This article describes a 9-month longitudinal study, which in part examined how seminary students (N=60) connect classroom learning with field education experiences. Findings indicate that many students began field education either underestimating the connections between their courses and ministry in the field or overestimating their ability to move between theory and practice. Over time, students gained a deeper appreciation of the nuanced connections between classroom and experiential learning. Some students emerged from this deeper sense of connection disillusioned by disconnects between real-life ministry and their classroom learning. This disillusionment is important for educators to expect, understand, and address.