diff --git a/backend/open_webui/utils/memory.py b/backend/open_webui/utils/memory.py
index 1308c44dd8..f34b261b61 100644
--- a/backend/open_webui/utils/memory.py
+++ b/backend/open_webui/utils/memory.py
@@ -403,6 +403,9 @@ async def add_memory_context(request, form_data: dict, user, model: dict | None
         return form_data
 
     memory_context = f'{MEMORY_CONTEXT_OPEN}\n{rendered}\n{MEMORY_CONTEXT_CLOSE}'
+    if messages and messages[0].get('role') == 'system':
+        # Without a blank line, models echo the block as part of the prompt
+        memory_context = f'\n{memory_context}'
     form_data['messages'] = add_or_update_system_message(memory_context, messages, append=True)
     return form_data