The purpose of this article is to compel educators to think critically about how the Individuals with Disabilities Education Act (IDEA), a prominent school-based legislation in the United States, and caregiver/parental participation relate to each other and to equity in special education outcomes. I use two illustrative case studies to show how educator's decisions about students, their use of disability policy, and their subsequent interactions with caregivers/parents result in vastly different outcomes for two young boys with a disability, one white and one Black. I outline how the racialized local context of the suburban, primarily white, and wealthy school district of study shaped understandings of difference that influenced how educators related to caregivers/parents, how they determined what was a viable caregiver/parental request for educational services, and how they subsequently leveraged educational resources to meet student needs based on these assumptions. In doing so, I engage with the following overarching question: "How do contextual influences affect educators' understandings of what is a viable caregiver/parental request when providing services to students with disabilities?" I end with a critical discussion about the presumed benevolence of special educators and special education systems.