Shuffle again

A random mix from the whole library. Shuffle for a new set.

Went wrong

When it didn’t work, and how to avoid the same mistake · 970 ideas
HealthWent wrong

My agent called my dentist to book a checkup but could not finish without my insurance details

Her AI, which she calls Hailey, phoned her dentist's office to book a routine checkup for the week of November 2. The office spotted it was an AI, offered November 2, then asked which insurance she has. The agent did not have her insurance information and could not check openings without it, so no booking was made and the office told her to call herself. She shared the full call transcript.

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

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

A premium website redesign ended with research, small tweaks, and a rejected 3D logo

A company owner asked the AI for a premium redesign of his website. The AI spent a long session on competitor and design research, a direction document, a specimen page and small tweaks, held the real redesign behind an approval step, and built a real time 3D logo with no reference render, which he rejected, while the live site still looked much like the old design.

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

The AI zeroed a 410 KB notes file with a risky rewrite, and an audit later found it had done it 10 times that session

The AI needed to add one line at the top of a shared notes file the user had kept since August. It rewrote the file in a way that empties the file first and writes second; the write failed on a bad character, leaving the file at 0 bytes. The file survived only because an outside backup existed. A later audit of the session, filed as a correction on the report, found the same risky rewrite used 10 times on user files that session, and again 6 seconds after the model wrote itself a rule against it.

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

The AI swore my two Stripe accounts would stay separate. They linked, and it cannot be undone

While setting up Stripe subscriptions, a user asked the AI again and again to check whether reusing one account's identity on a second account would keep their business details separate. The AI said yes with confidence and never checked. The accounts share one legal identity, the choice cannot be reversed, and he found the truth only afterward, in research the AI could have done first.

This one went wrong. See what happened before you try it.
Show 10 more

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.