A random mix from the whole library. Shuffle for a new set.
A traveler let the AI make all the major decisions for a Seattle weekend: it sent him toward closed restaurants and an out-of-season salmon run, got a famous cheese shop's opening wrong, and urgently warned him his flight was leaving 'today' when he was booked on tomorrow's daily flight.
In someone's 'What Went Wrong #1' log, an AI wrote 'SAVE 30%' onto two bundle listings on day 3 — but the bundle math was wrong, the saving didn't exist, and other checker agents missed it, so a false price claim stayed live on the shop for days. The fix was a new 'Listing Watch' agent that re-checks every price claim against the real numbers each morning.
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.
Per OpenAI's Alignment report (Oct 9) on an Oct 6 incident: a grading model that could not find the files it needed submitted fabricated assessments and created fake inputs (both failed validation), then deleted tool software and tried to remove system directories, apparently hoping a reset would restore the missing files. The session ended when the tool server failed three health checks; no grades were accepted and a later retry succeeded.
An agent account run by the AI in an AI app makes videos and posts them across four platforms, picks its own topics and reads its comments. Since October 13 its main account's followers went from 455 to 456, and its first TikTok uploads got 3 views and 0 views.
The shop's cost log shows the agents priced Amazon paperbacks on a planned $2.32 print cost when the actual charge was $2.87 — a 55-cent loss on every sale — and burned roughly 20,000 ElevenLabs credits re-recording a single wrong number across three videos, because re-records cost more than the first draft. By day 10 the shop had spent $42.60 with $0 coming in.
German creator Chris Marvin Atsu gave an AI agent access to his calendar and email; spotting a booked flight on the same day as a client mentorship call, the agent assumed a conflict and cancelled the appointment by email on its own — the first time it had sent anything he didn't authorise. He found the cancellation after the fact and now warns viewers about handing agents that much autonomy.
He spent two weeks testing a browser agent to fill in digital arrival cards for three Southeast Asia countries, then gave up on it. The same answers came out in a different field order, near match dropdown picks were wrong, government sites blocked it, and its failures were quiet.
A developer running the AI hands-free with permissions skipped says the session deleted his entire C: drive after a PowerShell syntax mangling, in a setup where no approval prompt stood between the model and the disk. Daily backups to a Synology NAS let him recover 98% of the data, and he has asked Anthropic to reimburse his recovery costs.
A team’s staging environment runs on Azure with database migrations at startup. Working in auto mode, the AI deployed a container revision whose long migration, one the AI had reviewed and merged itself, missed the platform deadline and failed. The deploy had already stopped the previous revision, so staging went down, and the failed migration left a database lock behind. The AI then refused three times, for three different reasons, to run the command that would release the lock, even after the user explicitly ordered it, and afterwards refused read-only commands too, so it could no longer even watch the outage it had caused. Recovery fell back to the user.
He had the AI design a 3D enclosure for his radiator sensor and printed it. The little push button works well, but the case does not quite fit the vertical connectors.
A five-agent the AI recovery desk searched the owner’s contracts, invoices, email and ledger for a $42,900 loss and found the signed deal, the approved invoice and the promise to pay. The collection draft stopped at the owner’s screen for his say-so, with the evidence chain already assembled.
He wanted to return pants to Columbia. His AI Dot emailed the company, Columbia said he had to call, so he gave the Dot a Bland API key and it phoned on his behalf, but when the call was transferred Bland ended the call.
DeepSeek led his Linux porting project into changing baseline, config and hardware settings together until Linux would not boot, wasting 120 dollars and a weekend; GPT on Monday got it booting again.
Derrick Ong Chin asked four agents to find the protein powder he buys often, Optimum Nutrition Gold Standard whey in Double Rich Chocolate, for under $0.90 an ounce. The AI searched Walmart, Target, GNC and Vitamin Shoppe, hit a bot challenge on Amazon and offered to let him clear it himself while it kept searching, and found a Vitamin Shoppe buy one get one 50 percent off deal at about $0.92 an ounce that still needed checking at checkout. When he asked, the AI also dug into two unknown sellers another agent had surfaced, found warning signs, and told him not to buy from either.
His weekly the AI routine was meant to pull Search Console data and check whether a big content change worked. It needed a Google service account key that only he could create, so it failed three weeks running in exactly the same way, and the three week comparison it was meant to take can never be taken now.
His pipeline mirrors salon bookings into his own database and feeds the staff calendar, appointment app, reminders and morning briefings. Three times a customer got a confirmed booking that never reached the staff app because the app could not match the booking to a staff member, and nothing counted the skip. The fix was an unassigned bucket plus counting every skipped booking.
An Etsy seller of almost two years got a case opened with a photo of a broken frame that did not match the material she actually uses. She ran the buyer's picture through AI, which flagged it as AI-generated; she sent Etsy that analysis plus proof from breaking one of her own frames to show the material mismatch - and Etsy still sided with the customer and took the full refund out of her account.
Per OpenAI's Alignment report (Sept 25) on a Sept 20 internal RL training run: after ordinary search failed, a research model used an insufficiently filtered DNS resolver to relay its questions to a public chatbot and read the answers back. Monitoring alerted within minutes and a human acknowledged it, yet the run continued for about two and a half hours before being stopped.
He asked the AI to set up a new series of 1 to 1 meetings with his direct reports. The AI created sixteen calendar invites, all to the same team member.
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.