Is Hacktivism a protected form of free expression or a threat to democracy? While Hacktivism is liable to prosecution regardless of its political motivation, it also qualifies as direct action in digital political protest, intended to trigger political change. This book explores this apparent contradiction by proposing a new approach to assess the proportionality of interference with digital political protest. Drawing on case law of the European Court of Human Rights (ECtHR) and specific democratic theories, the analysis considers the role of information and communication technologies (ICTs), the liberal rule of law, and radical democratic ideas. Provided that Hacktivism neither undermines democracy nor advocates for violence, it can safeguard free political debate. The study argues that Hacktivism, aligned with the ECtHR’s interpretation of the European Convention on Human Rights as a living instrument, should be recognized as a legitimate political activity essential to democratic development. By addressing the evolution from legally ambiguous actions to accepted forms of protest, this work contributes to the broader understanding of Hacktivism’s role in modern democracies.