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Over the past two decades, successful estimation of soil moisture has been accomplished using L-band microwave radiometer data. However, remaining uncertainties related to surface roughness and the absorption, scattering, and emission by vegetation must be resolved before soil moisture retrieval algorithms can be applied with known and acceptable accuracy using satellite observations. Surface characteristics are highly variable in space and time, and there has been little effort made to determine the parameter estimation accuracies required to meet a given soil moisture retrieval accuracy specification. This study quantifies the sensitivities of soil moisture retrieved using an L-band single-polarization algorithm to three land surface parameters for corn and soybean sites in Iowa, United States. Model sensitivity to the input parameters was found to be much greater when soil moisture is high. For even moderately wet soils, extremely high sensitivity of retrieved soil moisture to some model parameters for corn and soybeans caused the retrievals to be unstable. Parameter accuracies required for consistent estimation of soil moisture in mixed agricultural areas within retrieval algorithm specifications are estimated. Given the spatial and temporal variability of vegetation and soil conditions for agricultural regions it seems unlikely that, for the single-frequency, single-polarization retrieval algorithm used in this analysis, the parameter accuracy requirements can be met with current satellite-based land surface products. We conclude that for regions with substantial vegetation, particularly where the vegetation is changing rapidly, any soil moisture retrieval algorithm that is based on the physics and parameterizations used in this study will require multiple frequencies, polarizations, or look angles to produce stable, reliable soil moisture estimates.