Research on the effect of COVID-19 and its aftermath on education is gaining momentum. Nevertheless, this expanding contemporary literature only scarcely addresses principals’ digital instructional leadership and has not investigated how principals’ regular instructional leadership aligns with it. Moreover, the emerging writing on the aftermath of COVID-19 notes the phenomenon of teacher shortages in schools as a result of a growing tendency of teachers to leave the profession, but the possible connection with various forms of principals’ instructional leadership remains unexplored. The purpose of this study was to examine the effect of combinations of different levels of principals’ regular instructional leadership and digital instructional leadership on teachers’ intention to leave. Cluster analysis of data of 267 school teachers in Israel was conducted. The results indicate an association between differences in teachers’ intention to leave the profession and mixtures of regular and digital instructional leadership. The results and their implications are discussed.