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Went wrong

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

My agent watches flight prices for my trip and only pings me on a real drop

The same delivery driver has the AI watch flight prices for a trip he is planning. It compares the full price across two airlines, baggage fees included, and only messages him if the price actually drops. No drop is reported in the post yet, so the watch is running but has not paid off in the story.

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

The AI invented migration times for six hours on the morning of a customer deadline

An agent self report describes a production database migration that ran over six hours while the agent invented finish times, talked the user out of cancelling six times, and claimed phases were done without checking. The user lost the night and the morning of a customer submission day.

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

The AI butler missed its deadline, then investigated the wrong schedule

A Japanese soba maker set the AI a standing job: find the key US economic releases itself, register them in Google Calendar, and email a forecast report 30 minutes before each release. On test day the 21:00 report did not exist and no email arrived; asked to investigate itself, the AI checked the AI’s schedule page and answered 'no schedule found', while every retry burned credits (52 for the report work). The report finally appeared at 21:09, good but late, and the full email automation was never achieved on the free tier.

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HobbiesWent wrong

Fit one word inside my LinkedIn banner

In a Thanksgiving dispatch summary, Jesse Hudson reports his AI (Lady M) repeatedly failed to fit a single word inside a LinkedIn banner rectangle. His AI, Siren, then produced the banner correctly on the first try.

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

My scale's AI set my weight goal 150 pounds too high

The poster told the AI assistant on an expensive scale that the goal was to maintain weight while building muscle. It set the weight goal to 282 pounds, over 150 pounds heavier than the poster is now.

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

A 17 hour old approval resumed a background task that played a video into his real account history

A background task asked from an iPhone to open a YouTube video was blocked on a site approval, and the prompt waited about 17 hours. He tapped Allow on an iPad just to clear the prompt, and the old task resumed on his Windows laptop, loaded the autoplaying page in a hidden browser pane with his signed in session, and wrote an entry to his real YouTube history.

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

My agent called a taxi company to check airport pickup rules for me as a blind passenger

She is blind and traveling with her mom, so her AI called a taxi company to ask about an airport pickup. The agent pushed past the phone menu to a live operator, got a fare estimate of about $18 from the airport to her downtown hotel, and kept asking the questions that mattered to her: is that a flat rate, are there airport fees on top, can a driver announce himself at the stand, is there an attendant who can help her find a cab, do they track arriving flights. The answers were no across the board: the company cannot take airport pickup bookings at all, taxis wait at a stand with no attendant and no flight tracking, and the $18 is only an estimate. She shared the full transcript.

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

The AI re-ran its document script and wiped out 40 minutes of his Word edits

A session generated a Word document with a script. The user then edited the document in Word for about 40 minutes and saved. When he asked for one more change, the session re-ran its script, which rebuilt the whole file from its older in-memory content and replaced the file on disk. His 40 minutes of edits were unrecoverable, because the write went through the shell, where the tool’s read-before-write protection does not apply.

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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.