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The present article considers Heidegger's thinking about the concept of "system" in Schelling's treatise on Freedom (1809). Heidegger's thoughtful reference to Schelling's treatise is research on the principle of system formation and the question of the possibility of a system of freedom as a question about the essence of being. In his interpretation, the necessity of establishing freedom in the system, is raised in the framework of this basic principle of idealism, which is necessary for the establishment of a system, the search for the shaping principle of being, and the research on how it is possible to have a connection in the ground of being. Therefore, the guiding questions of this article are, why does the system become the main point of controversy and the most necessary demand in German idealism? And according to Heidegger's interpretation, to what extent was Schelling successful in establishing a system compatible with freedom?