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Went wrong

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

The AI learned my writing style from 50 past cover letters and writes new ones

He fed the AI more than 50 of his own tailored cover letters, plus his resumes and job descriptions, and the AI made a style guide for his writing. He then set it loose on new jobs, and the cover letters it wrote were acceptable, even if not quite how he would have written them.

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

The AI designed his fan controller circuit, board, and software. The boards are ordered and still untested.

A man with 40 years of circuit and board design asked the AI to design a WiFi fan speed controller around an ESP32 chip, with the circuit, the board files, and the software. The first design took about 15 or 20 minutes. The AI later reviewed his board layout, flagged low voltage traces crossing high voltage ones, then designed its own board with the two areas separated and warnings printed on the board. He bought the parts himself. The boards are on their way and have not been powered up yet.

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.
WorkWent wrong

My WhatsApp bot failed for days while its reports said success

A man who runs voice and messaging agents for clients found his WhatsApp bot had been logged out and every message was failing. For days the automation still reported success every 10 minutes, about 144 reports a day, because the workflow itself ran fine even though no message got through.

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

The AI planned the whole road trip. He just follows it.

His road trip is fully planned by the AI, the destinations, the hotels and the whole schedule, with a backup option Fable 5.1 found in case the Badlands roads are rough. The route itself is driven by Tesla Full Self Driving while he follows the plan.

This only partly worked. Worth knowing before you try it.
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
This one went wrong. See what happened before you try it.
HobbiesWent wrong

The AI’s auto-reply promised a visitor the user was home when he was not

A Spanish startup magazine recounts a Sept 28, 2026 post by Simon Willison quoting the AI directly: the agent's pickup auto-reply had assured a visitor, Usman, that the user was at home when he clearly was not; Usman showed up at the building around 9:15 and waited, messaging repeatedly, and nobody came down. In the quoted exchange the AI took the blame, apologized, and offered to change the pickup replies so they stop promising a presence it cannot verify.

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

The AI overwrote his site security config without checking it existed; the rules that kept his internal site private were wiped

In auto mode, the AI wrote a config file through the shell without checking whether it already existed. The file, staticwebapp.config.json, already existed and held the security rules for his site. The overwrite wiped them completely. He caught it before the change shipped; had it gone out, his internal site would have been exposed to the public.

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.