Trust is increasingly recognized by scholars and practitioners alike as a vital element of high-functioning schools. Schools that cultivate high-trust environments are in a better position to accomplish the challenging task of educating a diverse group of students in a changing world. Trust supports schools’ effectiveness and persistence in reform efforts, as well as a culture of innovation and continuous learning. It is also a source of social and financial capital for schools. And most importantly, trust is closely related to student outcomes. Therefore, the study of trust is important because it can support these vital functions in schools. There are a number of conceptual and measurement issues, however, that make the study of organizational trust in schools a challenge. One of the ongoing challenges is how to best define trust, and how we might understand the characteristics trustors assess in making trust judgments. Making clear distinctions between the act of extending trust and being trustworthy is important and will help advance the study of trust relationships in schools. There are also issues with level of analysis, as trust as an organizational property may function differently than at the interpersonal level. Another challenge is the dynamic nature of organizational trust, which may change dramatically with a change in leadership or a major conflict between various factions of teachers. There are a number of promising directions for future research about organizational trust in schools. These include how to foster initial trust, how to sustain trust over time, and how to rebuild broken trust. It would also be useful to delve more deeply into the role trust plays in educator innovation and learning, and why trust seems to play such a potent role in creating the conditions for learning.