The cases had established the European Union as the world’s leading tech watchdog, but have since raised questions about its protracted appeals process.

The European Union’s highest court on Tuesday delivered a major victory in the bloc’s yearslong campaign to regulate the technology industry, knocking down appeals by Apple and Google in two landmark legal cases.

The decisions, issued by the Court of Justice of the European Union, bolster efforts in the region to clamp down on the world’s largest technology companies. Apple and Google have been frequent targets for E.U. regulators, and the companies have battled the cases for years.

In the Apple case, the court sided with a European Union order from 2016 for Ireland to collect 13 billion euros, worth about $14.4 billion today, in unpaid taxes from the company. Regulators determined that Apple had struck illegal deals with the Irish government that allowed the company to pay virtually nothing in taxes on its European business in some years.

Apple won an earlier decision to strike down the order, a ruling that the European Commission, the E.U.’s executive branch, appealed to the Court of Justice.

In the Google case, the court agreed with the commission’s 2017 decision to fine the company €2.4 billion for giving preferential treatment to its own price-comparison shopping service over rival offerings. Google lost an appeal in 2021.

When the European Union penalized Apple and Google, the cases represented a major shift in how the tech industry was regulated. Until then, governments around the world had largely taken a hands-off approach to tech oversight as Apple, Google, Amazon and Facebook — now renamed Meta — ballooned in size and remade how people live, work, shop and communicate.

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