Ongoing societal datafication and, most recently, the widely noticed launch of ChatGPT, continue to raise the “user question”: what role(s) does the user play in datafied, artificial, and automated environments? Recent technological advancements have begun to challenge fundamental assumptions in media and communication theory and, thus, urge scholars to (re-)visit and (re-)examine the interrelations, dynamics, and entanglements of (human) users with datafied environments. Two rapidly expanding but still largely distinct bodies of research are addressing these topics: critical data and platform studies, primarily focusing on structural approaches, and user-centered perspectives anchored in the tradition of audience research. Situated at the intersection of studying platform power and user agency, the aim of this special issue is to connect structural approaches with studies of lived user experiences through the lenses of reflectivity and reflexivity. We believe that linking platform and data perspectives dealing with questions of power, accountability, and governance on a societal level to users’ engagement with digital technologies and automated systems in an everyday context is a fruitful path when aiming for a comprehensive understanding of the societal implications of the widespread adoption and integration of digital platforms and intelligent technologies. The concepts of reflectivity and reflexivity provide a valuable conceptual starting point for a more integrated and holistic discussion of the complex user-data relations emerging in and from datafied environments. While the individual contributions in this special issue present their own take on the proposed concepts, the purpose of this introduction is to establish a broader theoretical foundation by outlining some overarching considerations on how these concepts can be understood and integrated.