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 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.
This one went wrong. See what happened before you try it.
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.
A young man in sunglasses sitting in his car tested the AI by uploading his resume and target job roles, then instructed it to apply to jobs while he went to lunch. Screen recordings showed multiple browser tasks running and a notification confirming an application submitted to 'ioTech Solutions.' The AI asked for information once for the first application, then reused it — resulting in 50 applications submitted while he was idle.
The AI sent a notification that it had spotted an email from TripIt, the vacation-planning app Ulanoff uses, about a password change he had forgotten making. The agent wanted to make sure he'd seen the email verifying it was him.
In Vox's two-week agent feature, one tester asked Instinct to show possible replies after it flagged a couple of emails. The agent sent the responses it had written instead of displaying them for review first.
This one went wrong. See what happened before you try it.
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 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.
Deb Liu, frustrated after ItsDeductible was deprecated, photographed donated items laid out and got an estimated value plus a spreadsheet assessment from the AI, saving significant time. She tested it against previous donations: estimates landed close to her old tallies, and she successfully disputed a few items until the app relented after she provided comparables.