Long-standing shortages of well-prepared special educators, especially within rural areas, have jeopardized positive outcomes for students with disabilities. In this multiple case study of administrators and special educators, the authors examined how individuals make sense of the special education teacher shortages in relation to the challenges of working in a rural school. Local contextual factors intersected with salary and state policies, highlighting how external, political factors affected districts' ability to attract and retain special education teachers. Chief among implications for research, policy, and practice is the need to attend to multipronged approaches that have the potential to mitigate economic barriers to special educator recruitment and retention in rural school districts.