Ambiguity occupies a pivotal and contested position across the depth-psychology corpus, functioning simultaneously as epistemological problem, psychological virtue, and ontological condition. The tradition refuses to reduce ambiguity to mere linguistic indeterminacy; instead, its major voices treat the capacity to sustain ambiguity as a mark of psychological and intellectual maturity. McGilchrist draws directly on Keats’s ‘negative capability’ to argue that ambiguity is inseparable from the complexity of truth itself, situating it as the necessary medium through which unconscious reality is accessed. Hillman, developing his archetypal psychology, elevates Dionysus to the status of the ‘God of Ambiguity,’ whose double-tongued epithets refuse the either/or logic of rational mentality and express the indivisible coexistence of generation and decomposition. Detienne locates ambiguity at the structural heart of archaic Greek speech, showing that sophistry and rhetoric were not corruptions of truth but systematic theorizations of ambiguity as the medium of political life. From the Stoics and Hellenistic philosophers come technical taxonomies of ambiguous expression—eight types catalogued, semantics distinguished—showing that the logical tradition recognized ambiguity as a formal problem requiring disciplined resolution. Hollis, approaching from clinical depth psychology, identifies the inability to tolerate ambiguity as a driver of manipulative, controlling behavior in intimate life. Taken together, these voices reveal a central tension: whether ambiguity is a deficiency to be resolved by precision and reason, or an irreducible feature of living reality that must be inhabited with what Keats called ‘uncertainties, mysteries, doubts.’