diff --git a/private_gpt/ui/ui.py b/private_gpt/ui/ui.py
index abdfb0c6..7de34557 100644
--- a/private_gpt/ui/ui.py
+++ b/private_gpt/ui/ui.py
@@ -159,7 +159,7 @@ class PrivateGptUi:
                     )
 
             # max 20 messages to try to avoid context overflow
-            return history_messages[:20]
+            return history_messages[-20:]
 
         new_message = ChatMessage(content=message, role=MessageRole.USER)
         all_messages = [*build_history(), new_message]