Guided electromagnetic wave propagation using ultra-wideband signals is a barely new approach for damage detection. However, still many challenges are present, including the way to deal with the GHz domain signals and the physics behind the interaction phenomena enabled by any type of flaw. The present work proposes a feasibility analysis for a structural health monitoring system employing permanently integrated microwave sensors. This setup allows to interrogate the structure continuously using multiple transmitters and multiple receivers when the electromagnetic waveguide is established. To this end, a metallic plate is equipped with a dielectric waveguide patch attached to the structures’ surface. To validate the detectability of damage, a reversible defect is modeled through removable bolts accessible from the other surface of the plate. The experiments are carried out considering different bottom holes at different spatial locations of the plate. In addition, concurrent measurements are adopted to characterize the noise level within the signal. The characteristic changes of electromagnetic wave signals are caught using a damage index approach returning whether the defect can be detected sensitively or not. Different coupling conditions are used to let the guided electromagnetic waves propagate and interact with underlaying structure. The results show that this approach can be adopted for damage detection with a reasonable signal to noise ratio, especially when the waveguide is well coupled. In addition, both transmission and reflection loss can be monitored reliably.