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Historically, there has been an overrepresentation of Black students in special education and at the same time an underrepresentation of Black special educators. It has become a struggle for school districts to find qualified special educators, especially Black special educators, to help meet the needs of a more racially diverse student population. Twelve Black special educators within an urban school district were interviewed to learn more about their feelings and experiences with a focus on recruitment and retention. Findings suggest that though participants enjoy teaching, learning, and building relationships within classrooms and communities, recruitment and retention strategies fail to encapsulate these values, attitudes, and beliefs that they deem important. Implications for the special educator workforce and future research are discussed.