Querying Poulsen’s view that some States negotiate investment treaties in ‘bounded’ rational ways, this article focuses on how the recently concluded European Union-Singapore Free Trade Agreement (EUSFTA) illustrates the evolution of Singapore’s treaty practice. Singapore has abandoned the ‘old’, and has joined the bandwagon of next-generation FTAs; yet, shrewdly, it is not fully convinced about the ‘new’ either. For example, the EUSFTA does not include a most-favoured nation clause, and does not commit to an appeals mechanism, unlike its Canadian and Vietnamese counterparts. Singapore’s caution appears to be motivated by a pragmatic desire to avoid the pitfalls that these provisions could bring with them, as Investor-State arbitration (ISA) jurisprudence demonstrates, and to study the implications of a recent decision by the EU’s highest court regarding the FTA. Indeed, that shows that the EU itself is now equally wary of the ISA regime removing disputes from the jurisdiction of national courts.