Boethius' Consolation of Philosophy has long been taken as one of the seminal works of the Middle Ages, yet despite the study of many aspects of the Consolation's influence, the legacy of the figure of the writer in prison has not been explored. A group of late-medieval authors, Thomas Usk, James I of Scotland, Charles d'Orleans, George Ashby, William Thorpe, Richard Wyche, and Sir Thomas Malory, demonstrate the ways in which the imprisoned writer is presented, both within and outside the Boethian tradition. The presentation of an imprisoned autobiographical identity in each of these authors' texts, and the political motives behind such self-presentation are examined in this study, which also questions whether the texts should be considered to from a genre of early autobiographical prison literature.