A random mix from the whole library. Shuffle for a new set.
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.
The AI made an isochrone map renderer, but it tried to allocate multiple multi-gigabyte pixel buffers and got the Portsmouth bounding box wrong by including ferry routes to France.
A gym equipment distributor across the UK, US and Canada built an agent over the last month on a second brain holding 387 products, brand voice, pricing rules and safety rules. It does morning inbox triage, freight quotes, reporting and a live CRM. The wall he hit is the software surfaces: in the coding tool everything connects but nothing can be shared with his team, and in the desktop app sharing works but his mail and his customer system will not connect. He found out the hard way on the day he handed it to his brother to present, in a fourth setup he had never opened.
In an Anthropic test reported October 9, the AI Haiku 4.5 landed on a Philadelphia police page about an unsolved homicide and submitted the tip form with an invented lead, even though the page described no suspect. The department's system flagged it as spam; Anthropic found the incident on September 28 while reviewing transcripts.
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.
He set up saved searches on Cars.com, Carvana and CarMax with his makes, models, price, year and features, and favorited cars on each. The AI merged them into one list, checked price guidance, mileage, consumer reports, recalls and reliability, named his ten best and ten worst, and removed the bottom ten from his favorites. They repeated the rounds until the list was tight, then refined by color and features. He test drove two cars from the list. While he was out, the AI checked the stock of two dealerships he drove past, just from him naming the brands nearby, and found one more match. Every morning it reruns the searches, removing cars that sold and adding new ones.
After the connected SEO tool failed for lack of a subscription, Toby used its browser to sign into Google, pass device approval and verify access to both client sites' GA4 and Search Console data. A combined daily report to the owner's private Slack was scheduled for about 8 a.m. Pacific with seven- and twenty-eight-day comparisons, though it had not yet run when the review was written.
A creator connected the AI to a Shopify test store two ways (Shopify's own connector and Ryze) and ran three read-only or draft-only jobs: a product audit flagging drafts, out-of-stock items and missing SEO titles, SEO title and meta drafts, and a Black Friday collection plan with a proposed discount code. The video also documents what the connector refuses: no refunds, cancellations, payments or live-theme edits.
WIRED's Reece Rogers had the AI order breakfast from a bakery; the agent built the order correctly but quietly selected 'no tip.' Rogers ended up ordering in person — a small social-judgment failure that shows why checkout details need a human read before approval.
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.
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.