Efforts to improve end-of-life care have been hindered by widespread delays in discussing and initiating this care. The dynamics of hope and hopelessness may be crucial in these delays. The author reviews recent literature concerning hope and hopelessness at the end of life. Modern dying is more prolonged and more shaped by human choice than ever before. Therefore, hope and hopelessness play a more active role in the dying process. Hopelessness is not a simple product of prognosis, but is shaped by state and trait psychological factors. Hope at the end of life can come in various forms: for cure, for survival, for comfort, for dignity, for intimacy, or for salvation. Hopelessness at the end of life is therefore not simply the absence of hope, but attachment to a form of hope that is lost. The concept of anticipatory grief may help us interpret hope and hopelessness at the end of life. Improving end-of-life care will require looking beyond prognosis and preferences to understand the dynamics of hope and hopelessness. To be successful at diversifying hope at the end of life, we must foster the trusting interpersonal environment where this is possible.