Despite completing Career and Technical Education (CTE) programs, Students with Disabilities (SWD) are less likely than their nondisabled peers to secure middle-skill employment related to their training. This discrepancy is due to insufficient support and interagency collaboration to help overcome transitional barriers and build relevant work connections. Missouri Vocational Rehabilitation's Progressive Employment Program aims to bridge this gap by offering wrap-around support to maximize students' employment potential. This qualitative study examines the effectiveness of the Progressive Employment Program in helping SWD transition from CTE to middle-skill jobs. This exploratory case study, guided by Social Cognitive Career Theory and Social Capital Theory assesses how the program helps SWD overcome transitional barriers, build employer connections, and gain industry experience. Data collection involved two focus groups with thirteen Progressive Employment team members, interviews with five former SWD and five employers, and two observations of team meetings. Results indicate that the program significantly aids SWD in obtaining jobs pertinent to their CTE training by providing support, integrating funding sources, leveraging social capital, offering relevant work experiences, and enhancing students' self-efficacy. The program was critical in preparing SWD in CTE for their career pathways, leading to employment and aligning their skills with industry needs. [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.]