This essay sets up a comparison between two types of negotiating tactics: the first, aggregating strategies, aims at merging parties into the fewest number of sides to a conflict as possible, in order to diminish the number of war-related divisions, and the second, disaggregating strategies, rests on the idea that “cross-cutting cleavages” help moderate social conflict because they run against the construction of opposed identities. Much of the literature on intrastate conflict and rebellions supports the latter approach, but little comparative analysis on the social costs and benefits of the two types has, in reality, been carried out. By drawing lessons from the insurgencies in Aceh, Bougainville and, in part, the Solomon Islands, the article takes up an opportunity-based spoilers’ framework to analyze the strategies. It concludes that neither of the two can be identified as a “best method” if measured against sustainability and social impact, nor does one of them have a stronger effect on spoilers. In either case, the study underlines, there is an intrinsic value in long-term peace processes as constituted by repeated negotiations and continuing interaction; likewise, there are webbing effects of war on peacebuilding scenarios as a process of multiplication of social cleavages occurs after conflict.