A random mix from the whole library. Shuffle for a new set.
Toby joined the agency's Slack group, announced itself and eventually sent messages through an explicit route after its first direct-message attempt failed. When a colleague asked for a PDF summary at about 4:24 p.m., Toby only picked it up around 5:13 and delivered at 5:15 — roughly fifty minutes in a live team conversation.
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.
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.
The AI as CAD tutor and direct python generation failed, then the AI implemented a bespoke DSL that produced exactly the DXF geometry he wanted.
Ran agents under KPIs for his website; agents deployed and monitored it and the CEO agent's report flagged an overnight traffic spike that took his Mac mini down and asked for a scale-up budget.
Concur's AI booked a man's flight but read his European passport wrong and put his birth date down as the 1st of the 18th month. The flight ended up booked with the wrong birth date.
An AI session on Windows ran an unprompted recursive delete meant to clear old test state; the target was written as a command substitution that resolved to the C: drive root, and with error output suppressed it deleted silently for about 35 minutes. Roughly 600 GB was destroyed, including the user's profile, git repositories, un-backed-up planning documents and the session transcripts themselves.
A Shopify/CRO freelancer gave the AI a hard $100 budget and 30 days to make a real profit, acting as autonomous project lead with a public ledger; he only authorizes spending and accounts. On day 1 the agent researched the market, rejected two strategies, and built the product: a 26-skill pack that runs a freelancer's proposals, SOWs, invoices and client updates from one personal business context file.
The maker of a free bookmark extension handed the AI the CEO job: a scheduled run every night at 9pm reads the store dashboard, checks comments, scans forums for people who need the tool, plans posts, and works on the product, then files a report in Notion. Nothing public goes out until he replies go. In week one it caught a rival extension with nearly the same name and told him to rename before launch, fixed store text that no longer matched the code, and built the next version, now in store review. The honest numbers: 4 weekly users, 14 installs in 30 days, no reviews, nothing spent.
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.
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.