This book analyzes the process of leaving school, commonly referred to as 'transition' for young adults with severe, complex, and multiple disabilities. It seeks to challenge prevailing assumptions and offer practical steps towards reversing customary accepted theories, methods, practices, and outcomes. Despite extensive research, policies, and procedures of transition, the reality is that post-school outcomes are worrying for those with significant special needs. Community inclusion depends as much upon in-school procedures and support systems as it does the inclusivity of society itself. This book directly addresses these concerns by examining the experiences of young adults living through their transitions in two countries, Aotearoa New Zealand and the USA. Engaging and highly readable case narratives bring fresh insights on the diversity of disability experiences, portraying the under-explored opportunities involved in a transition with dignity. Disability is an often overlooked aspect of one’s intersectional identity. Post-school transition is therefore positioned less as a procedural function of leaving school and more so an urgent matter of social justice. Readers will benefit from the transformative framing of post-school transition based on the capability approach. Genuine opportunities within the transition of young adults with significant disabilities and those who support them may promote a thriving life for all.