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Certificate Error When Connecting to SMTP Relay on Astaro

JBoslooper
Hello,

This is a small item but can't seem to find anything about it here in the forums.  

I am using Outlook 2007 to retrieve mail from a mail server at work using IMAP to Retrieve and SMTP to send.  

The mail server is behind the Astaro and the Astaro is intercepting the SMTP traffic.  When I attempt to send a message from Outlook through that account, I recieve a certificate error stating (See Attachment Also):

"The server you are connected to is using a security certificate that cannot be verified.

The target principal name is incorrect."

I can click YES or NO and I am able to continue sending the message replayed through the Astaro but this is still not right.  

Originally the certificate said that it was not part of a trusted root CA therefore I imported into my machine which now, when viewing the certificate, it says its ok, but I still get the same certificate error when sending (relaying) a message through the astaro.

I have attached screen shots of the error message and certificate in question.

Any ideas?

Thanks.

-John


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  • 0
    John,

    OK, I guess I'm just a little confused that you would not configure Outlook to connect with the Exchange server as an "Exchange Server" instead of an IMAP/SMTP host; I'll guess your Exchange server is not new enough to offer RPC over HTTP, and that you don't want to have to connect via VPN first.

    Another guess is that if you're connected internally or via VPN, you don't get the cert warning.  If that's the case, I also would like to learn of a work-around for recognizing a cert regardless of the IP you access - 'Internal (Address)' when inside, and 'External (Address)' when outside.

    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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  • 0
    John,

    OK, I guess I'm just a little confused that you would not configure Outlook to connect with the Exchange server as an "Exchange Server" instead of an IMAP/SMTP host; I'll guess your Exchange server is not new enough to offer RPC over HTTP, and that you don't want to have to connect via VPN first.

    Another guess is that if you're connected internally or via VPN, you don't get the cert warning.  If that's the case, I also would like to learn of a work-around for recognizing a cert regardless of the IP you access - 'Internal (Address)' when inside, and 'External (Address)' when outside.

    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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