Through its overarching frame story but also in the interplay among its diverse tales, the Canterbury Tales again and again troubles our sense of how endings work, promising resolutions that never quite materialize or are undercut as soon as they do. This feature of the Tales offers us the opportunity to consider endings less as a single narrative feature than as a set of persistent and varied problems related to composition, to language, to audience, and to poetry, as a way of considering the cadence of life itself. We follow Rosemarie McGerr in asserting that a certain kind of “irresolution” is a defining feature of the Chaucerian poetic, a poetic of openness and ambiguity, a consideration of the limits and problems of teleology for the poetic enterprise, for an audience of hearers, or for human living. The poet’s troubles with endings date from the start of his career, with his earliest major poem, the Book of the Duchess, offering a particularly useful example, and they extend past the poet’s own ending, as Chaucer’s fifteenth-century audience saw the Canterbury Tales both as an “open” text, ripe for additions, and as an “unfinished” text, a structure begging to be completed.