As the Electric Vehicle (EV) gains market share, utilities and policy decision makers will be challenged to provide and manage the increased grid demand. Fleets such as metro transits and product delivery services (Amazon, Fedex, UPS, etc.) will soon be electrified. Fleets and their respective depots pose tremendous challenges to the grid’s ability to provide the necessary power. These challenges will be discussed through an urban layout example illustrating a customer with more than 50 EVs overlaid with the potential grid options available. This demonstration will provide a high-level overview of the potential impacts a utility transmission and distribution engineer will have to account for during the oncoming electrification of fleet vehicles.