This study demonstrates the utility of incorporating a life course, role context approach in investigations of the ties between particular roles and psychological well-being, using the links between women's caregiving and well-being as a case in point. We draw on panel data from a random sample of 293 women interviewed in 1956 and 1986, considering both current role occupancy and the duration of caregiving as well as a number of factors that may moderate the effects of caregiving on well-being. We find, using ordinary least squares regression, that the effects of caregiving on women's emotional health are moderated by their previous psychological well-being, with caregivers with high prior well-being reporting high subsequent well-being. Other moderators are previous social integration (in the form of religiosity and multiple-role involvements) and other nonfamily roles (worker and volunteer) currently occupied. What women bring to caregiving (in terms of their previous social integration and psychological well-being) shapes its significance for their emotional health. Moreover, the duration and timing of caregiving in women's lives also relate to its effects on their well-being. These findings point to the importance of examining the impacts of particular social roles, such as caregiving, in the context of other roles and resources.