This article traces the fortunes of the bid for papal exemption from episcopal jurisdiction by St Werburgh’s abbey, Chester. It notes the rarity of new exemptions in the later Middle Ages, and the unilateral action of Abbot William Bebington in putting Chester’s 1345 bid to the generous Pope Clement VI. The exemption foundered because of the strong opposition of Edward III, the Black Prince (patron of the house) and the monastic community itself, and was withdrawn after Bebington’s removal for maladministration. That was a concession to political reality, but Bebington’s lack of consultation gave the papacy a legal pretext. Against the odds, the exemption was resurrected in 1392 at the request of Abbot Henry de Sutton, and this time it survived because the monks accepted it, Richard II did not obstruct, and Cheshire particularism swung behind it. For all the high claims to papal sovereignty that accompanied it, exemption was workable only with the consent of the crown and the local community.