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The purpose of this study was to determine the relations between multiple forms of attachment and adolescent risk-taking, academic achievement, internalizing behaviors, and externalizing behaviors. A sample of 201 primarily Caucasian tenth through twelfth grade students from a suburban public high school district in the Midwestern United States were surveyed. Gender differences were found for some variables. Mother, father, and school attachment, explained significant variance in predicting several outcome variables. Finally, self-esteem was found to mediate several relations between attachment and the proposed outcome variables. Knowledge provided by this study may be used by educators and practitioners to improve assessment, treatment, and prevention of poor academic performance, internalizing symptoms, and risk-taking behavior among adolescents.