diff --git a/backend/open_webui/utils/context_compaction.py b/backend/open_webui/utils/context_compaction.py
index fcb313cbbb..3b6c74017a 100644
--- a/backend/open_webui/utils/context_compaction.py
+++ b/backend/open_webui/utils/context_compaction.py
@@ -5,7 +5,6 @@ import logging
 from typing import Any
 
 from fastapi.responses import JSONResponse
-
 from open_webui.models.chats import Chats
 from open_webui.models.config import Config
 from open_webui.utils.misc import get_content_from_message, get_last_user_message, get_message_list
@@ -108,7 +107,9 @@ async def compact_messages_for_request(
         raise
 
     chat_id = metadata.get('chat_id')
-    checkpoint_message_id = metadata.get('user_message_id') or metadata.get('message_id')
+    checkpoint_message_id = (
+        recent_messages[0].get('id') or metadata.get('user_message_id') or metadata.get('message_id')
+    )
     if chat_id and checkpoint_message_id and not chat_id.startswith(('local:', 'channel:')):
         await Chats.upsert_message_to_chat_by_id_and_message_id(
             chat_id,