The last mile of delivery is undergoing major changes, experiencing new demand and new challenges. The rise in urban deliveries amid the societal impacts of the COVID-19 pandemic has dramatically affected urban logistics. The level of understanding is increasing as cities and companies pilot strategies that pave the way for efficient urban freight practices. Parcel lockers, for instance, have been shown to reduce delivery dwell times with such success that Denmark increased its pilot program of 2,000 lockers to 10,000 over the past two years. This chapter focuses on challenges faced during those pilots from technical, managerial and operational perspectives, and offers examples and lessons learned for those who are planning to design and/or run future pilot tests. On-site management proved to be critical for locker operations.