To address challenges in last mile logistics, various projects and companies globally are developing pilot tests of new vehicles and use cases. This collaborative effort involves stakeholders from retail, logistics, software and hardware development, and regulatory bodies. It is essential not only to define application areas and technical solutions jointly but also to adapt existing technologies, align different interests, and meet regulatory requirements. The BeIntelli project, implemented in the center of Berlin, serves as one such example. It features an autonomous van and four delivery robots, utilizing a two-tier delivery system. In this system, the van operates as a mobile hub, distributing packages to robots for final delivery and integrating seamlessly with the existing urban infrastructure. For groceries, deliveries are initiated directly from stores by the robots. Given the novelty of the BeIntelli project, numerous procedural dependencies and undefined processes were encountered. This paper summarizes these challenges and extracts generalizable insights from the deployment of autonomous delivery mechanisms. Key findings highlight the technical reliability of system components, the demands placed on technology partners, and the navigation of regulatory landscapes, especially concerning the acquisition of operational licenses. The empirical data and experiences gathered from the BeIntelli project provide valuable lessons for stakeholders in last mile logistics, encouraging broader adoption and refinement of autonomous delivery systems. The study emphasizes the need for collaborative efforts across retail, logistics, technology, and regulatory domains to implement such innovative solutions.