I can think of no legitimate reason to mask your IP address when sending e-mail. I can understand that he is concerned about his on-line privacy, but there are much better ways to protect his privacy than by spoofing an IP address, which can still be traced anyway. Almost every server the message in question touches will readable by the system Admins, unless the message has been encrypted by the originator. If he is worried about receiving SPAM then use multiple e-mail accounts and set up a white list for his friends. He needs to face the facts......there is no true anonymity on the Internet!