Over the last decade, the Middle East has been amid unprecedented changes, with the Arab Uprisings, its subsequent turbulent developments, ongoing conflicts, and intense sectarian animosity being stark reminders of the region’s reality. In addition to these, other forces are at work; a globally integrated youth culture, increasing economic development, and thriving media production and consumption markets are facilitating the gradual advent of the digital era in the region. This paper maps out various changes, developments, and trends in how the Middle East adapts to the digital turn. It delves into the intricacies of the region’s digital turn—a stage informally linked with the convergence of media, telecommunications, and computers that has been accelerated over the last decade. It examines how information technologies affect the region and how the digital turn has reconfigured the Middle East. It also examines the implications of society, at the intersection of tradition and modernity, navigating these changes and whether information technologies promote inclusive practices and carve new spaces while engendering new forms of exclusion. The paper takes an inward-looking and outward-looking perspective to unravel the complexities of the digital Middle East. The inward-looking perspective revisits and reconsiders the question of “change” and “stasis” in the region, redirecting the focus from the affordances of new technologies to the productive tensions, shifting dynamics, and uneven developments engendered by the adoption of information technologies. On the other hand, the outward-looking perspective brings to light the global south dimensions of the digital turn by placing it in the broader context of the global information revolution. Supported by a rich collection of original case studies and data figures, the paper draws on infrastructure studies, communication studies, and sociologies of the Middle East to provide an analytical account of regional digital practices. It explores the interplay between processes of social change and technological transformations, particularly the intersections, interrelations, and overlaps between information technologies and various societal practices and dynamics. With illustrative case studies and grounded theory, the paper reflects on the extent to which the digital Middle East is integrated into global digital cultures and how it has maintained specific distinctive markers. It underscores the need to investigate the digital Middle East with an eye on particular transformations, transitions, disjunctions, and disruptions that animate a far more complex reality than previously considered.