From tax accounting to payment facilities: OpenAI is getting "headaches" over the underlying trivialities of ChatGPT’s shopping features.

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OpenAI is attempting to turn shopping features within ChatGPT into a major commercial opportunity to support its multi-billion-dollar financing plans, but the AI giant is grappling with fundamental challenges of online commerce. Shifting from cutting-edge AI model development to the cumbersome construction of retail infrastructure, OpenAI finds itself needing to resolve a series of "tedious" yet crucial underlying issues such as tax compliance and payment processing.

On Wednesday, according to The Information, OpenAI’s internal business team has yet to decide how to handle sales tax collection for purchases made through its platform. As ChatGPT seeks to expand shopping features and introduce major brands, the company may be forced to take on more transaction processing—triggering complex tax compliance obligations. If OpenAI builds a large shopping business in the future, it’s highly likely to become a target for tax audits in various US states.

In terms of payment infrastructure, OpenAI recently selected a new software supplier to handle credit card data storage, aiming to reduce reliance on Stripe alone. According to sources, this transition is expected to be completed before the end of the first quarter and will allow OpenAI to introduce more payment processors, serving not only third-party merchants but also helping optimize the cost structure of its own subscription business.

These backend adjustments show that OpenAI faces significant operational friction as it tries to turn non-paying users into sources of shopping revenue. For investors, this means OpenAI must balance the risks of state tax audits and complex payment agreements, with its commercialization path relying not only on AI breakthroughs but also on its capability to adapt to traditional e-commerce logic.

Unavoidable Tax Compliance Challenges

OpenAI began adding checkout functionality within ChatGPT at the end of last year, currently selling products mainly from merchants who use commerce services such as Etsy or Shopify. These external companies handle most of the transaction and tax work. However, for the shopping business to truly take off, ChatGPT needs to list a broader range of products, including major brands, which may force OpenAI to handle more transaction phases and thus take on responsibility for collecting sales tax.

This means OpenAI may need to establish its own tax management capability and hire additional tax compliance staff. Over the past decade, dozens of US states have enacted "marketplace facilitator" tax laws. These laws typically require apps connecting buyers and sellers to be responsible for collecting and remitting sales tax—even if those apps don’t hold inventory.

Michael Wasser, Managing Director at EY specializing in state and local taxes, said online marketplaces need to keep up with thousands of ever-changing state tax rules. For instance, clothing tax rates may vary depending on whether it's considered a necessity or a luxury item. Wasser warned AI companies must understand the tax implications beforehand to avoid “getting into deep trouble.”

Although OpenAI's terms of service state that merchants are the ultimate facilitators of transactions and responsible for sales, marketplace tax laws in various states often override these designations. Regulators usually focus on how much control an app has over payment collection, and the boundaries are often blurry. Wasser remarked that “indirect” payment collection is an ambiguous term, leading to much negotiation and speculation.

Payment Architecture Restructuring & Decentralization

Despite the unresolved tax issues, OpenAI has started adjusting its payment settings, which may enable the company to play a more important role in online transactions. Previously, online payment giant Stripe provided all OpenAI’s payment infrastructure, including the storage of sensitive data such as credit card numbers.

According to informed sources, in recent weeks OpenAI struck a deal with a new software supplier to store payment data on secure external servers that are not bound to any specific payment provider. Through a process known as "tokenization", OpenAI will receive masked payment information and relay it to merchants.

Migrating card data to an independent storage provider will make it easier for OpenAI to accommodate merchants using processors other than Stripe, such as large independent retailers. The base rules of OpenAI's shopping feature (known as Agentic Commerce Protocol) allow merchants to use any payment processor, but currently Stripe is the only company handling payments for sales made through ChatGPT.

Profit Margin Considerations & Partner Rivalry

By splitting card storage from Stripe, OpenAI will also be able to work with a wider range of companies to process payments for its software sales, including recurring subscription fees charged to ChatGPT users. According to sources, OpenAI is weighing the possibility of introducing other processors once the migration is completed.

This move will help OpenAI lower costs and improve profit margins. OpenAI expects subscription revenue next year to exceed $25 billion. If more payment processors are introduced, Stripe may ultimately get only a small slice of that huge revenue.

For many growing companies, adding more payment processors is a natural progression. But for Stripe, it’s still a setback—the company gained a major foothold in the market by partnering early with companies such as Shopify and Instacart.

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