This chapter explores three of the challenges that public buyers face when designing public tenders to support smart urban mobility initiatives and when supervising the execution of the relevant contracts. First, the chapter covers emerging issues around access and re-use of transport data that may be hindering ‘outside of the box’ thinking and the deployment of artificial intelligence in this area. Second, it discusses some well-known ‘inside the box’ regulatory issues around the exercise of discretion in the choice of sustainable technological solutions, the constraints surrounding certain types of complex and collaborative procurement, and the difficulties in monitoring contract compliance clauses. Third, the chapter arrives at the realisation that the main challenges in delivering and supporting smart urban mobility through procurement relate to the higher-level or cross-cutting challenges of the professionalisation of the procurement workforce and the need to bridge significant (and growing) knowledge gaps. It thus explores existing policy interventions aimed at the professionalisation and networking of procurement officials. The chapter concludes with some overall reflections, and a call for a more active role to be taken by the new Von der Leyen Commission.