Human rights, the rule of law and democracy are interlinked and mutually reinforcing. Within the framework of international human rights law, the right to freedom of expression particularly stands out, as it constitutes a pre-requisite for the fulfilment of other fundamental rights. In this regard, as ‘guardian of the rule of law’, the judiciary plays a particularly important role in guaranteeing the respect for the fundamental right to freedom of expression and its corollaries, access to information and the safety of journalists. To do so, however, judicial actors need to be well versed on freedom of expression challenges (both online and offline), and knowledgeable about the related international standards and regional jurisprudence. To share best practices and lessons learnt in this regard, this essay will be structured in two parts: first, it will discuss the crucial role of an independent judiciary in protecting the rights to freedom of expression and access to information, while falling under the obligation to act in full transparency itself. Second, it will present an in-depth analysis of the United Nations Educational, Scientific and Cultural Organization (UNESCO)’s Judges’ Initiative, presenting the concrete experience of a United Nations’ body engaging with its constituents. At the heart of this endeavor is the goal of enhancing the international human rights legal framework, by raising, in full cooperation with them, the knowledge an capacities of judicial actors from around the world on the need to protect and promote freedom of expression, access to information, and the safety of journalists to guarantee the respect for human rights, democracy, and the rule of law.