While information technologies we employ in business, government, and society have dramatically enhanced our ability to conduct commerce, the vulnerabilities of these systems create potential dangers not often fully apprehended. As an example, criminal and terrorist groups have demonstrated a sophisticated understanding of how to adapt organizational forms and information technologies to advance their agendas, regardless of how contemptible these may be. In this article, we consider how these groups may view information technology and systems both as means by which they may more effectively organize themselves and as potential targets as they subvert the underlying societal assumptions regarding the technology itself. Topics such as these have implications for both IS research and practice because the changing nature of warfare means entities that may have until recently been seen as “non-combatant” are no longer viewed as such; any organization’s online resources may be regarded and serviced as legitimate targets. This fact, coupled with the interconnectedness of the global economy, makes it imperative to understand the potential threat—whether this is acted on by criminals, terrorists, or even by hostile nation states—and place greater emphasis on defending vital systems against such attacks.