown-model", usage_metadata)
-        assert cost == 0.0
+        assert usage.prompt_tokens == 100
+        assert usage.completion_tokens == 50
+        assert usage.total_tokens == 150
+        assert usage.prompt_tokens_details.audio_tokens is None
+        assert usage.prompt_tokens_details.image_tokens is None
 
     def test_handler_with_none_websocket_messages(self, mock_logging_obj):
         """Test handler with None websocket messages"""
diff --git a/tests/router_unit_tests/test_router_helper_utils.py b/tests/router_unit_tests/test_router_helper_utils.py
index 5b06c5fdb01..b18bf9351c8 100644
--- a/tests/router_unit_tests/test_router_helper_utils.py
+++ b/tests/router_unit_tests/test_router_helper_utils.py
@@ -11,7 +11,7 @@ import litellm
 from unittest.mock import patch, MagicMock, AsyncMock
 from create_mock_standard_logging_payload import create_standard_logging_payload
 from litellm.types.utils import StandardLoggingPayload
-from litellm.types.router import Deployment, LiteLLM_Params, ModelInfo
+from litellm.types.router import Deployment, DeploymentTypedDict, LiteLLM_Params, ModelInfo
 from litellm.constants import DEFAULT_AUTO_ROUTER_MAX_INPUT_CHARS
 
 
@@ -630,10 +630,12 @@ def test_deployment_callback_respects_cooldown_time(model_list):
 
 
 @pytest.mark.parametrize("metadata_key", ["metadata", "litellm_metadata"])
-def test_log_retry(model_list, metadata_key):
-    """log_retry appends one flat record per failed attempt and copies neither the request kwargs nor
-    the request metadata into it"""
+def test_log_retry(model_list: list[DeploymentTypedDict], metadata_key: str) -> None:
+    """log_retry appends one flat record per failed attempt, copies neither the request kwargs nor the
+    request metadata into it, counts every failed attempt of the request independently of the
+    per-hop attempted_retries, and never trusts a negative count planted before the first failure"""
     router = Router(model_list=model_list)
+    rate_limit_error = litellm.RateLimitError(message="slow down", llm_provider="openai", model="gpt-3.5-turbo")
     new_kwargs = router.log_retry(
         kwargs={
             "model": "gpt-3.5-turbo",
@@ -641,7 +643,7 @@ def test_log_retry(model_list, metadata_key):
             "messages": [{"role": "user", "content": "hi"}],
             metadata_key: {"model_info": {"id": "deployment-1"}, "attempted_retries": 2, "user_api_key": "sk-proxy"},
         },
-        e=litellm.RateLimitError(message="slow down", llm_provider="openai", model="gpt-3.5-turbo"),
+        e=rate_limit_error,
     )
     assert json.loads(json.dumps(new_kwargs[metadata_key]["previous_models"])) == [
         {
@@ -652,6 +654,10 @@ def test_log_retry(model_list, metadata_key):
             "attempted_retries": 2,
         }
     ]
+    assert new_kwargs[metadata_key]["request_retry_count"] == 1
+    assert router.log_retry(kwargs=new_kwargs, e=rate_limit_error)[metadata_key]["request_retry_count"] == 2
+    planted_kwargs = {"model": "gpt-3.5-turbo", metadata_key: {"request_retry_count": -100}}
+    assert router.log_retry(kwargs=planted_kwargs, e=rate_limit_error)[metadata_key]["request_retry_count"] == 1
 
 
 def test_update_usage(model_list):
diff --git a/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py b/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
index 0882b329c49..7522e9a62e5 100644
--- a/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
+++ b/tests/test_litellm/llms/anthropic/chat/guardrail_translation/test_anthropic_guardrail_handler.py
@@ -13,6 +13,7 @@ import pytest
 
 
 from litellm.integrations.custom_guardrail import CustomGuardrail
+from litellm.litellm_core_utils.litellm_logging import Logging as LiteLLMLoggingObj
 from litellm.llms.base_llm.guardrail_translation.base_translation import StreamingScanKey
 from litellm.llms.anthropic.chat.guardrail_translation.handler import (
     AnthropicMessagesHandler,
@@ -635,14 +636,19 @@ class TestAnthropicMessagesHandlerInputProcessing:
         await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
 
         assert guardrail.inputs is not None
-        assert guardrail.inputs["texts"] == ["safe text", "prohibited correction"]
+        assert guardrail.inputs["texts"] == [
+            "trusted top-level system prompt",
+            "safe text",
+            "prohibited correction",
+        ]
         structured = guardrail.inputs["structured_messages"]
         assert [m["role"] for m in structured] == ["system", "user", "system"]
         assert structured[0]["content"] == "trusted top-level system prompt"
+        assert data["system"] == "trusted top-level system prompt"
         assert data["messages"][1]["content"] == "[MASKED]"
 
     @pytest.mark.asyncio
-    async def test_bedrock_masking_slice_is_unavailable_when_top_level_system_is_included(
+    async def test_bedrock_masking_slice_lines_up_when_top_level_system_is_included(
         self,
     ):
         from litellm.proxy.guardrails.guardrail_hooks.bedrock_guardrails import (
@@ -668,25 +674,25 @@ class TestAnthropicMessagesHandlerInputProcessing:
         structured = guardrail.inputs["structured_messages"]
 
         bedrock = BedrockGuardrail(guardrailIdentifier="gi", guardrailVersion="1")
-        assert sum(bedrock._count_message_texts(m) for m in structured) == len(texts) + 1
+        assert sum(bedrock._count_message_texts(m) for m in structured) == len(texts)
         latest_user_index = bedrock._find_latest_message_index(structured, target_role="user")
-        assert (
-            bedrock._locate_message_texts_slice(
-                structured_messages=structured,
-                target_index=latest_user_index,
-                texts=texts,
-            )
-            is None
-        )
-        assert (
-            bedrock._merge_masked_texts(
-                masked_texts=["{MASKED}"],
-                texts=texts,
-                scanned_slice=None,
-                scanned_role_subset=True,
-            )
-            == texts
+        scanned_slice = bedrock._locate_message_texts_slice(
+            structured_messages=structured,
+            target_index=latest_user_index,
+            texts=texts,
         )
+        assert scanned_slice == (3, 1)
+        assert bedrock._merge_masked_texts(
+            masked_texts=["{MASKED}"],
+            texts=texts,
+            scanned_slice=scanned_slice,
+            scanned_role_subset=True,
+        ) == [
+            "trusted top-level system prompt",
+            "safe text",
+            "prohibited correction",
+            "{MASKED}",
+        ]
 
     @pytest.mark.asyncio
     @pytest.mark.parametrize("skip_system_message_in_guardrail", [True, None])
@@ -1611,7 +1617,8 @@ class TestAnthropicMessagesIncrementalScan:
             )
             assert mock_api.call_count == 1
             assert [m["content"] for m in mock_api.call_args.kwargs["messages"]] == [
-                "What is the capital of France?"
+                "You are a helpful geography assistant.",
+                "What is the capital of France?",
             ]
             mock_api.reset_mock()
             await handler.process_input_messages(
@@ -2150,6 +2157,213 @@ class TestAnthropicMessagesScanOnlyToolResults:
         assert guardrail.captured_inputs.get("images") == ["TOOL_IMG"]
 
 
+class ToolCallArgumentsMaskingGuardrail(InputsRecordingGuardrail):
+    """Masks the canary inside tool-call arguments, in place or through a fresh list of plain dicts."""
+
+    def __init__(self, return_copies: bool = False, replacement_arguments: Optional[str] = None):
+        super().__init__()
+        self.return_copies = return_copies
+        self.replacement_arguments = replacement_arguments
+        self.seen_tool_calls: list[dict[str, object]] = []
+
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict[str, object],
+        input_type: Literal["request", "response"],
+        logging_obj: Optional[LiteLLMLoggingObj] = None,
+    ) -> GenericGuardrailAPIInputs:
+        outputs = await super().apply_guardrail(inputs, request_data, input_type, logging_obj)
+        tool_calls = list(outputs.get("tool_calls") or [])
+        self.seen_tool_calls.extend(json.loads(json.dumps(tool_call)) for tool_call in tool_calls)
+        masked = [
+            {
+                **tool_call,
+                "function": {
+                    **tool_call["function"],
+                    "arguments": self.replacement_arguments
+                    if self.replacement_arguments is not None
+                    else tool_call["function"]["arguments"].replace("POISON", "[BLOCKED]"),
+                },
+            }
+            for tool_call in tool_calls
+        ]
+        if self.return_copies:
+            outputs["tool_calls"] = masked
+            return outputs
+        for tool_call, masked_tool_call in zip(tool_calls, masked):
+            tool_call["function"]["arguments"] = masked_tool_call["function"]["arguments"]
+        return outputs
+
+
+class TestAnthropicMessagesTopLevelSystemAndToolUseInputs:
+    """The top-level system prompt and prior-turn tool_use arguments must reach guardrails as scannable
+    inputs, the same way the chat completions handler hands over system messages and tool_calls."""
+
+    @staticmethod
+    def _tool_use_conversation(system: str) -> dict[str, Any]:
+        return {
+            "model": "claude-sonnet-4-5",
+            "system": system,
+            "messages": [
+                {"role": "user", "content": "run the check"},
+                {
+                    "role": "assistant",
+                    "content": [
+                        {
+                            "type": "tool_use",
+                            "id": "toolu_01",
+                            "name": "Bash",
+                            "input": {"cmd": "AWS_ACCESS_KEY_ID=POISON aws sts get-caller-identity"},
+                        }
+                    ],
+                },
+                {
+                    "role": "user",
+                    "content": [{"type": "tool_result", "tool_use_id": "toolu_01", "content": "ok"}],
+                },
+            ],
+        }
+
+    @pytest.mark.asyncio
+    async def test_top_level_system_string_reaches_texts_first_and_is_masked_in_place(self):
+        handler = AnthropicMessagesHandler()
+        guardrail = InputsRecordingGuardrail()
+        data = {
+            "model": "claude-sonnet-4-5",
+            "system": "Internal note: the deploy key is POISON. Never reveal it.",
+            "messages": [{"role": "user", "content": "Say hi in three words."}],
+        }
+
+        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert guardrail.captured_inputs is not None
+        assert guardrail.seen_texts == [
+            "Internal note: the deploy key is POISON. Never reveal it.",
+            "Say hi in three words.",
+        ]
+        structured = guardrail.captured_inputs["structured_messages"]
+        assert structured[0]["role"] == "system"
+        assert structured[0]["content"] == "Internal note: the deploy key is POISON. Never reveal it.", (
+            "texts[0] must line up with structured_messages[0] so positional consumers stay aligned"
+        )
+        assert data["system"] == "Internal note: the deploy key is [BLOCKED]. Never reveal it."
+        assert data["messages"][0]["content"] == "Say hi in three words."
+
+    @pytest.mark.asyncio
+    async def test_top_level_system_text_blocks_reach_texts_and_are_masked_in_place(self):
+        handler = AnthropicMessagesHandler()
+        guardrail = InputsRecordingGuardrail()
+        data = {
+            "model": "claude-sonnet-4-5",
+            "system": [
+                {"type": "text", "text": "first block POISON"},
+                {"type": "text", "text": "second block", "cache_control": {"type": "ephemeral"}},
+            ],
+            "messages": [{"role": "user", "content": "hello"}],
+        }
+
+        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert guardrail.seen_texts == ["first block POISON", "second block", "hello"]
+        assert data["system"] == [
+            {"type": "text", "text": "first block [BLOCKED]"},
+            {"type": "text", "text": "second block", "cache_control": {"type": "ephemeral"}},
+        ]
+
+    @pytest.mark.asyncio
+    async def test_skip_system_message_keeps_the_top_level_system_out(self):
+        handler = AnthropicMessagesHandler()
+        guardrail = InputsRecordingGuardrail()
+        guardrail.skip_system_message_in_guardrail = True
+        data = {
+            "model": "claude-sonnet-4-5",
+            "system": "trusted POISON prompt",
+            "messages": [{"role": "user", "content": "hello"}],
+        }
+
+        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert guardrail.seen_texts == ["hello"]
+        assert data["system"] == "trusted POISON prompt"
+
+    @pytest.mark.asyncio
+    async def test_prior_turn_tool_use_input_reaches_tool_calls_in_openai_shape(self):
+        handler = AnthropicMessagesHandler()
+        guardrail = InputsRecordingGuardrail()
+        data = self._tool_use_conversation(system="You are a careful agent harness.")
+
+        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert guardrail.captured_inputs is not None
+        tool_calls = guardrail.captured_inputs.get("tool_calls")
+        assert tool_calls is not None and len(tool_calls) == 1
+        assert tool_calls[0]["id"] == "toolu_01"
+        assert tool_calls[0]["type"] == "function"
+        assert tool_calls[0]["function"]["name"] == "Bash"
+        assert json.loads(tool_calls[0]["function"]["arguments"]) == {
+            "cmd": "AWS_ACCESS_KEY_ID=POISON aws sts get-caller-identity"
+        }
+        assert data["messages"][1]["content"][0]["input"] == {
+            "cmd": "AWS_ACCESS_KEY_ID=POISON aws sts get-caller-identity"
+        }, "a guardrail that leaves tool_calls alone must leave the tool_use input alone"
+
+    @pytest.mark.asyncio
+    @pytest.mark.parametrize("return_copies", [False, True])
+    async def test_masked_tool_call_arguments_write_back_into_the_tool_use_input(self, return_copies: bool):
+        handler = AnthropicMessagesHandler()
+        guardrail = ToolCallArgumentsMaskingGuardrail(return_copies=return_copies)
+        data = self._tool_use_conversation(system="You are a careful agent harness.")
+
+        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert [tool_call["function"]["name"] for tool_call in guardrail.seen_tool_calls] == ["Bash"]
+        tool_use = data["messages"][1]["content"][0]
+        assert tool_use == {
+            "type": "tool_use",
+            "id": "toolu_01",
+            "name": "Bash",
+            "input": {"cmd": "AWS_ACCESS_KEY_ID=[BLOCKED] aws sts get-caller-identity"},
+        }
+        assert data["messages"][2]["content"][0]["tool_use_id"] == "toolu_01"
+
+    @pytest.mark.asyncio
+    async def test_non_json_rewritten_arguments_are_rejected_by_name(self):
+        from litellm.llms.base_llm.guardrail_translation.utils import UnappliableRequestRewrite
+
+        handler = AnthropicMessagesHandler()
+        guardrail = ToolCallArgumentsMaskingGuardrail(replacement_arguments="[REDACTED]")
+        data = self._tool_use_conversation(system="Internal note: the deploy key is POISON. Never reveal it.")
+        data["messages"][2]["content"][0]["content"] = "fetched POISON page"
+        original = json.loads(json.dumps(data))
+
+        with pytest.raises(UnappliableRequestRewrite) as excinfo:
+            await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert excinfo.value.guardrail_name == "scan-only-capture"
+        assert data["system"] == original["system"], "a rejected rewrite must leave the request untouched"
+        assert data["messages"] == original["messages"], "a rejected rewrite must leave the request untouched"
+
+    @pytest.mark.asyncio
+    async def test_scan_only_tool_results_keeps_system_and_tool_use_out(self):
+        handler = AnthropicMessagesHandler()
+        guardrail = InputsRecordingGuardrail()
+        guardrail.scan_only_tool_results = True
+        data = self._tool_use_conversation(system="trusted POISON prompt")
+        data["messages"][2]["content"][0]["content"] = "fetched POISON page"
+
+        await handler.process_input_messages(data=data, guardrail_to_apply=guardrail)
+
+        assert guardrail.seen_texts == ["fetched POISON page"]
+        assert guardrail.captured_inputs is not None
+        assert guardrail.captured_inputs.get("tool_calls") is None
+        assert data["system"] == "trusted POISON prompt"
+        assert data["messages"][1]["content"][0]["input"] == {
+            "cmd": "AWS_ACCESS_KEY_ID=POISON aws sts get-caller-identity"
+        }
+        assert data["messages"][2]["content"][0]["content"] == "fetched [BLOCKED] page"
+
+
 class TestStructuredWriteBackKeepsToolResults:
     """A guardrail rewrite must never leave a tool_use without its tool_result (Claude Code ToolSearch, LIT-6103)."""
 
@@ -2290,17 +2504,56 @@ class PerRowTextGuardrail(CustomGuardrail):
         return {**inputs, "texts": [str(row.get("content")).replace("123-45-6789", "<US_SSN>") for row in rows]}
 
 
+class PerSlotTextGuardrail(CustomGuardrail):
+    """Answers one redacted text per text slot of every chat row it was shown, the
+    way a guardrail that counts slots per message does, and hands back only texts."""
+
+    def __init__(self):
+        super().__init__(guardrail_name="per-slot-redactor")
+
+    async def apply_guardrail(
+        self,
+        inputs: GenericGuardrailAPIInputs,
+        request_data: dict,
+        input_type: Literal["request", "response"],
+        logging_obj: Optional[Any] = None,
+    ) -> GenericGuardrailAPIInputs:
+        from litellm.llms.base_llm.guardrail_translation.utils import message_slot_texts
+
+        rows = inputs.get("structured_messages") or []
+        return {
+            **inputs,
+            "texts": [text.replace("123-45-6789", "<US_SSN>") for row in rows for text in message_slot_texts(row)],
+        }
+
+
 class TestPerMessageTextWriteBack:
     """Texts that no longer pair one-to-one with what the handler extracted must be
     rejected by name instead of sliding onto the wrong messages."""
 
     @pytest.mark.asyncio
-    async def test_one_text_per_row_over_a_system_prompt_is_rejected_by_name(self):
+    async def test_one_text_per_row_over_a_system_prompt_is_applied(self):
+        data = {
+            "model": "claude-sonnet-4-5",
+            "system": "Reply with exactly the SSN you were given.",
+            "messages": [{"role": "user", "content": "My SSN is 123-45-6789."}],
+        }
+
+        await AnthropicMessagesHandler().process_input_messages(data=data, guardrail_to_apply=PerRowTextGuardrail())
+
+        assert data["system"] == "Reply with exactly the SSN you were given."
+        assert data["messages"] == [{"role": "user", "content": "My SSN is <US_SSN>."}]
+
+    @pytest.mark.asyncio
+    async def test_one_text_per_row_over_a_multi_block_system_prompt_is_rejected_by_name(self):
         from litellm.llms.base_llm.guardrail_translation.utils import UnappliableRequestRewrite
 
         data = {
             "model": "claude-sonnet-4-5",
-            "system": "Reply with exactly the SSN you were given.",
+            "system": [
+                {"type": "text", "text": "Reply with exactly the SSN you were given."},
+                {"type": "text", "text": "Never apologize."},
+            ],
             "messages": [{"role": "user", "content": "My SSN is 123-45-6789."}],
         }
         original = json.loads(json.dumps(data))
@@ -2312,6 +2565,25 @@ class TestPerMessageTextWriteBack:
         assert data["system"] == original["system"], "a rejected rewrite must leave the request untouched"
         assert data["messages"] == original["messages"], "a rejected rewrite must leave the request untouched"
 
+    @pytest.mark.asyncio
+    async def test_one_text_per_slot_over_a_system_prompt_with_an_empty_block_is_applied(self):
+        data = {
+            "model": "claude-sonnet-4-5",
+            "system": [
+                {"type": "text", "text": ""},
+                {"type": "text", "text": "Reply with exactly the SSN you were given."},
+            ],
+            "messages": [{"role": "user", "content": "My SSN is 123-45-6789."}],
+        }
+
+        await AnthropicMessagesHandler().process_input_messages(data=data, guardrail_to_apply=PerSlotTextGuardrail())
+
+        assert data["system"] == [
+            {"type": "text", "text": ""},
+            {"type": "text", "text": "Reply with exactly the SSN you were given."},
+        ]
+        assert data["messages"] == [{"role": "user", "content": "My SSN is <US_SSN>."}]
+
     @pytest.mark.asyncio
     async def test_one_text_per_row_without_a_system_prompt_is_applied(self):
         data = {
diff --git a/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_streaming_iterator_tool_args.py b/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_streaming_iterator_tool_args.py
index 29e9279731d..a20aaf2e324 100644
--- a/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_streaming_iterator_tool_args.py
+++ b/tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_streaming_iterator_tool_args.py
@@ -8,6 +8,8 @@ Without the fix, the AnthropicStreamWrapper silently dropped these
 arguments, causing tool_use blocks to arrive with empty input {}.
 """
 
+import json
+
 from typing import List
 from unittest.mock import MagicMock
 
@@ -139,9 +141,7 @@ async def test_async_stream_emits_input_json_delta_for_bundled_tool_args():
 
     # Verify the delta carries the tool arguments
     delta_event = events[input_json_delta_idx]
-    assert delta_event["delta"][
-        "partial_json"
-    ], "input_json_delta should have non-empty partial_json"
+    assert json.loads(delta_event["delta"]["partial_json"]) == {"location": "Boston"}
 
 
 @pytest.mark.asyncio
@@ -300,7 +300,7 @@ def test_sync_stream_emits_input_json_delta_for_bundled_tool_args():
     assert (
         input_json_delta_idx == tool_start_idx + 1
     ), "input_json_delta should immediately follow the tool_use content_block_start"
-    assert events[input_json_delta_idx]["delta"]["partial_json"]
+    assert json.loads(events[input_json_delta_idx]["delta"]["partial_json"]) == {"location": "Boston"}
 
 
 def test_sync_stream_no_extra_delta_when_tool_args_empty():
diff --git a/tests/test_litellm/llms/bedrock/test_web_identity_session_policy.py b/tests/test_litellm/llms/bedrock/test_web_identity_session_policy.py
index 3ea840519f9..cbb69b4ceed 100644
--- a/tests/test_litellm/llms/bedrock/test_web_identity_session_policy.py
+++ b/tests/test_litellm/llms/bedrock/test_web_identity_session_policy.py
@@ -32,9 +32,14 @@ action.
 import base64
 import json
 from datetime import datetime, timedelta, timezone
+from types import MappingProxyType
+from typing import Final
 from unittest.mock import MagicMock, patch
 
 import pytest
+from pydantic import TypeAdapter
+
+from litellm.llms.bedrock.base_aws_llm import WebIdentitySessionPolicy, _SessionPolicyStatement
 
 # Actions the Claude Platform on AWS service is documented to call.
 # Source: AWS IAM action reference + the #27678 surface area.
@@ -49,9 +54,9 @@ _CLAUDE_PLATFORM_ACTIONS = {
 }
 
 
-def _captured_policy() -> dict:
-    """Run _auth_with_web_identity_token under mocks + return the parsed
-    Policy dict that was actually sent to STS."""
+def _captured_policy_document() -> str:
+    """Run _auth_with_web_identity_token under mocks + return the Policy
+    JSON document that was actually sent to STS."""
     from litellm.llms.bedrock.base_aws_llm import BaseAWSLLM
 
     base = BaseAWSLLM()
@@ -84,11 +89,21 @@ def _captured_policy() -> dict:
 
     mock_sts.assume_role_with_web_identity.assert_called_once()
     kwargs = mock_sts.assume_role_with_web_identity.call_args.kwargs
-    policy_str = kwargs["Policy"]
-    return json.loads(policy_str)
+    return kwargs["Policy"]
 
 
-def _statement_by_sid(policy: dict, sid: str) -> dict:
+_SESSION_POLICY_ADAPTER: Final = TypeAdapter(WebIdentitySessionPolicy)
+
+
+def _captured_policy() -> WebIdentitySessionPolicy:
+    return _SESSION_POLICY_ADAPTER.validate_python(json.loads(_captured_policy_document()))
+
+
+def _granted_actions(policy: WebIdentitySessionPolicy) -> frozenset[str]:
+    return frozenset(action for stmt in policy["Statement"] for action in stmt["Action"])
+
+
+def _statement_by_sid(policy: WebIdentitySessionPolicy, sid: str) -> _SessionPolicyStatement:
     for stmt in policy["Statement"]:
         if stmt.get("Sid") == sid:
             return stmt
@@ -102,7 +117,6 @@ class TestWebIdentitySessionPolicyShape:
     def test_policy_parses_as_valid_iam_document(self):
         policy = _captured_policy()
         assert policy["Version"] == "2012-10-17"
-        assert isinstance(policy["Statement"], list)
         assert len(policy["Statement"]) >= 2
 
     def test_bedrock_statement_actions_preserved(self):
@@ -137,16 +151,7 @@ class TestClaudePlatformActionsCovered:
 
     @pytest.mark.parametrize("action", sorted(_CLAUDE_PLATFORM_ACTIONS))
     def test_claude_platform_action_present(self, action: str):
-        policy = _captured_policy()
-        # Action may live in any Statement — search across all.
-        all_actions: set = set()
-        for stmt in policy["Statement"]:
-            stmt_actions = stmt.get("Action")
-            if isinstance(stmt_actions, str):
-                all_actions.add(stmt_actions)
-            elif isinstance(stmt_actions, list):
-                all_actions.update(stmt_actions)
-        assert action in all_actions, (
+        assert action in _granted_actions(_captured_policy()), (
             f"{action} missing from session policy — "
             f"bedrock/claude_platform/* requests will 403 on OIDC auth"
         )
@@ -179,15 +184,7 @@ class TestBedrockMantleActionsCovered:
     action" even when the role's identity policy grants it."""
 
     def test_bedrock_mantle_create_inference_present(self):
-        policy = _captured_policy()
-        all_actions: set = set()
-        for stmt in policy["Statement"]:
-            stmt_actions = stmt.get("Action")
-            if isinstance(stmt_actions, str):
-                all_actions.add(stmt_actions)
-            elif isinstance(stmt_actions, list):
-                all_actions.update(stmt_actions)
-        assert "bedrock-mantle:CreateInference" in all_actions, (
+        assert "bedrock-mantle:CreateInference" in _granted_actions(_captured_policy()), (
             "bedrock-mantle:CreateInference missing from session policy — "
             "bedrock_mantle/* requests will 403 on OIDC/WIF auth"
         )
@@ -233,7 +230,7 @@ class TestInvalidIdentityTokenSurfacesAudience:
     operator can diagnose the mismatch without enabling LITELLM_LOG=DEBUG on a
     prod instance."""
 
-    _AUD = "https://guidepoint.litellm-prod.ai"
+    _AUD = "https://gateway.example.com"
     _ISS = "https://accounts.google.com"
     _STS_MESSAGE = (
         "An error occurred (InvalidIdentityToken) when calling the "
@@ -308,3 +305,44 @@ class TestPolicyTransportConditions:
             "ClaudePlatformLiteLLM must require aws:SecureTransport=true "
             "to keep parity with the bedrock statement"
         )
+
+
+_STS_SESSION_POLICY_PLAINTEXT_LIMIT: Final = 2048
+
+_BEDROCK_ROUTE_ACTIONS: Final = MappingProxyType(
+    {
+        "model/{model_id}/invoke": "bedrock:InvokeModel",
+        "model/{model_id}/invoke-with-response-stream": "bedrock:InvokeModelWithResponseStream",
+        "model/{model_id}/converse": "bedrock:InvokeModel",
+        "model/{model_id}/converse-stream": "bedrock:InvokeModelWithResponseStream",
+        "model/{model_id}/count-tokens": "bedrock:CountTokens",
+        "guardrail/{guardrail_id}/version/{version}/apply": "bedrock:ApplyGuardrail",
+        "rerank": "bedrock:Rerank",
+        "knowledgebases/{knowledge_base_id}/retrieve": "bedrock:Retrieve",
+        "knowledgebases": "bedrock:ListKnowledgeBases",
+        "agents/{agent_id}/agentAliases/{alias_id}/sessions/{session_id}/text": "bedrock:InvokeAgent",
+        "runtimes/{agent_runtime_arn}/invocations": "bedrock-agentcore:InvokeAgentRuntime",
+        "runtimes/{agent_runtime_arn}/invocations with X-Amzn-Bedrock-AgentCore-Runtime-User-Id": (
+            "bedrock-agentcore:InvokeAgentRuntimeForUser"
+        ),
+        "mcp": "bedrock-agentcore:InvokeGateway",
+    }
+)
+
+
+class TestSessionPolicyGrantsEveryBedrockRoute:
+    """LIT-7348: ``/rerank`` authorizes against ``bedrock:Rerank``, which the
+    ceiling never granted, so rerank 403d on web identity auth while static
+    credentials and IRSA worked. Each route the bedrock package signs with the
+    web identity session maps to the IAM action it authorizes against, and the
+    ceiling must grant every one of them."""
+
+    @pytest.mark.parametrize(("route", "action"), sorted(_BEDROCK_ROUTE_ACTIONS.items()))
+    def test_route_action_is_granted_by_the_ceiling(self, route: str, action: str):
+        assert action in _granted_actions(_captured_policy()), (
+            f"/{route} authorizes against {action}, which the session policy does not grant, "
+            "so it 403s on web identity auth"
+        )
+
+    def test_policy_document_fits_the_sts_plaintext_limit(self):
+        assert len(_captured_policy_document()) <= _STS_SESSION_POLICY_PLAINTEXT_LIMIT
diff --git a/tests/test_litellm/llms/gemini/realtime/test_gemini_realtime_transformation.py b/tests/test_litellm/llms/gemini/realtime/test_gemini_realtime_transformation.py
index 2b3b6343fad..3eb4a70ee15 100644
--- a/tests/test_litellm/llms/gemini/realtime/test_gemini_realtime_transformation.py
+++ b/tests/test_litellm/llms/gemini/realtime/test_gemini_realtime_transformation.py
@@ -1,4 +1,6 @@
 import json
+from collections.abc import Mapping
+from typing import cast
 from unittest.mock import MagicMock
 
 import pytest
@@ -6,6 +8,7 @@ import pytest
 
 import litellm
 from litellm.llms.gemini.realtime.transformation import GeminiRealtimeConfig
+from litellm.types.llms.gemini import BidiGenerateContentServerMessage
 
 
 def test_gemini_realtime_transformation_session_created():
@@ -2178,3 +2181,71 @@ def test_unbilled_usage_on_session_close_flushes_trailing_audio(patch_gemini_tra
     }
     assert usage == expected
     assert config.unbilled_usage_on_session_close("gemini-3.5-transcribe-live") is None
+
+
+def _grounded_live_frame(grounding_metadata: Mapping[str, object] | None) -> Mapping[str, object]:
+    """One Live server frame. Grounding metadata and usageMetadata arrive together, as Vertex sends them."""
+    from typing import Final
+
+    server_content: Final = {
+        "turnComplete": True,
+        **({} if grounding_metadata is None else {"groundingMetadata": grounding_metadata}),
+    }
+    return {
+        "serverContent": server_content,
+        "usageMetadata": {
+            "promptTokenCount": 19,
+            "candidatesTokenCount": 157,
+            "totalTokenCount": 176,
+            "promptTokensDetails": ({"modality": "TEXT", "tokenCount": 19},),
+            "candidatesTokensDetails": ({"modality": "AUDIO", "tokenCount": 157},),
+        },
+    }
+
+
+def _response_done_input_details(message: Mapping[str, object]) -> Mapping[str, object]:
+    """The ``input_tokens_details`` a ``response.done`` event carries, read off the emitted event."""
+    from typing import Final
+
+    config: Final = GeminiRealtimeConfig()
+    event: Final = config.transform_response_done_event(
+        message=cast(  # cast-ok: a test fixture stands in for the server frame TypedDict
+            BidiGenerateContentServerMessage, message
+        ),
+        current_response_id="resp_grounding",
+        current_conversation_id="conv_grounding",
+        output_items=None,
+    )
+    usage: Final = event["response"]["usage"]
+    assert usage, "response.done must carry a usage object"
+    return usage.get("input_tokens_details") or {}
+
+
+def test_gemini_realtime_response_done_counts_web_grounding():
+    """Regression: Live reports grounding in the server frames and never in usageMetadata.
+
+    Nothing read those frames on the realtime path, so web_search_requests stayed unset and the
+    cost path's only trigger for Google's per-query grounding charge never fired.
+
+    The counter is read off the emitted event, which is what the cost path is handed, so this covers
+    the grounding read and the usage bridge that carries it together
+    """
+    input_details = _response_done_input_details(
+        _grounded_live_frame(
+            {
+                "webSearchQueries": ["who won the 2026 world cup final"],
+                "groundingChunks": [{"web": {"uri": "https://example.com"}}],
+            }
+        )
+    )
+
+    assert input_details.get("web_search_requests") == 1, "a grounded turn must report its query"
+    assert input_details.get("text_tokens") == 19, "the modality breakdown must survive alongside it"
+
+
+def test_gemini_realtime_response_done_reports_no_grounding_when_none_ran():
+    """The counter must stay unset on an ordinary turn, or every session pays a grounding fee."""
+    input_details = _response_done_input_details(_grounded_live_frame(None))
+
+    assert input_details.get("web_search_requests") is None
+    assert input_details.get("google_maps_grounding_requests") is None
diff --git a/tests/test_litellm/proxy/client/cli/test_statusline_script.py b/tests/test_litellm/proxy/client/cli/test_statusline_script.py
index 5c0cf6b5703..39d0e24d7b0 100644
--- a/tests/test_litellm/proxy/client/cli/test_statusline_script.py
+++ b/tests/test_litellm/proxy/client/cli/test_statusline_script.py
@@ -252,11 +252,52 @@ class TestRender:
     def test_savings_header_and_bars_against_the_routers_baseline(self, config_dir):
         text = render("claude-sonnet-5", RECORDED, config_dir, use_color=False, bar_width=10)
         assert text.splitlines() == [
-            "claude-auto · Routed to: claude-sonnet-5  -63% vs Claude Opus 5",
-            "LiteLLM       ████░░░░░░ $0.14",
+            "Routed to: claude-sonnet-5  -63% vs Claude Opus 5",
+            "claude-auto   ████░░░░░░ $0.14",
             "Claude Opus 5 ██████████ $0.38",
         ]
 
+    def test_a_long_router_name_keeps_both_cost_bars_aligned(self, config_dir: Path) -> None:
+        session: Final = RECORDED._replace(router_name="engineering-smart-router")
+        text: Final = render("claude-sonnet-5", session, config_dir, use_color=False, bar_width=10)
+        assert text.splitlines()[1:] == [
+            "engineering-smart-router ████░░░░░░ $0.14",
+            "Claude Opus 5            ██████████ $0.38",
+        ]
+
+    @pytest.mark.parametrize(
+        ("router_name", "baseline_name", "router_padding", "baseline_padding"),
+        (
+            ("路由-router", "Claude Opus 5", 3, 1),
+            ("智能模型路由器", "Claude Opus 5", 1, 2),
+            ("ＡＢＣ-router", "Claude Opus 5", 1, 1),
+            ("cafe\u0301-router", "Claude Opus 5", 3, 1),
+            ("a\u20dd-router", "Claude Opus 5", 6, 1),
+            ("カ\u3099-router", "Claude Opus 5", 5, 1),
+            ("auto", "基準モデル", 7, 1),
+            ("auto", "cafe\u0301", 1, 1),
+        ),
+    )
+    @pytest.mark.parametrize("use_color", (False, True))
+    def test_unicode_labels_align_cost_bars_by_terminal_columns(
+        self,
+        config_dir: Path,
+        router_name: str,
+        baseline_name: str,
+        router_padding: int,
+        baseline_padding: int,
+        use_color: bool,
+    ) -> None:
+        (config_dir / "cache" / "gateway-models.json").write_text(
+            json.dumps({"models": [{"id": "claude-opus-5", "display_name": baseline_name}]})
+        )
+        session: Final = RECORDED._replace(router_name=router_name)
+        text: Final = ANSI.sub("", render("claude-sonnet-5", session, config_dir, use_color, bar_width=10))
+        assert text.splitlines()[1:] == [
+            f"{router_name}{' ' * router_padding}████░░░░░░ $0.14",
+            f"{baseline_name}{' ' * baseline_padding}██████████ $0.38",
+        ]
+
     def test_control_characters_in_any_externally_sourced_label_never_reach_the_terminal(self, tmp_path, config_dir):
         # The transcript, the proxy payload and Claude Code's model cache all feed labels straight into a
         # terminal, and none is under this script's control. Only the control bytes are dropped (ESC, BEL,
@@ -289,7 +330,7 @@ class TestRender:
         assert "+25% vs Claude Opus 5" in render("m", dearer, config_dir, use_color=False)
 
     def test_without_a_baseline_only_the_routed_line_shows(self, config_dir):
-        assert render("m", RECORDED._replace(baseline_model=None), config_dir, False) == "claude-auto · Routed to: m"
+        assert render("m", RECORDED._replace(baseline_model=None), config_dir, False) == "Routed to: m"
         assert render("m", None, config_dir, False) == "Routed to: m"
 
     def test_color_wraps_the_same_text(self, config_dir):
@@ -311,7 +352,8 @@ class TestClaudeCodeMode:
             return Fetched(RECORDED, definitive=True)
 
         text: Final = _run(_payload(transcript), _env(tmp_path, config_dir), fetch)
-        assert text.startswith("claude-auto · Routed to: claude-sonnet-5  -63% vs Claude Opus 5\n")
+        assert text.startswith("Routed to: claude-sonnet-5  -63% vs Claude Opus 5\n")
+        assert text.splitlines()[1].startswith("claude-auto ")
 
     def test_a_discovered_display_name_labels_the_sessions_model(
         self, tmp_path: Path, transcript: Path, config_dir: Path
@@ -322,7 +364,7 @@ class TestClaudeCodeMode:
             return Fetched(session, definitive=True)
 
         text: Final = _run(_payload(transcript), _env(tmp_path, config_dir), fetch)
-        assert text.startswith("claude-auto · Routed to: Claude Opus 5  -63% vs Claude Opus 5\n")
+        assert text.startswith("Routed to: Claude Opus 5  -63% vs Claude Opus 5\n")
 
     def test_an_unrecorded_session_degrades_to_the_routed_line(self, tmp_path, transcript, config_dir):
         assert _run(_payload(transcript), _env(tmp_path, config_dir), lambda c, s: Fetched(None, True)) == (
@@ -378,7 +420,8 @@ class TestCodexMode:
 
         out = _run({"hook_event_name": "Stop", "session_id": SESSION_ID, "transcript_path": "/nope"}, env, fetch)
         message = json.loads(out)["systemMessage"]
-        assert message.splitlines()[1] == "claude-auto · Routed to: claude-sonnet-5  -63% vs Claude Opus 5"
+        assert message.splitlines()[1] == "Routed to: claude-sonnet-5  -63% vs Claude Opus 5"
+        assert message.splitlines()[2].startswith("claude-auto ")
         assert message.startswith("\n")
         assert seen == [Credentials("http://127.0.0.1:4000", "sk-codex")]
 
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 3d7c6e06d94..f25727ebd9a 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
@@ -4620,46 +4620,27 @@ class TestPanwAirsLatestRoleMessageOnly:
 
     @pytest.mark.asyncio
     async def test_anthropic_system_plus_multiturn_no_fallback(self):
-        """Anthropic with top-level system + multi-turn messages[]
-        — latest-user works, no scan-all fallback.
+        """Anthropic with a top-level system prompt and multi-turn messages[]
+        scans only the latest user turn, with no scan-all fallback.
 
-        Key scenario: Anthropic top-level `system` field causes
-        structured_messages to have an injected system entry, but
-        request_data["messages"] does NOT include it.
+        The Anthropic handler hoists the top-level `system` field into both
+        `texts` and `structured_messages`, so the latest-user walk has to
+        count the same entries the framework flattened.
         """
-        handler = PanwPrismaAirsHandler(
-            guardrail_name="test_panw_airs",
-            api_key="test_api_key",
-            profile_name="test_profile",
-            default_on=True,
+        from litellm.llms.anthropic.chat.guardrail_translation.handler import (
+            AnthropicMessagesHandler,
         )
 
-        # Original Anthropic messages (no system in messages array)
-        original_messages = [
-            {"role": "user", "content": "First user turn"},
-            {"role": "assistant", "content": "First assistant turn"},
-            {"role": "user", "content": "Latest user turn"},
-        ]
-
-        # texts extracted from original_messages (3 text entries)
-        texts = ["First user turn", "First assistant turn", "Latest user turn"]
-
-        # structured_messages has an INJECTED system message from translation
-        structured_messages = [
-            {"role": "system", "content": "You are a helpful assistant."},
-            {"role": "user", "content": "First user turn"},
-            {"role": "assistant", "content": "First assistant turn"},
-            {"role": "user", "content": "Latest user turn"},
-        ]
-
-        inputs: GenericGuardrailAPIInputs = {
-            "texts": texts,
-            "structured_messages": structured_messages,
-        }
+        handler = make_handler()
         request_data = {
             "litellm_call_id": "test-call-id",
             "model": "anthropic/claude-sonnet-4-20250514",
-            "messages": original_messages,
+            "system": "You are a helpful assistant.",
+            "messages": [
+                {"role": "user", "content": "First user turn"},
+                {"role": "assistant", "content": "First assistant turn"},
+                {"role": "user", "content": "Latest user turn"},
+            ],
             "proxy_server_request": {
                 "url": "http://localhost:4000/v1/messages",
             },
@@ -4670,13 +4651,11 @@ class TestPanwAirsLatestRoleMessageOnly:
         ) as mock_api:
             mock_api.return_value = {"action": "allow", "category": "benign"}
 
-            await handler.apply_guardrail(
-                inputs=inputs,
-                request_data=request_data,
-                input_type="request",
+            await AnthropicMessagesHandler().process_input_messages(
+                data=request_data,
+                guardrail_to_apply=handler,
             )
 
-            # Should scan ONLY the latest user message, not fall back to scan-all
             assert mock_api.call_count == 1
             assert mock_api.call_args.kwargs["content"] == "Latest user turn"
 
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 ec3adcf3609..3c6e70ccd0d 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
@@ -1,3 +1,5 @@
+from collections.abc import Mapping
+from contextlib import ExitStack
 from typing import Final
 import asyncio
 from types import SimpleNamespace
@@ -22,28 +24,36 @@ from litellm.proxy._types import (
     LoggingCallbackStatus,
     NewUserRequest,
     LiteLLM_BudgetTable,
+    LiteLLM_ObjectPermissionBase,
     LiteLLM_OrganizationTable,
     LiteLLM_ProjectTableCachedObj,
     LiteLLM_TeamTable,
     LiteLLM_TeamTableCachedObj,
     LiteLLM_UserTable,
     LiteLLM_VerificationToken,
+    LiteLLMKeyType,
     LitellmUserRoles,
     Member,
     ProxyException,
-    ResetSpendRequest,
     RegenerateKeyRequest,
+    ResetSpendRequest,
     UpdateKeyRequest,
 )
+from litellm.models.object_permission import LiteLLM_ObjectPermissionTable
 from litellm.proxy.auth.auth_checks import _delete_cache_key_object, _project_cache_key
 from litellm.proxy.auth.user_api_key_auth import UserAPIKeyAuth
 from litellm.proxy.common_utils.user_api_key_cache import UserApiKeyCache
+from litellm.litellm_core_utils.duration_parser import duration_in_seconds
 from litellm.proxy.management_endpoints.key_management_endpoints import (
     _check_org_key_limits,
     _check_project_key_limits,
     _check_team_key_limits,
     _common_key_generation_helper,
+    _effective_key_after_update,
+    _effective_key_for_generate,
+    _enforce_custom_key_policy,
     _enforce_upperbound_key_params,
+    _execute_virtual_key_regeneration,
     _get_and_validate_existing_key,
     _list_key_helper,
     _persist_deleted_verification_tokens,
@@ -68,6 +78,7 @@ from litellm.proxy.management_endpoints.key_management_endpoints import (
     validate_key_team_change,
 )
 from litellm.proxy.proxy_server import ProxyConfig, app
+from litellm.types.proxy.management_endpoints.key_management_endpoints import CustomKeyPolicyRequest
 
 client = TestClient(app)
 
@@ -1032,7 +1043,7 @@ async def test_key_generation_with_mcp_tool_permissions(monkeypatch):
 
 
 @pytest.mark.asyncio
-async def test_key_update_object_permissions_existing_permission(monkeypatch):
+async def test_key_update_object_permissions_existing_permission():
     """
     Test updating object permissions when a key already has an existing object_permission_id.
 
@@ -1052,9 +1063,7 @@ async def test_key_update_object_permissions_existing_permission(monkeypatch):
         _handle_update_object_permission,
     )
 
-    # Mock prisma client
     mock_prisma_client = AsyncMock()
-    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", mock_prisma_client)
 
     # Mock existing key with object_permission_id
     existing_key_row = LiteLLM_VerificationToken(
@@ -1094,6 +1103,7 @@ async def test_key_update_object_permissions_existing_permission(monkeypatch):
     result = await _handle_update_object_permission(
         data_json=data_json,
         existing_key_row=existing_key_row,
+        prisma_client=mock_prisma_client,
     )
 
     # Verify the object_permission was removed from data_json and object_permission_id was set
@@ -1108,7 +1118,7 @@ async def test_key_update_object_permissions_existing_permission(monkeypatch):
 
 
 @pytest.mark.asyncio
-async def test_key_update_object_permissions_no_existing_permission(monkeypatch):
+async def test_key_update_object_permissions_no_existing_permission():
     """
     Test creating object permissions when a key has no existing object_permission_id.
 
@@ -1128,9 +1138,7 @@ async def test_key_update_object_permissions_no_existing_permission(monkeypatch)
         _handle_update_object_permission,
     )
 
-    # Mock prisma client
     mock_prisma_client = AsyncMock()
-    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", mock_prisma_client)
 
     existing_key_row_no_perm = LiteLLM_VerificationToken(
         token="test_token_hash_2",
@@ -1161,6 +1169,7 @@ async def test_key_update_object_permissions_no_existing_permission(monkeypatch)
     result = await _handle_update_object_permission(
         data_json=data_json,
         existing_key_row=existing_key_row_no_perm,
+        prisma_client=mock_prisma_client,
     )
 
     # Verify new object_permission_id was set
@@ -1171,7 +1180,7 @@ async def test_key_update_object_permissions_no_existing_permission(monkeypatch)
 
 
 @pytest.mark.asyncio
-async def test_key_update_object_permissions_missing_permission_record(monkeypatch):
+async def test_key_update_object_permissions_missing_permission_record():
     """
     Test creating object permissions when existing object_permission_id record is not found.
 
@@ -1191,9 +1200,7 @@ async def test_key_update_object_permissions_missing_permission_record(monkeypat
         _handle_update_object_permission,
     )
 
-    # Mock prisma client
     mock_prisma_client = AsyncMock()
-    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", mock_prisma_client)
 
     existing_key_row_missing_perm = LiteLLM_VerificationToken(
         token="test_token_hash_3",
@@ -1224,6 +1231,7 @@ async def test_key_update_object_permissions_missing_permission_record(monkeypat
     result = await _handle_update_object_permission(
         data_json=data_json,
         existing_key_row=existing_key_row_missing_perm,
+        prisma_client=mock_prisma_client,
     )
 
     # Verify new object_permission_id was set
@@ -11985,6 +11993,10 @@ async def test_execute_virtual_key_regeneration_rejects_over_limit_duration(monk
             "litellm.proxy.management_endpoints.key_management_endpoints._insert_deprecated_key",
             new_callable=AsyncMock,
         ),
+        patch(  # test-quality-ok: archival path is outside upperbound rejection
+            "litellm.proxy.management_endpoints.key_management_endpoints._persist_deleted_verification_tokens",
+            new_callable=AsyncMock,
+        ) as persist_deleted_verification_tokens,
         patch(
             "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
             new_callable=AsyncMock,
@@ -12005,6 +12017,7 @@ async def test_execute_virtual_key_regeneration_rejects_over_limit_duration(monk
     assert exc_info.value.status_code == 400
     assert "duration" in str(exc_info.value.detail)
     # Rejected regenerate must not reach the DB update.
+    persist_deleted_verification_tokens.assert_not_awaited()
     assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 0
 
 
@@ -12064,6 +12077,1011 @@ async def test_execute_virtual_key_regeneration_allows_within_limit_duration(mon
     assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 1
 
 
+@pytest.mark.asyncio
+async def test_execute_virtual_key_regeneration_rejects_when_custom_key_update_hook_denies():
+    existing_key = _make_regenerate_existing_key()
+    data = RegenerateKeyRequest(duration="3000d")
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    received_data: list[UpdateKeyRequest] = []
+
+    async def hook(data: UpdateKeyRequest) -> dict[str, object]:
+        received_data.append(data)
+        if data.duration and duration_in_seconds(data.duration) > duration_in_seconds("7d"):
+            return {"decision": False, "message": "duration must be <= 7d"}
+        return {"decision": True}
+
+    with (
+        patch(  # test-quality-ok: deterministic token setup for policy rejection
+            "litellm.proxy.management_endpoints.key_management_endpoints.get_new_token",
+            new_callable=AsyncMock,
+            return_value="sk-newtoken1234ab12",
+        ),
+        patch(  # test-quality-ok: grace-period path is outside policy rejection
+            "litellm.proxy.management_endpoints.key_management_endpoints._insert_deprecated_key",
+            new_callable=AsyncMock,
+        ) as insert_deprecated_key,
+        patch(  # test-quality-ok: archival path is outside policy rejection
+            "litellm.proxy.management_endpoints.key_management_endpoints._persist_deleted_verification_tokens",
+            new_callable=AsyncMock,
+        ) as persist_deleted_verification_tokens,
+        patch(  # test-quality-ok: cache eviction is outside policy rejection
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: rotation callback is outside policy rejection
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_rotated_hook",
+            new_callable=AsyncMock,
+        ),
+        patch("litellm.proxy.proxy_server.user_custom_key_update", hook),  # test-quality-ok: inject policy hook
+    ):
+        with pytest.raises(HTTPException) as exc_info:
+            await _execute_virtual_key_regeneration(
+                prisma_client=mock_prisma_client,
+                key_in_db=existing_key,
+                hashed_api_key="abc123",
+                key="abc123",
+                data=data,
+                user_api_key_dict=_make_regenerate_user_api_key_dict(),
+                litellm_changed_by=None,
+                user_api_key_cache=MagicMock(),
+                proxy_logging_obj=MagicMock(),
+            )
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail == "duration must be <= 7d"
+    insert_deprecated_key.assert_not_awaited()
+    persist_deleted_verification_tokens.assert_not_awaited()
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 0
+    assert len(received_data) == 1
+    assert received_data[0].key == "abc123"
+    assert received_data[0].duration == "3000d"
+
+
+@pytest.mark.asyncio
+async def test_execute_virtual_key_regeneration_allows_when_custom_key_update_hook_approves():
+    existing_key = _make_regenerate_existing_key()
+    data = RegenerateKeyRequest(duration="5d")
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    received_data: list[UpdateKeyRequest] = []
+
+    async def hook(data: UpdateKeyRequest) -> dict[str, object]:
+        received_data.append(data)
+        if data.duration and duration_in_seconds(data.duration) > duration_in_seconds("7d"):
+            return {"decision": False, "message": "duration must be <= 7d"}
+        return {"decision": True}
+
+    with (
+        patch(  # test-quality-ok: deterministic token setup for policy approval
+            "litellm.proxy.management_endpoints.key_management_endpoints.get_new_token",
+            new_callable=AsyncMock,
+            return_value="sk-newtoken1234ab12",
+        ),
+        patch(  # test-quality-ok: grace-period path is outside policy approval
+            "litellm.proxy.management_endpoints.key_management_endpoints._insert_deprecated_key",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: verify archival follows policy approval
+            "litellm.proxy.management_endpoints.key_management_endpoints._persist_deleted_verification_tokens",
+            new_callable=AsyncMock,
+        ) as persist_deleted_verification_tokens,
+        patch(  # test-quality-ok: cache eviction is outside policy approval
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: rotation callback is outside policy approval
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_rotated_hook",
+            new_callable=AsyncMock,
+        ),
+        patch("litellm.proxy.proxy_server.user_custom_key_update", hook),  # test-quality-ok: inject policy hook
+    ):
+        await _execute_virtual_key_regeneration(
+            prisma_client=mock_prisma_client,
+            key_in_db=existing_key,
+            hashed_api_key="abc123",
+            key="abc123",
+            data=data,
+            user_api_key_dict=_make_regenerate_user_api_key_dict(),
+            litellm_changed_by=None,
+            user_api_key_cache=MagicMock(),
+            proxy_logging_obj=MagicMock(),
+        )
+
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 1
+    persist_deleted_verification_tokens.assert_awaited_once()
+    assert persist_deleted_verification_tokens.call_args.kwargs["keys"] == [existing_key]
+    assert len(received_data) == 1
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "data",
+    [None, RegenerateKeyRequest(), RegenerateKeyRequest(duration=""), RegenerateKeyRequest(budget_duration="")],
+)
+async def test_execute_virtual_key_regeneration_skips_custom_key_update_hook_without_changes(data):
+    mock_prisma_client = _make_regenerate_mock_prisma()
+
+    async def hook(data: UpdateKeyRequest) -> dict[str, object]:
+        raise AssertionError(f"custom key update hook called with {data}")
+
+    with (
+        patch(  # test-quality-ok: deterministic token setup for unchanged request
+            "litellm.proxy.management_endpoints.key_management_endpoints.get_new_token",
+            new_callable=AsyncMock,
+            return_value="sk-newtoken1234ab12",
+        ),
+        patch(  # test-quality-ok: grace-period path is outside unchanged request
+            "litellm.proxy.management_endpoints.key_management_endpoints._insert_deprecated_key",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: cache eviction is outside unchanged request
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: rotation callback is outside unchanged request
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_rotated_hook",
+            new_callable=AsyncMock,
+        ),
+        patch("litellm.proxy.proxy_server.user_custom_key_update", hook),  # test-quality-ok: inject policy hook
+    ):
+        await _execute_virtual_key_regeneration(
+            prisma_client=mock_prisma_client,
+            key_in_db=_make_regenerate_existing_key(),
+            hashed_api_key="abc123",
+            key="abc123",
+            data=data,
+            user_api_key_dict=_make_regenerate_user_api_key_dict(),
+            litellm_changed_by=None,
+            user_api_key_cache=MagicMock(),
+            proxy_logging_obj=MagicMock(),
+        )
+
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 1
+
+
+@pytest.mark.asyncio
+async def test_execute_virtual_key_regeneration_hides_the_untouched_modal_expiry_from_the_custom_key_update_hook():
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    untouched_modal_body = RegenerateKeyRequest(
+        key_alias=None, max_budget=None, tpm_limit=None, rpm_limit=None, duration="", grace_period=""
+    )
+    received_data: list[UpdateKeyRequest] = []
+
+    async def hook(data: UpdateKeyRequest) -> dict[str, object]:
+        received_data.append(data)
+        if data.duration is not None and duration_in_seconds(data.duration) > duration_in_seconds("7d"):
+            return {"decision": False, "message": "duration must be <= 7d"}
+        return {"decision": True}
+
+    with (
+        patch(  # test-quality-ok: deterministic token setup for the untouched modal body
+            "litellm.proxy.management_endpoints.key_management_endpoints.get_new_token",
+            new_callable=AsyncMock,
+            return_value="sk-newtoken1234ab12",
+        ),
+        patch(  # test-quality-ok: grace-period path is outside the hook input
+            "litellm.proxy.management_endpoints.key_management_endpoints._insert_deprecated_key",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: cache eviction is outside the hook input
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: rotation callback is outside the hook input
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_rotated_hook",
+            new_callable=AsyncMock,
+        ),
+        patch("litellm.proxy.proxy_server.user_custom_key_update", hook),  # test-quality-ok: inject policy hook
+    ):
+        await _execute_virtual_key_regeneration(
+            prisma_client=mock_prisma_client,
+            key_in_db=_make_regenerate_existing_key(),
+            hashed_api_key="abc123",
+            key="abc123",
+            data=untouched_modal_body,
+            user_api_key_dict=_make_regenerate_user_api_key_dict(),
+            litellm_changed_by=None,
+            user_api_key_cache=MagicMock(),
+            proxy_logging_obj=MagicMock(),
+        )
+
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 1
+    assert len(received_data) == 1
+    assert "duration" not in received_data[0].model_fields_set
+    assert received_data[0].model_fields_set >= {"key", "key_alias", "max_budget", "tpm_limit", "rpm_limit"}
+
+
+_POLICY_DENIAL_MESSAGE = "key duration must be 7d or less"
+_POLICY_HASHED_TOKEN = "0d62f396c1317066f55a96086517047c737087c61eb2bf016b72e6298927b15b"
+_POLICY_GENERATED_KEY = {"key": "sk-test-key", "expires": None, "user_id": "test-user", "team_id": None}
+
+
+def _seven_day_policy(received: list[CustomKeyPolicyRequest]):
+    async def policy(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        received.append(policy_request)
+        expires = policy_request.effective_key.expires
+        if isinstance(expires, datetime) and expires > datetime.now(timezone.utc) + timedelta(days=7):
+            return {"decision": False, "message": _POLICY_DENIAL_MESSAGE}
+        return {"decision": True}
+
+    return policy
+
+
+def _assert_expires_in(effective_key: LiteLLM_VerificationToken, duration: str) -> None:
+    expires = effective_key.expires
+    assert isinstance(expires, datetime)
+    assert expires.tzinfo is not None
+    expected = datetime.now(timezone.utc) + timedelta(seconds=duration_in_seconds(duration=duration))
+    assert abs((expires - expected).total_seconds()) < 60
+
+
+def _regenerate_policy_mocks(policy, insert_deprecated_key: AsyncMock, persist: AsyncMock) -> ExitStack:
+    stack = ExitStack()
+    stack.enter_context(
+        patch(  # test-quality-ok: deterministic token setup for the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints.get_new_token",
+            new_callable=AsyncMock,
+            return_value="sk-newtoken1234ab12",
+        )
+    )
+    stack.enter_context(
+        patch(  # test-quality-ok: grace-period write must not run on a denied regenerate
+            "litellm.proxy.management_endpoints.key_management_endpoints._insert_deprecated_key",
+            insert_deprecated_key,
+        )
+    )
+    stack.enter_context(
+        patch(  # test-quality-ok: archival write must not run on a denied regenerate
+            "litellm.proxy.management_endpoints.key_management_endpoints._persist_deleted_verification_tokens",
+            persist,
+        )
+    )
+    stack.enter_context(
+        patch(  # test-quality-ok: cache eviction is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        )
+    )
+    stack.enter_context(
+        patch(  # test-quality-ok: rotation callback is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_rotated_hook",
+            new_callable=AsyncMock,
+        )
+    )
+    stack.enter_context(
+        patch("litellm.proxy.proxy_server.user_custom_key_policy", policy)  # test-quality-ok: inject policy hook
+    )
+    return stack
+
+
+async def _regenerate_under_policy(mock_prisma_client, existing_key, data):
+    return await _execute_virtual_key_regeneration(
+        prisma_client=mock_prisma_client,
+        key_in_db=existing_key,
+        hashed_api_key="abc123",
+        key="abc123",
+        data=data,
+        user_api_key_dict=_make_regenerate_user_api_key_dict(),
+        litellm_changed_by=None,
+        user_api_key_cache=MagicMock(),
+        proxy_logging_obj=MagicMock(),
+    )
+
+
+@pytest.mark.asyncio
+async def test_regenerate_rejects_when_custom_key_policy_denies_the_effective_expiry():
+    existing_key = _make_regenerate_existing_key()
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    received: list[CustomKeyPolicyRequest] = []
+    insert_deprecated_key = AsyncMock()
+    persist = AsyncMock()
+
+    with _regenerate_policy_mocks(_seven_day_policy(received), insert_deprecated_key, persist):
+        with pytest.raises(HTTPException) as exc_info:
+            await _regenerate_under_policy(mock_prisma_client, existing_key, RegenerateKeyRequest(duration="3000d"))
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail == _POLICY_DENIAL_MESSAGE
+    insert_deprecated_key.assert_not_awaited()
+    persist.assert_not_awaited()
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 0
+    assert [policy_request.operation for policy_request in received] == ["regenerate"]
+    assert received[0].existing_key is not None
+    assert received[0].existing_key.token == "abc123"
+    assert isinstance(received[0].request, RegenerateKeyRequest)
+    assert received[0].request.duration == "3000d"
+    _assert_expires_in(received[0].effective_key, "3000d")
+
+
+@pytest.mark.asyncio
+async def test_regenerate_within_custom_key_policy_rotates_the_key():
+    existing_key = _make_regenerate_existing_key()
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    received: list[CustomKeyPolicyRequest] = []
+    persist = AsyncMock()
+
+    with _regenerate_policy_mocks(_seven_day_policy(received), AsyncMock(), persist):
+        await _regenerate_under_policy(mock_prisma_client, existing_key, RegenerateKeyRequest(duration="5d"))
+
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 1
+    persist.assert_awaited_once()
+    assert persist.call_args.kwargs["keys"] == [existing_key]
+    assert [policy_request.operation for policy_request in received] == ["regenerate"]
+    _assert_expires_in(received[0].effective_key, "5d")
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("data", [None, RegenerateKeyRequest()])
+async def test_regenerate_without_changes_still_runs_custom_key_policy(data):
+    existing_key = _make_regenerate_existing_key()
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    received: list[CustomKeyPolicyRequest] = []
+
+    async def freeze_rotation(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        received.append(policy_request)
+        return {"decision": False, "message": "key rotation is frozen"}
+
+    with _regenerate_policy_mocks(freeze_rotation, AsyncMock(), AsyncMock()):
+        with pytest.raises(HTTPException) as exc_info:
+            await _regenerate_under_policy(mock_prisma_client, existing_key, data)
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail == "key rotation is frozen"
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 0
+    assert [policy_request.operation for policy_request in received] == ["regenerate"]
+    assert received[0].existing_key == existing_key
+    assert received[0].effective_key == existing_key
+
+
+def _policy_existing_team_key() -> LiteLLM_VerificationToken:
+    return LiteLLM_VerificationToken(
+        token=_POLICY_HASHED_TOKEN, user_id="test-user", team_id="team-a", max_budget=200.0
+    )
+
+
+def _setup_update_key_fn_policy_mocks(monkeypatch, existing_key: LiteLLM_VerificationToken) -> AsyncMock:
+    mock_prisma_client = AsyncMock()
+    mock_prisma_client.db.litellm_verificationtoken.find_unique = AsyncMock(return_value=existing_key)
+    mock_prisma_client.db.litellm_verificationtoken.find_first = AsyncMock(return_value=None)
+    mock_prisma_client.update_data = AsyncMock(return_value={"data": {"max_budget": 50.0, "team_id": "team-a"}})
+    _setup_update_key_mocks(monkeypatch, mock_prisma_client)
+    monkeypatch.setattr(
+        "litellm.proxy.management_endpoints.key_management_endpoints.get_team_object", AsyncMock(return_value=None)
+    )
+    return mock_prisma_client
+
+
+def _assert_update_policy_request(policy_request: CustomKeyPolicyRequest, request: UpdateKeyRequest) -> None:
+    assert policy_request.operation == "update"
+    assert policy_request.request is request
+    assert policy_request.existing_key is not None
+    assert policy_request.existing_key.max_budget == 200.0
+    assert policy_request.effective_key.team_id == "team-a"
+    assert policy_request.effective_key.user_id == "test-user"
+    assert policy_request.effective_key.max_budget == 50.0
+    _assert_expires_in(policy_request.effective_key, request.duration or "")
+
+
+@pytest.mark.asyncio
+async def test_update_key_fn_runs_custom_key_policy_on_the_effective_row(monkeypatch):
+    from litellm.proxy.management_endpoints.key_management_endpoints import update_key_fn
+
+    mock_prisma_client = _setup_update_key_fn_policy_mocks(monkeypatch, _policy_existing_team_key())
+    received: list[CustomKeyPolicyRequest] = []
+    policy = _seven_day_policy(received)
+    data = UpdateKeyRequest(
+        key=_POLICY_HASHED_TOKEN, duration="5d", max_budget=50.0, auto_rotate=True, rotation_interval="30d"
+    )
+
+    with (
+        patch(  # test-quality-ok: cache eviction is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch("litellm.proxy.proxy_server.user_custom_key_policy", policy),  # test-quality-ok: inject policy hook
+    ):
+        await update_key_fn(
+            request=MagicMock(),
+            data=data,
+            user_api_key_dict=_make_regenerate_user_api_key_dict(),
+            litellm_changed_by=None,
+        )
+
+    mock_prisma_client.update_data.assert_awaited_once()
+    assert len(received) == 1
+    _assert_update_policy_request(received[0], data)
+    key_rotation_at = received[0].effective_key.key_rotation_at
+    assert key_rotation_at is not None
+    assert abs(key_rotation_at - (datetime.now(timezone.utc) + timedelta(days=30))) < timedelta(seconds=60)
+
+
+@pytest.mark.asyncio
+async def test_update_key_fn_rejects_when_custom_key_policy_denies(monkeypatch):
+    from litellm.proxy.management_endpoints.key_management_endpoints import update_key_fn
+
+    mock_prisma_client = _setup_update_key_fn_policy_mocks(monkeypatch, _policy_existing_team_key())
+    received: list[CustomKeyPolicyRequest] = []
+    policy = _seven_day_policy(received)
+
+    with patch("litellm.proxy.proxy_server.user_custom_key_policy", policy):  # test-quality-ok: inject policy hook
+        with pytest.raises(ProxyException) as exc_info:
+            await update_key_fn(
+                request=MagicMock(),
+                data=UpdateKeyRequest(key=_POLICY_HASHED_TOKEN, duration="3000d", max_budget=50.0),
+                user_api_key_dict=_make_regenerate_user_api_key_dict(),
+                litellm_changed_by=None,
+            )
+
+    assert str(exc_info.value.code) == "403"
+    assert exc_info.value.message == _POLICY_DENIAL_MESSAGE
+    mock_prisma_client.update_data.assert_not_awaited()
+    assert [policy_request.operation for policy_request in received] == ["update"]
+    _assert_expires_in(received[0].effective_key, "3000d")
+
+
+async def _process_single_key_update_under_policy(prisma_client: AsyncMock, data: UpdateKeyRequest, policy):
+    with (
+        patch(  # test-quality-ok: cache eviction is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: update callback is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_updated_hook",
+            new_callable=AsyncMock,
+        ),
+    ):
+        return await _process_single_key_update(
+            update_key_request=data,
+            user_api_key_dict=_make_regenerate_user_api_key_dict(),
+            litellm_changed_by=None,
+            prisma_client=prisma_client,
+            user_api_key_cache=MagicMock(),
+            proxy_logging_obj=MagicMock(),
+            llm_router=None,
+            existing_key_row=_policy_existing_team_key(),
+            user_custom_key_policy=policy,
+        )
+
+
+@pytest.mark.asyncio
+async def test_process_single_key_update_runs_custom_key_policy_on_the_effective_row():
+    mock_prisma_client = AsyncMock()
+    updated_row = MagicMock()
+    updated_row.model_dump.return_value = {"max_budget": 50.0, "team_id": "team-a"}
+    mock_prisma_client.update_data = AsyncMock(return_value={"data": updated_row})
+    received: list[CustomKeyPolicyRequest] = []
+    data = UpdateKeyRequest(key=_POLICY_HASHED_TOKEN, duration="5d", max_budget=50.0)
+
+    result = await _process_single_key_update_under_policy(mock_prisma_client, data, _seven_day_policy(received))
+
+    assert result["max_budget"] == 50.0
+    mock_prisma_client.update_data.assert_awaited_once()
+    assert len(received) == 1
+    _assert_update_policy_request(received[0], data)
+
+
+@pytest.mark.asyncio
+async def test_process_single_key_update_rejects_when_custom_key_policy_denies():
+    mock_prisma_client = AsyncMock()
+    mock_prisma_client.update_data = AsyncMock()
+    received: list[CustomKeyPolicyRequest] = []
+    data = UpdateKeyRequest(key=_POLICY_HASHED_TOKEN, duration="3000d", max_budget=50.0)
+
+    with pytest.raises(HTTPException) as exc_info:
+        await _process_single_key_update_under_policy(mock_prisma_client, data, _seven_day_policy(received))
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail == _POLICY_DENIAL_MESSAGE
+    mock_prisma_client.update_data.assert_not_awaited()
+    assert [policy_request.operation for policy_request in received] == ["update"]
+
+
+_OBJECT_PERMISSION_ID_AFTER_POLICY = "perm-after-policy"
+
+
+def _record_object_permission_writes(mock_prisma_client: AsyncMock, events: list[str]) -> None:
+    mock_prisma_client.db.litellm_objectpermissiontable.find_unique = AsyncMock(return_value=None)
+
+    async def upsert(**_kwargs: object) -> MagicMock:
+        events.append("permission row upsert")
+        return MagicMock(object_permission_id=_OBJECT_PERMISSION_ID_AFTER_POLICY)
+
+    mock_prisma_client.db.litellm_objectpermissiontable.upsert = AsyncMock(side_effect=upsert)
+
+
+def _recording_policy(events: list[str], allowed: bool):
+    async def policy(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        events.append("policy")
+        return {"decision": allowed, "message": "key max_budget must be 1000 or less"}
+
+    return policy
+
+
+def _assert_permission_row_written_after_policy(events: list[str], written: Mapping[str, object]) -> None:
+    assert events == ["policy", "permission row upsert"]
+    assert written["object_permission_id"] == _OBJECT_PERMISSION_ID_AFTER_POLICY
+    assert "object_permission" not in written
+
+
+def _assert_permission_row_untouched(mock_prisma_client: AsyncMock, events: list[str]) -> None:
+    assert events == ["policy"]
+    mock_prisma_client.db.litellm_objectpermissiontable.upsert.assert_not_awaited()
+
+
+def _update_with_object_permission(max_budget: float) -> UpdateKeyRequest:
+    return UpdateKeyRequest(
+        key=_POLICY_HASHED_TOKEN,
+        max_budget=max_budget,
+        object_permission=LiteLLM_ObjectPermissionBase(vector_stores=["vs-1"]),
+    )
+
+
+def _setup_update_key_fn_object_permission_mocks(monkeypatch, allowed: bool) -> tuple[AsyncMock, list[str]]:
+    mock_prisma_client = _setup_update_key_fn_policy_mocks(monkeypatch, _policy_existing_team_key())
+    events: list[str] = []
+    _record_object_permission_writes(mock_prisma_client, events)
+    monkeypatch.setattr("litellm.proxy.proxy_server.user_custom_key_policy", _recording_policy(events, allowed))
+    monkeypatch.setattr(
+        "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object", AsyncMock()
+    )
+    return mock_prisma_client, events
+
+
+async def _update_key_fn_with_object_permission(max_budget: float):
+    from litellm.proxy.management_endpoints.key_management_endpoints import update_key_fn
+
+    return await update_key_fn(
+        request=MagicMock(),
+        data=_update_with_object_permission(max_budget=max_budget),
+        user_api_key_dict=_make_regenerate_user_api_key_dict(),
+        litellm_changed_by=None,
+    )
+
+
+@pytest.mark.asyncio
+async def test_update_key_fn_writes_the_object_permission_row_only_after_the_policy_allows(monkeypatch):
+    mock_prisma_client, events = _setup_update_key_fn_object_permission_mocks(monkeypatch, allowed=True)
+
+    await _update_key_fn_with_object_permission(max_budget=50.0)
+
+    _assert_permission_row_written_after_policy(events, mock_prisma_client.update_data.await_args.kwargs["data"])
+
+
+@pytest.mark.asyncio
+async def test_update_key_fn_denied_by_the_policy_leaves_the_object_permission_row_untouched(monkeypatch):
+    mock_prisma_client, events = _setup_update_key_fn_object_permission_mocks(monkeypatch, allowed=False)
+
+    with pytest.raises(ProxyException) as exc_info:
+        await _update_key_fn_with_object_permission(max_budget=5000.0)
+
+    assert str(exc_info.value.code) == "403"
+    _assert_permission_row_untouched(mock_prisma_client, events)
+    mock_prisma_client.update_data.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_process_single_key_update_writes_the_object_permission_row_only_after_the_policy_allows():
+    mock_prisma_client = AsyncMock()
+    updated_row = MagicMock()
+    updated_row.model_dump.return_value = {"max_budget": 50.0, "team_id": "team-a"}
+    mock_prisma_client.update_data = AsyncMock(return_value={"data": updated_row})
+    events: list[str] = []
+    _record_object_permission_writes(mock_prisma_client, events)
+
+    await _process_single_key_update_under_policy(
+        mock_prisma_client, _update_with_object_permission(max_budget=50.0), _recording_policy(events, allowed=True)
+    )
+
+    _assert_permission_row_written_after_policy(events, mock_prisma_client.update_data.await_args.kwargs["data"])
+
+
+@pytest.mark.asyncio
+async def test_process_single_key_update_denied_by_the_policy_leaves_the_object_permission_row_untouched():
+    mock_prisma_client = AsyncMock()
+    mock_prisma_client.update_data = AsyncMock()
+    events: list[str] = []
+    _record_object_permission_writes(mock_prisma_client, events)
+
+    with pytest.raises(HTTPException) as exc_info:
+        await _process_single_key_update_under_policy(
+            mock_prisma_client, _update_with_object_permission(max_budget=5000.0), _recording_policy(events, allowed=False)
+        )
+
+    assert exc_info.value.status_code == 403
+    _assert_permission_row_untouched(mock_prisma_client, events)
+    mock_prisma_client.update_data.assert_not_awaited()
+
+
+@pytest.mark.asyncio
+async def test_regenerate_writes_the_object_permission_row_only_after_the_policy_allows():
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    events: list[str] = []
+    _record_object_permission_writes(mock_prisma_client, events)
+    data = RegenerateKeyRequest(max_budget=50.0, object_permission=LiteLLM_ObjectPermissionBase(vector_stores=["vs-1"]))
+
+    with _regenerate_policy_mocks(_recording_policy(events, allowed=True), AsyncMock(), AsyncMock()):
+        await _regenerate_under_policy(mock_prisma_client, _make_regenerate_existing_key(), data)
+
+    _assert_permission_row_written_after_policy(
+        events, mock_prisma_client.db.litellm_verificationtoken.update.await_args.kwargs["data"]
+    )
+
+
+@pytest.mark.asyncio
+async def test_regenerate_denied_by_the_policy_leaves_the_object_permission_row_untouched():
+    mock_prisma_client = _make_regenerate_mock_prisma()
+    events: list[str] = []
+    _record_object_permission_writes(mock_prisma_client, events)
+    data = RegenerateKeyRequest(max_budget=5000.0, object_permission=LiteLLM_ObjectPermissionBase(vector_stores=["vs-1"]))
+
+    with _regenerate_policy_mocks(_recording_policy(events, allowed=False), AsyncMock(), AsyncMock()):
+        with pytest.raises(HTTPException) as exc_info:
+            await _regenerate_under_policy(mock_prisma_client, _make_regenerate_existing_key(), data)
+
+    assert exc_info.value.status_code == 403
+    _assert_permission_row_untouched(mock_prisma_client, events)
+    assert mock_prisma_client.db.litellm_verificationtoken.update.await_count == 0
+
+
+@pytest.mark.asyncio
+async def test_bulk_update_keys_runs_custom_key_policy_per_key(monkeypatch):
+    from litellm.proxy.management_endpoints.key_management_endpoints import bulk_update_keys
+    from litellm.types.proxy.management_endpoints.key_management_endpoints import (
+        BulkUpdateKeyRequest,
+        BulkUpdateKeyRequestItem,
+    )
+
+    existing_keys = [
+        LiteLLM_VerificationToken(token="test-key-1", user_id="user-123", max_budget=None),
+        LiteLLM_VerificationToken(token="test-key-2", user_id="user-123", max_budget=50.0),
+    ]
+    updated_row = MagicMock()
+    updated_row.model_dump.return_value = {"user_id": "user-123", "max_budget": 100.0}
+    mock_prisma_client = AsyncMock()
+    mock_prisma_client.db.litellm_verificationtoken.find_unique = AsyncMock(side_effect=existing_keys)
+    mock_prisma_client.update_data = AsyncMock(return_value={"data": updated_row})
+    mock_prisma_client.get_data = AsyncMock(return_value=None)
+    monkeypatch.setattr("litellm.proxy.proxy_server.prisma_client", mock_prisma_client)
+    monkeypatch.setattr("litellm.proxy.proxy_server.user_api_key_cache", MagicMock())
+    monkeypatch.setattr("litellm.proxy.proxy_server.proxy_logging_obj", MagicMock())
+    monkeypatch.setattr("litellm.proxy.proxy_server.llm_router", None)
+    received: list[CustomKeyPolicyRequest] = []
+
+    async def cap_max_budget(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        received.append(policy_request)
+        max_budget = policy_request.effective_key.max_budget
+        if max_budget is not None and max_budget > 100:
+            return {"decision": False, "message": "max_budget must be 100 or less"}
+        return {"decision": True}
+
+    monkeypatch.setattr("litellm.proxy.proxy_server.user_custom_key_policy", cap_max_budget)
+
+    with (
+        patch(  # test-quality-ok: cache eviction is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints._delete_cache_key_object",
+            new_callable=AsyncMock,
+        ),
+        patch(  # test-quality-ok: update callback is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints.KeyManagementEventHooks.async_key_updated_hook",
+            new_callable=AsyncMock,
+        ),
+    ):
+        response = await bulk_update_keys(
+            data=BulkUpdateKeyRequest(
+                keys=[
+                    BulkUpdateKeyRequestItem(key="test-key-1", max_budget=100.0),
+                    BulkUpdateKeyRequestItem(key="test-key-2", max_budget=500.0),
+                ]
+            ),
+            user_api_key_dict=_make_regenerate_user_api_key_dict(),
+            litellm_changed_by=None,
+        )
+
+    assert [update.key for update in response.successful_updates] == ["test-key-1"]
+    assert [(failed.key, failed.failed_reason) for failed in response.failed_updates] == [
+        ("test-key-2", "max_budget must be 100 or less")
+    ]
+    assert mock_prisma_client.update_data.await_count == 1
+    assert [policy_request.operation for policy_request in received] == ["update", "update"]
+    assert [policy_request.effective_key.max_budget for policy_request in received] == [100.0, 500.0]
+    assert [
+        policy_request.existing_key.max_budget if policy_request.existing_key is not None else "missing"
+        for policy_request in received
+    ] == [None, 50.0]
+
+
+def _policy_generate_prisma() -> MagicMock:
+    mock_prisma = MagicMock()
+    mock_prisma.db.litellm_budgettable.create = AsyncMock(return_value=MagicMock(budget_id="budget-1"))
+    mock_prisma.jsonify_object = MagicMock(side_effect=lambda data: json.loads(data) if isinstance(data, str) else data)
+    return mock_prisma
+
+
+def _generate_policy_mocks(mock_prisma: MagicMock, generate_key_helper: AsyncMock, policy) -> ExitStack:
+    stack = ExitStack()
+    stack.enter_context(patch("litellm.proxy.proxy_server.prisma_client", mock_prisma))  # test-quality-ok: fake DB
+    stack.enter_context(patch("litellm.proxy.proxy_server.llm_router", None))  # test-quality-ok: no router in test
+    stack.enter_context(patch("litellm.proxy.proxy_server.premium_user", True))  # test-quality-ok: premium fields
+    stack.enter_context(patch("litellm.proxy.proxy_server.litellm_proxy_admin_name", "admin"))  # test-quality-ok: admin
+    stack.enter_context(patch("litellm.proxy.proxy_server.user_api_key_cache", MagicMock()))  # test-quality-ok: cache
+    stack.enter_context(
+        patch(  # test-quality-ok: the key write must not run on a denied generate
+            "litellm.proxy.management_endpoints.key_management_endpoints.generate_key_helper_fn",
+            generate_key_helper,
+        )
+    )
+    stack.enter_context(
+        patch("litellm.proxy.proxy_server.user_custom_key_policy", policy)  # test-quality-ok: inject policy hook
+    )
+    return stack
+
+
+def _generate_request(duration: str, organization_id: str | None) -> GenerateKeyRequest:
+    return GenerateKeyRequest(
+        duration=duration,
+        organization_id=organization_id,
+        guardrails=["g1"],
+        tags=["t1"],
+        soft_budget=10.0,
+        max_budget=20.0,
+    )
+
+
+def _assert_generate_policy_request(
+    policy_request: CustomKeyPolicyRequest, duration: str, organization_id: str | None
+) -> None:
+    assert policy_request.operation == "generate"
+    assert policy_request.existing_key is None
+    assert policy_request.effective_key.org_id == organization_id
+    assert policy_request.effective_key.max_budget == 20.0
+    assert policy_request.effective_key.metadata["guardrails"] == ["g1"]
+    assert policy_request.effective_key.metadata["tags"] == ["t1"]
+    _assert_expires_in(policy_request.effective_key, duration)
+
+
+@pytest.mark.asyncio
+async def test_generate_key_rejects_when_custom_key_policy_denies_before_any_write():
+    mock_prisma = _policy_generate_prisma()
+    generate_key_helper = AsyncMock(return_value=_POLICY_GENERATED_KEY)
+    received: list[CustomKeyPolicyRequest] = []
+    data = _generate_request("3000d", organization_id="org-1")
+
+    with _generate_policy_mocks(mock_prisma, generate_key_helper, _seven_day_policy(received)):
+        with pytest.raises(ProxyException) as exc_info:
+            await generate_key_fn(
+                data=data, user_api_key_dict=_make_regenerate_user_api_key_dict(), litellm_changed_by=None
+            )
+
+    assert str(exc_info.value.code) == "403"
+    assert exc_info.value.message == _POLICY_DENIAL_MESSAGE
+    mock_prisma.db.litellm_budgettable.create.assert_not_awaited()
+    generate_key_helper.assert_not_awaited()
+    assert len(received) == 1
+    _assert_generate_policy_request(received[0], "3000d", organization_id="org-1")
+    assert received[0].request is data
+    assert data.duration == "3000d"
+    assert data.guardrails == ["g1"]
+    assert data.tags == ["t1"]
+    assert data.organization_id == "org-1"
+
+
+@pytest.mark.asyncio
+async def test_generate_key_within_custom_key_policy_creates_the_key():
+    mock_prisma = _policy_generate_prisma()
+    generate_key_helper = AsyncMock(return_value=_POLICY_GENERATED_KEY)
+    received: list[CustomKeyPolicyRequest] = []
+    data = _generate_request("5d", organization_id=None)
+
+    with _generate_policy_mocks(mock_prisma, generate_key_helper, _seven_day_policy(received)):
+        await generate_key_fn(
+            data=data, user_api_key_dict=_make_regenerate_user_api_key_dict(), litellm_changed_by=None
+        )
+
+    mock_prisma.db.litellm_budgettable.create.assert_awaited_once()
+    generate_key_helper.assert_awaited_once()
+    assert len(received) == 1
+    _assert_generate_policy_request(received[0], "5d", organization_id=None)
+    assert received[0].request is data
+
+
+@pytest.mark.asyncio
+async def test_service_account_generate_rejects_when_custom_key_policy_denies():
+    from litellm.proxy.management_endpoints.key_management_endpoints import generate_service_account_key_fn
+
+    mock_prisma = _policy_generate_prisma()
+    mock_prisma.db.litellm_teamtable.find_unique = AsyncMock(return_value=MagicMock())
+    generate_key_helper = AsyncMock(return_value=_POLICY_GENERATED_KEY)
+    received: list[CustomKeyPolicyRequest] = []
+
+    with (
+        _generate_policy_mocks(mock_prisma, generate_key_helper, _seven_day_policy(received)),
+        patch(  # test-quality-ok: team lookup is outside the policy path
+            "litellm.proxy.management_endpoints.key_management_endpoints.get_team_object",
+            new_callable=AsyncMock,
+            return_value=None,
+        ),
+    ):
+        with pytest.raises(HTTPException) as exc_info:
+            await generate_service_account_key_fn(
+                data=GenerateKeyRequest(team_id="team-1", duration="3000d"),
+                user_api_key_dict=_make_regenerate_user_api_key_dict(),
+                litellm_changed_by=None,
+            )
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail == _POLICY_DENIAL_MESSAGE
+    generate_key_helper.assert_not_awaited()
+    mock_prisma.db.litellm_budgettable.create.assert_not_awaited()
+    assert [policy_request.operation for policy_request in received] == ["generate"]
+    assert received[0].existing_key is None
+    assert received[0].effective_key.team_id == "team-1"
+    assert received[0].effective_key.user_id is None
+    _assert_expires_in(received[0].effective_key, "3000d")
+
+
+@pytest.mark.asyncio
+async def test_effective_key_after_update_decodes_json_string_columns_and_keeps_omitted_fields():
+    existing_key = LiteLLM_VerificationToken(token="tok", user_id="u1", team_id="team-a")
+    non_default_values = await prepare_key_update_data(
+        data=UpdateKeyRequest(
+            key="tok", router_settings={"num_retries": 3}, budget_limits=[{"budget_duration": "1d", "max_budget": 2.0}]
+        ),
+        existing_key_row=existing_key,
+    )
+    assert isinstance(non_default_values["router_settings"], str)
+    assert isinstance(non_default_values["budget_limits"], str)
+
+    effective_key = _effective_key_after_update(existing_key_row=existing_key, non_default_values=non_default_values)
+
+    assert effective_key.router_settings == {"num_retries": 3}
+    assert effective_key.budget_limits is not None
+    assert effective_key.budget_limits[0]["max_budget"] == 2.0
+    assert effective_key.budget_limits[0]["budget_duration"] == "1d"
+    assert effective_key.budget_limits[0]["reset_at"] is not None
+    assert effective_key.team_id == "team-a"
+    assert effective_key.user_id == "u1"
+
+
+@pytest.mark.asyncio
+async def test_effective_key_after_update_clears_expiry_for_a_minus_one_duration():
+    existing_key = LiteLLM_VerificationToken(token="tok", expires=datetime(2027, 1, 1, tzinfo=timezone.utc))
+    non_default_values = await prepare_key_update_data(
+        data=UpdateKeyRequest(key="tok", duration="-1"), existing_key_row=existing_key
+    )
+
+    effective_key = _effective_key_after_update(existing_key_row=existing_key, non_default_values=non_default_values)
+
+    assert effective_key.expires is None
+
+
+def test_effective_key_after_update_swaps_the_object_permission_id_and_drops_the_stale_relation():
+    existing_key = LiteLLM_VerificationToken(
+        token="tok",
+        object_permission_id="op-old",
+        object_permission=LiteLLM_ObjectPermissionTable(object_permission_id="op-old", mcp_servers=["old"]),
+    )
+
+    effective_key = _effective_key_after_update(
+        existing_key_row=existing_key, non_default_values={"object_permission_id": "op-new"}
+    )
+
+    assert effective_key.object_permission_id == "op-new"
+    assert effective_key.object_permission is None
+    assert existing_key.object_permission is not None
+    assert existing_key.object_permission.mcp_servers == ["old"]
+
+
+def test_effective_key_for_generate_reflects_the_processed_request_without_mutating_it():
+    now = datetime(2026, 1, 1, tzinfo=timezone.utc)
+    data = GenerateKeyRequest(
+        duration="5d",
+        organization_id="org-1",
+        metadata={"a": 1},
+        guardrails=["g1"],
+        tags=["t1"],
+        budget_duration="1d",
+        max_budget=3.0,
+        budget_limits=[{"budget_duration": "1d", "max_budget": 5.0}],
+        auto_rotate=True,
+        rotation_interval="30d",
+        object_permission={"mcp_servers": ["srv"]},
+        key_type=LiteLLMKeyType.LLM_API,
+    )
+
+    effective_key = _effective_key_for_generate(data=data, now=now)
+
+    assert effective_key.expires == now + timedelta(days=5)
+    assert effective_key.key_rotation_at == now + timedelta(days=30)
+    assert effective_key.budget_limits is not None
+    assert effective_key.budget_limits[0]["max_budget"] == 5.0
+    assert effective_key.budget_limits[0]["reset_at"] is not None
+    assert effective_key.object_permission is None
+    assert effective_key.org_id == "org-1"
+    assert effective_key.metadata == {"a": 1, "guardrails": ["g1"], "tags": ["t1"]}
+    assert effective_key.max_budget == 3.0
+    assert effective_key.budget_duration == "1d"
+    assert effective_key.budget_reset_at is not None
+    assert effective_key.key_type == "llm_api"
+    assert effective_key.allowed_routes == ["llm_api_routes"]
+    assert data.metadata == {"a": 1}
+    assert data.guardrails == ["g1"]
+    assert data.tags == ["t1"]
+    assert data.duration == "5d"
+    assert data.budget_limits is not None
+    assert data.budget_limits[0].reset_at is None
+    assert data.object_permission is not None
+    assert data.object_permission.mcp_servers == ["srv"]
+
+
+def test_effective_key_for_generate_stores_no_budget_windows_for_an_empty_list():
+    effective_key = _effective_key_for_generate(
+        data=GenerateKeyRequest(budget_limits=[]), now=datetime(2026, 1, 1, tzinfo=timezone.utc)
+    )
+
+    assert effective_key.budget_limits is None
+
+
+def test_effective_key_for_generate_without_duration_never_expires():
+    effective_key = _effective_key_for_generate(
+        data=GenerateKeyRequest(), now=datetime(2026, 1, 1, tzinfo=timezone.utc)
+    )
+
+    assert effective_key.expires is None
+    assert effective_key.budget_reset_at is None
+    assert effective_key.key_rotation_at is None
+    assert effective_key.key_type == "default"
+
+
+def _policy_request_for_generate() -> CustomKeyPolicyRequest:
+    return CustomKeyPolicyRequest(
+        operation="generate",
+        existing_key=None,
+        effective_key=LiteLLM_VerificationToken(token="tok"),
+        request=GenerateKeyRequest(),
+    )
+
+
+@pytest.mark.asyncio
+async def test_enforce_custom_key_policy_rejects_a_sync_hook():
+    def sync_hook(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        return {"decision": True}
+
+    with pytest.raises(ValueError, match="user_custom_key_policy must be a coroutine"):
+        await _enforce_custom_key_policy(hook=sync_hook, build_policy_request=_policy_request_for_generate)
+
+
+@pytest.mark.asyncio
+async def test_enforce_custom_key_policy_uses_the_default_denial_message():
+    async def deny(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        return {"decision": False}
+
+    with pytest.raises(HTTPException) as exc_info:
+        await _enforce_custom_key_policy(hook=deny, build_policy_request=_policy_request_for_generate)
+
+    assert exc_info.value.status_code == 403
+    assert exc_info.value.detail == "Authentication Failed - Custom Auth Rule"
+
+
+@pytest.mark.asyncio
+async def test_enforce_custom_key_policy_allows_when_the_decision_is_missing():
+    received: list[CustomKeyPolicyRequest] = []
+
+    async def no_decision(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        received.append(policy_request)
+        return {}
+
+    await _enforce_custom_key_policy(hook=no_decision, build_policy_request=_policy_request_for_generate)
+
+    assert len(received) == 1
+    assert received[0].operation == "generate"
+
+
+@pytest.mark.asyncio
+async def test_enforce_custom_key_policy_never_builds_the_request_without_a_hook():
+    await _enforce_custom_key_policy(
+        hook=None, build_policy_request=lambda: pytest.fail("policy request built without a hook")
+    )
+
+
 @pytest.mark.asyncio
 async def test_regenerate_evicts_jwt_key_mapping_cache_so_next_jwt_call_gets_new_token():
     """
@@ -13825,10 +14843,6 @@ async def test_regenerate_applies_normalized_mcp_object_permission():
             "litellm.proxy.management_endpoints.key_management_endpoints.validate_key_vector_stores_against_team",
             new_callable=AsyncMock,
         ),
-        patch(
-            "litellm.proxy.management_endpoints.key_management_endpoints._persist_deleted_verification_tokens",
-            new_callable=AsyncMock,
-        ),
         patch(
             "litellm.proxy.management_endpoints.key_management_endpoints._execute_virtual_key_regeneration",
             execute_mock,
@@ -18624,3 +19638,38 @@ async def test_flush_gcs_names_a_missing_logger_when_the_callback_never_initiali
         await flush_gcs_and_describe_failures(None, "health-event")
         == "gcs_bucket callback was selected but no GCS logger was initialized"
     )
+
+
+@pytest.mark.asyncio
+async def test_bulk_update_team_keys_runs_custom_key_policy_per_key(monkeypatch):
+    from litellm.types.proxy.management_endpoints.key_management_endpoints import (
+        BulkUpdateTeamKeysRequest,
+        KeyUpdateFields,
+    )
+
+    keys = [_make_team_key("tok-a"), _make_team_key("tok-b")]
+    mock = _setup_team_keys_mocks(
+        monkeypatch, find_many=keys, update_data=AsyncMock(return_value={"data": _updated({"max_budget": 50.0})})
+    )
+    received: list[CustomKeyPolicyRequest] = []
+
+    async def freeze_tok_b(policy_request: CustomKeyPolicyRequest) -> dict[str, object]:
+        received.append(policy_request)
+        if policy_request.existing_key is not None and policy_request.existing_key.token == "tok-b":
+            return {"decision": False, "message": "tok-b is frozen"}
+        return {"decision": True}
+
+    monkeypatch.setattr("litellm.proxy.proxy_server.user_custom_key_policy", freeze_tok_b)
+
+    response = await _call_as_admin(
+        BulkUpdateTeamKeysRequest(
+            team_id="team-abc", key_ids=["tok-a", "tok-b"], update_fields=KeyUpdateFields(max_budget=50.0)
+        )
+    )
+
+    assert [update.key for update in response.successful_updates] == ["tok-a"]
+    assert [(failed.key, failed.failed_reason) for failed in response.failed_updates] == [("tok-b", "tok-b is frozen")]
+    mock.update_data.assert_awaited_once()
+    assert [policy_request.operation for policy_request in received] == ["update", "update"]
+    assert [policy_request.effective_key.max_budget for policy_request in received] == [50.0, 50.0]
+    assert [policy_request.effective_key.team_id for policy_request in received] == ["team-abc", "team-abc"]
diff --git a/tests/test_litellm/proxy/pass_through_endpoints/test_pass_through_endpoints.py b/tests/test_litellm/proxy/pass_through_endpoints/test_pass_through_endpoints.py
index d57bed430c1..11066d4ed38 100644
--- a/tests/test_litellm/proxy/pass_through_endpoints/test_pass_through_endpoints.py
+++ b/tests/test_litellm/proxy/pass_through_endpoints/test_pass_through_endpoints.py
@@ -5030,6 +5030,100 @@ async def test_websocket_passthrough_rewrites_gateway_alias_setup_model():
     assert sent_setup["model"] == "projects/proj-db/locations/global/publishers/google/models/gemini-live-2.5-flash"
 
 
+@pytest.mark.parametrize(
+    "setup_model",
+    ["gemini-live-2.5-flash", "models/gemini-live-2.5-flash", "publishers/google/models/gemini-live-2.5-flash"],
+)
+def test_vertex_live_setup_model_resolves_before_extraction(setup_model):
+    """A bare gateway alias left the session logged as ``unknown`` at zero cost.
+
+    The model was read off the raw client frame, and the extractor only yields a name when the string
+    already contains ``/models/``. The rewriter qualifies it a few lines later for the upstream, so a
+    client that addressed the gateway the documented way, by alias, logged no model and therefore
+    resolved no cost-map entry. Resolving first is what puts the real name on the logging object.
+    """
+    from litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints import (
+        _build_vertex_live_setup_model_rewriter,
+    )
+    from litellm.proxy.pass_through_endpoints.pass_through_endpoints import (
+        _extract_model_from_vertex_ai_setup,
+        _resolved_vertex_live_setup,
+    )
+
+    rewriter = _build_vertex_live_setup_model_rewriter(
+        vertex_project="proj-db", vertex_location="global", llm_router=None
+    )
+    setup_data = {"model": setup_model}
+
+    resolved = _extract_model_from_vertex_ai_setup(_resolved_vertex_live_setup(setup_data, rewriter))
+
+    assert resolved == "gemini-live-2.5-flash", "an unresolved setup model logs the session as 'unknown'"
+
+
+@pytest.mark.asyncio
+async def test_websocket_passthrough_logs_a_bare_alias_setup_model():
+    """End to end through the relay: a bare alias must reach the logging object as a real model name.
+
+    This is the call-site half of the fix. The helper tests above pass even if extraction moves back
+    before the rewrite, so this one drives the real websocket relay and asserts on what got logged,
+    which is the name the cost map is looked up by. An unbilled session logs ``unknown``.
+    """
+    from litellm.proxy.pass_through_endpoints.llm_passthrough_endpoints import (
+        _build_vertex_live_setup_model_rewriter,
+    )
+
+    upstream_ws = RecordingUpstreamWebSocket()
+    setup_frame = json.dumps({"setup": {"model": "gemini-live-2.5-flash"}})
+    websocket = _client_websocket(
+        AsyncMock(
+            side_effect=[
+                {"type": "websocket.receive", "text": setup_frame},
+                {"type": "websocket.disconnect"},
+            ]
+        )
+    )
+    built = []
+    real_logging = litellm.litellm_core_utils.litellm_logging.Logging
+
+    def _capture(*args, **kwargs):
+        obj = real_logging(*args, **kwargs)
+        built.append(obj)
+        return obj
+
+    with _patched_websocket_passthrough_environment(upstream_ws):
+        with patch("litellm.litellm_core_utils.litellm_logging.Logging", side_effect=_capture):
+            await websocket_passthrough_request(
+                websocket=websocket,
+                target="wss://aiplatform.googleapis.com/ws/google.cloud.aiplatform.v1.LlmBidiService/BidiGenerateContent",
+                custom_headers={"Authorization": "Bearer token"},
+                user_api_key_dict=UserAPIKeyAuth(),
+                forward_headers=False,
+                endpoint="/vertex_ai/live",
+                accept_websocket=False,
+                setup_model_rewriter=_build_vertex_live_setup_model_rewriter(
+                    vertex_project="proj-db", vertex_location="global", llm_router=None
+                ),
+            )
+
+    assert built, "the relay should have built a logging object"
+    assert built[0].model == "gemini-live-2.5-flash", "a bare alias must not log as 'unknown'"
+
+
+def test_vertex_live_setup_resolution_is_inert_without_a_rewriter():
+    """Non-Live passthrough routes pass no rewriter, so the frame must be handed over untouched."""
+    from litellm.proxy.pass_through_endpoints.pass_through_endpoints import (
+        _extract_model_from_vertex_ai_setup,
+        _resolved_vertex_live_setup,
+    )
+
+    setup_data = {"model": "projects/p/locations/global/publishers/google/models/gemini-live-2.5-flash"}
+
+    assert _resolved_vertex_live_setup(setup_data, None) is setup_data
+    assert _extract_model_from_vertex_ai_setup(_resolved_vertex_live_setup(setup_data, None)) == (
+        "gemini-live-2.5-flash"
+    )
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize("rcvd_close", [None, "abnormal", "no_status"])
 async def test_websocket_passthrough_does_not_relay_unsendable_upstream_close(rcvd_close):
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 e6fda90db34..e8e7a36bd05 100644
--- a/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
+++ b/tests/test_litellm/proxy/test_litellm_pre_call_utils.py
@@ -7433,13 +7433,14 @@ def _reserved_stamp_key(key_metadata: dict | None = None) -> UserAPIKeyAuth:
 _PLANTED_STAMPS = {
     "attempted_fallbacks": 99,
     "original_model_group": "spoofed-group",
+    "request_retry_count": -100,
     "_client_output_ceiling": {"api_base": "https://attacker.example"},
     "client_key": "client_value",
 }
 
 
 @pytest.mark.asyncio
-async def test_add_litellm_data_to_request_strips_router_reserved_stamps_from_both_buckets():
+async def test_add_litellm_data_to_request_strips_router_reserved_stamps_from_both_buckets() -> None:
     """attempted_fallbacks and original_model_group are router-written facts the spend row
     reads back; a client planting them in either bucket is dropped at the boundary so the
     router never sees a reserved key it did not write."""
@@ -7465,11 +7466,12 @@ async def test_add_litellm_data_to_request_strips_router_reserved_stamps_from_bo
     assert "attempted_fallbacks" not in updated["metadata"]
     assert "original_model_group" not in updated["metadata"]
     assert "_client_output_ceiling" not in updated["metadata"]
+    assert "request_retry_count" not in updated["metadata"]
     assert updated["metadata"]["client_key"] == "client_value"
 
 
 @pytest.mark.asyncio
-async def test_add_litellm_data_to_request_strips_router_reserved_stamps_from_json_string_litellm_metadata():
+async def test_add_litellm_data_to_request_strips_router_reserved_stamps_from_json_string_litellm_metadata() -> None:
     from litellm.proxy.litellm_pre_call_utils import add_litellm_data_to_request
 
     data = {
@@ -7490,11 +7492,12 @@ async def test_add_litellm_data_to_request_strips_router_reserved_stamps_from_js
     assert "litellm_metadata" not in updated
     assert "attempted_fallbacks" not in updated["metadata"]
     assert "original_model_group" not in updated["metadata"]
+    assert "request_retry_count" not in updated["metadata"]
     assert updated["metadata"]["client_key"] == "client_value"
 
 
 @pytest.mark.asyncio
-async def test_add_litellm_data_to_request_strips_router_reserved_stamps_despite_pricing_override_opt_in():
+async def test_add_litellm_data_to_request_strips_router_reserved_stamps_despite_pricing_override_opt_in() -> None:
     """The pricing strip is gated on allow_client_pricing_override; the reserved-stamp strip
     is not, because no key or team setting makes a client-written fallback count valid."""
     from litellm.proxy.litellm_pre_call_utils import add_litellm_data_to_request
@@ -7518,6 +7521,7 @@ async def test_add_litellm_data_to_request_strips_router_reserved_stamps_despite
     assert updated["metadata"]["model_info"] == {"input_cost_per_token": 0.0}
     assert "attempted_fallbacks" not in updated["metadata"]
     assert "original_model_group" not in updated["metadata"]
+    assert "request_retry_count" not in updated["metadata"]
 
 
 @pytest.mark.asyncio
diff --git a/tests/test_litellm/proxy/types_utils/test_db_overlay_remote_module_scrub.py b/tests/test_litellm/proxy/types_utils/test_db_overlay_remote_module_scrub.py
index 100ba653f3a..0072997a0d9 100644
--- a/tests/test_litellm/proxy/types_utils/test_db_overlay_remote_module_scrub.py
+++ b/tests/test_litellm/proxy/types_utils/test_db_overlay_remote_module_scrub.py
@@ -43,6 +43,7 @@ def test_litellm_settings_callback_list_strips_remote_urls(field):
         "custom_auth",
         "custom_key_generate",
         "custom_key_update",
+        "custom_key_policy",
         "custom_sso",
         "custom_ui_sso_sign_in_handler",
     ],
diff --git a/tests/test_litellm/realtime_api/test_main.py b/tests/test_litellm/realtime_api/test_main.py
index d3d41c5b54b..643e65af47c 100644
--- a/tests/test_litellm/realtime_api/test_main.py
+++ b/tests/test_litellm/realtime_api/test_main.py
@@ -7,6 +7,7 @@ from unittest.mock import MagicMock, patch
 import pytest
 
 import litellm
+from litellm.models.credentials import CredentialItem
 from litellm.realtime_api import main as realtime_main
 from litellm.realtime_api.main import _with_resolved_session_model
 
@@ -224,9 +225,11 @@ def test_client_secret_forwards_nested_transcription_model_untouched(monkeypatch
 class _CapturingConnect:
     def __init__(self) -> None:
         self.url: str | None = None
+        self.kwargs: dict[str, object] = {}
 
     def __call__(self, url: str, **kwargs: object) -> "_CapturingConnect":
         self.url = url
+        self.kwargs = kwargs
         return self
 
     async def __aenter__(self) -> MagicMock:
@@ -241,6 +244,72 @@ class _CapturingConnect:
         return None
 
 
+@pytest.mark.asyncio
+async def test_azure_health_check_resolves_stored_credentials(monkeypatch):
+    monkeypatch.setattr(
+        litellm,
+        "credential_list",
+        [
+            CredentialItem(
+                credential_name="azure-rt",
+                credential_values={
+                    "api_key": "sk-from-credential",
+                    "api_base": "https://example.openai.azure.com",
+                    "api_version": "2025-04-01-preview",
+                },
+                credential_info={},
+            )
+        ],
+    )
+    connect = _CapturingConnect()
+    with patch("websockets.connect", connect):
+        assert await realtime_main._realtime_health_check(
+            model="gpt-realtime",
+            custom_llm_provider="azure",
+            api_key=None,
+            realtime_protocol="beta",
+            model_params={"model": "azure/gpt-realtime", "litellm_credential_name": "azure-rt"},
+        )
+    assert connect.kwargs["additional_headers"] == {"api-key": "sk-from-credential"}
+    assert connect.url is not None
+    assert connect.url.startswith("wss://example.openai.azure.com")
+    assert "api-version=2025-04-01-preview" in connect.url
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    ("custom_llm_provider", "model", "expected_url"),
+    [
+        ("xai", "grok-voice-latest", "wss://api.x.ai/v1/realtime?model=grok-voice-latest"),
+        ("openai", "gpt-realtime", "wss://api.openai.com/v1/realtime?model=gpt-realtime"),
+    ],
+)
+async def test_bearer_health_check_sends_stored_credential_as_bearer_token(
+    monkeypatch, custom_llm_provider: str, model: str, expected_url: str
+):
+    monkeypatch.setattr(
+        litellm,
+        "credential_list",
+        [
+            CredentialItem(
+                credential_name="voice-key",
+                credential_values={"api_key": "sk-from-credential"},
+                credential_info={},
+            )
+        ],
+    )
+    connect = _CapturingConnect()
+    with patch("websockets.connect", connect):
+        assert await realtime_main._realtime_health_check(
+            model=model,
+            custom_llm_provider=custom_llm_provider,
+            api_key=None,
+            model_params={"model": f"{custom_llm_provider}/{model}", "litellm_credential_name": "voice-key"},
+        )
+    assert connect.kwargs["additional_headers"] == {"Authorization": "Bearer sk-from-credential"}
+    assert connect.url == expected_url
+
+
 @pytest.mark.asyncio
 async def test_azure_health_check_probes_ga_transcription_url_for_transcription_model(local_model_cost_map):
     """Regression for LIT-6240: transcription-only models (mode audio_transcription
diff --git a/tests/test_litellm/rust_bridge/test_lifecycle.py b/tests/test_litellm/rust_bridge/test_lifecycle.py
index 1f0b5591c2b..d73385621d5 100644
--- a/tests/test_litellm/rust_bridge/test_lifecycle.py
+++ b/tests/test_litellm/rust_bridge/test_lifecycle.py
@@ -8,7 +8,7 @@ from litellm.rust_bridge.lifecycle import check_limits
 
 @pytest.mark.parametrize("metadata_key", ["metadata", "litellm_metadata"])
 @pytest.mark.parametrize(
-    "cap, attempted_retries, refused",
+    "cap, request_retry_count, refused",
     [(5, 5, True), (5, 4, False), (0, 0, False), (0, 1, True)],
     ids=[
         "cap-above-four-reached",
@@ -17,12 +17,15 @@ from litellm.rust_bridge.lifecycle import check_limits
         "cap-of-zero-refuses-first-retry",
     ],
 )
-def test_check_limits_reads_attempted_retries(
-    monkeypatch: pytest.MonkeyPatch, metadata_key: str, cap: int, attempted_retries: int, refused: bool
+def test_check_limits_reads_request_retry_count(
+    monkeypatch: pytest.MonkeyPatch, metadata_key: str, cap: int, request_retry_count: int, refused: bool
 ) -> None:
     monkeypatch.setattr(litellm, "num_retries_per_request", cap)
     monkeypatch.setattr(litellm, "max_budget", None)
-    kwargs: Final = {"model": "mistral/mistral-ocr-latest", metadata_key: {"attempted_retries": attempted_retries}}
+    kwargs: Final = {
+        "model": "mistral/mistral-ocr-latest",
+        metadata_key: {"request_retry_count": request_retry_count},
+    }
     if refused:
         with pytest.raises(RuntimeError, match="Max retries per request hit!"):
             check_limits(kwargs)
diff --git a/tests/test_litellm/test_router.py b/tests/test_litellm/test_router.py
index 3cabcd71627..0485da3eba9 100644
--- a/tests/test_litellm/test_router.py
+++ b/tests/test_litellm/test_router.py
@@ -11066,6 +11066,66 @@ async def test_num_retries_per_request_stops_retries_at_caps_above_four(monkeypa
     ]
 
 
+def _failing_group_with_healthy_fallback_router(num_retries: int) -> litellm.Router:
+    return litellm.Router(
+        model_list=[
+            {
+                "model_name": "broken-group",
+                "litellm_params": {
+                    "model": "openai/gpt-4o-mini",
+                    "api_key": "sk-fake",
+                    "mock_response": "litellm.InternalServerError",
+                },
+            },
+            {
+                "model_name": "healthy-group",
+                "litellm_params": {"model": "openai/gpt-4o-mini", "api_key": "sk-fake", "mock_response": "ok"},
+            },
+        ],
+        fallbacks=[{"broken-group": ["healthy-group"]}],
+        num_retries=num_retries,
+    )
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize(
+    "cap, planted_count, hop_refused",
+    [(2, None, True), (4, None, False), (2, -100, True)],
+    ids=["cap-spent-before-the-hop", "cap-not-reached-by-the-hop", "planted-negative-count-does-not-lift-the-cap"],
+)
+async def test_num_retries_per_request_counts_retries_across_fallback_hops(
+    monkeypatch: pytest.MonkeyPatch, cap: int, planted_count: int | None, hop_refused: bool
+) -> None:
+    """num_retries_per_request caps the retries of one request, fallback hops included. Each hop starts a
+    fresh per-hop attempted_retries at zero, so a cap read from that counter let every hop retry from zero
+    and a request could spend far more retries than the cap allows. A caller who plants a negative count
+    in the request metadata must not push the cap further away either."""
+    monkeypatch.setattr(litellm, "num_retries_per_request", cap)
+    router = _failing_group_with_healthy_fallback_router(num_retries=1)
+    recorder = _FallbackAttemptRecorder()
+    litellm.callbacks.append(recorder)
+    try:
+        metadata = {} if planted_count is None else {"request_retry_count": planted_count}
+        request = router.acompletion(
+            model="broken-group", messages=[{"role": "user", "content": "hi"}], metadata=metadata
+        )
+        if not hop_refused:
+            assert (await request).choices[0].message.content == "ok"
+            return
+        with pytest.raises(litellm.InternalServerError):
+            await request
+    finally:
+        litellm.callbacks.remove(recorder)
+
+    assert recorder.failed_targets == ["healthy-group"]
+    hop_refusals = [
+        record["attempted_retries"]
+        for record in recorder.breadcrumbs_per_target[0]
+        if record["model_group"] == "healthy-group" and "Max retries per request hit!" in record["exception_string"]
+    ]
+    assert hop_refusals == [0, 1]
+
+
 @pytest.mark.asyncio
 async def test_fallback_traceback_stays_available_at_debug_level():
     """Dropping the stack from the ERROR line is only safe because the fallback path still
diff --git a/tests/test_litellm/test_utils.py b/tests/test_litellm/test_utils.py
index ae0e08ebfb1..8bf8489fc52 100644
--- a/tests/test_litellm/test_utils.py
+++ b/tests/test_litellm/test_utils.py
@@ -4077,10 +4077,11 @@ class TestMetadataNoneHandling:
 
 
 _RETRY_CAP_CASES: Final = (
-    pytest.param(5, {"attempted_retries": 5}, True, id="cap-above-four-reached"),
-    pytest.param(5, {"attempted_retries": 4}, False, id="cap-above-four-not-reached"),
-    pytest.param(0, {"attempted_retries": 0}, False, id="first-attempt-passes-cap-of-zero"),
-    pytest.param(0, {"attempted_retries": 1}, True, id="cap-of-zero-refuses-first-retry"),
+    pytest.param(5, {"request_retry_count": 5}, True, id="cap-above-four-reached"),
+    pytest.param(5, {"request_retry_count": 4}, False, id="cap-above-four-not-reached"),
+    pytest.param(0, {"request_retry_count": 0}, False, id="first-attempt-passes-cap-of-zero"),
+    pytest.param(0, {"request_retry_count": 1}, True, id="cap-of-zero-refuses-first-retry"),
+    pytest.param(0, {"attempted_retries": 1}, False, id="per-hop-attempted-retries-is-not-the-cap"),
     pytest.param(5, {"previous_models": ("a", "b", "c", "d", "e")}, False, id="breadcrumb-count-is-not-the-cap"),
     pytest.param(5, None, False, id="metadata-none"),
 )
@@ -4098,7 +4099,9 @@ def _capped_completion_kwargs(metadata_key: str, metadata: object) -> dict[str,
 
 @pytest.mark.parametrize("metadata_key", ["metadata", "litellm_metadata"])
 @pytest.mark.parametrize("cap, metadata, refused", _RETRY_CAP_CASES)
-def test_num_retries_per_request_reads_attempted_retries_sync(monkeypatch, metadata_key, cap, metadata, refused):
+def test_num_retries_per_request_reads_request_retry_count_sync(
+    monkeypatch: pytest.MonkeyPatch, metadata_key: str, cap: int, metadata: object, refused: bool
+) -> None:
     monkeypatch.setattr(litellm, "num_retries_per_request", cap)
     kwargs: Final = _capped_completion_kwargs(metadata_key, metadata)
     if refused:
@@ -4111,7 +4114,9 @@ def test_num_retries_per_request_reads_attempted_retries_sync(monkeypatch, metad
 @pytest.mark.asyncio
 @pytest.mark.parametrize("metadata_key", ["metadata", "litellm_metadata"])
 @pytest.mark.parametrize("cap, metadata, refused", _RETRY_CAP_CASES)
-async def test_num_retries_per_request_reads_attempted_retries_async(monkeypatch, metadata_key, cap, metadata, refused):
+async def test_num_retries_per_request_reads_request_retry_count_async(
+    monkeypatch: pytest.MonkeyPatch, metadata_key: str, cap: int, metadata: object, refused: bool
+) -> None:
     monkeypatch.setattr(litellm, "num_retries_per_request", cap)
     kwargs: Final = _capped_completion_kwargs(metadata_key, metadata)
     if refused:
diff --git a/tests/test_litellm_rust/ocr/test_lifecycle.py b/tests/test_litellm_rust/ocr/test_lifecycle.py
index 77d9ef167d0..dfcd63d3019 100644
--- a/tests/test_litellm_rust/ocr/test_lifecycle.py
+++ b/tests/test_litellm_rust/ocr/test_lifecycle.py
@@ -806,7 +806,7 @@ async def test_shared_call_limits_still_reject_before_reading_ocr_file(
     monkeypatch.setattr(litellm, "_current_cost", 2)
     monkeypatch.setattr(litellm, "num_retries_per_request", 1 if limit == "retries" else None)
     expected: Final = litellm.BudgetExceededError if limit == "budget" else RuntimeError
-    arguments: Final = {"document": {"type": "file", "file": File()}, "metadata": {"attempted_retries": 1}}
+    arguments: Final = {"document": {"type": "file", "file": File()}, "metadata": {"request_retry_count": 1}}
     with pytest.raises(expected, match=r"Budget has been exceeded|Max retries per request hit"):
         await call_aocr(ocr_server, **arguments) if asynchronous else call_ocr(ocr_server, **arguments)
     assert reads == []