This chapter explores the difficulties posed by aversion to apologizing and the relation of this difficulty to the anticipation of shame at the self-indictment that inevitably accompanies acts of apology. Apology is an inevitable part of the process of repair that is absolutely vital to the attention to the health of the interpersonal bond and the vicissitudes of the injuries to that bond that are central and primary to the work of psychoanalysis and psychotherapy. The chapter provides some clinical examples of the failure to apologize. It considers the impact of failure to apologize on the part of either the patient or the analyst to apologize when apology is indicated in the clinical situation. The chapter then looks into the dynamics of the moral emotions, shame and guilt, insofar as they concern the problem of apology.