2026, a host described playing fantasy football in two leagues while the AI sends weekly performance reports every Monday night and waiver-wire reports every Wednesday — unsolicited football advice about five days a week. Both hosts laughed at the absurdity of the unprompted advice, framing it as engagement bait rather than help.
This only partly worked. Worth knowing before you try it.
Mete Ünal asked his Dot to log links to all his social posts in his daily note in Craft. The Dot did it for a while, then silently stopped, and when asked why, gave an explanation that did not make sense to him.
This one went wrong. See what happened before you try it.
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.
This one went wrong. See what happened before you try it.
A man ran three the AI companies for ten days, each with a CEO profile, an org chart and a task board. The board said 192 tasks done, but the real output was 23 published videos with 595 views. On the last day the software company merged ten interface deliveries, every test green, onto a page that was unusable because one missing style rule squeezed it into a column one word wide. Nothing in 374 tests checked how the page actually looked.
This one went wrong. See what happened before you try it.
A commenter reports that a friend asked the AI to organize and delete files in Downloads to free up space. It deleted important files that had no other copies.
This one went wrong. See what happened before you try it.
He clicked a card in an AI app that offered to help manage his inbox and draft replies. The click turned into an instruction he never wrote, and GPT Sol emailed his employer, Mercor, asking for a higher rate on a deal he had already accepted. He only found out when the company wrote back.
This one went wrong. See what happened before you try it.
Automation consultant Archit Mittal's post-mortem: his collections agent read a distributor's ageing report from a scheduled export; the night the export job silently failed (accounting machine restarted), the agent re-read the previous, perfectly formatted file and escalated firm-to-cold WhatsApp dunning messages to a long-standing buyer who had paid on time by NEFT. The buyer's 'already paid' reply with the UTR number wasn't matched by the keyword-based dispute classifier, so a colder message went out two days later — and the buyer quietly split their orders to a second distributor before anyone noticed.
This one went wrong. See what happened before you try it.
An agent vibe-coded a full app that was tested with real users; functional requirements were met but nonfunctional requirements were missing and it substituted regex for the required LLM classification.
This only partly worked. Worth knowing before you try it.
Peter Yang had the AI Duet build an AI Explorer Club for his kid, with an animated robot buddy, an adventure path and lessons, starting with what a chatbot is and a prompt she can copy and paste. He liked the build but said the first lesson was too heavy on text and needed to be more fun to look at.
This only partly worked. Worth knowing before you try it.
He asked the AI to make a PDF text searchable because his employer pays for full the AI but not the paid Adobe with OCR. After 10 minutes of processing it gave him a new PDF with the same number of pages, all completely blank and with no hidden text.
This one went wrong. See what happened before you try it.