when I used it with Gmail it would always appear to people as "From me@gmail.com on behalf of me@wherever.edu". This doesn't happen if you configure an externa

when I used it with Gmail it would always appear to people as "From me@gmail.com on behalf of me@wherever.edu". This doesn't happen if you configure an external SMTP server in Google Mail for the alias. http://gmailblog.blogspot.de/2009/07/send-mail-from-another-address-without.html http://gmailblog.blogspot.de/2009/07/send-mail-from-another-... https://support.google.com/mail/answer/22370?hl=en https://support.google.com/mail/answer/22370?hl=en Moreover, you don't want to use a different 'from' address without sending through the appropriate SMTP server. If the domain has SPF or DKIM set up, a receiving server might reject your mail if it wasn't sent from an expected SMTP server.