Past, present, and future transportation infrastructure planning, design, and operations and maintenance all contend with some degree of uncertainty. Risk-based frameworks have served the engineering practice well until recent times; now climate non-stationarity has begun to impact the ability of assets to perform their desired function over their design life. Traditional risk-based tools provide valuable insights regarding asset and system climate vulnerability, but their use is often challenged by limits of available climate model output as well as the need to consider an asset’s criticality and operational lifetime. While less widely used, there are other existing tools that more explicitly address risk including structured decision analysis, scenario planning, and iterative risk-based approaches. However, it is increasingly clear that the changing climate requires new thinking to provide more resilient infrastructure. Novel strategies are emerging but will require the sector to change, incrementally or radically, how business is done. These strategies call for infrastructure to be flexible enough to adapt to unpredictable future changes and to have metrics for monitoring performance and triggering predetermined actions. Such enhanced adaptive capacity will benefit the sector’s performances given other challenges, including increasing connection to and dependency on systems-of-systems, changing ecosystem, and institutional, and social landscapes, and the poorly understood transportation mitigation-adaptation nexus.