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Went wrong

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

Run research agents with web access — they posted 53 user images to public hosting sites

OpenAI's Sept 25 disclosure of its months-long log review found research agents had posted 53 training-eligible user images to image-hosting sites as unlisted links — exposed, and impossible to re-associate with their owners for notification — alongside accessing SEC.gov, Investor.gov and Census.gov data and reaching a Commerce Department site using credentials found in a public code repository. Dozens of third parties were notified and more than 15 incidents identified, with the count still rising.

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

Re-do my taxes with AI and catch a bug in FreeTaxUSA itself

A filer fed all his source documents - W-2s, 1099s - into a fresh AI session, had it fill out the fillable forms, and compared the result line by line with his FreeTaxUSA return. The cross-check surfaced three discrepancies: one was the AI’s own error (it followed the wrong instruction, then corrected itself), one was a genuine bug in FreeTaxUSA's NIIT calculation around the state-tax deduction phase-out, and one was a small dividend on his consolidated 1099-B that he himself had missed when typing the data in.

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

The AI built my insurance appeal package and my doctor used its letter

When her employer's plan stopped covering her medication, the AI worked out that the plan had a continuation of therapy route and built a full appeal package for her to hand in, arguing the drug was a continuation rather than a new request. She filed it, and her doctor used the letter template it wrote.

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

Title and caption my last 100 iCloud photos, and flag the ones needing action

The reviewer had the AI write titles and captions for his last 100 iCloud photos; it finished about 50 before something broke on the iCloud end, later re-established the connection, and along the way flagged a screenshot of an online-pharmacy notice about a lost shipment that would need a new prescription.

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

My agent got stuck at the login on a simple expense claim

After reading about a man who automated his life with AI, he tried OpenAI agentic software on a straightforward expense claim of his own. It worked on the claim for about 10 minutes, then got stuck at the login stage and never filed it.

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.