Identifying factors that contribute to delinquency and recidivism is critical in predicting the success of incarcerated youth transitioning back to the community. The task of identifying these salient factors becomes increasingly complex when compounded by the disproportionate representation of youth with disabilities in juvenile corrections. These youth are also far less likely to make a successful transition to the community. Research in this area has examined the impact of individual, environmental, and situational factors on the likelihood for success, but a synthesis of this research has yet to be compiled. The purpose of this article is to examine the contextual factors that influence the transition success or failure of youth with disabilities in the juvenile justice system. Specifically, 10 research studies conducted by graduate students and faculty in the special education program at Arizona State University are reviewed. This research has been conducted over the past 12 years and has focused on identifying factors associated with successful and unsuccessful transition of youth from incarceration to school, work, and the community. Implications for designing and implementing appropriate programming and transition planning to address the needs of youth exiting the correctional system are also highlighted. The specific research topics related to transition include preplacement planning, locus of control, engagement, peer influence, quality of transition programming, gender specific programming, and adult mentoring and support.Identifying factors that contribute to delinquency and recidivism is critical in predicting the success of incarcerated youth who transition back to the community. Resilience and recidivism are not fixed factors; they are fluid and interconnected with a host of both alterable and unalterable variables. The task of identifying salient factors for youth exiting the justice system becomes increasingly complex when compounded by the disproportionate representation of youth with disabilities in juvenile corrections. These youth are also less likely to make a successful transition to the community.