Since its founding and throughout all its developmental stages, the Movimento Cinque Stelle (M5S) has been characterised, among Italian parties, by its reliance on the Web as a tool for organisation, decision-making, communication, and identity-building. In this chapter, we analyse three dimensions of the Web’s role for the M5S against the backdrop of international theoretical debates and empirical research on digital politics. First, we discuss the narratives that Beppe Grillo and his chief consultant, Gianroberto Casaleggio, have employed to talk about the democratic role of the Internet against some real-world examples of whether and how the M5S upholds democratic principles in its operations. Secondly, we investigate how the Web was employed to select candidates for the 2013 general elections. Thirdly, we assess how M5S voters use the Internet to inform themselves about and participate in politics. Our purpose, therefore, is to conduct empirical scrutiny on how the M5S has used the Internet as a rhetorical device, as an organisational platform, and as a tool for campaign communication and engagement.