This article focuses on the research that the Paul Mellon Centre for Studies in British Art has conducted with users in the process of digitising its photo archive. Converting this resource from photographs mounted on card to digital assets appears, at first glance, a relatively straightforward digitisation project. However, the questions, challenges and issues raised by this project have prompted us to not only focus on the ‘how’ (the process of this conversion), but also the ‘why’. As the project has progressed, these questions about why we are digitising our photo archive and what benefit/s this will have to users and its impact on the field of British art history in the future have grown more voluble.