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Research on shadow education —extracurricular academic learning activities— has increased over the decades and across countries. However, the relationship between contextual effects and participation in shadow education needs to be further addressed. This study aims to identify how challenges teachers face could be related to students’ shadow education participation. Using the Trends in International Mathematics and Science Study, I seek to determine whether students’ shadow education participation patterns differ according to the challenges teachers face. Findings from a multilevel analysis show that the impact of teacher challenges in the working environment influences shadow education participation to a significant degree. These findings highlight that attention be focused towards teachers’ working conditions in order to build more equitable educational systems.