Despite growing awareness of the teacher staffing crisis in rurally isolated, impoverished Montana school districts, little has been done to effectively address the issue. As opposed to a general lack of supply, current state and national research attribute the problem to challenges in teacher recruitment and retention. While many of these studies have identified factors associated with teacher staffing challenges, none have fully conveyed the essence of the struggle through the experiences of school leaders who endure the crisis. Therefore as revealed through the experience of eligible superintendents, the purpose of this qualitative study was to investigate teacher staffing challenges in rurally isolated, impoverished Montana school districts and the role of state school funding policy in the recruitment and retention of high quality teachers. Anchored by punctuated equilibrium social theory, the study's conceptual model provides a basis for multiple instrumental case studies. Investigative research began with two focus groups of eligible superintendents and was followed by multiple interviews with the superintendents of four representative case study school districts. Audio recordings of interviews were transcribed and reviewed using typological data analysis methods to identify semantic relationships, themes, and significant statements. Study trustworthiness was established through bracketing the researcher's personal experiences with teacher staffing challenges, thick description, peer review, member checking, and triangulation with school district related information and other state research. Findings indicate that current Montana school funding policy may exacerbate the staffing challenges experienced in these remote and poor districts as well as their organizational functioning.