Context: Understanding the interplay of multiple contexts of adolescents' sexual risk behaviors is essential to helping them avoid pregnancy and STDs. Although a body of research has identified multiple individual- and family-level variables associated with adolescents' sexual risk behaviors, relatively few studies have examined relationships between these behaviors and latent indicators of unstable, chaotic environments. Methods: In 2007-2008, a sample of 241 sexually active adolescent females who were at high risk for pregnancy and STDs were recruited through two school-based clinics and two community clinics in Minneapolis and St. Paul. Confirmatory factor analysis was used with baseline data to specify latent constructs of individual risk and family disengagement. Structural equation models examined longitudinal relationships between baseline measures of these constructs and sexual risk behaviors assessed six months later. Results: The latent construct of individual risk encompassed substance use, violence perpetration, violence victimization and having witnessed violence; that of family disengagement included family disconnection, poor family communication and perceived lack of safety at home. Baseline level of individual risk was positively associated with number of male sex partners six months later (path coefficient, 0.2); it was not associated with consistent condom use at follow-up. Level of family disengagement was negatively associated with condom use consistency six months later (-0.3), but was not associated with number of male sex partners. Conclusions: To meet the health needs of vulnerable adolescents, health systems should incorporate coordinated and interdisciplinary services that acknowledge adolescents' relevant familial and social contexts.