We generate and test a moderated mediation model of the effects of two retirement-related stressors (namely, financial and marital) on the severity of alcohol misuse among retirees. We posit that in addition to using alcohol to cope with stressors in retirement, alcohol may also be used to self-medicate the secondary, sleep-related effects of such stressors, and that gender serves as a key boundary condition, moderating the impact of such stressors on sleep-related problems, and of sleep-related problems on alcohol misuse. Using longitudinal data collected from a sample of 292 retirees, our findings generally support this model, suggesting that both stressors are associated with the severity of alcohol misuse among male retirees. Moreover, our findings demonstrate that – for male retirees – the effect of both stressors on the severity of alcohol misuse is to a large extent secondary to the stressors themselves, mediated by the sleep-related problems they may generate.