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Teachers’ perceptions of pressures from a myriad of sources affect their instructional decisions. Drawing from meetings with 34 middle school teachers over one year, we used a grounded theory approach to examine pressures that affected teachers’ willingness to offer challenging work to students, as well as teachers’ affect about challenge and use of strategies to challenge students. Teachers reported 19 different pressures that affected their decision to challenge students, which differed by subject area. Two groups were distinguished: teachers who were unable to resolve pressures and teachers who successfully resolved pressures. Findings suggest that teachers who reported fewer pressures from within were better able to overcome pressures and challenge their students.