Social role researchers are increasingly going beyond simply asking whether role occupancy is associated with health status to clarifying the context in which particular social role-health relationships emerge. Building on this perspective, the present study investigates the relationship between social role occupancy and health status over time in a sample of employed Canadian men and women who vary by family role occupancy, life stage, and income adequacy. Results indicated that compared to triple role women (defined as those who are married, have children living at home and are in the workforce), single and double role occupants in 1994/95 were significantly more likely to report poorer self-rated health and the presence of a chronic health condition in 1996/97. This relationship held true for women in varying life stage and economic circumstances. While family role occupancies were not as strongly related to the health status of men as women, one exception emerged: for older men, single and double role occupants reported significantly poorer self-rated health status than triple role men. Methodological limitations of the study are discussed, and the need for added specificity in the study of social roles and health status emphasized.