Increasing engagement to school, employment, and community are strong predictors of reducing recidivism for youth involved in the juvenile justice system. This study examined what occurs at reentry upon leaving a youth correctional setting. This study comprised of qualitative semi-structured interviews of transition specialists (TSs; n = 7) and young offenders (n = 8) who participated in a 4-year reentry project in the Pacific Northwest. A total of 21 (13 TS and eight youth) interviews were thematically coded. Findings from this study included the important role of the TS in supporting a youth's school, family, and community reentry. Key themes are described around the services to support employment, school engagement, and independent living during a youth's reentry into a school setting.