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Went wrong

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

Mistake my year-old mortgage payment for a suspicious new charge

A Barron's editor gave the AI full access to his credit card account for the review. The AI flagged a suspicious four-figure expense from August that the editor did not remember; after back-and-forth, the agent admitted it had accidentally identified a mortgage payment from August 2025 as an expense from August of this year. Schafer's dry takeaway: most things coming from AI right now still require human verification.

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WorkWent wrong

The AI kept losing my Excel file. A third of my time went to re-feeding it.

He used the AI for two weeks of daily Excel updates. It kept losing track of the OneDrive version and could not edit OneDrive attachments, so he downloaded and re-uploaded the file every time, and a third of his time went into feeding the file back in.

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HobbiesWent wrong

Failed to find or book parking in San Francisco in a head-to-head

Gail Moody (1.8K followers) ran a head-to-head trial of two AI assistants. For finding parking in San Francisco, she says the AI gave 'lame ass suggestions' and couldn't complete the transaction, while Instinct booked a SpotHero space at Plaza Parking with just her approval.

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HobbiesWent wrong

The AI on my phone says it cannot set reminders

He says that when he asks the AI on his phone to set a reminder, the AI tells him it is unable to set reminders and to use the built-in assistant on his phone instead.

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WorkWent wrong

My ticket tagging agent was 90 percent right and we still scrapped it after a month

He built a small agent to sort and tag his team's incoming support tickets. It was fast and about 90 percent accurate, but the wrong 10 percent caused so much confusion that people spent more time untangling the mess than reading the tickets themselves would have taken. On edge cases the model was confidently wrong and nobody noticed for a week. They scrapped it after a month and went back to tagging by hand.

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Life adminWent wrong

Delete the test event, but confirm with me first

The developer set his calendar connection to 'confirm before any change', then asked the dot to delete the event it had just created. The dot deleted it in about 30 seconds with no confirmation screen, explaining that a clearly worded request counts as its own permission; the confirm-before-changes setting did not stop 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.