The rapid proliferation of digital media platforms has democratized content creation and distribution, enabling a vast spectrum of voices to be heard. It has brought about a significant shift in media entertainment landscapes worldwide, with India being a prominent case study due to its vast and diverse content consumption patterns. The massive content on the Internet has also raised concerns regarding misinformation, copyright infringement, and cultural sensitivity. Therefore, in the context of media entertainment, the regulation of the digital era presents a vast complex array of challenges for policymakers. Thereby, it analyzes the regulatory challenges and policy perspectives; addressing how India is navigating the complexities introduced by digital technologies. The study outlines India’s current regulatory framework including legislative measures. Apart from this, the paper contains exploration of challenges of balancing free speech with societal norms in a country characterized by its cultural pluralism. The authors of the article argue that rational regulation is able to help to prevent the spread of misinformation, protect national security, and ensure privacy. It can play a pivotal role in promoting national integration by fostering unity, preventing communal tensions, and ensuring equal representation. To achieve the objectives, the paper analyzes three case studies — Swami Ramdev v. Facebook, Inc.* (2019), the Tandav Controversy (2021), and the Tiktok ban for privacy and security concerns (2020). In the later section, the authors analyze and compare the regulatory framework of different states including India, the United States, European countries, Australia, and China. In the end, the paper summarizes the need for changes in the regulatory framework and also recommends policy measures that may be implemented to safeguard the consumers’ interest, preserve cultural values, and ensure the integrity of content.