Howiesons Poort (also called HP) is a technological and cultural period characterized by material evidence with shared design features found in South Africa, Lesotho, and Namibia. It was named after the Howieson's Poort Shelter archaeological site near Grahamstown in South Africa, where the first assemblage of these tools was discovered. Howiesons Poort is believed, based on chronological comparisons between many sites, to have started around 64.8 thousand years ago and ended around 59.5 thousand years ago. It is considered to be a technocomplex, or a cultural period in archaeology classified by distinct and specific technological materials. Howiesons Poort is notable for its relatively complex tools, technological innovations, and cultural objects evidencing symbolic expression. One site in particular, Sibudu Cave, provides one of the key reference sequences for Howiesons Poort. Howiesons Poort assemblages are primarily found at sites south of the Limpopo River.

While the emergence of this techno-complex is still highly debated, one leading hypothesis postulates that it emerged during a period of harsh environmental conditions and unpredictable landscapes, which may have spurned inhabitants to develop more complex tools and social structures as an adaptive response. Humans of this period as in the earlier Stillbay period showed signs of having practiced symbolic behaviors and having engaged in between-group exchanges of backed tools for the proposed function of solidifying bonds and strengthening social networks.

Many of the tools associated with Howiesons Poort resemble and seemingly anticipate many tool styles that do not appear again until far later in the archaeological record. The succeeding period, the "post-Howiesons Poort", lacks many of the complex technologies that characterize Howiesons Poort. While there is no universally agreed-upon explanation as to why this happened, there are several leading proposed theories, some of which involve shifts in resource availability and foraging strategies.

Artifacts associated with Howiesons Poort were first described in 1927 by Reverend P. Stapleton, a Jesuit schoolteacher at St Aidan's College, and John Hewitt, a zoologist and director of the local Albany museum. The two were excavating a rock shelter in the eastern Cape (later named the Howiesons Poort Rock Shelter) when they discovered an assemblage consisting of "burins, large segments, obliquely pointed blades, and trimmed points." Stapleton and Hewitt had meant to name the poort after a Mr. Howison, but they misspelled it "Howieson" in their publication. This name stuck and has been used with this spelling ever since.

Due to its affinities to Later Stone Age microliths and Upper Paleolithic tools, Howiesons Poort was originally proposed to be a variety of Magosian tools produced during a transition between the Middle Stone Age and the Later Stone Age. This transitional theory, however, was discredited during an excavation of Klasies River Caves undertaken by Ronald Singer and John J. Wymer in 1967-8. During the excavation, they uncovered key reference stratigraphic layers which showed that Howiesons Poort materials were situated both before and after Middle Stone Age layers. This finding not only contradicts the notion of Howiesons Poort as a transitional technocomplex, but pushes back the dates for these so-called "advanced" technologies.

Sites that contain Howiesons Poort assemblages are spread geographically throughout southern Africa, encompassing a variety of environments that include coastal, near-coastal, inland and mountainous. Based on an analysis of faunal remains at Klipdrift Shelter, Jerome P. Reynard et al. (2016) have proposed an environmental shift during the period, from a mixed-terrain context during early Howiesons Poort to open grasslands in mid-to-later Howiesons Poort. Upon an analysis of the frequency of faunal remains, the team found increased levels of human occupation during the period of open grasslands.

Southern African regional marine and terrestrial data indicate that Marine Isotope Stage 4, which encapsulates the known dates for Howiesons Poort, was a period of cool and moist climates. Macrofaunal data from Sibudu Cave indicate that inhabitants of the cave were hunting animals that occupied closed or semi closed environments, pointing to an access to forests. There is, however, small but significant frequencies of the faunal remains of grazers, which indicates that the inhabitants of the cave also had some access to grasslands. Therefore, there is evidence that the changing of the climate into moister conditions resulted in the development of more extensive forests, at least in the near-coastal region which includes Sibudu Cave, without completely eliminating more open savannah woodlands.

The date range for Howiesons Poort has been debated. During their 1965 excavation of the name site, archaeologists Janette Deacon and Hilary Deacon dated charcoal remains using radiocarbon dating to 19,000-4,000 years ago. However, this does not match the dates ascertained for Howiesons Poort materials at other sites, which were dated to much older time ranges. While relative dating using the stratigraphic layers at this site appeared simple to the archaeologists at first, J. Deacon noted that the range of dates contradicted those at other sites where other Howiesons Poort assemblages had been found. Deacon concluded that all Howiesons Poort materials date to beyond the range of radiocarbon dating, meaning that they are all at least 50,000 years old.