According to Engadget, Microsoft announced a new feature called Copilot Checkout at the NRF 2026 retail conference, which is rolling out now in the US. The AI shopping assistant is integrated directly into Copilot and allows users to complete purchases without being redirected to a retailer’s website. Key launch partners include Shopify, Stripe, and Etsy, with participating retailers like Urban Outfitters, Anthropologie, and Ashley Furniture. Microsoft controls the interface, but the retailers remain the merchant of record, handling customer data and transactions. The report notes that Engadget has reached out to Microsoft to inquire about financial safeguards and how the system prevents AI hallucinations during purchases.
The AI checkout reality check
Here’s the thing: this is a massive bet on AI’s reliability. Microsoft is advertising this as a way to avoid the merchant site entirely. That’s a huge promise. OpenAI, which tried a similar shopping initiative months ago, had to include a disclaimer that its assistant “might make mistakes about product details like price and availability.” So, has Microsoft magically solved all those problems? The Engadget piece suggests maybe not, pointing out that OpenAI has reportedly had trouble getting merchants on board for its own version. It seems like Microsoft is charging ahead anyway, betting that convenience will trump potential errors.
It’s not a new idea, just a new wrapper
Let’s be real. Automatic shopping isn’t novel. Remember Amazon’s Dash Buttons? Those little physical widgets you’d press to re-order detergent? That was over a decade ago. This is basically the AI version of that. The core concept—reducing friction to a single action—is identical. Now, instead of pressing a button, you’re typing “order more paper towels” into a chatbot. The technology behind the trigger is different, but the goal is the same: make spending money as thoughtless as possible. And that’s always been a powerful, if slightly scary, retail strategy.
The hallucination hazard
This is my biggest worry. We all know AI chatbots make stuff up. It’s what they do. So what happens when one hallucinates during a transaction? The article’s example is perfect: you ask for Bounce dryer sheets, and Copilot buys you a literal bounce house. It’s funny until you get charged for it. Microsoft says the retailers handle the money, but who’s liable for the AI’s mistake? The lack of clear, public safeguards is a glaring red flag. For this to work at scale, the system needs near-perfect accuracy. We’re just not there yet with generative AI, and pretending we are feels like a recipe for customer service nightmares.
Who really controls the experience?
Microsoft controls the interface, but the retailers get the data. That’s an interesting split. It means Microsoft owns the customer’s first and last interaction—the ask and the checkout—while the merchant fulfills the order and gets the valuable purchase history. For Microsoft, it’s a play to make Copilot an indispensable, sticky platform. For retailers, it’s a trade-off: they gain a potentially huge new sales channel but cede some control over the branding and buying journey. Basically, they’re betting that the increased volume from AI-driven impulse buys is worth it. Only time will tell if that’s a good deal.
