Research on college admissions shows that all students tend to benefit from overmatching, but high-status students are most likely to be overmatched, and low-status students are most likely to be undermatched. This study examines whether mismatching takes place when students are sorted into classrooms in middle school. Given prior research on effectively maintained inequality, we theorize that classroom sorting acts as an opportunity for privileged parents to obtain a qualitative advantage for their children. Our research uses administrative data from Indiana and hierarchical linear models to analyze classroom mismatch in sixth through eighth grades. We find that privileged students are more likely to be overmatched in both math and English language arts (ELA) classrooms but that overmatching is beneficial in math but detrimental in ELA. This suggests that inequality can be effectively maintained only if parents have an accurate understanding of what constitutes an advantage.