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Exchange 2003 SMTP TLS connection

Posted on 2007-04-05
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Last Modified: 2013-11-30
Here is the scenerio.  We recently implemented a third party spam filter, our MX record points to them they clean the mail and forward it to us.  We have still been getting a ton of spam that is coming directly to our mail server.  We cant lock down port SMTP because I have mobile users who connect via pop and SMTP for their mail.  I created a second SMTP virtual server on port 2525 and have all mail from our spam company sent to through that connector and I am trying to set the original virtual server on port 25 to only accept encrypted connections but am not having any success.  We have an existing root certificate (owa.redwoodit.com) that we use for RPC and Outlook Web Access.  I installed that certificate to the SMTP virtual connector checked the Require Secure Channel check box and set the Authentication to Basic and Require TLS encryption.  I setup an Outlook 2003 client to connect but I am getting the following error "establishing an encrypted connection to your outgoing (SMTP) server failed".  Any help or suggestions would be greatly appreciated as I am stumped on where to go from here.
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Question by:deanavey
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Sembee earned 250 total points
ID: 18859085
If you have email coming in from the spam company coming in on a different SMTP virtual server then the simple fix for this problem is disable anonymous access to the port 25 SMTP virtual server. As long as your users authenticate when sending (which they should be doing anyway) they will be able to send their email correctly.

Simon.
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Author Comment

by:deanavey
ID: 18859367
If I do that the users will still be sending thier user names in clear text.  Was wanting to make secure things up while making the change.
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Expert Comment

by:Sembee
ID: 18859404
Is the name the users are entering in to the SMTP server settings on their clients the same as on the certificate?

Simon.
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Author Comment

by:deanavey
ID: 18859577
Yes.  
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Expert Comment

by:Stacy Spear
ID: 18859844
Is the TLS server and client ports matching?
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Author Comment

by:deanavey
ID: 18860165
Yes they are on the same ports.
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Author Comment

by:deanavey
ID: 18881683
I was able to find a work around.
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