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The COVID-19 pandemic exposed deep vulnerabilities in K–12 education and demanded leadership beyond technical problem-solving. This study examines how two districts—Washington and Hamilton—responded to the crisis over five years (2020–2025). Using interview (N = 253) and survey (N = 233) data, we analyze how preexisting organizational capacity shaped leaders’ ability to foster resilience. Findings show that resilience is not just recovery, but the capacity to adapt, learn, and sustain coherence amid uncertainty. Washington relied on strong infrastructures and collaborative routines, while Hamilton emphasized improvisation and relational trust. Despite different conditions, both developed adaptive strategies. This study contributes to scholarship framing resilience as a systemic capacity rooted in leadership practice, highlighting how schools can prepare for both foreseeable and unforeseeable disruptions.