Through a qualitative phenomenological design, this study explored the perceptions of teachers at private academic emotional support schools regarding the influencing factors of teacher retention for multiple years. Studies have spanned for decades attempting to understand and prevent teacher attrition in these schools. Working conditions of the school environments and school leadership have often been reported as leading factors. There have been no found studies reflecting the insights of teacher retention, especially at hard to staff schools serving challenging student populations. This study discovered the experiences of teachers at a private academic emotional support school who accepted their teaching position and the reasons they choose to return each year. The theoretical framework proved to be an effective method of guiding in depth reflective conversations about teachers' positive experiences in their school settings with school leadership and with their students. The teachers in this study choose to return to their positions for multiple years because their work environments are positive and they regularly feel successful and satisfied with their workdays. The teachers agreed that low self-efficacy and the inability to cope with levels of stress is a leading cause of teacher attrition. The results of this study provide facilitated transparent conversations about desired improvements and strategies that would ensure their retention. [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.]