diff --git a/litellm/main.py b/litellm/main.py
index 78b6f8e4153..873aef483bf 100644
--- a/litellm/main.py
+++ b/litellm/main.py
@@ -6517,6 +6517,7 @@ _CHAT_SURFACE_KWARGS: Final = (
     "mock_delay",
     "mock_timeout",
 )
+_SKIP_RESPONSES_API_BRIDGE: Final = "_skip_responses_api_bridge"
 _TEXT_COMPLETION_PROVIDERS: Final = frozenset(
     ("text-completion-openai", "text-completion-codestral", "text-completion-inception")
 )
@@ -6530,6 +6531,7 @@ class PlannedChat:
     kwargs: Mapping[str, object]
     non_default_params: Mapping[str, object]
     control_options: ControlOptions
+    skip_responses_api_bridge: bool
 
 
 def _optional_str(value: object) -> str | None:
@@ -6599,7 +6601,11 @@ def plan_chat(request: Mapping[str, object], logging_obj: LiteLLMLoggingObj) ->
     )
     if resolved_provider in _TEXT_COMPLETION_PROVIDERS:
         return None
-    kwargs: Final = {key: value for key, value in request.items() if key not in _EXECUTE_CHAT_PARAMS}
+    kwargs: Final = {
+        key: value
+        for key, value in request.items()
+        if key not in _EXECUTE_CHAT_PARAMS and key != _SKIP_RESPONSES_API_BRIDGE
+    }
     tools: Final = validate_and_fix_openai_tools(tools=_object_list(request.get("tools")))
     messages: Final = get_completion_messages(
         messages=validate_and_fix_openai_messages(messages=_object_list(request.get("messages")) or []),
@@ -6639,6 +6645,7 @@ def plan_chat(request: Mapping[str, object], logging_obj: LiteLLMLoggingObj) ->
         kwargs=MappingProxyType(kwargs),
         non_default_params=MappingProxyType(non_default_params),
         control_options=_resolve_control_options(kwargs, model),
+        skip_responses_api_bridge=request.get(_SKIP_RESPONSES_API_BRIDGE) is True,
     )
 
 
@@ -6648,7 +6655,7 @@ def _run_planned_chat(plan: PlannedChat, is_async: bool) -> ModelResponse | Cust
         kwargs={**plan.kwargs, "acompletion": is_async},
         non_default_params=dict(plan.non_default_params),
         control_options=plan.control_options,
-        skip_responses_api_bridge=False,
+        skip_responses_api_bridge=plan.skip_responses_api_bridge,
         prompt_id=None,
         prompt_variables=None,
     )
diff --git a/litellm/responses/litellm_completion_transformation/handler.py b/litellm/responses/litellm_completion_transformation/handler.py
index 5489d2223ac..0b148985b9a 100644
--- a/litellm/responses/litellm_completion_transformation/handler.py
+++ b/litellm/responses/litellm_completion_transformation/handler.py
@@ -3,7 +3,7 @@ Handler for transforming responses api requests to litellm.completion requests
 """
 
 from collections.abc import Coroutine, Mapping
-from typing import Final
+from typing import TYPE_CHECKING, Final
 
 from pydantic import TypeAdapter
 
@@ -23,9 +23,35 @@ from litellm.types.llms.openai import (
 )
 from litellm.types.utils import ModelResponse
 
+if TYPE_CHECKING:
+    from litellm.main import PlannedChat
+
 _REQUEST_KWARGS_ADAPTER: Final = TypeAdapter(dict[str, object])
 
 
+def _plan_bridged_chat(request: Mapping[str, object]) -> "PlannedChat | None":
+    from litellm.litellm_core_utils.litellm_logging import Logging
+    from litellm.main import plan_chat
+
+    logging_obj: Final = request.get("litellm_logging_obj")
+    return plan_chat(request, logging_obj) if isinstance(logging_obj, Logging) else None
+
+
+def _price_planned_chat_response(
+    request: Mapping[str, object], response: ModelResponse | litellm.CustomStreamWrapper
+) -> None:
+    """Prices the chat response as `acompletion` would have, before it becomes a Responses object."""
+    from litellm.litellm_core_utils.litellm_logging import Logging
+
+    logging_obj: Final = request.get("litellm_logging_obj")
+    if not isinstance(logging_obj, Logging):
+        return
+    if isinstance(response, ModelResponse):
+        logging_obj.price_bridged_provider_response(response)
+    else:
+        logging_obj.price_bridged_provider_stream(response)
+
+
 class LiteLLMCompletionTransformationHandler:
     def response_api_handler(
         self,
@@ -71,15 +97,18 @@ class LiteLLMCompletionTransformationHandler:
                 **kwargs,
             )
 
-        completion_args: Final = {}
-        completion_args.update(kwargs)
-        completion_args.update(litellm_completion_request)
-        completion_args["_skip_responses_api_bridge"] = True
+        completion_args: Final = {**kwargs, **litellm_completion_request, "_skip_responses_api_bridge": True}
 
-        litellm_completion_response: Final[ModelResponse | litellm.CustomStreamWrapper] = litellm.completion(
-            **completion_args,
+        from litellm.main import execute_planned_chat
+
+        planned_chat: Final = _plan_bridged_chat(_REQUEST_KWARGS_ADAPTER.validate_python(completion_args))
+        litellm_completion_response: Final[ModelResponse | litellm.CustomStreamWrapper] = (
+            litellm.completion(**completion_args) if planned_chat is None else execute_planned_chat(planned_chat)
         )
 
+        if planned_chat is not None:
+            _price_planned_chat_response(completion_args, litellm_completion_response)
+
         if isinstance(litellm_completion_response, ModelResponse):
             responses_api_response: Final[ResponsesAPIResponse] = (
                 LiteLLMCompletionResponsesConfig.transform_chat_completion_response_to_responses_api_response(
@@ -122,15 +151,20 @@ class LiteLLMCompletionTransformationHandler:
                 previous_response_client_ids=previous_response_client_ids,
             )
 
-        acompletion_args: Final = {}
-        acompletion_args.update(kwargs)
-        acompletion_args.update(litellm_completion_request)
-        acompletion_args["_skip_responses_api_bridge"] = True
+        acompletion_args: Final = {**kwargs, **litellm_completion_request, "_skip_responses_api_bridge": True}
 
-        litellm_completion_response: Final[ModelResponse | litellm.CustomStreamWrapper] = await litellm.acompletion(
-            **acompletion_args,
+        from litellm.main import aexecute_planned_chat
+
+        planned_chat: Final = _plan_bridged_chat(_REQUEST_KWARGS_ADAPTER.validate_python(acompletion_args))
+        litellm_completion_response: Final[ModelResponse | litellm.CustomStreamWrapper] = (
+            await litellm.acompletion(**acompletion_args)
+            if planned_chat is None
+            else await aexecute_planned_chat(planned_chat)
         )
 
+        if planned_chat is not None:
+            _price_planned_chat_response(acompletion_args, litellm_completion_response)
+
         if isinstance(litellm_completion_response, ModelResponse):
             responses_api_response: Final[ResponsesAPIResponse] = (
                 LiteLLMCompletionResponsesConfig.transform_chat_completion_response_to_responses_api_response(
diff --git a/litellm/responses/litellm_completion_transformation/session_handler.py b/litellm/responses/litellm_completion_transformation/session_handler.py
index 615bdb5bbfb..b2aadc18198 100644
--- a/litellm/responses/litellm_completion_transformation/session_handler.py
+++ b/litellm/responses/litellm_completion_transformation/session_handler.py
@@ -1,8 +1,11 @@
 import asyncio
 import json
-from collections.abc import Mapping
+from collections.abc import Mapping, Sequence
+from itertools import groupby
 from typing import TYPE_CHECKING, Any, Final, cast
 
+from pydantic import TypeAdapter
+
 import litellm
 from litellm._logging import verbose_proxy_logger
 from litellm.constants import REDACTED_BY_LITELLM, REDACTED_TOOL_CALL_ARGUMENTS_PLACEHOLDER
@@ -28,6 +31,7 @@ else:
 # Cold Storage Handler
 ########################################################
 COLD_STORAGE_HANDLER: Final = ColdStorageHandler()
+_STORED_REQUEST: Final = TypeAdapter(dict[str, object])
 ########################################################
 
 
@@ -66,6 +70,76 @@ def _stored_responses_api_output(stored_response: object) -> ResponseInputParam
             return None
 
 
+def _stored_web_search_results(stored_response: object) -> Sequence[Mapping[str, object]]:
+    """The Anthropic ``web_search_tool_result`` blocks a bridged response kept in its ``provider_specific_fields``."""
+    fields: Final = stored_response.get("provider_specific_fields") if isinstance(stored_response, Mapping) else None
+    results: Final = fields.get("web_search_results") if isinstance(fields, Mapping) else None
+    return tuple(result for result in results if isinstance(result, Mapping)) if isinstance(results, list) else ()
+
+
+def _server_web_search_call_id(item: object, web_search_results: Sequence[Mapping[str, object]]) -> str | None:
+    """The ``server_tool_use`` id behind a stored ``web_search_call`` item, when its result block was kept."""
+    if not isinstance(item, Mapping) or item.get("type") != "web_search_call":
+        return None
+    item_id: Final = item.get("id")
+    call_id: Final = item_id.removeprefix("ws_") if isinstance(item_id, str) else None
+    if call_id and any(result.get("tool_use_id") == call_id for result in web_search_results):
+        return call_id
+    return None
+
+
+def _server_web_search_message(items: Sequence[object], web_search_results: Sequence[Mapping[str, object]]) -> Message:
+    """Replay stored web search calls as the assistant tool calls the chat completion carried,
+    so an Anthropic target rebuilds its ``server_tool_use`` / ``web_search_tool_result`` blocks."""
+    calls: Final = tuple(
+        (call_id, item)
+        for item in items
+        if isinstance(item, Mapping) and (call_id := _server_web_search_call_id(item, web_search_results)) is not None
+    )
+    call_ids: Final = frozenset(call_id for call_id, _ in calls)
+    return Message(
+        role="assistant",
+        content=None,
+        tool_calls=[
+            {
+                "id": call_id,
+                "type": "function",
+                "function": {"name": "web_search", "arguments": json.dumps({"query": _web_search_query(item)})},
+            }
+            for call_id, item in calls
+        ],
+        provider_specific_fields={
+            "web_search_results": [result for result in web_search_results if result.get("tool_use_id") in call_ids]
+        },
+    )
+
+
+def _web_search_query(item: Mapping[str, object]) -> str:
+    action: Final = item.get("action")
+    query: Final = action.get("query") if isinstance(action, Mapping) else None
+    return query if isinstance(query, str) else ""
+
+
+_CHAT_MESSAGE_CONTENT_ITEM_TYPES: Final = ("reasoning", "message")
+
+
+def _in_chat_message_order(
+    output: ResponseInputParam, web_search_results: Sequence[Mapping[str, object]]
+) -> ResponseInputParam:
+    """A turn with server web searches in the order its chat completion message replayed it: reasoning, then text,
+    then the tool calls as they happened. Any other turn keeps its output order."""
+    if not any(_server_web_search_call_id(item, web_search_results) is not None for item in output):
+        return output
+    return sorted(
+        output,
+        key=lambda item: (
+            _CHAT_MESSAGE_CONTENT_ITEM_TYPES.index(item_type)
+            if isinstance(item, Mapping) and (item_type := item.get("type")) in _CHAT_MESSAGE_CONTENT_ITEM_TYPES
+            else len(_CHAT_MESSAGE_CONTENT_ITEM_TYPES)
+        ),
+    )
+
+
 def _stored_instructions(proxy_server_request: Mapping[str, object] | None) -> str | None:
     instructions: Final = None if proxy_server_request is None else proxy_server_request.get("instructions")
     return instructions if isinstance(instructions, str) and instructions else None
@@ -189,14 +263,22 @@ class ResponsesSessionHandler:
         ############################################################
         _response_output: Final[object] = spend_log.get("response", "{}")
         if (responses_api_output := _stored_responses_api_output(_response_output)) is not None:
-            chat_completion_message_history.extend(
-                LiteLLMCompletionResponsesConfig.transform_responses_api_input_to_messages(
-                    input=responses_api_output,
-                    responses_api_request={},
-                    replay_reasoning=True,
-                    item_cache_control=item_cache_control,
+            web_search_results: Final = _stored_web_search_results(_response_output)
+            for is_server_web_search, items in groupby(
+                _in_chat_message_order(responses_api_output, web_search_results),
+                key=lambda item: _server_web_search_call_id(item, web_search_results) is not None,
+            ):
+                if is_server_web_search:
+                    chat_completion_message_history.append(_server_web_search_message(tuple(items), web_search_results))
+                    continue
+                chat_completion_message_history.extend(
+                    LiteLLMCompletionResponsesConfig.transform_responses_api_input_to_messages(
+                        input=list(items),
+                        responses_api_request={},
+                        replay_reasoning=True,
+                        item_cache_control=item_cache_control,
+                    )
                 )
-            )
         elif isinstance(_response_output, dict) and _response_output and _response_output != {}:
             # transform `ChatCompletion Response` to `ResponsesAPIResponse`
             model_response: Final = ModelResponse(**_response_output)
@@ -214,30 +296,23 @@ class ResponsesSessionHandler:
         Get the parsed proxy server request from the spend log
         """
         proxy_server_request: Final[str | dict] = spend_log.get("proxy_server_request") or "{}"
-        proxy_server_request_dict: dict[str, object] | None = None
-        if isinstance(proxy_server_request, dict):
-            proxy_server_request_dict = proxy_server_request
-        else:
-            proxy_server_request_dict = json.loads(proxy_server_request)
+        proxy_server_request_dict: Final = _STORED_REQUEST.validate_python(
+            proxy_server_request if isinstance(proxy_server_request, dict) else json.loads(proxy_server_request)
+        )
 
         ############################################################
         # Check if user has setup cold storage for session handling
         ############################################################
-        if ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_server_request_dict):
-            # Try to get cold storage object key from spend log metadata
-            _proxy_server_request_dict: dict | None = None
-            cold_storage_object_key = ResponsesSessionHandler._get_cold_storage_object_key_from_spend_log(spend_log)
-            if cold_storage_object_key:
-                # Use the object key directly from metadata
-                _proxy_server_request_dict = (
-                    await ResponsesSessionHandler.get_proxy_server_request_from_cold_storage_with_object_key(
-                        object_key=cold_storage_object_key,
-                    )
-                )
-            if _proxy_server_request_dict:
-                proxy_server_request_dict = _proxy_server_request_dict
-
-        return proxy_server_request_dict
+        if not ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_server_request_dict):
+            return proxy_server_request_dict
+        cold_storage_object_key: Final = ResponsesSessionHandler._get_cold_storage_object_key_from_spend_log(spend_log)
+        if not cold_storage_object_key:
+            return proxy_server_request_dict
+        return (
+            await ResponsesSessionHandler.get_proxy_server_request_from_cold_storage_with_object_key(
+                object_key=cold_storage_object_key,
+            )
+        ) or proxy_server_request_dict
 
     @staticmethod
     def _get_cold_storage_object_key_from_spend_log(
@@ -279,14 +354,10 @@ class ResponsesSessionHandler:
         """
         verbose_proxy_logger.debug("inside get_proxy_server_request_from_cold_storage_with_object_key...")
 
-        proxy_server_request_dict: Final = (
-            await COLD_STORAGE_HANDLER.get_proxy_server_request_from_cold_storage_with_object_key(
-                object_key=object_key,
-            )
+        return await COLD_STORAGE_HANDLER.get_proxy_server_request_from_cold_storage_with_object_key(
+            object_key=object_key,
         )
 
-        return proxy_server_request_dict
-
     @staticmethod
     def _should_check_cold_storage_for_full_payload(
         proxy_server_request_dict: Mapping[str, object] | None,
diff --git a/tests/unit/responses/litellm_completion_transformation/test_anthropic_responses_bridge.py b/tests/unit/responses/litellm_completion_transformation/test_anthropic_responses_bridge.py
index 025f1315aab..19749d51061 100644
--- a/tests/unit/responses/litellm_completion_transformation/test_anthropic_responses_bridge.py
+++ b/tests/unit/responses/litellm_completion_transformation/test_anthropic_responses_bridge.py
@@ -1,3 +1,4 @@
+import datetime
 import json
 from collections.abc import Mapping, Sequence
 from itertools import chain
@@ -10,6 +11,7 @@ import respx
 from pydantic import BaseModel
 
 import litellm
+from litellm.integrations.custom_logger import CustomLogger
 from litellm.llms.custom_httpx.http_handler import AsyncHTTPHandler
 from litellm.responses.litellm_completion_transformation.handler import (
     LiteLLMCompletionTransformationHandler,
@@ -86,8 +88,8 @@ async def test_aresponses_forwards_timeout_to_acompletion():
     and similar providers, with calls falling back to the provider SDK default
     (~600s for Anthropic).
     """
-    with patch("litellm.acompletion", new_callable=AsyncMock) as mock_acompletion:
-        mock_acompletion.return_value = ModelResponse(
+    with patch("litellm.main.aexecute_planned_chat", new_callable=AsyncMock) as mock_chat:
+        mock_chat.return_value = ModelResponse(
             id="id",
             created=0,
             model="anthropic/claude-sonnet-4-5",
@@ -102,8 +104,8 @@ async def test_aresponses_forwards_timeout_to_acompletion():
             api_key="sk-ant-fake",
         )
 
-    assert mock_acompletion.call_count == 1
-    forwarded_timeout = mock_acompletion.call_args.kwargs.get("timeout")
+    assert mock_chat.call_count == 1
+    forwarded_timeout = mock_chat.call_args.args[0].named.get("timeout")
     assert forwarded_timeout == 42, (
         f"timeout was not forwarded to acompletion (got {forwarded_timeout!r}); "
         "this means Router(timeout=N) silently fails for providers on the "
@@ -541,3 +543,153 @@ def test_streamed_responses_over_anthropic_emit_the_responses_event_sequence(res
     assert deltas == "Argentina won."
     assert completed.response.status == "completed"
     assert completed.response.output[0].content[0].text == "Argentina won."
+
+
+class _DeploymentHookCounter(CustomLogger):
+    def __init__(self) -> None:
+        super().__init__()
+        self.calls = 0
+
+    async def async_pre_call_deployment_hook(self, kwargs: Mapping[str, object], call_type: object) -> None:
+        self.calls += 1
+
+
+@pytest.mark.asyncio
+async def test_bridged_responses_call_runs_deployment_hooks_once(monkeypatch: pytest.MonkeyPatch):
+    counter: Final = _DeploymentHookCounter()
+    monkeypatch.setattr(litellm, "callbacks", [counter])
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    litellm.in_memory_llm_clients_cache.flush_cache()
+
+    with respx.mock(assert_all_called=False) as upstream:
+        messages_route: Final = upstream.post("http://anthropic.test/v1/messages").mock(
+            return_value=httpx.Response(
+                200,
+                json={
+                    "id": "msg_bridge",
+                    "type": "message",
+                    "role": "assistant",
+                    "model": "claude-bridge",
+                    "content": [{"type": "text", "text": "from upstream"}],
+                    "stop_reason": "end_turn",
+                    "stop_sequence": None,
+                    "usage": {"input_tokens": 10, "output_tokens": 5},
+                },
+            )
+        )
+        response: Final = await litellm.aresponses(
+            model="anthropic/claude-bridge", input="hi", api_base="http://anthropic.test", api_key="sk-test"
+        )
+
+    assert response.output[0].content[0].text == "from upstream"
+    assert messages_route.call_count == 1
+    assert counter.calls == 1
+
+
+@pytest.mark.asyncio
+async def test_bridged_responses_call_is_billed_like_the_chat_call_for_one_hour_cache_writes_and_web_searches(
+    monkeypatch: pytest.MonkeyPatch,
+):
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    litellm.in_memory_llm_clients_cache.flush_cache()
+    usage: Final = {
+        "input_tokens": 100,
+        "output_tokens": 50,
+        "cache_creation_input_tokens": 2000,
+        "cache_read_input_tokens": 3000,
+        "cache_creation": {"ephemeral_5m_input_tokens": 0, "ephemeral_1h_input_tokens": 2000},
+        "server_tool_use": {"web_search_requests": 2},
+    }
+    upstream_message: Final = {
+        "id": "msg_bridge_cost",
+        "type": "message",
+        "role": "assistant",
+        "model": "claude-sonnet-4-5",
+        "content": [{"type": "text", "text": "searched"}],
+        "stop_reason": "end_turn",
+        "stop_sequence": None,
+        "usage": usage,
+    }
+    credentials: Final = {"api_base": "http://anthropic.test", "api_key": "sk-test"}
+
+    with respx.mock(assert_all_called=False) as upstream:
+        upstream.post("http://anthropic.test/v1/messages").mock(return_value=httpx.Response(200, json=upstream_message))
+        chat: Final = await litellm.acompletion(
+            model="anthropic/claude-sonnet-4-5", messages=[{"role": "user", "content": "hi"}], **credentials
+        )
+        bridged: Final = await litellm.aresponses(model="anthropic/claude-sonnet-4-5", input="hi", **credentials)
+
+    chat_cost: Final = chat._hidden_params["response_cost"]
+    assert isinstance(chat_cost, float) and chat_cost > 0
+    assert bridged._hidden_params["response_cost"] == pytest.approx(chat_cost)
+
+
+_ANTHROPIC_MESSAGE: Final = {
+    "id": "msg_bridge_headers",
+    "type": "message",
+    "role": "assistant",
+    "model": "claude-sonnet-4-5",
+    "content": [{"type": "text", "text": "hi"}],
+    "stop_reason": "end_turn",
+    "stop_sequence": None,
+    "usage": {"input_tokens": 10, "output_tokens": 5},
+}
+
+
+@pytest.mark.asyncio
+async def test_bridged_responses_call_names_the_provider_request_id_in_its_headers(monkeypatch: pytest.MonkeyPatch):
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    litellm.in_memory_llm_clients_cache.flush_cache()
+
+    with respx.mock(assert_all_called=False) as upstream:
+        upstream.post("http://anthropic.test/v1/messages").mock(
+            return_value=httpx.Response(200, json=_ANTHROPIC_MESSAGE, headers={"x-request-id": "req-upstream-1"})
+        )
+        bridged: Final = await litellm.aresponses(
+            model="anthropic/claude-sonnet-4-5", input="hi", api_base="http://anthropic.test", api_key="sk-test"
+        )
+
+    assert bridged._hidden_params["additional_headers"]["llm_provider-request-id"] == "req-upstream-1"
+
+
+@pytest.mark.asyncio
+async def test_bridged_responses_stream_opens_with_the_cost_breakdown_headers(monkeypatch: pytest.MonkeyPatch):
+    from litellm.litellm_core_utils.litellm_logging import Logging
+    from litellm.proxy.common_request_processing import cost_headers
+
+    monkeypatch.setattr(litellm, "disable_aiohttp_transport", True)
+    litellm.in_memory_llm_clients_cache.flush_cache()
+    logging_obj: Final = Logging(
+        model="anthropic/claude-sonnet-4-5",
+        messages=[{"role": "user", "content": "hi"}],
+        stream=True,
+        call_type="aresponses",
+        start_time=datetime.datetime.now(datetime.timezone.utc),
+        litellm_call_id="bridge-stream-headers-0000-4000-8000-000000000001",
+        function_id="1234",
+    )
+    events: Final = (
+        {"type": "message_start", "message": {**_ANTHROPIC_MESSAGE, "content": [], "stop_reason": None}},
+        {"type": "message_stop"},
+    )
+    sse: Final = "".join(f"event: {event['type']}\ndata: {json.dumps(event)}\n\n" for event in events)
+
+    with respx.mock(assert_all_called=False) as upstream:
+        upstream.post("http://anthropic.test/v1/messages").mock(
+            return_value=httpx.Response(200, headers={"content-type": "text/event-stream"}, text=sse)
+        )
+        stream: Final = await litellm.aresponses(
+            model="anthropic/claude-sonnet-4-5",
+            input="hi",
+            stream=True,
+            api_base="http://anthropic.test",
+            api_key="sk-test",
+            litellm_logging_obj=logging_obj,
+        )
+        headers: Final = cost_headers(None, logging_obj)
+        async for _ in stream:
+            pass
+
+    assert headers["x-litellm-response-cost-output"] == "0.0"
+    assert headers["x-litellm-response-cost-discount-amount"] == "0.0"
+    assert headers["x-litellm-response-cost-margin-amount"] == "0.0"
diff --git a/tests/unit/responses/litellm_completion_transformation/test_google_ai_studio_responses_bridge.py b/tests/unit/responses/litellm_completion_transformation/test_google_ai_studio_responses_bridge.py
index 24db797f53b..8aa03d7629a 100644
--- a/tests/unit/responses/litellm_completion_transformation/test_google_ai_studio_responses_bridge.py
+++ b/tests/unit/responses/litellm_completion_transformation/test_google_ai_studio_responses_bridge.py
@@ -31,8 +31,8 @@ async def test_mock_basic_google_ai_studio_responses_api_with_tools():
         ],
     )
 
-    with patch("litellm.acompletion", new_callable=AsyncMock) as mock_acompletion:
-        mock_acompletion.return_value = mock_response
+    with patch("litellm.main.aexecute_planned_chat", new_callable=AsyncMock) as mock_chat:
+        mock_chat.return_value = mock_response
 
         request_model = "gemini/gemini-2.5-flash"
         await litellm.aresponses(
@@ -41,11 +41,10 @@ async def test_mock_basic_google_ai_studio_responses_api_with_tools():
             tools=[{"type": "web_search_preview", "search_context_size": "low"}],
         )
 
-        # Verify that acompletion was called
-        assert mock_acompletion.called
+        assert mock_chat.called
 
-        # Get the call arguments
-        call_args, call_kwargs = mock_acompletion.call_args
+        plan = mock_chat.call_args.args[0]
+        call_kwargs = {**plan.kwargs, **plan.named}
 
         # Verify the expected parameters were passed
         print(
@@ -65,5 +64,5 @@ async def test_mock_basic_google_ai_studio_responses_api_with_tools():
             call_kwargs["messages"][0]["content"]
             == "what is the latest version of supabase python package and when was it released?"
         )
-        assert "tools" not in call_kwargs
-        assert "tool_choice" not in call_kwargs
+        assert call_kwargs.get("tools") is None
+        assert call_kwargs.get("tool_choice") is None
diff --git a/tests/unit/responses/litellm_completion_transformation/test_session_handler.py b/tests/unit/responses/litellm_completion_transformation/test_session_handler.py
index 7a146c1b665..6738d6c5c99 100644
--- a/tests/unit/responses/litellm_completion_transformation/test_session_handler.py
+++ b/tests/unit/responses/litellm_completion_transformation/test_session_handler.py
@@ -233,11 +233,10 @@ async def test_e2e_cold_storage_successful_retrieval():
         patch.object(session_handler, "COLD_STORAGE_HANDLER") as mock_cold_storage,
         patch("litellm.cold_storage_custom_logger", return_value="s3"),
     ):
-
         # Setup mocks
         mock_get_spend_logs.return_value = mock_spend_logs
-        mock_cold_storage.get_proxy_server_request_from_cold_storage_with_object_key = (
-            AsyncMock(return_value=full_proxy_request)
+        mock_cold_storage.get_proxy_server_request_from_cold_storage_with_object_key = AsyncMock(
+            return_value=full_proxy_request
         )
 
         # Call the main function
@@ -291,7 +290,6 @@ async def test_e2e_cold_storage_fallback_to_truncated_payload():
         ) as mock_get_spend_logs,
         patch.object(session_handler, "COLD_STORAGE_HANDLER") as mock_cold_storage,
     ):
-
         # Setup mocks
         mock_get_spend_logs.return_value = mock_spend_logs
 
@@ -358,41 +356,25 @@ async def test_should_check_cold_storage_for_full_payload():
 
     with patch("litellm.cold_storage_custom_logger", return_value="s3"):
         # Test case 1: Should return True for truncated content
-        result1 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(
-            proxy_request_with_truncated_pdf
-        )
-        assert (
-            result1 == True
-        ), "Should return True for proxy request with truncated PDF content"
+        result1 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_request_with_truncated_pdf)
+        assert result1 == True, "Should return True for proxy request with truncated PDF content"
 
         # Test case 2: Should return False for regular content
-        result2 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(
-            proxy_request_regular
-        )
-        assert (
-            result2 == False
-        ), "Should return False for regular proxy request without truncation"
+        result2 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_request_regular)
+        assert result2 == False, "Should return False for regular proxy request without truncation"
 
         # Test case 3: Should return True for empty request
-        result3 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(
-            proxy_request_empty
-        )
+        result3 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_request_empty)
         assert result3 == True, "Should return True for empty proxy request"
 
         # Test case 4: Should return True for None request
-        result4 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(
-            proxy_request_none
-        )
+        result4 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_request_none)
         assert result4 == True, "Should return True for None proxy request"
 
     # Test case 5: Should return False when cold storage is not configured
     with patch.object(litellm, "cold_storage_custom_logger", None):
-        result5 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(
-            proxy_request_with_truncated_pdf
-        )
-        assert (
-            result5 == False
-        ), "Should return False when cold storage is not configured, even with truncated content"
+        result5 = ResponsesSessionHandler._should_check_cold_storage_for_full_payload(proxy_request_with_truncated_pdf)
+        assert result5 == False, "Should return False when cold storage is not configured, even with truncated content"
 
 
 @pytest.mark.asyncio
@@ -422,9 +404,7 @@ async def test_get_chat_completion_message_history_empty_response_dict():
         }
     ]
 
-    with patch.object(
-        ResponsesSessionHandler, "get_all_spend_logs_for_previous_response_id"
-    ) as mock_get_spend_logs:
+    with patch.object(ResponsesSessionHandler, "get_all_spend_logs_for_previous_response_id") as mock_get_spend_logs:
         mock_get_spend_logs.return_value = mock_spend_logs
 
         # Call the function
@@ -518,9 +498,7 @@ async def test_message_history_reconstructs_list_shaped_input():
     ) as mock_get_spend_logs:
         mock_get_spend_logs.return_value = mock_spend_logs
 
-        result = await ResponsesSessionHandler.get_chat_completion_message_history_for_previous_response_id(
-            request_id
-        )
+        result = await ResponsesSessionHandler.get_chat_completion_message_history_for_previous_response_id(request_id)
 
     messages = result["messages"]
     assert [(message.get("role"), message.get("content")) for message in messages] == [
@@ -549,9 +527,7 @@ async def test_message_history_retries_a_spend_log_the_batch_writer_has_not_flus
     fake_prisma_client = _FakePrismaClient(results=[[], [spend_log]])
 
     with patch("litellm.proxy.proxy_server.prisma_client", fake_prisma_client):
-        result = await ResponsesSessionHandler.get_chat_completion_message_history_for_previous_response_id(
-            request_id
-        )
+        result = await ResponsesSessionHandler.get_chat_completion_message_history_for_previous_response_id(request_id)
 
     messages = result["messages"]
     assert [(message.get("role"), message.get("content")) for message in messages] == [
@@ -618,14 +594,10 @@ async def test_message_history_looks_up_the_decoded_chat_completion_id():
         model_id="e0f302a1412e78470ebb28cbed01fff5f88c0d331c667e9f2ba4b413c6fbd282",
         response_id=request_id,
     )
-    fake_prisma_client = _FakePrismaClient(
-        results=[[_spend_log(request_id, "session-a", "Hello.", "Hi.")]]
-    )
+    fake_prisma_client = _FakePrismaClient(results=[[_spend_log(request_id, "session-a", "Hello.", "Hi.")]])
 
     with patch("litellm.proxy.proxy_server.prisma_client", fake_prisma_client):
-        await ResponsesSessionHandler.get_all_spend_logs_for_previous_response_id(
-            encoded_response_id
-        )
+        await ResponsesSessionHandler.get_all_spend_logs_for_previous_response_id(encoded_response_id)
 
     assert len(fake_prisma_client.db.calls) == 1
     assert request_id in fake_prisma_client.db.calls[0]
@@ -724,8 +696,9 @@ async def test_session_lookup_does_not_retry_when_spend_logs_are_disabled(
     """
     fake_prisma_client = _FakePrismaClient(results=[])
 
-    with patch("litellm.proxy.proxy_server.prisma_client", fake_prisma_client), patch(
-        "litellm.proxy.proxy_server.disable_spend_logs", True
+    with (
+        patch("litellm.proxy.proxy_server.prisma_client", fake_prisma_client),
+        patch("litellm.proxy.proxy_server.disable_spend_logs", True),
     ):
         spend_logs = await ResponsesSessionHandler.get_all_spend_logs_for_previous_response_id(
             "chatcmpl-does-not-exist"
@@ -741,7 +714,11 @@ def test_normalize_redacted_arguments_skips_custom_tool_calls():
         content=None,
         tool_calls=[
             {"id": "call_c", "type": "custom", "custom": {"name": "run_code", "input": "print(1)"}},
-            {"id": "call_f", "type": "function", "function": {"name": "get_weather", "arguments": "redacted-by-litellm"}},
+            {
+                "id": "call_f",
+                "type": "function",
+                "function": {"name": "get_weather", "arguments": "redacted-by-litellm"},
+            },
         ],
     )
 
@@ -796,11 +773,13 @@ async def test_message_history_normalizes_redacted_tool_call_arguments():
         }
     ]
 
-    with patch.object(  # test-quality-ok: the handler has no DI seam for the spend-log fetch; every test in this file stubs this same boundary
-        ResponsesSessionHandler,
-        "get_all_spend_logs_for_previous_response_id",
-        new_callable=AsyncMock,
-    ) as mock_get_spend_logs:
+    with (
+        patch.object(  # test-quality-ok: the handler has no DI seam for the spend-log fetch; every test in this file stubs this same boundary
+            ResponsesSessionHandler,
+            "get_all_spend_logs_for_previous_response_id",
+            new_callable=AsyncMock,
+        ) as mock_get_spend_logs
+    ):
         mock_get_spend_logs.return_value = mock_spend_logs
 
         result = await ResponsesSessionHandler.get_chat_completion_message_history_for_previous_response_id(
@@ -889,7 +868,9 @@ class _SqliteBackedPrismaDB:
         self._connection.executemany('INSERT INTO "LiteLLM_SpendLogs" VALUES (?, ?, ?, ?, ?, ?)', rows)
 
     async def query_raw(self, query: str, *args: object) -> list[dict[str, object]]:
-        sqlite_query: Final = query.replace("= ANY($1::text[])", "IN (SELECT value FROM json_each(?))").replace("$1", "?")
+        sqlite_query: Final = query.replace("= ANY($1::text[])", "IN (SELECT value FROM json_each(?))").replace(
+            "$1", "?"
+        )
         sqlite_args: Final = tuple(json.dumps(arg) if isinstance(arg, list) else arg for arg in args)
         return [dict(row) for row in self._connection.execute(sqlite_query, sqlite_args)]
 
@@ -955,3 +936,134 @@ async def test_session_lookup_follows_the_owner_across_keys_and_keeps_ownerless_
 
     assert await _history_request_ids(sqlite_db, "alice-new-key") == ["alice-old-key", "alice-new-key"]
     assert await _history_request_ids(sqlite_db, "ownerless-2") == ["ownerless-2"]
+
+
+def _text(content: object) -> object:
+    if isinstance(content, list):
+        return "".join(part["text"] for part in content)
+    return content
+
+
+def _responses_spend_log(request_id: str, session_id: str, prompt: str, output: list[dict[str, object]]) -> dict:
+    return {
+        "request_id": request_id,
+        "call_type": "aresponses",
+        "session_id": session_id,
+        "proxy_server_request": {"input": [{"role": "user", "content": prompt}], "model": "claude-bridge"},
+        "response": {"id": request_id, "object": "response", "status": "completed", "output": output},
+    }
+
+
+@pytest.mark.asyncio
+async def test_message_history_reads_responses_shaped_rows_next_to_chat_shaped_rows():
+    session_id = "0f6f2d8e-6c8a-4b55-9a39-3d0b1f3c9e11"
+    fake_prisma_client = _FakePrismaClient(
+        results=[
+            [
+                _spend_log("chatcmpl-3333", session_id, "My favorite color is chartreuse.", "Got it."),
+                _responses_spend_log(
+                    "resp_4444",
+                    session_id,
+                    "What is the weather in Lisbon?",
+                    [
+                        {
+                            "type": "message",
+                            "id": "msg_1",
+                            "role": "assistant",
+                            "status": "completed",
+                            "content": [{"type": "output_text", "text": "Let me check.", "annotations": []}],
+                        },
+                        {
+                            "type": "function_call",
+                            "id": "fc_1",
+                            "call_id": "call_weather",
+                            "name": "get_weather",
+                            "arguments": '{"city": "Lisbon"}',
+                        },
+                    ],
+                ),
+            ]
+        ]
+    )
+
+    with patch("litellm.proxy.proxy_server.prisma_client", fake_prisma_client):
+        result = await ResponsesSessionHandler.get_chat_completion_message_history_for_previous_response_id("resp_4444")
+
+    messages: Final = result["messages"]
+    assert [(message.get("role"), _text(message.get("content"))) for message in messages[:4]] == [
+        ("user", "My favorite color is chartreuse."),
+        ("assistant", "Got it."),
+        ("user", "What is the weather in Lisbon?"),
+        ("assistant", "Let me check."),
+    ]
+    tool_calls: Final = [call for message in messages[3:] for call in message.get("tool_calls") or []]
+    assert [(call["id"], call["function"]["name"], call["function"]["arguments"]) for call in tool_calls] == [
+        ("call_weather", "get_weather", '{"city": "Lisbon"}')
+    ]
+
+
+_WEB_SEARCH_RESULT: Final = {
+    "type": "web_search_tool_result",
+    "tool_use_id": "srvtoolu_1",
+    "content": [{"type": "web_search_result", "url": "https://x.com", "title": "X", "encrypted_content": "EC"}],
+}
+
+
+def _bridged_anthropic_web_search_turn() -> dict[str, object]:
+    """A Claude turn served through the Responses to chat bridge, stored as its Responses object."""
+    return {
+        "id": "resp_1",
+        "object": "response",
+        "output": [
+            {
+                "id": "ws_srvtoolu_1",
+                "type": "web_search_call",
+                "status": "completed",
+                "action": {
+                    "type": "search",
+                    "query": "weather sf",
+                    "sources": [{"type": "url", "url": "https://x.com"}],
+                },
+            },
+            {
+                "type": "message",
+                "id": "msg_1",
+                "role": "assistant",
+                "status": "completed",
+                "content": [{"type": "output_text", "text": "It is sunny.", "annotations": []}],
+            },
+        ],
+        "provider_specific_fields": {"web_search_results": [_WEB_SEARCH_RESULT]},
+    }
+
+
+def test_message_history_replays_a_bridged_anthropic_web_search_as_server_tool_blocks():
+    from litellm.litellm_core_utils.prompt_templates.factory import anthropic_messages_pt
+
+    history: Final = ResponsesSessionHandler.extend_chat_completion_message_with_spend_log_payload(
+        spend_log={"request_id": "resp_1", "response": _bridged_anthropic_web_search_turn()},
+        proxy_server_request_dict={"input": "weather in sf?"},
+        chat_completion_message_history=[],
+    )
+    anthropic_messages: Final = anthropic_messages_pt(
+        messages=history, model="claude-sonnet-4-5", llm_provider="anthropic"
+    )
+
+    assert [message["role"] for message in anthropic_messages] == ["user", "assistant"]
+    assistant_content: Final = anthropic_messages[1]["content"]
+    assert [block["type"] for block in assistant_content] == ["text", "server_tool_use", "web_search_tool_result"]
+    assert assistant_content[1]["id"] == "srvtoolu_1"
+    assert assistant_content[1]["input"] == {"query": "weather sf"}
+    assert assistant_content[2]["content"] == _WEB_SEARCH_RESULT["content"]
+
+
+def test_message_history_keeps_a_web_search_without_a_stored_result_as_text():
+    turn: Final = {**_bridged_anthropic_web_search_turn(), "provider_specific_fields": None}
+
+    history: Final = ResponsesSessionHandler.extend_chat_completion_message_with_spend_log_payload(
+        spend_log={"request_id": "resp_1", "response": turn},
+        proxy_server_request_dict=None,
+        chat_completion_message_history=[],
+    )
+
+    assert str(_text_of(history[0]["content"])).startswith("Hosted web search: ")