Women’s retirement income adequacy has become an important issue in ageing societies, yet existing research often overlooks the lived experiences of those who are “asset-rich but cash-poor.” In Singapore, where retirement security is closely linked to a mandatory savings system called the Central Provident Fund (CPF) and high home ownership rates, this issue remains underexplored. This paper examines how women experience and navigate financial adequacy in retirement within this context. The study adopts a qualitative research design, using in-depth semi-structured interviews with twenty-three Singaporean women. Thematic analysis is applied to explore their retirement planning challenges, financial constraints, and retirement income adequacy outcomes. At the macro level, the findings show that despite owning a housing asset, many participants still face cash-flow constraints, leading to ongoing financial insecurity. At the meso level, these challenges are shaped by women’s life-course factors, including caregiving responsibilities, lower lifetime earnings, and interrupted CPF contributions. At the micro level, participants report coping strategies such as lifestyle downsizing, delaying retirement, or engaging in necessity-driven work. Overall, this study highlights the limitations of asset-based measures of retirement adequacy and emphasises the need for policies that better address liquidity constraints and gender inequalities. It also demonstrates the value of qualitative approaches in revealing the complex realities of retirement insecurity, offering important implications for policy and future research.