Psychotherapy with the terminally ill poses special challenges for clinicians and in return offers unique rewards. As a time limited therapy, acceptance, rather than change is a primary goal; yet, patients can be strongly motivated to change. Patients may need to struggle with how to disengage while also maintaining connection. Unique transference and countertransference issues arise. The psychological tasks of dying include grieving, saying goodbye, constructing a meaningful context to one's life, and letting go. The therapist can serve as a companion and guide to the dying person as she or he negotiates these tasks. Through the use of a case example, these issues are explored from the perspectives of patient and therapist. The therapist must address the following issues: attending to physical suffering, differentiating between grieving and depression, addressing fears, facilitating the life review, and assisting in decision making. A dying patient's need to leave a legacy, complete relationships, grapple with spiritual and religious issues, and attend to his or her family, are often important themes. Therapists must work productively with denial, maintain flexible yet appropriate boundaries, grapple with their own anxiety about death, and grieve the loss of their patients. Psychotherapy with dying patients can help reduce their psychological pain, relieving psychosocial distress and providing opportunities for personal growth in the last stage of life. Such work is often draining yet immensely rewarding for the patient and therapist alike.