The COVID-19 pandemic has forced many educators and students to embrace a "new normal" in learning that relies on online-learning approaches to alleviate the disruptions caused by the outbreak. In this context, the use of Web-based videoconferencing supported online lessons (WVCOL) has been offered as a solution to provide a learning environment that mimics a face-to-face classroom. However, disengagement among students in such settings constitutes a major challenge for many educators. The present study offers a new contribution to the research on online remote teaching by investigating the specific factors that hinder student engagement in WVCOL. This is a multi-case in-depth study involving two postgraduate courses. Using activity theory, several tensions or contradictions emerged as factors impeding student engagement such as mismatched objects between student and teachers, limited use of online breakout rooms, limited use of webcams, limited online non-verbal cues, limited use of private online communication tool, lack of incentive for online class participation, long student online presentations, and different expectations of student and instructor online roles. We discuss six research-based recommendations on how to address these contradictions in videoconferencing-supported courses.