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This empirical study focused on the experiences of school leaders as they navigated the ongoing adaptive challenges of the COVID-19 pandemic from March 2020 through the Fall of 2021. The participants were experienced high school principals in schools with established technology. The study explored the individual and systemic/district factors that enabled these principals to move forward in the pandemic. While participants described leading through the pandemic as being “very hard,” the results indicated that leaders might use the disruptions from the pandemic as catalysts for school change including resetting priorities for their leadership. The results also indicated the importance of support to and from various stakeholders when weathering ongoing and disruptive change.