Though most psychoanalytic theorists have embraced homosexuality as pathological, Freud's views were less definite, more complex, and more conflicted in this regard. Rather than assuming that factors intrinsic to homosexuality underlie aberrant patterns of adult sexual expression, we explore extrinsic factors that impinge on gay men at developmentally critical periods of life, which may underlie nonnormative sexual expression. Specifically, we suggest that early caretaking environments fail to receive, affirm, and encourage same-sex libidinal attachments and expressions; moreover, such expressions are often met with shame, threat, or direct attack. Frequently, the result is the massive shutting down, compartmentalization, or both, of adult homosexual expression. Case studies are presented to illuminate this formulation. The psychoanalytic therapist who ignores the impact of developmental failures and impingements on gay men often unwittingly reenacts these, with the effect of supporting dissociative and repressive mechanisms that impair healthy adult homosexual expression.