Crack and cocaine use among adults has been associated with co-occurring psychiatric disorders as well as other drug use and unprotected sex. However, this issue is relatively unstudied in adolescents. This study collected data from 282 adolescents (mean age = 14.9 years) treated in intensive psychiatric treatment settings to understand the relationship between crack/cocaine use and HIV risk. Thirteen percent of youths reported ever using crack or cocaine. Use was not associated with age, gender, race/ethnicity, or SES. After controlling for known factors that influence unprotected sex, the odds that those with a history of crack/cocaine use engaged in inconsistent condom use was six times greater than that for those youths who did not ever use. Thus, crack/cocaine use is prevalent even among younger adolescents with psychiatric disorders who are not in drug treatment. Its use is associated with high rates of sexual and other risk behaviors. A history of use should alert clinicians to a wide variety of possible behavioral risks. These results can also inform future adolescent HIV prevention intervention development. (Contains 3 tables.)