Taking its cue from the case of India, this chapter questions the inevitability as well as the sustainability of continuous urbanisation and presents a counter paradigm, in which information communication technology and the unlimited opportunities it affords for universal education and digital marketing allied to innovations in localised renewable energies and in fields such as permaculture, will amplify options for more distributed forms of development, expand individual and community lifestyle choices, and reinforce the global to local environmental agenda. It argues that a territorially balanced approach, prioritising the multiple advantages and opportunities of rural transition including regionally diffused urban settlements compared to concentrations in mega cities, has the potential to alleviate the pressures of migration and development that threaten surviving urban heritage across the Asia-Pacific region, and should be positioned as a central platform for the management of Historic Urban Landscapes. In parallel, this chapter critiques aspects of heritage conservation orthodoxy and argues for a re-positioning of the UNESCO Historic Urban Landscape initiative to embrace an inclusive understanding of urban heritage as a prerequisite for its wider recognition and safeguarding in the region.