Pedestrian crossings are a staple of city design and a key feature both in terms of risk of road trauma and impacts on pedestrian experience. In car-dominated environments, the challenge is in retrofitting existing infrastructure to enable and encourage walking. It is unclear what diverse people might find difficult and to what extent existing design recommendations identify those needs. This study aims to provide a real-world perspective on local design guidelines and the Healthy Streets metrics, by triangulating them with objective measures of the built environment and users’ perceptions of unfeasibility or difficulty. The study builds on previous research having identified non-signalised crossing points experienced by interview participants (half of whom were disabled) as barriers to access. These non-walkable crossings are characterised objectively, using a range of potentially relevant metrics and specific thresholds. The study then sought the simplest way to describe those crossings, identifying the importance of three metrics: (a) peak-hour traffic; (b) complexity; and (c) turning radii for traffic. The results also identified important gaps in local design guidelines and Healthy Streets metrics, which are currently not set up to enable cities to easily identify these difficult crossings. These findings are important because they can be used to identify crossings that are likely to cause difficulties walking and should be retrofitted to support walking. They also provide indications of complementary information needed to improve local guidelines and Healthy Streets metrics to enable them to support proactive retrofit.