This paper provides an overview of the evolution of the concept of jihadism as it presently exists in cyberspace. From its roots during the Chechen conflict to the current use of social media by the Islamic State (IS), this paper identifies and examines three highly significant paradigm shifts: (1) the emergence of rudimentary Web 2.0 platforms and jihadist forums; (2) the advent of advanced Web 2.0 and social media platforms as methods of spreading jihadism; and (3) turn towards ‘lone wolf’ terrorism. In this paper, the author argues that IS’ extensive reliance on unaffiliated sympathizers, who either re-tweet or re-post content produced and authorized by the IS leadership can be seen as a groundbreaking paradigm shift in the evolution of jihadism in cyberspace. Furthermore, it is also argued that IS’ strategy of empowering of unaffiliated sympathizers represents a further development in the evolution of jihadism in cyberspace and can best be understood as an attempt to normalize and legitimize IS’ existence through its efforts to dominate the ‘IS narrative’ across social media platforms.