Extreme climatic events, such as droughts, hinder progress toward achieving the sustainable development goal of food security. South Africa is vulnerable to drought‐related agricultural losses, which have led to food insecurity. However, few studies have focused on the long‐term impacts of drought on crop production at a regional scale. Therefore, we aimed to examine the intensity, magnitude, and trend of rainfall‐based short‐term agricultural drought at the provincial scale in South Africa based on the Standardized Precipitation Index (SPI). Additionally, we analyzed the impact of agricultural drought on maize yield by calculating the Standardized Yield Residual Series (SYRS) and Crop Drought‐Resilience Factor (CDRF). To this end, we collected rainfall data from 29 stations across nine provinces along with maize yield data for the period of 1993–2022. Agricultural drought analyses based on the three‐month (SPI‐3) and six‐month (SPI‐6) SPIs demonstrated dynamic variations in occurrence, with Sen's slope indicating that 10 stations exhibited a significant increase in drought events across South Africa. Notably, SPI‐6 analysis showed that Gauteng, Free State, and North West provinces experienced the highest percentages of severe to extreme drought events during the study period, at 4.17%, 3.89%, and 3.61%, respectively. Furthermore, the majority of provinces in South Africa experienced an extreme SPI‐6 magnitude ranging from −46.03 in Western Cape Province to −61.6 in Free State Province. The dynamic effects of agricultural drought on maize yield revealed that the maximum yield loss of 13% occurred in 1993 in Eastern Cape Province, while some provinces experienced no yield loss during certain years. However, CDRF analyses identified Western Cape (CDRF [SPI‐3] = 0.52, CDRF [SPI‐6] = 0.62) and Mpumalanga (CDRF [SPI‐6] = 0.7) provinces as the most vulnerable to food insecurity due to the severe non‐resilience of maize to drought in these regions. This study reveals the complex interplay between climatic extremes and maize yield variability, providing valuable insights for managing regional food production systems and ensuring future food security in South Africa.