The purpose of this study was to explore the perceptions and lived experiences of previously detained adolescents with disabilities in order to better understand the influence these experiences may have on their postsecondary outcomes. This study employed a phenomenological approach through a three interview series to further understand the lived transition experiences of detained youth with disabilities. The first research question is: how do previously detained adolescents with disabilities experience their disability during their detainment and re-entry transitions? The adolescents in this study failed to recognize their disabilities, which ultimately highlighted a need for increased self-determination and supports to understand their disability as an asset rather than a defect. This lack of ability to understand and identify needs and strengths influence how the adolescents engage with their communities and post-secondary life. The second and third research questions are: how do previously detained adolescents with disabilities perceive their detainment and re-entry experiences as influencing their engagement with the community, and post-secondary transitions? This study found that previously detained adolescents with disabilities perceive their sub-transition experiences as having a being influential to their engagement with community. Specifically, as it relates to their re-entry transition, the supports they receive as they return to the community play a significant role in how successfully they are able to rebuild relationships and reengage with school, employment and extra-curricular activities in their communities. Further, their descriptions of how they perceive their sub-transition experiences as influencing their post-secondary life illuminate the disconnection between their needs and their desires related to long term outcomes. The overarching question for this study is: what are the lived experiences of previously detained adolescents with disabilities? This study sought to provide a voice to individuals whose experiences were not represented in the current literature. While they all provided unique perspectives and experiences, the essence of their phenomenon lies with their common perception of transition as hindrances to their success. However varied their stories and united their struggle, they all shared goals for the future and exhibited success by remaining out of the juvenile justice system, some for multiple years post release. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]