In November 2015, the United States and the Russian Federation convened the main international stakeholders engaged in the Syrian conflict to broker the Vienna Accords. The unfolding political process culminated in the issuing of UN Security Council Resolution 2254. Since then the situation has evolved rapidly, ushering in a new outlook for the resolution of the six-year-old civil war. The conflicting parties in Syria have not yet fathomed the momentum of this deal. Some progress has been made as part of successive attempts to establish a “cessation of hostilities,” but there have not yet been any major breakthroughs because the negotiating parties, supported by regional allies, are resisting the process every step of the way. The war has created new geographic realities: governance structures, political economies, and cultural paradigms. These geographies will not be easily bypassed. Dealing with the fragmented situation will hinder the prospects of a top-down solution, particularly because none of the negotiating parties has full control over its constituency. This article focuses on understanding this new geography. Arguing that the emergence of radicalized actors on the scene is not an accidental feature of the conflict dynamics, it shows how, instead, the territorial patterns of control by the different actors have used and exploited the territory to advance their positioning. Subsequently the article argues that these patterns, intended or not, have fostered the radicalization of the armed actors on all sides, imposing in the meantime asymmetrical patterns of territoriality that will seriously undermine the top-down approach of the Geneva process.