An investigation of planning obligations is used to explore the political and economic dynamics associated with the interaction between the planning and development processes. A significant widening in the use and scope of planning obligations has occurred in the last ten years. Obligations are used not only to remove physical constraints on development and to mitigate direct development impacts, but also to ameliorate more diffuse social, economic, and environmental impacts, to provide community benefits, and to support wider policy objectives. This broadening of practice has been spurred on by the austere financial environment within which local authorities must operate. Planning obligations have provided a mechanism for shifting part of the immediate financial burden of the provision of off-site infrastructure, facilities, and services from government to building producers and consumers. This poses a dilemma for planning practice. On the one hand, the profile of planners is raised because they are key negotiators in delivering improvements in local infrastructure and services. On the other hand, the financial aspects of development proposals now influence planning decisions. The potential to negotiate planning obligations is influencing land-use patterns, spatially, sectorally, and in terms of local built form. Short-term planning gains are tending to override longer term planning concerns such as environmental quality. These trends challenge fundamentally our conception of the nature of planning.