The use of videos in teaching has gained impetus in recent years, especially after the increased attention towards remote learning. Understanding students’ video-related behaviour through learning (and video) analytics can offer instructors significant potential to intervene and enhance course designs. Previous studies explored students’ video engagement to reveal learning patterns and identify at-risk students. However, the focus has been mostly placed on single contexts, and therefore, limited insights have been offered about the differences and commonalities between different learning settings. To that end, the current paper explored student video engagement in three disparate contexts. Following a case study research approach, we uncovered the commonalities and differences of video engagement in the context of SPOC, MOOC, and an undergraduate university course. The findings offer a deeper and more comprehensive understanding of students’ video-related engagement and shed light into several key aspects related to video analytics that should be considered during the design of video-based learning (e.g., learning objectives in relation to video type or context). Additionally, the three cases indicated the important role of the content type, the length, and the aim of the video on students’ engagement. Further implications of the work are also discussed in the paper.