This article explores the therapeutic limits of psychoanalysis by examining Sigmund Freud's conceptualization of the negative therapeutic reaction and its subsequent developments. Freud consistently maintained a realistic, often pessimistic, stance regarding the efficacy of analytic therapy, mapping its boundaries across various theoretical models. The negative therapeutic reaction stands out as a formidable resistance rooted in severe superego cruelty and unconscious guilt, posing significant ethical and clinical challenges. To address these boundaries, this study establishes a comparative dialogue between two major psychoanalytic figures: Sándor Ferenczi and Jacques Lacan. It investigates how both authors positioned themselves regarding the field of problems introduced by Freud's concept, specifically focusing on the tension between submission and freedom within the analytical process. Methodologically, the paper first revisits the Freudian structure of the negative therapeutic reaction and its links to the superego. It then analyzes Ferenczi's clinical and theoretical adaptations, followed by an exploration of Lacan's early work up to 1964. Ultimately, this comparative framework detects crucial proximities and conceptual tensions, shedding light on historical efforts to expand psychoanalytic treatment to previously unanalysable conditions.