<p>This project examines the medieval practice of the sacrament of penance and the innovative ways in which medieval literature engaged with the pastoral project of the Catholic church to provide the penitent with a way to deal with sin. Drawing from medieval literature, religious writing and theological sources, this project begins by illustrating the extent to which each of these didactic texts produces a "model of confession" that reaffirms the teachings of the church. However, approaching these texts with careful attention to language and to the grammar of sin and penance, I show that each of these undeniably orthodox works departs from traditional accounts of the sacrament of penance in significant ways. I suggest that such departures point to moments of theological exploration. My dissertation thus interrogates the category of orthodoxy, showing it to be more capacious and exploratory than is generally recognized. Further, I suggest that the vernacular penitential literature of the late medieval period, motivated by pastoral considerations, actively engages with academic and clerical theological debates surrounding the heavily contested sacrament of penance. </p><p>Chapter one examines <italic>Jacob's Well<italic>, a fifteenth-century vernacular penitential treatise. I argue that the narrative exempla often work against the instruction offered within each chapter, compelling the reader to consider theological problems not addressed within the doctrinal material. These resistances, I suggest, are intentional and not only suggest certain limitations in traditional penitential manuals, but encourage a more conscientious penitential practice and a better understanding of church doctrine. In chapter two I consider the <italic>Showings<italic> of Julian of Norwich. I show how Julian critiques the church's penitential system and offers an alternative form of confession and penance that holds the sinner accountable for sins while reassuring the penitent of God's love and forgiveness. Chapter three compares two fifteenth-century morality plays, <italic>Mankind<italic> and the <italic>Castle of Perseverance<italic>. Through a reading of the treatment of mercy in both plays, I suggest that the Castle's departures from traditional accounts of sacramental confession allow the author to explore the scope of God's mercy and experiment with the idea of universal salvation while still promoting orthodox instruction. I conclude this dissertation with Thomas Hoccleve's poem "Lerne to Die," one of the earliest treatments of the Ars moriendi theme. Examining some of the differences between sacramental confession and deathbed confession, I show how the absence of the sacrament in this dramatic account of unprepared death emphasizes the power of God's grace and limitations of human effort. However, Hoccleve ultimately reaffirms the necessity of final confession by the end of the poem.</p> / Dissertation