While it is frequently argued that assessment sits at the heart of the learning process, in practice assessment often remains narrowly focused on qualifications and reporting achievements, driven by institutional and societal aspirations and tensions such as accountability and economic well being. Yet, the need for assessment to account for the knowledge, skills, dispositions and attitudes necessary to equip young people for a changing and increasingly digital world is also increasingly acknowledged. Based on our recent research review, this article critically examines the role of technology enhanced assessment (or TEA). We argue that while technology offers many potentially creative opportunities for innovation and for rethinking assessment purposes, there are also numerous risks and challenges. In particular we highlight ethical concerns over social exclusion and new forms of digital dividedness and the increasing risks associated with big data and the rise of learning analytics. Finally, we note that much research and innovation happens in silos, where policy, research and practice on assessment, technology enhanced assessment and ethical and political concerns are not linked up. We conclude that there needs to be a much more wide-ranging, critical and nuanced discussion in educational and policy circles so that debates about the potential of technology can be linked to improving assessment in the light of the range of social and political challenges that such progress presents. We end with some critical questions for policy, practice and research communities, which we offer as a starting point for future thinking and ways forward.