The social relevance of trust and the principals’ obligation to foster trust in schools have been strongly advocated. This paper describes an in-depth, qualitative study that engaged a group of twenty-five Canadian school principals over a period of seven months, exploring the issues of trust as it affects principals’ roles and responsibilities. Four central concerns were identified by the participants: i) defining trust, ii) establishing trust, iii) maintaining trust, and iv) trust breaking. The principals’ multiple relationships produce a complex web of issues related to trust; including intensity of relationships and the contingent role of school principals in trust brokering within learning communities. This research has further established a basis for on-going examination of the nature, extent, and effect of trust relationships in the lives of school administrators.