OBJECTIVE 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 2 dimensions of emotional well-being-depressive symptoms 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 relatively fewer depressive symptoms among individuals who reported high levels of work stress interfering with family life in late midlife. We find suggestive evidence of a similar association with respect to positive psychological functioning after accounting for unobserved characteristics of individuals. Among individuals reporting high levels of family stress spillover into work life at late midlife, our results suggest that retirement tends to be associated with better emotional well-being among men than among women. CONCLUSIONS Retirement may come more as a relief than as 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.