The idea that the Internet is a space that cannot, or should not, be regulated has been proven to be anything but true. Yet, the unique characteristics of the Internet have made its regulation problematic – to which online content regulation is no exception. Although Internet intermediaries, that perform a crucial role in providing access to, storing and linking online content, are often best suited to regulate the transmission of unlawful content, legislators have adopted a protectionist attitude towards them on the basis that the Internet, and of course Internet free speech, can only flourish if these intermediaries are allowed the space and freedom to develop their technology. The Digital Millennium Copyright Act 1998 enacted in the United States is a reflection of this attitude – providing Internet intermediaries that offer hosting and linking services with conditional immunity upon them implementing a ‘notice and takedown’ scheme that allows copyright owners to have infringing content removed from the Internet almost immediately. However, although this conditional immunity scheme favours the growth of Internet intermediaries, evidence suggests that the implementation of ‘notice and takedown’ procedures by these intermediaries runs counter to the protection of free speech rights on the Internet – leading to a paradoxical situation.