Many discussions about educational technologies reflect a belief that the right approach or use of technology which transform or revolutionalise education. This chapter explores the idea that classrooms are, in fact, very difficult to transform. After reflecting upon some key phases in the history of schools, technologies in the UK, the chapter provides an example of one way in which a particular approach to education has worked to engage with technologies to develop a positive relationship between a diverse set of children and new literacies. In discussing this case study the authors put forward the issues that need to remain at the forefront of any attempt to redesign schools to respond to unknown futures.