© 2015, © The Author(s) 2015. In this article, I provide some reflections on critical digital health research in the context of Health’s 20th anniversary. I begin by outlining the various iterations of digital technologies that have occurred since the early 1990s – from Web 1.0 to Web 2.0 to Web 3.0. I then review the research that has been published on the topic of digital health in this journal over the past two decades and make some suggestions for the types of directions and theoretical perspectives that further sociocultural and political research could tackle. My concluding comments identify four main areas for further research: (1) devices and software, (2) data materialisations, (3) data practices and (4) data mobilities.