In this chapter, I aim to recover and reconstruct the philosophical potential of transcendental critique as a foundational but underexplored model within critical theory. While the Frankfurt School often prioritizes dialectical approaches rooted in Hegel and Marx, I argue that Kant’s conception of critique—centered on the conditions of possibility for rational action—offers essential normative tools for social analysis. I define transcendental critique not as an external moralizing gaze but as an internal critique, grounded in the very structures that make autonomous action possible. This involves assessing social practices in light of their coherence with the principle of non-contradiction of the will and their capacity to sustain freedom and justice. Drawing on Kant’s practical philosophy and philosophy of history, I show how critique functions teleologically—not in a deterministic sense, but as an orientation toward emancipation and a cosmopolitan order. I also engage with Habermas’s attempt to update this model through discourse ethics and communicative action, noting both its promise and its limitations. I conclude by reaffirming that transcendental critique, properly understood, is immanent to historical practices, capable of diagnosing their contradictions, and indispensable for imagining transformative alternatives. It retains a vital role in renewing critical theory’s normative foundation.