This paper will survey IS’ social media strategy to explore the role and impact of unaffiliated sympathizers in the Western world. Specifically, it will focus on how these supporters further disseminate IS’ messages, and what strategic function they fulfill. In order to provide an analysis of this highly dynamic phenomenon, this research provides an overview of the evolution of the jihadist in cyberspace. The following section provides a discussion of how IS leverages the power of social media, focusing on how the activities of unaffiliated sympathizers create an echo-chamber which allows for IS’ messages to dominate the so-called ‘Twittersphere,’ as these messages are repeated, thus becoming somewhat normalized. This soft-power strategy, in contrast to its military campaign, can be understood as an attempt to normalize and legitimize IS’ existence. Finally, this paper concludes by offering thoughts on how IS strategy can be undermined through grassroots campaigns of counter-messaging.