Weather, as an important factor for traffic conditions, will have increased significance in South-East Europe (SEE) due to ongoing climate change. Consequently, SEE countries in transition will need to reconsider their winter road maintenance (WRM) practices. This article aims at providing a starting point for improving WRM practice. Focusing on Serbia, the article first provides a critical evaluation of existing WRM state of the practice. The core issue identified is a lacking practice in economic evaluation of WRM investment decisions. In addition, the article presents methodology and an example case study for economic evaluation of WRM investment decisions based on costbenefit analysis. Results indicate an economic justification for investing in improved WRM practice. Finally, the article concludes that WRM policy improvements need to base on knowledge transfer from international best practice, improvement in performance measurement, methods, and technologies, accompanied with an essential change in institutional culture to accommodate policy learning.