Sendmail is one of those applications that can do just about anything (as long as you know the secret handshake that gets you access to detailed information about it’s configuration).

I’ve been using it for about 1 year to allow my company’s website to send email to our users.  To avoid all the headaches involved in making sure our emails don’t get rejected as spam, we use googlemail as a smart host since they host our email accounts for our domain.

This has been working great, but recently we ran into a limitation that would be a deal breaker if it couldn’t be solved.

The Problem:

  1. When using googlemail as your smart host, you must use authentication and Google rewrites the from address of all your emails to the user’s email address that you use to authenticate.  Thus, if you authenticate with webmaster@example.com’s credentials, all email from your server will seem to come from webmaster@example.com.  Even if you specify a different sender!
  2. When sendmail is configured to use a smart host that requires authentication (like googlemail), it chooses the authentication credentials based on the host name or IP address of the smart host.  So, unless you use multiple smart hosts, sendmail will only use 1 set of authentication credentials when connecting to the smart host.
  3. We are now hosting 2 websites on the same server with completely different domain names that each need to send email from different addresses that belong to their respective domains.

When you combine all three parts, the problem becomes clear:

How do I send email from info@yyy.com when sendmail will always use info@zzz.com’s credentials for smart host authentication, thus making Google rewrite the from address so that all email from my server appears to come from info@zzz.com?

The Solution:

To me, the best solution would be for sendmail to choose smart host authentication credentials based on the sender address of each email.

For example:

  1. Sendmail receives an email message to deliver from info@yyy.com
  2. Instead of looking up “smtp.googlemail.com” in authinfo, it looks up “info@yyy.com”

Seems simple enough, but, after hours of searching the web, I found that sendmail is just plain not configured to do this.

However, everything it needs to be able to do this is already available, it just doesn’t use it.  So I decided to make sendmail use it by editing the sendmail.cf file.

I know, I know, I’m supposed to use sendmail.mc, but darn it all if I wasn’t able to get this to work using the macro file.

So, without further ado, here’s what I did to make sendmail behave the way I wanted it to.

The How To:

Assumptions:

I’m assuming that you already have sendmail configured to use a smart host that requires authentication.  It is beyond the scope of this document to cover that.

Instructions:

1) Edit the authinfo section of sendmail.cf so that it looks like this:

######################################
### authinfo: lookup authinfo in the access map
###
###     Parameters:
###             $0: {f}
###             $1: {server_name}
###             $2: {server_addr}
######################################
Sauthinfo
R$*        $: <$(authinfo AuthInfo:$&{f} $: ? $)>
R<?>      $: <$(authinfo AuthInfo:$&{server_name} $: ? $)>
R<?>      $: <$(authinfo AuthInfo:$&{server_addr} $: ? $)>
R<?>      $: <$(authinfo AuthInfo: $: ? $)>
R<?>      $@ no                      no authinfo available
R<$*>    $# $1

The key here is the $&{f} macro.  In sendmail, it stands for the sender’s address from the envelope of the email.

The above code tells sendmail to look for entries in the authinfo file that match the sender’s email address.  If no match is found, then check for entries that match the smart host’s name/IP.

In effect, this preserves sendmail’s original behavior as the fall back if no match is found in the authinfo file for the sender’s address.

2) Add sender credentials to the authinfo file (its location is defined by the authinfo feature in sendmail.mc):

AuthInfo:info@ex.com “U:info@ex.com” “P:xx” “M:PLAIN”
AuthInfo:info@yyy.com “U:info@yyy.com” “P:xx” “M:PLAIN”
AuthInfo:info@zzz.com “U:info@zzz.com” “P:xx” “M:PLAIN”
AuthInfo:smtp.sh.com “U:info@ex.com” “P:xx” “M:PLAIN”
AuthInfo: “U:info@ex.com” “P:xx” “M:PLAIN”

In the example above, the first 3 entries are credentials for different senders that use the server to send email (they take advantage of the changes we made in step 1).  The last 2 entries are the original smart host authentication configuration which ensures that sendmail will still be able to connect to the smart host and send the email using a default set of credentials, even if the sender’s address does not match any of the other entries.

3) Remake the authinfo database using the “makemap” command.

4) Make sure to comment out any lines in your init script for sendmail that recompile sendmail.cf using the sendmail.mc script.  The location of this file on Redhat variants is: /etc/init.d/sendmail

(if you don’t do this, your changes to sendmail.cf will be lost when you restart sendmail!)

5) Restart sendmail.

You should now be able to control which user’s credentials are used to authenticate with the smart host on a case by case basis by changing the sender’s address on the email.

This is specified using the -f flag when calling sendmail on the command line (like PHP’s mail() function does).

Final Thoughts:

While this gets the job done, it would be nice to be able to incorporate the changes in step 1 into the sendmail.mc file.  This would make it much easier to maintain since anyone who runs the “make” command on the /etc/mail directory will destroy the changes we made to sendmail.cf in step 1.