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This article examines questions relating to the appropriate role of digital intermediaries in regulating online terrorist-related content and the extent to which proponents of human rights should be concerned with the free speech implications of intermediary liability, through a comparative analysis of recent developments in Europe and the United States. While Europe is contemplating introducing compulsory frameworks to regulate intermediaries, the United States is continuing to apply existing frameworks that incorporate traditional notions of harm and causation and immunise intermediaries for the expression of third party users. Ultimately, this examination leads to the conclusion that compulsory regulation of intermediaries for online terrorist related speech creates significant dangers to the exercise of free speech, the effects of which ripple far beyond the terrestrial borders of those jurisdictions engaging in such regulation.