The problem addressed in this study is that students with disabilities are improperly prepared for postsecondary college and career outcomes. The purpose of this qualitative single-case study was to gain insight into the experiences of current and past teachers and transition service providers of students with disabilities, specifically regarding how transition services should be prioritized to optimize student postsecondary success. This study employed a qualitative methodological approach, using interviews and questionnaires from special education teachers and community transition service providers. Two research questions were used to address the problem and the purpose. The study utilized data from providers across South Carolina and included a sample size of 20 participants. Vygotsky's theory of social constructivism and Kohler et al.'s Taxonomy for Transition Programming 2.0 were utilized as theoretical frameworks to guide the investigation. Thematic analysis was used to synthesize themes from the qualitative data collected. This synthesis resulted in three themes related to research question one and three themes related to research question two. Implications and recommendations for practice included: a) intentional postsecondary planning that includes inter- and intra-agency collaboration, b) intentional collaboration with potential employers, c) institute required training for all exceptional services instructors, d) provide opportunities for alternative assessment related to work readiness training, and e) consider making the South Carolina High School Diploma and Credential equivalent. Recommendations for future research included: a) repeating the case study methodology but increasing the sample pool, b) including a quantitative data point to demonstrate how student progress may increase over time with structured work readiness training (WRT) instruction, and c) comparing the post-school outcomes of students who receive WRT to those that receive a "business as normal" model. [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.]