Artifical Intelligence (AI) has become a strategic imperative for modernizing global railway networks, and SBS Transit has been on this AI transformation journey from a strategic whole-of-organisation, stakeholders-centric approach, and re-examine business strategies and processes, shifting operations from reactive maintenance to pre-amptive and predictive for a safer, more reliable and a delightful experience for the commuters in its multi-modal rail and bus transport. How should the enormous potential of AI balance with safety, regulation and public trust? What are the challenges along the journey?