The union of technology and transportation is leading to advancements in how decisions are made and deployed for winter maintenance activities. Federal Highway Administration (FHWA) is investigating the use of artificial intelligence (AI) to collect and analyze data that could dramatically improve winter maintenance operations, safety, and mobility, as well as reduce costs and labor hours and enhance pavement design and management. Data-Driven MDSS (Dr. MDSS) looks to AI to provide next-level analysis of real-world situations in real time, addressing the risks and challenges of conducting onsite assessments.