View Full Version : Advanced Snow Leopard Server Mail Problem

22nd December 2010, 11:15 AM
I run my own server. I like doing this, because it means I don't have to trust Google to not be evil, or have to change my email address every time I move house. It's an ideological thing, and I accept the occasional pain involved in doing so.

So, until last week I had a retail version of Leopard running on a Mac Mini with custom installations of Postfix and Courier-IMAP handling my family's email needs. This was working fine, but was in need of serious upgrading, and security hole closing. I didn't have a backup machine to use while I upgraded, but it had been on my to do list for a while. I'd been attracted by the new Mac Mini Servers for some time, and finally took the plunge. This is my first experience with Mac OS X server.

The set up was a breeze, and everything seemed to be working on Saturday, and I thought, great that was easy. Except it wasn't. Mail continues to be a problem, and tonight I'm going to swap back to my old server.

The Issue:
Some mail is not being delivered to my users. I've never had a problem like this before. In my experience, it is usually all or nothing. Only some getting through seems strange.

All mail sent by my users to the outside world is delivered correctly.
Not all mail sent to my users from the outside world is delivered correctly.

There are three outside mail servers I, or my users, have access to that seem to deliver fine: Immigration Department's mail server, my work's mail server and Apple's Cocoa dev list mail server. All others seem to just get lost.

What I see in the log with maximum logging:
connection from [IP Address]
lost connection from [IP Address]

Sometimes there will be a "connection lost after EHLO/HELO" in between, but not always. There is never a reason given for the connection problem.

If any of the three working mail servers are used, then there are no problems, and the logs look like you'd expect.

My set up in Server Admin is pretty standard. I've got ports 25 (SMTP [receiving]), 587 (SSL-SMTP [sending]), and 993 (SSL-IMAP) open. There is no problem retrieving mail which I copied over from my old server (and set correct permissions for) once users had been created.

I called Apple support, as I'm clearly within the 90 days help period. They suggested turning off Junk mail filtering. I did that, and also virus and all other kinds of filtering, but it seems to have made no difference.

When I called back this morning, they suggested it might be a missing PTR record in my DNS settings. I'm very sceptical of this, as the setup worked fine previously and the only thing that has changed is the server itself. They also said they weren't prepared to offer much more help, as internal mail was working fine.

I've Googled a great deal on this issue, but haven't turned up anything promising. If I can't figure this out, I plan to nuke Snow Leopard Server and use a retail version of Mac OS X and a custom compile of Postfix/Dovecot instead.

Help me MacTalk, you're my only hope!

24th December 2010, 11:42 AM
I'm pretty sure this turned out to be a SSL problem. I buggered up my Snow Leopard Server install trying to fix it, but feedback I've gotten from people trying to send me mail strongly suggests SSL.

Hopefully I can be up and running again after the Christmas break, and a clean install of Snow Leopard Server.