Help troubleshooting TLS encryption on 2003sbs

Posted on 2011-04-27
Medium Priority
Last Modified: 2012-05-11
Having trouble receiving TLS encrypted email at a clients.  The are required by a vendor to have TLS encrypted emails between servers.  I have done the following:

Created new secure smtp virtual server linked to a second IP address (created manually)
Created domain specific SMTP Connector linked to secure smtp VS
Followed instructions to turn on TLS

I can sent an email to their domain and it arrives encrypted.  When I receive an email from them it isn't encrypted.  I even set up a TLS enabled email address (at our office) to use for testing with same results.  I just don't see how the emails going to find the new SMTP VS since the firewall isn't forwarding any ports to it??  I am totally missing something here...help!
PS I found a post that spoke of an SMTP gateway??
Question by:SBSDan
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LVL 44

Expert Comment

ID: 35479028
Vendor also need to enable TLS. You need TLS at both end.
LVL 44

Accepted Solution

Amit earned 2000 total points
ID: 35479051

Author Comment

ID: 35479197
Yes they have it enabled as I also have another client who uses 2008sbs and that client is sending and receiving TLS with the same exact vendor.  The difference is that exchange 2007 has opertunistic TLS (did I say that right?) built right in, so it sets up without the second SMTP VS

Author Comment

ID: 35479216
I will go thru the Microsoft KB later tonight, I think I covered it all but I will dbl check...thanks

Author Comment

ID: 35480494
OK I did some testing on CheckTLS.com and it looks like the certificate is the only thing failing.  We purchased an SSL for mail.domain.com and hoping this will fix the problem.

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