diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index 659ec179d4..4f8ecf4a7c 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -4100,6 +4100,30 @@ async def streaming_chat_response_handler(response, ctx):
             def full_output():
                 return prior_output + output if prior_output else output
 
+            def get_message_error_content(error):
+                if isinstance(error, HTTPException):
+                    error = error.detail
+                elif isinstance(error, dict):
+                    error = error.get('detail', error)
+                else:
+                    error = str(error)
+
+                return error if isinstance(error, (str, dict)) else str(error)
+
+            async def emit_message_error(error_content):
+                if save_to_chat:
+                    await Chats.upsert_message_to_chat_by_id_and_message_id(
+                        metadata['chat_id'],
+                        metadata['message_id'],
+                        {'error': {'content': error_content}},
+                    )
+                await event_emitter(
+                    {
+                        'type': 'chat:message:error',
+                        'data': {'error': {'content': error_content}},
+                    }
+                )
+
             reasoning_tags_param = metadata.get('params', {}).get('reasoning_tags')
             DETECT_REASONING_TAGS = reasoning_tags_param is not False
 
@@ -5290,7 +5314,9 @@ async def streaming_chat_response_handler(response, ctx):
                         else:
                             break
                     except Exception as e:
-                        log.debug(e)
+                        error_content = get_message_error_content(e)
+                        log.exception('Tool-call continuation failed: %s', error_content)
+                        await emit_message_error(error_content)
                         break
 
                 if (
@@ -5300,18 +5326,7 @@ async def streaming_chat_response_handler(response, ctx):
                 ):
                     log.warning('Tool-call iteration limit reached (%s)', max_tool_call_iterations)
                     error_content = f'Tool-call limit reached ({max_tool_call_iterations} iterations).'
-                    if save_to_chat:
-                        await Chats.upsert_message_to_chat_by_id_and_message_id(
-                            metadata['chat_id'],
-                            metadata['message_id'],
-                            {'error': {'content': error_content}},
-                        )
-                    await event_emitter(
-                        {
-                            'type': 'chat:message:error',
-                            'data': {'error': {'content': error_content}},
-                        }
-                    )
+                    await emit_message_error(error_content)
 
                 if DETECT_CODE_INTERPRETER:
                     MAX_RETRIES = 5
@@ -5483,7 +5498,9 @@ async def streaming_chat_response_handler(response, ctx):
                             else:
                                 break
                         except Exception as e:
-                            log.debug(e)
+                            error_content = get_message_error_content(e)
+                            log.exception('Code interpreter continuation failed: %s', error_content)
+                            await emit_message_error(error_content)
                             break
 
                 # Mark all in-progress items as completed