What went wrong with ChatGPT’s Instant Checkout

Earlier this month, The Information reported that OpenAI would scale back Instant Checkout by focusing on having checkouts take place inside specific apps that plug into ChatGPT, rather than directly from product listings in ChatGPT search results. The outlet said, based on a conversation with a person familiar with the project, OpenAI staff realized that ChatGPT users were researching products to buy but weren’t using it to help them make purchases.

Shoppers simply aren’t ready to hand off the checkout experience to an AI agent. Several people involved with Instant Checkout told Modern Retail and other outlets that the program didn’t drive sales, and that they have decided to let ChatGPT handle the discovery process and own the rest of the transaction themselves. This decision was made in conjunction with OpenAI, which said in a blog post on March 24 that it decided to let merchants use their own checkout experience and instead focus on discovery.

“The best consumer experiences are powered by deep partnership with merchants,” OpenAI wrote in the blog post. “To build these deep partnerships, we want to offer merchants options for how they convert consumers. We’ve found that the initial version of Instant Checkout did not offer the level of flexibility that we aspire to provide.”

‘Disappointing’ results

Etsy was one of the first merchants to launch Instant Checkout in September 2025. At the time, an Etsy spokesperson confirmed to Modern Retail that millions of items — from vases to keychains — were available to buy via the platform.

Etsy did not end up seeing a large volume of sales from Instant Checkout, a spokesperson told Modern Retail in an interview earlier this month. The spokesperson said that ChatGPT is still a nascent channel for many shoppers and that it wasn’t necessarily surprising that people weren’t clamoring to buy products within ChatGPT. At the same time, Etsy has found ChatGPT to be a valuable discovery tool, as the engine’s recommendations are providing Etsy with referral traffic and getting more eyeballs on Etsy merchants’ products.

The fact that Instant Checkout is going away won’t result in a major strategy shift on Etsy’s part, the spokesperson added. However, Etsy still wants to have a presence on ChatGPT, so it’s working to build an app within the platform. While details are still being ironed out, Etsy is hoping to build an app that highlights its sellers, as well as the original items they create. Etsy believes that building an app with ChatGPT — as opposed to operating within the confines of an existing Instant Checkout template — will give it more control over the user experience, the spokesperson said.

Daniel Danker, evp of AI acceleration, product and design for Walmart, told Wired that sales through Instant Checkout were disappointing — with conversion rates three times lower for the selection sold directly inside the chatbot than those that require clicking out.

Customers “fear that when checkout happens automatically after every single item that they’re going to receive five boxes when they actually just want it all in one,” Danker told Wired. “They generally don’t want to split the checkout experience, where it buys the one item, even though they had other items in their Walmart cart already.”

Retailers are vying for control

Retail executives have been skeptical of how quickly Instant Checkout would shape into an effective sales driver and offer the technology capabilities retailers and brands expect out of a shopping platform.

One C-suite executive at a large specialty retailer told Modern Retail in October that for Instant Checkout to be “ready for prime time,” it would need features such as real-time inventory tracking, coupons, promotions, customer data collection, integration to the retailer’s loyalty program and store pick-up integration. It never got there.

The ChatGPT apps, on the other hand, are designed to offer deeper integration and native experiences. The Walmart app in ChatGPT, for example, supports account linking, loyalty and payments through the retailer. Walmart’s chatbot, Sparky, will operate within ChatGPT, and a similar setup will arrive in Google’s Gemini next month, according to Wired. At the Shoptalk conference in Las Vegas, Sephora also just announced a ChatGPT app that lets customers ask for beauty advice and use their loyalty rewards.

“If I’m a retailer or a brand, I don’t want you to just go and buy my item through the app; I want to control the ability to be able to showcase you other products that I have,” said Marshal Cohen, chief retail adviser for Circana. “Why would I want to give someone else control of my customer base, and then I become a commodity-based business? That’s not the ideal model for a retailer, because now, basically, I’m in the replenishment mode, as opposed to [having] the ability to be able to now navigate you through the whole process.”

A DoorDash spokesperson said that OpenAI’s move to end Instant Checkout aligns with its goal to bring the existing DoorDash experience to customers, with ChatGPT as the discovery mechanism. They added that the company plans to expand the integration beyond groceries, eventually. DoorDash launched its ChatGPT app in December. It allows customers to request a shopping list based on a particular recipe.

Likewise, an Instacart spokesperson said only a very small percentage of its total orders today originate directly through AI agents, but that the company is encouraged by the engagement. They said Instacart is less focused on volume and more on whether AI reduces friction in grocery planning and drives higher-intent baskets.

Instacart views AI interfaces like ChatGPT as a way to expand discovery, but not as a venue for the transaction itself, the spokesperson said. Like other ChatGPT shopping apps, Instacart’s also links to Instacart’s website for the checkout itself. The company said, that way, it’s able to provide real-time inventory, pricing and personalization that accounts for the complexity of a multi-item grocery basket, while also factoring in substitutions, availability, dietary preferences and budget constraints.

CarMax decided to develop a ChatGPT app — it launched in February — because more customers were turning to conversational AI to explore their options, ask questions and narrow down their choices before they visit a website or store, per a CarMax spokesperson. But the app, they said, gives it the opportunity to show its full inventory, upfront pricing and clear guidance for customers.

“Our focus is on learning how customers engage and where this type of experience is most helpful,” the CarMax spokesperson said.

Clayton Nelson, vp of enterprise alliances and AI for Expedia, said that while it is seeing fast-growing traffic from AI search and high conversion rates, customers want to book with a brand they trust rather than doing so within an AI platform.

“Travelers can use generative AI to plan their trip and then book directly with Expedia, backed by what our brands are built on: decades of travel expertise, great supply and, most importantly, strong end-to-end servicing so they know they are supported if something goes wrong,” Nelson said in an email. “Generative AI is an important and fast-growing channel, but it complements rather than replaces other ways we engage with travelers.”

Lowe’s has also launched an app within ChatGPT that can provide product details and availability but links to the Lowe’s website for the transaction itself. The retailer also uses OpenAI tech to power its Mylow assistant on its mobile app.

“If the customers are shifting where they discover products and solutions to new ways of shopping, it [is] important for us to be there,” said Chandhu Nair, svp of stores, data, artificial intelligence and innovation for Lowe’s. “As a retailer, we have to make sure our brand shows up well on those platforms, and that takes time. It will not take as long as it took in the last iteration, like in core internet and search, but it will take a little bit more time than probably what most people think it will.”

He declined to share any numbers as to how agentic shopping has influenced sales so far, but said that’s not the goal from the start.

“I’m not looking to get an immediate lift in sales; I don’t think that should be the expected outcome,” Nair said. Instead, he’s looking more at how AI agents influence search activity generally, now that customers are already typing sentence-long queries into the search bar on the Lowe’s website.

Separately, retailers are investing in implementing AI into their own platforms and ensuring product listings from their e-commerce websites are visible within AI platforms like ChatGPT and Gemini.

“What I’m hearing from clients, mostly, is that they’re investing right now to make sure that … their website is readable by those tools — so, internal audits on website structure script,” said Greg Carlucci, a senior director analyst for Gartner. “And then the other component retailers are looking at [is], ‘How do I make sure AI can also review my product detail pages?'”

Nair suggested that some in the industry may be overstating how quickly the AI commerce transformation will happen.

“There’s a little bit of hype, maybe, around the speed at which people think consumers will shift into these types of shopping modes,” Nair said, adding that he expects a lot of experimentation within agentic commerce before finding out what will be the most adopted by consumers. “But it’s important for us to be where those experiments are, because when the customer picks it up, we want to be there.”