Many contemporary armed conflicts are shaped by the reliance on airstrikes using traditional fighter planes or remotely piloted drones. As accounts of civilian casualties from airstrikes abound, the ethics and legality of individual airstrikes and broader targeting practices remain contested. Yet these concerns and debates are not new. In fact, a key attempt to regulate aerial warfare was made 100 years ago. In this article, we approach the regulation of aerial warfare through an examination of the 1923 Hague Draft Rules of Aerial Warfare and the contemporary scholarly discussion of these rules. While the Draft Rules have never been converted into a treaty, they embody logics of thinking about civilians, technologies of aerial warfare, and targeting that are still resonating in contemporary discussions of aerial warfare. This article argues for a contextualized understanding of the Draft Rules as an attempt to adapt International Humanitarian Law (IHL) to the new technological realities while maintaining distinctions between different kinds of spaces and non-combatants. We argue that the Draft Rules prefigure later debates about the legality of aerial bombing by tacitly operating with a narrow understanding of the civilian and by offering a range of excuses and justifications for bombing civilians.