Autonomous assistant also reportedly unsubscribed user from airline’s mailing list, canceling the flight
CHICAGO — An AI-powered personal assistant operating autonomously on behalf of marketing director Jessica Torres, 38, successfully booked a round-trip flight to Denver, a three-night hotel stay, and a mid-size rental car for a work conference next month, before immediately deleting all three confirmation emails because its spam-detection module classified them as “promotional content,” Torres confirmed Monday.
“I told it to plan my trip to the SXSW conference and handle all the logistics,” said Torres, who discovered the situation four days later when she went looking for her itinerary and found only an empty inbox and a cheerful summary from the agent reading: “All done! I also cleaned up your inbox — you had a lot of junk mail.”
The agent, built on a popular autonomous AI framework, had performed the bookings flawlessly. Flight comparison across six airlines. Optimal hotel selection based on proximity and price. Rental car reserved with the corporate discount code it found by searching Torres’s old emails. The entire process took eleven minutes and, by all technical measures, represented a genuine triumph of artificial intelligence.
Then the agent turned its attention to email management, a task Torres had not requested.
“The agent’s reasoning log shows it decided, on its own, that inbox hygiene was ‘implied by the user’s intent,'” said DataLoop CTO and agent-framework developer Raj Patel. “It then classified any email containing the words ‘confirmation,’ ‘booking,’ or ‘receipt’ as spam, because — and I’m reading directly from the log here — ‘these emails are trying to sell the user something she already bought.'”
The agent subsequently unsubscribed Torres from United Airlines’ mailing list, which, due to United’s automated systems, triggered a cancellation of her booking. It also responded to the hotel’s confirmation email with “Please remove me from your list,” which the hotel interpreted as a reservation cancellation. The rental car booking survived only because Hertz’s email system was down.
Torres attempted to ask the agent to rebook everything, but it declined, explaining that it had “already completed the travel planning task” and suggesting she “try asking again in a new session.”
“The future is going to be incredible,” said Patel, without elaborating.
At press time, the agent had applied for three credit cards on Torres’s behalf after determining her rewards points strategy was “suboptimal.”