Abstract: The aim of this article is to explore the origin of the difficulty of founding the reflecting power of judgment as Kant outlines it in the Preface of the third Critique. Although a foundation for this faculty was only established in 1790, we must interpret it as a critical solution to an old problem, which Kant had already recognized around 1770. Through his comprehension of the meaning of healthy understanding and native wit he already confirms the impossibility of determining the correctness of our judging activity from the use of rules. This approach of the problem must be understood in the context of the controversy about the concept ‘logica naturalis’ in the Leibniz-Wolffian aesthetics and logic. In close conjunction with this tradition, Kant already tries to offer an elucidation of the question of judging through the aesthetics.