Attending school and working are consistently associated with positive outcomes for juvenile offenders returning to the community.; Using longitudinal data from the Pathways to Desistance Study, we used structural equation modeling to test whether better school experiences while incarcerated was positively connected to adjustment upon release among serious juvenile offenders (91% male) in the U.S. Adjustment was assessed as attending school for 310 legal minors (<18 years), and engaging in work for 259 emerging adults (≥18 years), as well as self-reported delinquency for all participants.; Accounting for incarceration and school history, results showed that facility school attachment, but not grades, was associated with decreased delinquency 12 months after release across sex in both age groups. Additionally, facility school attachment predicted engagement in school for returning minors. However, facility school experience was not related to engaging in work for returning emerging adults.; Results indicate that facility school climate matters for all juvenile offenders returning to their communities and that correctional education done right presents an important opportunity to reconnect returning minors with school, an important normative context of development. Conversely, results suggest that returning offenders who have 'aged out' of high school are a separate vulnerable group who may need additional support for successful reentry.