The purpose of Education for Homeless Children and Youth (EHCY) program in the McKinney-Vento Homeless Assistance Act (2015) is to protect the educational rights of students experiencing homelessness across the United States. Despite the coordinated efforts of State and Local Educational Agencies to carry out these mandates and ensure equitable academic opportunities, students in unstable living conditions are graduating high school at lower rates than their housed peers both in Virginia and throughout the nation. This study investigated the facilitating factors and barriers that influence the ability of students experiencing homelessness to graduate high school. The research questions addressed facilitating factors and barriers, as well as the perceived impact of a high school diploma and recommendations for various educators and other stakeholders, using Resiliency Theory as a background theoretical framework. In this single-site case study, I interviewed six high school graduates and eight school district personnel within a selected school district in Virginia, through two researcher-developed instruments, the High School Graduate Semi-Structured Interview and the School District Personnel Semi-Structured Interview. Results revealed that all participants understood the value of the diploma as a measurement of personal success and a predictor of future options and opportunities. Additionally, relationships fostered through good communication and small community settings played a critical role in helping students feel supported and connecting them to the services they needed to be successful. Teachers and counselors, as well as McKinney-Vento staff, were vital to ensuring students' basic, emotional, and academic needs are met. The results of this study are significant, in terms of providing scholars and practitioners insights on next steps to closing the high school graduation gap between stably and unstably housed students. [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.]