The Middle East and North Africa (MENA) region is often thought of as exceptional from the perspective of international law: with low participation in the core multilateral agreements that make up the fabric of the international legal order, no regional institution comparable to those in Europe, the Americas and Africa and limited penetration of international environmental and labor protections. Yet in truth the MENA has been profoundly marked by international law and is increasingly significant in reshaping the core attributes of the international legal order. In particular, in the post-Cold War era, the region has become a laboratory for new international law paradigms. Punitive multilateral sanctions regimes, imposed for arms control purposes, have generated a virtual modern-day siege system. Militarized conceptions of human rights have been applied to the region in ways that loosen the legal norm of non-intervention at the core of the United Nations sovereignty order. Unilateral strikes against non-state actors in the territory of MENA countries have given rise to novel rules of engagement under the laws of armed conflict. The remaking of the law of the international security order in the post-Cold War and post-September 11th eras has taken place largely through experimentation in the Middle East. In this paper, I examine three episodes—the 2003 Iraq war; the 2011 Libya intervention; and air strikes in Syria beginning in 2014 against the Islamic State—to explore the degree to which the region has come to serve as a zone of international legal innovation and exception. In the process, I examine the ways in which international law has structured processes of intervention that are shaping a "new" Middle East even as the encounter with the Middle East is also reshaping the character of the international security order.