The rise in the use of the term ‘digital leisure cultures’ has gained prominence in academic circles over the past few years (Spracklen, 2015). The idea for this book arose out of a specially convened digital cultures stream and subsequent discussions that took place at the Leisure Studies Conference at the University of the West of Scotland in 2014. Since then a number of articles, events and scholarly debates have focused on the digital turn in the study of leisure (here we include sport, events, festivity, tourism and recreation). We want to contribute to the emergent critical research agenda on digital leisure cultures, drawing upon theoretically informed analyses that consider social forces, power relations, socio-spatial inequalities, marginalisations, exclusions, contradictions, crisis tendencies and lines of potential or actual conflict. In this introductory chapter, we reduce these complexities to a focus on the transformations and tribulations associated with the digital turn upon the leisure sphere before illustrating how the selection of chapters contributes to these important debates.