According to The Verge, Microsoft is launching a new in-chat checkout feature for its Copilot AI assistant, allowing users to purchase products directly within a conversation. The feature is currently rolling out on Copilot.com for users in the United States. It works with a select group of retailers including Urban Outfitters, Anthropologie, Ashley Furniture, and some Etsy sellers. Payment processing is being handled through partnerships with PayPal, Stripe, and Shopify. The system lets you complete a transaction, entering shipping and payment info, without ever navigating to the retailer’s own website.
The AI shopping agent race is on
So, here’s the thing. This isn’t a surprise. It’s not even original. OpenAI launched a similar feature for ChatGPT last year, Google is doing it in Search, and Perplexity’s AI is built for it. Basically, every major AI player is converging on the same obvious idea: if the chatbot can recommend a product, why shouldn’t it also be the cash register? It’s the logical, if somewhat cynical, endpoint of turning these “assistants” into commercial intermediaries. The value proposition is convenience, sure. But the real prize is controlling the transaction—and the data and fees that come with it.
Convenience at what cost?
Now, the immediate question is: who really benefits from this? For the user, it’s one less click. That’s nice. For Microsoft and its peers, it’s a potential new revenue stream and a way to make their costly AI investments actually pay off. But for retailers and brands, it’s a double-edged sword. They get a new sales channel, but they also cede customer relationship and critical purchase data to a tech giant’s platform. They become a commodity supplier in someone else’s walled garden. And we’ve seen this movie before with Amazon. Speaking of which, The Verge notes Amazon isn’t thrilled about Perplexity doing this. Imagine how they’ll feel when Copilot and ChatGPT are siphoning off direct sales, too.
A skeptical look ahead
I think we should be skeptical of how neutral these shopping “agents” will remain. When you ask for a lamp recommendation, will Copilot surface the best lamp? Or the lamp from a retailer that has the best commercial deal with Microsoft? The inherent conflict of interest is massive. And let’s not forget the historical failures here. Remember when every social media platform tried to become a store? Most of those efforts flopped because people, oddly enough, like to shop in dedicated places they trust for commerce. Throwing a checkout flow into a chat interface feels like a solution in search of a problem for many purchases. It might work for an impulse buy on a small item. But for anything considered? I’m not so sure.
Ultimately, this is less about a revolutionary new way to shop and more about platform companies scrambling to monetize AI. They’re building the mall, and they want every retailer to rent a stall. The convenience is real, but the trade-offs—in terms of competition, consumer choice, and data privacy—are just beginning to surface. It’s a buy button. But what are we really selling?
