The interaction of ultrasonic waves with interfaces formed by two non-conforming, rough surfaces in contact has been the subject of numerous investigations [1–10]. The motivations behind these studies have been various: from the assessment of the real area of contact between two rough surfaces [1], to the modeling of crack closure near the tip of a fatigue crack [4]; from the identification of the nature of interfacial imperfections in kissing and partial bonds [6], to the generation of ultrasonic waves [8]. In most of these studies, the characterization of the interfacial properties has been attempted by studying the reflection of longitudinal and shears waves at normal incidence. Only recently, the problem concerning the interaction of ultrasonic waves with realistic complex systems such as that formed by two neighboring imperfect interfaces has been addressed. Lavrentyev and Rokhlin [9, 10] used ultrasonic spectroscopy to evaluate the interfacial conditions from the spectra of longitudinal and shear waves reflected normally from the interfaces.