In this paper, we report the scientific experience of HELMeTO 2020, the second edition of the International Workshop on Higher Education Learning Methodologies and Technologies Online, held virtually in Bari (Italy) in September 2020 because of the COVID-19 pandemic. The call received 59 proposals from nine countries, 39 papers were accepted to the virtual workshop and 26 full papers were finally selected to be published in the proceedings. The workshop illustrated a fast-developing scenario in which the epidemic emergency accelerated the dissemination and consolidation of online learning in higher education. A specific focus of the workshop can be identified as students’ learning experience, with studies on tutoring and active learning approaches, personalized solutions supported by data analysis, virtual reality and an in-depth analysis of human–computer interactions.