diff --git a/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py b/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py
index fdba9f82f10..2f0cbc0d474 100644
--- a/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py
+++ b/litellm/router_utils/pre_call_checks/prompt_caching_deployment_check.py
@@ -6,6 +6,7 @@ Route to previously cached model id, if valid
 
 import secrets
 from collections.abc import Awaitable, Callable, Iterator, Mapping, Sequence
+from itertools import chain
 from types import MappingProxyType
 from typing import Final, NamedTuple, Protocol, TypedDict, cast
 
@@ -29,6 +30,7 @@ from litellm.responses.litellm_completion_transformation.transformation import (
     RESPONSES_TOOL_TYPES_WITHOUT_CHAT_FORM,
     RESPONSES_WEB_SEARCH_TOOL_TYPES,
     LiteLLMCompletionResponsesConfig,
+    ResponsesToolChatForm,
     ResponseTools,
 )
 from litellm.responses.utils import ResponsesAPIRequestUtils
@@ -82,6 +84,20 @@ def new_responses_pins_in_flight() -> ResponsesPinsInFlight:
     )
 
 
+def _key_chat_tool(source: Mapping[str, object], chat_tool: Mapping[str, object]) -> Mapping[str, object]:
+    function: Final = as_str_mapping(chat_tool.get("function"))
+    if source.get("type") != "function" or function is None:
+        return chat_tool
+    return {**chat_tool, "function": {key: source[key] for key in function if key in source}}
+
+
+def _key_chat_tools(
+    sources: Sequence[Mapping[str, object]], forms: Sequence[ResponsesToolChatForm]
+) -> Iterator[Mapping[str, object]]:
+    for source, form in zip(sources, forms, strict=True):
+        yield from (_key_chat_tool(source, chat_tool) for chat_tool in form.chat_tools)
+
+
 def _responses_prompt(request_data: Mapping[str, object]) -> _ResponsesPrompt | None:
     request_input: Final = request_data.get("input")
     request_tools: Final = request_data.get("tools")
@@ -107,13 +123,12 @@ def _responses_prompt(request_data: Mapping[str, object]) -> _ResponsesPrompt |
             item_cache_control=True,
             only_since_compaction=True,
         )
-        tools, _ = LiteLLMCompletionResponsesConfig.transform_responses_api_tools_to_chat_completion_tools(
-            convertible_tools
-        )
+        forms: Final = LiteLLMCompletionResponsesConfig.responses_tools_to_chat_forms(convertible_tools)
     except Exception as error:  # noqa: BLE001  # the provider judges the input, a routing preference never does
         verbose_logger.debug("Prompt Caching: skipping an input with no chat form: %s", type(error).__name__)
         return None
-    key_tools: Final = [*tools, *tools_kept_as_sent]
+    tools: Final = list(chain.from_iterable(form.chat_tools for form in forms))
+    key_tools: Final = [*_key_chat_tools(convertible_tools or (), forms), *tools_kept_as_sent]
     return _ResponsesPrompt(
         messages=cast(list[AllMessageValues], messages),  # cast-ok: the bridge's chat messages, read as plain JSON
         tools=cast(list[AllToolParamValues], tools) or None,  # cast-ok: the bridge's chat tools, read as plain JSON
@@ -465,10 +480,12 @@ class PromptCachingDeploymentCheck(CustomLogger):
 
     def _take_responses_pin(self, kwargs: _PromptCachingSuccessEventKwargs) -> object:
         litellm_params: Final = kwargs.get("litellm_params") or {}
-        metadata: Final = as_str_mapping(litellm_params.get("litellm_metadata")) or {}
-        pin_token: Final = metadata.get(_RESPONSES_PIN_METADATA_KEY)
+        metadata: Final = litellm_params.get("litellm_metadata")
+        pin_token: Final = (as_str_mapping(metadata) or {}).get(_RESPONSES_PIN_METADATA_KEY)
         if not isinstance(pin_token, str):
             return None
+        if isinstance(metadata, dict):
+            metadata.pop(_RESPONSES_PIN_METADATA_KEY, None)  # pyright: ignore[reportUnknownMemberType]  # the caller's metadata dict
         recorded_pin: Final = self.responses_pins_in_flight.get_cache(pin_token)
         self.responses_pins_in_flight.delete_cache(pin_token)
         return recorded_pin
diff --git a/tests/unit/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py b/tests/unit/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py
index 34cb1811488..568cc4a618c 100644
--- a/tests/unit/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py
+++ b/tests/unit/router_utils/pre_call_checks/test_prompt_caching_deployment_check.py
@@ -2096,6 +2096,35 @@ async def test_responses_with_another_tool_set_are_a_different_prefix():
     assert len(pinned) == 2
 
 
+@pytest.mark.asyncio
+async def test_chat_and_responses_requests_sending_the_same_tool_share_one_prefix():
+    described_tool: Final = {**_RESPONSES_TOOL, "description": "Get the time"}
+    chat_tool: Final = {
+        "type": "function",
+        "function": {key: value for key, value in described_tool.items() if key != "type"},
+    }
+    router: Final = _responses_router(RESPONSES_BRIDGED_MODEL)
+    await router.acompletion(
+        model=MODEL_GROUP_ALIAS,
+        messages=[
+            {"role": "system", "content": [{**_marked_input_text(LONG_PROMPT), "type": "text"}]},
+            {"role": "user", "content": "hello"},
+        ],
+        tools=[chat_tool],
+        mock_response="ok",
+    )
+    assert await _eventually(lambda: router.prompt_caching_pin_cache.in_memory_cache.cache_dict)
+    chat_pin_keys: Final = set(router.prompt_caching_pin_cache.in_memory_cache.cache_dict)
+    router.prompt_caching_pin_cache.in_memory_cache.flush_cache()
+
+    await router.aresponses(
+        model=MODEL_GROUP_ALIAS, input=_marked_responses_input(), tools=[described_tool], mock_response="ok"
+    )
+
+    assert await _eventually(lambda: router.prompt_caching_pin_cache.in_memory_cache.cache_dict)
+    assert set(router.prompt_caching_pin_cache.in_memory_cache.cache_dict) == chat_pin_keys
+
+
 @pytest.mark.asyncio
 async def test_responses_marked_tool_set_long_enough_to_cache_pins_on_its_own():
     marked_tool = {**_RESPONSES_TOOL, "description": LONG_PROMPT, "cache_control": {"type": "ephemeral"}}
@@ -2413,6 +2442,22 @@ async def test_logger_serializing_the_request_metadata_never_sees_the_prompt_cac
     assert not [pin_key for pin_key in pin_keys if pin_key.split(":")[1] in logged_metadata]
 
 
+@pytest.mark.asyncio
+async def test_responses_call_hands_back_the_callers_metadata_without_the_pin_token():
+    router: Final = _responses_router(RESPONSES_BRIDGED_MODEL)
+    caller_metadata: Final[dict[str, object]] = {"tags": ["team-a"]}
+
+    await router.aresponses(
+        model=MODEL_GROUP_ALIAS,
+        input=_marked_responses_input(),
+        litellm_metadata=caller_metadata,
+        mock_response="ok",
+    )
+
+    assert await _eventually(lambda: router.prompt_caching_pin_cache.in_memory_cache.cache_dict)
+    assert "responses_prompt_cache_pin" not in caller_metadata
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize(
     "failed_in_request,expected_deployments",