Reliable soil moisture information is essential for agricultural drought warning, but tropical smallholder regions often lack ground networks for validating satellite products. This study evaluates CYGNSS Level 3 soil moisture in Guinea savanna agriculture over Benue State, Nigeria, from 2021 to 2023. Extended Triple Collocation was applied to CYGNSS, SMAP Enhanced Level 3, and ERA5-Land anomalies. Quadruple Collocation then used ESA CCI ACTIVE as a fourth product to quantify CYGNSS-SMAP error dependence. The standard SMAP-inclusive configuration gives CYGNSS a correlation with unknown true soil moisture of r = 0.425, an error standard deviation of 0.036m3m−3, and a signal-to-noise ratio of −6.56 dB. Quadruple Collocation identifies a CYGNSS-SMAP cross-error correlation of 0.325 and reduces the SMAP-independent CYGNSS estimate to r = 0.386, indicating that SMAP-inclusive validation overstates retrieval skill. Performance is weakest under dry soils (r = 0.331), where drought detection is most important, and location-level ETC convergence fails during Harmattan conditions as anomaly variance collapses. Skill is higher over cropland (r = 0.447), shrubland or grassland (r = 0.455), and moderate precipitation conditions (r = 0.630), but lower over tree cover (r = 0.342). These findings show that uncorrected CYGNSS Level 3 soil moisture is not sufficient for standalone year-round drought monitoring in Guinea savanna agriculture. Its value is strongest in bias-corrected, multi-sensor systems that account for vegetation, soil moisture state, precipitation history, land cover, and seasonality.