Urban transport is facing an increasing number of problems. Innovative technological solutions have been proposed for many of these problems. The implementation of these solutions, however, is surrounded by many uncertainties—for example, future relevant developments for urban transport demand and supply, the possible consequences of these developments for urban transportation system performance, and the way crucial stakeholders will value these consequences. In order to deal with these uncertainties, a flexible or adaptive policy is proposed that takes some actions right away and creates a framework for future actions that allow for adaptations over time as knowledge about urban transport technologies accumulates and critical events with respect to the implementation of these technologies take place. The adaptive approach is illustrated for three promising technological solutions for urban transport problems: (1) intelligent speed adaptation, (2) personal intelligent travel assistant, and (3) underground freight transport.