The race to build the AI shopping assistant is producing an early verdict: retailers are not willing to give up the checkout page. Two developments this week illustrate the split. Google announced a partnership with Gap to let shoppers buy directly through Gemini, using Google Pay and keeping Gap in control of the transaction. Meanwhile, OpenAI is quietly retreating from its own attempt to own the purchase flow inside ChatGPT, after data showed it was not working.
OpenAI launched what it called Instant Checkout inside ChatGPT on September 29, 2025, in partnership with Walmart and Stripe, using what it described as an Agentic Commerce Protocol. The idea was to let ChatGPT users browse roughly 200,000 Walmart items and buy them without leaving the conversation. The results were disappointing. Daniel Danker, Walmart executive vice president for AI acceleration, told Wired that conversion rates inside ChatGPT reached roughly one-third of Walmart's own native channels. He called the experience unsatisfying. OpenAI acknowledged in a statement: "We have found that the initial version of Instant Checkout did not offer the level of flexibility that we aspire to provide, so we are allowing merchants to use their own checkout experiences while we focus our efforts on product discovery." Gartner analyst Bob Hetu told CNBC that OpenAI underestimated how difficult enabling transactions would be. The linear, single-query format did not match the multi-item basket behavior that drives order value on Walmart's own platforms. High-consideration purchases like televisions were excluded because the chat flow could not support bundling and accessory recommendations.
Google and Gap illustrate the alternative approach. Gap announced it will become the first major fashion company to offer checkout within Google Gemini, using Google Pay for the transaction while Gap handles shipping and logistics. The critical difference from the OpenAI model is that Gap provides its product data to Gemini in advance, rather than letting the platform crawl and display whatever it extracts. Gap chief technology officer Sven Gerjets described the strategic logic: "we need to become relevant to conversational search, and that means controlling what surfaces and ensuring it is accurate." Gap will also deploy an AI-powered sizing tool called Bold Metrics to help customers find their fit.
The two approaches reveal something important about how AI platforms and retailers are negotiating who controls the commercial relationship. OpenAI initially bet it could own the transaction layer and extract a fee from merchants for the privilege. The Walmart data suggests that model has not earned retailer trust or consumer confidence. Google's approach is more conservative: provide the distribution, let the merchant handle everything else. Retailers appear to prefer the second model, at least for now. The open question is whether the AI assistant that does not own the checkout can still capture enough value to justify its place in the shopping journey.
