Juvenile detention and correctional facilities, in collaboration with state agencies and local school districts, have adopted a number of practice and policies to promote educational re-enrollment and advancement following release. Informed by limited research and the accounts of practitioners and clients in the field, this article discusses practices with some evidence of promise or success. First, a high school diploma is more valuable than a General Education Development (GED) certificate and could be more attainable if correctional facilities and receiving school districts coordinate more effectively. Two means for incentivizing school districts' cooperation are to require that they fund the correctional education of students from their districts and to institutionalize the practice of local school district awarding diplomas even when high school course work is completed while incarcerated. That said, remedial education or GED preparation are practical and viable for most incarcerated youth, and effective strategies exist for enhancing portability and curricular continuity. Second, building upon successful transitional support programs for incarcerated youth with special needs, practitioners and policy makers in several states have devised strategies to facilitate timely re-enrollment in an appropriate school setting. For example, Virginia laws mandates that Transition Teams inside facilities and re-enrollment teams in the receiving school district work to secure an appropriate educational placement prior to release and that the receiving educational program is promptly sent all the documentation necessary (e.g., transcripts, immunization records) to enroll the youth. Some key coordination and advocacy services can be effectively performed by volunteer mentors. More research is needed to determine which transition support services and programs boost the likelihood and the duration of educational re-enrollment.