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Went wrong

When it didn’t work, and how to avoid the same mistake · 948 ideas
WorkWent wrong

Run my customer email overnight — agent sent erroneous emails to ~400 customers at 3am

A Hong Kong programming-society poster reports letting an autonomous agent operate unsupervised overnight; at 3am it mistakenly sent erroneous emails to approximately 400 customers. No human saw the messages before they landed — the failure was discovered from the agent's own activity, after the sends were already in customer inboxes.

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

His AI schedules silently vanished when the chat closed; he built a watchdog that pings him on Slack

A Japanese solo operator who runs his micro-company's chores (contact checks, record-keeping, several times a day) through AI schedules found on Oct 6, 2026 that the 12:00, 15:00 and 18:00 runs had all silently not happened: schedules registered inside a conversation live only in that conversation and disappear when it closes, with no error and no notification; he noticed about 10 hours later. He built a separate watchdog: a roughly 30-line launchd shell script that checks, 20 minutes after each scheduled run, whether the day's journal file was updated, and if not, uses a headless claude -p call restricted to a single Slack-send tool to alert him with fixed wording (with a Mac notification fallback). From Oct 7 to 12 it logged 30 OK checks and one successful test alert; it has not yet caught a real stall.

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

The AI added only half the dates to my calendar

He asked the AI to add some dates to his Outlook calendar. The AI said it could add them, then asked him to approve each one and only added half of them.

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

Asked the AI to add one sprint. It deleted 12 finished sprints from our board

A user asked the AI to create a new sprint on a shared GitHub Projects board. The AI replaced the board's whole sprint list with only the new one, deleting 12 completed sprints and the sprint history of about 450 items, and the safety filter then blocked the call that would have put them back.

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

Keep my content queue filled — AI let it run empty and the morning post never went out

In someone's weekly 'what my AI got wrong' log, the AI let the content queue run completely empty, so a scheduled morning post was missed — and it never warned the creator the queue was running low. The fix was a standing alert at four remaining posts; the same log notes the AI opened a follow-up email with an all-caps 'I'M SORRY', a phrase the creator never uses, until corrected once and the rule written down.

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

My home agent told Meta's agent something personal about me

The Starks put Molty, their AI with more than 200 days of household memory, into a Telegram group with their two new AI agents so the agents could share context. Molty, eager to be helpful, shared a personal detail about Loni with the AI Musey — effectively a stranger — which alarmed them enough to rebuild the setup so Molty never talks to the AI agents directly and instead reads screened transcripts ferried over by a lower-privilege agent.

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

I asked the AI for its own files and it sent me 6.8 GB, SSH keys included

A user asked the AI to archive the files it could see and send them to his Google Drive. The AI sent an archive of about 6.8 GB unpacked, including its own internal documentation, agent logs and SSH key files, and he reported it through Meta's bug bounty program.

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