My thesis aims to provide a cross-national analysis of the effect that a country’s drug policy, and law enforcement strategies, has on the cannabis market. Several countries’ over the past 15 years have taken a more de-regulation position towards cannabis. For instance, Argentina and Portugal both decriminalised cannabis use in 2009 and 2001 respectively. Several states in America have legalised, or have recently voted to begin the process of legalising recreational cannabis use. Canada also intends to legalise cannabis’s usage in 2018. However, prohibition remains a popular approach towards cannabis for many countries and jurisdictions. Despite the existence of alternate policy regimes and different enforcement strategies on the cannabis market, few insights have been gained from cross-country comparison. Furthermore, previous studies in this area often focus on one singular location, intervention, and on enforcement or regulation. My thesis intends to provide a comprehensive analysis of both regulation and law enforcement’s effects from multiple interventions and locations on cannabis. The possible findings from my research will have implications for drug policy makers, law enforcement, and the on-going debate over cannabis legality.