This article discusses the case of a boy who, during the course of a five-year treatment, alternated, at times moment to moment, between desiring connection and rejection of that connection. It illustrates how, in the context of an empathic, caring relationship, chaos and thoughts of annihilation arose, rather than a more positive therapeutic outcome. This prompts the question of what happens to a child in the context of a treatment relationship when he repeatedly experiences empathic attunement and understanding before he is ready to receive it; when something more than what one has repeatedly experienced in his interpersonal world does not contribute to an increasing sense of coherence and stability and instead precipitates a crisis for the child.