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 fo...