Across the depth-psychology corpus, ‘understanding’ emerges not as a static cognitive achievement but as a dynamic, layered, and fundamentally relational event. The term occupies a contested space between explanation and experience, between the left hemisphere’s drive to render things explicit and the right hemisphere’s more diffuse, implicit grasp of living wholes. McGilchrist, the most persistent voice on this subject, argues that understanding is the right hemisphere’s proper mode — irreducibly metaphorical, always in process, never finally grasped — and that explanation is at best a disciplined subset of it. Jaynes, arriving from a different angle, treats understanding as the felt recognition of a successful metaphor: to understand is to have substituted something familiar for something strange, a move that illuminates the cognitive mechanism while quietly relativizing all such achievements. Jung introduces a critical tension between understanding and knowledge, warning that understanding carried too far dissolves the individuated boundaries necessary for genuine encounter. Heidegger grounds understanding ontologically as Dasein’s fundamental mode of projective disclosure — not an epistemological operation but the very structure by which Being is opened. Thich Nhat Hanh embeds understanding (prajña) within a triad alongside awareness and concentration, giving it a contemplative valence that resists reduction to thought. Hillman insists that in depth-psychological work, ‘emotional understanding of the individual’ is the irreducible condition: pre-judged explanatory frameworks betray rather than serve it. Together these voices reveal understanding as the central problematic of any psychology that aspires to honesty about what it means to know another soul.