In 1961, several mass organizations in Cuba collaborated as Fidel Castro launched a national campaign against prostitution. By 1965, only four years later, the Revolution proclaimed “the elimination of prostitution” in Cuba. This article examines the Cuban Revolution’s national campaign to end prostitution as a case study to investigate how gender and patriarchy affect the ways social change is operationalized. Interested in the relationship between social and cultural change, following the tradition of feminist historians, this article utilizes the oral histories of two Cuban federada women involved in the State’s campaign to consider how the Revolution’s macro program was implemented and carried out at micro level. The narratives of these local agents in the everyday spaces of the campaign provide a bottom-up lens which can be juxtaposed with the Revolution’s proclaimed “success.” These testimonios detail how gender and patriarchy played out on the ground, limiting the campaign’s efforts toward social change, therefore demonstrating the tensions and contradictions of how social change is exercised within human agency and constraint.