The law of occupation has become the subject of great contemporary interest because of two prominent, although sui generis, situations: the long-term Israeli occupation of the Gaza Strip, the West Bank, and the Golan Heights and the “transformative” occupation of Iraq. In both situations, the occupying powers resisted the label of belligerent occupier and selectively applied the 1907 Hague Regulations and the 1949 Geneva Conventions to the territories in question. The unique circumstances of these occupations have sparked vigorous debate over the future of the law of occupation. To wit, is the widely accepted, but largely unenforced, law of occupation capable of regulating transitions between armed conflict and peace in the twenty-first century? This article examines recent developments in the notoriously open-textured law of occupation that have arisen as this law has been variously ignored, invoked, challenged, examined, and ultimately reformed through practice. In particular, it discusses the triggers for beginning and ending an occupation, including recent jurisprudence on the “effective control” test. The article examines who can be an occupier, the question of “multiple occupiers” under unified command, and the obligations of occupiers in the areas of legislation and institutional reform. The author also considers the challenges of UN involvement in transitional situations, including the applicability of the law of occupation to UN forces and the role of the Security Council in adapting the law of occupation. The author concludes with a discussion of the principle of “conservationism” and the relationship between the law of occupation and jus post bellum, in order to provide an assessment of possible “futures” of the law of occupation.