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Rural principal well-being affects retention and the well-being of the school community, but how does this effect differ for women and men? Additionally, rural communities are heterogenous with many unique opportunities and challenges depending on several factors, but quantitative literature often struggles by treating rural communities as homogenous. Thus, this study examines the effects of principal well-being on retention across differing and intersecting definitions of rurality, county-level and school-level. This unique perspective allows us to explore the effects of isolation on the relationship between well-being and intent to leave. My hope is that this study and the corresponding conversations will lead toward a renewed sense of well-being and support for rural female principals, particularly those in isolated communities.