This article explores the early Schleiermacher's attempts to deal with difficult philosophical problems arising from Kant's ethics, specifically Kant's notion of transcendental freedom. How do we connect a transcendentally free act with the nature of the subject? Insofar as the act is transcendentally free, it cannot be understood in terms of causes, and this means that it cannot be connected with the previous state of the individual before he or she engaged in the act. I work through Schleiermacher's grappling with this problem by taking a thorough look at some of Schleiermacher's early essays and reviews. My main focus will be Schleiermacher's early essay On Freedom, written between 1790-92. I will, however...