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.