Competency in psychodynamic psychotherapy is a requirement for residency training in psychiatry. However, for a variety of reasons, learning psychodynamic psychotherapy is difficult for residents. In this article, we share our experience in an elective in Transference-Focused Psychotherapy (TFP), a manualized treatment for severe personality disorders. Originally, this elective was conceptualized as an advanced component of training, offering specialized training in treating a subgroup of patients with severe personality disorders with a specific type of psychodynamic psychotherapy. However, contrary to the expectations of the residents and the training director, the elective in TFP strengthened understanding of core components of basic psychodynamic psychotherapy with all patients, not just those with severe personality disorders. We discuss various challenges in learning psychodynamic psychotherapy and how TFP served to address them. Two case vignettes illustrate several key points.