For the approximately 36,000 youth who are adjudicated, detained, or incarcerated within the juvenile legal system at any point during the most recent year of reporting, a wealth of research has identified a host of factors that serve as barriers to the attainment of employment, higher education opportunities, or technical and trade skills acquisition upon their release. Prominent among these barriers is the difficulty youth have in acquiring skills-based education or training to prepare them for the workforce and for the rigors of managing adulthood successfully. Transition, the process that occurs when a formerly system-involved youth moves from placement in the juvenile legal system to a community-based placement and/or release, has been explored across intersecting bodies of literature with varying approaches identified to best support youth during this process of transition. This chapter explores what may be needed to additionally support youth with juvenile legal system involvement during transition. Building on ideas highlighted within a case study, supporting youth through internships, career planning, and mentoring during the transition period are discussed.