A continuing issue in metropolitan strategic plans is how much of them will be implemented. This appears to depend on how far planners are able to understand and shape the future of the city; whether appropriate planning and decision-making frameworks and mechanisms exist or can be put in place for making proposals happen; and what kind of methodology, content and process is used in preparing a plan. These themes are employed to analyse the way four of the major issues attending the future of Sydney are dealt with in the recently released metropolitan strategy ‘City of Cities’, and in subsequent statements and plans. These are economic development and its spatial representation, housing, water management and use, and transportation. The first two of these represent innovative exercises in the linking of economic activity and living with land use, density and location. The second two reflect more abstract challenges in framing proposals to acknowledge the increasing constraints of natural resources upon which the city depends. The review ends by suggesting that changes to the planning process would improve the chances of implementation, and the effectiveness of the outcomes.