This dissertation examines Puerto Rican therapeutic communities – resource-poor mutual-aid collectives that have flourished over the past five decades, despite being heavily criticized by human rights groups for using unwaged labor as a method to treat addiction. The persistence of these communities, which are spreading rapidly across Latin America, is widely ascribed in international media to state neglect. I conducted a year of ethnographic research in Puerto Rico to understand why labor therapies thrive, and what these approaches are intended to achieve among those who practice them. Challenging the argument that labor therapies are the simple result of the state failing to provide alternatives, my research shows that during the last half century therapeutic communities have been successively recruited to serve a variety of distinct and sometimes competing interests. My examination of the multiple, contested, and sometimes-converging projects that inhere within this therapeutic regime shows that these organizations have variously served as entrepreneurial projects of informal enterprise, existential projects of redemption, state projects of containment, and shunt-valves for relieving burdens of dependency from straining kinship systems. Their endurance, therefore, not only reflects their capacity to patch the cracks of multiple faltering systems (including employment, corrections, family), but it also reflects their protean vulnerability to appropriation: that is, the ease with which they are co-opted by other actors for alternative utilities. Based on eight months of intensive participant observation in one therapeutic community, La Casita, where I explored the cultural logics and meanings of labor therapies, I argue that “drug treatment” here is not centrally geared towards “treating addiction.” Instead, La Casita’s therapeutic practices of labor therapy, time-discipline, prayer, and internal work are more instructively read as social technologies through which men who are excluded from the labor market and estranged from kinship ties seek to cultivate an alternative masculinity that restores their sense of worth. The “socially useful” masculinity under construction here, based on a performance of work, responsibility, and duty, offers unemployed men an alternative way to claim the dignity and social membership of work.