An efficient use of plasticizers in rubber compounds requires an understanding of their miscibility behavior. Besides the chemical properties of both rubber and plasticizer, the rigidity of the plasticizer plays an important role for their miscibility. The miscibility is investigated here using the glass transition measured by differential scanning calorimetry and broadband dielectric spectroscopy (BDS). Additionally, the interfacial relaxation and phase separation measured by BDS are confirmed by transmission electron microscopy. While the flexible plasticizer, poly-(α-methylstyrene), stays miscible in a silica-filled polybutadiene rubber compound, the more rigid plasticizer, indene-coumarone (IC), shows a phase separation at high concentrations. The phase-separated IC tends to accumulate at the silica surface.