In a significant ruling, Europe’s top court on Tuesday decided against Apple in its decade-long legal battle over a $14.4 tax bill in Ireland.

The European Court of Justice’s decision marks a major setback for the tech giant, which has been fighting the European Commission’s 2016 order for Dublin to recover back taxes from the company.

The Commission initially accused Apple of receiving “illegal” tax benefits from Ireland over two decades.

While Apple and the Irish government successfully appealed in 2020, the Commission escalated the case, leading to this latest ruling.

The decision underscores ongoing tensions between US tech firms and the European Union, which continues to push for stronger regulations on issues such as taxation and antitrust.