There is significant interest in the potential of digital games for Twenty first century pedagogy and curriculum in schools. However, developing an informed and granular understanding of the challenges facing 'everyday' teachers in introducing work with digital games in a range of schools, across diverse subject areas, age groups and system requirements, is not straightforward. This paper reports on the initial stages of a three-year research project investigating the introduction and use of games in a variety of contexts, and discusses some of the challenges entailed in introducing teacher participants to working with games in critical and productive ways.