Before a speaking engagement, Ulanoff couldn't recall where he was talking or where to park. He asked the AI to find the original note from his contact, misspelling the contact's name.
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.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
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He had the AI work out how the When2Meet scheduling site works and turn it into a skill. Now the AI can read his calendar and fill in the When2Meet availability grid by itself.
She asked the AI if it could cancel her Mint Mobile account. The company's chat agent had told her she needed to call in. She gave the AI her Mint details, the AI opened its own chat with the company and got the cancellation done, with no phone call and no talking to people herself.
In a single week of errands, Alec Ellin had the AI trace an iPhone that FedEx had misfiled in its own system and get Apple to refund him for it. The agent worked the problem across two companies' systems instead of him spending the week on hold with either.
A Tesla engineer got an email that passed SPF, DKIM and DMARC and showed a verified check, but felt off, so he had his AI review it without clicking anything; the bot found a hidden phishing link, explained why the standard checks had passed, and wrote a report to xAI with a proposed fix. He then had it add a standing routine that flags likely phishing in his inbox, which has since flagged more messages.
A user was filing a housing co-op’s HPD property registration with AI’s help. Asked whether the $13 registration fee had been paid, the AI said it had been or was not required, based only on a generic billing disclaimer, with no payment record behind it. Asked why a mailed form arrived after the deadline, the AI stated as fact that the deadline runs from the postmark, a rule it had not checked. Both claims were corrected only after he challenged them. A late filing for a building can draw a civil penalty in the $500 to $5,000 range.
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He was helping gather maps of local political boundaries for the Granada Community Services District and the Midcoast Community Council near Half Moon Bay. The AI went through government data sources, extracted and combined the files, and built the exact boundary polygons, which he could then view on a map.
A Reddit user with a facilities background asked the AI to scour matching job postings, tailor a resume for each job board, and submit applications automatically overnight. Job hunting while asleep — the applications went out with per-board tailoring the user never had to do by hand.
Nick Olsen built a system where the AI auto-generates and prints a daily briefing each morning: motivational quote, today's calendar and task list with checkboxes, week preview, Facebook/Google ad spend and performance, fitness checklist, summaries of children's school emails tailored by child, email-derived reminders (bills, urgent items), a daily comic, and a blank notes section.
He runs his email agent on a 2018 computer he already owned. It watches his inbox, flags what matters, sums up threads, finds old emails by topic, takes voice notes and drafts replies, and a second program watches it and messages him within a second if it breaks.
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Agentic skills scan the last 36 hours of email, meetings and chats, triage commitments into Do, Defer, Schedule and Delegate piles, self-update from flagged corrections, and have run since April with no flags needed in months.
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.
Harry McCracken's Dot, Chip, cross-checked his calendar against his email and spotted that a speaking engagement he had entered on one date had been rescheduled by the organizers to a different day, which the confirmation email showed. He says he would otherwise have shown up to an empty room.
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.
In PCMag's five-task gauntlet comparing Dots, the AI and the AI (summarized by WindowsForum), the final test pointed the agents at a Gmail inbox to identify marketing clutter and unsubscribe from the senders. The AI identified the emails but failed to launch its browser to actually follow through on external unsubscribe links when required, leaving the execution undone; Dots, by contrast, catalogued 700+ senders and clicked through unsubscribe pages.
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Every month the family benefits system asks him for a fresh proof of domicile, and a forgotten upload stops the payments. His AI in the Merlin app gets a signed attestation from his landlord, dates and uploads it to the right section before the deadline, and confirms when it is done; three filings in a row have landed, down from about an hour a month plus a fine for a late one.
Gannon Meyer (210K followers) named his AI 'Oscar' (dachshund avatar) to survive 'one of the most chaotic but manageable periods of his life.' The demo shows Oscar drafting and sending an email to a photographer about wedding timing at Perona Farms, removing sales calls from his September calendar, and tracking meals and weight-loss progress toward a wedding goal — while remembering personal context like his recent pickleball ankle injury. Oscar proposes actions but executes only after a
Liberty RPF's author tested the AI heavily himself after it launched in Canada, but his wife's onboarding was the telling detail: delighted by the mascot, she renamed it, changed its color, and asked it to review her email inbox daily — her first real agent job.
When her employer's plan stopped covering her medication, the AI worked out that the plan had a continuation of therapy route and built a full appeal package for her to hand in, arguing the drug was a continuation rather than a new request. She filed it, and her doctor used the letter template it wrote.
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He pasted one prompt into AI, and the AI read the Carly email setup docs itself, finished the signup, and took the verification code. The inbox, named Loopy, now takes tasks by email and asks before replying to anyone outside.
The AI patched the system files that link a USB to serial cable to the Pinewood Derby track for his Cub Scout group. The timers were saved half an hour before the races, a year after the group had to race without timers.
His inheritance case ran across two territories with different legal stances, in two languages that are not English. Working through it with AI, he found a six figure mistake made by the notary, and because the AI taught him the process, he no longer needed his lawyer for every technical question, which cut his legal fees hard.
The AI Crux gave the AI a client email and asked it to extract the proposed meeting time, create a calendar event, and send a confirmation reply. The AI did all three — but silently created the event in the wrong timezone.
This only partly worked. Worth knowing before you try it.
Spark turned one plain sentence into a scheduled task, ran it at 4:11 PM without the user opening the AI, and sent a phone notification. The summary put a government notice and a postpaid bill with its due date first, then publishing updates, then promotions.