The relation between Kant’s conception of modalities in the Postulates of Empirical Thought and Hegel’s conception in the Logic of Essence has not been addressed in the current scholarship. I argue that there is in fact a close connection that becomes visible if the desideratum which is implied by Kant’s conceptions is understood. Thus, after an analysis of the Kantian modal postulates, the article shows that they are sufficient to characterize the necessity of Kant’s Grundsätze and, hence, a specific form (...) of synthetic propositions a priori. However, I will prove that they are insufficient to characterize Kant’s synthetic propositions a priori about transcendental philosophy. This insufficiency in the characterization of transcendental philosophy itself brings into the arena Hegel, who supplements the Kantian modalities with a self-reflexive form of transcendental modality. (shrink)