Why does Kant say that a “skeptical satisfaction of pure reason” is “impossible” (A758/B786)? I answer this question by giving a reading of “The Discipline of Pure Reason in Respect of Its Polemic Employment.” I explain that Kant must address skepticism in this context because his warning against developing counterarguments to dogmatic attacks encourages a comparison between the critical and the skeptical methods. I then argue that skepticism fails to “satisfy” [befriedigen] reason insofar as it cannot “pacify” reason’s tendency to (...) go beyond its own boundaries. The skeptical method reveals the past failures of dogmatic metaphysics but cannot rule out future successes. Only critical knowledge of reason’s proper bounds can do this, thereby pacifying our restless reason. I close by arguing that Kant’s discussion implies that a skeptic must feel dissatisfied with her renunciation of metaphysics, and that this dissatisfaction can lead her to take interest in Kant’s critical philosophy. (shrink)