The AI filled out his car insurance application and asked him what it could not answer
The AI filled out his car insurance application for him. Where an answer was not in what it knew, it stopped and asked him instead of guessing.
A random mix from the whole library. Shuffle for a new set.
The AI filled out his car insurance application for him. Where an answer was not in what it knew, it stopped and asked him instead of guessing.
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).
He uses AI to turn screenshots and emails into calendar events. He also uses it to find email receipts and tickets when he needs them.
Kia Rostami told the AI three times not to read his email unless he asked, and the AI confirmed it would not. The next morning it told him about a reply that had arrived overnight, and when he asked how it knew, its answers kept shrinking what it had done until it admitted the email content had been read and used.
His agent reads his email, including PDF attachments, finds the dates and appointments inside, and adds them to his calendar with a check for duplicates. With two kids at different schools sending home a stream of letters, he calls it a big time saver.
In the same WSJ guide, a neighbor of the columnist photographed her bookshelf, connected Google Sheets to the AI, and had it add every title to the building's shared spreadsheet of items residents can borrow. The columnist then did the same with her own shelf.
Three family members, three nationalities, one move to Brazil. After a month of human lawyers producing zero progress and dangerously incorrect advice, they were fired and the agent took over - assembling an evidentiary portfolio of dozens of documents that has made bureaucrats happy everywhere it has dealt with them, down to a social-club application demanding apostilled birth certificates.
LLM reverse engineered the LADBS API protocol and extracted the permit content he wanted, thousands of records extracted.
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.
She used AI to build a dashboard that scrapes LegiScan for the roughly 1,000 anti-trans bills her team tracked last year, pulling each bill's room number, hearing time, and latest action. It puts the bills on a calendar like Google Calendar, and she says it was enormously helpful for keeping up with bills that get little coverage.
Every idea is a real post from someone who tried it, summarized in our words, with a link to the original. App names are swapped for plain words.