In recent years, the international community has worked to confront the large and growing threat of terrorism, including by introducing new counterterrorism (CT) measures and tightening existing ones. These measures take many forms, including international, regional and domestic sanctions against individuals, groups and other entities. Such efforts pursue the legitimate aims of security and international peace – things that terrorism undermines and goes against – but they have, at the same time, implicated a degree of overlap and confusion between international humanitarian law (IHL), on the one hand, and the law and policy framework underwriting CT measures and sanctions regimes, on the other, particularly as both apply to and affect principled humanitarian action. This article addresses this area of overlap and confusion. First, it examines the applicability of IHL to CT measures and operations. Next, it addresses the co-application of IHL, CT regulations and sanctions regimes, from the mindset of preserving IHL without impeding CT measures and their objectives. The article then examines the legal questions that arise when sanctions regimes and CT measures affect IHL-mandated and IHL-protected activities undertaken by impartial humanitarian organizations. Finally, the article analyzes recent developments and makes proposals aimed at preserving an effective humanitarian space in contexts where IHL, CT legal frameworks and sanctions apply simultaneously.