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The United States has an uncomfortable relationship with pleasure. Cultural ambivalence is evident in discourses surrounding pleasure and the labeling and treatment of those who act on their desires. Pleasure seeking, generally understood in moral terms, is often medicalized and criminalized (as in the case of pregnancy prevention and drug use), placing questions of how to manage pleasure under the purview of medical and legal actors. At the macrolevel, institutions police pleasure via rules, patterns of action, and logics, while at the microlevel, frontline workers police pleasure via daily decisions about resource distribution. This chapter develops a sociolegal framework for understanding the social control of pleasure by analyzing how two institutions – medicine and criminal justice – police pleasure institutionally and interactionally. Conceptualizing medicine and criminal justice as paternalistic institutions acting as arbiters of morality, I demonstrate how these institutions address two cases of pleasure seeking – drug use and sex – by drawing examples from contemporary drug and reproductive health policy. Section one highlights shared institutional mechanisms of policing pleasure across medicine and criminal justice such as categorization, allocation of professional power, and the structuring of legitimate consequences for pleasure seeking. Section two demonstrates how frontline workers in each field act as moral gatekeepers as they interpret and construct institutional imperatives while exercising discretion about resource allocation in daily practice. The chapter concludes with a discussion of how understanding institutional and interactional policing of pleasure informs sociolegal scholarship about the relationships between medicine and criminal justice and the mechanisms by which institutions and frontline workers act as agents of social control.