Scholars have identified policing and hyper-incarceration as key mechanisms to reproduce racial inequality and poverty. Existing research, however, often overlooks how policing practices impact gender and sexuality, especially expansive expressions of gender and non-heterosexuality. This lack of attention is critical because lesbian, gay, bisexual, transgender, and queer (LGBTQ) people disproportionately experience incarceration, including LGBTQ youth who are disproportionately incarcerated in juvenile detention. In this article, I draw on 18 months of ethnographic fieldwork and 40 in-depth interviews with LGBTQ youth experiencing homelessness to address this gap in the literature by documenting how police and other agents of the state use their discretion to regulate youth’s gender expressions, identities, and sex lives. I posit that current policing patterns of discrimination operate primarily not through de jure discrimination against LGBTQ people but as de facto discrimination based on discretionary hyper-incarceration practices that police gender, sexuality, and LGBTQ people. I contend that policing is not only about maintaining racial inequality and governing poverty but also about controlling and regulating gender and sexuality, especially the gender and sexuality of poor LGBTQ people of color.