This chapter sets the stage for considering the tension between intermediary liability and fundamental rights with special emphasis on the European legal framework. Competing fundamental rights, such as freedom of expression, privacy, freedom of business, and the right to property are entangled with the intermediary liability conundrum. Policymakers are still in search of a balanced and proportional fine-tuning of online intermediaries’ regulation that might address the miscellaneous interests of all stakeholders involved, with special emphasis on users’ rights. In this context, the increasing reliance on automated enforcement technologies, which will be the topic of further review in multiple chapters throughout the Handbook, might set in motion dystopian scenarios where users’ fundamental rights are heavily undermined.