It is widely recognized that effective school leaders can significantly influence student learning outcomes. Many of the same practices that enhance student learning are associated with school-level factors that can enhance teacher retention. The increased awareness of school leaders’ potential to positively influence school-level conditions that influence both student learning and teacher retention has led to an increased focus on the development of practising school leaders. The need for effective school leadership development is greater in rural and high-poverty school settings, which typically have greater challenges staffing schools. Yet, access to the high-quality professional learning opportunities, which could assist leaders of such school leaders in making the changes necessary to increase teacher retention, is limited. In this chapter, we describe how a research–practice partnership between a university and a consortium of 14 predominantly rural and high-poverty school districts filled a gap in school leadership development over a 13-year period through coaching, professional community, and a focus on continuous improvement. We conclude this chapter with insights gleaned from our experiences as university partners in a research–practice partnership that is filling a gap in rural school leadership development.