The primary role of high-density polyethylene (HDPE) packaging is to ensure the protection and preservation of the products it contains by preventing any external alteration. However, interactions such as migration and sorption (from the product to the packaging) can occur. These phenomena not only affect the polymer’s properties, such as its crystallinity, but also the quality of the packaged products, leading to toxicological or organoleptic changes. During storage, transport, or handling, they may cause irreversible deformations. Similarly, sorption can alter the appearance (e.g., discoloration, loss of gloss) and mechanical properties of the packaging, such as impact or compression resistance. This study aims to experimentally investigate the evolution of the mechanical strength of HDPE packaging subjected to vertical compression as a function of physical aging induced by a sorption-simulating product (pentyl acetate). A damage law was developed based on compression strength calculations. Additionally, the oxidation index was calculated using Fourier-transform infrared spectroscopy (FTIR), along with the diffusion coefficient. The results revealed a correlation between the increase in oxidation index, the diffusion coefficient, and the reduction in mechanical compression properties.