The convenience, 24/7 availability, perceived anonymity and innovation in online gambling have resulted in more widespread consumption of such services. This increased pervasiveness is coupled with challenges in effectively regulating such online gambling services. Regulatory objectives in the regulation of online gambling are containing gambling addiction (as a public health matter), protection of minors, consumer protection (in particular minimising misleading advertising and unfair commercial practices), upholding the integrity of sports (preventing sports manipulation such as match-fixing), preventing money laundering and fighting crime more generally (fraud, organised crime). While the seriousness of potential harms stemming from unauthorised online gambling underlines the importance of these regulatory objectives, there are significant challenges for the enforcement of online gambling regulation. The enforcement challenges of effectively regulating online services are mainly due to the cross-border nature of such services and the limited jurisdictional reach of national regulators and enforcers. But other aspects of online interaction also play an important role, such as the virtual nature of online gambling facilities, the complex eco-system of service providers (which is a direct consequence of the degree of innovation in the field of internet technologies and business methods: cloud computing, affiliate networks, advertising networks monetizing online profiling, social media, payment services), as well as the immediacy of internet communication. Given the transnational nature of these challenges, it makes sense to examine the effectiveness of regulation at an EU/EEA level. Within the EU/EEA there is a patchwork of national regulation and in this patchwork, States uphold differing regulatory regimes and standards in relation to the challenges which online gambling produces. Regulation is fragmented, but, while the objectives of each national regulatory regime vary, they are also very broadly similar. The same can be said for the (extra-territorial) pressures which unauthorised gambling services place on attaining national regulatory objectives. Therefore, all EU/EEA Member States are seeking to optimise effective enforcement tools and the ability to channel demand towards the locally authorised offer.