- Iman Deschâtres
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OpenAI is stepping back from its earlier plan to allow users to buy products directly inside ChatGPT, The Information reports. Instead, the company will route purchases through third-party apps connected to the chatbot.
This marks a significant pivot from the wave of ambition seen in late 2025, that fuelled expectations that AI was about to reshape the way we buy in 2026. OpenAI introduced Instant Checkout inside ChatGPT in September 2025, followed by Shopping Research in late November, turning a product search into a guided conversation that can end in a purchase without ever leaving the chat. Around the same time, Perplexity teamed up with PayPal to launch in-chat “Instant Buy” on November 25, 2025, letting users go from question to checkout in a single thread. Then in January 2026, Google announced the Universal Commerce Protocol (UCP) at NRF Retail’s Big Show, an open standard for agentic commerce designed to power native checkouts directly within Google Search’s AI Mode and the Gemini app, with the feature described as coming soon rather than fully live at launch.
Why OpenAI Stepped Back from In-Chat Checkout
One of the reasons for the OpenAI pivot is not only the lack of engagement but also the compliance requirements that created a barrier.
As Nelson Oboh noted in the keyword article, for example, “companies operating in the U.S. are required to calculate, collect, and remit sales taxes across thousands of local tax jurisdictions …capability that is a standard component of established ecommerce platforms which automatically handle tax calculation during checkout.”
It is precisely this kind of infrastructure that OpenAI had not yet in place when it decided to step back.
The Shift from Traditional Ecommerce to Agentic Commerce
Tax laws have been designed for the way online shopping worked for the past decades: you searched, compared, clicked, and bought directly on a merchant site or on a marketplace.
However, that funnel is starting to converge into a single conversation. You describe what you’re looking for, the AI explores the web, weighs prices, reviews, and availability, explains the trade-offs, and increasingly, it will complete the purchase on your behalf, no redirection, no separate checkout page.
The Core Question – Who Is Liable for Tax?
In this new environment, one question matters: who will be liable for tax?
As AI becomes the researcher, the buyer, the negotiator, and effectively the customer, linking it to a real-world taxpayer will be key.
How Ecommerce Tax Liability Has Already Evolved
A decade ago, the model was simple: one seller, one customer. The person liable for tax was the seller named on the invoice.
The exponential growth of ecommerce has since reshaped those rules, with liability increasingly shifting onto foreign suppliers, who are now expected to comply at the point of consumption.
Determining the Customer Location in AI-Driven Commerce
Customer location will remain a central consideration, but the signals used to determine it are evolving.
For physical goods, the dispatch address will continue to anchor the transaction. For services and digital products, payment information will grow in importance – billing address, country phone number, and similar data points will carry more weight.
Meanwhile, IP addresses risk becoming unreliable: VPNs already obscure user location, and as AI agents execute purchases autonomously, the server location of the agent itself could be mistaken for the buyer’s location, a gap that existing tax solutions may not yet be equipped to handle.
The Breakdown of the One Seller / One Invoice Model
The seller side is where it gets interesting. The old model, one seller/one invoice/one liable party, has effectively broken down.
With millions of sellers operating across borders, enforcement against individual merchants became unworkable. The response was the introduction of deemed supplier rules: a legal fiction that treats something as true for tax purposes even if it isn’t strictly so, that shifts tax liability away from the seller or the merchant of record and onto the platform facilitating the transaction.
The definition of which platforms fall under this liability has deliberately been kept broad.
Why the Checkout Platform Determines Tax Liability
Put simply, the liable party is the platform on which checkout happens. This is the foundational logic for analysing how tax liability gets assigned to a third party that may have no direct role in the underlying sale.
A Meta example illustrates this clearly. When Meta phased out Facebook and Instagram Checkout, redirecting sales back to merchant sites, it also stepped out of the deemed supplier framework, and with it, stopped being liable for tax under Marketplace Facilitator laws.
This points to the two recognised exceptions to the fiction of platform liability:
first, where a platform’s role is limited to redirecting the user to a merchant site without hosting the transaction itself; and second, where a platform is only processing payment without facilitating the sale.
When Multiple Platforms Are Involved
However, simply following where checkout happens may not be enough as the definition of “platform” for tax liability has been kept on purpose broad.
This was indicated in the OECD’s March 2019 report The Role of Digital Platforms in the Collection of VAT/GST on Online Sales that did not attempt to define “digital platforms” as “it is a concept that is likely to evolve over time.”
In practice, agentic commerce invariably involves multiple entities. In such scenarios it is difficult to assess on which platform the transaction really occurred, who is liable and this may be further clouded with the evolution of technology while platforms and tax jurisdictions still crave certainty: who is the liable party for the collection and remittance of tax?
How Different Jurisdictions Approach Platform Tax Liability
Some guidance has been provided by different jurisdictions and the OECD when faced with sales where multiple platforms are involved.
It is the approach taken by Australia, for example, who relies on the contract to determine who is liable for the Australian GST that applies to an online sale.
If there is no written agreement then Australia’s default rules fall back on which is the first entity to authorise the charge for the sale. If such criteria does not apply then the next rule looks to which is the first entity to authorise the delivery of the supply.
Finally, the Australian Commissioner of Taxation also has the “power to prescribe, by legislative instrument, additional rules to determine which EDP operator is responsible for GST. These additional rules will operate only in the absence of a written agreement between the EDP operators.”
Singapore, New Zealand, and the EU Approach
Other jurisdictions, to a large degree, follow Australia’s path with some crucial differences.
Both Singapore and New Zealand place their focus on who authorises the charge to determine who is the liable party for the collection and remittance of the respective GST in these jurisdictions.
Where Australia has default rules no such default approach exists in Singapore and New Zealand. However, both Singapore and New Zealand also have a clause that you can decide by contract who will collect the tax. It means that platforms can agree to shift the tax liability to another platform.
The EU on its side in the EU’s explanatory notes for the 2021 VAT on e-commerce Rules refers back to the checkout to determine liability when multiple interfaces are involved i.e. “the interface where the order is taken and through which the supply is concluded.”
The Emerging Tax Challenge of Agentic Commerce
We are still in the early stages of agentic commerce, but the questions it raises for tax liability are not abstract, they are arriving faster than the frameworks designed to answer them.
Think about your last online purchase: did you know which entity was collecting and remitting the tax on that sale? Did you check the invoice or the bank statement?
Now multiply that uncertainty across an AI agent executing purchases autonomously on your behalf, with no customer in the traditional sense at all – with an ever-increasing, “snowball-like liability” until the question is resolved and even in that event, the prior period liability needs to be addressed.
Preparing for the Future of AI Commerce
DepTax has been designed with these questions in mind, providing the ability to determine and control who collects the tax between multiple parties at every point in the transaction chain, simply, effortlessly and transparently.
Disclaimer: The views, statements or opinions expressed in this article are solely those of the author and do not represent tax advice and are not to be designated to be the views, statements or opinions of any other person, group, association or company.
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