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Under a resilience theory framework, this single-site case study investigated the facilitating factors and barriers that influence the ability of students experiencing homelessness to graduate high school. I conducted semi-structured interviews with high school graduates and school district personnel from a selected Virginia school district, through two researcher-developed instruments. Participants understood the value of the diploma as a measurement of personal success and predictor of future opportunities. Additionally, educator-student relationships, specifically among students and teachers, counselors, and McKinney-Vento staff, were vital to ensuring students’ basic, emotional, and academic needs were met. The results of this study are significant, in terms of providing insights on next steps to closing the high school graduation gap between stably and unstably housed students.