diff --git a/eval_protocol/mcp/execution/manager.py b/eval_protocol/mcp/execution/manager.py
index 8e461b49..d6cb2b83 100644
--- a/eval_protocol/mcp/execution/manager.py
+++ b/eval_protocol/mcp/execution/manager.py
@@ -101,13 +101,12 @@ def execute_rollouts(
 
         async def _execute_with_semaphore(idx):
             async with semaphore:
+                evaluation_row: EvaluationRow = evaluation_rows[idx]
+
                 trajectory = await self._execute_rollout(
-                    envs, policy, idx, steps, openai_logger, recording_mode, playback_mode, start_time
+                    envs, policy, idx, steps, openai_logger, recording_mode, playback_mode, start_time, evaluation_row
                 )
 
-                # Convert trajectory to EvaluationRow immediately
-                evaluation_row: EvaluationRow = evaluation_rows[idx]
-
                 # Handle multimodal content by extracting text from complex content structures
                 messages = []
                 for msg in trajectory.conversation_history:
@@ -161,6 +160,7 @@ async def _execute_rollout(
         recording_mode: bool,
         playback_mode: bool,
         start_time: float,
+        evaluation_row: Optional[EvaluationRow] = None,
     ) -> Trajectory:
         """
         Execute a single rollout for one environment (async version for thread execution).
@@ -170,6 +170,25 @@ async def _execute_rollout(
         session = envs.sessions[rollout_idx]
         dataset_row = envs.dataset_rows[rollout_idx]
 
+        # Helper function to sync conversation history to evaluation_row.messages
+        def update_evaluation_row_messages():
+            if evaluation_row:
+
+                def extract_text_content(msg_dict):
+                    msg_copy = dict(msg_dict)
+                    if isinstance(msg_copy.get("content"), list):
+                        for content_block in msg_copy["content"]:
+                            if isinstance(content_block, dict) and content_block.get("type") == "text":
+                                msg_copy["content"] = content_block.get("text", "")
+                                break
+                        else:
+                            msg_copy["content"] = ""
+                    return msg_copy
+
+                evaluation_row.messages = [
+                    Message.model_validate(extract_text_content(msg)) for msg in trajectory.conversation_history
+                ]
+
         # Initialize trajectory
         trajectory = Trajectory(
             session=session,
@@ -223,6 +242,7 @@ async def _execute_rollout(
                 {"role": "system", "content": system_prompt},
                 {"role": "user", "content": user_prompt},
             ]
+            update_evaluation_row_messages()
 
             logger.info(f"🎯 Starting rollout {rollout_idx} in thread {threading.current_thread().name}")
 
@@ -251,6 +271,7 @@ async def _execute_rollout(
 
                         user_prompt = envs.format_user_prompt(rollout_idx, user_content)
                         trajectory.conversation_history.append({"role": "user", "content": user_prompt})
+                        update_evaluation_row_messages()
 
                         # Check if user simulator signaled termination
                         if UserSimulator.is_stop(user_message):
@@ -262,6 +283,7 @@ async def _execute_rollout(
                     tool_calls, usage_stats, finish_reason = await policy(
                         tool_schema, rollout_idx, trajectory.conversation_history
                     )
+                    update_evaluation_row_messages()
 
                     # calc llm usage stats happened in this turn if there is aany
                     if usage_stats:
@@ -297,6 +319,7 @@ async def _execute_rollout(
                             env_end,
                             info,
                         )
+                        update_evaluation_row_messages()
 
                         # Update trajectory with both data and control plane information
                         trajectory.observations.append(observation)
@@ -379,6 +402,7 @@ async def _execute_rollout(
                     _, usage_stats, finish_reason = await policy(
                         tool_schema, rollout_idx, trajectory.conversation_history
                     )
+                    update_evaluation_row_messages()
                     if usage_stats:
                         trajectory.usage["prompt_tokens"] += usage_stats.prompt_tokens
                         trajectory.usage["completion_tokens"] += usage_stats.completion_tokens