The Office of Indian Education (OIE) in the U.S. Department of Education funds competitive grants for Native American school leadership preparation programs in order to improve the education of disadvantaged students identified under the 2001 "No Child Left Behind" (NCLB) reauthorization of "Elementary and Secondary Education Act" (ESEA) of 1965 by increasing the number of Native American who lead Bureau of Indian Education (BIE) and higher Indian enrollment (HIE) schools across American. Funded programs emphasize culturally responsive curriculum and instruction that address the needs of BIE and HIE schools and the challenges that the leaders of these schools face. This study examines one program funded by the OIE in 2005 that was offered in an online format in order to make the program accessible for participants who lived in remote geographic locations where travel served as a barrier to higher education and licensure opportunities and allowed participants to continue to serve their schools and communities while completing their coursework. The emphasis on written communication in an online format, however, is very different than the oral tradition of learning that has anchored and preserved Native culture. This paper examines the role of oral tradition in Indian culture and education, the values and structure of the OIE-funded preparation program, accommodations and enhancements of the program to provide culturally responsive curriculum and instruction, and the successes and challenges of those accommodations and enhancements in supporting the oral tradition of program participants.