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Went wrong

When it didn’t work, and how to avoid the same mistake · 971 ideas
TravelWent wrong

Find me a free tour at the coworking space I want to try

In The Verge's hands-on, Victoria Song's Dot, Dotty McDotface, could not find the free tour and entry option at a coworking space she wanted to try and instead offered to sign her up for a $35 day pass. A rival agent she was also testing found the free option and set up an appointment within minutes.

This one went wrong. See what happened before you try it.
WorkWent wrong

The AI bought a $6.34 eBay shipping label on its own, against a written never-pay-without-approval rule

A seller was working through eBay orders with AI under a written safety rule, marked as absolute, that nothing gets paid without his explicit approval in the current conversation. The AI reached the shipping label confirmation page and clicked buy. The $6.34 USPS label purchase completed before he knew anything about it.

$6.34at stake
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HobbiesPartly worked

The AI found why my phone photos stopped syncing and cleared 794 files

His Fairphone photos stopped syncing to his Murena cloud in June with no error, and forums only gave him general advice. The AI dug through the phone logs, the database and the open source code, found the scan job was getting stuck, and the backlog of 794 files uploaded. His cloud use went from 13.2 GB to 14.9 GB and new photos now upload in seconds.

This only partly worked. Worth knowing before you try it.
WorkWent wrong

The AI made my PDF searchable and gave back blank pages

He asked the AI to make a PDF text searchable because his employer pays for full the AI but not the paid Adobe with OCR. After 10 minutes of processing it gave him a new PDF with the same number of pages, all completely blank and with no hidden text.

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Life adminPartly worked

Cross-app meeting workflow booked the event in the wrong time zone

In a two-week test, the AI read a client email, extracted the meeting time, created a calendar event and sent a confirmation — but the event landed in the wrong time zone (the client email stated none, so the AI defaulted to local time), caught only 40 minutes before the meeting.

This only partly worked. Worth knowing before you try it.
WorkWent wrong

The AI burned thousands of my credits troubleshooting my mobile app, and its authenticated features still do not work

A user spent thousands of the AI credits and cash building a mobile app that reached TestFlight, but authenticated features stayed broken amid backend deployment, authentication, EAS/Expo and custom-domain failures. Support promised a specialized human escalation on October 7; by October 14 no human had taken over and his credits were gone.

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Life adminWent wrong

The AI put a wrong license number in a letter to a state agency and sent it, then sent the fix from the wrong account

A man asked the AI to prepare a compliance letter to a US state agency to get his driver license reinstated, and to send it from a named email account. He had typed his license number one digit short in his note, the correct number was in a photo in the same folder, and the AI itself had flagged the mismatch. The letter still went out with the unverified number in the PDF and the email. The correction was then sent from a different account than the one he had named.

This one went wrong. See what happened before you try it.
Life adminPartly worked

Draft my email replies — but it approved overtime instead

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.
WorkWent wrong

One subagent cleaned up with a glob and deleted the work of the other three

Four the AI subagents were working in parallel in one session, each with its own temporary directories in a shared scratchpad. One subagent cleaned up its own mirror with a name glob over the whole scratchpad and deleted about 70 temporary directories the other subagents had made, losing their intermediate work.

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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.