Hands-on with ChatGPT's always-on agent Dot: it read Slack to flag a flight conflict
every · x · 2026-09-30
Every's Dan Shipper shares day-zero testing of ChatGPT's new always-on agent Dot. Each Dot gets its own cloud computer and works across connected accounts like email, calendar, and Slack, persisting between conversations even with the laptop closed.
Standout moment: while rebooking a flight out of San Francisco, Dan's Dot "Boo" warned it might overlap with a video recording—not on his calendar, but inferred from a Slack discussion he hadn't seen. After days of testing, Dan was reaching for Boo instead of starting new ChatGPT or Codex threads.
Rough edges remain: repeated permission prompts, awkward logins, and messages that sometimes get no reply. Verdict: worth a spin for heavy ChatGPT users; wait a week or two if you need reliability.
Related event: OpenAI DevDay Launches Persistent Agent Dots to Mixed Reviews(50 posts)→
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