This paper examines the failure of international humanitarian law to sufficiently regulate the use of advanced military technologies, specifically in conflicts between sovereign and non-sovereign actors. This failure is twofold. First, the regulation of weapons consistently lags behind their development and use. Second, international humanitarian law generally excludes non-sovereign actors from its jurisdiction. Juxtaposing the 1925 Geneva Gas Protocol with the contemporaneous Moroccan Rif War reveals loopholes in international humanitarian law that enable major powers to enjoy unrestricted use of advanced military technologies toward imperial ends. This paper contends that the failure to regulate chemical warfare in the 1920s has significant parallels with the nebulous legal status of drone warfare today.