The terrain of the Christian psyche and the theological structure within which Christians directed their lives towards salvation were both reconfigured during the Reformation. William Langland’s Piers Plowmanoffers an account of despair as a phenomenon associated with the deathbed. In the late medieval period, despair was also seen as a spiritual problem affecting religious specialists engaged in contemplative living, rather than ordinary people on their deathbeds. This article explores despair as it was understood in the late medieval period and as a key concern of Protestant theology and narrative after Reformation. It considers two sets of works written in England: a series of narrative treatments of despair related to the death of the apostate Francesco Spiera in 1548 and a set of “remedy” texts that include the Augustinian Friar William Flete’s De remediis contra temptacionesfrom the 1350s. It also examines the doctrine of “double election” proposed by John Calvin during the 1540s based on a tradition of thinking about divine omnipotence.