This 3-year longitudinal study examined the associations between regret management, everyday activities, and retirement satisfaction among recent retirees. We hypothesized that the regulation of a severe life regret can facilitate activity engagement and retirement satisfaction, but only if retirees manage their regrets adaptively by either increasing effort and commitment when possessing favorable opportunities or disengaging when opportunity is unfavorable. Cross-sectional analyses demonstrated that the highest baseline levels of activity (e.g., volunteering, traveling) and retirement satisfaction were observed among participants who perceived favorable opportunities for addressing their life regrets and had high levels of engagement. Longitudinal analyses showed that this pattern was also associated with increases in activity engagement. In contrast, disengagement protected individuals with unfavorable opportunity from 3-year declines in retirement satisfaction. These findings indicate that adaptive regulation of regrets can both contribute to gains and prevent losses in the early stages of retirement, which may have lasting consequences on retirees' quality of life.