This paper provides a new, interpretive gazetteer and chronology of Hadramawt’s highland monuments based on results from archaeological survey and test excavations by the RASA-AHSD (Roots of Agriculture in southern Arabia-Arabian Human Social Dynamics) Project. With the exception of a few incidental sightings and an unpublished pipeline survey, the prehistoric record of southern Yemen’s highland plateau has been largely unknown. There are few settlements, so that understanding human landscape history must begin with the numerous small-scale stone monuments left by mobile people. With examples representing monuments from the fifth, fourth, third and first millennia BC, the corpus of small excavations and radiocarbon dates reported here provides the first guide to the monument types of South Arabian highlands. Monument building began under more moist conditions and appears to have commemorated animal sacrifices long before commemorating mortuary rites and interment. There appears to be a temporal break of 1000 years before the widespread and varied practices of Bronze Age tomb construction, which lasted through the third millennium BC. After another break in monument construction, tombs were reused in the first millennium BC, sometimes with successive ritual visits. The data presented offer new material for the interpretation of the lives and activities of prehistoric pastoralists throughout the Holocene.