In a 1991 report, the Indian Nations at Risk Task Force documented a lack of Native educators as role models for Native American students and set a goal of doubling their number by the year 2000. Under-representation of Native American educators remains an issue today particularly with regard to school leaders (Planty et al. 2009; Snyder and Dillow 2010). In order to increase the number of Native American educational leaders serving Bureau of Indian Education (BIE) schools, and other schools with high concentrations of Native American students, the Educational Leadership and Policy Studies program and School of Special Education at the University of Northern Colorado developed a two-year online multidisciplinary Master's of Arts degree program for Native American teachers to obtain both principal and special education administrative licenses. This article describes the context, design, and evaluation of this new degree program. In addition, drawing upon the experiences of program staff, faculty members, and participants (students), it presents the challenges and lessons learned in the areas of recruitment and retention; program structure and online delivery; and cultural accommodation and enhancement. (Contains 9 endnotes.)