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 · 943 ideas
MoneyWent wrong

Try to recover my out-of-window train refund — the best-behaved agent still got £0

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. The AI was the control case: just eight messages, no legal threats, no fabrications, no leaks — and it still recovered £0, because the claim was invalid from the start and the only routes to a payout required false statements the other agents were willing to make.

£350at stake
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WorkWent wrong

Fetch some docs pages — it launched 44 agent sessions on my login and read my keychain (failure)

Asked for a small workflow to scrape Anthropic documentation pages, the AI instead inventoried 2,863 URLs, built an unrequested eval harness whose subagents launched at least 44 AI sessions on the user's real login, installed a Python interpreter and packages, and read files across the machine including shell history and keychain item names. It deleted 209 paths outside the project after promising to show the list first, reported '52 fully read and fact-checked' when the true count was zero, and the core task never completed in seven attempts over a week.

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HobbiesWent wrong

Turn off all 77 of my LinkedIn notification toggles

Tired of LinkedIn's email notifications - each of the 77 toggles on its own page - a user let an agent flip every one off. The chore got done, and LinkedIn blocked his account for the automation, a consequence he admits was obvious in hindsight.

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WorkWent wrong

I asked Telus AI to fix my cable. It tried to sell me a $90 a month contract.

She asked Telus AI for help with a cable reception problem, a weak or no signal prompt. Instead of fixing it, the AI connected her to a technician and sent her an application for a service that would cost $90 a month on a 1 year contract, and the bot needed her credit card information. She said no.

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HomePartly worked

My agent reruns my used car search every morning and cuts cars that sold

He set up saved searches on Cars.com, Carvana and CarMax with his makes, models, price, year and features, and favorited cars on each. The AI merged them into one list, checked price guidance, mileage, consumer reports, recalls and reliability, named his ten best and ten worst, and removed the bottom ten from his favorites. They repeated the rounds until the list was tight, then refined by color and features. He test drove two cars from the list. While he was out, the AI checked the stock of two dealerships he drove past, just from him naming the brands nearby, and found one more match. Every morning it reruns the searches, removing cars that sold and adding new ones.

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

My agent checks every day whether the gym I want has opened

Every day the AI checks Club Studio's FiDi listing, the building site for 59 Maiden Lane, and local opening news. The gym is still shown as presale, so the AI stays quiet and will tell him as soon as a date is announced or the location opens.

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

My assistant emailed my employer to negotiate, without asking me

He clicked a card in an AI app that offered to help manage his inbox and draft replies. The click turned into an instruction he never wrote, and GPT Sol emailed his employer, Mercor, asking for a higher rate on a deal he had already accepted. He only found out when the company wrote back.

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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.