This paper describes a journey undertaken by literacy tutors who were caught between incompatible values and needs in building apprentices' literacy. The highly literate tutors were committed to teaching critical literacy. They believed that improved literacy could support learners' aspirations to advance their prospects at work, build their connections within their community and improve their health. Hence, the tutors aimed to guide their learners into membership of an imagined community of fluent readers. They found, however, that the apprentices, along with their managers and training coordinators, saw literacy as instrumental rather than a desired outcome in its own right. Essentially, achieving a sufficient level of literacy was needed for the apprentices to become members of workplace communities of practice. Tutors then questioned their prior assumptions about the intrinsic importance of literacy, slowly accepting a dichotomous way of thinking where industrial ways of learning and knowing were predominant. Tutors' realisation that apprentices already possessed embodied and oral literacies helped them to support the apprentices in escaping (though not leaving) workplace contexts that were becoming increasingly document-driven in character and featuring rising expectations of improved print literacy.