Accurate estimation of soil water content (SWC) is crucial for effective irrigation management and maximizing crop yields. Although dielectric property-based SWC measurements are widely used, their accuracy is still affected by soil variability, soil–sensor contact, and other factors, making the development of convenient and accurate soil-specific calibration methods a major challenge. This study aims to propose a plate compression filling technique for soil-specific calibrations and to monitor the extent of soil biomass degradation using dielectric properties. Before and after biodegradation, dielectric measurements of quartz sand and silt loam were made at seven different water contents with three different filling techniques. A third-order polynomial fitting equation explaining the dependence of the dielectric constant on the volumetric water content was obtained using the least-squares method. The suggested plate compression filling method has a maximum mean bias error (MBE) of less than 0.5%, according to experimental results. Depending on the water content, silt loam’s dielectric characteristics change significantly before and after biodegradation. The best water content, measured in gravimetric units, to encourage the decomposition of biomass was discovered to be 24%. It has been demonstrated that the plate compression filling method serves as a simple, convenient, and accurate alternative to the uniform compaction method, while the dielectric method is a reliable indicator for evaluating biomass degradation. This exploration provides valuable insights into the complex relationship between SWC, biomass degradation, and soil dielectric properties.