Since their post-war inception, Sydney's metropolitan plans have tended to be overtaken by the social, economic and environmental conditions they have had to confront. The depth and scope of Sydney's recent urban transformation threatens again to overtake metropolitan planning capacity creating, in the context of competitive globalisation, a potentially significant market disadvantage for the city, not to mention poor urban development outcomes. This paper reviews Sydney's post-war metropolitan planning strategies, examining the social and economic contexts and the policy paradigms in which they have been framed, in order to draw out the lessons to be learned from their successes and failures. We argue that future success in planning urban development will rely on richly informed and fine-grained understanding of the complex spatial outcomes of Sydney's ever-deeper global integration. Only such fine-grained understanding can empower metropolitan planning to be responsive to the evolving challenges of managing development in the contemporary urban context.