This chapter explores the manner in which extremist groups could use artificial intelligence (AI) in the future to promote their narratives and recruit people to their causes. It looks at four broad use cases, namely generative AI, chat bots, gaming, and predictive analytics, and analyzes how extremists could adapt their propaganda and outreach efforts to incorporate new and innovative AI-powered techniques which would revolutionize their efficacy. The chapter then analyzes the current regulatory environment with regard to online content to assess the extent to which we are prepared for the AI revolution as it pertains to political messaging and the dissemination of information online. The chapter also touches on what all of this means for our civil liberties and what they might look like in a digital era that is also experiencing decentralization and a decline in Big Tech’s monopoly. It concludes with some thoughts on what we can expect to see in the coming years and suggestions for further research.