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The legitimacy of the liberal international order is facing its first meaningful challenge from within. During the Cold War, liberal norms helped bind members of the order together, in part because they highlighted the illiberal, authoritarian alternative. However, the post-Cold War integration of authoritarian states into the order and the rise of illiberal domestic political movements has led to calls for a greater focus on national prerogatives than on promoting liberal values. The key question is whether liberal states should double down on promoting an order that pursues both cooperation and liberal values or settle for a lowest-common-denominator agenda of cooperation on narrow shared interests. The current order, which is thickly institutionalized and pursues an ambitious liberal reform agenda, has served the United States and its allies well. Shared rules and institutions have enabled members to resolve information, commitment, and collective action problems. And consensus on a liberal trajectory gave the overarching project legitimacy and purpose. Given that there is no longer consensus within the order on that underlying legitimacy, the question facing liberal states is whether they should attempt to coerce compliance with liberal norms or accept a more transactional form of order. Unfortunately, scholars know little about when the international system incentivizes thick, normatively ambitious orders and when more minimalist orders would be more appropriate. I begin to fill that gap by elaborating tradeoffs orders face when choosing between thick and thin legitimacy principles. An agent-based model reveals non-intuitive incentives facing states as they construct an order, demonstrating the advantages and disadvantages of prioritizing a liberal reform agenda. Case studies provide examples of how these choices have played out in the past.