The post high school transition for males with a specific learning disability (SLD) can be challenging. Unemployment among persons with disabilities was markedly higher than those without. There was also mounting evidence that showed that persons with disabilities had difficulties adjusting to post-secondary environments. For male students with disabilities, their post-secondary experience was impacted by the support services received, both at school and within their community. Little was known about the post-secondary experiences of minority males with SLD. The purpose of this qualitative study was to explore post-secondary transition experiences among Virgin Islands male high school graduates with SLD. Particularly, this study sought to describe the barriers and support to their successful post-secondary transition. The social cognitive career theory was the theoretical framework used in this study. Six Virgin Islands males with SLD, who completed high school between 2010 and 2019, participated in semi-structured interviews. Interpretative phenomenological analytical strategies were used to analyze data from interviews. The results showed an overwhelmingly favorable response to the support received from parents, teachers, and counselors. Results also showed that males with SLD strived to achieve post-secondary education and gainful employment and independence, but they lacked self-advocacy skills that can help them successfully navigate through this transitionary period. Results of this study has the potential for positive social change by helping education administrators, the Virgin Islands vocational rehabilitation and other disability services in improving transition services for persons with disabilities by raising awareness among parents advocating and requesting optimal transitional services for their children. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]