New media facilitates communication and creates a common, lived experience. It also carries the potential for great harm on an individual and societal scale. Posting integrates information and emotion, with study after study finding that fear and anger transfer most readily online. Isolation follows, with insular groups forming. The result is an increasing bifurcation of society. Scholars also write about rising levels of depression and suicide that stem from online dependence and replacing analogical experience with digital interaction, as well as escalating levels of anxiety that are rooted in the validation expectation of the ‘like’ function. These changes generate instability and contribute to a volatile social environment. Significant political risks also accompany this novel genre. Hostile actors can use social media platforms to deepen political schisms, to promote certain candidates, and, as demonstrated by the recent Cambridge Analytica debacle, to swing elections. Extremist groups and terrorist organisations can use online interactions to build sympathetic audiences and to recruit adherents. Since 1939, the Offences Against the State Act (OAS) has served as the primary vehicle for confronting political violence and challenges to state authority. How effective is it in light of new media? The challenges are legion. Terrorist recruitment is just the tip of the iceberg. Social networking sites allow for targeted and global fundraising, international direction and control, anonymous power structures, and access to expertise. These platforms create spaces within which extreme ideologies can prosper, targeting individuals likely to be sympathetic to the cause, 24 hours a day, seven days a week, ad infinitum. They offer an alternative reality, subject to factual manipulation and direction—a problem exacerbated by the risk of so-called deep fakes: autonomously-generated content that makes it appear that people acted, or that certain circumstances occurred, which never did. In November 2019 the Irish Government adopted a new regulation targeting social media. The measure focuses on political advertising and to ensure that voters have access to accurate information. It does not address the myriad further risks. This chapter, accordingly, focuses on ways in which the Offences Against the State Act (OAS) and related laws have historically treated free expression as a prelude to understanding how and whether the existing provisions are adequate for challenges from new media