Since the enactment of the first safe harbours and liability exemptions for online intermediaries, market conditions have radically changed. Originally, intermediary liability exemptions were introduced to promote an emerging Internet market. Do safe harbours for online intermediaries still serve innovation? Should they be limited or expanded? These critical questions—often tainted by protectionist concerns—define the present intermediary liability conundrum. In this context, this paper would like to explain the recent developments in intermediary liability theory and policy within a broader move towards private ordering online. Public enforcement lacking technical knowledge and resources to address an unprecedented challenge in terms of global human semiotic behaviour would coactively outsource enforcement online to private parties.Online intermediaries’ governance would move away from a well-established utilitarian approach and toward a moral approach by rejecting negligence-based intermediary liability arrangements. Miscellaneous policy tools—such as monitoring and filtering obligations, blocking orders, graduated response, payment blockades and follow-the-money strategies, private DNS content regulation, online search manipulation, or administrative enforcement—might reflect this change in perspective. In particular, governments—and interested third-parties such as intellectual property rightholders—try to coerce online intermediaries into implementing these policy strategies through voluntary measures and self-regulation, in addition to validly enacted obligations. This process might be pushing an amorphous notion of responsibility that incentivizes intermediaries’ self-intervention to police allegedly infringing activities in the Internet. In this sense, the intermediary liability discourse is shifting towards an intermediary responsibility discourse.Further, enforcement would be looking once again for an ‘answer to the machine in the machine’. By enlisting online intermediaries as watchdogs, governments would de facto delegate online enforcement to algorithmic tools. Due process and fundamental guarantees get mauled by technological enforcement, curbing fair uses of content online and silencing speech according to the mainstream ethical discourse.