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With the advent of Artificial Intelligence (AI), more and more organisations are incorporating this into their business processes to make better decisions. The field of urban planning is not excluded in this realm of technology. In fact, although urban planners and AI developers operate in different disciplines, they both share the same goal: creating a more livable future. With technological advancement, AI technology can be incorporated into urban plans, facilitating the development of a “Smart City”. Yet, while members of the public might only take note of the infrastructural changes within the city to make the city “smarter”, such as smart lamp posts, increase of digital registers on different outlets and modes of transportation, increase in Wifi hotspots etc., more could be done to understand the true impact of urban planning decisions and the public’s sentiment. This can help gauge feedback to be used as one of the success metrics and as a case study for future similar urban planning cases.