The period extending from the Autumn of 1906 to the “Five Lectures” of the Spring Semester 1907 marks a turning point in Husserl’s development. With the lectures on logic and theory of knowledge in the Winter Semester of 1906/07 we find a first breakthrough to and analysis of phenomenological reduction. While the “Five Lectures” from the Spring Semester of 1907 are generally identified with the first elaboration and analysis of phenomenological reduction, we see that Husserl’s struggle with the temptations of dogmatism (Scylla) and skepticism (Charybdis) lead here to a sketch of reduction as a passage through ‘logicizing structuralism’ on the one hand and ‘psychologistic genetism’ on the other hand (J. Derrida). This essay will pursue a close reading of the 1906/07 lectures to examine the issues of (1) the relationship between dogmatism (objectivism, idealism) and skepticism (empiricism, psychologism, historicism); (2) differences between dogmatic and critical skepticism; (3) the decisive emergence of epoché and reduction; and (4) the status of the phenomenon between psychology and phenomenology. In the course of the analysis, the essay will point toward the “Five Lectures” of the Spring Semester of 1907, specifically on the problem of two kinds of transcendence and immanence.