This research is a qualitative case study exploring the factors that influence the attrition of mentors in rural areas. Mentoring initiatives and programs have proliferated throughout schools in an effort to provide students with positive role models, increase graduation rates and improve overall performance Mentoring programs are an increasingly popular strategy for enriching children's lives, helping to meet their need for positive adult contact and for providing one-on-one support and advocacy. Mentoring relationships are most likely to promote positive outcomes and avoid harm when they are close, consistent and enduring. Most notably, positive mentoring experiences have proven to be an effective tool to help youth overcome the risk factors that can lead to problems such as educational failure, dropping out of school and involvement in delinquent activities, including gang involvement, criminal mischief and drug abuse. Insights gained from the present study will enable educators and program managers to refine their existing mentoring programs to augment sustained relationships between proteges and mentors and avoid the harm that ending the mentoring relationships prematurely may cause the proteges. The key subjects in this study were current and former mentors from schools documented in the film, "Corridor of Shame". Also included are directors of mentoring programs from these schools and a volunteer recruiter who focuses primarily on rural schools. The present study examined the attrition factors of mentors in high poverty rural areas, such as those in the documentary, as well as mentors in high poverty schools, many with similar demographics as those described in Jonathan Kozol's "Savage Inequalities" (1991). The pattern of findings implied that short-lived matches can have a detrimental effect on youth and that the impact of mentoring grows as the relationship matures. For former mentors, it was found that lack of infrastructure, health issues and location of mentoring sites were some of the key factors that contributed to the termination of the mentoring relationships. For current mentors, the factors that contributed to the sustainability of their relationships were their spirituality and the various needs of the students. Possible unrealistic expectations for mentoring relationships were also examined. [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.]