The extent, nature and significance of Chaucer's connection to the Lollard movement have long been the subject of speculation and debate. Even before John Foxe, in his sixteenth-century Actes and Monumentes, referred to Chaucer as ‘a right Wicklevian, or else there was never any’, Chaucer was already seen as providing a record of the dissenting voices of late-fourteenth-century England. In fact, in 1464 a copy of the Canterbury Tales belonging to one John Baron of Amersham was produced as evidence for the prosecution in a case of heresy. Although, as Derek Pearsall asserts, the legend of the Protestant Chaucer faded in the seventeenth century ‘when it was no longer historically relevant’, the interest in Chaucer's employment of Lollard ideas and motifs continues.

Why Chaucer's engagement with this movement continues to fascinate is clear. The theologian, John Wyclif, along with his followers, provided a new challenge to the authority of the Church. This challenge was more potentially calamitous than the petty squabbles among the religious orders or the criticisms of the clergy that had stimulated ecclesiastical debate throughout the Middle Ages. The Lollards challenged the foundation of the power of the medieval Church, demanding that it return itself to the state in which it was born of Christ in the Gospels. The subsequent questioning of papal authority, the challenge to ecclesiastical hierarchy and the condemnation of religious orders as superfluous to the operation of the Church were fuel enough, but the denial of the doctrine of transubstantiation was a step too far.

It seemed as though, by denying the miraculous power of the clergy, Wyclif and the Lollards were trying to usurp clerical authority and to return it to the lay person. The call for vernacularity was therefore the ultimate threat, and the Wycliffite project of translating the Bible into English – so that every layman could engage with the one resource upon which his or her faith ought to be grounded – would arguably be the final straw. By promoting and facilitating access to Scripture, the Lollards were, in fact, empowering the laity to stand against ecclesiastical corruption and clerical misconduct. The Church reacted vehemently, with the contemporary chronicler Henry Knighton suggesting that in having facilitated access to Scripture, Wyclif had ‘spread the Evangelists’ Pearls to be trampled by swine’