Europe’s highest court has ruled against Apple in the tech giant’s 10-year legal battle over its Irish tax affairs.

The European Court’s announcement comes just hours after Apple unveiled a slew of new products including the iPhone 16.

Immediately after the court decision, the company’s shares fell 1% in preliminary trading.

In 2014, the European Commission launched an investigation into Apple’s tax payments in Ireland, the tech giant’s EU headquarters. In 2016, the Commission ordered Dublin to recover up to €13 billion in back taxes from Apple, saying at the time that the tech company had received “illegal” tax benefits from Ireland over two decades.

Apple and Ireland appealed the Commission’s decision in 2019, and in 2020 the EU General Court sided with the US tech giant. The EU’s second highest court overturned the Commission’s 2016 decision and said the executive branch had failed to prove that the Irish government had given Apple a tax advantage.

The Commission in turn appealed against the decision of the General Court, sending the appeal to the ECJ.

The ECJ on Tuesday overturned the General Court’s decision and upheld the Commission’s original 2016 decision.

The case, first brought under outgoing competition chief Margrethe Vestager, highlights the ongoing conflict between US tech giants and the EU, which has tried to tackle issues from data protection to taxation and antitrust.

It wasn’t the last time Apple was targeted by the EU. Most recently, the Commission slapped Apple with an antitrust fine of €1.8 billion in March for abusing its dominant position in the music streaming app distribution market.