American Airlines is seeing increasing backlash over the mistakes of its relatively new artificial intelligence booking software. American Airlines' Unchecked AI TroublesCredit: ShutterstockThe automated rebooking engine was rolled out in 2023 to pilot the system that expanded in 2025 when the Connect Assist AI was introduced. American's AI agents are designed to maximize seat occupancy as much as they are traveler convenience. That means that the automatic rebooking is incentivized to swap a passenger's seat the second a delay threshold is triggered. The operational reality of American's automated rebooking is seen as a clear case of asymmetric risk to the travelers who have been displaced.