AbstractCharacteristics and physical features related to low precipitation across many years in Southern Africa that lead to societal disruptions are diagnosed using observed analyses and an ensemble of historical coupled climate model simulations during 1921 to 2014. Four regions are evaluated, as identified through a hierarchical clustering algorithm applied to the Standardized Precipitation Index (SPI) during the October–April precipitation season. Although dryness spanning many October–April occurs periodically in each region, they seldom occur simultaneously, consistent with largely insignificant SPI cross‐correlations between them. However, characteristics relevant to low precipitation across many years are generalizable between the four regions, including the serial persistence of October–April precipitation, the likelihood of consecutive dry October–April, and the likelihood of dry October–April in temporal extents of up to 10 consecutive such 7‐month seasons. Systematic precipitation persistence is not a feature in any of the four Southern Africa regions, as serial correlations of October–April SPI are not statistically significant at any time lags. It follows that there is an exponential‐folding decay in the likelihood of consecutive October–April for various SPI thresholds and that there is a large spread in the likelihood of low October–April SPI across many years. In terms of physical features, low October–April SPI in each Southern Africa region is closely related to local atmospheric circulations; however, they are not as closely related to sea surface temperatures (SSTs). These results suggest that dryness spanning many years is determined primarily by persistent local circulations related to atmospheric variability and to a lesser extent variability related to SST anomalies, including the El Niño–Southern Oscillation.