Research has linked the role of education to delinquency, but much of the focus has been on general population samples and with little attention to demographic differences. Employing a cumulative disadvantage framework that integrates elements of informal social control and labeling theories, this article examines whether academic achievement serves as a positive turning point and re-directs juvenile delinquents away from subsequent offending. Attention is also given to race/sex contingencies. Using a sample of 4,147 delinquents released from Florida correctional institutions (86% male, 57% non-White, average age at release = 16. 8 years), propensity score analysis yielded two findings: youth with above average academic achievement while incarcerated were significantly more likely to return to school post-release, and youth with above average attendance in public school were significantly less likely to be re-arrested in the 1-year post-release period. While the academic gains were pronounced among African-American males, the preventive effects of school attendance are similar across race and sex, suggesting that education can be a part of a larger prevention effort that assists juvenile delinquents in successful community re-entry.