Multiple studies suggest an association of marijuana use with increased rates of sexual risk behavior and sexually transmitted diseases (STDs). Most studies have focused on global associations of marijuana use with sexual risk outcomes and few have examined relevant cognitive variables. Adolescents in the juvenile justice system are at elevated risk for HIV/STDs and preliminary evidence suggests that marijuana is a potentially important cofactor for sexual risk behavior in this population. This study evaluated global, situational and event-level associations of marijuana use and sex-related marijuana expectancies with sexual risk outcomes in a large, racially diverse sample of adjudicated youth (n = 656, 66% male, mean age = 16.7 years). Cross-sectional and prospective analyses identified associations of marijuana use and dependence symptoms with sexual risk outcomes, including lower frequency of condom use and higher STD incidence. Stronger sex-related marijuana expectancies predicted greater intentions for and frequency of marijuana use in sexual situations. In event-level analyses that controlled for alcohol, marijuana use predicted a significantly decreased likelihood of condom use; this association was moderated by sex-related marijuana expectancies. Mediation analyses suggested that behavioral intentions partly accounted for the prospective association of expectancies with marijuana use before sex. These results provide further evidence that marijuana use is a potentially important cofactor for HIV/STD transmission in high-risk adolescents and suggest that cognitive factors could be important for characterizing this association. (PsycINFO Database Record (c) 2010 APA, all rights reserved)