Cannabis Social Clubs (CSCs) can be found in several countries in Europe and Latin America. However, Uruguay is the only country that offers a legal framework for their functioning: CSCs are one of the three supply models allowed under that country’s cannabis regulation. Differently, in Belgium, CSCs have remained unregulated and subject to criminal prosecution. This chapter draws on responses from two online surveys among CSC members in both Uruguay (2018–2019) and Belgium (2017). Our goals are to provide a comparative analysis of the sociodemographic profile and patterns of use of CSC members in the two countries, as well as of their views on cannabis policy. We found similarities across the two groups in terms of CSC members’ sociodemographic profile (mainly male, middle-class, educated users), and patterns of use (near daily or daily users). The Belgian respondents had a more positive view of the CSC regulatory framework introduced in Uruguay than their Uruguayan counterparts. The legal limitation to the number of members enrolled per CSC and the mandatory registration in a national database were particularly contentious issues among Uruguayan CSC members.