Although numerous studies confirm the importance of school principals, schools often experience high turnover rates and principal shortage. However, we know little about the staffing challenges in rural schools and what promotes applicants to apply for and be hired for principalship. 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 in Wisconsin. We find that all rural communities--"rural fringe," "rural distant," and "rural remote"--receive equal or high number of applications compared to urban districts. Female candidates are significantly less likely to apply to rural districts, while working in the same district is a considerable advantage to being hired. Among district characteristics, the percentage of students eligible for free or reduced-price lunch tends to reduce the number of applicants in rural schools. Our results highlight the need for policies that are better attuned to the subtle differences in rural contexts.