fix(streaming): tool calls and race conditions for SDK mode

ccproxy/llms/formatters/openai_to_anthropic/requests.py

@@ -6,10 +6,96 @@
 from typing import Any
 
 from ccproxy.core.constants import DEFAULT_MAX_TOKENS
+from ccproxy.core.logging import get_logger
 from ccproxy.llms.models import anthropic as anthropic_models
 from ccproxy.llms.models import openai as openai_models
 
 
+logger = get_logger(__name__)
+
+
+def _sanitize_tool_results(messages: list[dict[str, Any]]) -> list[dict[str, Any]]:
+    """Remove orphaned tool_result blocks that don't have matching tool_use blocks.
+
+    The Anthropic API requires that each tool_result block must have a corresponding
+    tool_use block in the immediately preceding assistant message. This function removes
+    tool_result blocks that don't meet this requirement, converting them to text to
+    preserve information.
+
+    Args:
+        messages: List of Anthropic format messages
+
+    Returns:
+        Sanitized messages with orphaned tool_results removed or converted to text
+    """
+    if not messages:
+        return messages
+
+    sanitized = []
+    for i, msg in enumerate(messages):
+        if msg.get("role") == "user" and isinstance(msg.get("content"), list):
+            # Find tool_use_ids from the immediately preceding assistant message
+            valid_tool_use_ids: set[str] = set()
+            if i > 0 and messages[i - 1].get("role") == "assistant":
+                prev_content = messages[i - 1].get("content", [])
+                if isinstance(prev_content, list):
+                    for block in prev_content:
+                        if isinstance(block, dict) and block.get("type") == "tool_use":
+                            tool_id = block.get("id")
+                            if tool_id:
+                                valid_tool_use_ids.add(tool_id)
+
+            # Filter content blocks
+            new_content = []
+            orphaned_results = []
+            for block in msg["content"]:
+                if isinstance(block, dict) and block.get("type") == "tool_result":
+                    tool_use_id = block.get("tool_use_id")
+                    if tool_use_id in valid_tool_use_ids:
+                        new_content.append(block)
+                    else:
+                        # Track orphaned tool_result for conversion to text
+                        orphaned_results.append(block)
+                        logger.warning(
+                            "orphaned_tool_result_removed",
+                            tool_use_id=tool_use_id,
+                            valid_ids=list(valid_tool_use_ids),
+                            message_index=i,
+                            category="message_sanitization",
+                        )
+                else:
+                    new_content.append(block)
+
+            # Convert orphaned results to text block to preserve information
+            if orphaned_results:
+                orphan_text = "[Previous tool results from compacted history]\n"
+                for orphan in orphaned_results:
+                    content = orphan.get("content", "")
+                    if isinstance(content, list):
+                        text_parts = []
+                        for c in content:
+                            if isinstance(c, dict) and c.get("type") == "text":
+                                text_parts.append(c.get("text", ""))
+                        content = "\n".join(text_parts)
+                    # Truncate long content
+                    content_str = str(content)
+                    if len(content_str) > 500:
+                        content_str = content_str[:500] + "..."
+                    orphan_text += f"- Tool {orphan.get('tool_use_id', 'unknown')}: {content_str}\n"
+
+                # Add as text block at the beginning
+                new_content.insert(0, {"type": "text", "text": orphan_text})
+
+            # Update message content (only if we have content left)
+            if new_content:
+                sanitized.append({**msg, "content": new_content})
+            # If no content left, skip this message entirely
+        else:
+            sanitized.append(msg)
+
+    return sanitized
+
+
 async def convert__openai_chat_to_anthropic_message__request(
     request: openai_models.ChatCompletionRequest,
 ) -> anthropic_models.CreateMessageRequest:
@@ -165,6 +251,9 @@ async def convert__openai_chat_to_anthropic_message__request(
             else:
                 out_messages.append({"role": "user", "content": content})
 
+    # Sanitize tool_result blocks to ensure they have matching tool_use blocks
+    out_messages = _sanitize_tool_results(out_messages)
+
     payload_data: dict[str, Any] = {
         "model": model,
         "messages": out_messages,
@@ -581,4 +670,5 @@ def derive_thinking_config(
 __all__ = [
     "convert__openai_chat_to_anthropic_message__request",
     "convert__openai_responses_to_anthropic_message__request",
+    "_sanitize_tool_results",  # Exposed for testing
 ]

ccproxy/llms/streaming/processors.py

@@ -421,18 +421,33 @@ async def _process_chunk(
                 self.current_thinking_text = ""
                 self.current_thinking_signature = None
 
-            elif (
-                self.tool_calls
-                and self.enable_tool_calls
-                and self.output_format == "sse"
-            ):
-                # Send completed tool calls (only for SSE format, dict format sends immediately)
-                for tool_call in self.tool_calls.values():
+            elif self.tool_calls and self.enable_tool_calls:
+                # Send completed tool calls for both SSE and dict formats
+                # Previous bug: Only sent for SSE format, causing dict format (SDK mode) to miss tool calls
+                logger.trace(
+                    "openai_stream_sending_tool_calls",
+                    tool_count=len(self.tool_calls),
+                    output_format=self.output_format,
+                    category="streaming_conversion",
+                )
+
+                for tool_call_index, (tool_call_id, tool_call) in enumerate(
+                    self.tool_calls.items()
+                ):
+                    logger.trace(
+                        "openai_stream_tool_call_yielding",
+                        tool_call_id=tool_call_id,
+                        tool_name=tool_call["name"],
+                        has_arguments=bool(tool_call["arguments"]),
+                        index=tool_call_index,
+                        category="streaming_conversion",
+                    )
+
                     yield self._format_chunk_output(
                         delta={
                             "tool_calls": [
                                 {
-                                    "index": 0,
+                                    "index": tool_call_index,
                                     "id": tool_call["id"],
                                     "type": "function",
                                     "function": {
@@ -446,6 +461,14 @@ async def _process_chunk(
                         }
                     )
 
+                # Clear tool_calls after yielding to prevent duplicates
+                logger.trace(
+                    "openai_stream_clearing_tool_calls",
+                    cleared_count=len(self.tool_calls),
+                    category="streaming_conversion",
+                )
+                self.tool_calls.clear()
+
         elif chunk_type == "message_delta":
             # Usage information
             usage = chunk_data.get("usage", {})

ccproxy/plugins/claude_sdk/stream_handle.py

@@ -74,26 +74,49 @@ def __init__(
     async def create_listener(self) -> AsyncIterator[Any]:
         """Create a new listener for this stream.
 
-        This method starts the worker on first listener and returns
-        an async iterator for consuming messages.
+        This method creates the worker if needed, pre-registers the listener,
+        then starts the worker. This ordering prevents race conditions where
+        fast STDIO tools could return results before the listener was ready.
 
         Yields:
             Messages from the stream
         """
-        # Start worker if needed
-        await self._ensure_worker_started()
+        # Create worker if needed (but don't start yet)
+        async with self._worker_lock:
+            if self._worker is None:
+                worker_id = f"{self.handle_id}-worker"
+                self._worker = StreamWorker(
+                    worker_id=worker_id,
+                    message_iterator=self._message_iterator,
+                    session_id=self.session_id,
+                    request_id=self.request_id,
+                    session_client=self._session_client,
+                    stream_handle=self,
+                )
+                logger.debug(
+                    "stream_handle_worker_created",
+                    handle_id=self.handle_id,
+                    worker_id=worker_id,
+                    session_id=self.session_id,
+                    category="streaming",
+                )
 
         if not self._worker:
-            raise RuntimeError("Failed to start stream worker")
+            raise RuntimeError("Failed to create stream worker")
 
-        # Create listener
+        # Pre-register listener BEFORE starting worker
+        # This fixes the race condition where fast STDIO tools could
+        # return results before the listener was ready
         queue = self._worker.get_message_queue()
         listener = await queue.create_listener()
         self._listeners[listener.listener_id] = listener
 
         if self._first_listener_at is None:
             self._first_listener_at = time.time()
 
+        # NOW start the worker (after listener is registered)
+        await self._worker.start()
+
         logger.debug(
             "stream_handle_listener_created",
             handle_id=self.handle_id,
@@ -135,32 +158,6 @@ async def create_listener(self) -> AsyncIterator[Any]:
             # Check if we should trigger cleanup
             await self._check_cleanup()
 
-    async def _ensure_worker_started(self) -> None:
-        """Ensure the worker is started, creating it if needed."""
-        async with self._worker_lock:
-            if self._worker is None:
-                # Create worker
-                worker_id = f"{self.handle_id}-worker"
-                self._worker = StreamWorker(
-                    worker_id=worker_id,
-                    message_iterator=self._message_iterator,
-                    session_id=self.session_id,
-                    request_id=self.request_id,
-                    session_client=self._session_client,
-                    stream_handle=self,  # Pass self for message tracking
-                )
-
-                # Start worker
-                await self._worker.start()
-
-                logger.debug(
-                    "stream_handle_worker_created",
-                    handle_id=self.handle_id,
-                    worker_id=worker_id,
-                    session_id=self.session_id,
-                    category="streaming",
-                )
-
     async def _remove_listener(self, listener_id: str) -> None:
         """Remove a listener and clean it up.
 

ccproxy/plugins/claude_sdk/stream_worker.py

@@ -194,12 +194,12 @@ async def _run_worker(self) -> None:
                 self._total_messages += 1
                 self._last_message_time = time.time()
 
-                # Check if we have listeners
-                if await self._message_queue.has_listeners():
-                    # Broadcast to all listeners
-                    delivered_count = await self._message_queue.broadcast(message)
-                    self._messages_delivered += delivered_count
+                # Always broadcast - the queue handles no-listeners case atomically
+                # Previous bug: Separate has_listeners() check was racy with fast STDIO tools
+                delivered_count = await self._message_queue.broadcast(message)
 
+                if delivered_count > 0:
+                    self._messages_delivered += delivered_count
                     logger.trace(
                         "stream_worker_message_delivered",
                         worker_id=self.worker_id,
@@ -208,9 +208,8 @@ async def _run_worker(self) -> None:
                         total_messages=self._total_messages,
                     )
                 else:
-                    # No listeners - discard message
+                    # No listeners at broadcast time - message discarded
                     self._messages_discarded += 1
-
                     logger.trace(
                         "stream_worker_message_discarded",
                         worker_id=self.worker_id,