<p>Examining the interplay between cracks and voids is a pivotal aspect in understanding the failure mechanics of materials that undergo plastic deformation under loading conditions. This study uniquely focuses on the quantitative estimation and evolution of plastic dissipation rates during crack–void interaction, an area relatively underexplored, particularly in the context of plastically compressible solids exhibiting strain softening behavior. A novel contribution of this work also lies in the decomposition of plastic dissipation into two parts involving hydrostatic and deviatoric stress components, enabling a more detailed understanding of energy absorption and dissipation mechanisms during fracture. The investigation considers two distinct material behaviors—bilinear hardening and trilinear hardening–softening–hardening—and evaluates their influence under Mode I loading conditions using finite deformation finite element analysis. Results show that plastic compressibility leads to generate higher plastic dissipation rate and thus reduces the crack and void growth. When there is strain softening in the material, there are some fluctuations in the plastic dissipation curve and the presence of material softening allows the material to withstand more load without much crack and void growth.</p>