Control cases from the broad group of non-neurotic but potentially analyzable patients appear with increasing frequency. The intense, complex transferences they develop place great stress on the psychoanalytic relationship and evoke marked countertransference reactions in psychoanalytic candidates, which reverberate within the supervisory relationship. Through application of a case study method, common themes emerge in the candidate-supervisor dyad: idealization of the supervisor and of classical technique, identification with the patient, parallel process enactments, difficulty maintaining the analytic frame, and the importance of concurrent training analysis. Classical supervisory techniques must be adapted to the “difficult” (non-neurotic) control case. Complex countertransference issues must be carefully addressed while maintaining the teach/treat boundary.