LONDON — Google lost its final legal challenge on Tuesday against a European Union penalty for giving its own shopping recommendations an illegal advantage over rivals in search results, ending a long-running antitrust case that came with a whopping fine.

The European Union’s Court of Justice upheld a lower court’s decision, rejecting the company’s appeal against the 2.4 billion euro ($2.7 billion) penalty from the European Commission, the 27-nation bloc’s top antitrust enforcer.

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“By today’s judgment, the Court of Justice dismisses the appeal and thus upholds the judgment of the General Court,” the court said in a press release summarizing its decision.

Google didn’t respond immediately to a request for comment.

Read More: What Google’s Antitrust Defeat Means for AI

The commission’s original decision in 2017 accused the Silicon Valley giant of unfairly directing visitors to its own Google Shopping service to the detriment of competitors. It was one of three multibillion-euro fines that the commission imposed on Google in the previous decade as Brussels started ramping up its crackdown on the tech industry.

Google made changes to comply with the commission’s decision requiring it to treat competitors equally. The company started holding auctions for shopping search listings that it would bid for alongside other comparison shopping services.

At the same time, the company appealed the decision to the courts. But the E.U. General Court, the tribunal’s lower section, rejected its challenge in 2021 and the Court of Justice’s adviser later recommended rejecting the appeal.

European consumer group BEUC hailed the court’s decision, saying it shows how the bloc’s competition law “remains highly relevant” in digital markets.

“Google harmed millions of European consumers by ensuring that rival comparison shopping services were virtually invisible,” director general Agustín Reyna said. “Google’s illegal practices prevented consumers from accessing potentially cheaper prices and useful product information from rival comparison shopping services on all sorts of products, from clothes to washing machines.”

Google is still appealing the other two E.U. antitrust penalties, which involved its Android mobile operating system and AdSense advertising platform. The company was dealt a setback in the Android case when the E.U. General Court upheld the commission’s 4.125 billion euro fine in a 2022 decision. Its initial appeal against a 1.49 billion euro fine in the AdSense case has yet to be decided.

Those three cases foreshadowed expanded efforts by regulators worldwide to crack down on the tech industry. The E.U. has since opened more investigations into Big Tech companies and drafted new laws to clean up social media platforms and regulate artificial intelligence.

Google is now facing particular pressure over its lucrative digital advertising business. In a federal antitrust trial that began Monday, the U.S. Department of Justice is alleging the company holds a monopoly in the “ad tech” industry.

British competition regulators accused Google last week of abusing its dominance in ad tech while the E.U. is carrying out its own investigation.

Microsoft has relinquished its seat on the board of OpenAI, saying its participation is no longer needed because the ChatGPT maker has improved its governance since being roiled by boardroom chaos last year.

In a Tuesday letter, Microsoft confirmed it was resigning, “effective immediately,” from its role as an observer on the artificial intelligence company’s board.

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“We appreciate the support shown by OpenAI leadership and the OpenAI board as we made this decision,” the letter said.

The surprise departure comes amid intensifying scrutiny from antitrust regulators of the powerful AI partnership. Microsoft has reportedly invested $13 billion in OpenAI.

European Union regulators said last month that they would take a fresh look at the partnership under the 27-nation bloc’s antitrust rules while British competition watchdogs have also been looking into the deal.

Microsoft took the board seat following a power struggle in which OpenAI CEO Sam Altman was fired, then quickly reinstated, while the board members behind the ouster were pushed out.

“Over the past eight months we have witnessed significant progress by the newly formed board and are confident in the company’s direction,” Microsoft said in its letter. “Given all of this we no longer believe our limited role as an observer is necessary.”

With Microsoft’s departure, OpenAI will no longer have observer seats on its board.

“We are grateful to Microsoft for voicing confidence in the Board and the direction of the company, and we look forward to continuing our successful partnership,” OpenAI said in a statement.

It’s not hard to conclude that Microsoft’s decision to ditch the board seat was heavily influenced by rising scrutiny of big technology companies and their links with AI startups, said Alex Haffner, a competition partner at U.K. law firm Fladgate.

“It is clear that regulators are very much focused on the complex web of inter-relationships that Big Tech has created with AI providers, hence the need for Microsoft and others to carefully consider how they structure these arrangements going forward,” he said.

OpenAI said it would take a new approach to “informing and engaging key strategic partners” such as Microsoft and Apple and investors such as Thrive Capital and Khosla Ventures, with regular meetings to update stakeholders on progress and ensure stronger collaboration on safety and security.

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