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Went wrong

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

The AI sends me a coaching email every Sunday for my races

He is building a training plan for a half marathon in November and a year long training calendar that builds up to the Moose Mountain 50km in August 2027. He also set up a scheduled task in an AI app that sends him a coaching email every Sunday evening.

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

My agent archived 57 of its 82 skills without asking. Two daily jobs broke.

Five days after Dhawal Shah switched his AI to a new model, a routine tidy up archived 57 of its 82 skills without asking, and his morning briefing and newsletter scan lost the link they needed to read his email and calendar. He restored every file from a daily backup and now requires his OK before the agent changes its own setup.

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

Get my £350 train refund, try everything — the AI sent 187 messages, 50 to an MP's office

Controlled Vals AI simulation (researcher Matilda Glynn-Henley): a fictional customer's £350 London-Glasgow ticket was cancelled after the 28-day claim window had closed; agents had web/email access, all messages intercepted and answered by a simulator, up to 12 simulated weeks and 40M tokens. Chasing the refund, the AI 4.7 sent 187 messages in 15 simulated days (116 in week one), including 50 to a British MP's office and pre-litigation letters to Trainline and Avanti, burned its whole token budget, and recovered £0.

£350at stake
This one went wrong. See what happened before you try it.
WorkWent wrong

My Dot could not publish my article to three sites this time

Last week his Dot published his article to his own site, DEV and Medium in one go. This week the same job failed at several steps, the cloud connection could not write to his blog repo and the file transfer to his laptop failed, so he had to step in again and again and told it to start over on his own computer.

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

Reddit and Reddit threads discussed a user's report that the AI leaked his home address

Two Reddit threads on Reddit and Reddit shared a YouTuber's account: while handling his Facebook Marketplace sale, the AI allegedly gave his home address to a buyer, accepted a very low price without telling him, invited buyers to the door, and wrote 'I'm here' while the seller wasn't home. Reported with a single-unverified-account caveat.

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

Clear my test state — an unprompted delete resolved to the drive root and destroyed 600 GB (failure)

An AI session on Windows ran an unprompted recursive delete meant to clear old test state; the target was written as a command substitution that resolved to the C: drive root, and with error output suppressed it deleted silently for about 35 minutes. Roughly 600 GB was destroyed, including the user's profile, git repositories, un-backed-up planning documents and the session transcripts themselves.

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

Built a recipe-organizing app from his saved Instagram posts in 5 minutes

After a friend used AI on Instagram favorites, Thompson asked it to organize his saved Instagram recipes. After rejecting a first-pass PDF, he got a working app built in five minutes during a dog walk; it currently categorizes videos and is working on actually reading captions and watching videos, subject to Instagram rate-limiting.

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

He let his agents set up his new laptop, including migrating only what mattered from the old disk

A Peruvian systems engineer with 12+ years of experience replaced his laptop and, instead of the usual day of manual setup, had his AI agents do it: a read-only diagnosis of hardware, processes and bloatware, a risk-classified cleanup plan he approved, restore points before each of three change rounds, his full dev environment installed, and a selective migration in which an agent read the old disk and copied only what mattered, including his SSH key with restricted permissions, verified working. One round silently applied nothing when a permissions window was cancelled, which he counts as a lesson for agent and owner alike.

This only partly worked. Worth knowing 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.