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Enable StartTLS Exchange 2010

Posted on 2014-10-13
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Last Modified: 2015-11-30
I'm trying to get StartTLS enabled on my Exchange 2010 on Windows 2008R2
I have followed the steps in this link:
http://terenceluk.blogspot.com/2013/09/enabling-tls-for-exchange-server-2010.html
Locally, when I telnet to 25 and type "ehlo", I see STARTTLS listed.
Externally, when I do the same, STARTTLS is not listed.

I don't see any Event Viewer entries to show any errors.

I've read it possibly a firewall issue.  My Cisco engineer looked at the ASA and didn't see anything.  Even followed this link
http://www.cisco.com/c/en/us/support/docs/security/asa-5500-x-series-next-generation-firewalls/113336-asa83-mailserver-inside.html which I found from here:
http://www.expta.com/2014/03/troubleshooting-tls-smtp-connections-to.html

There is only one SSL Certificate which all services are using.  It was purchased from SSLS.com

What step am I missing?
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Question by:NYTECJ
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LVL 8

Expert Comment

by:tshearon
ID: 40377526
Do you have the ESMTP Inspection feature enabled on your ASA? If so you want to disable that and see if it works.
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Author Comment

by:NYTECJ
ID: 40377542
Yes, ESMTP is disabled.  As per the link I mentioned above to Cisco.
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LVL 63

Accepted Solution

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Simon Butler (Sembee) earned 500 total points
ID: 40377611
If it works internally, then it should work externally as well.
The only reason I can think of that it would be different is on the Receive Connector configuration, that you have an additional connector configured for internal traffic only. If you have the two default connectors (Default and Client) and their configuration is default, then there is nothing else to do with Exchange. I would be pointing the finger at the Cisco.

Simon.
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Author Comment

by:NYTECJ
ID: 40406857
I'm sorry for not updating this as I should.  I'm having my Cisco engineer look at it.
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Author Comment

by:NYTECJ
ID: 41341506
This was resolved.  Cisco equipment was upgraded to the latest firmware.  We now have it working.
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Author Closing Comment

by:NYTECJ
ID: 41341525
It was the Cisco equipment.  Upgraded the Cisco to latest firmware.
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