Dryland farming systems in South Dakota face rainfall variability and rising water demand, which can reduce crop productivity and threaten long-term soil health. We combined field experiments across three dryland sites in South Dakota (Roscoe, Selby, Fort Pierre) with continuous soil moisture monitoring (0-15, 15-30, 30-45 cm) and HYDRUS-1D modeling to evaluate cover crops and soil amendments (biochar, manure) on water retention. During the active cover crop growth period, plots with cover crops consistently exhibited lower soil water content than plots without cover crops, likely due to increased transpiration. Plots with no cover crop (NCC) retained more water than cover crop (CC) plots (Roscoe: 26.27% vs. 24.16% at 0-15 cm). During the primary crop growing season, biochar consistently increased soil moisture (theta) compared with manure and unamended plots. Following a 43-day dry spell (1 July-13 August 2024), soil moisture declined by approximately 0.096 m(3) m(-3) in the biochar plots, compared with 0.125 m(3) m(-3) under manure and 0.216 m(3) m(-3) in the unamended control, exhibiting differences in water retention capacity among treatments. HYDRUS inverse modeling reproduced observed soil moisture dynamics (R-2 similar to 0.91) and demonstrated higher water content under biochar. Scenario analysis using representative wet (2008) and dry (2012) years showed the cover crop + biochar combination maintained the highest average water content. Results support integrating biochar with cover cropping to buffer drought and improve soil water availability in dryland farming.