Traditional and cyber bullying have been identified as universal problematic issues facing adolescents, and research is needed to understand correlates associated with these phenomena. Structural equation modeling analyses examined associations between attachment to parents, traditional and cyber bullying or victimization, and mental health outcomes among 257 high school students (Average age 15.9 years). Key patterns emerged, including associations between maternal attachment and mental health outcomes; victimization and mental health concerns; and bullying and victimization in both traditional and cyber contexts. The role of attachment to mothers and fathers varied by context. Findings extend the literature by identifying risk factors in adolescence associated with bullying and victimization, as well as suggesting appropriate prevention and intervention strategies to increase adolescent well-being.