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Why, and under what conditions, are rebel relationships prone to cycles of collaboration and conflict? Existing literature presumes rebel relationships are relatively stable. In contrast, we suggest that in an anarchic environment of multiparty civil war, less durable, more flexible relationships---where groups move back and forth between fighting and collaborative relationships; frenemies relationships---may not only be relatively common but also provide certain benefits for rebel groups on the ground. Using a novel dataset of some 28,000 hand-coded militant social media posts from the Syrian Civil War, this research conceptualizes and evaluates the circumstances that make cyclical dynamics in militant relationships likely. First, we develop and apply the concept of frenemies to militant groups. Second, we evaluate which rebel groups are most likely to participate in frenemies relationships, under what conditions frenemies relationships are likely to occur, and in rebel-rebel dyads engage in frenemies behavior and the conditions that make frenemies relationships between two groups more likely. Understanding frenemies relationships adds nuance to our understanding of the conflict environment, and improves our understanding of a factor which likely contributes conflict intensity, duration and likelihood of war recurrence.