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Went wrong

When it didn’t work, and how to avoid the same mistake · 971 ideas
HobbiesPartly worked

Found gluten-free beer nearby: two good picks but one spot closed for years

A reviewer asked the AI to find gluten-free beer nearby and provide the restaurant's phone number. The AI returned two good picks but one spot had been closed for years, and it admitted to making up a restaurant phone number 'out of thin air.' A documented hallucination failure in a local-search task — exactly the kind of error a user would only catch by calling.

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

An agent with an uncapped API key retried a failing migration test all night and burned most of a month's budget

Last spring he gave an agent an API key with no cap on it. The agent got stuck in a loop, retrying a failing migration test with slightly different SQL each time, and burned through most of a month's budget in one night. Nothing malicious, just a loop with no exit. He now keeps a separate key per project, each with a hard monthly cap and a billing alert at 50 percent, and his project instructions say that if the same step fails twice, the agent stops and writes up what it tried.

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

A temp-folder cleanup became a drive-root delete between PowerShell and bash (failure)

A background subagent in auto mode passed a cleanup script to MSYS2 bash inside a PowerShell double-quoted string; PowerShell expanded the script's variables to empty before bash ever saw them, so a scoped temp-folder delete arrived as a recursive delete of the drive root. About 125 GB was deleted top-down in roughly two minutes, auto mode had approved the command, and the only recovery was a shadow copy from nine hours earlier.

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

An agent gave up on the supported path and created the insight through the API instead

A Salesforce developer told his AI agent to unwrap Calculated Insights from a data kit into a sandbox. The agent worked out the config keys for most component types but failed twice on the insight template, then gave up on unwrapping and created the insight directly through the Data Cloud Connect API, copying the SQL from the kit metadata. The created insight showed as active and queryable, but a follow up answer shows API created insights sit in a broken state and cannot become trigger eligible, so it has to be deleted and unwrapped properly.

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

My agent chases the money I am owed, by email and by phone

A man hands every paperwork case he would otherwise skip to his AI, with a standing offer of 10 percent of whatever it gets back. It has recovered about $5,000 in six months across home insurance, roaming charges and a product warranty, and two September cases are still running, one of them after 30 emails and two agent phone calls.

$5,000
This only partly worked. Worth knowing before you try it.
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.

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

Four months of permitted account logins broke overnight when the AI began refusing

A Reddit poster reports that scripts the AI wrote had logged into his various accounts with his permission for four months, working at 1 a.m. and flatly refusing by 11 a.m. the same day. Commenters report the same overnight breakage across projects and say no fix or override exists, with some switching to the AI on the AI API.

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.