This chapter will examine the role of the Internet and associated technology such as the Internet of Things (IoT) and cloud computing (CC) in the process of radicalisation to terrorism and violent extremism. Particular emphasis will be placed upon the role of online environments in facilitating communication and the spread of extremist ideology, as opposed to operational and strategic recruiting functions of the Internet. Before assessing the debate, this chapter shall define two key concepts, radicalisation and violent extremism. Firstly, the chapter will provide an assessment of academic literature that has perpetuated a false offline and online dichotomy. Then, the chapter will demonstrate the new communicative role of technology within violent extremist movements since the emergence of Web 2.0. Following this, Sageman’s (Leaderless Jihad: Terror networks in the twenty-first century, University of Pennsylvania Press, 2008) ‘bunch of guys’ bottom-up framework will be employed to understand how the process of radicalisation can be facilitated and amplified by the digital age, referring to the concepts of moral outrage, othering, virtual communities and echo chambers. Lastly, contemporary literature that considers the interplay between online and offline domains will be explored.