diff --git a/llm_interface.py b/llm_interface.py
index 91978b2..a62b738 100644
--- a/llm_interface.py
+++ b/llm_interface.py
@@ -594,6 +594,15 @@ class LLMInterface:
                         logger.info(f"[LLM] Message #{message_count}: {msg_type}")
 
                     if isinstance(message, AssistantMessage) and hasattr(message, 'content'):
+                        # DEBUG: Log content structure for first few messages
+                        if message_count <= 10:
+                            content_type = type(message.content).__name__
+                            if isinstance(message.content, list):
+                                block_types = [type(b).__name__ if hasattr(b, 'type') else str(type(b)) for b in message.content[:3]]
+                                logger.info(f"[LLM] Message #{message_count} content: list with {len(message.content)} blocks: {block_types}")
+                            else:
+                                logger.info(f"[LLM] Message #{message_count} content: {content_type}")
+                        
                         if isinstance(message.content, str):
                             assistant_messages.append(message.content)
                         elif isinstance(message.content, list):