The education and rehabilitation of incarcerated youth, and support for their effective transition, is a complex endeavor. Many youth involved in the juvenile justice system possess risk factors that are linked to antisocial behavior and recidivism, including a history of poverty and maltreatment, psychological disorders, and eligibility for an emotional disturbance (ED) or learning disabilities (LD) special education classifications. As such, the discussion and potential approaches to supporting these youth are necessarily complex and must be multi-faceted. This research brief provides an update of available evidence related to education and rehabilitation of incarcerated youth and those transitioning to school, community, and the workforce, since the original publication of the Guideposts for Success for Youth Involved in the Juvenile Corrections System (JJ Guideposts) within the Right Turn Guide in 2008. It also provided recommendations for improving transition outcomes among incarcerated youth.