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International actors engage rebel groups in conflict zones for better humanitarian outcomes. What are the political conditions under which such external engagement occurs in internal conflict zones? We argue that “insecure governments” and politically “modulated rebels” are the key factors that explain the international humanitarian engagement with rebels in civil conflicts. With the history of instability marred by coups and frequently changing hands of governments, insecure governments resort to international help and allow international actors to interact with their internal enemies. In contrast, with strong political control and military capacity, secure governments play a gatekeeper role, dealing with internal enemies autonomously. On the rebel side, politically “modulated rebels” are the prime candidates for international humanitarian engagement. Such modulation is likely to occur after civilian-connecting experiences over time by holding territory or after peace talks. We test these arguments using the case of the United Nations (UN) action plans between 2000 and 2015, in which some rebel groups committed to reducing the practice of child soldiering. We find that the combination of “insecure governments” and “modulated rebels” can systematically account for the UN action plans occurrence. Our analysis has implications for the role of external actors in internal conflict zones around the world.