Providing caregiving for loved ones can have both positive and negative repercussions for the caregiver. Over time, long-term caregiving may lead to accumulated harms for one’s well-being. Using data from two recent waves of the National Survey of Midlife Development in the United States (MIDUS, 2004-2014), we examine whether transitions into – and out of – caregiving are associated with changes to self-esteem throughout adulthood. Findings revealed no overall differences between groups, yet: (1) Long-term caregiving (i.e., caregiving at both waves) was associated with poorer self-esteem among younger and midlife adults, but this effect weakened with age; (2) Long-term caregiving was associated with poorer self-esteem among participants with children; and (3) Transitions into caregiving eliminated the benefits of health for self-esteem. These results underscore the consequences of caregiving for adults’ well-being, and highlight the importance of context for determining which caregivers may be at greatest risk of experiencing poor self-esteem.