Abstract: In December 2006 local residents celebrated the withdrawal of a planning application for a cement terminal at White Bay, Sydney. While this action highlights the value of political organising in a marginal seat in the lead-up to a state election, it also raises important planning issues about the redevelopment of old waterfront sites, or what Hoyle (1988) identified as part of the port-city interface. What happens to city ports when many uses move to new seaport facilities, and there is increased competition for urban amenity and spatial control of both water and land at the former city port site? As Gilliland (2004, 453) noted, “… one effect of incessant technological innovation is to periodically destroy past investments and radically transform the urban landscape”. Transformation is, however, increasingly contested. Importantly, as seen at White Bay, it is contested through the notion of place, not simply seeing the port as a conduit in space. Given this contestation, what constitutes good urban planning at the port-city interface? In this paper, it is argued that the recognition of changing urban contexts, awareness of environmental issues, fair processes and a comprehensive redevelopment plan are essential to garner community support and to avoid piecemeal redevelopment.