Abstract: In this paper I argue that Adorno's metacritique of freedom in Negative Dialectics and related texts remains fruitful today. I begin with some background on Adorno's conception of ‘metacritique’ and on Kant's conception of freedom, as I understand it. Next, I discuss Adorno's analysis of the experiential content of Kantian freedom, according to which Kant has reified the particular social experience of the early modern bourgeoisie in his conception of unconditioned freedom. Adorno argues against this conception of freedom and suggests that freedom is always conditioned by our embodiment and by our social and historical situation. Finally, I turn to Adorno's criticism of Kant's discussion of freedom and determinism in the Critique of Pure Reason and argue that while his philosophical argument against Kant fails, his metacritical argument remains suggestive. Scepticism about freedom arises when the standpoint of theoretical reason encroaches upon the standpoint of practical reason and assimilates persons to things.