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Europe’s top court on Tuesday ruled against Apple in the tech giant’s 10-year court battle over its tax affairs in Ireland.

The pronouncement from the European Court of Justice comes hours after Apple unveiled a swathe of new product offerings, looking to revitalize its iPhone, Apple Watch and AirPod line-ups.

CNBC has reached out to Apple for comment. The company’s shares were down 1% in premarket trading at 09:07 a.m. London time.

In 2014, the European Commission, the European Union’s executive arm, opened an investigation into Apple’s tax payments in Ireland, the tech giant’s headquarters in the EU.

The Commission in 2016 ordered Dublin to recover up to 13 billion euros ($14.4 billion) in back taxes from Apple, at the time saying that the tech company had received “illegal” tax benefits from Ireland over the course of two decades.

Apple and Ireland appealed the Commission’s decision in 2019, and in 2020 the EU General Court sided with the U.S. tech giant. The EU’s second-highest court anulled the Commission’s 2016 decision and said that the executive arm did not prove that the Irish government had given Apple a tax advantage.

The Commission in turn appealed the General Court’s decision, sending the litigation up to the ECJ.

The ECJ on Tuesday set aside the General Court’s decision and confirmed the Commission’s original 2016 ruling.

The case, which first began under outgoing competition chief Margrethe Vestager, highlights the continued conflict between U.S. tech giants and the EU, which has sought to tackle issues from data protection to taxation and antitrust.

This was not the last time that Apple found itself in the EU’s crosshairs. Most recently, the Commission hit the iPhone maker hit Apple with an antitrust fine of 1.8 billion euro ($1.99 billion) in March for abusing its dominant position in the market for the distribution of music streaming apps.

Separately, the EU’s sweeping Digital Markets Act has forced companies to change some of their practices in Europe. The Commission has opened various investigations under the DMA into tech giants, including Apple, Alphabet and Meta.

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