What kind of order and contestation dynamics emerge if the initial institutional bargain includes liberal, partially liberal, and nonliberal visions of order? This contribution to the special issue locates the liberal ideational and institutional properties within the crisis management domain and analyzes contestation dynamics and their impact. My argument is twofold. First, liberal visions of order (e.g., based on human rights and self-determination) have coexisted alongside other aspirations focusing on the right of nonintervention and privileged political communities because post–World War II conflict management is rooted in the legal ambiguity of the Charter of the United Nations (UN). This ambiguity (low legalized institutionalization) gives space to different interpretations of what counts as peace, enforcement, threat, and the relationship between the UN and regional organizations (low liberal embeddedness). Second, ambiguity and competing visions of order sustain persistent contestation, which produces dialectical ordering within and outside the UN. Within dialectical ordering, order-challenging contestation occurs when actors disengage from the global level or when their vision of order becomes globally hegemonic. While order-challenging attempts in the realm of crisis management exist, they have remained unsuccessful so far. Seen from this perspective, there has never been a liberal international order in conflict management—only liberal attempts to impose a liberal order on an ongoing dialectical order-making process. So far, other order-challenging attempts, such as Russia’s sphere of influence or China’s developmental peace approaches, have also remained unsuccessful. Contestation remains the norm.