TheChek News Flow

The Takeaway

OpenAI’s efforts to turn ChatGPT into a go-to personal shopper are off to a slow start.

Challenges with wrangling product data mean in-app checkouts aren’t yet widely available to the millions of shops that OpenAI said in September would soon be coming to ChatGPT. OpenAI and its early partners, Shopify and Stripe, have been working on ways to better standardize and share merchants’ product information in order to expand the shopping service more broadly, two people with knowledge of the efforts said.

The slow introduction highlights the hurdles to making widespread AI-powered shopping a reality. While people are already flocking to chatbots like ChatGPT for product recommendations and shopping inspiration, turning those conversations into purchases has proven complicated.

Buying something through a checkout in ChatGPT isn’t quite the same as buying the same goods on the seller’s own website, since ChatGPT is inserting itself between merchants, shoppers and payment firms. The chatbot shows a list of products to shoppers in search results, but ensuring the details are as up to date as what’s on a merchant’s website isn’t always easy. ChatGPT has to interpret information like pricing and in-stock availability that is often ambiguous and spread out across multiple systems.

If the agent gathers information incorrectly, it might charge the wrong price or place orders for something that’s out of stock, which increases the risk of disputes or other payment issues.

An OpenAI spokesperson said the company is working hands-on with merchants on how best to structure and standardize product data to make sure it’s accurate, and is trying to learn from early uses and incorporate feedback from merchants and payments firms.

To promote the in-chat checkouts, OpenAI has teamed up with Shopify, which offers ties to the millions of online shops that use the e-commerce giant’s website and checkout software. And to help retail, payment and AI firms coordinate transactions, OpenAI has partnered with Stripe on standardization to ensure AI software initiates purchases and communicates with merchants correctly. This set of rules, which the two companies call the Agentic Commerce Protocol, sits on top of existing e-commerce and payment application programming interfaces.

But while the protocol sets rules, it doesn’t fix the fact that merchants’ product information is often not standardized and can be open to interpretation—for example, a retailer may normally label something as “in stock” even if it is available only for a back order or preorder.

That’s meant OpenAI and Shopify teams have to do lots of hands-on work to get the merchants that are already selling in ChatGPT up and running, according to a person who worked with one of the brands.

At least one of the high-profile brands Shopify highlighted in September, luggage seller Away, isn’t yet available for purchase inside ChatGPT. And other Shopify merchants that want to join the checkout are still waiting for more details—three merchants and people who work with them say they have applied to participate but haven’t heard back yet. Away didn’t respond to a request for comment.

That includes a merchant with roughly $300 million in annual sales—on the bigger side for a Shopify seller—that applied on OpenAI’s site to join a beta test for the checkout. When its CEO followed up with the retailer’s Shopify representative about when more Shopify merchants would be added, they said the checkout was rolling out slowly.

Shopify, for its part, says that building the checkout has required a lot of upfront work and it has been adding more merchants by the day. The company says it plans to roll out selling directly in ChatGPT for all its U.S. merchants very soon.

On the payments side, Stripe has had to build a connection between AI apps and merchants’ backend systems so agents can properly understand merchants’ product catalogs and send transaction information from users for merchants to process.

Since the September announcements, Stripe has focused on helping more merchants get set up to receive agentic transactions, according to a person with direct knowledge of the efforts. Stripe also approached at least one commerce-oriented startup that specializes in handling transaction data between AI apps and merchants to discuss a potential acquisition or acquihire that would help Stripe scale up agentic transactions more quickly, a person with knowledge of the talks said.

One result of Stripe’s efforts since the checkout launch has been an expanded set of tools for merchants it released in mid-December, including one tool that allows sellers to give Stripe access to their product data so it can share that information with any agent in a more standardized way. Merchants currently have to join a waitlist for access. Stripe didn’t have a comment.

For OpenAI, which has said it takes a cut of sales made through its in-chat checkout, shopping would generate more revenue from the ChatGPT users that don’t pay for its service, which is the majority of its nearly 900 million users. OpenAI has told investors it wants to generate around $110 billion in revenue from nonpaying users by 2030.

How OpenAI’s checkout rollout progresses also has implications for the broader e-commerce landscape.

OpenAI leaders view partnerships with payment processors as an efficient way to grow in-app shopping, since the payment firms have large customer bases of merchants, a person who spoke with the company about the strategy said. Stripe and its rivals, meanwhile, don’t want to miss out on any potential new source of payment volume.

Worldpay, PayPal and Checkout.com have said they will adopt Stripe and OpenAI’s ACP standard, although Stripe is a rival to those firms. Backing a common standard, however, could boost overall adoption of in-chat shopping.

London-based Checkout.com is targeting a launch in the first quarter of 2026 for its ACP features, which will allow its merchants to make sales through ChatGPT checkouts, Chief Product Officer Meron Colbeci said in a mid-December interview.

PayPal, for its part, is planning to launch PayPal wallet payments in ChatGPT in the first half of 2026, Mike Edmonds, the company’s vice president of commercial growth for agentic commerce, said in an interview in late December.

Meanwhile, retailer enthusiasm for AI shopping tools is still a question mark. In-chat checkout could boost merchants’ sales, but they worry about damage to their brands if shoppers have a poor experience.

Shoppers also need to get used to the idea of buying stuff using AI. On PayPal’s October earnings call, executives acknowledged AI-driven shopping was still in early stages and hadn’t yet become a widespread consumer habit.

In addition to investing in the AI development work, PayPal will have to spend on marketing to drive user “habituation,” Chief Financial Officer Jamie Miller said. Those expenses, combined with other product investments, could cut into the company’s margin or earnings growth next year, she said.