Later life is seen as the forerunner to multiple transitions involving loss and grief that have implications for the health and well-being status of older people. Common transitional challenges in later life involve bereavement, retirement, and relocation, including losses relating to the aging process per se. In essence, life-related transitions in later life present a range of possibilities for growth or decline in developmental capacities. This critical commentary draws attention to the need for awareness among health professionals and family caregivers to understand the potential for a disconnect of empathy and compassion from the existential loss and grief experiences of people in later life. A case is made for healthcare workers to explore the aging process more carefully and thoughtfully, with particular attention to the relationship of compassionate care to the existential aspects of loss and grief in later life. Shortfalls in the healthcare system are shown to hinder or endanger the provision of a high-quality, compassionate care culture for older people. It is suggested that any serious psychology of aging requires improved depths of study and understanding surrounding the existential dimensions of loss, grief, and bereavement.