Purpose: Much of what is known regarding the transition away from crime is limited to young adulthood and specific life events and samples of non-serious offenders comprised mainly of white males. Methods: The current study assesses the potential links between educational achievement, post-release schooling, and re-arrest for a cohort of 4,147 incarcerated youths drawn from 115 Florida juvenile institutions and followed for two years post-release. Results: Incarcerated youths with higher levels of educational achievement are more likely to return to school after release, and those youths who returned to and attended school regularly were less likely to be rearrested within 12 and 24 months. Moreover, among youths who were rearrested, those youth who attended school regularly following release were arrested for significantly less serious offenses compared to youths who did not attend school or attended less regularly. Conclusions: The study concludes with discussion of the importance of educational achievement as an important turning point for juvenile offenders as they transition into young adulthood.