Guided waves in an elastic plate surrounded by air propagate with very low attenuation. This paper describes the effect on this propagation of compressively loading an elastomer with high internal damping against one surface of the elastic plate. The propagation of both A0 and S0 Lamb modes is considered. The principal effect is shown to be increased attenuation of the guided waves. This attenuation is caused by leakage of energy from the plate into the elastomer, where it is dissipated due to high viscoelastic damping. It is shown that the increase in attenuation is strongly dependent on the compressive load applied across the solid-solid interface. This interface is represented as a spring layer in a continuum model of the system. Both normal and shear stiffnesses of the interface are quantified from the attenuation of A0 and S0 Lamb waves measured at each step of the compressive loading. The normal stiffness is also measured independently by normal incidence, bulk longitudinal wave ultrasound. The resulting predictions of wave propagation behavior, such as attenuation, obtained by the model are in excellent agreement with those measured experimentally.