A system for uploading content includes a sender capable of sending an upload request, where the upload request comprises a request to upload content from the sender to a recipient. The system also includes a network entity, such as the recipient, capable of operating an upload agent. The upload agent, in turn, is capable of receiving the upload request, and thereafter determining an upload schedule relating to the time and/or manner of uploading the content. The sender can then be capable of uploading the content to the recipient in accordance with the upload schedule. The network entity can be further capable of recovering an upload session that has encountered an interruption.