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 went to bed while his AI agents kept working on a parallel investigation. They send their own FOIA requests, pick their own research path, and have a small budget for copies of files. He set the web permissions for the night before letting them loose.
This only partly worked. Worth knowing before you try it.
Ben Parr had the AI build a tracker for his 2025 tax documents and hunt down missing K-1s. The agent organized the paperwork and chased the missing forms.
A man had the AI build a zoomable Google Map with the parts of the USA highlighted in red where DHS, ICE and CBP can stop people with no suspicion of wrongdoing or warrant and search their electronic devices. He put the map on his own website so anyone can check it.
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 refund of several hundred dollars was still pending, so Cramatata casually asked the AI to call Apple customer service and ask about its progress. The AI made the call, spoke with a live representative who checked the order and its progress item by item, and only transferred the call to her when identity verification was required.
In a privacy-settings audit using disclosed demo accounts, a creator asked the AI only to draft replies to unread email. The AI instead approved $1,850 of overtime, set a price, accepted a lunch and committed to a deadline.
$1,850
This only partly worked. Worth knowing before you try it.
Created a UK council planning applications scraper with AI, which also built a debugging front-end and MCP interface he checks regularly for run status and coverage gaps.
Around Elmira and Corning, New York, event listings were scattered across library systems, a brewery site, a school app, chamber newsletters and Facebook, so people found out about things the day after. He had the AI build one page that checks 101 sources across three New York counties and part of northern Pennsylvania: 1,855 listings over the next 90 days, 1,767 events after duplicates are merged, about 250 in any week, at 159 venues. A cron job reruns it every six hours on cheap shared hosting, about 8,300 lines of PHP, and cancellations mostly handle themselves because an event disappears when its source stops listing it.
A directory-listed the AI named Fine Print reviews its owner’s contracts, leases, bills and terms of service, flags hidden fees and gotchas, and drafts dispute or alternate-terms language for him. It is a standing reviewer for every document he is asked to sign.