Facing his own mortality in the experience of a “spotted fever,” John Donne composed his Devotions upon emergent occasions in 1623. Although the work is typically read in the chronological context of Donne’s oeuvre as a meditative text composed by “Dr. Donne,” the Dean of Saint Paul’s, this article suggests that, when read in relation to the ars moriendi, or “art of dying well,” the Devotions demonstrates itself to be more consonant with the paradoxical work of the younger Donne. The art of dying well traditionally demanded the exclusion of fear and doubt, requiring that the dying individual face mortality placidly, obediently, even joyfully, in order to ensure salvation. I argue that the Devotions challenges the efficacy of the ars as a model for achieving spiritual health on the deathbed, showing how its elisions of the particularities of suffering cannot universally serve the sick and dying. Instead, Donne presents an alternative, which, like his early Holy Sonnets, incorporates the experience of fear, impatience, and doubt into the aims of the text and suggests that the end of life cannot, and perhaps should not, be approached as calmly as the “ideal” model demands.