Although the monastic characters in the Canterbury Tales have received considerable critical attention, the engagement of actual monastic readers, especially female monastic readers, with Geoffrey Chaucer’s works and works in the Chaucerian tradition has been little studied. This essay considers the ways in which women religious at the Benedictine nunnery of Amesbury and the Brigittine nunnery of Syon read and used works by Chaucer, as well as works by John Lydgate and Thomas Hoccleve that form part of the Chaucerian tradition, in the later medieval and early modern periods. Nuns in these communities read such potentially surprising texts as Chaucer’s Parliament of Fowls, Lydgate’s Siege of Thebes, and Hoccleve’s Regiment of Princes. The women religious of Amesbury and Syon drew upon these texts to develop rhetorical strategies and courses of action in complex political situations. Furthermore, the texts played important roles in the sophisticated devotional cultures of these monastic communities.