<p>Young adulthood is a period of changes, including transitioning from pediatric to adult healthcare; this is often an informal, disjointed process of securing new insurance and finding adult providers. Children and youth with special healthcare needs (CYSHCN) have more contact with the healthcare system than their peers, thus presenting more opportunities for gaps in care and consequently negative health outcomes during healthcare transition. The discontinuities between pediatric and adult healthcare are particularly consequential for the subset of individuals with intellectual and/or developmental disabilities (I/DD), especially those who will not develop autonomy and the capacity to function on their own. While parents and other caregivers often try to bridge the gaps, transition can be confusing or even dangerous because of ableist assumptions about what it means to be “an adult” patient. When independence is built into policies, procedures, and expectations that paradoxically limit access to and participation in healthcare spaces or services, that is structural ableism. This perspective provides examples of structural ableism in healthcare transition and offers suggestions for how a re-orientation toward radical inclusion for those who need it most can enable better care for all.</p>