fix(managed_files): skip user content the file-id scan cannot read instead of answering 500 or an AttributeError 400

enterprise/litellm_enterprise/proxy/hooks/managed_files.py

@@ -2,6 +2,7 @@
 ## This hook is used to check for LiteLLM managed files in the request body, and replace them with model-specific file id
 
 import base64
+import itertools
 import json
 from collections.abc import Iterator, Mapping, Sequence
 from types import MappingProxyType
@@ -255,6 +256,22 @@ def _storage_metadata_of(file_object: OpenAIFileObject | None) -> Mapping[str, s
 _MANAGED_FILES_TARGET: Final = "managed_files"
 
 
+def _user_content_parts(message: AllMessageValues) -> tuple[object, ...]:
+    match message:
+        case {"role": "user", "content": list() as parts}:
+            return tuple(parts)
+        case _:
+            return ()
+
+
+def _file_id_of_content_part(part: object) -> str | None:
+    match part:
+        case {"type": "file", "file": {"file_id": str() as file_id}} if file_id:
+            return file_id
+        case _:
+            return None
+
+
 class _PROXY_LiteLLMManagedFiles(CustomLogger, BaseFileEndpoints):
     # Class variables or attributes
     def __init__(self, internal_usage_cache: InternalUsageCache, prisma_client: PrismaClient):
@@ -1056,21 +1073,8 @@ class _PROXY_LiteLLMManagedFiles(CustomLogger, BaseFileEndpoints):
         """
         Gets file ids from messages
         """
-        file_ids = []
-        for message in messages:
-            if message.get("role") == "user":
-                content = message.get("content")
-                if content:
-                    if isinstance(content, str):
-                        continue
-                    for c in content:
-                        if c.get("type") == "file":
-                            file_object = cast(ChatCompletionFileObject, c)
-                            file_object_file_field = file_object["file"]
-                            file_id = file_object_file_field.get("file_id")
-                            if file_id:
-                                file_ids.append(file_id)
-        return file_ids
+        parts: Final = itertools.chain.from_iterable(_user_content_parts(message) for message in messages)
+        return [file_id for file_id in map(_file_id_of_content_part, parts) if file_id]
 
     def get_file_ids_from_responses_input(self, input: Union[str, List[Dict[str, object]]]) -> List[str]:
         """

tests/integration/providers/test_ollama_prompt_tools_wire.py

@@ -1198,14 +1198,20 @@ def test_malformed_content_is_a_400_naming_the_message_and_field(
 
 
 @pytest.mark.parametrize(
-    "content",
+    ("content", "detail"),
     [
-        pytest.param(22, id="user-int-content"),
-        pytest.param({"text": _QUESTION}, id="user-dict-content"),
-        pytest.param(["just a string"], id="user-string-part"),
+        pytest.param(22, "has int content; content must be a string or a list of content parts", id="user-int-content"),
+        pytest.param(
+            {"text": _QUESTION},
+            "has dict content; content must be a string or a list of content parts",
+            id="user-dict-content",
+        ),
+        pytest.param(["just a string"], "has a str content part; content parts must be objects", id="user-string-part"),
     ],
 )
-def test_non_list_user_content_is_rejected_before_it_reaches_ollama(gateway: Gateway, content: JsonValue) -> None:
+def test_non_list_user_content_is_rejected_before_it_reaches_ollama(
+    gateway: Gateway, content: JsonValue, detail: str
+) -> None:
     with _ollama_server(lambda _: _generate_reply(_ANSWER)) as wire, gateway.scenario() as scenario:
         model: Final = scenario.model(model=f"ollama/{_BACKEND}", api_base=wire.url, api_key=_API_KEY)
         code, text = _post(
@@ -1213,8 +1219,8 @@ def test_non_list_user_content_is_rejected_before_it_reaches_ollama(gateway: Gat
             "/v1/chat/completions",
             {"model": model, "messages": [{"role": "user", "content": content}], "tools": [_WEATHER_TOOL]},
         )
-        assert code >= 400, text
-        assert _error_message(text), text
+        assert code == 400, text
+        assert f"the user message at index 0 {detail}" in _error_message(text), text
         assert _generate_calls(wire) == ()
         payload: Final = _post_chat(gateway, model, _second_turn(), tools=[_WEATHER_TOOL])
         assert json.dumps(payload["choices"]).count(_ANSWER) == 1, payload

tests/unit/enterprise/proxy/hooks/test_managed_files.py

@@ -73,6 +73,43 @@ def test_get_file_ids_from_messages_skips_bedrock_content_blocks_without_type():
     assert file_ids == ["file-keep"]
 
 
+_UNSCANNABLE_USER_CONTENT = [
+    pytest.param(22, id="int-content"),
+    pytest.param({"text": "hi"}, id="dict-content"),
+    pytest.param(["hi"], id="string-part"),
+]
+
+
+@pytest.mark.parametrize("content", _UNSCANNABLE_USER_CONTENT)
+def test_get_file_ids_from_messages_skips_content_it_cannot_scan(content):
+    proxy_managed_files = PROXY_LiteLLMManagedFiles(DualCache(), prisma_client=MagicMock())
+    messages = [
+        {"role": "user", "content": content},
+        {"role": "user", "content": [{"type": "file", "file": {"file_id": "file-keep"}}]},
+    ]
+    assert proxy_managed_files.get_file_ids_from_messages(messages) == ["file-keep"]
+
+
+@pytest.mark.asyncio
+@pytest.mark.parametrize("content", _UNSCANNABLE_USER_CONTENT)
+async def test_async_pre_call_hook_passes_unscannable_user_content_through_untouched(content):
+    from litellm.proxy._types import UserAPIKeyAuth
+
+    prisma_client = AsyncMock()
+    proxy_managed_files = PROXY_LiteLLMManagedFiles(DualCache(), prisma_client=prisma_client)
+    data = {"messages": [{"role": "user", "content": content}], "model": "gpt-5.5"}
+
+    result = await proxy_managed_files.async_pre_call_hook(
+        user_api_key_dict=UserAPIKeyAuth(user_id="123", parent_otel_span=MagicMock()),
+        cache=DualCache(),
+        data=data,
+        call_type="acompletion",
+    )
+
+    assert result == {"messages": [{"role": "user", "content": content}], "model": "gpt-5.5"}
+    assert prisma_client.mock_calls == []
+
+
 @pytest.mark.asyncio
 async def test_async_pre_call_hook_batch_retrieve():
     from litellm.proxy._types import UserAPIKeyAuth