A ground based content server transfers content to an aircraft based content server via courier devices that are transported by aircraft passengers. Content files to be delivered to a target aircraft are identified. Courier devices associated with persons scheduled to become passengers on the target aircraft are identified. Each of the content files are divided into content fragments, where the content fragments collectively contain all data necessary for reassembling the content files. The content fragments are distributed from the ground based content server across the courier devices, so that each courier device is distributed one of the content fragments containing data that is at least partially redundant with data contained in one of the content fragments that is distributed to at least one other one of the courier devices and that is not redundant to data contained in other content fragments distributed to still other ones of the courier devices.