The school district is the fundamental administrative unit of schooling in the United States and the superintendent the lead official. The nature and the challenges of this position, however, vary across the landscape. Because most superintendents lead rural districts, the challenges facing those districts are the ones that typically bedevil the superintendency overall (perhaps a surprising thought to many readers). From this vantage, we theorize such challenges overall, and illustrate the theory with three episodes: (1) the continuing threats of school and district consolidation; (2) the arrival of ethnic diversity in previously all-White rural places; and (3) the leasing of school lands for mining, with a focus on hydraulic fracturing ("fracking").