This chapter describes the challenges of integrating new technologies with literacy education in pre-service primary teacher education in Australia. The authors describe the policy context and regulatory mechanisms controlling pre-service education, including a national set of professional standards for graduate teachers, a new national curriculum for school students, the introduction of high stakes national assessment for school students, and the looming threat of decontextualized back-to-the-basics professional entry tests for aspiring teachers. The chapter includes three case studies of the authors’ pedagogical practices that attempt to reframe conceptions of the literacy capabilities of pre-service teachers to reflect the complex and sophisticated requirements of teachers in contemporary schooling. The authors conclude the chapter with a discussion of the implications of these case studies as they illustrate the ways that pre-service teachers can be scaffolded and supported to develop creative capacity and critical awareness of the kinds of literacies required in the digital age despite restrictive regimes.