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In his analyses of obsessional patients, Sigmund Freud suggested that they suffered from intrusive cognitions and compulsive activities. Early psychoanalysts delineated the phenomenology of obsessionality, but did not differentiate what is currently termed obsessive-compulsive disorder from obsessional personality. However, it was widely recognized that the success of psychoanalysis with obsessional patients was limited due to rigid characterological defences and transference resistances. The present paper examines the case of a middle-aged obsessional academic who had been treated for nearly twenty years in a ‘classical’ Freudian psychoanalysis prior to entering Jungian analysis. It examines how persistent focus on Oedipal conflicts undesirably reinforced the transference resistance in this obsessional man, and suggests that focusing instead on diminishing the harshness of the super-ego via the therapeutic alliance, and fostering faith in the salutary aspects of unconscious processing has led to salutary results in this case. The biblical book of Job is adopted as ancient instruction in how to address the scrupulosity and addictive mental structuring of obsessionality in analysis.