Meeting the demands of chronic illness and disease states is challenging, at best. Too often, the chronicity of the illness hastens death. The physical, psychological, and sociological changes that accompany the death of an individual require attention and forethought if the life transition is to be made with elegance and grace. This article addresses the caregiving demands for the professional and familial/social support surrounding the chronically ill individual at the end of life. Focus is placed on the preparation of advance directives—legal documents that set clear boundaries for honoring the wishes of the patient. © 2002 Wiley Periodicals, Inc. J Clin Psychol/In Session 58: 1421–1431, 2002.