At the beginning of the 21st century, we co-edited a book called Technology and In/equality, Questioning the information Society. In that book, we focused on access and control of media technology, education and skills with a particular focus on gender and global economic development. The editors and contributors were all committed to approaching teaching and research about digital technologies and society from an interdisciplinary perspective. In this article, we reflect on how the debates about digital inequalities have developed over the past 20 years, and on our current understanding of “technology” and “in/equality,” the key terms in the title of the book. In this article, we examine what has stayed the same and what has changed, through the lens of gender. We argue that while digital technologies have clearly changed, inequalities have persisted. Contrary to popular belief, access is still an issue for the global south, as well as for marginalised communities throughout the world. We also show how gender inequalities and hierarchies are reproduced in digital spaces, demonstrating that even where women have equal access, possibilities for discrimination and oppression remain. We conclude by arguing that there remain important tasks for scholars of technology and new media, namely to monitor the material and symbolic significance of new technological developments as they emerge and to examine the ways in which they may reflect and re-produce social inequalities.