The author describes using AI to resolve a six-month-old travel medical insurance claim with Cigna. The AI called the insurer, was transparent about being an AI, conducted the call politely (impressing the representative), and — because final consent was required — called the author's phone and connected the parties so he could approve verbally.
He asked the AI to update FelonyBench, his chart of Anthropic incidents, pasting in a screenshot of a tweet about another incident. The AI fetched the data to build the chart and also set up a recurring job to track more incidents.
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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Rachel D. Gainsbrugh (someone, ~3.5K followers, AI/systems creator) signed up for the AI on Sept 13, 2026, connected her calendar read-only, and typed six standing errand rules once — including a 7:05 AM daily calendar scan that flags overlapping meetings or ones falling inside a flight — then handed it two long-dodged errands (an appointment blocked by a flight, a subscription update).
A father's son grew his hair since Covid and cut it to donate to a charity that makes wigs for children with cancer. The father kept putting off making a poster, then gave the AI a couple of photos and a video link and it built the poster while he worked. His boss put it up, workmates pledged enough to fund the wig, 250 pounds. Later, from the car, he voice prompted the AI to remake the poster in his son's words for the boy's school, and forwarded it on WhatsApp when they arrived.
Ahead of an apartment move, a reviewer asked the AI for a day-by-day packing schedule. The AI built one with sessions capped at 30 minutes, sequencing items so things the person won't need before the move get packed first.
The AI prepared and filed Australian visitor visas for a couple travelling to Brisbane, and caught a placeholder birthdate in the details before submission, confirming the correction over WhatsApp.
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.
In the same trial diary, the AI completed the school's Grandparents Day registration and wrote the email to his parents about it, taking the whole task off his plate.
Tetsuro Miyatake had the AI call Volvo Cars as 'Hailey' on Matt Schlicht's behalf to check routine-maintenance availability for his XC90. The service department had openings all the following week starting Monday at 8 a.m.; the AI clarified it was checking availability only, not booking, since a phone number was still needed.