There is a distinct gap in existing research exploring how a prolonged crisis can pose unique challenges and learning opportunities for school leaders. This qualitative study sought to convey four school leaders' lived experiences and answer the question: What are the perceptions of four school leaders in a metropolitan area of the challenges associated with leading schools through a sustained, global pandemic? Rooted in the Social Constructivist Framework, we completed individual qualitative, auto-ethnographic case stories spanning a year's time from March 2020 to March 2021. We conducted independent and cross-case analyses, assessing the common challenges faced. Five key challenges emerged through our research: no plan, constant reaction, managing rather than leading, supporting others, and the negative impact this had on physical and mental wellness. Specific recommendations include the addition of Crisis Management in principal certification, development of emergency learning plans, the establishment of school support systems, and employment of district researchers. [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.]