Today, philosophers interested in self-knowledge usually look to the scholastic tradition, where the topic is addressed in a systematic and familiar way. Contemporary conceptions of what medieval figures thought about self-knowledge thus skew toward the epistemological. In so doing, however, they often fail to capture the crucial ethical and theological importance that self-knowledge possesses throughout the Middle Ages. Human beings are not transparent to themselves: in particular, knowing oneself in the way needed for moral progress requires hard and rigorous work. Yet, medieval contemplatives insist, without this work we will never attain our final end. In this paper, I trace the connection drawn in this tradition be...