As the world gets smaller, and our marketplace is expanded digitally to include the entire world, businesses will increasingly encounter questions of legal compliance in the face of multi-jurisdictional transactions. Unlike in other industries, regulation of digital transactions has not seen multilateral treaties or uniform agreements between nations. This is due not only to the differing rates of technological progress from one nation to the next, but also for by reason of political or cultural differences—e.g. when dealing with expectations of privacy. As a result, laws are enacted with varying focus and coverage from one jurisdiction to another—yet with a commonality of extraterritoriality. These different laws generally seek to apply not only within each nation’s borders, but also to address cross-border transactions affecting their citizens and economies. Our presentation will identify the most pressing issues affecting cross border digital transactions against the backdrop of extraterritoriality and international enforcement, to offer possible strategies for navigating the muddled legal waters of international digital commerce.