In the past decade, the practice of investor–State arbitral tribunals addressing investment protection in the context of armed conflict and military occupation has expanded. This has prompted a growing interest in the relationship between international investment law and international humanitarian law (IHL), two regimes with markedly different relationships to war—IHL more pragmatic and international investment law more idealistic. This article argues that, while its lack of pragmatism might render international investment law ineffective in changing how war is conducted, it is the regime under which States are most likely to be held liable for the conduct of war. This is a result of its more robust primary obligations, more effective enforcement mechanisms and large awards of damages. Nevertheless, comparing international investment law and IHL does also reveal some similarities—the legacy, it is argued, of a time when the laws of war were more about protecting private property and neutral commerce than civilians. Putting these two regimes together in this way exposes international law's uneven distribution of protection in war.