The failure of thermal barrier coatings (TBCs) during service is a critical issue affecting aeroengine efficiency. In this study, electron beam physical vapor deposition (EB-PVD) TBCs were subjected to thermal cycling at 1100 °C. Terahertz time-domain spectroscopy (THz-TDS) was employed to characterize the relationship between the evolution of characteristic frequency and the number of thermal cycles, along with the development of stress in the ceramic layer. In situ tensile test revealed a linear correlation between the characteristic frequency and micro strain derived from THz-TDS data, with a proportional coefficient of −9.94 between the characteristic frequency and the slope of the refractive index curve. The results show that the stress evolution can be effectively monitored by recording the trend of characteristic frequency. During the non-failure stage, the characteristic frequency followed a parabolic trend as thermal cycles increased, influenced by the growth of thermally grown oxide (TGO), ceramic layer sintering, and thermal mismatch. Approaching the failure stage, stress evolution was dominated by the expansion of vertical cracks in the ceramic layer and the widening of transverse cracks at the interface, which corresponded to a sudden change in the characteristic frequency.