Against the background of debates between “possibilism” and “actualism” within recent modal metaphysics, this chapter interprets Hegel’s sketchy criticisms of the abstract formalism of Kant’s practical philosophy as a consequence of his deeper metaphysical critique of Kant’s treatment of modality. Despite Kant’s critique of the epistemic pretensions of Leibniz’s metaphysics, he had nevertheless retained the underlying framework of Leibniz’s “possibilism” within the domain of practical philosophy. Arnauld had countered Leibniz with the claim that we can only ever conceive of possible substances through the ideas of actual ones, and in a similar spirit, Hegel would criticize the lack of determinacy in Kant’s formal categorical imperative. A possible action can only be conceived through the idea of an actual one, and so in order for a moral concept to have a purchase on an individual’s actions, it must rely upon contents supplied by the positively and negatively evaluated actions found within the Sittlichkeit of a concrete community. This analysis is guided by the ideas of John Findlay, whose interpretation of Hegel was shaped in the context of such modal metaphysical debates.