The metaphor of the mirror applied to both development and the clinical process underlines Donald W. Winnicott's focus on processes between child and the environment rather than simply within the baby: between analyst and analysand. In Winnicott's view, the good-enough mother depended upon her own experiences of having been well mothered herself. In her childhood fantasies playing with dolls, he saw the girl as preparing herself imaginatively for the time she would become a mother. The chapter presents a clinical case of a baby and her mother in psychoanalytic parent–infant psychotherapy. It demonstrates the intergenerational impact of the failure of mirroring in the mother–infant relationship, and how this transmission can be interrupted through a therapeutic intervention which takes account of these processes. Winnicott's proposal of the significance of the mother's capacity to mirror her baby's states through her gaze locates the establishment of the self firmly in the matrix of their dyadic relationship.