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Using case material from a three-year psychotherapy treatment, this article illustrates the process undergone by a beginning psychotherapist in integrating a fallibilistic sensibility into his clinical practice. The theoretical concepts of fallibilism, the hermeneutics of trust, and pathological structures of accommodation are briefly reviewed to provide context and support for the development of this clinician’s dedication to fallibilism. Case material then focuses on the historical development of the patient’s pathological structures of accommodation and a critical clinical moment that was transformative for the trajectory of the overall treatment. Through this critical clinical moment, the therapist’s process of becoming more consciously aware of the utility of fallibilism will be illuminated. This fallibilistic sensibility is then integrated more fully into the therapist’s understanding of how this treatment changed both participants. The outcomes of the treatment will be presented, specifically related to the patient’s development of a stronger sense of self and an increased capacity to tolerate and integrate experiences of failure into his subjectivity. Ideas related to the repetitive and selfobject dimensions of the transference will also be briefly considered.