Abstract: A system and method of sharing files from a private network to a remote device. A persistent connection to a communication server is created by a client agent installed on a file sharing source device at the private network. Remote file sharing client devices connect to the communication server to access files from the file sharing source device via the communication server. A media services connector allows direct uploads of files from the file sharing source device to media service providers. A transcoder may be provided on the file sharing source device to reduce the need for transmitting large files over the network.