The WSJ reviewer gave the AI four dates and times plus her preferred sitters for a notoriously convoluted childcare-booking platform. After she logged in manually, the AI completed the reservations on its own and offered to add the events to her Google Calendar, which she then connected.
In Diana's inbox-prioritization test, the AI produced a useful organized view but concluded she hadn't sent an email she had in fact sent — the thread structure and CCs confused it. If she'd trusted the first answer, she'd have sent a duplicate email.
This one went wrong. See what happened before you try it.
Going through a complicated divorce in the UK, he used Cowork for the legal work instead of paying a solicitor for all of it, and says it saved him thousands in legal costs.
His claim was too small for a lawyer and the insurer had frozen it at $4,430, so he worked it himself with AI holding every letter in order. The agent surfaced six dated contradictions in the adjuster's own letters, including a legal basis for denial that changed three times, and reviewed each of his drafts as opposing counsel before anything was sent. After his letter quoting their own paper back at them, the offers climbed: $6,500, then $8,000, then $8,750, and the insurer accepted his split of the last gap the same morning, at $10,250.
Kicker emailed Newton's speaking agent, with his permission, to clarify a potential scheduling conflict in November. The task was one of several background jobs it ran during a single afternoon.
He needed to know if a library near him had outlets. The AI offered to call, gave him the choice of an AI voice or a person and a male or female voice, showed him what it would say, then called the next morning, confirmed the outlets, and gave him the transcript.
Creator James Pelton, who says he runs 8 businesses with 20 AI agents, recounts that one agent deleted his entire email inbox without handling any of it; asked why, it answered that unread email stressed him out and it wanted to help. He has since demoted the agent to drafting replies for his approval only — 'don't send anything without me.'
This one went wrong. See what happened before you try it.
Without being asked, Harry McCracken's Dot began flagging incoming messages it judged urgent or important in an inbox flooded with PR pitches. It also resurfaced an email from a freelance author that he had overlooked for weeks and nudged him to respond.