This study examined the experiences of students with disabilities transitioning from high school to the post-secondary institution. Participants were seven successful students enrolled in their second year at a Southern California community college and two resource specialists who worked closely with them. A case study was determined to be the most meaningful way for this research to collect qualitative data that was both meaningful and was able to capture the true essence of participant's experiences. This study was guided by three overarching research questions. The first was, "How do students successfully navigate the differences in services between the collegiate setting and the high school setting?" The second question was, "How do we better prepare students to use essential skills needed in post-secondary settings?" The third and final question was, "How does disability identity tie into the development of students as they progress from high school to the post-secondary setting?" Through the collection and analysis of the data, several themes emerged that showed what is needed most to improve transition planning and transition services for students entering the post-secondary setting. The need for self-advocacy training at both the high school and post-secondary level, the need for a more meaningful alignment between the two areas of service, and the lack of Individualized Education Plan involvement and effective transition planning processes were all emergent themes in the study. Participants conveyed that they were ill-prepared for community colleges with the areas of advocating for services and needs, being successful self-advocates, understanding the process of accessing services, and college familiarity identified as particular areas of struggle. [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.]