UPS, the leading logistics provider in the world, and long known for the efficiency of its operations, began a journey to modernize and streamline even further its pickup and delivery operations in 2003. The result is the “On Road Integrated Optimization and Navigation” (ORION) system. Every day, ORION provides an optimized route for each of UPS' 55,000 U.S. drivers based on the packages to be picked up and delivered on that day. Costing more than $295 million to build and deploy, ORION is expected to save UPS$300–$400 million annually. ORION is also contributing to the sustainability efforts of UPS by reducing its CO2 emissions by 100,000 tons annually. To bring this system from concept to reality, UPS instituted extensive changes in management practices to ensure that both users and executives would accept the system. By providing a foundation for a new generation of advanced planning systems, ORION is transforming operations at UPS. This talk will discuss some of the challenges of designing, implementing, and deploying a vehicle routing system on such a large scale in the real world. It will also provide brief discussion of some of the technical issues and challenges in formulating and solving the underlying vehicle routing problems, which are solved with a proprietary metaheuristic optimization system. These challenges include the need to respect numerous time windows of different kinds, the need to account for consistency (i.e., routes cannot change too much from day to day), and the need to account for preferences of planners and drivers.