Static reading labels are problematic not only because youths demonstrate varying reading skills and identities across secondary classrooms but also because being labeled as "struggling" can undermine literacy learning. Little research has investigated how "struggling" and "proficient" readers' interactions with shared classroom contexts may mediate their literacy in similar and different ways. In a school-year-long qualitative study, the first author shadowed eight struggling readers across classes in an urban high school and compared their literacy experiences with those of youths not labeled as such. Analysis of 46 interviews, using 425 hr of observations as contextualizing data, showed that interactions with school contexts contributed to students' positioning as struggling or proficient regardless, sometimes, of skilled reading. Proficient readers reported feeling that their perspectives were valued whereas struggling readers reported theirs were not. By documenting how contexts mediated youths' perspectives on reading, findings have implications for disrupting deficit labels and promoting socially just teaching.