The Internet has become an essential tool for various life-related purposes, and it is an instrument necessary for the proper enjoyment of a series of rights—including the right to access knowledge and information and the right to communicate. This new paradigm also implies that all people should have access to the Internet at affordable conditions, and any restrictions should be strictly limited and proportionate. As a consequence, any regulatory and policy measures that affect the Internet and the content that flows over it should be consistent with basic rights and liberties of human beings. This Article intends to explore the challenges and opportunities for freedom of speech and human rights on the Internet. In particular, it examines how Internet content governance is posing provocative and fascinating regulatory issues directly related to the growing possibilities offered by computer-mediated communication. This debate is not simply “technical,” but also political, legal, and social since it involves sustainable and value-oriented solutions, but also—more importantly—the awareness of the human-rights dimension of Internet governance. The possible answers to these issues are at the center of the ongoing discussion concerning the regulation of digital content and communication technologies. Finally, drawing upon comparative and case-study material, this Article analyses the functional relationship between modern communication technologies, legislative reforms in the area of digital communications, and constitutional freedoms.