Through in-depth interviews, this study examined the relational context of sexual HIV risk for 10 Black women aged 18-30 who were defendants in a community court setting. A qualitative data analysis identified themes of actual and feared intimate partner violence (IPV) and the expectations of demonstrating trust in a relationship as obstacles to negotiating the use of condoms. The findings speak to the broader structural factors and consequences of IPV and drug use. The article discusses the implications for HIV prevention for Black women who are involved in the criminal justice system.