This Article explores the nature of digital monopolies and the challenges they pose to internet freedom. It then examines various regulatory approaches with their potential benefits and drawbacks, ultimately advocating for a multi-pronged strategy that fosters competition, safeguards user rights, and promotes responsible data practices, The internet, once hailed as a bastion of open communication and innovation, finds itself increasingly dominated by a handful of powerful tech corporations. These "digital monopolies" raise concerns about stifling competition, eroding user privacy, and manipulating online discourse. Striking a balance between maintaining the internet's inherent openness and effectively regulating these corporations presents a significant challenge for policymakers.