Urban resilience and smart cities have emerged as a critical agenda for urban development in the twenty-first century. The growing emphasis on smart and resilience concepts is mostly due to increasing shocks and stresses related to the environmental, economic, social, and technological pressures which is also exacerbated by the uncertainty associated with rapid urbanisation, climate change, and resource limitations. While digital smart solutions are becoming increasingly critical in addressing these challenges, it is essential to consider its broadest systemic impacts to ensure that new vulnerabilities are not created, and resilience compromised by adopting and using digital technologies in urban systems (Kupers, R., & Foden, M. (2017). Learning for resilience and complex systems thinking. Agenda setting scoping studies summary report. The Resilience Shift.) note “no complexity, no resilience” but conversely, it is also important to recognise that “systems can fail, even if everything works as it is supposed to”. The aim of this paper is to investigate if the complexity drawn by introducing smart digital technologies in urban systems enhance resilience or create vulnerabilities? For this purpose, a deep case study analysis is conducted in Melbourne, Australia investigating the extent to which the current smart city initiatives contribute to the urban resilience attributes or have the potential to do so. Melbourne has dubbed as the most livable city in the world in several years and leads the nation as the most innovative city in Australia. Yet, despite its many efforts and relative wealth overall, the city faces risks and stresses that weaken the fabric of the society, which entrench disadvantage and may trigger the shocks of the future. Melbourne is exposed to natural disasters such as extreme heat, bushfires and floods, extremist acts, and of course the pandemics. There is an increasing number of smart city initiatives taking place in Melbourne, however, the extent to which these initiatives are aligned with the overall strategic plan of the city for resilience and sustainability objectives or just ad-hoc projects for testing new exciting technologies, is what we have investigated in this chapter.