A method of optimizing delivery of a dataset to a fleet of vehicles, the method comprising: based on respective transit schedules of vehicles included in the fleet, generating a transmission schedule for delivering the dataset to the fleet of vehicles over a time interval, the generating of the transmission schedule including defining a plurality of multicast transmissions, each multicast transmission of the plurality of multicast transmissions corresponding to a respective time segment of a plurality of mutually exclusive time segments within the time interval, and each multicast transmission indicating a respective portion of the dataset that is to be delivered, via multicasting during the respective time segment, to a respective subset of the vehicles included in the fleet, such that the generated transmission schedule defines a delivery of an entirety of the dataset to an entirety of the fleet of vehicles, the defining of a particular multicast transmission of the plurality of multicast transmissions including: determining, based on the respective transit schedules of the vehicles included in the fleet, a particular time segment of the plurality of mutually exclusive time segments during which a maximum number of vehicles of the fleet is scheduled to be simultaneously in transit, the maximum number of vehicles being less than a total number of vehicles included in the fleet, and the vehicles corresponding to the maximum number of vehicles being a particular subset of the vehicles of the fleet, selecting a particular portion of the dataset for multicast transmission to the particular subset of the vehicles of the fleet during the particular time segment, and scheduling a delivery of the particular portion of the dataset to the particular subset of vehicles of the fleet during the particular time segment, thereby defining the particular multicast transmission; and initiating, for each multicast transmission of the defined plurality of multicast transmissions, a respective multicast delivery of the respective portion of the dataset to the respective subset of vehicles of the fleet in accordance with the transmission schedule. based on respective transit schedules of vehicles included in the fleet, generating a transmission schedule for delivering the dataset to the fleet of vehicles over a time interval, the generating of the transmission schedule including defining a plurality of multicast transmissions, each multicast transmission of the plurality of multicast transmissions corresponding to a respective time segment of a plurality of mutually exclusive time segments within the time interval, and each multicast transmission indicating a respective portion of the dataset that is to be delivered, via multicasting during the respective time segment, to a respective subset of the vehicles included in the fleet, such that the generated transmission schedule defines a delivery of an entirety of the dataset to an entirety of the fleet of vehicles, the defining of a particular multicast transmission of the plurality of multicast transmissions including: determining, based on the respective transit schedules of the vehicles included in the fleet, a particular time segment of the plurality of mutually exclusive time segments during which a maximum number of vehicles of the fleet is scheduled to be simultaneously in transit, the maximum number of vehicles being less than a total number of vehicles included in the fleet, and the vehicles corresponding to the maximum number of vehicles being a particular subset of the vehicles of the fleet, selecting a particular portion of the dataset for multicast transmission to the particular subset of the vehicles of the fleet during the particular time segment, and scheduling a delivery of the particular portion of the dataset to the particular subset of vehicles of the fleet during the particular time segment, thereby defining the particular multicast transmission; and determining, based on the respective transit schedules of the vehicles included in the fleet, a particular time segment of the plurality of mutually exclusive time segments during which a maximum number of vehicles of the fleet is scheduled to be simultaneously in transit, the maximum number of vehicles being less than a total number of vehicles included in the fleet, and the vehicles corresponding to the maximum number of vehicles being a particular subset of the vehicles of the fleet, selecting a particular portion of the dataset for multicast transmission to the particular subset of the vehicles of the fleet during the particular time segment, and scheduling a delivery of the particular portion of the dataset to the particular subset of vehicles of the fleet during the particular time segment, thereby defining the particular multicast transmission; and initiating, for each multicast transmission of the defined plurality of multicast transmissions, a respective multicast delivery of the respective portion of the dataset to the respective subset of vehicles of the fleet in accordance with the transmission schedule.