This chapter opens the “black box” of the Lion City and looks at the extent to which its government has internalised its investment obligations. With its highly efficient bureaucracy, manageable size and strong commitment to the respect of international law, the Singapore experience highlights the challenges that investment treaties can pose, even in the best of rule of law and governance conditions. Although Singapore offers a “most likely” case study for testing the plausibility of claims regarding the effects of investment treaties on the rule of law, aspects of the Singaporean experience cast doubt over the extent to which these measures are well-calibrated to the situations that commonly give rise to investment disputes. Moreover, analysis of the development of these measures casts doubt on the actual role that investment treaties – as opposed to other factors – have played in instituting them.