In this article, we draw on the literature on trust to examine how elementary school principals make sense of superintendent trustworthiness. We examine trust in the context of the principal-superintendent relationship because it is the "social glue" needed for effective professional relationships where student learning and success is at the core. We used purposeful sampling and conducted fifteen in-depth, semi-structured interviews with five elementary school principals. Drawing on constructivist grounded theory guidelines, we describe the principals' foundations of superintendent trustworthiness, including how they conceptualize trust, the importance of superintendent competence, and shared values between both parties. Participants viewed trust as a reciprocal two-way path, requiring vulnerability from both parties and occurring over time. The experiences of the five participants are helpful for principals and superintendents who wish to strengthen trust relations for the purposes of their leadership and for creating healthy, thriving school communities.