Droughts represent one of the most significant natural hazards, with far-reaching impacts, especially in vulnerable regions such as Southern Portugal. This study investigates long-term changes in drought characteristics across this region over the past four decades, focusing on severity, spatial patterns, and variability. Two meteorological indices—Consecutive Dry Days (CDD) and RL10 (days with \(<\) 10 mm precipitation)—were analyzed for the periods 1980–2000 and 2001–2020 using data from 17 meteorological stations. Findings reveal a marked intensification of droughts and rising spatial uncertainty. A Joint Drought Index (JDI), combining both indicators through multidimensional scaling, highlights a northward expansion of drought. To support early detection and mitigation of drought events, a Random Forest-based short-term alert system capable of accurately forecasting drought severity classes at the monthly scale was developed. These findings offer a flexible tool that can be applied to other regions, contributing to global efforts in managing drought-related risks.