The effects of climate change on coastal areas are expected to significantly influence the risk for port operations. In the present work, a novel methodology for the quantitative assessment of the performances of upgraded rubble-mound breakwaters under a changing climate is proposed. For each considered upgrading option, the failure probability related to a certain limit state is calculated through the implementation of Monte Carlo (MC) simulations, using the factor of change (FoC) method to include the projected future climate. Three indexes are defined for the immediate and intuitive interpretation of the results: i) the ratio between the calculated and the maximum acceptable failure probability during lifetime (r); ii) the rate of the growth of the failure probability during lifetime (s); iii) the coefficient of variation of the failure probability due to both the intrinsic uncertainty of the MC simulation and the variability of future climate (v). The methodology was applied to the case study of the Catania harbor breakwater, considering the failure of different upgrading solutions due to the collapse of the outer armor layer and to excessive mean overtopping discharge. The results revealed the acceptability of the structural and hydraulic performances of all the tested configurations, under both present and future climate. Moreover, a high climate-related variability of the future failure probability was found. The usefulness of the proposed indexes for designer and decision-makers was also demonstrated. In particular, r gives direct information about the acceptability of the structure performances, enabling the immediate comparison between different configurations and climate scenarios. The index s is fundamental to calculate the appropriate times to implement repair interventions during the structure lifetime. Finally, v allows the identification of those situations which requires the design of highly flexible maintenance plans, able to adapt to a very variable climate avoiding excessive costs.