This article addresses Slovenia as a case of a post -communist country in terms of its sustainable development. It deploys an in -depth historical analysis and extensive empirical data while exploring Slovenian society through the analytical lens of morpho-static/morphogenetic approach (Archer 2017). The focus is on (1) the country’s structural and cultural settings in each selected period in order to explore whether there has been a mutual reinforcement of the levels of both, contributing to the sustainable development; (2) ways in which agents respond to such changes reinforcing or changing the structural settings. The selection of quantitative structural indicators of sustainable development is based on the indicators of sustainable development that have a direct reference to the Sustainable Development Agenda of the United Nations 2030 and also adopted by the current Strategy of Development of Slovenia. The selection of survey data was based on their connection with the same sustainability issues and their availability for a longer period, particularly close to the time points of the cycles observed. The findings show that in terms of contributing to sustainable development, the presence of morphogenesis in the selected cycles turns out to be rather limited, and there is a severe lack of political reflexivity (cf. Al -Amoudi 2017) among actors.