This paper discusses the results of a detailed functional study of 16 microlithic backed tools made on quartz, and newly excavated at Sibudu Cave, KwaZulu-Natal, South Africa. The layers associated with the artefacts have OSL ages of 61.7 ± 1.5 ka, 63.8 ± 2.5 ka and 64.7 ± 1.9 ka and represent the Howiesons Poort Industry at the site. I show that more than 50% of the pieces could hardly have been used in any way other than to tip arrows in a transverse position. This outcome supports previous inferences that some of these small stone tools, and perhaps a bone point from the same context, signify the use of bow and arrow technology during the Middle Stone Age. In addition to transversely hafted arrow tips, there is also evidence that some of the tools could have been hafted diagonally. Such tools could have been used equally successfully as arrow tips or barbs, or as barbs for hand-delivered spears. The variation in hafting configuration for these geometric shapes signifies hunting technologies that were flexible and most likely adapted according to need, preference, season and/or prey type.