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Microsoft Exchange Outlook Anywhere SSL Issue

Last Modified: 2012-05-09
I am having the weirdest of issues.  We recently installed Exchange 2010.  Everything works and works quite well until I install an SSL SAN Certificate so that we can use Outlook Anywhere.

1.  The certificate works when launching Outlook Web Access and generates no errors.
2.  When logging in with an Office 2007 Outlook Client, users are prompted with a Security Alert (locally or via Outlook Anywhere).  The alert says that The Security Certificate is from a trusted certifying authority, the certificate has expired or is not yet valid and the name on the certificate is invalid.

Viewing the certificate shows an expired certificate from a company we have never heard of www.thesearidge.com  .  

This is a brand new certificate on a new Exchange 2010 server and everything works except this disconcerting error message.  Users can click past the error with no consequences.

A review of all of the certificate services reveals that the certficate does not exist on any of our systems local, computer or system level.

Anyone have any suggestions?  I have removed, revoked and created an entirely new cert with the same credentials specifying the same hosts names.  Basically I followed the book.

This is very frustrating as I cannot identify the source of the certificate error.

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