Little is known about the maternal relationships, attachment classifications, and developmental trajectories of juveniles presenting with sexually abusive behavior, sexual victimization, and emerging personality disorders. Using the Adult Attachment Interview (AM), this case study explored attachment relationships and state of mind regarding early attachment classifications in a forensic sample of juveniles with sexual behavior problems (N=3) and their mothers (N=4). The adolescents, who were either receiving inpatient or outpatient treatment for sexual misconduct, were clinically interviewed and administered the Minnesota Multiphasic Personality Inventory-Adolescent (MMPI-A) and the Adolescent-Dissociative Experiences Scale (A-DES) to assess personality characteristics, mental health disturbances, and their perceptions of childhood experiences, including trauma. Findings suggested the possibility of a link between the classification of Unresolved-disorganized for trauma and loss for mothers and the Unresolved-disorganized classification found in their sons. It is argued that there is a possible link between attachment disorganization, sexual victimization, and sexual offending. Attachment disorganization could account for some of the known characteristics of adolescent sexual offenders such as aggression and socioaffective problems. It is suggested that, if attachment disorganization is found in mothers of young offenders and also in their sons, this would have important implications for treatment.