Youth served within juvenile justice facilities are to be afforded the same educational benefits as their peers in nonsecure educational settings, including transition supports. Transition supports include the purposeful delivery of strategies and interventions to build a wide variety of skills based on youth interests and preferences regarding navigating movement from the juvenile justice environment to their neighborhood school, postsecondary education, workforce, or community at large as well as overall success in the new environment. In the current qualitative study, 11 staff (e.g., teachers, administrators, parole officers) who work with justice-involved youth across five states participated in semistructured, open-ended interviews on the transition programming and needs of youth from their facility back to traditional K--12 schools and the community at large. Using the constant comparative method, the interviews were coded to gain a deeper understanding of the transition programming and practices in juvenile justice facilities along with identifying areas for future youth support and research. Five major themes were identified across interviews related to the barriers and successes in transition programming, establishing collaborative partnerships in the community, and gaining access to additional transition resources. We touch on each theme with direct quotes from the interviews and discuss future directions to best support transitioning youth from juvenile justice settings.