Urban logistics operations have become more complex and problematic for cities. Increasing freight and package volumes due to population growth, economic growth, and convenience impacts of e-commerce purchases are creating congestion and sustainability problems that cities must address if they are to meet the expectations of their citizens for a socially enjoyable and sustainable living space. This chapter explores the potential restructuring of how cities manage their infrastructure to achieve these objectives. Building on the fact that cities have increasingly built intelligence into their infrastructures through the installation of sensors, this chapter examines the potential for reorganizing the management of this infrastructure using blockchain, smart contract systems, and blockchain-based security to provide transparency, security, and trust to address a major roadblock to logistics collaboration efforts. Using the Physical Internet as an organizing concept for collaboration and asset sharing amongst logistics stakeholders, this chapter discusses how cities, using a blockchain-based infrastructure and a more wholistic thinking of their infrastructure management approaches, can develop a trustworthy technical infrastructure as a component of a trusted Physical Internet solution to urban logistics and its negative impacts. This chapter also describes that, while this is a necessary condition for moving forward in the management of urban logistics activities, it is not sufficient. The complex socio-technical system within which urban logistics operates requires an appropriate governance system to ensure compliance with the “rules of the game.” An approach to the development of such a system based on Ostrum’s eight constructs of effective rules for common-pool resources is proposed.