Oleg Polovynko, the Chief Advisor for Digitalization to the Mayor of Kyiv, Ukraine and Former Kyiv Chief Information Officer returns to share how the city has evolved through crisis, transforming its digital infrastructure amidst a full-scale invasion. From the launch of Misto—a platform designed to help cities adapt best practices—to reflections on the pandemic’s unexpected role in building resilience, Oleg offers powerful insights on adaptability, trust, and citizen-centric design. We also discuss digital twins, the role of AI in service delivery, ensuring data security during emergencies, and why cities everywhere should start preparing now for the unpredictable challenges ahead.