In 1972 the UK signed an accession treaty with the EU while Switzerland and the EU concluded a free trade agreement. Nowadays, both countries have a very close relationship with the EU and are not (or not anymore) EU Member States. This article aims to analyse two complex legal paths taken by countries able but not willing (or no longer willing) to be part of the EU through institutional arrangements they have already negotiated or are currently negotiating with the EU. On the one hand, the UK was part of the EU legal order and is now extracting itself from the realm of EU law while switching to relations with the EU based on international law. On the other hand, Switzerland has built its relations with the EU on numerous bilateral agreements based on EU law without establishing a homogeneous institutional mechanism, which the EU has been insistently demanding since 2013. These two situations are paradoxically similar as for both of them the design of institutional arrangements depends on the degree of integration with/extraction from EU law. A comparison between the EU–UK withdrawal agreement, the EU–UK Trade and Cooperation Agreement (TCA) and the EU–Switzerland draft institutional agreement, as proposed in this article, confirms that the degree of institutional flexibility that the EU is able to offer to a third country with which it concludes an agreement is dependent on whether that agreement is based on EU law, and in particular, EU internal market law. This article argues that depending on the nature of law the agreement is based on, from an EU perspective variations in the role of Court of Justice of the European Union (CJEU) and/or of an arbitral tribunal may make sense, but this is not the case when one takes an outside perspective.