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This comparative study examines how rural and non-rural leaders, in a mostly rural state, differ in their efforts to improve student learning and the contextually-based challenges they face in doing so. Findings from this qualitative study describe three significant differences between principals of rural and non-rural schools: their ability to attend to instructional leadership, their philosophies of leadership, and how they provide instructional supports. Apart from these differences, we found significant similarities, including isomorphism in instructional strategies, which may be due to an increase in efforts to meet the goals of ESSA’s accountability measures. While previous research suggests that rural schools are influenced more heavily by their community contexts, increasing accountability measures may shift influence away from communities and schools.