People who seriously consider killing themselves over a protracted period of time, usually years, represent great treatment challenges. Chronic suicidal ideation represents a communication of conscious and unconscious wishes that may be clarified through psychotherapy leading to various outcomes. For one group of patients, this focus will eventually change as they move gradually, over long periods of time, towards more life-affirming goals; a second group will continue to think intensely about suicide for many years, despite various psychotherapeutic interventions, without resorting to self-destructive action; and a third group will go on to attempt suicide which may or may not end in death. In this paper, we present two case studies describing the treatment of patients struggling with chronic suicidality who engaged in psychotherapy but with different outcomes. We discuss the possible outcomes and consider influential factors and suggestions for therapeutic interventions.