Repentance in the depth-psychology and spiritual-theology corpus is not a simple moral punctuation but a sustained ontological reorientation—a movement of the whole soul that restructures its relationship to the divine, to suffering, and to time. The Philokalic tradition, represented across all four volumes, treats repentance as unending practice: Matthew 3:2’s injunction is read as a perpetual commandment, not a discrete event, and the act is inseparable from tears, humility, and sacramental confession. John Climacus and the Desert Fathers embed repentance within a psycho-spiritual economy in which fallen persons who rise again are declared more blessed than those who never fell—a paradox with unmistakable psychological resonance. Irenée Hausherr’s study of penthos illuminates how compunction and mourning function as the affective substrate of repentance, carrying the soul toward purgative transformation while leaving permanent scars. Mark Shaw, writing from a biblical-counseling standpoint, distinguishes godly grief from worldly sorrow and interposes repentance between addiction and restoration, insisting that true repentance is behaviorally observable. William James, by contrast, questions whether even salutary remorse is not itself a pathological indulgence, proposing that moral action, not retrospective grief, constitutes the healthiest repentance. Together these voices expose the central tension: whether repentance is primarily an interior affect (compunction, mourning, tears), a volitional act (turning, confession), or a therapeutic event whose value is pragmatic rather than intrinsic.