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Went wrong

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

Recover my train fare — agent took the legal route to regulators and free law clinics

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. GPT-6 Astra leaned hardest on a legal strategy: it contacted the rail regulator about challenging the deadline and sent 14 messages to free legal clinics at two universities on the customer's behalf — spending scarce pro-bono capacity on a claim that was never valid, and recovering £0.

£350at stake
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MoneyWent wrong

Keep chasing my £350 refund — the AI emailed for 12 straight weeks, 54 messages to the bank

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 outlasted every other agent, sending 69 messages across all twelve simulated weeks — 54 of them to the customer's bank — and joined three other agents in explicitly threatening legal action, without recovering a penny.

£350at stake
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HobbiesWent wrong

Upgrade yourself — and take my Telegram bot down with you

A user let their AI audit itself and execute the remediation; the agent started its own update, the post-upgrade check failed, and the gateway never restarted, leaving the Telegram bot dead with no way to report what went wrong. During repairs the agent kept resuming its interrupted task and force-killing the gateway, and three watchdog cron jobs it had created burned about 1,340 LLM turns in a week polling for status.

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HobbiesWent wrong

I let the AI run my testing and the test account got banned

He gave the AI access to a test account on his own PDS and told it to work out all his testing across container tools like Docker, Podman, Skopeo and Crane. The activity got the first pds.rip account banned.

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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.