Teaching training can lag changes in school and society. With the onset of ubiquitous writing and mobile devices, the literacies experiences of today’s school and teacher students are different to those of most teacher trainers. In this chapter, a sequence of case studies is presented linking the school student, the teacher education student, and the teacher educator to provide a multifaceted picture of literacies development. Two questionnaires answered by 71 and 39 upper secondary school students, respectively, provided a picture of literacies use in upper secondary school (Case Study 1). The written tasks and the post-writing interviews with three upper secondary school students highlighted the tensions between out-of-school ubiquitous literacies and the in-school academic writing demands (Case Study 2). The teacher education student participatory research case study with four students challenged perceptions of how teacher education students learn academic literacies, and of student resilience (Case Study 3). Together, the case studies showed a disconnection in school between school student contemporary ubiquitous literacies and school literacies expectations. Although finding ways to ameliorate this disconnection through innovative teacher education is important, finding ways to simultaneously strengthen student teachers’ learning autonomy, strengthen the sustainability of their teaching to keep abreast of ubiquitous literacies changes is central to make school inclusive and sustainable.