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High-frequency electromagnetic (EM) surveys have shown to be valuable techniques in the study of soil water content due to the strong dependence of soil dielectric permittivity with moisture content. This quantity can be determined by analyzing the average value of the early-time instantaneous amplitude of ground-penetrating radar (GPR) traces. We demonstrate the reliability of this approach to evaluate the shallow soil water content variations from standard fixed-offset GPR data by simulating the data over different likely EM soil conditions. A linear dipole model that uses a thin-wire approximation is assumed for the transmitting and receiving antennas. The homogenous half-space model is used to calculate the waveform instantaneous amplitude values averaged over different time windows. We analyzed their correlation with the soil surface dielectric parameters, and we found a clear inverse linear dependence on the permittivity values. Moreover, we evaluated how different kinds of noise affect this correlation, and we determined the influence of the electrical conductivity on the trace attributes. Finally, through a two-layered medium, we estimated the effect on the GPR signal of a shallow reflector, we analyzed how its presence can carry out inaccuracies in the soil surface dielectric permittivity estimation, and we determined the best time window to minimize these errors.