This paper examines the repetition compulsion as a composite structure and explores the elements that are involved in it. After examining the difference between playful repetition, which promotes psychic development, and the repetition compulsion, which obstructs psychic change, the author discusses Freud’s models of the repetition compulsion (as the return of the repressed vs an expression of the death drive). Further elements that contribute to the repetition compulsion include the role of a primitive, punitive superego, the persistence of raw, unsymbolized elements, obsessional doubt, the retreat into timeless states of mind as well as a re-entry mechanism in certain psychotic patients. Finally, the failure of reparative processes seems to be a central mechanism in sustaining the repetition compulsion. Brief clinical vignettes illustrate the author’s arguments.