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Thread: Can't send email (zimbra to gmail) - receive fine

  1. #1
    hellspawn is offline Member
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    Default Can't send email (zimbra to gmail) - receive fine

    I recently installed Zimbra 7.0.0 Beta3 on a Fedora 14 system. Receiving email from gmail seems to work ok, but sending email to gmail doesn't work. I think the problem may be with the way I setup DNS. I'm no expert on DNS, but here's my setup:

    The computer I'm installing zimbra onto is on a simple home network. Since my ISP can change my IP at any point, I use dyndns to assign a hostname to my IP which my router updates. My hostname is talz.mine.nu. The FQDN of the Fedora machine I instaled zimbra onto is fedora.talz.mine.nu (although this can only be resolved from inside my LAN). I told it during the installation to create a domain called talz.mine.nu and it complained that talz.mine.nu did not resolve to the IP of the Fedora box. I skipped the warning because I am forwarding port 25 from my router to the Fedora box, and talz.mine.nu resolves my router's IP so that should work OK (AFAIK).

    /var/log/maillog says things like:

    Code:
    Jan 21 19:15:18 fedora postfix/smtpd[30609]: connect from fedora.talz.mine.nu[192.168.1.119]
    Jan 21 19:15:18 fedora postfix/smtpd[30609]: 3FFF5A1965: client=fedora.talz.mine.nu[192.168.1.119]
    Jan 21 19:15:18 fedora postfix/cleanup[30612]: 3FFF5A1965: message-id=<2006099514.2.1295662518009.JavaMail.root@fedora.talz.mine.nu>
    Jan 21 19:15:18 fedora postfix/qmgr[30282]: 3FFF5A1965: from=<admin@talz.mine.nu>, size=601, nrcpt=1 (queue active)
    Jan 21 19:15:18 fedora postfix/smtpd[30609]: disconnect from fedora.talz.mine.nu[192.168.1.119]
    Jan 21 19:15:18 fedora postfix/smtpd[30616]: connect from localhost.localdomain[127.0.0.1]
    Jan 21 19:15:18 fedora postfix/smtpd[30616]: CE2E1A196A: client=localhost.localdomain[127.0.0.1]
    Jan 21 19:15:18 fedora postfix/cleanup[30612]: CE2E1A196A: message-id=<2006099514.2.1295662518009.JavaMail.root@fedora.talz.mine.nu>
    Jan 21 19:15:18 fedora postfix/qmgr[30282]: CE2E1A196A: from=<admin@talz.mine.nu>, size=1047, nrcpt=1 (queue active)
    Jan 21 19:15:18 fedora postfix/smtp[30613]: 3FFF5A1965: to=<test@gmail.com>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.63, delays=0.04/0.02/0.06/0.51, dsn=2.0.0, status=sent (250 2.0.0 Ok, id=29950-01, from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as CE2E1A196A)
    Jan 21 19:15:18 fedora postfix/qmgr[30282]: 3FFF5A1965: removed
    Jan 21 19:15:39 fedora postfix/smtp[30617]: connect to gmail-smtp-in.l.google.com[74.125.95.27]:25: Connection timed out
    Jan 21 19:16:01 fedora postfix/smtp[30617]: connect to alt1.gmail-smtp-in.l.google.com[74.125.157.27]:25: Connection timed out
    Jan 21 19:16:07 fedora zmmailboxdmgr[31021]: status requested
    Jan 21 19:16:07 fedora zmmailboxdmgr[31021]: status OK
    Jan 21 19:16:22 fedora postfix/smtp[30617]: connect to alt2.gmail-smtp-in.l.google.com[74.125.93.27]:25: Connection timed out
    Jan 21 19:16:43 fedora postfix/smtp[30617]: connect to alt3.gmail-smtp-in.l.google.com[209.85.227.27]:25: Connection timed out
    Jan 21 19:17:04 fedora postfix/smtp[30617]: connect to alt4.gmail-smtp-in.l.google.com[74.125.39.27]:25: Connection timed out
    Jan 21 19:17:04 fedora postfix/smtp[30617]: CE2E1A196A: to=<test@gmail.com>, relay=none, delay=105, delays=0.01/0.02/105/0, dsn=4.4.1, status=deferred (connect to alt4.gmail-smtp-in.l.google.com[74.125.39.27]:25: Connection timed out)
    Jan 21 19:18:07 fedora zmmailboxdmgr[31537]: status requested
    Jan 21 19:18:07 fedora zmmailboxdmgr[31537]: status OK
    Why are the timeouts happening? What did I do wrong?

  2. #2
    phoenix is online now Zimbra Consultant & Moderator
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    Quote Originally Posted by hellspawn View Post
    I recently installed Zimbra 7.0.0 Beta3 on a Fedora 14 system. Receiving email from gmail seems to work ok, but sending email to gmail doesn't work. I think the problem may be with the way I setup DNS. I'm no expert on DNS, but here's my setup:

    The computer I'm installing zimbra onto is on a simple home network. Since my ISP can change my IP at any point, I use dyndns to assign a hostname to my IP which my router updates. My hostname is talz.mine.nu. The FQDN of the Fedora machine I instaled zimbra onto is fedora.talz.mine.nu (although this can only be resolved from inside my LAN). I told it during the installation to create a domain called talz.mine.nu and it complained that talz.mine.nu did not resolve to the IP of the Fedora box. I skipped the warning because I am forwarding port 25 from my router to the Fedora box, and talz.mine.nu resolves my router's IP so that should work OK (AFAIK).

    /var/log/maillog says things like:

    Code:
    Jan 21 19:15:18 fedora postfix/smtpd[30609]: connect from fedora.talz.mine.nu[192.168.1.119]
    Jan 21 19:15:18 fedora postfix/smtpd[30609]: 3FFF5A1965: client=fedora.talz.mine.nu[192.168.1.119]
    Jan 21 19:15:18 fedora postfix/cleanup[30612]: 3FFF5A1965: message-id=<2006099514.2.1295662518009.JavaMail.root@fedora.talz.mine.nu>
    Jan 21 19:15:18 fedora postfix/qmgr[30282]: 3FFF5A1965: from=<admin@talz.mine.nu>, size=601, nrcpt=1 (queue active)
    Jan 21 19:15:18 fedora postfix/smtpd[30609]: disconnect from fedora.talz.mine.nu[192.168.1.119]
    Jan 21 19:15:18 fedora postfix/smtpd[30616]: connect from localhost.localdomain[127.0.0.1]
    Jan 21 19:15:18 fedora postfix/smtpd[30616]: CE2E1A196A: client=localhost.localdomain[127.0.0.1]
    Jan 21 19:15:18 fedora postfix/cleanup[30612]: CE2E1A196A: message-id=<2006099514.2.1295662518009.JavaMail.root@fedora.talz.mine.nu>
    Jan 21 19:15:18 fedora postfix/qmgr[30282]: CE2E1A196A: from=<admin@talz.mine.nu>, size=1047, nrcpt=1 (queue active)
    Jan 21 19:15:18 fedora postfix/smtp[30613]: 3FFF5A1965: to=<test@gmail.com>, relay=127.0.0.1[127.0.0.1]:10024, delay=0.63, delays=0.04/0.02/0.06/0.51, dsn=2.0.0, status=sent (250 2.0.0 Ok, id=29950-01, from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as CE2E1A196A)
    Jan 21 19:15:18 fedora postfix/qmgr[30282]: 3FFF5A1965: removed
    Jan 21 19:15:39 fedora postfix/smtp[30617]: connect to gmail-smtp-in.l.google.com[74.125.95.27]:25: Connection timed out
    Jan 21 19:16:01 fedora postfix/smtp[30617]: connect to alt1.gmail-smtp-in.l.google.com[74.125.157.27]:25: Connection timed out
    Jan 21 19:16:07 fedora zmmailboxdmgr[31021]: status requested
    Jan 21 19:16:07 fedora zmmailboxdmgr[31021]: status OK
    Jan 21 19:16:22 fedora postfix/smtp[30617]: connect to alt2.gmail-smtp-in.l.google.com[74.125.93.27]:25: Connection timed out
    Jan 21 19:16:43 fedora postfix/smtp[30617]: connect to alt3.gmail-smtp-in.l.google.com[209.85.227.27]:25: Connection timed out
    Jan 21 19:17:04 fedora postfix/smtp[30617]: connect to alt4.gmail-smtp-in.l.google.com[74.125.39.27]:25: Connection timed out
    Jan 21 19:17:04 fedora postfix/smtp[30617]: CE2E1A196A: to=<test@gmail.com>, relay=none, delay=105, delays=0.01/0.02/105/0, dsn=4.4.1, status=deferred (connect to alt4.gmail-smtp-in.l.google.com[74.125.39.27]:25: Connection timed out)
    Jan 21 19:18:07 fedora zmmailboxdmgr[31537]: status requested
    Jan 21 19:18:07 fedora zmmailboxdmgr[31537]: status OK
    Why are the timeouts happening? What did I do wrong?
    There's at least one problem with your configuration (possibly more), the item I've highlighted above measn that you're likely to have problems sending email to other servers (especially services like google & AOL) because you're on a dynamic DNS. A lot of mail server will reject those emails as they simply don't trust server that are on a dynamic DNS, lots of infected machines live there. You will need to relay your mail through another server (probably the mail server of your ISP).

    Another possible problem might be that you haven't set-up a Split DNS (plus a valiud /etc/hosts file) on your LAN, have you done that? If you haven't, you need to. Another item (two actually) you haven't mentioned is whether you have any firewall or NAT router that might be blocking outbound mail connections and/or your ISP might also be blocking outbound Port 25 connections if they don't allow you to host a mail server. You'll need to check all of those items.
    Regards


    Bill


    Acompli: A new adventure for Co-Founder KevinH.

  3. #3
    hellspawn is offline Member
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    Quote Originally Posted by phoenix View Post
    There's at least one problem with your configuration (possibly more), the item I've highlighted above measn that you're likely to have problems sending email to other servers (especially services like google & AOL) because you're on a dynamic DNS. A lot of mail server will reject those emails as they simply don't trust server that are on a dynamic DNS, lots of infected machines live there. You will need to relay your mail through another server (probably the mail server of your ISP).

    Another possible problem might be that you haven't set-up a Split DNS (plus a valiud /etc/hosts file) on your LAN, have you done that? If you haven't, you need to. Another item (two actually) you haven't mentioned is whether you have any firewall or NAT router that might be blocking outbound mail connections and/or your ISP might also be blocking outbound Port 25 connections if they don't allow you to host a mail server. You'll need to check all of those items.
    Thanks for the useful info. I didn't know dynamic DNS might be blacklisted by some email providers. What would I have to set up to relay mail through my ISP? Is it just filling out the "Relay MTA for external delivery" field in the Administration Console under Global Settings (MTA tab)? That seems like it should be it.

    While reading documents on how to setup Zimbra, I've also read the words Split DNS somewhere, but figured it was something unimportant. Turns out if I have a NAT router (which I do) I need to setup Split DNS. Thanks for the hint. Not sure how to do that yet but I'll read into that.

    My router blocks incoming connections, not outgoing ones. For incoming connections, I allowed port 25 through the router's firewall and made the router forward port 25 to the fedora machine. I also did a quick test on Open Port Check Tool, and it said port 25 was open, but I'm pretty sure that only checks inbound connections. Like you said, my ISP could still be blocking my outbound port 25. Would relaying mail through my ISP's mail server overcome the problem if my ISP is blocking outbound port 25? Or would Zimbra still need to use port 25 to send mail to the ISP's mail server?

    I also get a message when I'm on the "Server Statistics" tab of the Administration Console that says "This server is not an MTA and will not have any MTA stats." Is that a problem as well? Should my server be an MTA to be able to send out messages?

  4. #4
    phoenix is online now Zimbra Consultant & Moderator
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    Quote Originally Posted by hellspawn View Post
    Thanks for the useful info. I didn't know dynamic DNS might be blacklisted by some email providers.
    It's not dynDNS that gets blacklisted it's your IP address. Many mail servers check to see if you are on a dynamic IP and if you are then they will not accept mail from you.

    Quote Originally Posted by hellspawn View Post
    What would I have to set up to relay mail through my ISP? Is it just filling out the "Relay MTA for external delivery" field in the Administration Console under Global Settings (MTA tab)? That seems like it should be it.
    Yes, that's the correct location.

    Quote Originally Posted by hellspawn View Post
    While reading documents on how to setup Zimbra, I've also read the words Split DNS somewhere, but figured it was something unimportant. Turns out if I have a NAT router (which I do) I need to setup Split DNS. Thanks for the hint. Not sure how to do that yet but I'll read into that.
    Yes, you will need it behind the a NAT router, It's fairly straightforward if you install BIND and follow the article instructs and you can use the 'Verify...' section to check it's all OK.

    Quote Originally Posted by hellspawn View Post
    My router blocks incoming connections, not outgoing ones. For incoming connections, I allowed port 25 through the router's firewall and made the router forward port 25 to the fedora machine. I also did a quick test on Open Port Check Tool, and it said port 25 was open, but I'm pretty sure that only checks inbound connections.
    Inbound connections are not the problem as you're receiving email, it's the Outbound connection that's the likely problem.

    Quote Originally Posted by hellspawn View Post
    Like you said, my ISP could still be blocking my outbound port 25. Would relaying mail through my ISP's mail server overcome the problem if my ISP is blocking outbound port 25?
    Yes, that would solve the problem.

    Quote Originally Posted by hellspawn View Post
    Or would Zimbra still need to use port 25 to send mail to the ISP's mail server?
    All mail servers connect to each other by Port 25, that's a standard that doesn't change.

    Quote Originally Posted by hellspawn View Post
    I also get a message when I'm on the "Server Statistics" tab of the Administration Console that says "This server is not an MTA and will not have any MTA stats." Is that a problem as well? Should my server be an MTA to be able to send out messages?
    You should fix the other problems first, especially the hosts file and the DNS records and don't worry about this until after everything is set-up correctly.
    Regards


    Bill


    Acompli: A new adventure for Co-Founder KevinH.

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    hellspawn is offline Member
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    Quote Originally Posted by phoenix View Post
    It's not dynDNS that gets blacklisted it's your IP address. Many mail servers check to see if you are on a dynamic IP and if you are then they will not accept mail from you.

    Yes, that's the correct location.

    Yes, you will need it behind the a NAT router, It's fairly straightforward if you install BIND and follow the article instructs and you can use the 'Verify...' section to check it's all OK.

    Inbound connections are not the problem as you're receiving email, it's the Outbound connection that's the likely problem.

    Yes, that would solve the problem.

    All mail servers connect to each other by Port 25, that's a standard that doesn't change.

    You should fix the other problems first, especially the hosts file and the DNS records and don't worry about this until after everything is set-up correctly.
    Awesome. Thanks again for all the info. Time to get cracking...

  6. #6
    hellspawn is offline Member
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    I setup relay mail from my ISP and it started working again. I followed this guide:

    Outgoing SMTP Authentication - Zimbra :: Wiki

    After reading about split DNS, I realized what it was, but I didn't really have to do it. All I did was forward port 25 from my router to the fedora machine and it works great. Good thing too, since the router I use didn't look like it had an easy way to do split DNS - it could either do DNS to local network only or all networks (local and internet), but not split DNS.

    Thanks phoenix!

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