This open access book presents Southeast Asia as an interesting and conceptually meaningful site to interrogate the transnational paradigm. In featuring research from and across different nations in Southeast Asia, it asks in what ways Southeast Asia lends itself to nuanced applications of transnationalism, and what the wider cultural and collective implications of that might be. Instead of viewing the past and the present as oppositional concepts of time, a temporal continuum is applied to a time-space compression that is fundamental to the workings of the transnational paradigm in the region that we call Southeast Asia. The transnational paradigm, a conceptual tool encompassing various configurations of transnationalism across disciplines, becomes relevant for analysing global cultural flows, but not without due consideration of the nuances shaped by spatio-temporal trends. A paradigm shift in transnationalism from historical connections to contemporary connectivity is afforded by increased mobility and accelerated cultural flows, which have given rise to unprecedented economic productivity in the past century and digital connectivity in the new millennium – a shift that the chapters collectively explore. Relevant to advanced students and scholars across disciplines in the humanities and social sciences, focused on Southeast Asia, this book is a timely exploration that unpicks and unpacks this long-discussed aspect within Asian ‘area studies’.