Rainfed agriculture in semi-arid regions is increasingly threatened by climate change-induced rainfall deficits and erratic dry spells, especially during critical crop stages such as establishment, flowering and maturity. These weather anomalies often extend over 2-3 weeks, significantly reducing the crop yields and threatening farmers' livelihoods. In response, real-time contingency measures (RTCM) have been introduced as a micro-level adaptive strategy to combat drought and flood events through timely and site-specific interventions. The present study conducted over five cropping seasons (2019-2024) evaluated the effectiveness of RTCM in vertisols under rainfed cultivation of drought-tolerant Sorghum K12, a short-duration climate-resilient variety. The study systematically assessed dryness and wetness periods using the rainfall-to-pan evaporation ratio and categorizing drought episodes into early, mid and terminal stages. In response to these temporal stresses, a set of climate-resilient technologies was implemented, including resowing, in-situ moisture conservation through ridge-furrow planting, closure of deep soil cracks with crop residues as mulches and foliar sprays of KCl and ZnSO4 to alleviate plant water stress. These interventions were triggered by real-time observations of soil moisture and rainfall variability. In this study, Percent Available Soil Moisture (PASM) was used as a key indicator to assess soil moisture availability, monitor agricultural drought, evaluate crop moisture stress and justify crop survival, which also supports the timely implementation of RTCM. Over the five-year period, grain yield increased by an average of 45.6 % with an annual increase ranging from 30.2 % to 58.9 % under RTC treatments compared to the control. Rainwater productivity improved significantly, ranging from 0.54 to 0.65 kg/m3 and the benefit-cost ratio (B:C) increased from 2.02 to 3.06, underscoring the economic viability of the RTCM. Biomass yield and harvest index were significantly higher under RTCM, with LSD values confirming statistical significance at 5 % level. Notably, yield stability was achieved even during low-rainfall years such as 2022-23, demonstrating the effectiveness of adaptive drought management strategies. The findings confirm that RTCM offers a robust framework to minimize drought-induced yield losses, enhance soil moisture retention and ensure profitability in vertisol-based rainfed systems of southern Tamil Nadu.