Failed deliveries cost companies billions of dollars each year, while impacting customer satisfaction and damaging retailers’ reputations. The author shares findings from original research based on transaction and delivery data from an e-commerce retailer in a Latin American megacity and a delivery company in Singapore. He and his colleagues also interviewed delivery drivers to understand the issues they encounter on the road. Based on these insights, the author offers three suggestions for how companies can deliver packages more successfully: 1) planning delivery sequences to account for the deliveries with the greatest risk of failure, 2) reducing the loads on trucks and drivers’ schedules, and 3) decentralizing warehouse locations and dividing cities into delivery zones. These low-cost solutions can reduce failed delivery attempts by up to 10%, including in dense urban areas and developing countries.