diff --git a/backend/open_webui/utils/middleware.py b/backend/open_webui/utils/middleware.py
index 031c0e53f6..2b789f3f17 100644
--- a/backend/open_webui/utils/middleware.py
+++ b/backend/open_webui/utils/middleware.py
@@ -848,7 +848,7 @@ async def chat_image_generation_handler(
                 }
             )
 
-            system_message_content = f"<context>Image generation was attempted but failed. The system is currently unable to generate the image. Tell the user that an error occurred: {error_message}</context>"
+            system_message_content = f"<context>Image generation was attempted but failed. The system is currently unable to generate the image. Tell the user that the following error occurred: {error_message}</context>"
 
     else:
         # Create image(s)
@@ -911,7 +911,7 @@ async def chat_image_generation_handler(
                 }
             )
 
-            system_message_content = "<context>The requested image has been created and is now being shown to the user. Let them know that it has been generated.</context>"
+            system_message_content = "<context>The requested image has been created by the system successfully and is now being shown to the user. Let the user know that the image they requested has been generated and is now shown in the chat.</context>"
         except Exception as e:
             log.debug(e)
 
@@ -932,7 +932,7 @@ async def chat_image_generation_handler(
                 }
             )
 
-            system_message_content = f"<context>Image generation was attempted but failed. The system is currently unable to generate the image. Tell the user that an error occurred: {error_message}</context>"
+            system_message_content = f"<context>Image generation was attempted but failed because of an error. The system is currently unable to generate the image. Tell the user that the following error occurred: {error_message}</context>"
 
     if system_message_content:
         form_data["messages"] = add_or_update_system_message(