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The present study investigates middle school students’ perceptions of challenge in mathematics classrooms and its effects on achievement. Nationally representative data are used to answer the question of how eighth-grade students’ perceptions of challenge about their mathematics classrooms relate to achievement while taking students’ positive attitude toward mathematics into account. Data from the 2009 NAEP Grade 8 Mathematics Assessment and items related to students’ perception of challenge about mathematics classrooms and attitudes toward mathematics from the student background questionnaire are used in this study. Findings conclude that there is a statistically significant relationship between mathematics achievement and students’ perceptions of challenge. In addition, the effect of challenge is much greater with students who have more positive attitudes toward mathematics.