This chapter describes how drone programs facilitate the individualization of war and intensify the pressures put on the right of self-defense. Rather than using force in self-defense against an (imminent) act, some states active in the transnational war on terror use force in self-defense against individuals based on their personal characteristics. This strategy leads to authorizing action against individuals who are not presently perpetrating, nor even clearly preparing to engage in, threatening acts. The chapter argues that these changes are not merely the result of how states decide to use force in the context of counterterrorism but also are impacted by what technology allows them to do. As such, drones facilitate and arguably intensify these phenomena of individualization and dematerialization of the use of force. Focusing on one of the justifications for this practice, namely, the right of self-defense, the chapter argues that the framework articulated by some states active in the transnational war on terror, while still highly contested on some points, offers a framework for the continuous anticipation of armed attacks by individuals who show signs of continuing armed activity. The chapter shows that under pressure by state practice and rhetoric, some limitations on using force that were initially interpreted restrictively are currently interpreted extensively. More importantly, the chapter argues that even if some limitations remain, the concessions to the extensive interpretation appear to have a direct cascade effect on the remaining conditions precisely because these limitations are interconnected. It is ultimately shown that this cascade effect is epitomized by the principle of proportionality which is not only extended but transformed to adapt to the individualization of war.