Various political realities influence the Israeli occupation of the West Bank and the Gaza Strip and, more generally, the vitality of the international law of occupation. The law of occupation—though ill-suited to modern international relations and ill-equipped for prolonged occupation—has been almost universally invoked as applicable to the Occupied Palestinian Territory (OPT). At the same time, international human rights law is increasingly viewed as applicable to occupation. This creates a dilemma for Israel because international humanitarian law and international human rights law contain conflicting prescriptions and policy goals with respect to the administration of occupied territory. In many instances, occupants seek United Nations Security Council action in order to reconcile this tension and to secure legal and political cover for their actions. By acting under Chapter VII of the United Nations Charter; the Security Council can create a select legal patchwork applicable to a particular occupation. This use of Chapter VII resolutions by the Security Council to create international law by fiat is an important trend in modern occupation. Yet geopolitics determines access to—and the content of—such resolutions, and the sensitive political context of the OPT currently makes this avenue unavailable to Israel. For the same reason, opponents of the Israeli occupation are unable to secure Security Council action to clarify and enforce Israeli legal obligations in the OPT. This Article considers these issues from the perspectives of both Israel and Palestinians in order to examine why the relative gain and loss in each case is not immediately clear. This Article also discusses how the legality of Israeli conduct in the OPT may be gauged in light of the conflicting international legal obligations imposed by human rights law and the law of occupation. A broader exploration of the impact of these phenomena reveals that these political realities serve to increase the influence of the Security Council while further undercutting the utility and relevance of the international law of occupation.