As social and political beings, we are able to flourish only if we collaborate with others. Trust, understood as a virtue, incorporates appropriate rational emotional dispositions such as compassion as well as action that is contextual, situated in a time and place. We judge responses as appropriate and characters as trustworthy or untrustworthy based on these factors (namely context, intention, action as well as consequence). To be considered worthy of trust, as an individual or an institution, one must do the right thing at the right time for the right reasons, and the action should have its intended effect. By focussing on character, including a moral agent’s emotional disposition, virtue ethicists offer a more holistic account of trust than that explained by a deontic adherence to one’s duty as governed by a social contract. I will apply this understanding to educational institutions, particularly primary and secondary schools that serve a vital role in society. One of the main roles schools perform is to assist in character formation so that students, through practice, learn to be trusting and trusted citizens of society. I offer the philosophy in schools’ methodology of the community of inquiry as one example of how such practice may be facilitated in the classroom.