The interdisciplinary scholarship on free speech, though developed outside the Indian context, underscores the necessity of re-examining free speech not just as an individual right against the State, but as a socially embedded phenomenon, conditioned by historical inequalities and prevailing systems of power. Building on this framework, this article advances an anti-caste perspective on freedom of speech and expression under Article 19(1)(a) of the Indian Constitution. It examines the contours of free speech in a heterogeneous and hierarchically structured society, interrogating how caste hierarchies have shaped the boundaries of acceptable speech, and determining whose speech is heard and whose is silenced. It presents how anti-caste literature, art, and social movements have challenged dominant narratives of social order and redefined the boundaries of free speech. At the same time, it highlights the structural barriers that prevent oppressed castes from fully exercising their right to free speech and dissent. These barriers fall into four categories. First, social policing and stigmatisation deter oppressed communities from expressing their views or asserting their identities publicly. Second, physical violence, including threats, social boycotts, and caste-based hate crimes, create an atmosphere of fear and intimidation. Third, legal restrictions, where existing penal laws suppress anti-caste voices, and narrow interpretation dilute the mandate of protective legislation. Fourth, epistemic barriers, where academia and media reinforce caste hierarchies through their narratives. In other words, by foregrounding the interplay between speech and social structures, the article calls for a paradigm shift in Indian constitutional law, where free speech is located within the broader struggle for liberty, equality, fraternity, dignity, and democratic inclusion.