This chapter considers the encounter of skepticism with the Kantian and post-Kantian philosophical enterprise and focuses on the intriguing feature whereby it is assimilated into this enterprise. In this period, skepticism becomes interchangeable with its other, which helps understand the proliferation of many kinds of views under its name and which forms the background for transforming skepticism into an anonymous, routine practice of raising objections and counter-objections to one’s own view. German philosophers of this era counterpose skepticism to dogmatism and (...) criticism, ancient to modern skepticism, and, importantly, conceptualize the transitions from one form to another, which forms the conceptual matrix in which new disciplinary forms, such as psychology, anthropology, and historicism contend for cultural-intellectual standing beside philosophy. I present this assimilationist trajectory by reviewing three well-known moments of this encounter of skepticism and idealism: (1) Kant’s idealization of skepticism as a floating position amidst various philosophical positions through the dialectic, polemics, systematics, and history of pure reason; (2) Fichte’s schematic conception of skepticism as a dispute of systems in the early Wissenschaftslehre following his review of the skeptic G. E. Schulze’s attacks on Critical philosophy; (3) Hegel’s historicizing conception of skepticism in the context of differences between subjective idealism and speculative thought and his early Jena review of another work by the same skeptic Schulze. (shrink)