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Sophos SMTP Relay issues - Exchange

GZgidnick
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
  • 0
    Just created new certificate on the sophos using the FQDN: remote.innercomms.com
    The same FQDN is used as the SMTP hostname
    The same FQDN is used as the Exchange Smarthost.

    On the Sophos, Exchange has been removed from the Skip TLS List.
    I can relay messages from Exchange to Sophos successfully if the "Negotiate TLS authentication" is switched off for the Exchange send connector.

    As soon as I switch on  "Negotiate TLS authentication" on the send exchange connector, the messages are being queued, but now with different error message!

    2014-08-11T11:14:59.437Z,SophosRelay,08D182A1B8491BB8,0,,192.168.0.1:25,*,,attempting to connect
    2014-08-11T11:14:59.445Z,SophosRelay,08D182A1B8491BB8,1,192.168.0.30:7856,192.168.0.1:25,+,,
    2014-08-11T11:14:59.495Z,SophosRelay,08D182A1B8491BB8,2,192.168.0.30:7856,192.168.0.1:25,,EHLO exchange.innercomms.com,
    2014-08-11T11:14:59.505Z,SophosRelay,08D182A1B8491BB8,4,192.168.0.30:7856,192.168.0.1:25,,STARTTLS,
    2014-08-11T11:14:59.535Z,SophosRelay,08D182A1B8491BB8,11,192.168.0.30:7856,192.168.0.1:25,11T11:14:59.591Z,SophosRelay,08D182A1B8491BB8,14,192.168.0.30:7856,192.168.0.1:25,*,UntrustedRoot,Chain validation status
    2014-08-11T11:14:59.593Z,SophosRelay,08D182A1B8491BB8,15,192.168.0.30:7856,192.168.0.1:25,>,QUIT,
    2014-08-11T11:14:59.606Z,SophosRelay,08D182A1B8491BB8,16,192.168.0.30:7856,192.168.0.1:25,
Reply
  • 0
    Just created new certificate on the sophos using the FQDN: remote.innercomms.com
    The same FQDN is used as the SMTP hostname
    The same FQDN is used as the Exchange Smarthost.

    On the Sophos, Exchange has been removed from the Skip TLS List.
    I can relay messages from Exchange to Sophos successfully if the "Negotiate TLS authentication" is switched off for the Exchange send connector.

    As soon as I switch on  "Negotiate TLS authentication" on the send exchange connector, the messages are being queued, but now with different error message!

    2014-08-11T11:14:59.437Z,SophosRelay,08D182A1B8491BB8,0,,192.168.0.1:25,*,,attempting to connect
    2014-08-11T11:14:59.445Z,SophosRelay,08D182A1B8491BB8,1,192.168.0.30:7856,192.168.0.1:25,+,,
    2014-08-11T11:14:59.495Z,SophosRelay,08D182A1B8491BB8,2,192.168.0.30:7856,192.168.0.1:25,,EHLO exchange.innercomms.com,
    2014-08-11T11:14:59.505Z,SophosRelay,08D182A1B8491BB8,4,192.168.0.30:7856,192.168.0.1:25,,STARTTLS,
    2014-08-11T11:14:59.535Z,SophosRelay,08D182A1B8491BB8,11,192.168.0.30:7856,192.168.0.1:25,11T11:14:59.591Z,SophosRelay,08D182A1B8491BB8,14,192.168.0.30:7856,192.168.0.1:25,*,UntrustedRoot,Chain validation status
    2014-08-11T11:14:59.593Z,SophosRelay,08D182A1B8491BB8,15,192.168.0.30:7856,192.168.0.1:25,>,QUIT,
    2014-08-11T11:14:59.606Z,SophosRelay,08D182A1B8491BB8,16,192.168.0.30:7856,192.168.0.1:25,
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