Sex work is a common phenomenon of Johannesburg's everyday city life, and sex workers themselves are often victims of crime. Nonetheless, sex work remains illegal and police are obligated to enforce the laws that prohibit sex work. This raises the question of how the South African Police Service has been coping with the complex task of policing street-based sex work. South African history, culture, and values about sexuality, gender, and the role of police are all explored to understand this complex relationship. The history of violence in the South African Police Service may provide a context for understanding how past models of policing that were rife with human rights abuses influence, if at all, how sex workers are policed today. Additionally, gendered attitudes about women and the history of the regulation of sex work and sexuality are relevant to understanding how the police relate with sex workers. The research aims to capture the perspective from the side of the police, and aims at getting a good understanding of the challenges the police face in light of a highly complex and often contradictory reality. The research employs legal ethnography to explore the ways that law, culture, and history operate in the everyday reality in the policing of sex work.