This dissertation pursues two distinct but parallel projects in relation to the work of Bernard of Clairvaux and Middle English imaginative literature. First, I argue for a Bernardine anagogical lens as a way to better understand the deepest theological commitments and most distinctive formal innovations of certain key Middle English literary texts, especially Piers Plowman and The Canterbury Tales. Second, I outline a more genealogical project, tracing the figure of Bernard as it is explicitly invoked in widely circulated Middle English works including Piers, The Parson’s Tale, and the Prick of Conscience. These two threads connect to suggest that the work of Bernard of Clairvaux can offer a new way to understand the relationship between theological and literary texts in the late Middle Ages. Because Bernard’s influence in the vernacular is as much as matter of style as of content, it requires a more capacious way of theorizing the theological implications and even motivations of literary form. The “figure of Bernard” acts as a cipher for later works to explore their deepest intellectual preoccupations, and makes it possible to trace the way they imagine the anagogical interval between the presence and absence of Christ, the over- and under-estimation of the presence of eternity in time. The Bernardine themes of “presumption” and “despair” serve as a useful shorthand for signaling this theorization, and help me to extend its application beyond texts in which Bernard is explicitly invoked—including to writers, like Chaucer and Thomas Malory, whose work is often assumed to be firmly secular.