Within the depth-psychology corpus, free will occupies a contested threshold between phenomenological experience and metaphysical or neurological determinism. Jung establishes the foundational position: the ego possesses free will within the field of consciousness, but this freedom is sharply circumscribed by the self, which acts upon the ego ‘like an objective occurrence which free will can do very little to alter.’ Von Franz extends this by insisting that the philosophical debate is irresolvable — free will can be neither proved nor disproved — and redirects inquiry toward the subjective experience of choosing freely, especially in moments of instinctual conflict. The neuroscientific challenge posed by Libet’s experiments, cited by Levine and Gallagher, threatens to dissolve voluntary agency entirely into pre-conscious neurological readiness potentials. Yalom surveys how analytic theory has struggled to accommodate a freely choosing subject within an otherwise deterministic metapsychology. Aurobindo and Plotinus represent the contemplative-metaphysical pole, arguing that genuine freedom emerges only through alignment with a deeper spiritual principle — the Purusha, the Good, or the divine — rather than through the ego’s apparent choices. Dihle’s historical survey traces the concept from Aristotelian proairesis through Stoic, Gnostic, and Augustinian formulations, showing free will’s emergence as a coherent concept to be distinctively Augustinian. Maté situates the question clinically: addiction demonstrates that freedom of choice requires intact cortical infrastructure. The tension throughout is whether freedom is a psychological datum, a spiritual achievement, or a useful fiction.