Reentry, also referred to as transition, is a critical component in preparing at-risk youth in juvenile justice facilities for successful postrelease outcomes. However, successfully preparing these youth for reentry into the community and back to traditional K-12 schools is still difficult for many justice facilities. With the continued calls for action in providing comprehensive reentry programming in juvenile justice, this special issue on reentry considerations for at-risk youth from juvenile justice facilities is timely. The articles within this special issue share current and emerging practices to meet the complex transition and reentry needs of justice-involved youth. The articles also aimed to provide opportunities for both youth and juvenile justice teachers and staff to voice their views and experiences related to reentry programming and practices. Implications and future directions for researchers, juvenile justice staff, and other professionals are included within each article.