Secure, affordable housing is strongly linked to wellbeing in older age. This paper reports on a study of childless and poor older Malaysians who are potentially a vulnerable group in relation to accumulating such housing resources for older age. Childless is defined as a person without biological, step or adopted children, and poverty is defined following the national guideline. The research explores the cumulative advantages and disadvantages over the lifecourse that may influence their routes to attaining, or failing to attain, secure and stable housing in older age. Semi-structured interviews with a purposive sample of 34 childless and poor older Malaysians in Kuala Lumpur, Malaysia, were analysed using a lifecourse perspective to identify the events/experiences that had shaped their housing arrangements in old age. Housing arrangements are hierarchical in structure and can be categorised into four types: home-ownership, public-rental, private-rental and informal housing arrangements. The capacity to afford secure housing (i.e. public rental or ownership) decreased with ill-health and reduced opportunities to work. Structural and policy factors such as eligibility for public housing had also contributed to shaping current housing arrangements. Family poverty, low levels of education and, consequently, reduced employment opportunities affected the ability to accumulate the financial resources needed to afford housing in older age. Some individual decisions and situational disadvantages also contributed to reductions in housing choice. From the social and cultural context, some participants with greater networks had more choices and advantages in the accumulation of housing resources. Initiatives to provide retirement entitlements for workers have not favoured those in low-level informal employment or have come too late to assist those who are now older people. In conclusion, more disadvantages than advantages were accumulated earlier in their life, impacting on their ability to have affordable, secure and stable housing in older age.