Recent research has suggested that understanding and addressing the high prevalence of sleep difficulties in older women requires going beyond a purely physiological focus to address the role of social contextual pressures and demands. We take a gendered lifecourse approach to explore how sleep difficulties have evolved and how their management might reflect the position of older women in society more broadly. We conducted in-depth interviews with 12 oldest-old (average age 86) community-dwelling women who currently experienced sleep difficulties. Five themes emerged from the analysis: significant life stages; contingent lives; daily concerns in relation to ageing; attitudes and responses of women and general practitioners; and stigma and sleeping pills, which provided a conceptual framework through which to explain the reality of sleep difficulties for these women. For all women, sleep difficulties were not related to physical aspects such as pain or discomfort, but were largely shaped by demands associated with family relationships at different times in the lifecourse. Furthermore, our findings suggest that responses by women themselves, and health professionals, reflect a sense of stigma around sleep difficulties and use of sleeping pills. More emphasis on the social contextual explanations underpinning sleep difficulties might lead to better prevention and treatment of such problems, and increase quality of life.