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Fourteenth-century English society bore witness simultaneously to a marked increase of dedicated prison spaces and a proliferation of imaginative writing in English. Volumes of study have focused on the social implications of carceral practice, and many studies have also been dedicated to the rapid development of English as a literary and philosophical vehicle in the late Middle Ages. This study seeks to bridge these areas of scholarship by focusing on the political implications of early English prison writing. Close readings of Chaucer’s “Boethian” texts and Thomas Usk’s Testament of Love, matched for their close overlaps in subject matter, audience, dates of composition, and literary antecedent, demonstrate that the close relationship between carceral experience and social status was inherent in the foundational texts of English prison literature. Chaucer’s position as a political insider, and the rhetorical skill garnered from his formal and informal educations, allowed for more latitude in written expression than did Usk’s notorious bent for factionalism and his comparatively expedient use of writing, literary and legal, for personal aims. This point is emphasized dramatically by juxtaposing the histories of the texts themselves with the political, legal and carceral histories of the authors. This study draws on multiple realms of scholarship including social histories of medieval Britain, Chaucerian studies, histories of English imprisonment, vernacular, hagiographic, and legal studies; combining these indicates that even as English was first used to articulate a philosophy of prison for readers of English prose, its reception was always already connected to the social status and political relationships of the author.