More than 20 years ago, Wood et al. (Curr Anthropol 33:343-370, 1992) published ''The Osteological Paradox: Problems of Inferring Prehistoric Health from Skeletal Samples,'' in which they challenged bioarchaeologists to consider the effects of heterogeneous frailty and selective mortality on health inferences in past populations. Here, we review the paper's impact on bioarchaeology and paleopathology, focusing on recent advancements in studies of ancient health. We find the paper is often cited but infrequently engaged in a meaningful way. Despite an initial decade of limited progress, numerous researchers are now addressing components of the Paradox in more informed ways. We identify four areas of fruitful research: (1) intrasite, contextual perspectives, (2) subadults, (3) associating stress markers with demographic phenomena, and (4) skeletal lesion-formation processes. Although often seen as a problematic assumption, understanding the sources of heterogeneous frailty within human populations is a worthy research question in and of itself, and one that clearly links past and present health research within a global framework.