Earlier this year, one of the world’s largest retailers quietly pulled its ChatGPT-powered checkout feature after it converted at one-third the rate of standard self-checkout. The coverage focused on UX. Wrong interface, wrong interaction model, move on. That seems like the wrong diagnosis. The checkout wasn’t the problem. The AI was operating without real-time inventory, live pricing logic, or fulfillment constraints. So it did what AI does best: filled in the gaps. Confidently. Incorrectly. The interface failed because the foundation was broken.