In this study, we propose a methodological framework to identify and evaluate cost-effective pathways for enhancing resilience in large-scale interdependent infrastructure systems, considering decision-makers’ risk preferences. We focus on understanding how decision-makers with varying risk preferences perceive the benefits from infrastructure resilience investments and compare them with upfront costs in the context of high-impact low-probability (HILP) events. First, we compute the costs of interventions as the sum of their capital costs and maintenance costs. The benefits of the interventions include the reduction in physical damage costs and business disruption losses resulting from the improved resilience of the network. In the final stage, we develop statistical models to predict the perceived net benefits of different network resilience configurations in power, water, and transport networks. These models are employed in an optimization framework to identify optimal resilience investment pathways. By incorporating Cumulative Prospect Theory (CPT) in the optimization framework, we show that decision-makers who assign higher weights to low probability events tend to allocate more resources towards post-disaster recovery strategies leading to increased resilience against HILP events, like earthquakes. We illustrate the methodology using a case study of the interdependent infrastructure network in Shelby County, Tennessee.