Post-Kantian philosophers typically hold there to be a coincidence between reason and freedom. In this paper, I question their ability to secure this coincidence. I do so in particular by examining the work of John McDowell: probably the leading light of contemporary analytic post-Kantian philosophy, and certainly someone for whom the coincidence is important. Working through McDowell, I argue that in order to be considered ‘rationally free’ in relation to the external world, the world itself needs to, at at least (...) some level, elude rational understanding. In the conclusion, I claim that this invites greater engagement – particularly by post-Kantian philosophers working in the analytic tradition – with the work of Theodor Adorno. (shrink)