Singapore is an ageing nation. Four key aspects of health and ageing are worth examining: The built environment, healthcare financing, long-term care facilities, and intergenerational support. Elderly Singaporeans may be fortunate to live in a well-connected ecosystem with the necessary facilities, but there are challenges in ensuring that they can consistently afford their needed healthcare. Furthermore, it is increasingly difficult to rely on loved ones for support. This brief report also questions the limits of individual responsibility and family-community support, the two key principles which underpin Singapore’s approach towards ageing.