Narcissistic Personality Disorder (NPD) is characterized by a persistent pattern of grandiosity, fantasies of unlimited power or importance, and the need for admiration or special treatment. Individuals with NPD may experience significant psychological distress related to interpersonal conflict and functional impairment. Research suggests core features of the disorder are associated with poor prognosis in therapy, including slow progress to behavioral change, premature patient-initiated termination, and negative therapeutic alliance. The current manuscript will explore challenges of working with NPD within the context of life-limiting illness for two psychotherapy patients seen in a behavioral health clinic at a large academic health science center. The ways in which their personality disorder affected their illness-experience shared significant overlap characterized by resistance to psychotherapeutic change, inconsistent adherence to medical recommendations, and volatile relationships with providers.