Modern critics usually read the vision of Dryhthelm as an account of a man frightened into penitential asceticism even though Bede explains that Dryhthelm lived out his days in the desire for heaven, not fear of punishment. While fear is an important part of Dryhthelm's conversion, Bede depicts the process according to the doctrine of compunction as it is received from Gregory the Great, who presents compunction as a process by which fear of punishment yields to love and the desire for heaven. Reading the conversion of Dryhthelm as a process of Gregorian compunction reveals both Bede's fundamental optimism about the vision Dryhthelm has seen and a spirituality in the text that is more nuanced and positive than the fire and ice that figure so prominently in it. Proceeding from these observations, the paper argues that the celestial topography of Dryhthelm's vision is a spiritual topography — a map of personal and emotional progress through compunction, as understood by Gregory the Great and received by Bede, and only incidentally a map of celestial regions deemed logically necessary by later theologians. These conclusions complicate hellfire and brimstone readings of this and other Anglo-Saxon texts about judgment and penance, and they call for nuanced readings of compunction as a complex and productive experience.