Adolescents in psychiatric care are at increased risk of HIV, yet little is known about the family factors related to sexual risk taking among these youth. We explored whether perceived parental monitoring and perceived parental permissiveness were linked to high-risk sexual behavior in 169 ethnically diverse urban youth seeking mental health services in Chicago, and we tested whether adolescent gender moderated these associations. We evaluated sexual risk taking at a global level and for specific risk behaviors (e.g., sex without a condom, sex while using drugs and alcohol). Girls reported more risky sex overall than boys, and girls were more likely than boys to report having sex without a condom. At low levels of parental permissiveness, rates of risky sex among boys and girls’ did not differ, but at high levels of permissiveness girls reported more sexual risk taking than boys, and girls were more likely than boys to report having sex while using drugs and alcohol and having sex without a condom. Findings highlight the complexity of adolescent sexual behavior and the need for multilevel assessment of risk taking. Results suggest that parental monitoring and permissiveness are more strongly associated with sexual risk taking in troubled girls than troubled boys, and they underscore a need for gender-sensitive, family-focused HIV-prevention programs.