<p>Extreme climatic events pose significant challenges to natural resource management and jeopardize the sustainability of rainfed agriculture. This research investigates the interactions between Climate Extreme Indices (CEIs) and Weather-Related Crop Production Indicators (WRCPIs) for wheat (<i>Triticum aestivum</i>) and olives (<i>Olea europaea</i>) within Jordan’s diverse agroecological zones utilizing stepwise multiple regression analysis. We also examined correlations and trends spanning from 1995 to 2022 across four key regions: Irbid, Amman, Mafraq, and Karak. Findings reveal that precipitation-related indices based on a station in Irbid exhibit a positive correlation with Jordan’s wheat yield (correlation coefficient &gt; + 0.41), suggesting the beneficial effects of increased moisture variability. Conversely, temperature indices based on Karak station demonstrate a stronger correlation with wheat production (correlation coefficient &gt; − 0.45). For olive cultivation, CEIs such as the Average Temperature of Cold Months and the Optimum Temperature (OPT) are positively correlated with production outcomes (correlation coefficients ranging from 0.43 to 0.55). In contrast, production faces negative correlations (-0.41 to -0.56) with indices like Diurnal Temperature Range (DTR), Frost Days, and Maximum Daily Maximum Temperature. Zone-specific regression models significantly enhance predictive accuracy, reflecting the nuanced influence of CEIs and WRCPIs. In Irbid, olive production is notably influenced by factors including Consecutive Dry Days, the Simple Day Intensity Index (SDII), and Maximum Minimum Temperature. In Amman and Mafraq, optimal models highlight temperature variables, including OPT, Minimum Temperature, Spring Average Highest Temperature, and Annual Average Temperature (AAT) as critical predictors. Trend analyses suggest potential increases in wheat yields in Irbid and Karak, attributed to rising DTR and a declining frequency of Growing Season Minimum Temperatures below 5&#xa0;°C. Olive production is also projected to rise, driven by upward trends in OPT, SDII, and AAT. These results underscore the vulnerability of rainfed agriculture to climatic extremes and emphasize the urgent need for proactive adaptation strategies. Policymakers are urged to implement targeted management practices to bolster resilience and ensure the sustainability of agricultural productivity in the face of climate variability.</p> Graphical Abstract <p>This graphical abstract provides an overview of the influence of different Climate Extreme Indices (CEIs) and Weather-Related Crop Production Indicators (WRCPIs) on wheat (<i>Triticum aestivum</i>) and olives (<i>olea europaea</i>) production across arid agroecological zones in Jordan. The collected data consists of zone-specific meteorological records employed to calculate the historical CEIs (based on CMIP5 definitions) and WRCPIs over the study period (1995–2022). Similarly, zone-specific crop production data were collected for the same period, as illustrated in the time series crop production graphs in the center of the graphical abstract. Statistical inferences were conducted to examine the possible relationships between the CEIs and WRCPIs with crop production trends. The impact of climatic-related variables on <i>T. aestivum</i> and <i>O. europaea</i> production was both zone-specific and crop-specific as shown in the lower right boxes. Furthermore, the lower left boxes represent the best-fit regression models that identified key climatic variables driving crop production in each zone. These results underscore the need for climate monitoring, scenario development, and adaptive strategies to enhance crop resilience in vulnerable areas.</p>