Since 2016, I have been serving as principal at Davis Elementary School, a Title 1 school in Portland, Oregon. This autoethnography is a reflective account of my role as a principal during COVID-19 school closures and reopening. School systems and school leaders had to become more adaptive to change and had to find ways to creatively deal with COVID-19 challenges. Utilizing the conceptual frameworks of (a) culture of care informed by the constructs of ethic of care, cultural wealth in critical race theory, and culturally responsive leadership; and (b) prosocial leadership, this autoethnography used self-reflection and thematic analysis to elucidate the shared experiences and challenges of many education professionals. Through writing this autoethnography, I explored my own entanglements in the day-to-day nuances of addressing a crisis never before experienced by our modern educational system. Thematic analysis revealed an overarching theme of an ethic of care that undergirded all aspects of my prosocial leadership style and philosophy, the strategies I used to sustain my school community through school closure and reopening, and my approach to supporting students, families, and staff. Five additional themes emerged: communication and connection, leadership, self-care, creating and sustaining a culture of care, and equity. By telling my story, I hope to grow as a leader and gain a more holistic understanding of leadership in times of challenges, emergencies, and crises. This study also contributes to the newly developing body of research about leadership during the COVID-19 pandemic and ways school leaders can effectively support their school communities. [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.bibliotheek.ehb.be/en-US/products/dissertations/individuals.shtml.]