The rapid evolution of internet culture, particularly meme culture and dark humour, has significantly outpaced the legal and judicial frameworks governing online expression in India. Digital satire, parody, and humorous content have emerged as important forms of public discourse; however, creators frequently face criminal proceedings under laws that were not designed to address the unique characteristics of online communication. This article examines the tension between the constitutional guarantee of freedom of speech and expression under Article 19(1)(a) of the Constitution of India and the potential criminal liability arising from online conduct under the Bharatiya Nyaya Sanhita, 2023 (BNS) and the Information Technology Act, 2000. Employing a doctrinal legal research methodology, the study analyses relevant constitutional provisions, statutory frameworks, judicial precedents, and scholarly literature relating to online speech regulation. Particular attention is devoted to BNS provisions concerning defamation, public mischief, promoting enmity, obscenity, and religious offence, as well as Sections 67 and 67A of the Information Technology Act, 2000. The article evaluates the manner in which these provisions have been applied to memes, political satire, and dark humour, highlighting the absence of a coherent legal standard for distinguishing protected expression from punishable conduct. To address this doctrinal gap, the article proposes a Contextual Harm Test (CHT), a four-pronged analytical framework requiring consideration of: (i) communicative intent, (ii) actual or probable harm, (iii) audience reception within the relevant digital community, and (iv) the proportionality of criminal prosecution as a response. The proposed framework draws upon constitutional free speech principles, the harm principle, and contemporary proportionality jurisprudence. The article argues that adoption of the CHT by courts or through legislative reform would promote greater consistency, protect legitimate online expression, and ensure that criminal sanctions are reserved for conduct causing genuine and demonstrable harm.