The present study discusses that filler–filler mechanical engagement resulting from the grafted long-chain silanes on the silica surface is indeed a reinforcing mechanism in rubber composites, as already speculated by nonlinear viscoelastic properties in our previous study. The existence and severity of such a phenomenon are assessed purely by isolating the energetic contribution of reinforcement from interfering with filler mechanical engagement in the silica network formation and breakdown processes. In a novel approach, the driving force of fillers to flocculate energetically at elevated temperatures was defined using surface energy theories, and it was adjusted to be similar in two composites having silica treated by short- and long-chain silanes. Filler–filler mechanical engagement was monitored by tracking network formation (filler flocculation) in a matrix of styrene–butadiene rubber and also by conducting various dynamic viscoelastic experiments on liquid paraffin suspensions having short- and long-chain silica of similar surface energy. Results consistently confirmed the existence of mechanical engagement between silica particles having the long-chain silane in both rubber compounds and paraffin suspensions. The results may find applications in the rolling resistance of tires, for example, where stabilization of the filler network by displacing the peak energy dissipation of the network breakdown from applied service strains to larger values would be of technical importance.