Equity issues continue to surround the supports and services provided to students with dis/abilities from birth onward, especially for children of color and despite extensive legal protections guaranteed through the Individuals with Disabilities Education Act (IDEA). The purpose of this article is to examine how these systemic issues unfold in practice during early childhood transitions as young children of color with dis/abilities move from preschool to an elementary school setting. Using ethnographic data gathered from a large suburban school district in the northeastern United States, we explore the equity implications associated with the transition from preschool to kindergarten in a sociodemographically diverse school district. We used a context-centered approach to examine how educators use IDEA to serve families during the transition process and how educators and families interact with each other during transition planning meetings. Cultural misunderstandings and power differentials between caregivers and educators emerged from the data analysis and provided insight into how and why IDEA procedural protections were insufficient for assuring the rights of students with dis/abilities were protected during the transition process. We argue that the extensive procedural protections for children served under IDEA are inadequate in assuring equity in special education outcomes during the transition process. We conclude that the transition process does not disrupt oppressive practices, effectively thwarting equity and access in early childhood education. We end with recommendations for improving the process.