Penis envy occupies a contested yet structurally central position in the depth-psychology corpus, functioning simultaneously as a clinical observation, a metapsychological axiom, and — for later revisionists — a site of ideological critique. Freud introduced it as the female child’s response to perceived anatomical deficiency, asserting in texts from the Three Essays through the posthumous Outline that the girl’s entire development unfolds ‘under the colours of envy for the penis.’ Abraham elaborated its neurotic transformations with clinical precision, documenting how unresolved castration-complex dynamics generate frigidity, masculine protest, and revenge fantasies toward men. Klein preserved the term but relocated its gravity: for her, penis envy is secondary to the more primary oral envy of the breast, and it operates within an already-constituted object-relational world shaped by projective and introjective processes. Ferenczi introduced a social-critical inflection, suggesting that some phenomena attributed to penis envy may reflect the daughter’s contempt for a father weakened by maternal dominance. Hillman, the most systematic critic, argued that penis envy is the symptomatic expression of a deeper ‘repudiation of femininity’ that infects not only the patient but the analytic method itself, and that analysis cannot reach its end while it remains structurally masculine. Across this range, the term raises irresolvable tensions between biological determinism and cultural construction, between oral and genital developmental primacy, and between descriptive clinical category and normative gender ideology.