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Under what conditions do leaders of democratic states delegate policymaking responsibilities to the military? Existing research provides insights into particular cases but lacks systematic analysis of factors contributing to civilian delegation of policymaking to the military in foreign policy and security decision making. Meanwhile, delegating policymaking functions to the members of the military profession can have severe implications for civilian control, foreign policy, and national and international security. To shed light on this understudied phenomenon, I conceptualize erosion of civilian control by delegation and advance four testable hypotheses about the conditions under which it may occur. To test these hypotheses, I examine the evidence from civil-military dynamics in post-Cold war policymaking in the United States (1991 - 2018). I rely on process tracing to test the new hypotheses against the alternatives in each given case of policy formulation. Then, I apply set-theoretic analysis to compare cases and identify the hypothesized conditions as necessary, sufficient or being constitutive parts of more complex causal mechanisms. This research will contribute to the discussion of civil-military relations, democratic governance, and security studies.