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Thread: [SOLVED] Exchange and Zimbra behind NAT

  1. #1
    bryan08 is offline Member
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    Default [SOLVED] Exchange and Zimbra behind NAT

    We have Zimbra 5.05_GA on Ubuntu 6.06 LTS running great on our network with Exchange Server 2007. One problem that I am having is that when I send email from Zimbra to Exchange account, the email gets deferred.
    Zimbra local ip : 192.168.0.111
    Exchange local ip: 192.168.0.118
    I have already setup internal dns server.

    The error under /var/log/zimbra.log shows
    Jun 5 15:59:09 localhost postfix/smtp[28543]: 609964582C1: to=, relay=none, delay=19560, delays=19522/0/38/0, dsn=4.4.1, status=deferred (connect to mail.exchangedomain.org[xx.xx.xx.xx]: Connection timed out)

    xx.xx.xx.xx = external ip
    dig mail.exchangedomain.org gives external ip.
    I also updated /etc/hosts
    127.0.0.1 localhost.localdomain localhost
    192.168.0.111 mail.zimbradomain.org
    192.168.0.118 mail.exchangedomain.org

    I don't want to disable the dns lookups as we need to send external emails.
    I would appreciate if someone can point me in the right direction.
    Thank you in advance.
    Last edited by bryan08; 06-05-2008 at 05:24 PM.

  2. #2
    phoenix is online now Zimbra Consultant & Moderator
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    Have you set-up a Split Domain for this configuration? You will need that for correct routing of email.

    You also need to remove the entry in your /etc/hosts file for the exchange server, it's not needed.
    Regards


    Bill


    Acompli: A new adventure for Co-Founder KevinH.

  3. #3
    bryan08 is offline Member
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    Thank you for your prompt response. I think I forgot to say this. The Exchange and Zimbra has its own external ip web address, MX and A values. We are not trying to make Zimbra as our primary or secondary email server. Some of our users need to able to email users on exchange server.
    $ zmprov md exchangedomain.org zimbraMailCatchAllAddress @exchangedomain.org
    ERROR: account.NO_SUCH_DOMAIN (no_such_domain: exchangedomain.org)

  4. #4
    Bill Brock is offline Outstanding Member
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    Adding the LAN IP's of the servers to the other one's HOSTS file may solve your problem After doing so, each machine will resolve to the other using the entry in the HOSTS file and not the DNS server. By default, most operating systems will check the HOSTS file before checking their assigned DNS server. This can be changed of course but it is usually the default configuration.

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    bryan08 is offline Member
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    My /etc/hosts file looks like this
    127.0.0.1 localhost.localdomain localhost
    192.168.0.111 mail.zimbradomain.org mail
    192.168.0.118 mail.exchangedomain.org

    /etc/host.conf
    order hosts,bind
    multi on

    I am still getting this error message under /var/log/syslog
    Jun 5 15:59:09 localhost postfix/smtp[28543]: 609964582C1: to=, relay=none, delay=19560, delays=19522/0/38/0, dsn=4.4.1, status=deferred (connect to mail.exchangedomain.org[xx.xx.xx.xx]: Connection timed out)
    where xx.xx.xx.xx = external ip
    Also, hosts file is updated on the exchange server.
    192.168.0.111 mail.zimbradomain.org

  6. #6
    Bill Brock is offline Outstanding Member
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    If you ping mail.exchangedomain.org on the machine with the error what IP does it ping.

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    bryan08 is offline Member
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    It pings with external ip and there is no reply.

  8. #8
    Bill Brock is offline Outstanding Member
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    It should be resolving to what is in the HOSTS file. Very odd. I know in Windows there is no need to reboot after changing the HOSTS file. Don't know about Linux.

  9. #9
    phoenix is online now Zimbra Consultant & Moderator
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    Quote Originally Posted by bryan08 View Post
    It pings with external ip and there is no reply.
    That would explain your problem. From the ZImbra server try a dig:

    Code:
    dig exchangedomain.org mx
    dig exchangedomain.org any
    and see what response you get.
    Last edited by phoenix; 06-06-2008 at 11:04 PM.
    Regards


    Bill


    Acompli: A new adventure for Co-Founder KevinH.

  10. #10
    bryan08 is offline Member
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    I get:
    dig: '.exchangedomain.org' is not a legal name (empty label)

    I don't understand why it's not taking the local ip from hosts file. Do I have to edit route file or anything? Appreciate your help, Bill.

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