At the dawn of the 21st century the “War on Terror” ushered in an era in which some were besieged by wars and others by war-related imagery. For the fortunate who live outside of war zones, mostly in the Global North and West, the experience of war has been primarily a mediated one. With the advent of digital imagery and its many evolving and developing technological transmutations, the possibilities of reproduction, representation, manipulation, and circulation have grown exponentially in the past twenty years. Yet in the grand scheme of human communication history, the “pictorial turn” is a relatively recent phenomenon that requires further analysis. In this article, I unpack and analyze some of the key media moments from the vast visual lexicon and iconography of the “War on Terror” to reveal its scaffolding and machinations and offer counterstrategies of resistance. I argue that the “War on Terror” is the orchestrated sum of literal and figurative imagery, a coordinated public relations disinformation media campaign designed to hide real wars and their true destruction and costs.