This qualitative research study consisted of nine face-to-face interviews with unaccompanied youth (UY) living in homelessness and receiving services from a New York City (NYC) based Drop-In Center. Drop-In Centers are funded by the NYC Department of Youth and Community Development and designed to provide a continuum of services for youth who are undomiciled or at risk for homelessness aged 14 to 24. These centers can serve as an emergency entryway into the formal NYC adult homeless shelter system for youth over the age of 18. Each interview focused on uncovering the UY's pathway to homelessness as well as their previous and current experiences with the educational and mental health systems. Braun and Clarke's (2006) framework for thematic analysis was employed to analyze the data from all individual interviews. In total, 13 themes were identified and categorized into five broader groups: (1) early life experiences marred by trauma and maladaptive coping, (2) perceived lack of support from family and helping systems, (3) impactful educational experiences that have shaped UY attitudes and perceptions about school, (4) perceptions and attitudes about mental health and treatment, and (5) developing and maintaining a counternarrative of success and agency. The implications of participants' experiences are outlined and elucidate how educational and mental health systems and personnel, in particular school psychologists, can best approach conceptualizing and engaging such a complex and underserved subset of the homeless population. [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.]