Abstract Despite considerable interest in the application of land surface data assimilation systems (LDASs) for agricultural drought applications, relatively little is known about the large-scale performance of such systems and, thus, the optimal methodological approach for implementing them. To address this need, this paper evaluates an LDAS for agricultural drought monitoring by benchmarking individual components of the system (i.e., a satellite soil moisture retrieval algorithm, a soil water balance model, and a sequential data assimilation filter) against a series of linear models that perform the same function (i.e., have the same basic input/output structure) as the full system component. Benchmarking is based on the calculation of the lagged rank cross correlation between the normalized difference vegetation index (NDVI) and soil moisture estimates acquired for various components of the system. Lagged soil moisture/NDVI correlations obtained using individual LDAS components versus their linear analogs reveal the degree to which nonlinearities and/or complexities contained within each component actually contribute to the performance of the LDAS system as a whole. Here, a particular system based on surface soil moisture retrievals from the Land Parameter Retrieval Model (LPRM), a two-layer Palmer soil water balance model, and an ensemble Kalman filter (EnKF) is benchmarked. Results suggest significant room for improvement in each component of the system.