COVID-19 has produced mayhem and uncertainty for educational leaders in charge of organizations. This inquiry sought to provide insight into how superintendents and assistant superintendents made sense of their environments during the COVID-19 pandemic. Specifically, sensemaking theory (Weick, 1995) was utilized as the conceptual framework to bring clarity and meaning-making for educational leaders as they led their organizations through local, state, national, and international crises. To this end, the focus of this inquiry was to gather school leader's insights into how they provided clarity to a disordered world, understood how they addressed vulnerable populations during the pandemic, recognized the role emotion played in constructing their realities, and determined if location within the state of Missouri played a role in the sensemaking process of superintendents and assistant superintendents. The researcher interviewed 23 participants in the state of Missouri and collected documents to answer the five research questions of the study. The study concluded participants made sense of the pandemic through a collaborative process using a political framework. Additionally, superintendents and assistant superintendents saw all students as vulnerable during the pandemic and expressed a variety of negative emotions. Finally, little variance occurred in superintendent sensemaking between small, medium, and large school districts. [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.]