fix(anthropic): stop 500 on combined thinking+signature streaming chunk

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

@@ -1403,11 +1403,6 @@ def _translate_streaming_openai_chunk_to_anthropic_content_block(
                         assert isinstance(thinking, str)
                         assert isinstance(signature, str)
 
-                        if thinking and signature:
-                            raise ValueError(
-                                "Both `thinking` and `signature` in a single streaming chunk isn't supported."
-                            )
-
                         return "thinking", ChatCompletionThinkingBlock(
                             type="thinking", thinking=thinking, signature=signature
                         )
@@ -1463,17 +1458,14 @@ def _translate_streaming_openai_chunk_to_anthropic(
                 if choice.delta.reasoning_content is not None:
                     reasoning_content += choice.delta.reasoning_content
 
-        if reasoning_content and reasoning_signature:
-            raise ValueError("Both `reasoning` and `signature` in a single streaming chunk isn't supported.")
-
         if partial_json is not None:
             return "input_json_delta", ContentJsonBlockDelta(type="input_json_delta", partial_json=partial_json)
-        elif reasoning_content:
-            return "thinking_delta", ContentThinkingBlockDelta(type="thinking_delta", thinking=reasoning_content)
         elif reasoning_signature:
             return "signature_delta", ContentThinkingSignatureBlockDelta(
                 type="signature_delta", signature=reasoning_signature
             )
+        elif reasoning_content:
+            return "thinking_delta", ContentThinkingBlockDelta(type="thinking_delta", thinking=reasoning_content)
         else:
             return "text_delta", ContentTextBlockDelta(type="text_delta", text=text)
 

tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_anthropic_experimental_pass_through_adapters_transformation.py

@@ -256,7 +256,14 @@ def test_translate_streaming_openai_chunk_to_anthropic_thinking_signature_block(
     }
 
 
-def test_translate_streaming_openai_chunk_to_anthropic_raises_when_thinking_and_signature_content_block():
+def test_translate_streaming_openai_chunk_to_anthropic_content_block_thinking_and_signature():
+    """The content-block classifier must treat a chunk carrying both ``thinking``
+    and ``signature`` as a ``thinking`` block instead of raising.
+
+    Such a chunk is the terminal signature event of an already-open thinking block,
+    so classifying it as ``thinking`` keeps the stream on the same block rather than
+    500'ing. Before the fix this raised ``ValueError``.
+    """
     choices = [
         StreamingChoices(
             finish_reason=None,
@@ -289,10 +296,14 @@ def test_translate_streaming_openai_chunk_to_anthropic_raises_when_thinking_and_
         )
     ]
 
-    with pytest.raises(ValueError):
-        LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic_content_block(
-            choices=choices
-        )
+    (
+        block_type,
+        content_block_start,
+    ) = LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic_content_block(
+        choices=choices
+    )
+
+    assert block_type == "thinking"
 
 
 def test_translate_anthropic_messages_to_openai_thinking_blocks():
@@ -738,7 +749,17 @@ def test_translate_streaming_openai_chunk_to_anthropic_with_thinking():
     assert content_block_delta["signature"] == "sigsig"
 
 
-def test_translate_streaming_openai_chunk_to_anthropic_raises_when_thinking_and_signature():
+def test_translate_streaming_openai_chunk_to_anthropic_emits_signature_when_thinking_and_signature():
+    """A single streaming chunk carrying both ``thinking`` and ``signature`` must
+    translate to a ``signature_delta``, not crash.
+
+    litellm's Anthropic streaming handler emits the ``signature_delta`` event as an
+    OpenAI chunk whose ``thinking_blocks`` entry re-states the full accumulated
+    thinking text alongside the signature (see anthropic/chat/handler.py). That text
+    was already streamed as ``thinking_delta`` chunks, so the signature must win and
+    the duplicate thinking must not be re-emitted. Before the fix this raised
+    ``ValueError`` and 500'd the whole stream, breaking Claude Code through the proxy.
+    """
     choices = [
         StreamingChoices(
             finish_reason=None,
@@ -771,10 +792,25 @@ def test_translate_streaming_openai_chunk_to_anthropic_raises_when_thinking_and_
         )
     ]
 
-    with pytest.raises(ValueError):
-        LiteLLMAnthropicMessagesAdapter()._translate_streaming_openai_chunk_to_anthropic(
-            choices=choices
-        )
+    adapter = LiteLLMAnthropicMessagesAdapter()
+
+    (
+        type_of_content,
+        content_block_delta,
+    ) = adapter._translate_streaming_openai_chunk_to_anthropic(choices=choices)
+
+    assert type_of_content == "signature_delta"
+    assert content_block_delta["type"] == "signature_delta"
+    assert content_block_delta["signature"] == "sigsig"
+
+    (
+        block_type,
+        content_block_start,
+    ) = adapter._translate_streaming_openai_chunk_to_anthropic_content_block(
+        choices=choices
+    )
+
+    assert block_type == "thinking"
 
 
 def test_translate_anthropic_messages_to_openai_user_message_with_base64_image():

tests/test_litellm/llms/anthropic/experimental_pass_through/adapters/test_streaming_iterator_first_delta.py

@@ -438,6 +438,58 @@ async def test_empty_reasoning_delta_mid_thinking_block_is_suppressed_async():
     _assert_empty_reasoning_delta_suppressed(await _drain_async(wrapper))
 
 
+def _full_snapshot_signature_chunks() -> List[MagicMock]:
+    """Mirror litellm's real Anthropic streaming: incremental ``thinking_delta``
+    chunks (empty signature), then a terminal chunk whose ``thinking_blocks`` entry
+    re-states the *full accumulated thinking text* together with the signature
+    (anthropic/chat/handler.py builds the signature_delta event this way), then the
+    answer text.
+    """
+    return [
+        _thinking_chunk("Let me "),
+        _thinking_chunk("think about it."),
+        _thinking_chunk("Let me think about it.", signature="sig-abc"),
+        _make_chunk(Delta(content="42")),
+        _make_chunk(Delta(content=None), finish_reason="stop"),
+    ]
+
+
+def _assert_full_snapshot_signature_handled(events: List[dict]) -> None:
+    _assert_deltas_match_their_block_type(events)
+    # The full-text snapshot on the signature chunk must NOT be re-emitted as an
+    # extra thinking_delta (it was already streamed incrementally) - otherwise the
+    # client renders the reasoning twice.
+    assert _thinking_deltas(events) == ["Let me ", "think about it."]
+    assert "".join(_thinking_deltas(events)) == "Let me think about it."
+    assert _signature_deltas(events) == ["sig-abc"]
+    assert _text_deltas(events) == ["42"]
+
+
+def test_full_thinking_snapshot_with_signature_emits_signature_only_sync():
+    """Regression: a terminal thinking chunk carrying both the full thinking text
+    and the signature used to raise ``ValueError`` (500) mid-stream, breaking every
+    Claude Code request routed through the proxy with an extended-thinking model. It
+    must instead emit a single ``signature_delta`` without duplicating the thinking.
+    """
+    wrapper = AnthropicStreamWrapper(
+        completion_stream=iter(_full_snapshot_signature_chunks()),
+        model="claude-x",
+    )
+    _assert_full_snapshot_signature_handled(_drain_sync(wrapper))
+
+
+@pytest.mark.asyncio
+async def test_full_thinking_snapshot_with_signature_emits_signature_only_async():
+    """Async twin - the proxy serves the async iterator, so the crash must be gone
+    on that path too.
+    """
+    wrapper = AnthropicStreamWrapper(
+        completion_stream=_AsyncStream(_full_snapshot_signature_chunks()),
+        model="claude-x",
+    )
+    _assert_full_snapshot_signature_handled(await _drain_async(wrapper))
+
+
 def test_empty_content_chunk_mid_text_block_is_suppressed_sync():
     """An empty-content chunk arriving mid-text-block (no transition) used to
     emit a pointless ``text_delta {"text": ""}``; it must be dropped without