Surface-enhanced Raman scattering (SERS) is attracting increasing interest for chemical sensing, surface science research and as an intriguing challenge in nanoscale plasmonic engineering. Several studies have shown that SERS intensities are increased when metal island film substrates are excited through a transparent base material, rather than directly through air. However, to our knowledge, the origin of this additional enhancement has never been satisfactorily explained. In this paper, finite difference time domain modeling is presented to show that the electric field intensity at the dielectric interface between metal particles is higher for “far-side” excitation than “near-side”. This is reasonably consistent with the observed enhancement for silver islands on SiO2. The modeling results are supported by a simple analytical model based on Fresnel reflection at the interface, which suggests that the additional SERS signal is caused by near-field enhancement of the electric field due to the phase shift at the dielectric interface.