In this article John Bailey discusses how schools can successfully reopen following the COVID-19 pandemic. Bailey asserts that the rethinking of schooling that was forced by the pandemic can serve as an opportunity to introduce some long-overdue reforms and improvements to better serve students, particularly students of color. The task is not reopening schools as normal but building an education system that is more resilient and equitable. Bailey goes on to discuss four primary medical questions relevant to schools' planning efforts, the answers to which come from medical studies as well as the experiences of schools that reopened abroad in May 2020. He goes on to discuss reopening resilient schools; communication and collaboration; supporting the whole child; protecting vulnerable school personnel; addressing academic challenges; improving distance education; and preparing for cautious parents. Bailey concludes that the students who need the most help are those who have been systemically underserved for generations. Organizations rarely have the permission to rethink all their assumptions, structures, and systems. The COVID-19 crisis gives that permission to school systems to think differently and introduce long-needed changes and improvements. The real question is not can schools do this, but rather, how will schools rise to the challenge of the moment?