The relentless complexity of urban areas and the growth of e-commerce prompted by new technologies have set urban logistics at the forefront of policies for making cities more sustainable. Nowadays, municipalities are adopting strategies to mitigate the negative environmental and social impacts associated with last-mile distribution operations, but there is still a lack of conceptual background to assess their impact on sustainability. This chapter presents a methodological approach to rate the sustainability of last-mile delivery strategies based on both expert stakeholders’ perspectives and the main economic, social and environmental issues of the city where the strategy is implemented. The approach is applied to the adoption of innovative solutions in several European cities. The sustainability score offers significant value to logistics providers, urban planners, and policy-makers confronting the complexities of urbanisation and escalating delivery demands by offering strategic insights that support the transition towards sustainable urban logistics systems.