Innovations associated with gas and oil drilling technology, including new hydraulic fracturing and horizontal drilling techniques, have recently led to dramatic boomtown development in many rural areas that have endured extended periods of economic decline. The Marcellus Shale play, one of the world's largest gas-bearing shale formations, lies beneath approximately two-thirds of Pennsylvania, including some of the state's most economically lagging rural areas. Spurred by a state-level policy environment favorable to unconventional gas extraction, drilling activity in the last five years has rapidly increased, often with profound social, economic, and environmental implications for communities. In this paper we use schooling as a particular analytic lens for understanding the dynamics of natural resource boomtown development, community change, and how these changes may affect educational and instructional decision making. Using data from interviews and focus groups with educators and administrators in Pennsylvania communities experiencing intensive natural gas development, we discuss the multiple organizational, curricular, and educational dilemmas school leaders face in the context of both rapid, unpredictable community change, and an educational policy environment unfavorable to place-sensitive educational responses to local change.