Advances in voice recognition and artificial intelligence (AI) could soon yield digital conversation companions—software that combines conversational AI with health monitoring and promotion. We describe how this technology, once developed and deployed, could transform the way older adults age and receive care. By obviating the need to read or type, the software could be used by individuals with reduced dexterity, vision, or literacy. Repeated conversations could facilitate the consistent longitudinal tracking of mental acuity and sentiment. Over time, the conversations could be tailored to strengthen cognitive reserve, physical resilience, and social lives. By continuously recording and relaying changes in cognitive function, digital conversation companions could offer older adults unprecedented visibility into their own aging trajectories. Drawing on three well-known conceptualizations of aging, we explore how older adults might respond to this new dimension, a process we term “reflected aging.” Digital conversation companions could support caregivers by monitoring care recipients’ mental health, explaining treatment options, and automating documentation. They also might engender an atmosphere of constant surveillance and discount caregiver expertise and judgment. As digital conversation companions could lead to anthropomorphism, delusion, or social withdrawal in users of any age, these risks should be monitored closely in vulnerable older adults.