The emergence of social media has raised new and interesting questions concerning the regulation of free speech. One such question is the legal treatment of the sharing of third party digital content. Using the example of a ‘retweet’, this article highlights the urgent need to establish clearer liability standards for those sharing, repeating or endorsing illegal or infringing content. It attempts to propose a clear, principle-based approach that lifts the cloud of uncertainty creating a chilling effect on speech. This act of retweeting is sought to be analysed against various legal frameworks including defamation, copyright infringement and public order. It is seen that unlike an intermediary that enjoys safe harbour protection, the retweeeter is treated on par with a principal actor. The law as it stands today does not differentiate between the repetition and original posting of content. This has a chilling effect on the act of sharing and reduces the diversity of voices on the internet. For these reasons, it is argued that a retweeter must be protected as a traditional internet intermediary. Finally, this article postulates a legal framework for attributing liability to the retweeting of illegal and infringing content that accounts for the unique context of social media communications.