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Unable to use Snow Leopard SMTP mail service with Postini

3637 Views 8 Replies Latest reply: Nov 3, 2009 4:06 AM by pterobyte RSS
Paul Derby Level 1 Level 1 (115 points)
Currently Being Moderated
Nov 2, 2009 8:11 AM
After giving up on doing an upgrade from OS X Server 10.5.6 to 10.6.1, I bought a second Mini with Snow Leopard Server installed and am configuring it to eventually replace the 10.5.6 server.

I have email working just fine, except that when I change the delivery address in Postini from the Leopard server host name to the Snow Leopard Server host name, my incoming mail gets "bounced" due to too many hops.

If I change the delivery address back to the Leopard server host name, everything works just fine.

Here is the SMTP log from Snow Leopard:

Nov 2 10:38:32 testserve postfix/smtp[62796]: DFF1D4FA90: to=<>,[]:25, delay=1.9, delays=0/0.01/0.39/1.5, dsn=5.0.0, status=bounced (host[] said: 554 Too many hops - psmtp (in reply to end of DATA command))
Nov 2 10:38:32 testserve postfix/cleanup[62802]: C6D134FA93: message-id=<>

Several postings in various groups indicated this could be due to MX record problems resulting in looping. I changed the Postini destination address from the domain name to the Snow Leopard IP address and get the same bounce due to too many hops.

A DIG on the MX records for the host name of the Snow Leopard Server looks just fine.

The DNS records that I have on both servers and on zoneedit look just fine.

I checked both Postfix config files and I don't see anything that would cause problems. I think the bounce is coming from Postini, not from the Snow Leopard Server.... but not sure since Postini is logging to the SMTP log on the Snow Leopard Server.

Anyone else experiencing this same problem using Postini for SPAM filtering ahead of mail deliver?

Any ideas on how to resolve this problems would be appreciated.

Message was edited by: Paul Derby
Two Mac Mini's running OS X Server, Mac OS X (10.6.1)
  • pterobyte Level 6 Level 6 (10,910 points)
    Sounds like your message is being bounced back and forth between postini and your server. Most likely because your mail server does not think it is responsible for mail to your domain/user.

    First thing to check is that your mail server does accept mail for the mail addresses needed. Try and send local mail or change the mx record to point to your mail server directly.

    Once it does work locally and if you still have issues, please post the output of postconf -n of your server.

    Message was edited by: pterobyte
    Mac OS X (10.6.1)
  • Camelot Level 8 Level 8 (45,670 points)
    The problem is clearly:

    mydestination = $myhostname, localhost.$mydomain, localhost

    So your server isn't set to only accept mail addressed to,, or username@localhost

    This is the default setup in Snow Leopard Mail Server. You need to add '' as an additional domain that your mail server accepts mail for (Server Admin -> Mail -> Advanced -> Hosting -> Local Host Aliases.

    This is the field that tells postfix what domains to accept mail for.
    Mac OS X (10.5.6)
  • pterobyte Level 6 Level 6 (10,910 points)
    According to the output of postconf -n, your mail server is not set to accept mail for You need to add to the local host aliases in Server Admin (or add it to mydestination in

    Also, I would not recommend having external IPs in mynetworks unless absolutely necessary. I didn't check the IPs, but I would think you also added Postini's IP. This is why mail to your server for was not rejected, but since it is not a final destination for your domain, your server tried to deliver back to Postini (as per the MX records).

    You should also disable greylisting since you have mail filtered by Postini already.


    P.S. Camelot was faster

    Message was edited by: pterobyte
    Mac OS X (10.6.1)
  • Camelot Level 8 Level 8 (45,670 points)
    It would seem reasonable to me that Snow Leopard would default to generating a config file with your domain name already added to the local host aliases...

    I thought that too, at first, but have since changed my thinking...

    While this might seem to make sense at one level, you can get into a lot of trouble setting up a mail server without thinking about all the parts and pieces. Spam filters, relay rules, quotas, authentication etc. all need to be setup before your mail server is ready, and everyone's settings are going to be different.

    Therefore, since you have to go through additional steps anyway before you can run your own mail server it doesn't hurt to include setting the domain name as one of those steps.

    By setting the mail server to only accept a specific set of hostnames by default you can test your mail environment safely before opening it up to the wide world.

    I have no idea if that was the thinking behind the Snow Leopard's developer teams, but it seems reasonable.
    Mac OS X (10.5.6)
  • pterobyte Level 6 Level 6 (10,910 points)
    Actually, I think Apple has made it quite easy to include the server's domain name. There's even a checkbox "Include server's domain as local host alias" above the list of local host aliases in Server Admin.
    Mac OS X (10.6.1)


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