Objectives. This study investigates whether the association between retirement and emotional well-being depends on prior experience of work-family conflict. Methods. We use data from the 1993 and 2004 waves of the Wisconsin Longitudinal Study to estimate linear regression models of emotional well-being, including symptoms of depression and positive psychological functioning. We also use fixed effects models to investigate whether key findings persist after controlling for stable but unobserved characteristics of individuals. Results. Retirement is associated with a relatively greater reduction in depressive symptoms among individuals previously experiencing high levels of work stress interfering with family life. We find suggestive evidence of a similar improvement in well-being with respect to positive psychological functioning after accounting for unobserved characteristics of individuals such as personality or coping style. Among those previously exposed to high levels of family stress spilling into work at midlife, our results suggest that retirement tends to bring greater improvements in emotional well-being among men than women. Discussion. Retirement may come more as a relief than a stressor for individuals previously experiencing high levels of work demands interfering with family life. However, particularly among women, retirement may not relieve the burdens of family life stressors.