This chapter examines research and practices associated with preparing educators to teach literacy, a pivotal set of skills foundational to all learning, to students with disabilities who are diverse in their strengths, biographies, and experiences. It focuses on three components core to teachers' learning and development of skills about literacy instruction. First, the chapter considers what ... [Show full abstract] constitutes school-based literacy and the knowledge base that informs it. Second, it examines dilemmas of preparing educators across a career for the inherent uncertainties embedded in teaching literacy to diverse students in inclusive settings. Third, the chapter considers ways that educators craft practices across their careers to teach literacy to students with disabilities. It argues that identifying pivotal elements of teacher learning could provide for the development of new structures and outcomes in teacher education that link with school and educational reform.