Singapore’s health system has evolved from a tax-funded colonial model to a complex mixed-ownership ecosystem of public, private, and people-sector providers. This chapter traces major transitions across five phases since Singapore’s independence in 1965, culminating in Healthier SG, a national initiative aimed at integrated, preventive, and person-centered care. It explores healthcare financing, governance, community and virtual care, and the integration of social and health services. The pandemic served as a catalyst for integration, highlighting both strengths and systemic fragmentation. Challenges remain in data interoperability, financing alignment, and public engagement, but ongoing reforms offer promise for sustainable and inclusive population health.