The health and climate crisis are calling for an urgent re-evaluation of concepts such as resilience and sustainability and how we measure and implement them, sifting the debate towards the role urban design and planning play in driving urban transitions. Recent studies have been introduced to investigate the dynamics of the pandemic in urban areas and the ample literature on tools and methods for measuring vulnerabilities. The paper calls for a need to re-scale urban planning down to a human level by bridging space syntax attributes with measures of resilience. It introduces a data and evidence-based approach framework for driving urban transitions utilizing risk assessment (National Risk Index) and a vulnerability measuring index (City Resilience Index) to quantify spatial attributes which foster sustainable practices. A scenario testing method is proposed to make urban design more consistent with the strategic mission of urban planning driving resilience and transition.