Cocaine users routinely engage in high-risk sexual behaviors that place them at an elevated risk of contracting HIV and other blood-borne infections. The purpose of the present study was to compare trading sex for drugs and/or money, having 10 or more sexual partners in 1 year, and sexually transmitted diseases (STDs) of cocaine-dependent individuals in treatment for their dependence across race and gender and against participants who live in their community. Cocaine-dependent individuals (n = 459) were identified through nine publicly and privately funded inpatient and outpatient chemical dependency treatment centers in the St. Louis area during 2001-2006. Community-based participants (n = 459) were matched to cocaine-dependent participants on age, ethnicity, gender, and zip code of residence. Mean age of the sample was 36 years old, 50% were Caucasians, 50% were African American, and 47% were male. Nearly half of cocaine-dependent participants in treatment had traded sex for drugs and/or money and over one-third had more than 10 sexual partners in 1 year with a risk concentrated among African Americans even after controlling for income and educational attainment. Participants recruited from the community with some exposure to cocaine reported similar rates of high risk sexual behaviors as the cocaine dependent subjects from treatment settings. It is important for clinicians to recognize that once released from treatment, cocaine-dependent individuals may be returning to high-risk environments where sexual risk behaviors are occurring in the context of cocaine use.