This article examines the liability of YouTube for copyright infringing content uploaded by its users. We take the cue from the recent and potentially momentous request for a preliminary ruling on this topic, submitted by the German Supreme Court to the Court of Justice of the European Union (CJEU). Existing rules on internet service provider (ISP) liability in the EU leave wide discretion to Member States. Even where harmonised, important questions of interpretation remain. Despite being the subject matter of a lively academic debate, core issues are still far from settled. Our analysis aims to shed light on the different approaches Italian and German courts have adopted to address the question of ISP liability for copyright infringements. For this purpose, we have selected the case currently awaiting the CJEU’s decision, Frank Peterson v YouTube, and an Italian case with a similar factual basis, Delta TV Programs v YouTube. We reflect on the most recent decisions in each case as well as on the rulings in lower instances. In both cases, the national courts have dealt extensively and systematically with the question of YouTube’s liability for copyright infringements, advancing various legal arguments in favour and against. We show that the approaches of the national courts to the question of YouTube’s liability present significant divergences with respect to four main issues: the primary liability of YouTube, the determination of its “active role”, the requirements for notification of an infringement, and the obligation of YouTube to prevent re-uploads. Differences in these aspects can be observed not only between the two Member States, but also within their national case law. While awaiting the verdict by the CJEU and the ultimate decision by the EU legislator on the directive for copyright in the Digital Single Market, this article provides an understanding of the core legal questions at stake and a basis to build expectations on whether the “Time to Say Goodbye” to a safe harbour for YouTube is indeed approaching.