troubleshooting Question

IIS6 or 7 Virtual SMTP Server - Opportunistic TLS

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citpajFlag for Canada asked on
Microsoft IIS Web ServerWindows Server 2003Windows Server 2008
4 Comments1 Solution2362 ViewsLast Modified:
We run an internal SMTP relay server, on 32-bit standard edition Windows 2003 Server, via IIS6 virtual SMTP server.  We need to turn on TLS for some but not all external recipients.  

I've read that when you enable TLS on the SMTP server bundled with IIS6  the SMTP server will require TLS support on ALL remote hosts it tries to send email to.

Is there any way to enable 'Opportunistic TLS' on this or Windows Server 2008?  That is to say where our server will only send mail using TLS if the remote SMTP server advertises it is capable of accepting it, and will send all other mail normally, to those who don't accept TLS email?
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