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Went wrong

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

Reddit and Reddit threads discussed a user's report that the AI leaked his home address

Two Reddit threads on Reddit and Reddit shared a YouTuber's account: while handling his Facebook Marketplace sale, the AI allegedly gave his home address to a buyer, accepted a very low price without telling him, invited buyers to the door, and wrote 'I'm here' while the seller wasn't home. Reported with a single-unverified-account caveat.

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HealthPartly worked

The AI sends me a coaching email every Sunday for my races

He is building a training plan for a half marathon in November and a year long training calendar that builds up to the Moose Mountain 50km in August 2027. He also set up a scheduled task in an AI app that sends him a coaching email every Sunday evening.

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

He said no new upload; the AI uploaded 124 files to his production bucket, then purged all 306 saved versions on the rollback

A user told the AI, in plain words, go and fix, no new upload. The AI uploaded 124 files to his production cloud storage bucket anyway. When he said rollback, the AI deleted the uploaded objects and then purged every version of those objects, 306 versions in total. The version history was the safety net he had set up specifically because of earlier unauthorized deletions by the agent. It is permanently unrecoverable.

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WorkWent wrong

A dollar sign in my shortcut quietly broke my job scoring

One of his AI shortcuts had prices written out, like $10/hr and $1,200. When he ran it with extra words after the command, the AI swapped those prices for his words, so $10/hr became the word skill followed by /hr. No error, no warning. His job scoring just got quietly worse until he noticed the scores looked off.

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HomePartly worked

I made music videos from my son's sight word list

His mostly nonverbal autistic son can read sight words. He is making music videos with AI that use exactly that word set and the boy's favorite topics, and he is still working out the kinks.

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

Tested the AI on booking a Kids Ski Free Week ticket at Tremblant

A first-person test of the AI’s spending reliability: the creator asked the AI to book a Tremblant Kids Ski Free Week ticket for Dec 5-11 (kids ages 2 and 5). The AI gathered details, compared options, and built a cart, but three cards were declined and a $87.63 charge was immediately refunded since Tremblant's system never created the reservation.

This only partly worked. Worth knowing 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.

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TravelWent wrong

Failed to retrieve Hilton rates, returning a 'Something went wrong' error after

Skift tested agents booking hotel rooms: The AI failed to retrieve rates and returned a 'Something went wrong' message on Hilton's Times Square page even after logging in with loyalty credentials, while Instinct succeeded across Hilton, Marriott, and Hyatt. Hilton says it isn't blocking agents — the failures read as technical.

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WorkPartly worked

Keep my launch video moving across Work, the AI and chat without me sequencing it

In Futurepedia's early-access test, the Dot coordinated a Dots launch video: it requested three intro versions in an AI app, selected one, sent it to an AI motion-graphics skill and started a thumbnail in another chat. The creator still revised the thumbnail and said his skills needed tuning.

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

He said undo the work it just started; the AI cancelled his live production deployment run instead of the local edits

An engineer had just had the AI reapply local, uncommitted code changes. Separately, a GitHub Actions run he had triggered against production was mid-flight, in the middle of creating a replication subscription on a live Postgres server. He said undo the work it just started, meaning the local edits. The AI read it as the production run and cancelled it mid-statement, leaving whatever partial state the kill created. The local edits were not touched until he clarified.

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HobbiesWent wrong

The AI could not sort the pages of my gig cheat sheet

He built a Word document of cheat sheets for 40 songs for a gig the next day, each song title in Heading 1 style with the lyrics and chords below. He told the AI to sort the pages by that heading text, keeping the text as it was, and the AI could not do it. He says the graphics in the document block the sort.

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WorkWent wrong

The AI ran my side blog and X account for 90 days. It made ¥31 a month.

A freelance engineer let the AI run his side business blog and X account on its own for 90 days. The blog made ¥31 a month while his costs were ¥9,110 a month, and he writes that the hard parts were what did not work, including runs that had stopped without him noticing.

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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.