Emmy Gut was a psychotherapist who developed, in her later years, a unique theory distinguishing between "productive" and "unproductive" depression. Dr. John Bowlby was a leading psychoanalyst famous for his work on attachment theory. After the death of her second husband, Emmy contacted John because his work on mourning and grief spoke to her own depressed state. Although her views of the world and of her relationship with John were clearly coloured by bouts of depression, she was profoundly influenced by her personal, therapeutic, and intellectual involvement with him. Evidence of his influence is seen in the volumes of correspondence flowing between them beginning in 1971 and continuing until John's death in 1990. During that time, Emmy wrote more than 100-some very lengthy-letters to John. Much of her correspondence was devoted to discussions about their often ambiguous and conflicted therapeutic relationship. Through an analysis of attachment theory and the nature of the client-therapist alliance, this paper offers insights into the effects that imbalances in power, expectations, and shifting needs can play in the recovery process.