Based upon 50 interviews that took place over the course of 3 years of ethnographic research with 100 female street-based sex workers in Denver, Colorado, the tenth largest city in the United States, this article explores the cultural ethos informing women’s interactions with police and the tools women use to navigate their struggles with homelessness, addiction, and the everyday violence of the street. It identifies three beliefs about patrol officers that reflect the complexities of women’s interactions with police: arrest is indiscriminate in a “known prostitution area,” arrest avoidance strategies necessitate interpreting behavioral cues while showing respect to officers and forming affective bonds with potential clients, and officers may abuse their authority. This belief system is part of an environment in which women’s stigmatized behaviors are highly visible and constitute an increased risk of negative police encounters. Changes to policing practices remain unlikely while women’s sex work and drug use activities remain criminalized. Findings presented support arguments for decriminalizing prostitution as well as the implementation of harm reduction-oriented social policy, including services that inform women about their rights in the criminal justice system while facilitating awareness of how their individual lives intersect with gender, class, and racial bias in a sociolegal system that stigmatizes and criminalizes their choices.