Scholarship identified the present and future of war as increasingly characterized by urbanization and political-economic actors that Western international assistance defines as ‘illicit’, ‘illiberal’ or ‘criminal’. This article asks how Western international assistance could and should shape war-to-peace transitions for contributing to the emergence of lasting non-violent ‘peaces’. It combines scholarly insights from ‘pragmatic peacebuilding’ scholarship and practice with interviews and grey literature on masterplanning projects in two neighborhoods in Damascus, Syria, that are prepared for ‘reconstruction’ or ‘redevelopment’, namely Qaboun and Basateen al-Razi. Thereby, it, on the one hand, challenges current approaches that, as in the ca...