This study examined the utility of cognitive and behavioral constructs (AIDS information, motivation, and behavioral skills) in explaining sexual risk taking among 172 12-20-year-old ethnically diverse urban youths in outpatient psychiatric care. Structural equation modeling revealed only moderate support for the model, explaining low to moderate levels of variance in global sexual risk taking. The amount of explained variance improved when age was included as a predictor in the model. Findings shed light on the contribution of AIDS information, motivation, and behavioral skills to risky sexual behavior among teens receiving outpatient psychiatric care. Results suggest that cognitive and behavioral factors alone may not explain sexual risk taking among teens whose cognitive and emotional deficits (e.g., impaired judgment, poor reality testing, affect dysregulation) interfere with HIV preventive behavior. The most powerful explanatory model will likely include a combination of cognitive, behavioral, developmental, social (e.g., family), and personal (e.g., psychopathology) risk mechanisms.