SMTP and TLS

[bharkol1]

Help! I have setup TLS on production servers after testing on non-production and it doesn't work. I am using TLS to have secure connects with certain companies. I have a single virtual smtp server with a thawte certificate installed. Each outbound connection I have gets assigned its own stmtp connector, if TLS is needed then I enable it per connector. So if company xxx requests we send secure email, I create a separate STMP connector that has the company xxx set as the scope and enable the advanced option/outbound to use TLS. We should then only be able to send company XXX email via TLS/SMTP. The problem is that exchange keeps giving an error saying that the 'Remote Server does no support TLS'. If I send from the test servers to the same company it works. After diggin into the SMTP logs I can see the production server try to connect to sites, however it seems to be sending helo rather then ehlo at connection??? I am completely at a loss here - any suggestions???

Thanks,

 

[AndyPeck]

These are quite a good articles

http://www.msexchange.org/tutorials/SMTP-Connections-Servers.html

http://support.microsoft.com/default.aspx?scid=kb;en-us;823019

http://support.microsoft.com/default.aspx?scid=kb;en-us;829721

Are your production exchange servers behind a firewall, and you test servers not (or behind a different firewall)