Compared with the re-use and analysis of existing quantitative data, qualitative secondary analysis is a relatively new research methodology. As developments in the secondary analysis and re-use of qualitative data have progressed, ensuing debate about the method has highlighted both its challenges and possibilities. In reflecting on its challenges, commentators have focused in particular on the epistemological, ethical, and practical dilemmas that arise. Yet it can also be very insightful, particularly for exploring substantive topics that have received limited research attention. This case unpacks some of the challenges and affordances of conducting qualitative secondary analysis with two existing qualitative longitudinal datasets to develop an understanding of the unfolding of men’s experiences of providing care in low-income contexts over time. The “Men, Poverty and Lifetimes of Care” study seeks to address significant gaps in (a) the existing research evidence about men’s roles in providing care in contexts of poverty and disadvantage and (b) their vulnerabilities to either becoming or remaining impoverished. Because of the paucity of research evidence about this topic, the author adopted an exploratory but strategic methodology that sought to explore what insights existing sources of evidence might yield. This proved to be a uniquely challenging but fruitful approach. The case introduces this process to highlight how certainties about the very nature of qualitative research might be refined in the process of secondary analysis; how existing datasets might be productively utilized to illicit new insights about a range of substantive topics; and some of the challenges that occur when secondary analysts are confronted by large datasets.