Using zimbra to relay from apache

[ASC]

Firstly I apologize if this is covered somewhere but my searching has left me without much help.

There are a couple of things going on here I'd love to get some help with, so please chime in if you can't point me in the right direction on any one of them.

Zimbra is configured and working fine for direct user mailboxes send/recieving. It is nat'd in a DMZ with the split dns config for hosting 2 mail domains, and eventually even more. I'm running my own nameservers with a business line so no ports are blocked via ISP, etc. Zimbra itself does not need to relay via an ISP, and is not configured to do so.

What I want to do is take my apache web server and relay mail from PHP apps via the zimbra mail server. I have configured zimbra to allow unauthenticated smtp relay's from the web server's IP.

1. To accomplish this I've configured sendmail on the web server and set zimbra as it's smart host so it can relay any and all mail to zimbra.

2. When mail from php apps go to zimbra based mailboxes it simply never shows up. A cat and grep of zimbralog and maillog seem to suggest it never even made it there... however

3. When mail from php apps go to external mailboxes they show up there but do not include 'mailed-by' headers that zimbra tags for for normal user accounts and appear in junk folders.

There's obviously a lot at play here and I'm not even sure Zimbra is the issue, but it seemed the most logical place to start. Obviously a solution is what I'm after but any help in locating some logs for more details on what's going on behind the scenes would help too.

Is there a message tracking in ZCS 6 that would help to confirm if these emails are actually being relayed by Zimbra or if apache/sendmail on the web server is somehow making it out on its own?

The Zimbra server CentOS install is 5.4 with nothing else but default packages and Zimbra on it... anybody know if there's something built in that could be catching the 'spam' from apache before it reaches Zimbra for the mails destined for zimbra based mailboxes? I've set kill percentage to 0 and the mails still don't ever seem to make it... even to junk mail folders.

Does the mailed-by header typically get excluded when zimbra is relaying for other hosts? All zimbra based mails don't get flagged as junk by external hosts, just the apache relayed ones do. I think the headers being different may be at least part of the reason for that.

Thanks in advance.

[phoenix]

Have you looked in the log files to see if any connection attempt is being made or the mail is being rejected?

[ASC]

Thank you for your response. I actually figured part of this out as I was summarizing everything for my initial post I had a realization of sorts.

Yes I did look over the log files in zimbra and didn't see anything at all.

Nothing at all in the zimbra logs of any kind... perhaps sendmail was somehow managing to get mail out on it's own. So I reviewed my sendmail config on the web server another time and I had configured everything correctly but left a dnl in front of my smart host config line... d'oh.

Sendmail somehow had enough info to try and force out the e-mail on its own, it used dns instead of hosts to resolve zimbra's public mail IP, which is natted on the same subnet so it couldn't access the zimbra server at all. Thus the mail never got delivered or attempted to deliver outside the web server itself. This whole setup is new to me so I overlooked a simple thing :/ That explains why mail sent to zimbra just vanished, and mail to external domains worked ok.

Now that the smart host is configured correctly, uncommented, and against an internal DNS record mail is reaching the zimbra server just fine. Zimbra is also routing mail to external domains correctly, but there is still an absence of 'mailed-by' headers which causes a spam flag to be triggered by many mail servers. Is there any way to have zimbra append that to unauthenticated smtp relay users?