This article examines the evolution of advance care planning (ACP) in Singapore through the development of a less formal, communications based model - the Living Matters programme - and its experience with local cultural and community responses to the process and its outcomes. Living Matters is, in practice, arguably a communitarian approach to ACP. The article then examines the challenges Living Matters poses to the overarching legal framework for ACP, and suggests improvements to the proxy decision making framework under the Mental Capacity Act, offering more flexible legal tools for ACP, and more regulatory support for the means to implement ACP outcomes effectively.