Despite the drawbacks and the challenges highlighted by several scholars, Information and Communication Technology (ICT), in particular the World Wide Web, has the potential to foster social inclusion of people with disabilities. The UN Convention on the Rights of Persons with Disabilities (UNCRPD), which entered into force in 2008, has illuminated the role technology can play as a tool to promote the human rights of people with disabilities, and their participation and inclusion in society. The UNCRPD has also conceptualized ICT accessibility as a precondition for the enjoyment of rights, prompting a series of reforms in domestic legal frameworks globally and in the European Union (EU). Against this background, this article aims to address the role played by the EU in fostering “digital inclusion”, and critically evaluates relevant EU policies and legal rules, locating them within the broader realm of the implementation of the UNCRPD. It pays particular attention to Directive 2016/2102 on the accessibility of the websites and mobile applications of public sector bodies, as well as on the proposal for a European Accessibility Act (EAA). It attempts to show that, while the EU has thus far played an extremely important role in fostering web accessibility, many remaining obstacles must be eradicated to fully ensure access to the web to people with disabilities. This article adopts a doctrinal legal research methodology and is primarily concerned with the analysis of relevant legal rules and related scholarship. In addition, it is informed by a socially-oriented understanding of disability and builds upon the multifaceted and multidisciplinary literature on disability and technology.