At a time of global uncertainty in trade and investment regimes, Singapore’s investment policy-makers have been involved in negotiating ‘next generation’amendments to the Singapore-Australia Free Trade Agreement, while also resurrecting a familiar framework where necessary or expedient – i.e., bifurcating EU-Singapore trade and investment commitments into two separate agreements; namely, the EU-Singapore Free Trade Agreement and EU-Singapore Investment Protection Agreement.Singapore Courts are also prepared to review investment treaty-based arbitral awards afresh. Kingdom of Lesotho v Swissborough Diamond Mines is the second case where an investor-State arbitral tribunal’s award was closely scrutinized by the country’s apex court, and the in this instance the Singapore Court of Appeal held that the arbitral tribunal did not have jurisdiction and ultimately set aside the arbitral award. Analyzing these developments, this chapter suggests that Singapore is emerging as a standard-setter in investment policy and investor-state dispute settlement jurisprudence via the interpretation of investment-related treaty provisions.