sendmail / Google Apps gmail smtp relay

Posted on 2010-11-18
Last Modified: 2012-05-10
  Just a bit of history we had an in house Exchange 2007 server as well as several multifunction devices, a few windows servers, 2 Linux boxes and 1 AIX box that used this Exchange server to relay mail.  Recently we moved away from Exchange and are going with Google Apps Gmail.  I was told that I could use their SMTP relay similar to exchange and went through the process of setting up one of the Linux servers to serve as the relay for all the other devices.  It actually does work but the problem I'm having is that the relayed mail is being sent to the mail box with the from address being the user name that I had setup in Gmail to authenticate.  

So for example one of the windows server which runs Crystal used to send out mails which would end up in the users mailbox with the name of the crystal server not they show up under the Gmail users name.

Another example on the other Linux box if I login in as root or another user and go through a mail command that email will show up as "root" or whomever but an application running on that box (PHP) which through a form captures the entered from address - this used to be what appeared in the mailbox - now it's as if the relay is stripping that off  and using the Gmail account.

There may not be a "Sendmail"  solution to this problem. I'm hardly a sendmail guru but if anyone has any thoughts on what is causing this or has a solution that would be great.

Question by:interstate
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LVL 26

Expert Comment

ID: 34172498
You have to add the email accounts you which to "send as" in your gmail settings:

Author Comment

ID: 34172903
    It's Friday and I will admit to being slow today.  I setup a user in gmail called johndoe for sake of argument and this is the username and password that the Linux Sendmail box is using to autheticate to

So where I'm confused is when this Linux box gets mail from the crystal server whose ip address is the access database as allowed to relay - what the user sees in his mailbox is an email from johndoe.  in the old exchange days it would have come from the crystal servers name.

So how would I associate a gmail from-address in such a way that it would know that this email from the johndoe box is really from the crystal server and hence use the appropriate from address?


LVL 26

Expert Comment

ID: 34173348
Log into the gmail account for johndoe and "settings" and then "accounts and imports." The second option down should be "send mail as", you need to add the address that you want the mail to come from.
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Author Comment

ID: 34173444
OK I found that setting area, but it wants a valid email address.  What I have is for example is a internal windows server on a local domain that is using the linux box as a mail rely and then the Linux box sends to Gmail through the johndoe account.

What I don't understand is I have several multifunction devices that rely through this linux box and with these I can type any email address I choose in the from address and that's exactly what shows up in the gmail box.  So who's stripping off the from address from these servers? Sendmail or Google?

LVL 26

Accepted Solution

jar3817 earned 500 total points
ID: 34173570
Google is doing that. Think about it, google (or any other email service) will NEVER forward email with a bogus FROM address, it's just not going to happen. I'd suggest you create some valid email account for all your mutlifunction devices and have them sent via that address. or something like that.

Author Comment

ID: 34173678
Yes I see what you mean, in the old days with exchange and Verizon just holding our MX record we could get away with it - which explains why we got blacklisted a few times!!!

OK I will proceed down that path which is fine.

Thanks for the help.


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