Freedom of speech and expression is a critical indicator of the health of any society and guarantee of such freedom is integral to democracy. Yet, does a legal or constitutional guarantee necessarily translate into lived experience? One of the ways to measure freedoms is to examine the treatment meted by the State to literary and cultural dissent and resistance. In this session, we examine the status of free speech and expression in Mughal India by focussing on the treatment of dissenting and irreverent poets. Though modern India positions herself as the world’s largest democracy guaranteeing to her citizens freedom of speech and expression, in practice her writers are fettered in multiple ways. In contrast, even at the pinnacle of the allegedly authoritarian Mughal rule, the plenitude of dissenting and irreverent literature produced suggests that, while applicable laws may have been illiberal, practice was rather free. Is a professedly secular democracy giving her writers a shorter licence to disagree than ostensibly intolerant monarchies of the past?