Greater empirical attention directed toward gender-sensitive assessment strategies that concentrate on family-specific factors is thought to be both timely and necessary, especially with regard to outcome variables associated with mental health and substance abuse in at-risk adolescent populations. A sample of 2,646 court-involved adolescents was used to test two competing models regarding relationships among disruptive family processes, mental health (as both internalizing and externalizing problems), and substance abuse issues according to gender. The results of multiple group structural equation modeling procedures indicated that disrupted family processes were significantly associated with higher levels of internalizing problems, externalizing problems, and substance abuse in both male and female youth. For females, however, disrupted family processes were more related to internalizing problems and substance abuse than externalizing problems. Further, the relationship between disrupted family processes and substance abuse was not mediated by mental health issues, indicating a lack of support for the alternative model tested in this study. Together, the findings underscore the primacy of the family’s impact on issues related to adolescent development and well-being in tandem with the need for a more gender sensitive approach to the needs of court-involved males and females.