Singapore was one of the first movers in Asia to legally facilitate the recognition and use of advance directives in end-of-life decision-making. The Advance Medical Directive Act (AMDA) came into force in 1997 to emplace a legislative framework to enable individuals to exercise greater control over the medical care for their terminal illness. Notwithstanding extensive consultative and parliamentary deliberative processes, the Advance Medical Directive facility never really took hold in clinical care for the terminally ill in Singapore. Although uptake rates since 1997 have risen appreciably, rates of implementation are too low to have any measurable impact. This chapter therefore evaluates the merits and weaknesses of the Singapore AMDA framework. It then traces the evolution of anticipatory end-of-life decision-making policy from its original transactional mindset to the current, process-oriented and ‘communications’ model. The question then evaluated is whether advance directives (in statutory or other forms) have any continuing role in the current push towards more widespread advance care planning under the national ‘Living Matters’ programme spearheaded by the Singapore Agency for Integrated Care.