Middle-management leaders are in a crucible. In addition to managing their extensive regular duties and leading groups toward common goals, they must navigate conflicting expectations and competing demands from their superiors and subordinates. The challenges in middle-management leadership are exacerbated in fast-paced, high stakes, large-scale change environments. This multiple case study evaluated the experiences of California school principals tasked to create and lead virtual schools in 2021 as result of the COVID-19 pandemic. The principals were caught in the middle when tasked to lead and manage large-scale organizational change in high-stakes learning environments in a short window of time. Twenty-seven virtual school principals completed an open-ended survey on their experiences and 12 of the survey participants expanded on their challenges in different sets of interviews. Iterative data analysis revealed seven challenges associated with middle-management leadership: the timeline for implementation, misalignment between district and site goals, an unclear vision, lack of organizational knowledge, lack of systemic support, and poor communication. A metaphor for the crucible of middle-management leadership challenges emerged from three systemic conditions that inhibited their leadership. The conclusions provide guiding principles and recommendations to enhance middle-management leadership success in general and in fast-paced, high-stakes, large-scale organizational change environments. [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://bibliotheek.ehb.be:2222/en-US/products/dissertations/individuals.shtml.]