Youth readers navigate complex school contexts involving not only different classes, teachers, and texts but also various institutional processes, such as tracking and reading assessment. Yet little research has examined how or why adolescents' literacy skills vary as youths interact with these myriad contexts across space and time. During this year-long study, I shadowed eight ninth graders identified as struggling readers across content classes. Data sources included 425 hours of observations, 64 interviews, assessments, and school records and artifacts. Analysis showed that participants' interactions with interrelated institutional contexts for reading intervention and school discipline tended to position students as deficient readers and deviant youths regardless, sometimes, of engaged, skillful reading. Findings have implications for the reconstruction of secondary literacy contexts.