The conclusion of the Transatlantic Trade and Investment Partnership (TTIP) constitutes a priority and key component of the external trade policy of the European Union (EU). It is also an immediate follow-up to several years of regulatory cooperation between the two global trade powers. In an era of megaregionals, services is the only area where significant negotiating traction exists at the bilateral and multilateral level. However, recent events such as the imminent Brexit and the withdrawal of the USA from the Transpacific Partnership (TPP) cast doubt on the future of trade deals. Even so, services remain a key sector of export interest for the EU and thus completing agreements such as the TTIP or the Trade in Services Agreement (TiSA) is of crucial importance, allowing the EU to create new opportunities for service suppliers but also to reshape the regulatory philosophy governing the future regulation of global trade in services. With respect to TTIP, the EU Commission, backed by the EU executive, has advanced an ambitious agenda and submitted a conditional offer to the US, hoping for further liberalization on the two sides of the Atlantic. Against this backdrop, this article offers a critical account of the EU external trade policy, focusing on the EU’s recent external action with respect to services liberalization. The article advances three theses: first, that such ambitious agreements mark a new era of offensive services strategy which, however, is contained by internal conflicts and disagreements regarding certain still sensitive silos such as audiovisual or public services and Brexit shall exacerbate such internal conflicts in the medium run; second, that megaregionals can be used to accelerate domestic regulatory reform and openness in the service sector; and third, that TiSA will constitute a litmus test for the EU’s commitment to the World Trade Organization (WTO) cause. When appropriate, the article draws parallels with existing EU legislation and case law; other EU Free Trade Agreements such as the recently concluded Comprehensive Economic and Trade Agreement (CETA) with Canada; the General Agreement on Trade in Services (GATS); and TiSA.