The feasibility of the use of epoxidized palm oil (EPO) and amine-modified epoxidized palm oil (mEPO) as process oils in silica-reinforced natural rubber compounds is studied. The chemical structures of EPO and mEPO are characterized by Fourier transform infrared spectroscopy and proton nuclear magnetic resonance spectroscopy (1H-NMR). Amine modification for 3 and 5 h leads to mEPOs with 0.03 and 0.04 mmol of amine in 1 g of oil, referred to as 0.03 mEPO and 0.04 mEPO, respectively. The properties of rubber compounds containing modified palm oils are investigated by taking those with TDAE oil and those without oil as references. The use of process oils clearly enhances the processibility (i.e., lower mixing torque and complex viscosity) and mechanical and dynamic mechanical properties of the rubber compounds as compared with compounds without oil. The rubber compounds with EPO and 0.03 mEPO show a lower Payne effect (i.e., less filler–filler interaction) than the rubber compound with TDAE because of the shielding effect of the oils on the silica surface. The use of mEPO boosts the vulcanization reaction, resulting in much better cure torque difference, which indicates a higher crosslink density due to the amino groups present in mEPO as compared with TDAE. Therefore, rubber compounds with mEPOs have better mechanical properties (i.e., reinforcement index, tensile strength, and elongation at break) and better elastic response under dynamic deformation, as indicated by a lower loss tangent at 60 °C as compared with the mix with TDAE.