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This paper explores the critical daily functions of rural school principals leading sustainably improving schools. Previous research has investigated the many hats rural administrators wear, and this study extends this scholarship by exploring the work of rural principals through Portin’s (2005) critical functions of school leadership framework. This study’s findings explore the ways in which the rural context of these schools impacts critical functions, such as instructional, cultural, and managerial leadership, and the ways in which these functions inform one another. Finally, the nature of tightly coupled rural schools and communities is explored as well as the impact this dynamic has on the work of rural principals. The paper concludes with implications for leadership preparation and practice.