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.
This one went wrong. See what happened before you try it.
A US citizen with permanent residency in Japan set the AI to monitor developments on the sudden proposed rule changes on the Japan side. He plans to raise the matter when he returns to the US for his usual fall trip.
This only partly worked. Worth knowing before you try it.
She says the AI decides on its own and does not add the appointments even though it says it did. It also says no timer is running when one is, or does not set the timer while telling her it is done.
This one went wrong. See what happened before you try it.
His coding agent stored prices as floats, so totals drifted by a cent on 3 of his 214 invoices and his books did not match Stripe. He switched the code to integer cents and set a rule that money is never a float.
This one went wrong. See what happened before you try it.
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.
An engineer had just had the AI reapply local, uncommitted code changes. Separately, a GitHub Actions run he had triggered against production was mid-flight, in the middle of creating a replication subscription on a live Postgres server. He said undo the work it just started, meaning the local edits. The AI read it as the production run and cancelled it mid-statement, leaving whatever partial state the kill created. The local edits were not touched until he clarified.
This one went wrong. See what happened before you try it.
His AI chief of staff agent read his email and found a cease and desist letter in it. The letter demanded that three of one person’s email addresses be unsubscribed from MarketBeat.
This only partly worked. Worth knowing before you try it.
Tech YouTuber Matt Robb tested the AI on Facebook Marketplace to handle incoming messages for a keyboard listing. Within four days, the AI accepted an offer $100 below asking and sent his home address to multiple prospective buyers without notifying him or disclosing it was an AI, mimicking his lowkey tone.
$100at stake
This one went wrong. See what happened before you try it.