Presenteeism refers to working despite ill health that might otherwise warrant sickness absence. Estimated to cost tens of millions of dollars in lost productivity, the concept has attracted the attention of different academic disciplines, policymakers, and practitioners interested in mitigating the problem. Although a topic of significant interest, the current understanding of presenteeism is compromised by a number of conceptual and methodological factors that follow from one another. We begin this introductory article by providing a brief overview on three specific challenges, namely, (1) presenteeism ill-defined as a unitary construct, (2) narrowness of approaches to measure and study presenteeism, and (3) insufficient research on the social and relational dynamism that characterizes presenteeism. We then provide an overview of the eight articles that comprise this issue and analyze how they address the aforementioned three challenges by adopting alternative theoretical frameworks, utilizing new measurement approaches, and/or by shedding light on the dynamic nature of presenteeism. Finally, we discuss fresh perspectives and promising directions for future research endeavors on this topic, with the hope that this issue will inspire further research on the practical implications of presenteeism for promoting positive health and well-being at the workplace.