On 24 September 2024, a side event titled "Smart Communities: AI, Digital Transition, and Social Change" was co-organised by the Living-in.EU (Go.Li.EU) and CommuniCity projects at the annual OpenLivingLab Days, hosted by the European Network of Living Labs. Held in Timisoara, Romania, this in-person event brought together representatives from diverse sectors and thematic areas. The programme comprised three main components: a) An introduction to the Go.Li.EU and CommuniCity projects, explaining how cities, technology providers, and other stakeholders can engage with and benefit from their offerings. b) An interactive session focused on engaging stakeholders to identify the challenges cities face on their journey towards digital transition, highlighting key issues and gaps to address. c) An interactive debate on the social implications of digital transition and the use of big data in public management. This summary presents the main outcomes from Part B, the interactive session, where participants collaboratively identified core problems and challenges facing cities, communities, academia, and industry during the process of digital transformation. The insights shared here aim to inform and support cities and other affected stakeholders as they plan for and navigate the digital transition.