The ageing population is posing new challenges to Singapore's healthcare system. The rise of dual income and the decline of extended families, as well as an increase in age-related degenerative disorders due to increased longevity render it difficult for the family to remain the primary social safety net to care for our elderly in their own homes. Consequently, nursing homes may become increasingly relevant for resource and expertise-challenged families to cope with the burden of caring for a frail and dependent elderly. However, as the recent Nightingale Nursing Home elderly mistreatment incident attests, the standards of some have been found wanting. This paper will trace the history of nursing homes in Singapore and the evolution of government policies towards them, discuss the challenges and trade-offs of nursing home regulation, and provide suggestions for better care and governance.