The national purpose driving the build-up of the Singapore Armed Forces (SAF) to its third generation has been the deterrence of any potential adversary and achieving victory if war does break out. Because the mission statement above serves as a guide for SAF’s defense policy and also its transformation efforts, it is important to be clear about what this “victory” entails. The adjectives “swift and decisive” help to illuminate the nature of this victory that we seek to obtain. As Clausewitz puts it succinctly, “no one starts a war or rather no one in his senses ought to do so without first being clear in his mind what he intends to achieve by that war and how he intends to conduct it.” This quote sums up the concern of this essay, which aims to add clarity to what victory should look like, in light of recent events and the evolution of modern warfare. It is to help us be clear about the victory we want to achieve (i.e. what is winning?). The definition of the victory SAF aims to accomplish has to be re-examined within the context of today’s debate over the future of war. The texture and nature of this victory have obvious implications for our conduct of war – strategy, operations and tactics (i.e. how to win?) – and also how we tailor future transformation of the SAF to meet what this victory requires (how we prepare ourselves to win?). One of the main issues here is that as warfare evolves, our notion of victory must adapt accordingly.