A research framework is formed by the semantics of the “green” macrosystem, supported by a methodological approach, data analysis, and forecasting, with a focus on the dynamics of transition to a qualitatively new state. The purpose of the work is to develop conceptual provisions and methodological tools for assessing the implementation of the concept of a “green” macrosystem. Applying methods of system analysis, content analysis, formalization, statistical analysis (technologies of knowledge discovery in databases and time series analysis), and discriminant analysis contributed to achieving the goal. As a result of the research, the categorical apparatus of a “green” economy was clarified by outlining narrow and broad approaches to defining the “green” macrosystem; the author’s method of assessing the implementation of the concept of the “green” macrosystem was modified by expanding the list of factors of greening the economic system, transforming the condition of the “green” corridor to calculate the developed dynamic coefficient of transition to the concept of the “green” macrosystem (DCGM), and adapting the method to the macrosystem level; the regularities of a transition to the concept of a “green” macrosystem were revealed. The novelty of the study lies in the proposal of an integral DCGM indicator, which avoids the problems of normalization, weighting, and loss of relevant data, incorporates the determinants of the “green” economy (natural resources and pollution), and relies on available data. The formulated provisions develop the theoretical basis on which to transform the macrosystem to the “green” concept and can be taken into account in the implementation’s framework of strategic planning documents for the greening of production and economic systems.