A good case history should engage the reader, get us thinking, and generate plenty to discuss, debate, and learn from. Furthermore, the author should be willing to expose the good, bad, and ugly of their work, and try to offer honest assessments of what went well and what didn’t – to expose themselves as well as their patients. Based on these requirements, Dr. Akeret’s chapter succeeds, which should come as no surprise to those familiar with his work (e.g., Akeret, 1995). Dr. Akeret was trained as a psychoanalyst in the interpersonal tradition, and follows clearly in the footsteps of Alexander and his concept of the “corrective emotional experience” (Alexander, 1946), as well as Kohut’s emphasis on the therapist’s empathy as a crucial curative factor (Kohut, 1984). He also, for good measure (and I would guess proudly), follows in the footsteps of radical analysts sometimes accused of conducting “wild analysis,” which typically signified (to detractors) a treatment in which the “rule book” had been thrown out and the analyst’s countertransference was running amok. The fascinating case presented here demonstrates all three, and ultimately hinges on a few pivotal moments when significant ruptures in the therapeutic alliance take place. In the comments that follow, I will try to explicate what I see as some possible reasons for these ruptures, and focus on three main areas: the use (and misuse) of empathy, potential problems with the “corrective emotional experience,” and how countertransference may have impacted both of these.