Juvenile drug court (JDC) offenders have benefited from evidence-based interventions addressing antisocial behavior, mental health, and substance use; however, interventions addressing HIV risk behavior are lacking. This study presents pilot findings and lessons learned from a group-based HIV prevention intervention delivered to JDC offenders. Participants were randomized to a five-session HIV prevention (n = 29) or health promotion (n = 28) condition and completed measures of sexual risk taking and substance use at baseline and 3 months postintervention. No between-group differences by time emerged on measures of sexual risk taking or other HIV-related behaviors and attitudes. Both groups improved their rates of HIV testing and decreased their substance use during sex over time. Delivering an HIV prevention intervention to drug court offenders is feasible; however, more intensive interventions that incorporate multiple systems and address co-occurring mental health difficulties may be needed to effect sexual behavioral change among these high-risk court-involved youth.