Amazon vs. Perplexity: The Battle That Could Reshape How AI Shops for You

A legal showdown between e-commerce giant Amazon and AI startup Perplexity is raising fundamental questions about the future of autonomous shopping agents online.

The gloves are off. Amazon has fired what could be the opening salvo in a much larger war over how artificial intelligence operates on the internet. The target? Perplexity AI, a buzzy AI startup that’s been letting its browser do something Amazon really doesn’t like—shopping on its platform without permission.

This isn’t just another tech spat. It’s a clash that could define whether your AI assistant has the right to buy things for you online, or whether companies like Amazon get to decide who or what shops on their digital shelves.

The Cease-and-Desist Heard Round Silicon Valley

On October 31, 2025, Amazon sent Perplexity a strongly worded cease-and-desist letter. The message was clear: stop letting your Comet browser make purchases on our platform. Now.

According to Bloomberg, Amazon accused Perplexity of computer fraud. The e-commerce behemoth claimed the AI startup failed to disclose when its agents were shopping on behalf of real people. Amazon’s legal team didn’t mince words they compared Comet’s actions to those of an “intruder,” arguing that just because the intrusion involves code “makes it no less unlawful.”

But here’s where it gets interesting. Perplexity didn’t back down. Instead, the company published a blog post with a title that pulls no punches: “Bullying is not innovation.”

The AI startup fired back, accusing Amazon of using legal threats and intimidation to squash competition. “This week, Perplexity received an aggressive legal threat from Amazon,” the company wrote. “This is Amazon’s first legal salvo against an AI company, and it is a threat to all internet users.”

What Exactly Is Comet Doing?

Let’s break this down. Perplexity’s Comet browser isn’t your typical web browser. It’s powered by artificial intelligence that can actually do things for you not just show you web pages.

Want to buy a new coffee maker? You could tell Comet, and it would search Amazon, find options, and complete the purchase. All without you clicking through product pages, reading reviews, or entering payment information. The AI handles everything.

Sounds convenient, right? Amazon doesn’t think so.

The e-commerce giant argues that Comet “significantly degraded the shopping and customer service experience.” Amazon spokesperson Lara Hendrickson said third-party AI services must “operate openly and respect a service provider’s decision whether or not to participate.”

According to Amazon, Comet was disguising itself to look like an ordinary Chrome browser user. The company claims this deception violates its terms of service, which explicitly prohibit “data mining, robots, or similar extraction tools.”

The Timeline of Tension

This dispute didn’t just pop up overnight. It’s been brewing for a while.

Sources familiar with the matter told Bloomberg that Amazon first warned Perplexity back in November 2024 to stop using AI agents for purchases until the companies could reach an agreement. Perplexity initially complied.

But by August 2025, Comet was back in action. This time, Amazon alleges, the browser was masquerading as Google Chrome to avoid detection. When Amazon blocked it, Perplexity allegedly released an updated version designed to circumvent the restriction.

It’s like a high-tech game of cat and mouse, except the stakes are billions of dollars and the future of online commerce.

Follow the Money: Why Amazon Really Cares

Sure, Amazon talks about customer experience and transparency. But there’s an elephant in the room that Perplexity is more than happy to point out: advertising revenue.

Amazon’s advertising business is massive. We’re talking tens of billions of dollars. The company makes money by showing you sponsored products, upselling you on premium options, and generally guiding your purchasing decisions through carefully curated recommendations.

Perplexity argues that Amazon’s real concern isn’t customer experience it’s losing control over the shopping journey. “Amazon should love this,” Perplexity wrote. “Easier shopping means more transactions and happier customers. But Amazon doesn’t care. They’re more interested in serving you ads, sponsored results, and influencing your purchasing decisions with upsells and confusing offers.”

Think about it. If an AI agent is doing your shopping, it’s not seeing those sponsored product placements. It’s not getting tempted by “customers who bought this also bought” suggestions. It’s just finding what you asked for and buying it. Efficient? Yes. Profitable for Amazon? Not so much.

The Irony of It All

Here’s where this story gets deliciously ironic. Perplexity isn’t just some random startup Amazon is battling. The two companies have a relationship.

Perplexity is an Amazon Web Services customer. According to CEO Aravind Srinivas, the startup has made “hundreds of millions” in spending commitments with AWS. Amazon even showcased Perplexity as a success story at its 2023 cloud conference.

And it gets better. Jeff Bezos, Amazon’s founder, is an investor in Perplexity through his Bezos Expeditions Fund.

So Amazon is essentially suing a company that pays it millions of dollars and is backed by its founder. You can’t make this stuff up.

Amazon’s Own AI Shopping Ambitions

Before you think Amazon is anti-AI shopping, think again. The company has been developing its own AI-powered shopping assistants.

In February 2025, Amazon rolled out Rufus, a shopping chatbot that can answer questions and suggest products. In April, it began testing “Buy For Me,” a feature that lets shoppers purchase products from other websites without leaving Amazon’s app.

During Amazon’s recent earnings call, CEO Andy Jassy told investors the company is “having conversations” with builders of third-party AI shopping tools and may ultimately partner with them. But he added a crucial caveat: “We have to find a way, though, that makes the customer experience good.”

Translation? Amazon wants AI shopping agents on its platform as long as Amazon controls them.

Perplexity’s Defense: The Wrench Analogy

Perplexity’s legal argument is… creative. The company compares AI agents to wrenches.

“For the last 50 years, software has been a tool, like a wrench in the hands of the user,” Perplexity wrote. “But with the rise of agentic AI, software is also becoming labor: an assistant, an employee, an agent.”

The company argues that just as corporations can’t stop you from owning wrenches, they shouldn’t be able to stop you from “hiring” AI labor to act on your behalf.

“The law is clear that large corporations have no right to stop you from owning wrenches,” Perplexity continued. “Today, Amazon announced it does not believe in your right to hire labor, to have an assistant or an employee acting on your behalf.”

It’s a bold argument. Whether it holds up in court is another question entirely.

What Legal Experts Are Saying

The legal landscape here is murky at best. Santa Clara University law professor Eric Goldman told The Register that “the courts are in complete chaos” on questions of web scraping and automated access, especially after the U.S. Supreme Court’s decision in Van Buren v. United States.

“Nobody really knows anything about the legitimacy of scraping today,” Goldman said. “Distinguishing between web browsing, scraping, and agentic AI access is going to be extremely difficult for the law.”

Goldman pointed out that Amazon could potentially restrict how users share their credentials in its terms of service. If Amazon did that, users who share their login information with Comet would be in breach of their agreement, and Perplexity might face additional liability.

But there’s a catch. If Amazon takes too hard a line, it could alienate users who actually value having AI assistants shop for them. Goldman compared the situation to carriage contract battles between cable TV companies and broadcasters.

“It’s like one of those things where both sides are going to have to bleed before they realize that they’re better off working together,” he said.

The Bigger Picture: What This Means for AI

This dispute isn’t really about Perplexity or Amazon. It’s about the future of how AI operates online.

We’re entering an era where AI agents can do more than just answer questions or generate text. They can take actions on your behalf booking flights, making reservations, and yes, shopping. Companies like OpenAI, Google, and Anthropic are all developing similar capabilities.

The case, Amazon.com Services LLC v. Perplexity AI Inc., could set the first court precedent defining how “agentic AI” is allowed to act autonomously within commercial online ecosystems.

If Amazon wins, it could establish that websites have broad authority to block AI agents, even when those agents are acting on behalf of legitimate users. That could slow the development of AI assistants and keep more control in the hands of big platforms.

If Perplexity wins, it could open the floodgates for AI agents to operate more freely across the web. That might be great for innovation and user convenience, but it could also disrupt business models that rely on controlling the user experience.

Perplexity’s Troubled History

This isn’t Perplexity’s first rodeo with controversy. The company has faced criticism before for how it uses online content.

Earlier this year, Cloudflare published research accusing Perplexity of scraping websites while specifically defying requests from websites blocking AI bots. Publishers and Reddit have also accused the company of using content in its AI summaries without permission.

Perplexity has consistently defended itself, arguing it “fights for users’ rights to freely access public knowledge.” But the pattern of disputes suggests the company has a habit of pushing boundaries and not everyone appreciates it.

What Happens Next?

As of now, Perplexity hasn’t publicly stated whether it will comply with Amazon’s demand. The company’s blog post suggests it’s digging in for a fight.

“Amazon also forgets how it got so big,” Perplexity wrote. “Users love it. They want good products, at a low price, delivered fast. Agentic shopping is the natural evolution of this promise, and people already demand it. Perplexity demands the right to offer it.”

Amazon, for its part, has already published its cease-and-desist letter, making its position crystal clear. The company isn’t backing down either.

This could end up in court, where a judge would have to grapple with questions that don’t have clear answers yet. Or the two companies could reach some kind of agreement perhaps with Perplexity paying Amazon for access or agreeing to certain restrictions on how Comet operates.

The Consumer Perspective

Lost in all this corporate drama is a simple question: what do consumers actually want?

According to a February 2025 survey by Omnisend, 66 percent of consumers refuse to let AI make purchases for them, even if it promises better deals. That suggests most people aren’t ready to hand over their credit cards to AI agents just yet.

But preferences change. Email was once considered impersonal and inappropriate for business communication. Now it’s the default. Maybe AI shopping agents will follow a similar trajectory.

Or maybe people will always want to maintain control over their purchasing decisions. After all, shopping isn’t always just about efficiency. Sometimes it’s about browsing, discovering, and the experience itself.

A Precedent-Setting Battle

Whatever happens, this case matters. It’s one of the first major legal battles over how AI agents should operate in commercial spaces online.

The outcome could influence how other companies from airlines to restaurants to retailers handle AI agents. It could shape the terms of service agreements we all click through without reading. And it could determine whether the future of online commerce is controlled by platforms or distributed among AI assistants.

For now, the battle lines are drawn. Amazon says Perplexity is an unauthorized intruder. Perplexity says Amazon is a bully trying to stifle innovation. Both companies have billions of dollars and strong incentives to win.

The rest of us? We’re just watching to see who gets to decide how we shop in the age of AI.