Severely mentally ill youths are at elevated risk for human immunodeficiency virus (HIV) infection, but little is known about AIDS risk behavior in adolescents who seek outpatient mental health services or about the links between psychiatric problems and particular high-risk behaviors. This pilot study used structural equation modeling to conduct a path analysis to explore the direct and indirect effects of adolescent psychopathology on risky sex, drug/alcohol use, and needle use. Study participants were youths (n=86) and caregivers/parents (n=81) who sought outpatient mental health treatment at a Chicago hospital. Youths reported their relationship attitudes, peer influence, sexual behavior, and drug/alcohol use. Results revealed high rates of risky behavior in this population and unique links between specific types of psychopathology and different risk behaviors, but the importance of key contextual factors (i.e., informant, type of psychopathology, kind of risk behavior) were underscored in understanding the influence of psychopathology on AIDS risk. Externalizing problems, reported by adolescents, were significantly related to teenagers’ drug/alcohol use, needle use, and risky sex, and neither parent or adolescent reported internalizing problems as being significantly associated with any high-risk behavior. This was a pilot study and results should be interpreted cautiously. Further research was suggested to identify other factors associated with AIDS risk in troubled youth. The results in this study were restricted to adolescents who sought outpatient mental health services.