India's IT rules struggle with Generative AI, as tech evolution has outpaced legislation. The Calcutta High Court's Indiamart vs OpenAI case underscores this dilemma: AI chatbots generate content, complicating intermediary liability and safe harbour provisions. The Information Technology Act of 2000, designed for passive platforms, cannot adequately classify active Generative AI systems. This mismatch raises complex questions about legal attribution, creating an untenable situation where neither classifying AI as an intermediary nor an originator fully resolves the issue. A new legal framework is urgently needed to address this technological shift and ensure appropriate regulation.