The paper presents a non-destructive diagnostic technique based on guided wave propagation phenomenon used to assess the adhesive bonding between a steel bar and a concrete cover. Double-layered cylindrical specimens with different levels of debonding and its location were investigated. The influence of bonding length on the excitation of multiple modes of longitudinal guided waves was analysed. Numerical simulations of guided wave propagation in healthy and damaged specimens were conducted and differences in the occurring phenomena were specified. The analysis of the obtained results confirms the possibility to apply the guided wave propagation method in the assessment of degradation level in the adhesive bonding of multi-layered cylindrical structures.