This is an evidence-based case study examining the process and outcome of 22 prenatal sessions and 1 postpartum follow-up session of psychodynamic therapy for a woman pregnant after a history of repeated pregnancy losses. Self-report measures of depression, anxiety, pregnancy-specific anxiety, prenatal attachment, trauma, and perinatal grief were completed prior to each session. A session quality item was completed after each session and a therapy outcome measure at termination and follow-up. The therapist and the patient completed an exit interview on the therapy relationship, which focused on moments of tension or misunderstanding, over the course of treatment. All sessions were transcribed and scored by certified raters for reflective functioning. Results suggest that the patient experienced reliable and clinically significant change on all pregnancy-specific measures, with most change happening in the early phase of treatment. However, general symptoms of depression and anxiety were variable and highly volatile over time. Exit interviews suggest that therapist empathy and validation were helpful in promoting change on pregnancy-specific symptoms, whereas problems or ruptures in the alliance may have been associated with a lack of change on general psychiatric symptoms. The patient showed little change on reflective functioning, perhaps contributing to ruptures in psychotherapy and lack of change on general psychiatric symptoms. (PsycInfo Database Record (c) 2020 APA, all rights reserved).