Purpose: In this article, I examine the importance of cultivating critical hope while leading a school through a crisis. I analyze how the concept of critical hope functions when principals use it as a lever to lead toward crisis recovery. The analysis is informed by literature from the fields of education and positive psychology. Research Methods/Approach: For this qualitative study, I used a cross-comparative approach to uncover how principals operationalize critical hope to engender hope throughout their school buildings and maintain a sense of hopefulness to continue leading. To do so, I interviewed 50 principals from across the United States who have led through at least one crisis. Findings: I found that principals are constantly cultivating and engendering critical hope for their schools and for themselves. The findings also suggest that critical hope is essential to a principal leading through a crisis. Implications: This research contributes to our understanding of the relationship between critical hope, crisis, and educational leadership. It also extends research on leadership competencies and dispositions toward effective school leadership postcrisis.