Kleist’s career as a writer can be plausibly seen as the attempt to find a form of thought that might stand as a bulwark against the shock of epistemological crisis with which Kleist’s encounter with Kantianism was associated. This attempt to answer Kant’s philosophy on some level informs the approach taken in this chapter. The assumption it makes is that Friedrich Schiller became important to Kleist on account of the conscientious reckoning Schiller undertook in his middle years with respect to Kant’s philosophy. While scholarship has noted Kleist’s interest in Schiller on several occasions, Schiller’s Kantian writings have rarely been understood as an important source of philosophical orientation for Kleist in their own right. Thus, Kleist used Schiller’s responses to Kant in order to further his own interest in the question of a possible refutation of the critical philosophy. In view of Kleist’s limited philosophical training, such a refutation could clearly not take the form of a cogent philosophical argument against Kant. This chapter arges that the positions Schiller had worked out in a process of critical engagement with Kant caught Kleist’s attention and became an important component in Kleist’s own dealing with the critical philosophy. To this extent, Kleist essays and short stories in particular become readable as attempts to find a convincing response to an epistemological crisis associated with Kantianism that remained with the author as an abiding concern until his early death in 1811.