Rural school districts, educating just over 25% of all public school students across the country, play an important role in the nation's educational landscape. At the heart of the success of rural school districts are the superintendents who run these rural and often small districts. Superintendents of rural schools throughout the United States, however, face challenges because of personal, professional and cultural obstacles that exist within the districts and communities in which they serve, causing an increasingly high turnover rate. The constant and significant affects of rural superintendent turnover poses a threat to student achievement and the economic sustainability of the rural communities that house them. The purpose of this qualitative multiple case study was to explore how the professional, personal, and cultural obstacles and supports impacting a superintendent's retention in rural school districts can be adjusted in order to shape policy and practices to retain rural superintendents through necessary personal, cultural, and professional supports. Purposeful sampling was used to select 5 rural superintendents in Pennsylvania to participate in the study. Individual interviews, one focus group interview and document analysis were used to gather information from the 5 rural superintendents. All responses were recorded and analyzed qualitatively for themes which focused around professional, personal, and cultural supports and obstacles. Research findings indicated the importance of: 1) professionally providing supports in the areas of collegialism, budget, and organizations that specialize in rural superintendent supports, 2) personally providing the ability to have time with family and spouse, exercise, and refraining from social media, and 3) culturally having an understanding and supporting school board and a community that realizes educational change needs to take place. This study should be useful for universities, school boards, state departments of education, and new superintendents to enable assistance for support of rural superintendents. It is recommended for future study that a larger demographic area, multiple states, be examined to view the commonality between the supports and obstacles facing rural superintendents across our nation as well as an expanded look at how social media is affecting the lives and work of the rural superintendent. [The dissertation citations contained here are published with the permission of ProQuest LLC. Further reproduction is prohibited without permission. Copies of dissertations may be obtained by Telephone (800) 1-800-521-0600. Web page: http://www.proquest.com/en-US/products/dissertations/individuals.shtml.]