The 2020 global pandemic ushered in an unparalleled call to dramatically shift the focus of how school administrators responded to the COVID-19 pandemic. The transition needed to ensure the continuity of instruction in a distance learning environment demanded a new level of urgency. The long-term impact of COVID-19 presents new leadership challenges and continues to amplify the need for change during the global health crisis. This study aimed to understand the preparedness of school administrators in the United States of America as they responded to the worldwide pandemic and their perceived opportunities and challenges during the COVID-19 pandemic. This case study collected data from a survey and interviews to investigate how school leaders rose to the occasion while working through unprecedented challenges. The findings revealed several new opportunities: visionary leadership, resources to address disparities, increased community partnerships, and innovative instructional models. The challenges faced by school leaders encompassed the digital divide, staffing shortages, online instructional practices, communication with families, and staff professional development. This study offers specific implications for school leaders and educational leadership preparation programs.