This study takes place in the context of a federal laptop-mediated English language pre-university course in the United Arab Emirates. Despite predictions and claims from policy makers and practitioners that 1:1 classroom devices would revolutionise teaching and learning, student results remain static and student attrition remains high. Through the lens of activity theory this paper identifies ten contradictions, and their discursive manifestations, potentially causing failure and attrition. This paper contributes to the fields of technology enhanced learning, 1:1 device initiatives, English language teaching, computer assisted and mobile assisted language learning and activity theory by highlighting several problematic experiences in teachers’ practices and mapping these within the activity system context. The paper also questions the positive impact of a 1:1 laptop initiative in this particular context, with implications for future research.