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Vibe Check: Dots—Always-on Agents in ChatGPT

A proactive agent, by turns flashy and frustrating

September 29, 2026

Last week, between back-to-back model reviews, company strategy calls, writing, and my never-ending hunt for apartment furniture on Facebook Marketplace, I tried to change a flight out of San Francisco. I used my Dot—OpenAI’s proactive, always-on agent, released today—to help me book.

As my Dot displayed its flight research, it warned me, “[This] may overlap with Randy’s Wednesday morning video recording.” Randy Counsman is our head of video, but I had no idea what my Dot meant because there was no video recording on my calendar. It turned out my Dot had read a discussion in Slack that I hadn’t seen, clocked the proposed schedule, and alerted me when I needed it most.

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Dan Shipper is the CEO and cofounder of Every. Every week he explores the frontiers of AI in his column, Chain of Thought, and on his podcast, ‘AI & I.’

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