To understand the challenges associated with the enactment of educational policies that aim to improve equity and opportunity for students of color with disabilities, this chapter focuses on two separately conducted ethnographic studies. The first investigates district administrators' approaches to addressing racial disproportionality after the 2004 reauthorization of the Individuals with Disabilities Education Act (IDEA), and the second focuses on the emic perspectives of students of color with disabilities given the California High School Exit Exam (CAHSEE) under the auspices of No Child Left Behind (NCLB). Using a critical policy studies perspective, the authors examine how policy enactment within varying local contexts is influenced by harsh material realities and a dense policy environment, which exacerbate existing inequalities for students of color with disabilities. Collectively, these factors provide ripe terrain for understanding how policies, at the macro and micro levels, struggle to produce equitable outcomes and instead contribute to the educational inequities experienced by students of color with disabilities. The chapter ends with recommendations for policymakers on how to address existing procedural practices and compliance measures that are inadequately addressing and contributing to the persistence of racialized outcomes for students of color with disabilities.