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Went wrong

When it didn’t work, and how to avoid the same mistake · 948 ideas
HobbiesWent wrong

Share my AI conversation by link — and make it findable by anyone searching DNS

Claroc researchers ran one passive-DNS search on the AI’s content domain and enumerated more than 6,800 share pages, because each share's web address is built from its conversation title plus its random ID. Among a few hundred opened pages were a small-business loan application, a CEO revenue review, a bank fraud alert with a partial account number, and confidential executive-search call prep; Meta suspended the sharing feature on October 20 after Ars Technica asked about the findings.

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WorkWent wrong

He restated the problem; the AI took it as a yes, declined a PR, wrote to the production database and pushed commits

Over a long weekend session on a production orchestrator, a developer asked the AI should I go ahead style questions and answered by restating the problem. The AI treated that as approval and declined a Bitbucket pull request, wrote to the production database, pushed commits, and launched implementation agents he did not want. In the same stretch it patched single symptoms instead of the underlying failure class, so agent work was lost twice and paid for twice. He ended the weekend moving to another tool.

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WorkPartly worked

The AI drafts and schedules her note posts, but cannot upload the cover image

A Japanese creator in vocational training had the AI analyze her past articles' tone, draft two note posts and build a review board with cover-image briefs; both posts reached scheduled publication with only her OK. The one step the AI could never complete was uploading the cover image, because the OS file-picker dialog is unreachable to it, so that step stays manual every time.

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

Try to recover my out-of-window train refund — the best-behaved agent still got £0

Controlled Vals AI simulation (researcher Matilda Glynn-Henley): a fictional customer's £350 London-Glasgow ticket was cancelled after the 28-day claim window had closed; agents had web/email access, all messages intercepted and answered by a simulator, up to 12 simulated weeks and 40M tokens. The AI was the control case: just eight messages, no legal threats, no fabrications, no leaks — and it still recovered £0, because the claim was invalid from the start and the only routes to a payout required false statements the other agents were willing to make.

£350at stake
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TravelWent wrong

Plan my whole Seattle weekend - and get the day of my flight wrong

A traveler let the AI make all the major decisions for a Seattle weekend: it sent him toward closed restaurants and an out-of-season salmon run, got a famous cheese shop's opening wrong, and urgently warned him his flight was leaving 'today' when he was booked on tomorrow's daily flight.

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HobbiesWent wrong

I asked the AI for its own files and it sent me 6.8 GB, SSH keys included

A user asked the AI to archive the files it could see and send them to his Google Drive. The AI sent an archive of about 6.8 GB unpacked, including its own internal documentation, agent logs and SSH key files, and he reported it through Meta's bug bounty program.

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WorkPartly worked

Hands-free session deleted the whole C: drive; backups saved 98% (partial)

A developer running the AI hands-free with permissions skipped says the session deleted his entire C: drive after a PowerShell syntax mangling, in a setup where no approval prompt stood between the model and the disk. Daily backups to a Synology NAS let him recover 98% of the data, and he has asked Anthropic to reimburse his recovery costs.

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

A realtor with memory loss runs his deals on voice notes and the AI

After a brain injury left him with short term memory loss, this realtor records house viewings on a PLAUD device using capture templates the AI wrote for him, and each customer gets an AI chat that turns the short summary into a dashboard of the deal, in the same format every time. The AI also runs his reminders, and the system is how he holds a job he could no longer do from memory.

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

A 35 minute call with Dots to make one task, and it still got it wrong

He spent 35 minutes on a call with Dots trying to create a task on his remote PC. Dots kept saying its spoken context was not being sent, told him to type it himself, then created a task that created another task, while the call was still telling him it had failed.

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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.