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Why Sophos UTM not sending emails out

Mohamed Hassan

Hello Guys. Few days ago I had an issue with my internet resulted in changing my static IP. No since I've received a new IP I've updated my external DNS. 

However since my IP has changed I no longer able to send out emails from my UTM. I have mailenable which is relaying to UTM. From logs I can see UTM accepts relaying from my mailenable server but emails get spooled and see this in the logs:

 

2019:02:28-22:14:00 sukafun-utm smtpd[5343]: MASTER[5343]: Action: Forcing delivery process for 1gzMQI-000BCR-0t
2019:02:28-22:15:00 sukafun-utm exim-out[43216]: 2019-02-28 22:15:00 Start queue run: pid=43216
2019:02:28-22:16:19 sukafun-utm exim-out[41492]: 2019-02-28 22:16:19 1gzJxs-0007Mg-Dl SSL_write: (from [192.168.7.77]:999) syscall: Connection timed out
2019:02:28-22:16:19 sukafun-utm exim-out[41492]: 2019-02-28 22:16:19 1gzJxs-0007Mg-Dl SSL_write error 5
2019:02:28-22:16:19 sukafun-utm exim-out[41492]: 2019-02-28 22:16:19 1gzJxs-0007Mg-Dl SMTP timeout while connected to mail-tester.com [94.23.206.89] after sending data block (25910 bytes written): Connection timed out
2019:02:28-22:16:19 sukafun-utm exim-out[41491]: 2019-02-28 22:16:19 1gzJxs-0007Mg-Dl == test-3tjbp@mail-tester.com R=dnslookup T=remote_smtp defer (110): Connection timed out: SMTP timeout while connected to mail-tester.com [94.23.206.89] after sending data block (25910 bytes written)
2019:02:28-22:16:20 sukafun-utm exim-out[43418]: 2019-02-28 22:16:20 1gzKXM-0008JN-HK == test-37cxi@mail-tester.com R=dnslookup T=remote_smtp defer (-53): retry time not reached for any host
2019:02:28-22:16:20 sukafun-utm exim-out[43422]: 2019-02-28 22:16:20 1gzKP8-00083Z-Gr == test-37cxi@mail-tester.com R=dnslookup T=remote_smtp defer (-53): retry time not reached for any host
2019:02:28-22:16:20 sukafun-utm exim-out[40075]: 2019-02-28 22:16:20 End queue run: pid=40075
 
 
It lets me send emails out to some domains like gmail but most of other domains not. I confirm that my ISP not blocking port 25. My UTM is connected to internet. My external DNS is correct. Tried enabling smarthost from UTM but same issue. What else should I look for? 
I receive emails fine.
 
 
Cheers
Mo


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  • 0 in reply to Mohamed Hassan

    I've just tried something. Used my mail server to send directly without relying to UTM and email sent out fine. What do you think should I check in UTM?

    I've not changed anything in the UTM for awhile no idea why it would break and even if something would break I would assume incoming not outgoing.

  • 0 in reply to Mohamed Hassan

    You mnetioned you could send to gmail, but not hotmail, 365 etc

    When you did your test (without the UTM) did mail get to hotmail, 365 as opposed to when it's going via the UTM, it can't get to them?

  • 0 in reply to Mohamed Hassan

    When you IP changed did you delete and recreate the WAN interface or just edit it?

    Respectfully, 

     

    Badrobot

     

  • 0 in reply to Louis-M

    Yes email goes out directly from my mailenable mail server if using UTM it doesn't

  • 0 in reply to Badrobot

    Did not edit the WAN interface even. It's set to PPPoE and dynamically getting an IP from my ISP.

    What I've done is I created a new interface using another physical card using PPPoE and same results. 

    But

    When I used WAN to be an ethernet hooked up to a 4G modem so different IP and connection obviously it did work. Any idea why UTM doesn't like my normal VDSL connection when sending out emails where sending without UTM is fine. 

  • 0 in reply to Mohamed Hassan

    Obviously, you are at the point that you need someone to lay eyes on your configuration.   

    Since you are running a mail server, I am assuming that you are not a home user.   Do you have access to support?

  • 0 in reply to DouglasFoster

    My configuration is correct as it was working before and it did work when I switched to 4G interface.

    For now I'm going to try Sophos XG and see what it has got for mail protection as well as web. Do you recommend it?

  • 0 in reply to Mohamed Hassan

    Just a comment here (and not pointing the finger at the actual issue) but I would imagine you would have issues with sending mail from a mail server via 4G. I'm not aware of any providers who actually give out static IP's on 4G networks (in the UK at least). Mail servers coming from dynamic IP ranges will suffer from connectivity issues with regards to mail.

    You may also be suffering from the reputation of the IP address you are sending from and this may need built up over time. you can check here:

    https://www.senderscore.org/

  • 0 in reply to Louis-M

    Let me rephrase. My VDSL connection which has static IP is having the issue with sending out emails. When I connect my 4G test router to Sophos through ethernet emails go out. I'm talking about outgoing not incoming emails.

    If I don't relay on Sophos and send out from my mail server directly emails go out fine (on VDSL connection).

    I'm not relaying to Sophos now and will give it some time for reputation to build up on new IP address then will try relaying to Sophos. I guess that's my only option. 

  • 0 in reply to Mohamed Hassan

    There has to be a configuration error.   The timeout indicates a delivery problem, not a traffic rejection problem.   The delivery problem implies a routing problem or a traffic filter.   If it was a rejection problem, the sending hardware would not matter.

    Does UTM connect directly to the Internet, or is there a home router in the configuration?   If you have another firewall, maybe there is a configuration problem on it.

    Reboot your UTM.  That step has fixed a variety of strange unexplained problems for other users in this forum.

    Check all of your SNAT/NAT/DNAT rules, there may be one that was not updated for the new IP address.

    Disable Country Blocking, to see if that has an effect.

    Check ALL (30 or so) of your UTM logs, looking for clues.

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