Two distinctive late-life challenges, community relocation and caring for an adult child with mental retardation, were studied to determine their influence on coping and well-being. These challenges differ in terms of their normativeness, duration, and whether they were expected. Data from 2 ongoing longitudinal studies (N = 449) were used to test the hypotheses that women experiencing residential relocation would report higher well-being and use problem-focused coping more frequently than women with long-term caregiving responsibilities. As predicted, more positive changes in well-being across time were reported by the relocation sample, which also showed more problem-focused coping. Women in the caregiving sample, however, showed stronger relationships between coping and well-being, underscoring possible gains in expertise that accompany challenges of lengthy duration.