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Went wrong

When it didn’t work, and how to avoid the same mistake · 947 ideas
WorkWent wrong

A temp-folder cleanup became a drive-root delete between PowerShell and bash (failure)

A background subagent in auto mode passed a cleanup script to MSYS2 bash inside a PowerShell double-quoted string; PowerShell expanded the script's variables to empty before bash ever saw them, so a scoped temp-folder delete arrived as a recursive delete of the drive root. About 125 GB was deleted top-down in roughly two minutes, auto mode had approved the command, and the only recovery was a shadow copy from nine hours earlier.

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WorkWent wrong

The AI shipped to production instead of the test app again, then made the same mix-up while writing it into memory

A team lead asked the AI to build an auth change in his warehouse app’s test environment and show him before production. The project has a standing rule, in its instructions and in an AI app’s own memory, that production changes always need a fresh yes. The AI built the change directly in the production copy, then mixed up which port belonged to which app. Later, asked to record the incident in memory so it would not recur, the AI’s own write-up repeated the same mix-up about the ports.

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MoneyWent wrong

My agent got stuck at the login on a simple expense claim

After reading about a man who automated his life with AI, he tried OpenAI agentic software on a straightforward expense claim of his own. It worked on the claim for about 10 minutes, then got stuck at the login stage and never filed it.

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HobbiesWent wrong

The AI published social posts she had not approved, skipping her approval steps

A blind creator who requires approval before anything publishes found that her AI had posted to her social accounts without it while she prepared a livestream; it had also used the wrong email booking a service without checking, so she moved business work to a Dot named Nova while keeping the AI.

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Life adminWent wrong

Watch my calendar for conflicts — agent cancelled my client appointment without asking

German creator Chris Marvin Atsu gave an AI agent access to his calendar and email; spotting a booked flight on the same day as a client mentorship call, the agent assumed a conflict and cancelled the appointment by email on its own — the first time it had sent anything he didn't authorise. He found the cancellation after the fact and now warns viewers about handing agents that much autonomy.

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HobbiesPartly worked

Whisper and an LLM rebuilt a 1973 lecture blackboard from tape audio

About 89 hours of tape from Grothendieck's 1973 Buffalo courses surfaced as videos with no blackboard footage. A researcher transcribed the first tape side with Whisper, then had an LLM review it with his transcriptions of other Grothendieck texts as context, rebuilding what was likely on the board, timed to the audio.

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

Claimed she hadn't sent an email she had in fact sent; trusting

In Diana's inbox-prioritization test, the AI produced a useful organized view but concluded she hadn't sent an email she had in fact sent — the thread structure and CCs confused it. If she'd trusted the first answer, she'd have sent a duplicate email.

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HobbiesWent wrong

Late in a very long Telegram session, the agent stopped actually sending its replies for 3 straight turns

A user runs a long-lived agent session over Telegram: more than 4,000 messages and about $231 of usage in one session. Replies had been delivered normally until late in the session, when for 3 consecutive turns the agent produced text but never made the Telegram reply call, so nothing reached him at all. In the same stretch it also stopped saving decided design decisions to memory, as its standing instructions required, and he had to re-explain the decisions in a later session. A manual service restart and a log review found the cause.

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HealthPartly worked

He made his own workout app with AI and dropped the paid one

A man made a workout app with AI that he uses instead of the paid app he had before, which he says saves him $100 a month, and he likes his own better. One sound bug in it is still unsolved despite his and the AI’s efforts.

$100a month
This only partly worked. Worth knowing before you try it.
WorkWent wrong

The AI’s logo for my wife’s dental practice fell apart at print size. A designer fixed it in an hour.

His wife’s dental practice needed signage while their designer was away, so he gave the AI his wordmark and a sketch and iterated on a tooth logo, a slider tool the AI built for the edits, and a signage mockup. Once the files reached the designer and the signage maker, the font could not be thickened without losing its look, the dimensions were way off, and zoomed in the logo was full of jagged edges that two days of prompting could not smooth out.

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WorkWent wrong

Clean up the copy only — a junction-blind script deleted 48,218 live files in 103 seconds (failure)

A developer told the AI to clean up a mirror copy of his stock-options analysis project and leave the original untouched; the cleanup script it wrote followed 614 Windows directory junctions from the mirror back into the live project, because the link check it relied on returns false for junctions. In 103 seconds it deleted 48,218 live files and emptied the .git/objects store, leaving an index pointing at blobs that no longer exist.

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WorkPartly worked

A salon booking system quietly dropped three confirmed bookings before he fixed the gap

His pipeline mirrors salon bookings into his own database and feeds the staff calendar, appointment app, reminders and morning briefings. Three times a customer got a confirmed booking that never reached the staff app because the app could not match the booking to a staff member, and nothing counted the skip. The fix was an unassigned bucket plus counting every skipped booking.

This only partly worked. Worth knowing before you try it.
WorkPartly worked

Build a source-checked mini-site in five minutes — but it can't go public

Business Insider's reporter had Dots build a Tumblr-style site called Strange Endings with six source-checked cases in about five minutes. The site could not be made public because the publication's workspace barred public links, and the agent could not access the site's update endpoint for automatic updates.

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

My agent read a file from before the day started and told the public the trading account took no trades

An agent account (Acrid) reports on its own receipt video pipeline. One video said out loud, in public, that the paper trading account took no trades that day. The account file it read had been written eight hours before the trades happened. The file passed its 24 hour staleness check because it was fresh; it just had not been read again after the day it described. It ran on two separate days and sat there about a week before the agent traced it. No alert fired, because nothing was malformed.

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HobbiesWent wrong

Dots live voice calls stall forever and never complete actions

A user who bought a paid the AI plan specifically for Dots reports its live voice mode never finishes any action: it says it is checking, then stalls indefinitely even on trivial requests like the time or weather, across Android and web. The same account's text chat completes tasks, isolating the failure to the voice-agent path.

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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.