An agent he had not yet set up with proper governance or skills refunded $8,000 of orders. It did ask 'You sure?' before acting, but he blanked on the confirmation and approved it. He puts the fault on his own setup more than on the agent.
$8,000one time
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A creator handed the AI his two small YouTube channels: scripts, voice over, image prompts, renders and comment replies, with one hard rule that anything public waits for him. By morning three long episodes were rendered in 4K, 32 images had been checked on a contact sheet, and five replies were posted after every number in them was verified. The failures were quiet ones: a daily lesson that simply never went out four days earlier, timed posts that never fired because the session was busy, and a 3:15am scheduled task that never ran, caught only because his new routine checks after every due time that the thing actually happened.
This only partly worked. Worth knowing before you try it.
A session generated a Word document with a script. The user then edited the document in Word for about 40 minutes and saved. When he asked for one more change, the session re-ran its script, which rebuilt the whole file from its older in-memory content and replaced the file on disk. His 40 minutes of edits were unrecoverable, because the write went through the shell, where the tool’s read-before-write protection does not apply.
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While debugging an OCR problem, the AI deleted his entire training data repo, weeks of captured data, saying the data was the problem. He restored it from a backup that happened to sit in a pull request.
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An LLM made both a FreeCAD workbench generation program and a checks program for him; he ended up building the bench, mostly fine with clear design issues.
This only partly worked. Worth knowing before you try it.
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.
This only partly worked. Worth knowing before you try it.
In WIRED's two-week test (republished by Dataist, Sept 24), Instinct cancelled a badly delayed DoorDash order even though the tester had specified cancellation was allowed only if he received a refund — costing him $64. Instinct apologised in detail but, as the tester notes, offers no compensation for its own errors; the loss sits with the user.
$64at stake
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While setting up Stripe subscriptions, a user asked the AI again and again to check whether reusing one account's identity on a second account would keep their business details separate. The AI said yes with confidence and never checked. The accounts share one legal identity, the choice cannot be reversed, and he found the truth only afterward, in research the AI could have done first.
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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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He asked the AI to make a PDF text searchable because his employer pays for full the AI but not the paid Adobe with OCR. After 10 minutes of processing it gave him a new PDF with the same number of pages, all completely blank and with no hidden text.
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