Recent developments in educational innovation and new technologies have made tensions between old and new models of schooling more apparent, creating new demands upon teachers as agents of change. Looking back at the last 20 years, it is clear that important steps in development have tried to find a good balance between technology- and pedagogy-driven changes. In the first part of this article, we present some strategic models that summarize these developments. The second part of the article addresses new challenges on the horizon that point towards possible future developments. However, from the position of teachers in schools today, this might create an ambivalence between old and new models of teaching and learning that use new technologies. These models are discussed as ways of preparing teachers to innovate, adopt, and implement new ways of teaching and learning in the digital age.