This chapter provides an in-depth account of a failed psychotherapy. I present a personal and theoretical reflection on the unconscious countertransference reactions that severely interfered with my capacity to sustain a reflective space or adequate therapeutic position, resulting in the total rupture of the therapeutic endeavor. I describe aspects of my personal therapy, ongoing consultations, and reading that created a reflective space in which I was later able to come to terms with my failure and learn from it. The paper ends with a brief theoretical reflection on the central aspects of what went wrong. (Originally published in the Transactional Analysis Journal, 46, #4, 2016)