For the past two decades, The E-Commerce Directive has been the cornerstone of regulating illegal content on online platforms in the European Union, and its safe harbors have played a crucial part in the development of various internet intermediaries such as internet Service Providers (ISPs), search engines, social networks, cloud service providers, e-commerce platforms, web hosting companies, domain name registrars, content aggregators etc. In those early days of the commercial Internet, policymakers realized that the commercial and social potential of this new medium could best be realized if service providers were protected against direct liability for the words of their users. Without it, scalability of the kind achieved by Facebook and Twitter would never have been possible. However, as the platforms have grown in their influence over our exercise of fundamental rights such as freedom of expression, this has turned into a double-edged sword. The decisions made by these platforms increasingly shape contemporary life as they have basically become governance structures. Triggered by the rise of hate speech on social media following the immigration crisis in Europe, and by acting first and asking questions later, the EU is currently hard at work calling for internet intermediaries, or online platforms, to be more proactive in helping to prevent unlawful content and activity on the internet, mainly through self-regulatory mechanisms. However, it is proving difficult to adjust the current liability protections and to promote a transparent and consistent use of infringement prevention methods across this sector. In this paper we will analyze the current legislative process around the issue and how these developments in technology and intermediary infrastructure continuously shape and command balance between various interests and fundamental rights at stake.