This article shares findings from an exploratory case study about an advanced leadership development program for administrator-certified practitioners in a Central Appalachian school district. The goal of the Principals Excellence Program, one of 24 projects supported by federal funds through the No Child Left Behind School Leadership Development Program, is to transform the principalship by developing visionary instructional leaders able to increase student learning in high-need rural schools. In this article, the authors first talk about the contextual conditions that define the district as high need and provide an overview of the program and research design. The authors then present findings about: (a) preparing school leaders to promote learning success for all students; (b) addressing equity and social justice issues; and (c) providing adequate learning opportunities. Perspectives from representatives of all stakeholder groups are integrated to provide a holistic assessment of the program. The article closes with a discussion about lessons learned thus far about effective leadership preparation. (Contains 34 endnotes.)