Three of four high school students with special needs become unemployed after graduation. These students, referred to as "bridge students" as they transition into postsecondary life, seldomly escape lifestyles of criminal, sedentary or dependent behavior. Certain protocols enacted at the high school level may act as either barriers or facilitators to the academic and transitional growth of bridge students. A qualitative cross-case analysis of two high schools was conducted in an effort to explore those practices of teachers, counselors and administrators that may either help or hinder a bridge student's ability to cope with the transition into college and/or a career. An examination of the institutional protocols that are performed to service these students was performed. Emphasis was placed on identifying specific transitional, inclusive, and social-emotional supports that were evident in the data. Higher functioning students with special needs were selected as participants for this study. A combination of interview, observational and document analysis data was collected from both schools. Two administrators, four teachers and four counselors were interviewed between both sites. The following themes emerged upon analysis of all data: (a) culturally relevant skill building among bridge students is crucial to their academic and transitional success, and (b) teacher training and buy-in are necessary to effectively nurture the self-advocacy skills that are required for bridge students to transition successfully into postsecondary life. The theoretical framework, Schlossberg's Transition Theory, guided the discovery and exploration of those institutional protocols that act as either facilitators or barriers to the overall advancement of bridge students. [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.]