In facilitating prosocial identity formation and preventing recidivism among adjudicated youth upon reentry to school and community, one key issue to address is the confidentiality of juvenile records. Educators can support young offenders by teaching youth to problem-solve the disclosure of past juvenile involvements. This article discusses two lessons that aim to help adjudicated youth take responsibility for past mistakes, use discretion when discussing their history, and communicate future goals to potential employers.