Cannot Send Email Externally

[Charlesdita]

Good day,

I'm a rookie when it comes to Zimbra so please, bear with me.

I installed Zimbra 7.13 on my Ubuntu 10.04 LTS Server. It installed smoothly and was able to make Zimbra up and running. I also used split DNS (bind9) since my Zimbra server is behind a firewall (pFsense). I also added the needed port rules on pfsense in order to make the Zimbra server work. By the way, I'm using pFsense 2.0.

Here's the issue. I can send and receive emails internally. But when I try to send an email to Gmail or Yahoo, the mail stays on "Deferred" under Mail queues on the Zimbra admin page. Here is the error details:

Sender: sender@mydomain.com
From host: localhost.localdomain
From IP: 127.0.0.1
Recipients: receiver@gmail.com
To domain: gmail.com
Content filter:
Size: 1108
Reason: connect to alt4.gmail-smtp-in.l.google.com[74.125.115.26]:25: connection timed out.

Please take note that I edited the email addresses and domain in the error message for security purposes.

I hope someone can help me with this issue.

Thank you in advance!

Cheers!

[vavai]

Originally Posted by Charlesdita

Good day,

Reason: connect to alt4.gmail-smtp-in.l.google.com[74.125.115.26]:25: connection timed out.

Please take note that I edited the email addresses and domain in the error message for security purposes.

I hope someone can help me with this issue.

Thank you in advance!

Cheers!

It seems that your problem came from your Firewall setting. Pfsense blocked port 25 as noticed on your error message.

Port 25 required for communication between mail server (in your case, between Zimbra and Gmail).

Use telnet for testing whether your port blocked by firewall or not, something like :

telnet vavai.com 25

If your firewall does not block port 25 as well, the above command will display the following message :

telnet vavai.com 25
Trying 174.120.9.9...
Connected to vavai.com.
Escape character is '^]'.
220-terraza.websitewelcome.com ESMTP Exim 4.69 #1 Fri, 16 Dec 2011 21:23:12 -0600
220-We do not authorize the use of this system to transport unsolicited,
220 and/or bulk e-mail.

Note : You may replace vavai.com with any mail server outside your network, vavai.com was only a test domain.

[jgg]

Hi all.

I have the same problem, but I think that MTA or DNS don't be doing the MX search for send mails.

When I see logs file, I found that the MTA is trying to connect with server Web IP address, but not to the MailExchange server.

Example:

Dec 17 09:13:13 epa postfix/qmgr[4989]: BE05B2CC422: from=<user@dominio.com>, size=995, nrcpt=1 (queue active)
Dec 17 09:13:13 epa postfix/smtp[13000]: 0D0A82CC420: to=<usuario@hotmail.com>, relay=127.0.0.1[127.0.0.1]:10024, delay=1.8, delays=0.13/0.02/0.09/1.6, dsn=2.0.0, status=sent (250 2.0.0 from MTA([127.0.0.1]:10025): 250 2.0.0 Ok: queued as BE05B2CC422)
Dec 17 09:13:13 epa postfix/qmgr[4989]: 0D0A82CC420: removed
Dec 17 09:13:34 epa postfix/smtp[13004]: connect to hotmail.com[65.55.72.135]:25: Connection timed out
This is the Hotmail Web Server IP Address, Not MX
Dec 17 09:13:55 epa postfix/smtp[13004]: connect to hotmail.com[65.55.72.151]:25: Connection timed out



Any idea about why the MTA or DNS don't look for a MX register?

[vavai]

Hi Jgg,

Originally Posted by jgg

Hi all.
Dec 17 09:13:55 epa postfix/smtp[13004]: connect to hotmail.com[65.55.72.151]:25: Connection timed out

Any idea about why the MTA or DNS don't look for a MX register?

Hmmh, it seems that you have leave Enable DNS lookups options unchecked on Zimbra Admin | Global Settings | MTA or Zimbra Admin | Server Settings | MTA so Zimbra didn't looking for MX records and use the domain as target server instead .

Please check the option (means Enable DNS lookups=Yes) and then restart your Zimbra services.

[jgg]

Thanks a lot !!!!
I cheked the option, and that's all, everything is OK !!!

Thanks dude !!!

[Charlesdita]

@vavai

Thanks! I will try that and I will give you an update about the steps that you suggested.