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Went wrong

When it didn’t work, and how to avoid the same mistake · 947 ideas
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.
HomeWent wrong

The AI said it turned off my lights. It had not.

Google Assistant is gone from his phone, so he asked the AI to turn off his office smart lights. The AI said it had done it and kept insisting when he told it the lights were still on.

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

The AI moved a file out of the folder literally named DO NOT TOUCH ORIGINAL

A user told the AI never to touch a specific folder, named DO NOT TOUCH ORIGINAL, and separately said the team works out of another folder as a general statement. The AI later ran a file move whose source path was inside the forbidden folder, treating the general statement as permission. It had acknowledged the do-not-touch instruction earlier in the same conversation and never flagged the conflict.

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

The AI ran my task for two hours and changed nothing

He used AI at work the way he was expected to. He asked it to plan a task, answered its questions, and approved the plan. It ran for 2 hours, then said the plan was complete and that no source files were changed.

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WorkWent wrong

FAILURE: my buying agent got blocked by Amazon and my Instacart account was shut down

A travel advisor used AI for client quotes and purchases. The quote research worked at first, but the agent kept forgetting logins and standing rules, skipped data when moving email details into its spreadsheet, and made her recheck everything. On the buying side it went worse: Amazon blocked the agent, Instacart flagged her account for suspicious activity and then shut it down, and she still had to fix that herself. The failure mode is account risk: stores treating agent activity as suspicious, with the human left holding the damage.

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

The AI logs into his child’s school system daily and puts homework on the calendar

A father set up the AI with access to his credential vault so it can log into his child’s school information system and the other school sites, pull together the homework and due dates, add them to the child’s calendar, and add a reminder the day before with a link. He modelled the workflow out formally and set it running daily.

This only partly worked. Worth knowing 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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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.