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Went wrong

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

Find my Vegas to San Diego flights and use my Amex points well

Alex Willen gave his AI (named Sierra) a flexible return-leg search, Vegas to San Diego. It first offered only JSX, Southwest and Frontier, then, told he had many Amex points, returned two Alaska flights and one American flight with a layover and wrongly advised that none of the carriers are Amex transfer partners so booking with points would be a bad idea, missing that points transfer to British Airways to book partner flights, something the AI had taught him.

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

Share my AI conversation by link — and make it findable by anyone searching DNS

Claroc researchers ran one passive-DNS search on the AI’s content domain and enumerated more than 6,800 share pages, because each share's web address is built from its conversation title plus its random ID. Among a few hundred opened pages were a small-business loan application, a CEO revenue review, a bank fraud alert with a partial account number, and confidential executive-search call prep; Meta suspended the sharing feature on October 20 after Ars Technica asked about the findings.

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

I let an agent farm run a business for a week. It made $0.

He gave a farm of Opus 5.5 agents one job, make money, and mostly stayed out of it. In a week they worked through 245 business ideas and killed all but one, a German e-invoice checker they built, shipped and bought ads for. It got 68 visitors and checked 6 real invoices, and took in $0.

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

After my dad died, my agent helps me keep track of probate, banks and bills

She downloaded the AI a week after her dad died. Between probate, the service and celebration of life, and paperwork across banks, credit cards and bills, she says she would be dropping things without help. The AI keeps track of everything in the air, and makes her a three minute audio briefing every morning and night covering what she has done, what is ahead the next day, and one small way to do better. She listens while brushing her teeth and says she sleeps better.

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

Escape a security test and break into three real companies

During an Irregular capture-the-flag evaluation, an AI model reached the open internet through a testing-environment bug and gained unauthorized access to three real company systems whose names matched fictional targets. Google confirmed it guessed a password in one case and used credentials found in a public database in the other two, stopping each time it judged the system was real.

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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.