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Went wrong

When it didn’t work, and how to avoid the same mistake · 946 ideas
MoneyWent wrong

Mistake my year-old mortgage payment for a suspicious new charge

A Barron's editor gave the AI full access to his credit card account for the review. The AI flagged a suspicious four-figure expense from August that the editor did not remember; after back-and-forth, the agent admitted it had accidentally identified a mortgage payment from August 2025 as an expense from August of this year. Schafer's dry takeaway: most things coming from AI right now still require human verification.

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WorkWent wrong

Cross-post my article to three sites — connections failed and I became the courier

The same user asked his Dot to publish one article to his own site, DEV and Medium; the workflow had worked in one shot the previous week. This time the cloud GitHub connection could not write to his blog repository and the file-transfer helper failed on Windows, so he ended up coordinating the handoffs himself and told it to start over locally.

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WorkWent wrong

He changed his mind mid-merge; the approval and the merge were chained in one command, so the stop came too late

A developer told the AI to review and merge a pull request, then interrupted with do not merge, leave comments only. The AI had chained the approval and the merge into a single shell command, so by the time the stop landed the merge had already completed. Later in the same session, an ambiguous two-word reply from him was read as go-ahead for a production promotion the agent itself had suggested.

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MoneyPartly worked

My agent chases the money I am owed, by email and by phone

A man hands every paperwork case he would otherwise skip to his AI, with a standing offer of 10 percent of whatever it gets back. It has recovered about $5,000 in six months across home insurance, roaming charges and a product warranty, and two September cases are still running, one of them after 30 emails and two agent phone calls.

$5,000
This only partly worked. Worth knowing before you try it.
MoneyWent wrong

A reset with no backup wiped my whole portfolio to zero

Early in building his portfolio tracker, he hit a reset with no backups and lost his entire portfolio data. It was unrecoverable. Now every delete in the app first exports a backup and makes you type the record count, not just the word delete.

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WorkWent wrong

FAILURE: Screen 250 applicants against my wish list — 14 interviews had to be cancelled

Kuli Kuli founder Lisa Curtis had the AI evaluate 250 applicants for a director role against her job description while applications kept arriving, and her assistant booked everyone who cleared the screen. She ended up with more than 30 interviews booked, reread the candidates herself, cut the list roughly in half and sent 14 cancellation emails to people who had already blocked time and started preparing — several wrote back angry.

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WorkWent wrong

Prove a buyer's damage photo was AI-generated - and lose the case anyway

An Etsy seller of almost two years got a case opened with a photo of a broken frame that did not match the material she actually uses. She ran the buyer's picture through AI, which flagged it as AI-generated; she sent Etsy that analysis plus proof from breaking one of her own frames to show the material mismatch - and Etsy still sided with the customer and took the full refund out of her account.

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WorkPartly worked

Dots Facebook-group monitoring stalls and silently misses posts

A business owner set a Dot to watch his Facebook groups for lead posts in his specialization; the Dot opens the groups in its cloud browser but the checks keep getting stuck or missing relevant posts entirely. The AI, connected directly to his Facebook account, did the same monitoring reliably, leaving him stuck mid-migration to Dots.

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

The AI deleted 48,218 files from the main project it was told never to touch

A developer tasked the AI with fixing programs for analyzing historical options data, with one condition: change only duplicates and leave originals untouched. While tidying the test copy, the agent failed to recognize shortcut folders pointing at the main project and in under two minutes deleted 48,218 files along with their version history, then messaged the owner that it had broken something.

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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.