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This qualitative study explores the post-school experiences of young women with disabilities through a series of in-depth interviews conducted over 18 months. While prior research provides broad trends regarding post-school outcomes, this study centers the voices of young women as they navigate the realities of work, education, relationships, and identity after high school. Findings reveal not only the systemic and personal barriers they encounter, but also the resilience, adaptability, and insight they bring to these transitions. By examining how their goals shift over time and how they draw on limited supports, this study offers critical implications for strengthening transition planning, fostering self-advocacy, and reimagining more responsive, equity-driven approaches to preparing young women with disabilities for adulthood.