I had the same problem some time ago. You need to configure gmail to send email through your SMTP server rather than through gmail to replace the "Sender:" header appropriately. Option available in Gmail settings > Accounts and Import > Send mail as.. section > Add another email address.... ------------------------------ Date: Mon, 01 Feb 2010 16:12:35 -0700 From: Bob Meetin <bobm at dottedi.biz> To: "thelist at lists.evolt.org" <thelist at lists.evolt.org> Subject: [thelist] gmail - From: and Sender: Message-ID: <4B675FE3.3030302 at dottedi.biz> Content-Type: text/plain; charset=ISO-8859-1; format=flowed With your gmail account, I know of the feature where you can configure the From: line in the header to display "me at mydomain.com <mailto:me at mydomain.com>", but what about the "Sender: " line? It's not obvious how/where you can set that up to be in sync? It all needs to reflect the same address, return address, from address, sender address. Need a visual: http://www.dottedi.biz/images/diagnostics/gmail-sender.jpg The Tooltip shown is from hovering over Bob Meetin.