In this paper I will present parent work and child analytic work on behalf of a boy with a significant early complex trauma history. He endured the divorce of his parents when he was two, his mother’s diagnosis with breast cancer when he was three, and then her death when he was five years old. In describing this work, I hope to convey how knowledge of psychoanalytic child development, utilized in the context of an emotionally attuned child analytic relationship, can facilitate the kind of “return and repair” process that supports insight and healing in such cases. The case provides a detailed consideration of the assessment and treatment of a child whose early relationships and attachment patterns left him the victim of chronic emotional misattunement, living in an environment of complex trauma.