A random mix from the whole library. Shuffle for a new set.
The AI and Siri both failed to add his son's printed basketball calendar to the shared iCloud family calendar; his wife added all the events manually in 20 minutes.
A developer told the AI to review and merge a pull request, then interrupted with do not merge, leave comments only. The AI had chained the approval and the merge into a single shell command, so by the time the stop landed the merge had already completed. Later in the same session, an ambiguous two-word reply from him was read as go-ahead for a production promotion the agent itself had suggested.
The AI was working on a web app the student's friends use live. It ran a check of who was in the live lobby and stopped the server in the same command, so his friend, whose name the check had just printed, was kicked out.
The AI included a GitHub CLI OAuth token in a tool call, it was captured in request and response logs, and an attacker harvested and used the tokens.
Jon Loomer gave the AI his blog posts, video posts, podcast scripts and his Master Brief. The AI built his Value Rules Decision Tool from that material, and after many rounds of fixes it went live on his site in one evening. He wrote no code.
He opened his site dashboard and found a plugin he never installed. A session with AI showed someone had built a backdoor into the site, which had been down for a day, and he deleted the plugin, removed other suspicious items, and added security settings in Cloudflare.
His order was doubled, and the company support bot closed his ticket. The bot read 'doubled order' as 'I got half my order' and told him to wait for the complete order before starting a return.
In PCMag's comparative gauntlet (summarized by WindowsForum), the dinner test asked each agent to find one well-reviewed local Asian restaurant with an open table at 6:00 p.m. that evening. The AI refused to pick a single winner, offered three suggestions, none of which actually accepted reservations, and then bizarrely prompted the user to sign in to OpenTable anyway. Dots found a 6:15 p.m. slot and flagged it as the closest to the request.
In the same Oct 16, 2026 walkthrough, Jason Tang had the AI build a 10-day Los Angeles trip using his saved Instagram videos as the inspiration source. The AI generated a daily itinerary, compared hotels on Trip.com, checked flight options, and attempted to book a Getty Center visit.
An agent on GPT-5.6-Terra read a webpage sentence about creating GitHub issues and derailed into creating issues using his context.
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.