The parent–therapist relationship is one of the most important facets of child psychotherapy. Guilt and shame are common sources of rupture between parents and child therapists. Overlooking such ruptures with parents can interfere with or even halt psychotherapy with children. A review of empirical and theoretical literature on ruptures in the therapeutic relationship is followed by discussion of how clinicians might identify guilt- and shame-based ruptures in the parent–therapist relationship. The process of repairing parent-therapist ruptures is emphasized as one process that can assist parental growth and development, which in turn can create space for children to grow and develop in tandem with their parent(s). A case study illustrates how guilt and shame manifest in the form of a race-based rupture in the parent–therapist relationship. A discussion of guilt, shame, and oppression concludes this article.