Contemporary shifts in technology are celebrated for empowering human rights defenders and generating prosperity, but they also enable new forms of human rights violations. This article traces the evolving legal and regulatory challenges posed by drones across two distinct waves of debate. The first involved questions about the legality of weaponized drones in foreign airspaces. The second has centered on the domestication of the technology in American and European airspaces. This article argues that the legal gaps exposed in both waves are not an inevitable side effect of drone technology but are the result of key actors opportunistically using new capabilities to exploit existing rules or even to produce new ones—a process known as lawfare. This linkage between technology and lawfare is important because the drone debates encapsulate many of the core challenges surrounding emerging technologies such as algorithmic decision-making, autonomous vehicles, and big data. Lawfare over unpiloted aircraft is a prelude to the struggles ahead.