CLI Context Limit Exceeded: Graceful Error Handling Needed

Bug Description
When using the CLI for a while with larger outputs (files or logs) I get this - and it totally kills the session. The only way out is to kill the terminal. Needs a softer landing! ⎿  API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"input length and max_tokens exceed context limit: 190174 + 20000 > 204698,
decrease input length or max_tokens and try again"}}

Environment Info

• Platform: macos
• Terminal: Apple_Terminal
• Version: 0.2.19
• Feedback ID: b7631f3f-1703-403f-979a-1f19db723c4a