ABSTRACT Since the 1990s, Singapore has sought to project itself as innovative and technologically cutting-edge through narratives such as ‘intelligent island’, digital ecosystem’, and more recently, ‘smart nation’. The Smart Nation initiative is aimed at digitising and, ‘datafying’ as many public services as possible. To this end, the government launched a National Artificial Intelligence Strategy in 2019 that envisions Singapore as a global hub for developing, test-bedding, deploying, and scaling AI solutions. In late 2023, the same year Generative AI entered public consciousness thanks to ChatGPT, Version 2.0 of Singapore’s AI strategy was released. Providing a commentary of Singapore’s digital journey and its governing approaches, this paper contends that AI is more than just a new digital tool for Singaporeans; it is also a proxy for Singapore’s digital and ‘smart nation’ global reputation.