For many teachers of middle school and high school, the greatest challenge they face in trying to help struggling readers improve their skills can be students' self-perception. When young people do not see themselves as members of the "literacy club," it is not just a simple matter of persuading them that becoming a fluent reader is worth the effort. Some students take a deliberate and public stance distancing themselves from the culture and all of the behaviors associated with school, from carrying books to doing homework to participating in class discussions. Convincing such students that they can do well in school without losing their identities requires patience and understanding, and an ability to build relationships in which students feel understood and cared for. In this article, the author presents an account of what it can look like when a teacher has the skill and the passion to be able to establish such an atmosphere. This article describes an ethnographic study of a ninth-grade literacy classroom in Urban High School, a vocational or Career and Technical Education (CTE) school located in the South Bronx in New York City. While the school's Automotive and Building Trades departments are successful by many standards, providing impressive professional internships in the automotive and building trades for many seniors who do well in both their shop and their academic classes, a significant number of students fail the English Language Arts Regents Exam and fail to meet graduation requirements. For most students at Urban, learning the trades that are taught there holds the potential for significant socioeconomic advancement; failure to pass academic literacy benchmarks can hold them back from advancing in or even from entering shop classes. Ironically, students who might come to reading and writing "through the channel" of a hands-on skill are held back from the opportunities to do so if they do not first master their academic class work.