Masochism is a complex, dimensional psychological phenomenon. At the severe end of the spectrum, it is better conceptualized as sadomasochism, involving severe self-destructive behaviors driven by hidden pleasure and underlying conflicts, presenting diagnostic and treatment challenges. This article elucidates its clinical manifestations and discusses the implicated conflicts and defenses. It explores the effectiveness of transference-focused psychotherapy (TFP) in managing sadomasochistic personality, emphasizing the importance of considering the level of personality organization. Using a case example, we illustrate the potential of TFP for symptom amelioration and improvement of interpersonal relationships in individuals with sadomasochistic personalities, as well as addressing emerging resistances in treatment. Furthermore, the article underscores the imperative for further research to understand and address this intricate phenomenon.