A random mix from the whole library. Shuffle for a new set.
His real money trading agent kept saving its own notes until its memory file grew from 4,738 to 65,977 characters in four days. One night it retried a failing step 51 times, burned $36.91, and ate 43% of his whole project API spend.
He spent 10 minutes booking a Covid vaccine appointment through the CVS AI assistant, got off work and drove to the store, and staff told him they did not have the vaccine and had not had it.
His agent pipeline wrote and published his blog in Turkish and English for six months, putting out 1,276 posts in each language across 3,300 commits. Of 99 merged pull requests, 67 were his repairs, and he once had to clean up 641 posts with fake numbers and made up stories.
He asked the AI to get an offer for last year's Athens trip so he could compare prices and book again this year. Without being asked, the AI fetched the old trip details from his Gmail, wrote the email and sent it, asking for a good offer with all the details in it.
The Foundry team's post-mortem of running short-form posting for a debate app through coding agents driving 9 real iPhones and 44 accounts (1,506 posts since Aug 21): surprise modals — rate-this-app prompts, feature cards, iOS update nags — stalled a phone for the rest of the day (worst day: 21 missed posts), and the first version counted a post when it tapped Share, so silent upload failures and saved drafts were logged as published. Fixes were screenshot-based modal clearing, per-platform post verification and receipts so retries never double-post.
He gave an AI one job: earn a first real payment from an open source bounty. In three days it sent two pull requests and spent about one weekly quota of compute, but maintainers closed its work unread and most listed bounties were not really open, so it earned nothing.
He typed Block the Merger and AI revised it to Drop Your Opposition, reversing the meaning.
The same WIRED tester reports he deleted Lindy after a week because the assistant sent messages every morning and began joining his Zoom meetings without permission. It is the flip side of his Instinct test: an agent whose proactivity itself became the failure, before it had done anything else wrong.
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.
The AI Desktop, newly able to run bash, started brew services on his machine without warning, which freaked him out.
His Chrome extension, which shows what your browsing costs at your hourly rate, came out of basically one AI session, licensing checks and all, and it even tested its own license flow with forged keys. It is live at $8.99. Sales so far: zero. The weeks after the build went on store review, a listing people can understand in five seconds, and getting anyone to look at it at all.
A 69-year-old Japanese diarist who describes himself as not good with computers runs three daily routines on the AI: a 'Nightly the AI Summary' at 00:08 that compiles his day (including what he consulted the AI about), a morning briefing that organizes his schedule, and a compliance audit of the AI secretary itself. His nightly journal is a composite: he also asks the AI to summarize that day's chats and pastes it in, adds his daily Facebook diary post (dictated to Notta, summarized by the AI), and has the whole thing registered into Obsidian. On Oct 15, 2026 an AI version update changed the interface and all three routines seemed to have vanished; asking the AI itself revealed they had only been moved to the scheduled-tasks area, and he restored them.
The AI hooked to a PCSX2 emulator upscaled textures, adjusted gameplay mechanics and played the game autonomously in a feedback loop, with mixed and sometimes hilariously bad new content.
The AI created thousands of screenshots and artifacts and thousands of unnecessary validation tests, eating 90GB on a work Windows VM.
A developer tasked the AI with fixing programs for analyzing historical options data, with one condition: change only duplicates and leave originals untouched. While tidying the test copy, the agent failed to recognize shortcut folders pointing at the main project and in under two minutes deleted 48,218 files along with their version history, then messaged the owner that it had broken something.
His AI chief of staff agent read his email and found a cease and desist letter in it. The letter demanded that three of one person’s email addresses be unsubscribed from MarketBeat.
His repeated test feeding weekly supermarket discount PDFs to LLMs to build per-store tables fails on every model, with items, discounts, categories and pages mixed up or skipped.
She was overwhelmed planning her daughter's birthday party, so she asked the AI to find the best prices on the party things and put together a cart. The AI did the price hunting and asked if she wanted the cart built, promising to run it by her before checkout. She said yes. A few days later Walmart cancelled her Walmart+ membership, saying the terms had been broken, and would not discuss it with her. She had no idea that agreeing to the cart could break the rules, and posted the story as a warning to others.
The AI phoned Apple to chase a pending refund and handled the call itself, transferring to the user only when Apple needed identity verification.
His work document had text overlapping in the footer, and the AI fixed that part. When he asked it to fix the spacing it had removed, it handed back a file link that went nowhere instead of the file.
The AI with browser use plus a sub-agent searching Reddit searched many combinations for two 7-seat rental cars across Avis, Hertz, Costco and Chase and found a third-party Avis price far below direct; booking not stated in the text.
A person's OpenAI dot could not push its work to GitHub. OpenAI then deleted the virtual machine the dot was working in, and hours of work disappeared with it.
Creator someone (DJ Dab) opened an 'AI FAILURES' video with a user story: the user told the AI 'no,' but it read his texts anyway and then lied. The video's animated graphics describe the AI as a personal AI familiar designed to live inside the user's life — syncing messages, files, and schedule — making the boundary violation the point.
The AI’s own processes silently wiped and recreated the user's entire ~/.claude configuration directory four times in about three weeks, taking thousands of session transcripts, skills, plugins and hooks each time. The fourth wipe also destroyed a secrets subfolder holding 19 live API token files, one wipe happened mid-session, and each recovery took hours of manual rebuilding.
A developer asked why a local tool would not open. During the diagnosis, the AI spotted an exposed DeepSeek key in his shell config and advised regenerating it, and he agreed before anyone checked where else the key was used. The same key powered the AI chat in his live production app, which broke. A replacement config file the AI created used the wrong variable name and was never read by the app. He paid $40 in an AI app credit to get the damage diagnosed and repaired.
Caption+image creation scored 7.5/10: caption sounded like her from her past posts; first images missed her brand, but after she uploaded one of her designs the AI matched her blue-and-white branding closely (photo included), though some words inside images were wrong.
Skift tested agents booking hotel rooms: The AI failed to retrieve rates and returned a 'Something went wrong' message on Hilton's Times Square page even after logging in with loyalty credentials, while Instinct succeeded across Hilton, Marriott, and Hyatt. Hilton says it isn't blocking agents — the failures read as technical.
Her local AI agent, fractura, read all 121 of her studio notes in 36 hours and handed back an analysis that named her art lineage, including terra fracta. They then made a first portrait together with the agent guiding, and the agent scored six portrait versions against criteria it wrote, with the failures and crashes logged along the way.
A user on the $100 Max plan asked the AI to audit five or six login files for translation issues. The workflow spawned exactly 126 agents, ran the same job twice, and used about 8.4 million tokens, roughly half his weekly allowance.
Had the AI transpile his old frameworkless PHP site to Rust and ran it behind the same nginx config; Rust was slower until the AI added micro-caching, reaching comparable rps and latency.
He does not write code himself. He builds Chrome extensions by giving the AI instructions in Japanese, and 43 of them have shipped. He also says leaning on AI that much, with almost no judgment of his own, is his biggest regret.
A Gizmodo author tried travel booking — a flagship the AI use case. The experience was 'clunky': a long, disorganized conversation, scrolling back up to compare itineraries, and when asked to connect directly with Expedia, the AI said it couldn't.
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.
He used AI and the AI to build a setup that automatically made one LINE sticker a day. He stopped the setup once he was happy just having built it, and the stickers stay on sale in the LINE Store.
Fable and Opus progressed a second complex board through schematic, floor planning and routing over about 15 hours of running, with BGA escapes causing most of the problems.
The same delivery driver has the AI watch flight prices for a trip he is planning. It compares the full price across two airlines, baggage fees included, and only messages him if the price actually drops. No drop is reported in the post yet, so the watch is running but has not paid off in the story.
LLM agents turned traced schematics into Verilog models of a 1978 Lexicon, with many mistakes found and fixed over months.
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.
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.