This comparative study aims to test the hypothesis according to which environmental awareness of planners is crucial to sustainable cities with a healthy and well connected green infrastructure able to provide ecosystem services. To test the hypothesis, we compared two cities, Bucharest (Romania) and Chisinau (Moldova), based on quantitative analyses using CORINE land cover and use data to analyze the land structure and its dynamic, and qualitative analyses focused on the planning process. Our findings suggest that both cities share a decreasing interest for planning for their green infrastructure, which was lost and fragmented. The process was aggravated in Bucharest by post-communist property restitution. Based on the results, we recommend planners in post-communist countries to give more attention to the green infrastructure, in order to produce plans fitted to the welfare and sustainability needs of people.