The aim of the study is to analyse the opportunities and challenges of emergency remote teaching based on experiences of the COVID-19 emergency. A qualitative research method was undertaken in two steps. In the first step, a thematic analysis of an online discussion forum with international experts from different sectors and countries was carried out. In the second step (an Italian case study), both the data and the statements of opinion leaders from secondary online sources, including web articles, statistical data and legislation, were analysed. The results reveal several technological, pedagogical and social challenges. The technological challenges are mainly related to the unreliability of Internet connections and many students’ lack of necessary electronic devices. The pedagogical challenges are principally associated with teachers’ and learners’ lack of digital skills, the lack of structured content versus the abundance of online resources, learners’ lack of interactivity and motivation and teachers’ lack of social and cognitive presence (the ability to construct meaning through sustained communication within a community of inquiry). The social challenges are mainly related to the lack of human interaction between teachers and students as well as among the latter, the lack of physical spaces at home to receive lessons and the lack of support of parents who are frequently working remotely in the same spaces. Based on the lessons learned from this worldwide emergency, challenges and proposals for action to face these same challenges, which should be and sometimes have been implemented, are provided.