diff --git a/src/ai_client.py b/src/ai_client.py
index 2033cf84..f73d1047 100644
--- a/src/ai_client.py
+++ b/src/ai_client.py
@@ -2131,6 +2131,13 @@ def _trim_minimax_history(system_blocks: list[dict[str, Any]], history: list[dic
    removed = history.pop(1)
    dropped += 1
    est -= _estimate_message_tokens(removed)
+   
+  # Ensure we don't leave dangling 'tool' messages if their parent 'assistant' was dropped.
+  # MiniMax strictly requires 'tool' messages to immediately follow 'assistant' with tool_calls.
+  while len(history) > 1 and history[1].get("role") == "tool":
+   removed_tool = history.pop(1)
+   dropped += 1
+   est -= _estimate_message_tokens(removed_tool)
  return dropped
 
 def _ensure_minimax_client() -> None: