The aims of this study were to investigate the rates of deliberate self-harm (DSH) behavior among an Italian adolescent sample, as well as to explore its clinical correlates. On a sample of 234 adolescents in Italian secondary schools (Mean age = 16.47; SD = 1.7) were assessed the DSH as well as externalizing symptoms (including both conduct disorder [CD] and oppositional defiant disorder [ODD] symptoms), borderline personality disorder [BPD] symptoms, dissociative symptoms, and the incidence of life-stressors. Consistent with past research on DSH in youth, 42% of the adolescents in this sample engaged in DSH. Results indicate a positive association between DSH and all psychopathological correlates, including BPD, dissociative, and ODD and CD symptoms. Further, findings revealed an association between DSH and specific life-stressors (i.e., psychological and sexual abuse, natural disasters and serious accidents, the loss of someone important, and the witnessing of family violence or a serious accident). (Contains 3 tables.)