The past three decades have witnessed a growing body of literature on pastoral health and longevity in ministry. However, little attention is devoted to the connection between educational expectations formed in seminary and ministry realities experienced in and among congregations. Clearly, pastoral ministry is a difficult, tiring, and sometimes thank-less work which requires unique preparation. This study explores the lived experiences of seven graduates of a particular seminary who were ordained to pastoral ministry. The participants, while grateful for their theological preparation, reported dissatisfaction about the adequacy of their education for the complexities of ministry. In this work, the background and history of literature on pastoral life, health, and education is explored, along with the fruit of interviews with current pastors who participated in the study. What emerges is an interesting and relevant perspective into the helpful and not-so-helpful aspects of seminary life and preparation and their bearing on the complex realities of pastoral life.