Does historic school engagement buffer the threats of disrupted schooling -- such as those associated with the widespread COVID-19-related school closures -- to school engagement equally for female and male high school students? This article responds to that pressing question. To do so, it reports a study that was conducted in 2018 and 2020 with the same sample of South African students (n = 172; 66.30% female; average age in 2020: 18.13). A moderated moderation model of the 2018 and 2020 data showed that historic levels of school engagement buffered the negative effects of disrupted schooling on subsequent school engagement (R[superscript 2] = 0.43, [beta] = -5.09, p < 0.05). This protective effect was significant for girl students at moderate and high levels of historic school engagement, but not at lower levels of historic school engagement. Disrupted schooling did not significantly affect school engagement for male students at any level of historic school engagement. In addition, student perceptions of teacher kindness were associated with higher school engagement and having experienced an adverse event at school with lower school engagement. The results point to the importance of facilitating school engagement and enabling school environments -- also when schooling is disrupted.