Young offenders present many challenges to the juvenile justice system, the school system and the labor system as they transfer from residential commitment to their home communities. The challenges can be overwhelming, potentially creating a sense of hopelessness for the community and for the youth. In response to the need for appropriate academic programs for youthful offenders, juvenile justice programs increasingly pursue creative alternative partnerships with education and labor. This article explores the issues that arise for youth and communities during the critical transition period following incarceration and offers evidence of effective strategies helpful in overcoming the educational barriers common to the transition process.