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Setup SMTP via TLS on SBS 2003 for single outside domain

Posted on 2010-03-29
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Last Modified: 2013-11-30
I am trying to setup secure email from my server to a single external domain.  I have done much reading on this, but cannot successfully configure it.  Here are the steps:
1. Purchase a valid cert from a CA (GoDaddy)
2. Create VS and connector, configured for TLS and Address Space of TLSdomain.com
3. Apply cert to VS
4. Set Default Connector to cost 2 and new TLS connector to cost 1

I get the following error:
A configuration error in the e-mail system caused the message to bounce between two servers or to be forwarded between two recipients. Contact your administrator.
  <mydomain.com #5.3.5>

I am not sure I have configured the VS and Connector properly, so if want me to check anything, let me know...

Thanks in advance...
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Question by:rjccaz
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LVL 37

Expert Comment

by:Jamie McKillop
ID: 29006810
Hello,

Did you setup a second IP on your Exchange server for the new SMTP VS? Here are the instructions to set this up properly - http://msexchangeteam.com/archive/2006/10/04/429090.aspx

JJ
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Author Comment

by:rjccaz
ID: 29007601
I have been fussing with this for a while and one of the configurations I tried was using a second IP address.  From my reading, I understand SBS does not like multiple IP's so was reluctant to try this method.  Besides, it did not seem to work and I don't remember what the error was.

I just found this resource: http://msexchangeteam.com/archive/2006/10/04/429090.aspx
and will be trying yet another walkthrough.

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Author Comment

by:rjccaz
ID: 29011618
Running MS NetMon while sending results in no network traffic to the remote domain.  If I remove the domain from the Address Space, then I am able to see network traffic to the remote domain.  I also see the message stuck in the Queue.  This leads me to believe that it is an internal problem and not anything to do with the network.

Any Ideas?
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LVL 37

Expert Comment

by:Jamie McKillop
ID: 29012220
If you have multiple Virtual SMTP servers, you need an separate IP address for each one. Each Virtual SMTP server binds to an IP. If you only have one IP, the first VS to start will bind to that and the other one won't be able to bind to an IP.

JJ
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Author Comment

by:rjccaz
ID: 29030689
jjmck,

Is this the case even if I use an alternate port for TLS?  I was planning on using the default port of 587 for inbound TLS traffic...
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Accepted Solution

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Jamie McKillop earned 2000 total points
ID: 29084836
You can use one IP if you use a different port for each VS, however, sending servers are going to use port 25 by default unless they are specifically configured with a VS to use port 587.

JJ
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Author Closing Comment

by:rjccaz
ID: 31708457
Thanks! I had tried to configure the SMTP VS to use port 587 (thinking that was the default) and of course, no-one could receive smtp traffic on 587.  Simple, now that I know...
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Expert Comment

by:tech2010
ID: 34498396
Can someone answer this please. If i need to configurie TLS for just few remote domains while i want to continue to operate with non-TLS outside server so should i create new SMTP virutal server and set TLS require opton on it and leave default SMTP VS as it?
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