Anaerobic digestion (AD) is widely used for the sustainable treatment of biological wastes and the production of biogas. Its byproduct, digestate, is a valuable organic waste and needs appropriate management, which is one of the major concerns with a negative impact on the efficiency of biogas installations. One approach to extend the utilization of digestate as well as improve its handling and storage characteristics is compaction into pellets. This study aimed to evaluate the behavior of digestate during cyclic loading and unloading in a closed matrix. The findings presented here may provide insights into the mechanisms of pellet formation for optimizing the production of pellets and improving their sustainable management. The study can be considered novel as it applied cyclic loading, for the first time, in view of densification modeling and pelleting prediction. A Zwick universal machine was used in the experiments. The moisture content of digestate was found to be 10–22%. Samples were loaded with a constant amplitude of 20 kN for 10 cycles. The distribution of energy inputs, including the total energy, energy of permanent deformations, and energy lost to elastic ones, was thoroughly evaluated. A decrease in the total loading energy was observed in the first cycle, in cycles 2–10, and after all 10 applied cycles due to the rise in the moisture content of digestate. Similar relations were also found for the nonrecoverable energy part. In subsequent cycles of loading/unloading, the values of total energy and permanent deformation energy fell asymptotically. One of the most noteworthy findings of the study was that the absolute values of elastic deformation energy were consistent across all the cycles and moisture levels. However, it was noted that the percentage of energy dissipated to elastic deformation in all cycles significantly increased as the moisture content increased. Loading, which contributed to elastic deformations, was identified as the key factor causing an increase in cumulative energy inputs, and the majority of the energy expended was dissipated. Dissipated energy was the only component that permanently altered the total energy required for compaction. Another important finding, which resulted from the analysis of successive courses of loading and unloading curves, was that the shape of the areas enclosed between the loading/unloading curves was significantly influenced by the moisture content of the digestate.