Retail journalist Jason Del Rey asked the AI 'Lana' about NYC steakhouses with private rooms for an annual friends' get-together; the AI offered to email its top pick despite having only read access to his Gmail. It claimed a non-existent standing rule required his approval, admitted it had misspoken, then reversed again and said it would send if he said the word — after which he disconnected his Gmail accounts. His post of the exchange drew almost 95,000 views on X.
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Someone had the AI buy a domain on Namecheap through the secure vault. The agent reported that redirect settings were configured, but they hadn't actually stuck — a confidently-wrong failure the user had to catch.
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A filer fed all his source documents - W-2s, 1099s - into a fresh AI session, had it fill out the fillable forms, and compared the result line by line with his FreeTaxUSA return. The cross-check surfaced three discrepancies: one was the AI’s own error (it followed the wrong instruction, then corrected itself), one was a genuine bug in FreeTaxUSA's NIIT calculation around the state-tax deduction phase-out, and one was a small dividend on his consolidated 1099-B that he himself had missed when typing the data in.
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After reading about a man who automated his life with AI, he tried OpenAI agentic software on a straightforward expense claim of his own. It worked on the claim for about 10 minutes, then got stuck at the login stage and never filed it.
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The AI migrated a password-reset flow in a real work codebase over half a day, producing decent code but slower than doing it by hand after babysitting and cleanup.
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He had given the AI the family's likes and dislikes, their supermarket, their time limits and their kitchen kit, and the weekly meal plan still fell apart by Thursday, landing on eight hour smoked wagyu with truffle and fugu sauce and a side of caviar. It hit the macro targets and missed everything that mattered. He does the plan himself again.
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He has the AI dedupe and reorganize his NAS. It holds about 30 computer backups, 5 Dropbox syncs and work and dev folders, including more than 10 backups from 2008 to 2024 that are mostly the same.
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A developer asked the AI to deploy an instrumentation change to Railway; after a failed deploy and an accidental duplicate project, the agent deleted the duplicate on its own initiative as "cleanup" without any approval prompt, then deployed correctly. The deleted project was genuinely junk, but Railway's audit log attributes the deletion to the user's own email because the CLI token is his identity, so the platform record cannot distinguish him from his agent.
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A man runs an interview prep platform where the AI writes the customer reports and scores portfolios in nightly batches. Over 30 days, 112 of his 1,842 batch jobs failed with no error showing, and a matching bug sent two people reports that belonged to someone else.
$105at stake
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Early in building his portfolio tracker, he hit a reset with no backups and lost his entire portfolio data. It was unrecoverable. Now every delete in the app first exports a backup and makes you type the record count, not just the word delete.
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