The Singapore judiciary is not known for actively or robustly pushing the national constitutional discourse in a way that can be observed in highest courts in other matured jurisdictions. That is however not to say that the Constitution leads a dormant existence: on the contrary, its role and the meaning of its provisions are very much in the political and public domain, and increasingly so in recent years. This paper examines how non-judicial actors in Singapore formulate, push for and engage with each other’s interpretation of constitutional requirements. In addition, it queries the underlying considerations and incentives that may shape their decision to speak out – or refrain from doing so. The Singapore experience shows how the nature of the political settlement, combined with other extra-legal dynamics, determine whether and how legally created opportunities for constitutional guardianship are, or fail to be, exercised.