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The research will examine how school principals in school systems experiencing ongoing crises adapt their leadership practices, and how they implement and reimagine “best practices” learned through professional development. We focus on school principals in Puerto Rico, a US territory with recent history of economic, political, and environmental crises. Applying complex systems theory, we explore how school principals have navigated multiple overlapping crises while implementing the knowledge of best practices gained through the professional development program. The findings will help clarify how leadership practices can be adapted during times of crisis, which is of critical importance as school systems around the world are trying to adapt to the effects of the current global pandemic.