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This study focuses on understanding the factors associated with student well-being during the COVID-19 pandemic. Although predictors of school connectedness are well documented, few studies examined attitudinal factors as predictors in a pandemic context. The present study aims to investigate how secondary school students’ demographic characteristics, academic achievement, and attitudes toward learning are associated with their sense of school connectedness during the COVID-19 pandemic. Data were collected from 11,640 students in Spring 2021 through a large-scale literacy assessment and questionnaire in Ontario, Canada. The results from factor analysis and multiple regression indicate that engagement with online learning was by far the strongest predictor of students’ sense of school connectedness. Practical implications of the findings are discussed.