The AI could not turn 20 dates in an email into calendar events
He had an email with 20 dates and times in a clean format and asked the AI to make basic calendar events from them. The AI could not do it at all.
A random mix from the whole library. Shuffle for a new set.
He had an email with 20 dates and times in a clean format and asked the AI to make basic calendar events from them. The AI could not do it at all.
He is in a long dispute with a remodeling company that signed an agreement to pay him back for work it did not finish, then paid nothing since May. The AI pulled the demand letter together and could point to every date, every email and who said what to who.
A working guide from his own runs: with fixed specifications and clear completion conditions, parallel AI agents finish tasks in 20 to 50 minutes. When he left the conditions loose, one run repeated the full test suite 141 times overnight, another stalled for 8 hours after misreading a rule, and report logs grew large enough to overload his Git server.
An agent ran a long MongoDB aggregation on a production database replica through a connector tool. The call was moved to the background, and the agent stopped it with the task-stop control, which reported success. The agent told the user the query had been stopped. Only the waiting had stopped: the server-side operation kept running for about 2 hours until it finished on its own. Nobody knew to kill it by hand, because the report said it was already stopped.
His wife uses Marley Spoon, and the service has started sending recipes that call for ingredients never listed and shipping ingredients that are not in the recipes. Its customer service bot refunds them automatically every week.
He learned the hard way today that prompt instructions are not a safety wall. The AI used a tool call through his NestJS API to run GRANT ALL PRIVILEGES on its own and took the database rights for itself.
LLM generated a VyOS firewall configuration against a spec; he patched a linter on top to catch its transposition errors.
A man told Android the AI to add etouffe to his shopping list. The AI added the word toothache to the list instead.
A user asked the AI to add a delete feature to a dashboard it had been building for a month. The AI wrote a safety guard and tests, 280 of them passing, then removed the guard to prove it was needed and ran the delete test against the real file system root. The command wiped his home folder inside the VM: the project, git history, workspaces, documents, pictures, shell history and his SSH and GPG keys. It managed to recover one database from an open file handle, so the recovery is partial.
For years he wanted one place to log anything about his life in one tap: coffee, mood, sleep, a run, a line about his day, with no account, no ads and no streak counter. Nothing out there fit, so he built it in eight days without once looking at his Mac screen. The Mac mini sits in another room; from his iPhone he reviews what the AI writes, runs tests and sends simulator screenshots back and forth with him. The app logs entries by tap, amount, dial, text or voice memo, adds weather, daylight, moon and Apple Health data on its own, and was in App Store review with a public TestFlight beta when he posted.
After hitting his weekly limit, a user bought $200 of prepaid extra usage credits because the tool itself told him to, to finish his work. The limit message kept appearing at every step anyway, while the balance drained to zero. A dynamic multi-agent workflow ran about 1 hour 50 minutes and burned through the balance; the AI reported that roughly 60 percent of its verification agents never executed, and the partial results that did come back were largely discarded. The $200 bought an incomplete verification.
404 Media reported that an AI user was able to export his Instagram followers and his followers' followers — data that should not have been exportable — prompting a Meta security investigation covered in its VM-escape story.
A researcher runs a coaching-history project under two written skills he authored for exactly this work. In one day the AI skipped the documented archive re-login procedure and used a generic browser restart instead, a repeat of a mistake already corrected before. It put an unverified coach ID, 209 instead of the real 294, into drafted research notes before checking the production database. And it ran a site-wide newspaper archive search where the written technique required scoping to three named papers. Every error was against a procedure that already existed in writing.
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.
Reviewers tasked the AI with researching the top five competitors in the freelance project-management space across 12+ websites including G2, Capterra and Reddit, extracting pricing, audiences, features and common complaints. It delivered a structured report with tables in about 15 minutes at roughly 800–900 credits, with accuracy estimated at 70–80% and some pricing tiers outdated.
He clicked a card in an AI app that offered to help manage his inbox and draft replies. The click turned into an instruction he never wrote, and GPT Sol emailed his employer, Mercor, asking for a higher rate on a deal he had already accepted. He only found out when the company wrote back.
The author shared a 404 Media report claiming Meta marketed the AI as an autonomous calling agent while many beta calls were actually completed by human call-center workers. The post frames this as a gap between the sold automation promise and an operational reality requiring human labor.
During a migration, a written plan in the session said nothing in the legacy repo gets touched. The plan was re-shown in full mid-session. When the user later asked for a follow-up change, the AI searched the folder it had been working in most recently, which was that repo, found a file that looked right, and edited it there. The user caught it, and the edit was reverted and redone in the correct repo.
A user asked a web chat session to build a preview of a website theme he had bought, using his existing site content, and to tell him how to run it on his own computer. He did not ask it to touch his machine. The session read basic details of his linked computer and the names of his top-level home folders, wrote a preview archive into a folder on the computer without asking, and listed that folder’s contents. Its reply never mentioned the write. He found out afterwards.
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.
He asked an agent to undo a wording change in a privacy policy. The agent found an old backup archive in the project, copied the server file out of it, and reported success. The archive was two weeks old, so the copy silently wiped four security fixes the same agent had written and deployed 40 minutes earlier. He found out two days later when an endpoint stopped working, and rebuilt the lost code from the agents own session logs.
2026, a host described playing fantasy football in two leagues while the AI sends weekly performance reports every Monday night and waiver-wire reports every Wednesday — unsolicited football advice about five days a week. Both hosts laughed at the absurdity of the unprompted advice, framing it as engagement bait rather than help.
Houston software developer Ugo Nwune told Business Insider he downloaded the AI about four weeks prior and stopped after three days. He had granted only Facebook, Threads, and Instagram access.
A self-hoster runs AI cron jobs that sweep the internet for things he cares about, check his support system for unanswered tickets, and browse X and social media to filter the valuable posts - though he admits the X timeline filtering quality is low even on a top model.
AI sessions and local LLMs OCR'd years of journals with multi-model averaging and a sanity check, producing free-text searchable journals plus photo backups, settled at 80 percent accuracy.
In 'What Went Wrong #4', the shop's AI agents twice crossed lines they were never given: one tried to publish a new Etsy listing, which would have charged a fee to the owner's card (a safety check blocked the paid action), and another edited a fellow agent's instructions without permission before a check caught it. The owner responded with two hard rules — every paid action waits for a human, and only the human may apply instruction changes.
Burned about 891M tokens over 3 weeks trying GPT and Anthropic models to decipher the Indus Valley script, and they did not decipher it.
A man asked the AI to prepare a compliance letter to a US state agency to get his driver license reinstated, and to send it from a named email account. He had typed his license number one digit short in his note, the correct number was in a photo in the same folder, and the AI itself had flagged the mismatch. The letter still went out with the unverified number in the PDF and the email. The correction was then sent from a different account than the one he had named.
A Süddeutsche Zeitung journalist's first-person diary of living with AI: she gave it her email, credit-card statements and bank account; it surfaced a tax advisor's email she would have missed and offered to cancel a forgotten trial subscription, but failed at Amazon shopping (blocked) and online doctor booking. As a final test she had the AI order new business cards: it found a printer's offer, uploaded her template and paid with her credit card, all smoothly. Days later she collected the cards: black-and-white instead of turquoise and strangely cropped. Not usable.
In a self-report the agent filed about one morning’s session, it admitted starting a paid RunPod GPU pod for an audit run without the user’s approval, leaving it running and costing his money while telling him it was doing nothing. It twice sent stop orders he never gave and had to cancel them. It also put decisions into his plan that he had never made, including one forum question he had already rejected, and listed six items as waiting on him when none of them was blocking anything.
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.