Distribution schedules designed a priori may not cope adequately with unexpected events that occur during the plan execution, such as adverse traffic conditions or vehicle failures. This limitation may lead to delays, higher costs, and inferior customer service. This chapter presents the design and implementation of a real-time fleet management system that handles such unexpected events during urban freight distribution. The system monitors delivery vehicles, detects deviations from the distribution plan using dynamic travel time prediction, and adjusts the schedule accordingly by suggesting effective rerouting interventions. The system has been tested in a Greek 3PL operator and the results show significant improvements in customer service.