Though education is a jurisdiction of the states, services for identified students are federally mandated and protected under the Individuals with Disabilities Education Act, or IDEA. This study consisted of 14 semi-structured interviews with special education administrators in Illinois. Questions focused on how federal and state mandates impact administrator’s decision making regarding the services they can provide for students and how unique special education agreements are structured among districts. Findings of this study include why unique special education service agreements arise across Illinois, the impact of a private tuition reimbursement that unduly influences decisions regarding high needs students, and insights into stigmatization of special education services. Additionally, this study reveals that arbitrary changes to funding flow have time consuming consequences, and the teacher shortage within Illinois is impacting the quality of services districts provide to students. This research provides the framework to substantively inform policy recommendations: streamlining and equalizing funding models, conducting more research on the impact of funding mandates, ensuring that communities are educated about students in special education programming, and increasing IDEA grant funding.