As a fundamental concept in human interactions, trust is important for understanding and mediating the social structures in schools. The instrumental work of cultivating, brokering, and maintaining trust in schools lies within the role of the school administrator. Our exploratory study examined the Canadian school principals' perceptions of their moral agency and trust-brokering roles in schools. Upon reviewing the literature on the imperative of trust in school settings, we offer a phenomenological analysis of selected research findings. These findings are based on the responses of Canadian school principals (N = 177) who had reflected on their lived experiences of the personal, relational, decisional, educational, organizational, and moral imperatives of trust for school leaders.