This study describes and analyzes the recovery of transportation systems damaged by flooding and landslides in 2018 on the island of Kaua’i, Hawai’i. Following describing the record-setting rainfall and massive landslides that closed the major highway connecting the North Shore communities with the rest of the island, the challenges of “building back better” are investigated. While there was an urgency to finish the roadway repairs as quickly as possible, there was also a need to reduce future risks from flooding and landslides. Strong leadership, coordination, communications, and resource sharing helped improve pre-existing traffic, congestion, parking, and accessibility concerns for residents and tourists. There are important lessons learned concerning the need for timely, accurate data and information. Mitigation and adaptation projects that go beyond simply replacing and repairing assets before the storm are also analyzed. Opportunities to utilize greener, nature-based, and context-sensitive design, engineering, and planning solutions to mitigate and adapt highways to climate-induced extreme events remain challenging even in a community known for scenic beauty, pristine natural areas, and rich cultural heritage. While the community-led efforts to implement improvements to the State park at the end of the road were exemplary, there are still ongoing challenges of increased climate threats and inflexible, limited systems for funding—not just in disaster recovery but also investments in community resilience.