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This study examines the development of rural principal pipelines across three Virginia school divisions participating in a Wallace Foundation-supported project. Drawing on feedback from rural education leaders and grounded in theories of spatial and educational equity, we examine how local challenges and strengths impact leadership development. Results highlight the importance of localized pathways, cross-role collaboration, and sustainability planning. Rurality is not a barrier but a productive context that requires specific policy attention. Simply adapting urban-focused pipeline models for rural areas is not adequate. Therefore, this research offers vital insights into principal preparation, recruitment, and retention in underserved communities, allowing rural leaders to “sit up a little taller” in their ecosystems.