The author looks back on his 30 years of treating, evaluating, and consulting on over 300 cases of sexual boundary violations. He describes how his previous optimism about the potential to prevent such transgressions has given way to a pessimistic view in light of the pervasive self-deception of analysts and therapists. He also has reconsidered his longstanding categorization of these practitioners as a result of his observations about the idiosyncrasies of superego functioning and the capacity to view ethics considerations differently when applied to oneself compared to how they apply to others. Finally, he presents his impressions of how group phenomena in analytic organizations may contribute to the development of sexual boundary transgressions.