The experience of life regrets can motivate individuals to change their life circumstances or contribute to declines in psychological and physical health. Theory and research suggest that either outcome may depend on the regulatory approach used to manage the experience of regret and the availability of opportunity to undo the negative consequences of the regret. When opportunity is favourable, engaging in undoing the regret is adaptive whereas disengagement maintains unsatisfactory life circumstances. In contrast, when opportunity is low, disengagement is protective whereas engagement leads to impaired health. The current research includes three studies designed to examine the role of opportunity in the regulation of life regrets. Study 1 examined the associations between regret management, everyday activities, and retirement satisfaction in a sample of recent retirees. Cross-sectional results showed that retirees who perceived favourable opportunities for addressing their life regrets and also reported high levels of engagement to undo their regrets experienced high baseline levels of activity (e.g., volunteering, traveling) and retirement satisfaction. Three-year longitudinal analyses revealed that this pattern was also associated with increases in activity engagement. In contrast, disengagement protected retirees with unfavourable opportunity from three-year declines in retirement satisfaction. These findings suggest that the outcome of regulatory approach depends upon the availability of opportunity. Study 2 examined younger and older adults assigned to one of three writing activities designed to alter how they addressed their most severe life regrets (engagement, disengagement, or control). Comparisons of three-month change in well-being determined that younger adults, a group that possesses relatively high levels of objective opportunity, experienced larger decreases in wistful emotions and larger increases in closure when assigned to engagement or control in comparison to disengagement, as well as larger decreases in regret intensity when assigned to engagement in comparison to disengagement. In contrast, older adults, a group who possesses relatively lower levels of objective opportunity, experienced larger improvement in sleep quality when assigned to disengagement than the other two conditions. These findings provide evidence that the outcome of adjusting one’s regulatory approach depends on the availability of opportunity. Study 3 examined the baseline levels of regret engagement of younger and older adults who completed writing activities designed to alter their regulatory approach (engagement or disengagement). Among younger adults, being assigned to engage in, rather than disengage from, undoing their regrets produced larger decreases in regret intensity, hot emotions, and despair emotions and larger increases in closure, but only for younger adults who had low baseline levels of engagement. In contrast, among older adults, being assigned to disengage from, rather than engage in, undoing their regrets produced larger decreases in regret intensity, hot emotions, and despair emotions and larger increases in regret closure and sleep quality, but only for older adults initially disengaged from their regrets. These findings suggest that the adaptiveness of a regulatory approach not only depends on the availability of opportunity, but also the individual’s initial levels of engagement. Overall, these findings contribute to the understanding of successful regret regulation as well as the management of developmental goals across the lifespan. The results are discussed in relation to contributions to theory, clinical implications, and areas for future research.