Numerous studies have explored the labor market of school principals, documenting high turnover rates and voicing concerns regarding labor supply. However, little is known about the staffing challenges in rural schools and what promotes applicants to apply for and be hired for principalship in these locales. In partnership with the Wisconsin Education Career Access Network, we examine the principal labor dynamics in rural schools using statewide job-openings and application information. Results indicate that all rural communities--rural fringe, rural distant, and rural remote--receive comparable numbers of applications, as compared with urban districts. Female candidates and candidates of color are significantly less likely to apply to rural districts, while experience working in the same district is a considerable advantage to being hired. Additionally, higher student poverty is associated with fewer principal applicants in rural schools. These results indicate the need for policies better attuned to subtle differences in rural contexts.