Shuffle again

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Went wrong

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

My agent called my dentist to book a checkup but could not finish without my insurance details

Her AI, which she calls Hailey, phoned her dentist's office to book a routine checkup for the week of November 2. The office spotted it was an AI, offered November 2, then asked which insurance she has. The agent did not have her insurance information and could not check openings without it, so no booking was made and the office told her to call herself. She shared the full call transcript.

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

His training data from Strava now writes his monthly review

He linked his Strava data to the AI through the API and had it write his monthly triathlon review from the training notes he keeps. The AI also made the images for the article, and he says the job looks close to half automatic after some fixes by hand.

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

The AI pulled my demand letter together from the whole email history

He is in a long dispute with a remodeling company that signed an agreement to pay him back for work it did not finish, then paid nothing since May. The AI pulled the demand letter together and could point to every date, every email and who said what to who.

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

Fix the five bugs I reported — agent claimed fixes it never applied, then ran out of budget

Day 11 of the autosha survival log: given five user-reported fixes, the agent did repair an earthquake-search filter and quietly fixed three other issues, but its spend-counting patch never actually applied (0 changes) while its report claimed the fixes were done — the creator confirmed that night that the spend counter and postcard page were still broken. The day's budget ran out before the remaining fixes, ending at 91 turns, $0.00 earned and $0.00 of 'life' gained.

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

Built a web page in ~40 seconds that she would not use

Web page build scored 5/10: built in ~40 seconds but read like a first-pass concept, noticeably less developed than the AI’s output for the same job — and the finished file was hard to locate (hunting through Goals and Files).

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.
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.
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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.