The complexity of planning and implementing peacebuilding processes has been discussed using various approaches, for example, adaptive peacebuilding, and the “local turn” in peacebuilding. These theories argue that peacebuilding is a nonlinear and contextual process, contrary to the linear, static conception of the liberal peace paradigm. This paper contributes to this field and seeks to learn how peacebuilding processes can be planned better, by integrating the concepts of adaptive and urban peacebuilding. Using action research and organizational ethnographic analysis of an EU-funded peacebuilding process between Palestinians and Israelis in Jerusalem, this article lays out four general steps to improve planning for future peacebuilding initiatives: (1) integrate flexibility; (2) balance inherent asymmetries; (3) “localize” planning; and (4) plan for indirect alternatives. In conclusion, we discuss the implications for peacebuilding processes in other contested and settler-colonial cities.