Attachment style differences in psychological symptomatology, self-concept, and risky or problem behaviors were examined in a community sample (N = 1,989) of Black and White adolescents, 13 to 19 years old. Overall, secure adolescents were the best-adjusted group, though not necessarily the least likely to engage in risky behaviors. Anxious adolescents were the worst-adjusted group, reporting the poorest self-concepts and the highest levels of symptomatology and risk behaviors. In contrast, avoidant adolescents reported generally high levels of symptomatology and poor self-concepts but similar levels of risk behaviors to those found among secures. Mediation analyses suggested that the observed differences in problem behaviors were at least partially accounted for by the differential experience of distress symptoms (primarily hostility and depression) and by social competence. Finally, patterns of attachment effects were similar across age, gender, and racial groups, with some important exceptions.