The proliferation of digital media has radically reshaped communication, journalism, entertainment, and public discourse. Platforms such as social media, OTT services, and digital news portals have democratized information dissemination, but have simultaneously ushered in complex legal and regulatory challenges. As digital media evolves faster than legislation, legal systems around the world—and particularly in India—are struggling to ensure a balance between individual rights, freedom of expression, and societal responsibilities. This chapter explores the legal challenges emerging in the digital media landscape, with a specific focus on India’s regulatory responses. It examines the tension between Article 19(1)(a) of the Indian Constitution, guaranteeing freedom of speech, and the increasing spread of misinformation, cyber defamation, hate speech, and digital harassment. In doing so, it critically analyses the Information Technology (Intermediary Guidelines and Digital Media Ethics Code) Rules, 2021, and the constitutional scrutiny they have faced. It also addresses platform liability, content takedown mechanisms, and algorithmic biases that affect content visibility and user autonomy. Additionally, the chapter investigates emerging concerns related to data privacy, surveillance, and digital profiling. The enactment of the Digital Personal Data Protection Act, 2023 is discussed in light of global data protection frameworks such as the GDPR, with attention to loopholes, implementation challenges, and judicial interpretations. Other pertinent issues explored include intellectual property violations in the digital sphere, the legal regulation of digital influencers, and ethical dilemmas surrounding AI-generated content. Using relevant Indian and international case laws, this chapter not only contextualizes ongoing debates but also highlights the urgent need for a dynamic and robust legal framework that can evolve with technological advancements. Ultimately, the chapter argues that safeguarding democratic values in the digital age requires more than reactive legislation—it demands anticipatory governance, digital literacy, judicial oversight, and international cooperation. The conclusion offers a way forward for aligning innovation with legal accountability.