In this regard, actions have been undertaken by transmission and distribution system operators worldwide, often to comply with specific requirements imposed by regulatory authorities. This article describes a risk-based resilience assessment methodology jointly developed by the Italian transmission system operator (TSO) and RSE. The methodology aims to capture the benefits of network reinforcement operations to the system’s resilience against extreme weather events, focusing on the two most impactful threats to the Italian transmission system: wet snow and wind. The ultimate goal is to support cost-benefit analyses in resilience enhancement plans, as required by the Italian regulator for all electric utilities. An important objective is to include climate change modeling in network planning, alongside typical planning drivers such as supply security, market efficiency, and renewable integration. The case study, focused on a portion of the network, demonstrates a good correlation between the calculated return times for failures of overhead lines and the actual failure rates derived from historical datasets, as well as the effectiveness of cost-benefit analysis in prioritizing reinforcement operations for the two analyzed threats.