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The New York State Education Department (NYSED) issued 68 policy statements during the first five months of the pandemic. Analyzing the timing and theme of each policy exposed that issues related to finances and accountability were communicated with double the frequency than issues related to instruction, health, or special education. The author, a school principal during the pandemic, offers novel insights to these policy statements that forever altered the job of the principal. Implications for crisis preparedness and the broader role of schools in society are discussed. This is a timely retrospective analysis from a frontline practitioner-scholar, coinciding with the official release of the After Action Report of New York State’s overall handling of the COVID-19 pandemic.