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 delivered the 27-nation bloc a major victory on Tuesday in its yearslong campaign to regulate the technology industry, ruling against Apple and Google in two landmark legal cases.

The decisions, issued by the Court of Justice of the European Union, were seen as an important test of efforts in Europe 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 with appeals.

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

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