Singapore’s healthcare system ranks among the best in the world in terms of infant mortality rate, longevity, disability adjusted years, and so on. What is most remarkable, however, is that it achieved these fine outcomes at less than half the costs in comparable countries. The achievement of high healthcare outcomes at low costs is what constitutes ‘success’ in the case of Singapore. While the factors underlying the success are wide-ranging, a lot of the credit must be attributed to the government’s policy. In this chapter, the evolution of the policy measures since Independence will be tracked, along with their impact on improving healthcare services while containing costs. The measures have evolved with epidemiological and technological shifts as well as the rising expectations of a more prosperous and contestable society. The future continuation of the salutary trajectory will depend on the technical merits of the policy measures in the face of changing circumstances as much as their political legitimacy.