diff --git a/packages/jupyter-ai/jupyter_ai/chat_handlers/clear.py b/packages/jupyter-ai/jupyter_ai/chat_handlers/clear.py
index 0555abfca..51526801b 100644
--- a/packages/jupyter-ai/jupyter_ai/chat_handlers/clear.py
+++ b/packages/jupyter-ai/jupyter_ai/chat_handlers/clear.py
@@ -6,6 +6,8 @@
 
 
 class ClearChatHandler(BaseChatHandler):
+    """Clear the chat panel and show the help menu"""
+
     id = "clear"
     name = "Clear chat messages"
     help = "Clear the chat window"
@@ -17,10 +19,15 @@ def __init__(self, *args, **kwargs):
         super().__init__(*args, **kwargs)
 
     async def process_message(self, _):
+        tmp_chat_history = self._chat_history[0]
         self._chat_history.clear()
         for handler in self._root_chat_handlers.values():
             if not handler:
                 continue
 
             handler.broadcast_message(ClearMessage())
+
+            self._chat_history = [tmp_chat_history]
+            self.reply(tmp_chat_history.body)
+
             break
diff --git a/packages/jupyter-ai/jupyter_ai/chat_handlers/export.py b/packages/jupyter-ai/jupyter_ai/chat_handlers/export.py
index 3bde63018..ec3f1e53a 100644
--- a/packages/jupyter-ai/jupyter_ai/chat_handlers/export.py
+++ b/packages/jupyter-ai/jupyter_ai/chat_handlers/export.py
@@ -35,7 +35,9 @@ async def process_message(self, message: HumanChatMessage):
             self.chat_message_to_markdown(msg) for msg in self._chat_history
         )
         args = self.parse_args(message)
-        chat_filename = args.path[0] if args.path else "chat_history"
+        chat_filename = (
+            args.path[0] if (args.path and args.path[0] != "") else "chat_history"
+        )  # Handles both empty args and double tap <Enter> key
         chat_filename = f"{chat_filename}-{datetime.now():%Y-%m-%d-%H-%M}.md"
         chat_file = os.path.join(self.root_dir, chat_filename)
         with open(chat_file, "w") as chat_history: