By studying British Indian Army [BIA] desertions during World War II, and British postwar trial responses, this paper explores the complicated dimensions of desertion and draws attention to the need for a more explicit and comprehensive approach to desertion in international humanitarian law. The paper focuses on less known British trials dealing with desertion, namely, war crimes trials conducted by the British in Singapore. It examines how these trials dealt with contested interpretations of desertion. Drawing on lessons from these trials, the paper then highlights gaps in today’s international humanitarian law framework, specifically, the need to take into account the realities of desertion, its different permutations, and the difficulties of differentiating between prisoners of war [POWs] and deserters.