The purpose of this mixed methods study was to explore factors that contribute to the retention of secondary school principals in rural settings in Missouri. The overarching research question this study sought to answer is: What factors increase longevity in secondary school principals in rural settings? The three conceptual underpinnings--rural education, the role of the principal, and principal retention--define important factors and converge to identify the gap existing in current literature. Using a survey, focus group, and interviews from rural school principals, this study found that the longevity of rural school principals is attributed to their skills in building relationships with students, parents, teachers, and community members, as well as multitasking. The study also confirmed the challenges faced by rural school principals discussed in previous literature. Considering this finding, principal preparation programs and professional organizations could better prepare principal candidates for rural schools. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]