This paper critically examines the approach to studying and intervening in organizations that derives from the work of Melanie Klein. It proposes that Klein’s emphasis on reparation, while clearly valuable for effecting change, can also induce undue guilt that stymies employee subjectivity and damages the organization. The term “reparation compulsion” is offered to capture this particular dynamic. Defined as the incessant drive to atone for guilt, reparation compulsion has both individual and collective correlates that together constitute a unique and hitherto unexplored organizational pathology. Two vignettes are used to demonstrate the limits of reparation in a work setting before turning to Menzies’ classic case study of a nursing service, which is revisited in light of the pitfalls of guilt-driven labor. Together, these illustrations revise and expand upon Menzies’ concept of social defense, placing reparation compulsion at the core of a newfound “depressive” social defense system that has direct repercussions for those working in the caring professions, and particularly those afflicted with “compassion fatigue.” Specifically, the argument is made that compassion fatigue is not just an unfortunate side effect of caring, but constitutive of an organization in which repairing others requires a chronic disrepair of the self. The paper concludes with discussing the implications for the psychoanalytic study of organizations.