This article is a case study of how English teachers in England have coped with the paradigm shift from print to digital literacy. It reviews a large scale national initiative that was intended to upskill all teachers, considers its weak impact and explores the author's involvement in the evaluation of the project's direct value to English teachers. It explores how this latter evaluation revealed how best practice in English using ICT was developing in a variable manner. It then reports on a recent small scale research project that investigated how very good teachers have adapted ICT successfully into their teaching. It focuses on how the English teachers studied in the project are developing a powerful new pedagogy situated in the life worlds of their students and suggests that this model may be of benefit to many teachers. The issues this article reports on have resonance in all English speaking countries. This article is also a personal story of the author's close involvement with ICT and English over 20 years, and provides evidence for his conviction that digital technologies will eventually transform English teaching.