This paper presents illustrative findings from a one-year pilot study undertaken in the English department of a high school in Singapore that was in the first year of implementing a one-to-one wireless laptop programme. The findings show that learning was often constrained by lecture-style presentations and overt test preparation. Despite widespread access, the students rarely explored new media as alternative sources of legitimate knowledge and missed opportunities to investigate mobile technologies as sites for meaning-making and knowledge construction. The paper concludes with a call for teachers to design language learning and assessment tasks that embrace a wider set of twenty-first century skills, knowledge and dispositions. (Contains 10 tables and 1 note.)