Aspects of penetration resistance of rubber compounds have been studied by developing a quasi-static test. The effects of indenter material and design, nature and dosage of fillers, and crosslinking density were investigated. Indenter material was found to have a negligible contribution to the penetration characteristics of the rubber compounds, whereas the conical indenter's shape and size of the tip were important. A change in the slope of the generalized penetration characteristic curve of the developed quasi-static test was considered to be the fracture initiation point. Although fracture initiation was early at higher carbon black loading, the overall penetration resistance was improved due to hysteresis, which was in accord with the impact energy method. This was a unique observation. The carbon black–filled sample was compared with the silica-filled vulcanizate. Surface morphology of the specimens penetrated at different energy levels was examined using scanning electron microscopy. A theoretical interpretation of the forces acting at the tip of the indenter and the energy requirement while penetrating a rubber compound against a conical indenter has been proposed. The initiation energy for penetration has inverse square root dependence on the Young's modulus of the compounds. The energy required for crack propagation in contrast, was directly proportional to the Young's modulus and also correlated with the hysteresis loss and frictional coefficient for the carbon black–filled vulcanizates.