Qualitative research suggests that women living in public housing recognise the potential benefits of paid work including having more money, developing skills and improving self-esteem, but face significant practical barriers to getting and sustaining paid work. These include poor or uncertain health, caring responsibilities for children and the transport and other difficulties associated with living in some places. Importantly, taking up paid work is not just a question of money, but women weigh up the effects more broadly on family health and wellbeing (Hulse and Saugeres 2007). A similar range of factors was identified in similar qualitative research in the UK (Fletcher et al. 2008). Little is known about why, and how, a quarter of female public housing tenants do engage in paid work despite these barriers. This paper reports on one study that investigated this issue using a longitudinal research design. Whether and how women living in public housing can move into paid work, and the effects of this on them and their families, may seem at face value a very specific issue. However, as we shall see in the next section, investigating this issue both draws on, and contributes to, rich veins of research about issues that are at the centre of modern life: experiences of paid work, the logistics of managing work and caring, work and dealing with a disability or a health problem, and cultural beliefs about work and mothering that pose challenges for both welfare reform and social inclusion strategies. The paper proceeds as follows. First, we provide a conceptual framework drawing on three disparate strands in the literature: on public housing and employment; gender and the labour market; and cultural attitudes about working and caring. Second, we outline the research design and methods for longitudinal study of female public housing tenants in paid work at the outset of the study. Third, we present some findings on outcomes for women who did reenter paid work and the ways in which they were able to face, and in some cases manage, persisting obstacles and constraints. We conclude by examining some implications for our understanding of the role of work in addressing poverty and disadvantage.