Silica-reinforced S-SBR/BR tire tread compounds often show characteristic vulcanization profiles that do not exhibit a distinct maximum in the cure curve nor a plateau profile within acceptable time scales (marching modulus). In such a situation, it is difficult to determine the optimum curing time, and as a consequence, the physical properties of the rubber compounds may vary. Previous studies stated that the curing behavior of silica-filled rubber compounds is related to the degree of filler dispersion, the silanization, and the filler–polymer coupling reaction, as well as to the donation of free sulfur from the silane coupling agent. Such results imply that these are the key factors for minimization of the marching modulus. In the present work, various silane coupling agents with different sulfur ranks and functionalities were mixed at varied silanization temperatures. The correlation between these factors and their effect on the marching modulus intensity (MMI) were investigated. The MMI was monitored by measuring the vulcanization rheograms using a rubber process analyzer at small (approximately 7%) and large (approximately 42%) strains to discriminate the effects of filler–filler and filler–polymer interactions on the marching modulus of the silica-filled rubber compounds. Both factors have an intricate influence on the marching modulus, determined by the degree of filler–filler interaction and the coupling agent.