The chapter tests stakeholder acceptability and their likely behavior change with respect to innovative solutions for improving urban freight transport efficiency and fostering city sustainability. It presents the case of the Rome LL within the EU CITYLAB project, where an innovative system for integrating direct and reverse logistic flows in the urban area has been set up. This innovative system has been set up with the aim of improving clean waste collection so as to increase the amount of recycled materials while also minimizing the amount of transport‐related CO2 emissions. An ex ante behavioral analysis based on a stated preference survey has been conducted to investigate stakeholder preferences for different scenario configurations associated with recycling, so as to boost the success of the initiative and promote sustainable behavior. Results show that an environmentally friendly transport system and the gamification process associated with recycling are the most important attributes for stakeholders.