The COVID-19 pandemic has altered the nature of school principals’ work. Today, principals are expected to be exceptional managers and excellent leaders in a time where the pace of change has increased exponentially. Preliminary data suggest that principals in Ontario, Canada are pivoting their work: They are engaging in a two-pronged approach to lead public schools during the pandemic crisis. They are extending their roles around (a) safe schooling and setting the context for future schooling while (b) simultaneously extending their role of instructional leader to digital instructional leader. This paper, informed by preliminary focus group data, poses thought-provoking questions that principals are wrestling with in their practice around creating conditions for students to learn and teachers to teach, while at the same time seeking out new ways to support online learning and the operations of public schooling through what they call ‘extensive digital instructional leadership’.