The purpose of this study was to explore the strategies districts use to retain principals in their complex roles through the framework of culturally responsive district leadership. This qualitative case study explored how district leaders in one Massachusetts school district focused on principal retention and whether their actions influenced a principal's decision to remain in their role. The study took place during a global health pandemic placing principals at the center of navigating this crisis. This study is part of a larger study that investigated how principals benefit from and shape professional capital to improve schools. Data were gathered from semi-structured interviews with district level leaders and principals. Findings demonstrated that there are things districts can do that positively influence principal retention, although these practices are not necessarily culturally responsive. Data supported the literature that professional development and mentoring, improved working conditions, and autonomy all positively influence principal retention. In addition, this study concluded that focusing on positive relationships and "growing your own" leadership are also key strategies to promote principal retention. Inorder to enact culturally responsive retention, recommendations include exploring whiteness in leadership and the influence of race on principal retention. Additionally. further investigation needs to be done examining the influence of higher accountability for student outcomes on principal 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.]