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Leaders sometimes employ insincere political rhetoric in efforts to secure legitimacy or influence. When such statements are at odds with behavior, it constitutes “organized hypocrisy.” But leaders are sometimes entrapped by their rhetoric. While past research has established that both organized hypocrisy and rhetorical entrapment occur in international politics, we do not adequately understand when hypocritical rhetoric does or does not entrap states. Drawing on rationalist scholarship on audience costs, and constructivist work on norms and legitimacy, the paper analyzes cases of entrapment and non-entrapment under organized hypocrisy, in order to generate hypotheses regarding the conditions under which hypocrisy is a viable means of managing conflicting strategic and normative pressures in international politics. The paper examines cases of insincere diplomatic proposals or commitments, including superpower Cold War nuclear disarmament proposals and Soviet entrapment in the Helsinki process.