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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
    Hi boys (Zdravo Vilic)

    Exactly as you said, I found the same error message in the Exchange logs
    #Software: Microsoft Exchange Server
    #Version: 14.0.0.0
    #Log-type: SMTP Send Protocol Log
    #Date: 2014-08-10T11:51:18.586Z
    #Fields: date-time,connector-id,session-id,sequence-number,local-endpoint,remote-endpoint,event,data,context
    2014-08-10T11:51:18.586Z,sophos relay,08D182A1B8491A83,0,,192.168.0.1:25,*,,attempting to connect
    2014-08-10T11:51:18.644Z,sophos relay,08D182A1B8491A83,1,192.168.0.30:30407,192.168.0.1:25,+,,
    2014-08-10T11:51:18.681Z,sophos relay,08D182A1B8491A83,2,192.168.0.30:30407,192.168.0.1:25,,EHLO exchange.*********.com,
    2014-08-10T11:51:18.684Z,sophos relay,08D182A1B8491A83,4,192.168.0.30:30407,192.168.0.1:25,,STARTTLS,
    2014-08-10T11:51:18.694Z,sophos relay,08D182A1B8491A83,11,192.168.0.30:30407,192.168.0.1:25,relay,08D182A1B8491A83,14,192.168.0.30:30407,192.168.0.1:25,*,SubjectMismatch,Chain validation status
    2014-08-10T11:51:19.041Z,sophos relay,08D182A1B8491A83,15,192.168.0.30:30407,192.168.0.1:25,>,QUIT,
    2014-08-10T11:51:19.044Z,sophos relay,08D182A1B8491A83,16,192.168.0.30:30407,192.168.0.1:25,
Reply
  • 0
    Hi boys (Zdravo Vilic)

    Exactly as you said, I found the same error message in the Exchange logs
    #Software: Microsoft Exchange Server
    #Version: 14.0.0.0
    #Log-type: SMTP Send Protocol Log
    #Date: 2014-08-10T11:51:18.586Z
    #Fields: date-time,connector-id,session-id,sequence-number,local-endpoint,remote-endpoint,event,data,context
    2014-08-10T11:51:18.586Z,sophos relay,08D182A1B8491A83,0,,192.168.0.1:25,*,,attempting to connect
    2014-08-10T11:51:18.644Z,sophos relay,08D182A1B8491A83,1,192.168.0.30:30407,192.168.0.1:25,+,,
    2014-08-10T11:51:18.681Z,sophos relay,08D182A1B8491A83,2,192.168.0.30:30407,192.168.0.1:25,,EHLO exchange.*********.com,
    2014-08-10T11:51:18.684Z,sophos relay,08D182A1B8491A83,4,192.168.0.30:30407,192.168.0.1:25,,STARTTLS,
    2014-08-10T11:51:18.694Z,sophos relay,08D182A1B8491A83,11,192.168.0.30:30407,192.168.0.1:25,relay,08D182A1B8491A83,14,192.168.0.30:30407,192.168.0.1:25,*,SubjectMismatch,Chain validation status
    2014-08-10T11:51:19.041Z,sophos relay,08D182A1B8491A83,15,192.168.0.30:30407,192.168.0.1:25,>,QUIT,
    2014-08-10T11:51:19.044Z,sophos relay,08D182A1B8491A83,16,192.168.0.30:30407,192.168.0.1:25,
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