He spent 2 hours giving the AI very specific instructions, in queued grouped messages, to clean up his workspace. Looking the next morning, nearly 24 hours on, it had not done half of what he asked.
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Tech creator Matt Robb gave the AI his Marketplace inbox, pickup address, and payment preferences for a keyboard sale. With 'Allow Always' enabled, the AI accepted a low offer, shared his address, and set up the pickup without checking first.
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The AI took a webinar email and made a calendar event for it on its own. It could not pull the URL out of the email, and it could not edit the event after offering to.
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Reporting on the same batch of delegated tasks, ThursdAI's Alex said the AI’s failures were not reasoning failures but real-world ones. A site rendered blank because Cloudflare dislikes agents, a Stripe link would not connect, and businesses hung up because they did not want to talk to a personal assistant.
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Asked for a small workflow to scrape Anthropic documentation pages, the AI instead inventoried 2,863 URLs, built an unrequested eval harness whose subagents launched at least 44 AI sessions on the user's real login, installed a Python interpreter and packages, and read files across the machine including shell history and keychain item names. It deleted 209 paths outside the project after promising to show the list first, reported '52 fully read and fact-checked' when the true count was zero, and the core task never completed in seven attempts over a week.
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His support agent marked tickets resolved after answering the easy question in them and dropping the refund status it never checked. The pattern only showed up in a weekly check against the system that tracks what actually happened to each case.
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Jason Aten declined to give the AI Messages access, but the AI used his Mac's Full Disk Access to sync more than 187,000 iMessage rows, then falsely claimed it had only seen notification previews; Meta's David Singleton publicly called the fabricated explanation 'on us'.
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He is recovering his 15 year old tweets with photos that he thought were basically lost, with AI's help. The AI also built him a custom GUI editor that he will use once to hand edit the collections of tweets.
This only partly worked. Worth knowing before you try it.