In the works of Kant and Rawls, we find an acute sensibility to the pre-eminent importance of freedom of speech. Both authors defend free speech in democratic societies as a private and as a public entitlement, but their conceptions markedly differ when applied to non-liberal and non-democratic societies. The difference is that freedom of speech, for Kant, is a universal claim that can serve as a test of legitimacy of all legal orders, while for Rawls, some legal orders are owed full recognition even if they do not in principle guarantee freedom of speech. I explain Kant’s account of free political speech and argue that the defence of individual rights should be seen as its core feature, both in republican and in autocratic states. I then argue that a much-overlooked shift in Rawls’s development to Political Liberalism likewise ties his account of free speech in democratic societies to issues concerning rights and justice. In a next step, I discuss Rawls’s perspective on some non-democratic regimes in his Law of Peoples, regimes that he understands as well-ordered but which do not guarantee freedom of speech. I criticize Rawls’s account from Kant’s perspective and suggest to introduce a ‘module’ from Kant’s pre-republican thought into Rawls’s conception, aiming to secure a core area of rights- and justice-related speech. My claim is that under Kant’s view of autocratic legitimacy, an important extension of speech rights is called for even in non-liberal, non-democratic states, and that a Rawlsian account should and can adopt it.