The ethnographic data of the Bleek-Lloyd archive pertaining to the ǀXam Bushmen (San) of the Karoo have been marshalled to great effect in developing understandings of Bushman rock art throughout southern Africa, with implications for archaeological interpretations of hunter-gatherer rock arts worldwide. Rock art from their homelands, however, has received comparatively little attention, and obvious historical content—which would tie the art to the socio-cultural milieu of the Bleek-Lloyd informants—has occasioned relatively little comment. This paper returns to one site (the Strandberg) known to have been a prominent feature in the cultural landscape of the ǀXam to explore the historical imagery present there, examining the ways in which this art demonstrates the ongoing vitality of certain aspects of ǀXam life in the face of the dramatic socio-cultural changes experienced by these groups from the nineteenth to early twentieth centuries. The paper investigates the range of potential authors for the art, and looks at the context of its production within the expansion of global markets, violent interactions and shifting subsistence options that characterized the late nineteenth-century Northern Cape.