Despite the increasing number of studies on educational leadership during COVID-19, little attention has been paid to the intersections of different educational experiences and perspectives of school leaders, students, and their families that occur both inside and outside of schools. Drawing on eight case studies of public primary schools in Hong Kong, this article explores the challenges and strategies of online learning with a focus on effective leadership practices for supporting economically disadvantaged students during COVID-19. To incorporate the perspectives of multiple stakeholders, a series of questionnaires were distributed to principals (n = 8), teachers (n = 150), parents (n = 775), lower primary students (n = 855), and upper primary students (n = 850) and interviews were conducted with principals (n = 8), teachers (n = 37), parents (n = 32), and students (n = 62). Findings indicated that school leaders and teacher teams demonstrated strategic leadership practices prioritising and responding to the needs and constraints of economically disadvantaged students and their families. The present study draws attention to leadership encouraging collaboration among schools, families, and the wider community, which has become necessary during the shift to online learning during COVID-19. Copyright © 2022 The Author(s).