The present invention provides a system and method for transmitting a file associated with an email message from an issuer device in a network to a recipient device in the network. The email message and file are generated by the issuer device in response to a request received at the issuer device. The system comprises a proxy server in the network, processing software operating on the proxy server and transmission software operating on the issuer device. The transmission software operating on the issuer device has an attachment selection module and an attachment transmission module. The attachment selection module generates an attachment identifier related to the file, the attachment identifier identifies the issuer device, a version of the file and a location in the network for the proxy server. The attachment selection module further generates an email for transmission to the recipient device, the email having the attachment identifier attached thereto. The attachment transmission module forwards the version of the file towards the recipient device in response to a transmission request received from the proxy server. The processing software operating on the proxy server has request processing module and an issuer interface module. The request processing module processes a received request from the recipient device to process the attachment identifier. The issuer interface module generates and sends the transmission request to the issuer device in response to the received request, the transmission request providing the attachment identifier to the issuer device.