This report highlights key lessons learned from the experiences of three Office of Juvenile Justice and Delinquency Prevention (OJJDP) funded demonstration grants to incorporate green technologies and environmentally sustainable activities in programs designed to help detained and reentering tribal youth successfully reintegrate into their communities and to prevent future criminal behavior among at-risk youth. This report highlights key considerations relevant to incorporating “green” activities in juvenile justice settings. The findings are of interest to those who work with justice-involved youth and are interested in incorporating gardening, greenhouses, and related activities. The findings are based on the Cross-Site Evaluation of OJJDP’s Green Reentry Program (NCJ 248537) and are of particular relevance to practitioners who work with tribal youth. Because green activities offer a natural opportunity for tribal youth to reconnect with their traditional culture, many of the lessons in this report are relevant to a holistic approach in which green activities are complemented with cultural components.