Advances in military technology have led many, including the developers of such technology, to propose new regulation. International lawyers have extensively examined the adequacy of the existing law to address emerging technology, but they have devoted relatively little attention in these analyses to the prior development of the law as a result of, or despite, technological change. This essay highlights two challenges that those wishing to undertake such an exercise might encounter. The first of these is the general paucity of serious engagement with the history of international law applicable in armed conflicts and the perpetuation of a particular “origin myth” of international humanitarian law. The second challenge has to do with the controversies about the impact of technology on society in general, and the impact of military technology on warfare in particular. Nevertheless, the essay concludes by pointing towards some of the insight that might be gained from a more history-conscious analysis of the relationship between technology and law in the military context.