A case vignette of a woman with multiple developmental traumas is presented to illustrate the potential collusion of her self-protective retreats and powerful projections with the analyst’s own countertransference, which was colored by his transgenerational adaptation to a totalitarian political condition. The author, an analyst from the Czech Republic, explores his passive interpretative stance and extended capacity to tolerate the patient’s retreat and her fear of disclosing her true thoughts in light of “false adaptations” known in former Communist states. Psychoanalytic models of intrapsychic functioning of residents and psychoanalysts under the Communist regime are described. Finally, the author examines how his analytic functioning is impacted by his own ancestors’ adaptations, his own upbringing, and his own psychoanalytic training.