This paper addresses selected meanings, and corresponding outcomes, attributed to sustainable housing developments practiced in Brazil. These were examined in the light of two major national reports dealing with environment, health and sustainability: Agenda 21, and Environmental Outlook, in Brazil, 2002. Failure has, apparently, outshined success as a matter of public interest in sustainability. Some authors have blamed power struggle for the failure of sustainable planning models. Others have made different processes of production frequent scapegoats. Both trends, however, approach the subject from the point of view of spatial order and see untidiness as the visual sign of failure of authority - either the local management’s or the designer’s. Both alternatives share a common concern – to reinstate order by changing the basis of authority. They appear to aim at social control one way or another. This paper argues that those approaches, and corresponding ‘solutions’, besides belying the participatory process they are supposed to support, also still draw, to a large extent, on the management resources of the local state, which are less and less available since deregulation has, apparently, dominated World Bank agenda for developing countries. It also argues that the intended innovations which the sustainable planning agenda defines as goals are the outcome of a process which is, more often than not, a messy business of trial and errors. Some well illustrated guidelines for sustainable design offer quick response to design issues. Those, however, cannot be generally applied. Sustainable planning and design are often addressed stripped of the institutions of management that make them viable and, apparently as a consequence, independent of the culture and political context where they must be applied. What is sustainable in one given culture may prove to be quite the opposite in another context. Sustainable planning and design exercises demand local testing and widespread information geared to enable local institutions and citizens’ active participation. Awareness of its political, social, cultural and economic implications - and impact on community identity – may come as a consequence of this process, or not, depending on the institutions involved and on the channels of communication established. An analysis of some features of these “trials and errors”, looking at spatial transformations carried on by residents, in selected housing areas, illustrates the argument. This paper finalizes both highlighting some alternative concepts of sustainable design that emerge from them and indicating further research to be done.