The European Union's stance on the extraterritorial reach of its sanctions has evolved recently, particularly in response to the need to prevent circumvention of restrictive measures against Russia. This article examines the legal basis and challenges associated with the "Best Efforts" obligation and the "No Re-export clause". While these provisions impose contractual and compliance obligations on EU-based companies, they also raise questions about their extraterritorial enforcement, legal consistency, and the potential for legal challenges before EU and international courts. By analyzing the intersection between EU sanctions laws, international jurisdiction principles, and corporate liability, this article explores how these new measures might be challenged and what legal arguments could be used to contest their enforcement beyond EU borders.