This chapter tackles the intricacies surrounding the subject of content moderation in online platforms, concerning the problem of “over-blocking”, the chilling effects it causes on the freedom of speech of users and how it affects user empowerment. It does so by analysing the evolution of the legal framework on content moderation of the last twenty years, focusing the Atlantic dialogue between European Union Law, the e-Commerce Directive, and the Content Decency Act and Digital Millennium Copyright Act. Concretely, it demonstrates the previous framework's pitfalls in ensuring the fundamental rights of freedom of expression and right to information, and how the economics of content moderation allowed for a “false positives” phenomenon (“over-blocking”). It then argues that the more pernicious effect of this comes in the form of chilling effects on users being weaponized for commercial and or political means. It concludes by scrutinizing the recent Digital Services Act’s provisions regarding the viability of the procedural mechanisms of redress for users and the accountability of the platforms and third-party stakeholders for misuse of content moderation, whether through algorithmic or individual means. The chapter resorts to a methodology of doctrinal research focused on primary and secondary sources of law.