This dissertation offers the first full-length study of medieval England’s literary tradition of manuals for penitents—texts describing the sins, and other essentials of the faith, that address penitents preparing for confession. This tradition includes works that were among the most popular in medieval England. Some of these—including the Parson’s Tale and Ancrene Wisse, which is an important precursor to this body of writing—have been studied in depth, but the tradition in which they participate is still not well understood. This dissertation shows that this tradition emerged in a significant way in the second half of the thirteenth century, although it took root in an existing body of self-examination writing. Insofar as it reflects a new emphasis on reading as a means of interrogating oneself rather than as a means of preparing oneself to interrogate others, the development of these manuals represents a widening range of reading practices and a shift toward private confessional education. The first two chapters describe the characteristics of manuals for penitents, including their material and formal qualities. Among other contributions, the first chapter explores a feature of commentaries on the essentials of the faith that often goes unnoticed: that when they appear in manuals for penitents, they are not, as is often thought, digressive, impersonal, or strictly didactic, but instead encourage and promote self-reflection. The second chapter examines the implied and actual audiences of manuals for penitents. On the basis of this more precise characterization of these manuals, the final three chapters offer insight into three interlinked texts chosen from different stages of the development of these manuals: Ancrene Wisse, the Compileison, and the Parson’s Tale. In addition to shedding light on these three texts, these concluding chapters highlight some of the tensions that emerged surrounding the shift to asynchronous penitential learning that was enabled by these manuals.