The psychoanalytic literature has discussed many dynamic aspects of encopresis, but no one has explored the meaning of the underlying insecure attachment patterns that predispose the child to encopresis. This article offers an attachment perspective to understand the etiology of primary encopresis and suggests relationship-focused intervention strategies to break through the child’s fortress of denial, omnipotent control, and sadomasochism designed to create emotional distance from the therapist. Two clinical cases of primary encopresis are presented to illustrate the severe relationship difficulties that inevitably develop between therapist and patient and the countertransference reactions likely to emerge. In both cases, traditional interpretive strategies were ineffective in establishing an emotional connection. Instead, engagement through imaginative play and humor were used to draw these children out of their defensive hiding place and bring them into a genuine, reciprocal relationship with a person who could help them to regulate underlying painful affects such as separation, rejection, and loss. Traditional interpretive strategies can be attempted only after the patient’s capacity to mentalize these affects has been revived.