The stress state of the surface layer of a polymeric mass during filling of bulky compression molds is analyzed. It is shown that, at particular rheological characteristics of the mass, temperature, and filling rates, cracking of the surface layer occurs, which leads to defects in the finished products. A physical analysis of this process makes it possible to conclude that the cracks arise due to the normal stresses operating in the front region of the moving polymeric mass. It is found that, under certain flow conditions, areas with a pressure lower than the atmospheric one appear on the surface of the polymer. If the tensile stresses arising in these local regions are higher than the tensile strength of the mass, the continuity of the composition is broken in the direction determined by the greatest rate of the normal deformation. To confirm the reliability of the crack-formation mechanism proposed, the distribution of the pressure and normal stresses over the free surface is calculated based on a numerical method. These calculations show that, by comparing the stress level achieved in the front region with the tensile-strength characteristics of the polymeric composition, it is possible to predict, with a sufficient accuracy, the possibility of crack formation in the surface layer of such a mass under given flow conditions and thus to solve the question on flawless manufacturing of products.