diff --git a/arcade/arcade/cli/main.py b/arcade/arcade/cli/main.py
index 5ce81981..1b20c729 100644
--- a/arcade/arcade/cli/main.py
+++ b/arcade/arcade/cli/main.py
@@ -267,6 +267,7 @@ def chat(
                     wait_for_authorization_completion(client, tool_authorization)
                 # re-run the chat request now that authorization is complete
                 try:
+                    history.pop()
                     chat_result = handle_chat_interaction(
                         client, model, history, user_email, stream
                     )