A large body of quantitative evidence has demonstrated a connection between volunteering and improved well-being, especially among older adults. In the context of population aging, researchers and policymakers have looked to these findings as justification for the promotion of volunteering as a part of aging well in later life. Emphasizing the individual benefits of volunteering, researchers and policymakers have focused on questions of recruitment and retention in organizational settings, with little consideration given to what happens to well-being when older adults must retire from their volunteering, nor the implications of volunteer retirement for organizations and their staff. Moreover, current research centers the formal volunteer experience, with less attention paid to informal volunteering in older adulthood. This dissertation addresses these gaps using a mixed-method, three-paper approach. The first paper builds on existing empirical findings by adopting a qualitative inquiry approach to interview older adult hospital volunteers (age 65 and older) who engage in regularly scheduled volunteering about their experiences, motivations, and plans for future engagement. It also explores the impact of transitioning out of long-held volunteer roles on well-being. Using multiple OLS regression, the second paper analyzes data from the Successful Aging Survey to examine whether differences in volunteer engagement influence the relationship between volunteering and well-being outcomes among older adults. In addition to the differences between formal and informal volunteering, it also explores whether volunteer motivations and tasks influence this relationship. Finally, the third paper addresses the question of what happens to older adults’ well-being when they must retire from their volunteering, using longitudinal data from the National Social Life, Health, and Aging Project (NSHAP) and employing a fixed effects approach. The results of these studies have implications for individuals, management, and policy. In considering how different features of the volunteer experience influence the lives of older adults, this dissertation advances a person-centered approach to volunteer management, which moves beyond discussions of recruitment and retention to include best practices for managing transitions in and out of volunteering among older adults.