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Sophos SMTP Relay issues - Exchange

Hi guys, 

Me, back with another thread.

My small lab is growing steadily recently with Sophos taking the lead.

I use the Sophos as SMTP Relay for Exchange 2010.

The Sophos is setup:
Routing > Allowed domain
Routing by static host > Exchange
Hostbased Relay > Exchange 
Authenticated relay > Username (defined in sophos)
SMTP hostname > Sophos FQDN
Dataprotection, Antispam and Antivirus tweaked as needed.

The Exchange:
Hub trunsport > Custom
Route Mail > *
Smart Host > IP.SO.PH.OS
Basic TLS Auth > Username (defined in sophos)

I've been able to route emails with the current setup until recently updated the certificate on the Exchange.

No from the Sophos SMTP live logs I am getting:
2014:08:09-01:10:15 remote exim-in[5175]: 2014-08-09 01:10:15 exim 4.76 daemon started: pid=5175, no queue runs, listening for SMTP on port 25 (IPv4) port 587 (IPv4) and for SMTPS on port 465 (IPv4)
2014:08:09-01:10:47 remote exim-in[5175]: 2014-08-09 01:10:47 SMTP connection from [192.168.0.30]:18030 (TCP/IP connection count = 1)
2014:08:09-01:10:47 remote exim-in[11483]: 2014-08-09 01:10:47 SMTP connection from [192.168.0.30]:18030 closed by QUIT

And from the Exchange logs, for the queued emails I am getting:
The last attempt to send the message was at 8/9/2014 12:57:29 AM (UTC+10:00) Canberra, Melbourne, Sydney and generated the error '451 4.4.0 Primary target IP address responded with: "454 4.7.5 Certificate validation failure." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts.'.

Reseting Sophos/Exchange didn't help. Exchange works fine without relay and/or without TLS authentication.

Why did the Sophos broke? I never installed/accepted SSL cert on the Sophos....


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Parents
  • Is there really over 13 minutes difference in the clocks, or are the SMTP lines from a different conversation?

    There must be a problem with the new Exchange cert, but I can't guess what that might be from the data presented.

    Cheers - Bob
     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
Reply
  • Is there really over 13 minutes difference in the clocks, or are the SMTP lines from a different conversation?

    There must be a problem with the new Exchange cert, but I can't guess what that might be from the data presented.

    Cheers - Bob
     
    Sophos UTM Community Moderator
    Sophos Certified Architect - UTM
    Sophos Certified Engineer - XG
    Gold Solution Partner since 2005
    MediaSoft, Inc. USA
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