While regional comparison’s methodological relevance is diminishing, its significance for historical anthropology may increase if properly assessed and reconfigured. This chapter argues this point by discussing three examples from historical South Arabia. These cases highlight the significance of adequately reflecting and identifying existing notions of the “regional” in any given research context as the basic frame of reference in this version of comparison. As a crucial device from science studies and critical theory, the distinction between contexts of discovery, of justification, and of application may be useful for a reliable yet open and flexible conceptualization that includes self-reflexive as well as indigenous notions of the regional. It is also suggested that regional comparison can be improved by triangulating it with other methodological devices, ranging from network analysis to medium-range insights from general anthropology. In turn, this may advance the operational usefulness of regional comparison in historical anthropology by strengthening its potential for highlighting both regional commonalities and diversities among the phenomena under scrutiny.