The present study adds to the growing body of literature on women and retirement by means of a comparative analysis of the factors associated with anticipated retirement timing (among pre-retirees) and actual retirement timing (among retirees). Adopting a political economy of aging perspective, we argue that socially-structured patterns of gender inequality related to women's multiple roles across the life course affect patterns of retirement timing. Specifically, we hypothesize that the gendered nature of women's work-retirement decision-making is unanticipated during pre-retirement years. Logistic regression analyses are performed on data drawn from a sample of 275 women aged 45 and older living in the Vancouver area of British Columbia. A central finding is that while actual timing of retirement is affected by family caregiving responsibilities and by health/stress factors, pre-retirees do not perceive these to be important in their own expected retirement timing. Implications for social policy, education, and women's financial and psychological well-being in old age are elaborated.