Windows Server 2008 R2 virtual smtp server Relaying

Hey Guys and Gals,
I'm attempting to forward the Virtual SMTP Relay on a 2008 machine to my Plesk SMTP relay, but it won't allow me to set up the connection with TLS encryption (which Plesk requires for it's encryption choice).
Email goes through fine when I use port 25, but otherwise I'm not even sure it's reaching the Plesk server, which makes me think it's at the Windows Server level.
Does Server 2008's SMTP relay require a certificate from the Plesk server?
That's my best guess at this moment.
Any help would be greatly appreciated.
Cheers,
Rhys

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Windows 2008 R2 smtp server Relay only selected servers without authentication

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Hi,
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http://social.technet.microsoft.com/Forums/en-US/home?forum=windowsserver2008r2webtechnologies
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Mail Item ID 19
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Last Modified By xx
Message
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Hi,
I followed this blog and got the below error message in the Database Mail Log.
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[http://imageshack.us/photo/my-images/3/sorunc.jpg/|http://imageshack.us/photo/my-images/3/sorunc.jpg/]

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Disclaimer: This posting is provided "AS IS" with no warranties or guarantees , and confers no rights.

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From the Parallels website:
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Windows Server 2008 R2 virtual smtp server Relaying

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