Last-mile delivery (i.e., the delivery of merchandise to a store or end user), is a prime target for digital transformation. It is the most expensive and fastest growing leg of the supply chain and often the most critical to customer satisfaction. Unfortunately, it is also the most complex leg of the supply chain. We will discuss the delivery characteristics and trends that make digital transformation a necessity. We will also discuss the five stages of digital transformation necessary to optimize delivery systems: 1. Data digitization; 2. Business intelligence; 3. Predictive analytics; 4. Automated delivery planning; and Adaptive management. Finally, we will examine the advances in technology that enable transformation of last-mile delivery.