With the digitalisation of education increasing, the relationship between student engagement in Technology-enhanced Learning (TEL) and digital skills has remained largely unexplored. There is a strong consensus that engagement is necessary for students to succeed in school. We hypothesised that students reporting high and low levels of general engagement display differences in terms of their engagement in TEL, and that students’ digital skills correlate with their engagement in and disengagement in TEL, which in turn is related to their learning outcomes. We used statistical tests to explore the relationship between the students’ (N = 410) general engagement and engagement in TEL, and investigated how digital skills were related to engagement and disengagement in TEL. We found significant correlations between students’ digital skills and engagement in TEL, showing that the possession of high levels of digital skill is related to engagement in TEL. Interestingly, digital skills were not related to disengagement. This suggests that students reporting both high and low levels of digital skills disengage to some extent when learning with technologies. We also identified variables reflecting both engagement and disengagement in TEL that predict student performance as measured via final grades, implying that in order to understand and support students who learn with technologies, a broader understanding of the factors influencing engagement and disengagement is key.