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The relationships among intra-individual vulnerability, stress, and adjustment were assessed within a sample of 621 young adolescents from a predominantly affluent suburban area. Also considered was the extent to which gender and family structure influenced the prevalence of these three conditions. Vulnerable teenagers were distinguished from their peers based on their inability to effectively manage the developmental task of individuation. The components of the individuation process considered included ego and cognitive autonomy, and parent and peer relatedness. Stress was measured based on self-reported exposure to conditions of threat, demand, or structural constraint. Indices of depression, problem behaviors, school performance, school absences, and teacher perceived risk were utilized to assess adjustment. Consonant with hypotheses that pronounced difficulty resolving a developmental task is characteristic of vulnerable individuals and that exposure to numerous psychosocial stressors puts individuals at-risk for maladjustment, adolescents who were either poorly individuated or highly stressed exhibited greater dysfunction than their peers. Also individuated or highly stressed exhibited greater dysfunction than their peers. Also consistent with expectations, the poorest overall adjustment was exhibited by vulnerable adolescents who were exposed to multiple stressors. Gender and family structure affected the incidence of vulnerability, elevated exposure to stress, and maladjustment. However, the impact of gender was inconsistent with hypotheses, as girls were found to be at lower risk for dysfunction than boys.