Examining a series of legal challenges by newspaper companies in the first half-century after Indian Independence (1947), this essay examines the legal boundaries and practical content of press freedom in postcolonial India. The cases, which were concerned with official regulation of page length, newsprint allocation, and customs duties, were far from obvious attempts at censorship. And yet the petitioners claimed that such regulation of form, price, and material did, in fact, violate their constitutionally guaranteed right to freedom of speech and expression. Meanwhile, the newly democratic Indian state contended that its prescriptive directives were affirmative measures intended to protect fledgling newspapers from competition with larger conglomerates—and, thus, necessary to ensure such diversity of news and opinion as fostered genuine freedom of the press. In drawing attention to more prosaic and oblique ways in which the press can be controlled, this essay highlights the complexity of defining press freedom in practice, especially in functioning democracies that not only hope to maintain that status but also retain international credibility. The legal battles point to the tension between abstract ideas of freedom and affirmative commitments to equity as it materialized in a newly independent country with tremendous diversity. Given that these cases stretch across the Emergency (1975–77)—which remains a defining event in terms of formal state censorship in postcolonial India—they also demonstrate how routine strategies of control often have a more subterranean timeline that traverses formal disruptions in state–press relations, including, in this case, the transition from colonialism to independence.