A method implemented by a computing system includes receiving, from each of a plurality of content presentation devices, a request for supplemental content. Each content presentation device is configured to present program content received from a content distribution system, wherein the program content is associated with a program schedule that specifies an advertisement start time. The computing system determines, for each of the plurality of content presentation devices, a supplemental content processing time that corresponds to an amount of time required by a particular content presentation device to receive the supplemental content to facilitate presentation of the supplemental content. The computing system schedules the plurality of content presentation devices to receive requested supplemental content according to corresponding supplemental content processing times and advertisement start times. Content presentation devices having higher supplemental content processing times and earlier advertisement start times are scheduled to begin receiving requested supplemental content before content presentation devices associated with lower supplemental content processing times and later advertisements start times. Supplemental content is subsequently communicated to the content presentation devices according to the schedule.