This chapter explores how the imposition of unprecedented sanctions against Russia following the large-scale invasion of Ukraine in 2022 and the constant cat-and-mouse game of enforcement and evasion that ensued have altered the secondary sanctions landscape. More specifically, it examines to what extent, notwithstanding its longstanding and entrenched opposition to far-reaching US secondary sanctions, the European Union has gradually moved towards adding a ‘secondary’ layer to its own sanctions toolbox. The chapter first exposes the EU’s ambiguity towards extraterritoriality, both within and without the sanctions domain. It subsequently zooms in on a number of specific EU measures, namely the imposition of the so-called ‘price cap’ on Russian oil, the adoption of far-reaching import and export restrictions, including the prohibition to import certain Russian products even after these are located or have already been processed in third countries, and the threat of financial sanctions against, and criminal prosecution of, non-EU persons that facilitate the circumvention of EU sanctions against Russia. It then offers some concluding observations.