When is data truly anonymous, and when does it still fall under the strict mandates of the GDPR? In this article, Danny Hoekzema examines the fundamental conflict between European regulators and the judiciary. While regulators maintain a strict, absolute approach, the courts favor a contextual test: is re-identification practically and legally feasible for the specific recipient?. Hoekzema analyzes the impact of this legal uncertainty on data sharing and innovation, while looking ahead to a landmark ruling from the European Court of Justice that is expected to define the rules of the game for our digital society once and for all.