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

Google has lost its final legal challenge against a European Union penalty for giving its own shopping recommendations an illegal advantage over rivals in search results, ending a long-running antitrust case that came with a whopping fine.

The European Court of Justice said Apple must repay about $14.35 billion after reaping illegal tax benefits in Ireland and backed a $2.65 billion antitrust fine on Google.