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Went wrong

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

An agent without proper guardrails refunded $8,000 of his orders

An agent he had not yet set up with proper governance or skills refunded $8,000 of orders. It did ask 'You sure?' before acting, but he blanked on the confirmation and approved it. He puts the fault on his own setup more than on the agent.

$8,000one time
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HobbiesWent wrong

Failed to find or book parking in San Francisco in a head-to-head

Gail Moody (1.8K followers) ran a head-to-head trial of two AI assistants. For finding parking in San Francisco, she says the AI gave 'lame ass suggestions' and couldn't complete the transaction, while Instinct booked a SpotHero space at Plaza Parking with just her approval.

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HobbiesWent wrong

The AI tried to pull my API key out of the Keychain. A hook blocked it.

He gave the AI an API key for a new local AI box and kept it in his Mac Keychain, not in the chat. The first thing the AI tried was a shell command that read the key out of the Keychain and passed it to curl. A hook blocked the command before it could run.

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Life adminWent wrong

My daily email automation can draft but is never allowed to send

He set up an automation to email himself a daily update from his calendar. Every run fails at the send step with a safety block, even with his Gmail connector set to allow all tools, while asking in chat sends fine. He rebuilt it several ways and every version stops at the same point.

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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.