Across the United States young women with disabilities are experiencing economic and educational disadvantages. Although post-school outcomes have shown improvement, young women continue to experience high unemployment rates, low wages, and high rates of poverty. In this study, I explore the experiences of four teenage girls who have been labeled as having learning disabilities and intellectual disabilities. Through in-depth interviews, supported collage making, document review, and the AIR Self-Determination Scale, I examine how they experience girlhood, schooling, and transitions. I consider the ways in which adolescent girls with disabilities negotiate special education, social relationships, and the salient and permeable borders of girlhood and adulthood. I consider how the policies and practices of special education both produce and police gendered narratives of behavior and compliance. I also examine the liminal space of post-school transitions. I contemplate issues of equity and access to opportunity, while examining the consequences of labeling, segregation, and interlocking systems of oppression such as race, class, and gender on these opportunities. Further, I consider the participants' diverse understandings of and experiences with self-determination. In the conclusion, I present a framework for a more equitable and culturally responsive approach to transitions and describe the implications of this study for teachers, parents, students, and teacher preparation programs. [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://www.proquest.com/en-US/products/dissertations/individuals.shtml.]