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Teachers at all educational levels and disciplines are leaving the profession at a rapid rate across the United States with numbers increasing since the COVID-19 pandemic. Retention tools and strategies are critical to the success of a school and school district. The purpose of this single case study was to explore urban high school principals' perceptions of why teachers leave the teaching profession and to identify the methods used by principals to retain teachers. I conducted this single case study to answer two research questions rooted in Frederick Herzberg's Two Factor Theory. The research questions were first, according to urban high school principals, for what reasons do urban high school teachers leave the teaching profession? Second, what policies, procedures, or strategies do urban high school principals use to retain teachers? I collected data using semi-structured interviews with four principals, conducted a focus group discussion, and collected related artifacts. I analyzed the data using the data analysis spiral (Creswell & Poth, 2018). Analyzing the lived experiences of principals navigating teacher attrition allowed me to identify commonalities among their experiences, their perceived reasons for teachers leaving the profession, and the methods they used to retain teachers. As a result, I uncovered five findings. First, the principal participants in this study perceived compensation, performance pay, and workload balance as critical to teacher decisions related to remaining or leaving the profession in different ways. Second, the principal participants in this study identified leader support and relationships as reasons why teachers stay in the profession. Third, the principal participants in this study identified classroom management and negative student behaviors lead to teacher dissatisfaction. Fourth, the principal participants in this study recognized growth opportunities within the charter network as a reason teachers stay in the field. Fifth and finally, the principal participants in this study identified relationships as the leading retention strategy they used. This research benefits principals, district administrators, and teachers as it highlights principals' perceptions related to teacher dissatisfaction and their perception of the necessity of building meaningful relationships with teachers to reduce attrition. [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.]