Merge 955484ee1d into 2e27a02a9f

litellm/llms/anthropic/chat/guardrail_translation/handler.py

@@ -52,6 +52,7 @@ from litellm.llms.base_llm.guardrail_translation.utils import (
     effective_scan_only_tool_results_for_guardrail,
     effective_skip_system_message_for_guardrail,
     effective_skip_tool_message_for_guardrail,
+    extract_tool_from_addition_block,
     list_field,
     merge_guardrailed_scoped_messages,
     merge_returned_tools_into_request_tools,
@@ -720,6 +721,12 @@ class AnthropicMessagesHandler(BaseTranslation):
                         *anthropic_tools,
                     ]
                 )
+                if not scan_only_tool_results:
+                    data_dict: Final[dict[str, object]] = cast(dict[str, object], data)  # cast-ok: request dict
+                    retained_names: Final = frozenset(  # comprehension-ok: flattens tool names across tools
+                        name for t in list_field(data_dict, "tools") for name in anthropic_tool_names(t)
+                    )
+                    self._strip_disallowed_tool_additions(data_dict, retained_names)
 
             guardrailed_structured_messages: Final = guardrailed_inputs.get("structured_messages")
             if (
@@ -1000,8 +1007,72 @@ class AnthropicMessagesHandler(BaseTranslation):
 
     def extract_request_tool_names(self, data: Mapping[str, object]) -> list[str]:
         """Extract every tool name in an Anthropic messages request: tools[].name, plus
-        tools[].function.name for OpenAI-format tools the bridge forwards verbatim."""
-        return [name for tool in list_field(data, "tools") for name in anthropic_tool_names(tool)]
+        tools[].function.name for OpenAI-format tools the bridge forwards verbatim,
+        as well as mid-conversation tool additions in messages."""
+        top_names: Final = [  # comprehension-ok: flattens tool names across tools
+            name for tool in list_field(data, "tools") for name in anthropic_tool_names(tool)
+        ]
+        messages: Final = list_field(data, "messages")
+        if not messages:
+            return top_names
+        extra_names: Final[list[str]] = []  # mutable-ok: accumulator
+        for m in messages:
+            m_map = as_str_mapping(m)
+            if m_map is not None:
+                for block in list_field(m_map, "content"):
+                    block_map = as_str_mapping(block)
+                    if block_map is not None and block_map.get("type") == "tool_addition":
+                        tool = extract_tool_from_addition_block(block_map)
+                        if tool is not None:
+                            for name in anthropic_tool_names(tool):
+                                if name not in top_names and name not in extra_names:
+                                    extra_names.append(name)
+        return [*top_names, *extra_names]
+
+    @staticmethod
+    def _is_disallowed_addition_block(block: object, retained_names: frozenset[str]) -> bool:
+        block_map: Final = as_str_mapping(block)
+        if block_map is None or block_map.get("type") != "tool_addition":
+            return False
+        tool: Final = extract_tool_from_addition_block(block_map)
+        if tool is None:
+            return True
+        tool_names: Final = anthropic_tool_names(tool)
+        if not tool_names:
+            return True
+        return any(name not in retained_names for name in tool_names)
+
+    @classmethod
+    def _strip_disallowed_tool_additions(cls, data: Mapping[str, object], retained_names: frozenset[str]) -> None:
+        if not isinstance(data, dict):
+            return
+        messages_val: Final = data.get("messages")
+        if not isinstance(messages_val, list):
+            return
+        messages: Final = cast(Sequence[object], messages_val)  # cast-ok: messages list
+        cleaned_messages: Final[list[object]] = []  # mutable-ok: accumulator
+        for m in messages:
+            m_map = as_str_mapping(m)
+            if m_map is None:
+                cleaned_messages.append(m)
+                continue
+            content_val = m_map.get("content")
+            if not isinstance(content_val, list):
+                cleaned_messages.append(m)
+                continue
+            content: Sequence[object] = cast(Sequence[object], content_val)  # cast-ok: content list
+            had_disallowed_addition = any(cls._is_disallowed_addition_block(block, retained_names) for block in content)
+            if not had_disallowed_addition:
+                cleaned_messages.append(m)
+                continue
+            remaining_blocks: list[object] = [  # mutable-ok: accumulator
+                block for block in content if not cls._is_disallowed_addition_block(block, retained_names)
+            ]
+            if remaining_blocks:
+                new_m: dict[str, object] = dict(m_map)  # mutable-ok: message clone
+                new_m["content"] = remaining_blocks
+                cleaned_messages.append(new_m)
+        data["messages"] = cleaned_messages  # rebind-ok: update request in place
 
     @classmethod
     def _extract_input_text_and_images(

litellm/llms/anthropic/pass_through/adapters/transformation.py

@@ -8,7 +8,7 @@ from typing import TYPE_CHECKING, Any, Final, Literal, TypeAlias, TypeVar, cast
 from pydantic import JsonValue, TypeAdapter
 
 import litellm
-from litellm.litellm_core_utils.core_helpers import normalize_drop_params
+from litellm.litellm_core_utils.core_helpers import as_str_mapping, normalize_drop_params
 from litellm.litellm_core_utils.hidden_params import get_hidden_params
 from litellm.llms.anthropic.pass_through.convertible_blocks import tool_result_text_part
 from litellm.llms.anthropic.pass_through.utils import (
@@ -16,6 +16,10 @@ from litellm.llms.anthropic.pass_through.utils import (
     json_copy_or_original,
     prompt_cache_key_from_user_id,
 )
+from litellm.llms.base_llm.guardrail_translation.utils import (
+    extract_tool_from_addition_block,
+    list_field,
+)
 from litellm.responses.utils import auto_reasoning_summary
 
 # OpenAI has a 64-character limit for function/tool names
@@ -474,7 +478,10 @@ class LiteLLMAnthropicMessagesAdapter:
         preserve_midturn_system: bool = False,
     ) -> list[AllMessageValues]:
         new_messages: Final[list[AllMessageValues]] = []
-        replayable_messages: Final = strip_encrypted_reasoning_blocks_from_anthropic_messages(messages)
+        _, cleaned_input_messages = self._extract_and_apply_midturn_tool_changes(messages)
+        replayable_messages: Final = strip_encrypted_reasoning_blocks_from_anthropic_messages(
+            cast(Sequence[dict[str, object]], cleaned_input_messages)  # cast-ok: anthropic messages shape
+        )
         leading_count: Final = next(
             (i for i, m in enumerate(replayable_messages) if not is_system_role_message(m)),
             len(replayable_messages),
@@ -1230,6 +1237,102 @@ class LiteLLMAnthropicMessagesAdapter:
             if k not in translatable_params:  # pass remaining params as is
                 new_kwargs[k] = v
 
+    @staticmethod
+    def _adapter_tool_name(tool: object) -> str | None:
+        tool_map: Final = as_str_mapping(tool)
+        if tool_map is not None:
+            name_val: Final = tool_map.get("name")
+            if isinstance(name_val, str) and name_val:
+                return name_val
+        return None
+
+    def _extract_and_apply_midturn_tool_changes(
+        self,
+        messages: Sequence[Mapping[str, object] | AllAnthropicPassThroughMessageValues],
+        initial_tools: Sequence[object] | None = None,
+    ) -> tuple[tuple[AllAnthropicToolsValues, ...] | None, tuple[AllAnthropicPassThroughMessageValues, ...]]:
+        """
+        Extract and apply mid-conversation tool changes (tool_addition, tool_removal)
+        such as those sent by Claude Code under mid-conversation-tool-changes beta.
+
+        Returns:
+            Tuple of (active_tools, cleaned_messages)
+            - active_tools: Updated tools tuple with additions applied and removals removed,
+                            or None if no tools exist and none were added.
+            - cleaned_messages: Messages tuple with tool_addition and tool_removal blocks stripped,
+                                and carrier messages left without content dropped.
+        """
+        active_tools: tuple[AllAnthropicToolsValues, ...] = tuple(  # rebind-ok: tool updates
+            cast(  # cast-ok: initial tools
+                AllAnthropicToolsValues, t
+            )
+            for t in (initial_tools or ())
+        )
+        had_tool_changes: bool = False  # rebind-ok: state flag
+        cleaned_messages: Final[list[AllAnthropicPassThroughMessageValues]] = []  # mutable-ok: accumulator
+
+        for m in messages:
+            m_map = as_str_mapping(m)
+            if m_map is None:
+                cleaned_messages.append(cast(AllAnthropicPassThroughMessageValues, m))  # cast-ok: msg
+                continue
+            content = m_map.get("content")
+            if not isinstance(content, Sequence) or isinstance(content, (str, bytes)):
+                msg_val = cast(AllAnthropicPassThroughMessageValues, m)  # cast-ok: msg
+                cleaned_messages.append(msg_val)
+                continue
+
+            content_seq: Sequence[object] = cast(Sequence[object], content)  # cast-ok: content blocks
+            remaining_blocks: list[object] = []  # mutable-ok: accumulator
+            for block in content_seq:
+                block_map = as_str_mapping(block)
+                if block_map is None:
+                    remaining_blocks.append(block)
+                    continue
+                btype = block_map.get("type")
+                if btype == "tool_addition":
+                    had_tool_changes = True
+                    raw_tool = extract_tool_from_addition_block(block_map)
+                    if raw_tool is not None:
+                        tool_name = self._adapter_tool_name(raw_tool)
+                        if tool_name is not None and not any(
+                            self._adapter_tool_name(t) == tool_name for t in active_tools
+                        ):
+                            added_tool = cast(AllAnthropicToolsValues, dict(raw_tool))  # cast-ok: tool
+                            active_tools = (*active_tools, added_tool)
+                elif btype == "tool_removal":
+                    had_tool_changes = True
+                    tool_obj = block_map.get("tool")
+                    tool_map = as_str_mapping(tool_obj)
+                    rem_name = (
+                        block_map.get("tool_name")
+                        or block_map.get("name")
+                        or (tool_map.get("name") if tool_map is not None else None)
+                        or (tool_obj if isinstance(tool_obj, str) else None)
+                    )
+                    if rem_name:
+                        rem_name_str = str(rem_name)
+                        active_tools = tuple(t for t in active_tools if self._adapter_tool_name(t) != rem_name_str)
+                else:
+                    remaining_blocks.append(block)
+
+            if remaining_blocks:
+                new_m: dict[str, object] = dict(m_map)  # mutable-ok: message clone
+                new_m["content"] = remaining_blocks
+                new_msg = cast(AllAnthropicPassThroughMessageValues, new_m)  # cast-ok: msg
+                cleaned_messages.append(new_msg)
+            elif not had_tool_changes:
+                clean_msg = cast(AllAnthropicPassThroughMessageValues, m)  # cast-ok: msg
+                cleaned_messages.append(clean_msg)
+
+        if not had_tool_changes and initial_tools is None:
+            return None, tuple(cleaned_messages)
+
+        return (
+            active_tools if active_tools else (() if initial_tools is not None or had_tool_changes else None),
+            tuple(cleaned_messages),
+        )
+
     def translate_anthropic_to_openai(
         self,
         anthropic_message_request: AnthropicMessagesRequest,
@@ -1246,8 +1349,6 @@ class LiteLLMAnthropicMessagesAdapter:
             - tool_name_mapping maps truncated tool names back to original names
               for tools that exceeded OpenAI's 64-char limit
         """
-        # Debug: Processing Anthropic message request
-        new_messages: list[AllMessageValues] = []
         tool_name_mapping: dict[str, str] = {}
 
         ## CONVERT ANTHROPIC MESSAGES TO OPENAI
@@ -1255,14 +1356,32 @@ class LiteLLMAnthropicMessagesAdapter:
             list[AllAnthropicPassThroughMessageValues],
             anthropic_message_request["messages"],
         )
-        new_messages = self.translate_anthropic_messages_to_openai(
+        request_dict: Final[dict[str, object]] = dict(anthropic_message_request)  # mutable-ok: clone
+        initial_tools_val: Final = list_field(request_dict, "tools") if "tools" in request_dict else None
+        (
+            active_tools,
+            cleaned_messages,
+        ) = self._extract_and_apply_midturn_tool_changes(
             messages=messages_list,
+            initial_tools=initial_tools_val,
+        )
+        if active_tools is not None:
+            if active_tools:
+                request_dict["tools"] = list(active_tools)
+            else:
+                request_dict.pop("tools", None)
+        request_for_translation: Final[AnthropicMessagesRequest] = cast(  # cast-ok: anthropic request type
+            AnthropicMessagesRequest, request_dict
+        )
+
+        new_messages: Final = self.translate_anthropic_messages_to_openai(
+            messages=list(cleaned_messages),
             model=anthropic_message_request.get("model"),
             custom_llm_provider=custom_llm_provider,
             preserve_midturn_system=preserve_midturn_system,
         )
         ## ADD SYSTEM MESSAGE TO MESSAGES
-        self._add_system_message_to_messages(new_messages, anthropic_message_request)
+        self._add_system_message_to_messages(new_messages, request_for_translation)
 
         new_kwargs: Final[ChatCompletionRequest] = {
             "model": anthropic_message_request["model"],
@@ -1281,7 +1400,7 @@ class LiteLLMAnthropicMessagesAdapter:
         )
         ## CONVERT TOOLS
         tool_name_mapping = self._translate_tools_to_openai(
-            anthropic_message_request=anthropic_message_request,
+            anthropic_message_request=request_for_translation,
             new_kwargs=new_kwargs,
         )
         ## CONVERT THINKING

litellm/llms/base_llm/guardrail_translation/utils.py

@@ -6,6 +6,7 @@ from typing import Final, TypeVar, cast  # noqa: TID251  # a rebuilt chat row ha
 
 from pydantic import BaseModel, ConfigDict, TypeAdapter, ValidationError
 
+from litellm.litellm_core_utils.core_helpers import as_str_mapping
 from litellm.types.llms.anthropic_messages.anthropic_response import AnthropicUsage
 from litellm.types.llms.openai import AllMessageValues, ResponseAPIUsage
 
@@ -321,6 +322,27 @@ def anthropic_tool_name(tool: object) -> str | None:
     return names[0] if names else None
 
 
+def extract_tool_from_addition_block(block: object) -> Mapping[str, object] | None:
+    """Extract raw tool dict from an Anthropic tool_addition block."""
+    mapping: Final = as_str_mapping(block)
+    if mapping is None:
+        return None
+    tool_data: Final = as_str_mapping(mapping.get("tool"))
+    if tool_data is not None:
+        if (
+            tool_data.get("type") == "tool_definition"
+            and "definition" in tool_data
+            and (definition := as_str_mapping(tool_data.get("definition"))) is not None
+        ):
+            return definition
+        return tool_data
+    if "definition" in mapping and (definition := as_str_mapping(mapping.get("definition"))) is not None:
+        return definition
+    if (tool_def := as_str_mapping(mapping.get("tool_definition"))) is not None:
+        return tool_def
+    return None
+
+
 def merge_returned_tools_into_request_tools(
     request_tools: Sequence[ToolT] | None,
     returned_tools: Sequence[ToolT],

tests/unit/llms/anthropic/pass_through/adapters/test_anthropic_experimental_pass_through_adapters_transformation.py

@@ -12,7 +12,6 @@ import respx
 import litellm
 
 
-
 from litellm.litellm_core_utils.prompt_templates.common_utils import (
     TOOL_RESULT_IMAGE_PLACEHOLDER,
     encrypted_reasoning_signature,
@@ -66,10 +65,17 @@ def test_translate_openai_response_to_anthropic_empty_choices() -> None:
     assert result["usage"]["input_tokens"] == 10
 
 
-@pytest.mark.parametrize("text,count,expected_stop", [
-    ("", 1, "compaction"), (None, 1, "compaction"), ("Answer", 1, "max_tokens"),
-    (" ", 1, "max_tokens"), ("", 2, "max_tokens"), ("", 0, "max_tokens"),
-])
+@pytest.mark.parametrize(
+    "text,count,expected_stop",
+    [
+        ("", 1, "compaction"),
+        (None, 1, "compaction"),
+        ("Answer", 1, "max_tokens"),
+        (" ", 1, "max_tokens"),
+        ("", 2, "max_tokens"),
+        ("", 0, "max_tokens"),
+    ],
+)
 def test_native_compaction_response_roundtrip(text: str | None, count: int, expected_stop: str) -> None:
     block: Final = {"type": "compaction", "content": "Exact summary", "signature": "opaque-signature"}
     message: Final = Message(content=text, provider_specific_fields={"compaction_blocks": [block] * count})
@@ -178,9 +184,7 @@ def test_translate_streaming_openai_chunk_to_anthropic_content_block():
                 tool_calls=[
                     ChatCompletionDeltaToolCall(
                         id="call_d581d130-e234-4315-94e8-27e7ff7c4e55",
-                        function=Function(
-                            arguments='{"location": "Boston"}', name="get_weather"
-                        ),
+                        function=Function(arguments='{"location": "Boston"}', name="get_weather"),
                         type="function",
                         index=0,
                     )
@@ -224,9 +228,7 @@ def test_translate_streaming_openai_chunk_strips_gemini_thought_from_tool_call_i
                 tool_calls=[
                     ChatCompletionDeltaToolCall(
                         id=combined,
-                        function=Function(
-                            arguments='{"a": 17, "b": 25}', name="add_numbers"
-                        ),
+                        function=Function(arguments='{"a": 17, "b": 25}', name="add_numbers"),
                         type="function",
                         index=0,
                     )
@@ -463,10 +465,7 @@ def test_translate_anthropic_messages_to_openai_thinking_blocks():
     assert "thinking_blocks" in result[1]
     assert len(result[1]["thinking_blocks"]) == 2
     assert result[1]["thinking_blocks"][0]["type"] == "thinking"
-    assert (
-        result[1]["thinking_blocks"][0]["thinking"]
-        == "I will call the get_weather tool."
-    )
+    assert result[1]["thinking_blocks"][0]["thinking"] == "I will call the get_weather tool."
     assert result[1]["thinking_blocks"][0]["signature"] == "sigsig"
     assert result[1]["thinking_blocks"][1]["type"] == "redacted_thinking"
     assert result[1]["thinking_blocks"][1]["data"] == "REDACTED"
@@ -606,9 +605,7 @@ def test_translate_anthropic_messages_to_openai_tool_message_placement():
 
     assert tool_message_idx is not None, "Tool message not found"
     assert user_message_idx is not None, "User message not found"
-    assert (
-        tool_message_idx < user_message_idx
-    ), "Tool message should be placed before user message"
+    assert tool_message_idx < user_message_idx, "Tool message should be placed before user message"
 
 
 @pytest.mark.parametrize(
@@ -1074,9 +1071,7 @@ def test_translate_anthropic_to_openai_skips_prompt_cache_key_when_provider_lack
 
 
 def test_translate_anthropic_to_openai_skips_prompt_cache_key_for_chained_litellm_proxy():
-    assert "prompt_cache_key" in litellm.get_supported_openai_params(
-        model="xai", custom_llm_provider="litellm_proxy"
-    )
+    assert "prompt_cache_key" in litellm.get_supported_openai_params(model="xai", custom_llm_provider="litellm_proxy")
     openai_request = _translate_with_metadata("litellm_proxy/xai", {"user_id": CLAUDE_CODE_USER_ID}, "litellm_proxy")
     assert openai_request["user"] == CLAUDE_CODE_USER_ID
     assert "prompt_cache_key" not in openai_request
@@ -1121,7 +1116,8 @@ def test_translate_openai_content_to_anthropic_empty_function_arguments():
                         id="call_empty_args",
                         type="function",
                         function=Function(
-                            name="test_function", arguments=""  # empty arguments string
+                            name="test_function",
+                            arguments="",  # empty arguments string
                         ),
                     )
                 ],
@@ -1136,9 +1132,7 @@ def test_translate_openai_content_to_anthropic_empty_function_arguments():
     assert result[0]["type"] == "tool_use"
     assert result[0]["id"] == "call_empty_args"
     assert result[0]["name"] == "test_function"
-    assert (
-        result[0]["input"] == {}
-    ), "Empty function arguments should result in empty dict"
+    assert result[0]["input"] == {}, "Empty function arguments should result in empty dict"
     assert "provider_specific_fields" not in result[0]
 
 
@@ -1262,9 +1256,7 @@ def test_translate_openai_response_to_anthropic_text_and_tool_calls():
                         ChatCompletionAssistantToolCall(
                             id="call_tool_combo",
                             type="function",
-                            function=Function(
-                                name="get_weather", arguments='{"location": "Paris"}'
-                            ),
+                            function=Function(name="get_weather", arguments='{"location": "Paris"}'),
                         )
                     ],
                 ),
@@ -1274,9 +1266,7 @@ def test_translate_openai_response_to_anthropic_text_and_tool_calls():
     )
 
     adapter = LiteLLMAnthropicMessagesAdapter()
-    anthropic_response = adapter.translate_openai_response_to_anthropic(
-        response=openai_response
-    )
+    anthropic_response = adapter.translate_openai_response_to_anthropic(response=openai_response)
 
     anthropic_content = anthropic_response.get("content")
     assert anthropic_content is not None
@@ -1317,9 +1307,7 @@ def test_translate_streaming_openai_chunk_to_anthropic_with_partial_json():
     (
         type_of_content,
         content_block_delta,
-    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(
-        choices=choices
-    )
+    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(choices=choices)
 
     print("Type of content:", type_of_content)
     print("Content block delta:", content_block_delta)
@@ -1428,9 +1416,7 @@ def test_translate_streaming_openai_chunk_to_anthropic_thinking_delta():
     (
         type_of_content,
         content_block_delta,
-    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(
-        choices=choices
-    )
+    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(choices=choices)
 
     assert type_of_content == "thinking_delta"
     assert content_block_delta["type"] == "thinking_delta"
@@ -1473,9 +1459,7 @@ def test_translate_streaming_openai_chunk_to_anthropic_with_thinking():
     (
         type_of_content,
         content_block_delta,
-    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(
-        choices=choices
-    )
+    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(choices=choices)
 
     assert type_of_content == "signature_delta"
     assert content_block_delta["type"] == "signature_delta"
@@ -1579,9 +1563,7 @@ def test_translate_anthropic_messages_to_openai_user_message_with_base64_image()
     # Check image content
     assert result[0]["content"][1]["type"] == "image_url"
     assert "image_url" in result[0]["content"][1]
-    assert result[0]["content"][1]["image_url"]["url"].startswith(
-        "data:image/png;base64,"
-    )
+    assert result[0]["content"][1]["image_url"]["url"].startswith("data:image/png;base64,")
     assert (
         "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mNk+M9QDwADhgGAWjR9awAAAABJRU5ErkJggg=="
         in result[0]["content"][1]["image_url"]["url"]
@@ -1619,18 +1601,14 @@ def test_translate_anthropic_messages_to_openai_user_message_with_url_image():
     # Check image content
     assert result[0]["content"][1]["type"] == "image_url"
     assert "image_url" in result[0]["content"][1]
-    assert (
-        result[0]["content"][1]["image_url"]["url"] == "https://example.com/forest.jpg"
-    )
+    assert result[0]["content"][1]["image_url"]["url"] == "https://example.com/forest.jpg"
 
 
 def test_translate_anthropic_messages_to_openai_tool_result_with_base64_image():
     """Test that base64 images in tool results are correctly translated to OpenAI format."""
 
     anthropic_messages = [
-        AnthropicMessagesUserMessageParam(
-            role="user", content=[{"type": "text", "text": "Take a screenshot"}]
-        ),
+        AnthropicMessagesUserMessageParam(role="user", content=[{"type": "text", "text": "Take a screenshot"}]),
         AnthopicMessagesAssistantMessageParam(
             role="assistant",
             content=[
@@ -1782,9 +1760,7 @@ def test_translate_anthropic_messages_to_openai_mixed_content_with_image():
 
     # Check first image (base64)
     assert result[0]["content"][1]["type"] == "image_url"
-    assert result[0]["content"][1]["image_url"]["url"].startswith(
-        "data:image/png;base64,"
-    )
+    assert result[0]["content"][1]["image_url"]["url"].startswith("data:image/png;base64,")
 
     # Check middle text
     assert result[0]["content"][2]["type"] == "text"
@@ -1792,9 +1768,7 @@ def test_translate_anthropic_messages_to_openai_mixed_content_with_image():
 
     # Check second image (URL)
     assert result[0]["content"][3]["type"] == "image_url"
-    assert (
-        result[0]["content"][3]["image_url"]["url"] == "https://example.com/image2.jpg"
-    )
+    assert result[0]["content"][3]["image_url"]["url"] == "https://example.com/image2.jpg"
 
     # Check final text
     assert result[0]["content"][4]["type"] == "text"
@@ -1840,10 +1814,7 @@ def test_translate_anthropic_messages_to_openai_tool_use_with_signature():
     assert tool_call["id"] == "call_386f67af31f9415781bc35071405"
     assert "function" in tool_call
     assert "provider_specific_fields" in tool_call["function"]
-    assert (
-        tool_call["function"]["provider_specific_fields"]["thought_signature"]
-        == test_signature
-    )
+    assert tool_call["function"]["provider_specific_fields"]["thought_signature"] == test_signature
 
 
 def test_translate_anthropic_messages_to_openai_tool_result_with_multiple_content_items():
@@ -1901,9 +1872,7 @@ def test_translate_anthropic_messages_to_openai_tool_result_with_multiple_conten
     result = adapter.translate_anthropic_messages_to_openai(messages=anthropic_messages)
 
     # Count how many tool messages have the same tool_call_id
-    tool_messages = [
-        msg for msg in result if isinstance(msg, dict) and msg.get("role") == "tool"
-    ]
+    tool_messages = [msg for msg in result if isinstance(msg, dict) and msg.get("role") == "tool"]
     tool_call_ids = [msg.get("tool_call_id") for msg in tool_messages]
 
     # The critical assertion: each tool_call_id should appear only ONCE
@@ -1919,12 +1888,8 @@ def test_translate_anthropic_messages_to_openai_tool_result_with_multiple_conten
     # The content should be a list with all items combined
     tool_message = tool_messages[0]
     assert tool_message["tool_call_id"] == "toolu_016hYHBkTf4JDF3p22UoYk5C"
-    assert isinstance(
-        tool_message["content"], list
-    ), "Multiple content items should be combined into a list"
-    assert (
-        len(tool_message["content"]) == 3
-    ), f"Expected 3 content items, got {len(tool_message['content'])}"
+    assert isinstance(tool_message["content"], list), "Multiple content items should be combined into a list"
+    assert len(tool_message["content"]) == 3, f"Expected 3 content items, got {len(tool_message['content'])}"
 
     # Verify content types
     assert tool_message["content"][0]["type"] == "text"
@@ -1973,17 +1938,14 @@ def test_translate_anthropic_messages_to_openai_tool_result_single_item_backward
     adapter = LiteLLMAnthropicMessagesAdapter()
     result = adapter.translate_anthropic_messages_to_openai(messages=anthropic_messages)
 
-    tool_messages = [
-        msg for msg in result if isinstance(msg, dict) and msg.get("role") == "tool"
-    ]
+    tool_messages = [msg for msg in result if isinstance(msg, dict) and msg.get("role") == "tool"]
 
     assert len(tool_messages) == 1
     tool_message = tool_messages[0]
 
     # Single item should be a string for backward compatibility
     assert isinstance(tool_message["content"], str), (
-        f"Single content item should be a string for backward compatibility, "
-        f"got {type(tool_message['content'])}"
+        f"Single content item should be a string for backward compatibility, got {type(tool_message['content'])}"
     )
     assert tool_message["content"] == "72°F and sunny"
 
@@ -2087,15 +2049,12 @@ def test_streaming_chunk_with_text_and_empty_tool_calls_returns_text_delta():
 # ============================================================================
 
 # Model constant for cache control tests
-CACHE_CONTROL_BEDROCK_CONVERSE_MODEL = (
-    "bedrock/converse/global.anthropic.claude-opus-4-5-20251101-v1:0"
-)
+CACHE_CONTROL_BEDROCK_CONVERSE_MODEL = "bedrock/converse/global.anthropic.claude-opus-4-5-20251101-v1:0"
 CACHE_CONTROL_NON_ANTHROPIC_MODEL = "gpt-4"
 # Bedrock Application Inference Profile ARN: the string contains neither
 # "anthropic" nor "claude", so the model can only be recognized via its ARN shape
 CACHE_CONTROL_BEDROCK_ARN_MODEL = (
-    "bedrock/converse/arn:aws:bedrock:us-east-1:123456789012:"
-    "application-inference-profile/abcdef123456"
+    "bedrock/converse/arn:aws:bedrock:us-east-1:123456789012:application-inference-profile/abcdef123456"
 )
 
 
@@ -2111,9 +2070,7 @@ def test_should_add_cache_control_for_anthropic_model():
         "vertex_ai/claude-3-sonnet@20240229",
     ]:
         target = {}
-        adapter._add_cache_control_if_applicable(
-            {"cache_control": cache_control}, target, model
-        )
+        adapter._add_cache_control_if_applicable({"cache_control": cache_control}, target, model)
         assert "cache_control" in target
         assert target["cache_control"] == cache_control
 
@@ -2128,9 +2085,7 @@ def test_should_not_add_cache_control_for_non_anthropic_model():
         "openai/gpt-4-turbo",
     ]:
         target = {}
-        adapter._add_cache_control_if_applicable(
-            {"cache_control": cache_control}, target, model
-        )
+        adapter._add_cache_control_if_applicable({"cache_control": cache_control}, target, model)
         assert "cache_control" not in target
 
 
@@ -2145,9 +2100,7 @@ def test_should_add_cache_control_for_gemini_model():
         "vertex_ai/gemini-2.5-pro",
     ]:
         target = {}
-        adapter._add_cache_control_if_applicable(
-            {"cache_control": cache_control}, target, model
-        )
+        adapter._add_cache_control_if_applicable({"cache_control": cache_control}, target, model)
         assert target.get("cache_control") == cache_control
 
 
@@ -2185,9 +2138,7 @@ def test_should_not_add_cache_control_when_none():
         {},
     ]:
         target = {}
-        adapter._add_cache_control_if_applicable(
-            source, target, CACHE_CONTROL_BEDROCK_CONVERSE_MODEL
-        )
+        adapter._add_cache_control_if_applicable(source, target, CACHE_CONTROL_BEDROCK_CONVERSE_MODEL)
         assert "cache_control" not in target
 
 
@@ -2198,9 +2149,7 @@ def test_should_not_add_cache_control_when_model_none():
 
     for model in [None, ""]:
         target = {}
-        adapter._add_cache_control_if_applicable(
-            {"cache_control": cache_control}, target, model
-        )
+        adapter._add_cache_control_if_applicable({"cache_control": cache_control}, target, model)
         assert "cache_control" not in target
 
 
@@ -2306,12 +2255,7 @@ def test_cache_control_fix_does_not_broaden_claude_detection():
     make is_anthropic_claude_model treat ARN profiles as Claude, which would route
     thinking params through unmodified and break non-Claude Bedrock profiles.
     """
-    assert (
-        LiteLLMAnthropicMessagesAdapter.is_anthropic_claude_model(
-            CACHE_CONTROL_BEDROCK_ARN_MODEL
-        )
-        is False
-    )
+    assert LiteLLMAnthropicMessagesAdapter.is_anthropic_claude_model(CACHE_CONTROL_BEDROCK_ARN_MODEL) is False
 
 
 def test_thinking_preserved_for_bedrock_arn_inference_profile():
@@ -2940,9 +2884,7 @@ def test_translate_streaming_openai_chunk_to_anthropic_reasoning_content_without
     (
         type_of_content,
         content_block_delta,
-    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(
-        choices=choices
-    )
+    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(choices=choices)
 
     assert type_of_content == "thinking_delta"
     assert content_block_delta["type"] == "thinking_delta"
@@ -2974,9 +2916,7 @@ def test_translate_openai_response_to_anthropic_with_reasoning_content_only():
     )
 
     adapter = LiteLLMAnthropicMessagesAdapter()
-    anthropic_response = adapter.translate_openai_response_to_anthropic(
-        response=openai_response
-    )
+    anthropic_response = adapter.translate_openai_response_to_anthropic(response=openai_response)
 
     anthropic_content = anthropic_response.get("content")
     assert anthropic_content is not None
@@ -2989,9 +2929,7 @@ def test_translate_openai_response_to_anthropic_with_reasoning_content_only():
 
     # Second block should be text
     assert anthropic_content[1]["type"] == "text"
-    assert (
-        anthropic_content[1]["text"] == 'There are **3** "r"s in the word strawberry.'
-    )
+    assert anthropic_content[1]["text"] == 'There are **3** "r"s in the word strawberry.'
 
     assert anthropic_response.get("stop_reason") == "end_turn"
 
@@ -3043,9 +2981,7 @@ def test_truncate_tool_name_deterministic():
 def test_truncate_tool_name_avoids_collisions():
     """Similar long names should produce different truncated names."""
     name1 = "process_user_data_with_validation_and_error_handling_for_production_environment"
-    name2 = (
-        "process_user_data_with_validation_and_error_handling_for_staging_environment"
-    )
+    name2 = "process_user_data_with_validation_and_error_handling_for_staging_environment"
 
     result1 = truncate_tool_name(name1)
     result2 = truncate_tool_name(name2)
@@ -3065,9 +3001,7 @@ def test_create_tool_name_mapping_no_long_names():
 
 def test_create_tool_name_mapping_with_long_names():
     """Mapping should contain entries for truncated names."""
-    long_name = (
-        "a_very_long_tool_name_that_exceeds_the_64_character_limit_imposed_by_openai"
-    )
+    long_name = "a_very_long_tool_name_that_exceeds_the_64_character_limit_imposed_by_openai"
     tools = [
         {"name": "short_name"},
         {"name": long_name},
@@ -3092,9 +3026,7 @@ def test_translate_anthropic_tools_with_long_names():
     ]
 
     adapter = LiteLLMAnthropicMessagesAdapter()
-    result, tool_name_mapping = adapter.translate_anthropic_tools_to_openai(
-        tools=tools, model="gpt-4"
-    )
+    result, tool_name_mapping = adapter.translate_anthropic_tools_to_openai(tools=tools, model="gpt-4")
 
     assert len(result) == 1
     # The tool name should be truncated
@@ -3116,9 +3048,7 @@ def test_translate_anthropic_tools_mixed_names():
     ]
 
     adapter = LiteLLMAnthropicMessagesAdapter()
-    result, tool_name_mapping = adapter.translate_anthropic_tools_to_openai(
-        tools=tools, model="gpt-4"
-    )
+    result, tool_name_mapping = adapter.translate_anthropic_tools_to_openai(tools=tools, model="gpt-4")
 
     assert len(result) == 2
     # Short name unchanged
@@ -3132,9 +3062,7 @@ def test_translate_anthropic_tools_mixed_names():
 
 def test_translate_openai_response_restores_tool_names():
     """Tool names in responses should be restored to original."""
-    original_name = (
-        "a_very_long_tool_name_that_needs_truncation_for_openai_api_compatibility"
-    )
+    original_name = "a_very_long_tool_name_that_needs_truncation_for_openai_api_compatibility"
     truncated_name = truncate_tool_name(original_name)
     tool_name_mapping = {truncated_name: original_name}
 
@@ -3166,9 +3094,7 @@ def test_translate_openai_response_restores_tool_names():
     )
 
     adapter = LiteLLMAnthropicMessagesAdapter()
-    result = adapter.translate_openai_response_to_anthropic(
-        response=response, tool_name_mapping=tool_name_mapping
-    )
+    result = adapter.translate_openai_response_to_anthropic(response=response, tool_name_mapping=tool_name_mapping)
 
     # Find the tool_use block in the response
     tool_use_blocks = [c for c in result["content"] if c.get("type") == "tool_use"]
@@ -3589,9 +3515,7 @@ def test_translate_streaming_openai_response_to_anthropic_cache_tokens_with_appl
     assert message_delta["usage"]["output_tokens"] == 50
     assert message_delta["usage"]["cache_read_input_tokens"] == 30
     assert message_delta["usage"]["cache_creation_input_tokens"] == 20
-    assert message_delta["context_management"]["applied_edits"][0]["type"] == (
-        "compact_20260112"
-    )
+    assert message_delta["context_management"]["applied_edits"][0]["type"] == ("compact_20260112")
 
 
 # =====================================================================
@@ -3640,9 +3564,7 @@ def test_translate_anthropic_client_web_search_preserves_schema_and_choice(schem
     translated, _ = LiteLLMAnthropicMessagesAdapter().translate_anthropic_to_openai(request)
 
     assert "web_search_options" not in translated
-    assert translated["tools"] == [
-        {"type": "function", "function": {"name": "web_search", "parameters": schema}}
-    ]
+    assert translated["tools"] == [{"type": "function", "function": {"name": "web_search", "parameters": schema}}]
     assert translated["tool_choice"] == {"type": "function", "function": {"name": "web_search"}}
 
 
@@ -3787,15 +3709,8 @@ class TestTranslateAnthropicOutputFormatToOpenAI:
         assert schema["required"] == ["user"]
         assert schema["properties"]["user"]["additionalProperties"] is False
         assert schema["properties"]["user"]["required"] == ["name", "address"]
-        assert (
-            schema["properties"]["user"]["properties"]["address"][
-                "additionalProperties"
-            ]
-            is False
-        )
-        assert schema["properties"]["user"]["properties"]["address"]["required"] == [
-            "city"
-        ]
+        assert schema["properties"]["user"]["properties"]["address"]["additionalProperties"] is False
+        assert schema["properties"]["user"]["properties"]["address"]["required"] == ["city"]
 
     def test_array_items_object_adds_additional_properties_false(self):
         output_format = {
@@ -3870,19 +3785,9 @@ class TestTranslateAnthropicOutputFormatToOpenAI:
         assert sorted(schema["required"]) == ["age", "email", "name"]
 
     def test_invalid_output_format_returns_none(self):
-        assert (
-            self.adapter.translate_anthropic_output_format_to_openai("invalid") is None
-        )
-        assert (
-            self.adapter.translate_anthropic_output_format_to_openai({"type": "text"})
-            is None
-        )
-        assert (
-            self.adapter.translate_anthropic_output_format_to_openai(
-                {"type": "json_schema"}
-            )
-            is None
-        )
+        assert self.adapter.translate_anthropic_output_format_to_openai("invalid") is None
+        assert self.adapter.translate_anthropic_output_format_to_openai({"type": "text"}) is None
+        assert self.adapter.translate_anthropic_output_format_to_openai({"type": "json_schema"}) is None
 
 
 class TestAnthropicStreamWrapperToolArgs:
@@ -4086,9 +3991,7 @@ def test_translate_openai_response_to_anthropic_with_polyfill_compaction_block()
     )
     response = _make_simple_openai_response(text="Hello after compaction.")
     adapter = LiteLLMAnthropicMessagesAdapter()
-    result = adapter.translate_openai_response_to_anthropic(
-        response=response, polyfill_result=polyfill
-    )
+    result = adapter.translate_openai_response_to_anthropic(response=response, polyfill_result=polyfill)
 
     content = result.get("content")
     assert content is not None
@@ -4120,9 +4023,7 @@ def test_translate_openai_response_to_anthropic_with_polyfill_iterations_usage()
     )
     response = _make_simple_openai_response(prompt_tokens=100, completion_tokens=30)
     adapter = LiteLLMAnthropicMessagesAdapter()
-    result = adapter.translate_openai_response_to_anthropic(
-        response=response, polyfill_result=polyfill
-    )
+    result = adapter.translate_openai_response_to_anthropic(response=response, polyfill_result=polyfill)
 
     usage = result.get("usage")
     assert usage is not None
@@ -4177,13 +4078,9 @@ def test_translate_openai_response_to_anthropic_with_polyfill_both_compaction_an
             {"type": "compaction", "input_tokens": 300, "output_tokens": 75},
         ],
     )
-    response = _make_simple_openai_response(
-        text="After compaction.", prompt_tokens=120, completion_tokens=40
-    )
+    response = _make_simple_openai_response(text="After compaction.", prompt_tokens=120, completion_tokens=40)
     adapter = LiteLLMAnthropicMessagesAdapter()
-    result = adapter.translate_openai_response_to_anthropic(
-        response=response, polyfill_result=polyfill
-    )
+    result = adapter.translate_openai_response_to_anthropic(response=response, polyfill_result=polyfill)
 
     # compaction block must come first
     content = result.get("content")
@@ -4285,7 +4182,9 @@ def test_translate_anthropic_tools_to_openai_omits_unset_strict():
     assert function["parameters"]["required"] == ["query"]
 
 
-TOOL_RESULT_IMAGE_B64 = "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mNk+M9QDwADhgGAWjR9awAAAABJRU5ErkJggg=="
+TOOL_RESULT_IMAGE_B64 = (
+    "iVBORw0KGgoAAAANSUhEUgAAAAEAAAABCAYAAAAfFcSJAAAADUlEQVR42mNk+M9QDwADhgGAWjR9awAAAABJRU5ErkJggg=="
+)
 TOOL_RESULT_IMAGE_URL = "https://example.com/screenshot.png"
 
 
@@ -4293,8 +4192,7 @@ def _anthropic_tool_use_turn(*tool_use_ids):
     return AnthopicMessagesAssistantMessageParam(
         role="assistant",
         content=[
-            {"type": "tool_use", "id": tid, "name": "read_file", "input": {"path": "img.png"}}
-            for tid in tool_use_ids
+            {"type": "tool_use", "id": tid, "name": "read_file", "input": {"path": "img.png"}} for tid in tool_use_ids
         ],
     )
 
@@ -4414,9 +4312,7 @@ def test_tool_result_parallel_tool_calls_keep_tool_message_adjacency():
     result = _run_chat_completions_pipeline(
         [
             _anthropic_tool_use_turn("toolu_01", "toolu_02"),
-            _anthropic_tool_result_turn(
-                {"toolu_01": [_base64_image_block()], "toolu_02": [_url_image_block()]}
-            ),
+            _anthropic_tool_result_turn({"toolu_01": [_base64_image_block()], "toolu_02": [_url_image_block()]}),
         ]
     )
 
@@ -4607,10 +4503,7 @@ def test_tool_result_text_and_document_reach_bedrock_converse_tool_result():
     )
 
     tool_results = [
-        block["toolResult"]
-        for message in converse_messages
-        for block in message["content"]
-        if "toolResult" in block
+        block["toolResult"] for message in converse_messages for block in message["content"] if "toolResult" in block
     ]
     assert len(tool_results) == 1
     documents = [part["document"] for part in tool_results[0]["content"] if "document" in part]
@@ -4669,7 +4562,9 @@ def test_translate_anthropic_to_openai_without_prompt_cache_breakpoint_adds_noth
 def test_translate_anthropic_messages_to_openai_carries_midturn_system_prompt_cache_breakpoint():
     explicit = {"mode": "explicit"}
     result = LiteLLMAnthropicMessagesAdapter().translate_anthropic_messages_to_openai(
-        messages=[{"role": "system", "content": [{"type": "text", "text": "fix", "prompt_cache_breakpoint": explicit}]}],
+        messages=[
+            {"role": "system", "content": [{"type": "text", "text": "fix", "prompt_cache_breakpoint": explicit}]}
+        ],
         model="gpt-5.6",
     )
     assert result == [
@@ -5419,3 +5314,322 @@ async def test_chat_bridge_tool_result_text_block_without_text_reaches_the_model
             ],
         }
     ]
+
+
+def test_translate_anthropic_to_openai_midturn_tool_addition():
+    """
+    Test that mid-conversation tool_addition blocks (such as Claude Code's mid-conversation-tool-changes)
+    are hoisted into the request's tools and stripped from the translated messages.
+    """
+    messages = [
+        {"role": "user", "content": "What is the weather in Dallas?"},
+        {
+            "role": "system",
+            "content": [
+                {"type": "text", "text": "A new tool is available."},
+                {
+                    "type": "tool_addition",
+                    "tool": {
+                        "type": "tool_definition",
+                        "definition": {
+                            "name": "get_weather",
+                            "description": "Get the weather for a city",
+                            "input_schema": {
+                                "type": "object",
+                                "properties": {"city": {"type": "string"}},
+                                "required": ["city"],
+                            },
+                        },
+                    },
+                },
+            ],
+        },
+    ]
+
+    adapter = LiteLLMAnthropicMessagesAdapter()
+    req = {"model": "openai/some-open-model", "messages": messages}
+    translated_req, _ = adapter.translate_anthropic_to_openai(req)
+
+    # Verify tool was added to tools
+    assert "tools" in translated_req
+    assert len(translated_req["tools"]) == 1
+    tool = translated_req["tools"][0]
+    assert tool["type"] == "function"
+    assert tool["function"]["name"] == "get_weather"
+    assert tool["function"]["description"] == "Get the weather for a city"
+    assert tool["function"]["parameters"]["properties"]["city"]["type"] == "string"
+
+    # Verify tool_addition was stripped and text preserved
+    assert len(translated_req["messages"]) == 2
+    assert "get_weather" not in json.dumps(translated_req["messages"])
+
+
+def test_translate_anthropic_to_openai_midturn_tool_addition_carrier_only():
+    """
+    Test that when a system message contains only tool_addition, the tool is added
+    and the carrier message is dropped so no empty operator note is sent.
+    """
+    messages = [
+        {"role": "user", "content": "Hello"},
+        {
+            "role": "system",
+            "content": [
+                {
+                    "type": "tool_addition",
+                    "tool": {
+                        "type": "tool_definition",
+                        "definition": {
+                            "name": "calc",
+                            "description": "Calculator",
+                            "input_schema": {"type": "object"},
+                        },
+                    },
+                }
+            ],
+        },
+        {"role": "user", "content": "Calculate 2+2"},
+    ]
+
+    adapter = LiteLLMAnthropicMessagesAdapter()
+    req = {"model": "openai/some-open-model", "messages": messages}
+    translated_req, _ = adapter.translate_anthropic_to_openai(req)
+
+    assert "tools" in translated_req
+    assert len(translated_req["tools"]) == 1
+    assert translated_req["tools"][0]["function"]["name"] == "calc"
+
+    # Carrier message should be dropped entirely
+    assert len(translated_req["messages"]) == 2
+    assert translated_req["messages"][0]["content"] == "Hello"
+    assert translated_req["messages"][1]["content"] == "Calculate 2+2"
+
+
+def test_translate_anthropic_to_openai_midturn_tool_removal():
+    """
+    Test that mid-conversation tool_removal drops the tool from the request.
+    """
+    messages = [
+        {"role": "user", "content": "Start"},
+        {"role": "system", "content": [{"type": "tool_removal", "tool_name": "calc"}]},
+    ]
+
+    adapter = LiteLLMAnthropicMessagesAdapter()
+    req = {
+        "model": "openai/some-open-model",
+        "messages": messages,
+        "tools": [
+            {"name": "calc", "input_schema": {}},
+            {"name": "search", "input_schema": {}},
+        ],
+    }
+    translated_req, _ = adapter.translate_anthropic_to_openai(req)
+
+    assert "tools" in translated_req
+    tool_names = [t["function"]["name"] for t in translated_req["tools"]]
+    assert tool_names == ["search"]
+
+
+def test_translate_anthropic_to_openai_midturn_tool_addition_deduplication():
+    """
+    Test that adding a tool that is already in top-level tools skips duplicate definition.
+    """
+    messages = [
+        {"role": "user", "content": "Hello"},
+        {
+            "role": "system",
+            "content": [
+                {
+                    "type": "tool_addition",
+                    "tool": {
+                        "name": "calc",
+                        "description": "Calculator",
+                        "input_schema": {"type": "object"},
+                    },
+                }
+            ],
+        },
+    ]
+
+    adapter = LiteLLMAnthropicMessagesAdapter()
+    req = {
+        "model": "openai/some-open-model",
+        "messages": messages,
+        "tools": [{"name": "calc", "input_schema": {}}],
+    }
+    translated_req, _ = adapter.translate_anthropic_to_openai(req)
+
+    assert len(translated_req["tools"]) == 1
+    assert translated_req["tools"][0]["function"]["name"] == "calc"
+
+
+def test_translate_anthropic_to_openai_midturn_tool_addition_and_removal_shapes():
+    """
+    Test alternative payload shapes for tool_addition and tool_removal.
+    """
+    adapter = LiteLLMAnthropicMessagesAdapter()
+
+    # 1. block with "definition" directly
+    req1 = {
+        "model": "openai/some-open-model",
+        "messages": [
+            {
+                "role": "system",
+                "content": [
+                    {
+                        "type": "tool_addition",
+                        "definition": {"name": "def_tool", "input_schema": {}},
+                    }
+                ],
+            }
+        ],
+    }
+    t_req1, _ = adapter.translate_anthropic_to_openai(req1)
+    assert any(t["function"]["name"] == "def_tool" for t in t_req1["tools"])
+
+    # 2. block with "tool_definition" directly
+    req2 = {
+        "model": "openai/some-open-model",
+        "messages": [
+            {
+                "role": "system",
+                "content": [
+                    {
+                        "type": "tool_addition",
+                        "tool_definition": {"name": "tool_def_tool", "input_schema": {}},
+                    }
+                ],
+            }
+        ],
+    }
+    t_req2, _ = adapter.translate_anthropic_to_openai(req2)
+    assert any(t["function"]["name"] == "tool_def_tool" for t in t_req2["tools"])
+
+    # 3. block with "tool" as dict directly
+    req3 = {
+        "model": "openai/some-open-model",
+        "messages": [
+            {
+                "role": "system",
+                "content": [
+                    {
+                        "type": "tool_addition",
+                        "tool": {"name": "raw_tool", "input_schema": {}},
+                    }
+                ],
+            }
+        ],
+    }
+    t_req3, _ = adapter.translate_anthropic_to_openai(req3)
+    assert any(t["function"]["name"] == "raw_tool" for t in t_req3["tools"])
+
+    # 4. removal variations: "name", "tool.name", "tool" as string
+    req4 = {
+        "model": "openai/some-open-model",
+        "tools": [
+            {"name": "rem1", "input_schema": {}},
+            {"name": "rem2", "input_schema": {}},
+            {"name": "rem3", "input_schema": {}},
+            {"name": "keep", "input_schema": {}},
+        ],
+        "messages": [
+            {
+                "role": "system",
+                "content": [
+                    {"type": "tool_removal", "name": "rem1"},
+                    {"type": "tool_removal", "tool": {"name": "rem2"}},
+                    {"type": "tool_removal", "tool": "rem3"},
+                ],
+            }
+        ],
+    }
+    t_req4, _ = adapter.translate_anthropic_to_openai(req4)
+    names = [t["function"]["name"] for t in t_req4["tools"]]
+    assert names == ["keep"]
+
+
+def test_extract_request_tool_names_includes_midturn_additions():
+    """
+    Test that AnthropicMessagesHandler.extract_request_tool_names discovers tools
+    defined inside mid-conversation tool_addition blocks so allowlists are enforced.
+    """
+    from litellm.llms.anthropic.chat.guardrail_translation.handler import (
+        AnthropicMessagesHandler,
+    )
+
+    handler = AnthropicMessagesHandler()
+    data = {
+        "model": "claude-3-5-sonnet-20241022",
+        "tools": [{"name": "allowed_tool", "input_schema": {}}],
+        "messages": [
+            {"role": "user", "content": "Hello"},
+            {
+                "role": "system",
+                "content": [
+                    {
+                        "type": "tool_addition",
+                        "tool": {
+                            "type": "tool_definition",
+                            "definition": {
+                                "name": "smuggled_tool",
+                                "input_schema": {},
+                            },
+                        },
+                    }
+                ],
+            },
+        ],
+    }
+
+    extracted_names = handler.extract_request_tool_names(data)
+    assert "allowed_tool" in extracted_names
+    assert "smuggled_tool" in extracted_names
+
+
+def test_strip_disallowed_tool_additions_when_guardrail_filters_tools():
+    """
+    Test that _strip_disallowed_tool_additions strips any tool_addition block
+    for tools that were removed by guardrails.
+    """
+    from litellm.llms.anthropic.chat.guardrail_translation.handler import (
+        AnthropicMessagesHandler,
+    )
+
+    handler = AnthropicMessagesHandler()
+    data = {
+        "model": "claude-3-5-sonnet-20241022",
+        "tools": [{"name": "allowed_tool", "input_schema": {}}],
+        "messages": [
+            {
+                "role": "user",
+                "content": [
+                    {"type": "text", "text": "Do something"},
+                    {
+                        "type": "tool_addition",
+                        "tool": {"name": "disallowed_tool", "input_schema": {}},
+                    },
+                ],
+            },
+            {
+                "role": "system",
+                "content": [
+                    {
+                        "type": "tool_addition",
+                        "tool": {"name": "allowed_tool", "input_schema": {}},
+                    }
+                ],
+            },
+        ],
+    }
+
+    retained_names = frozenset({"allowed_tool"})
+    handler._strip_disallowed_tool_additions(data, retained_names)
+
+    # Disallowed tool_addition was stripped from user message, but text remains
+    user_content = data["messages"][0]["content"]
+    assert len(user_content) == 1
+    assert user_content[0]["text"] == "Do something"
+
+    # Allowed tool_addition remains
+    sys_content = data["messages"][1]["content"]
+    assert len(sys_content) == 1
+    assert sys_content[0]["tool"]["name"] == "allowed_tool"