Outlook anywhere issues with XP/Office 07 when using a SAN certificate

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John Mello
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Joined: 12/15/2010
Outlook anywhere issues with XP/Office 07 when using a SAN certificate

I'm hoping to pick everyone's brain on an issue I'm having with Outlook Anywhere and Windows XP/Office 2007 clients. Currently we have Outlook Anywhere enabled and it works fine with our Windows 7/Outlook 2010 laptops. I've also tested Outlook anywhere via the MESRCA which works but does give a warning about making sure Root Certificate updates is enabled.
When I Open Outlook 2007 on a Windows XP computer that is outside the network it hangs on the connection process for a few minutes then gives up. The System Event Log shows two warning events for LSASRV, basically stating that it can't get to the one of the external address of my mail server (mail.voxmedica.com). Unfortunately it's not the one that is specified in Outlook Anywhere. Below are my settings:
URL : https://webmail.voxmedica.com
Cert Principal Name : msstd:voxmedica.com (I'm using a 20 doamin SAN cert and my CN is voxmedica.com)
Authentication : NTLM Authentication

All other External Exchange services (ActiveSync, AutoDiscover, EWS, and OWS) work with no issues. At this point the only solution I can think of is to revoke my current SAN cert and buy a new one with my CN being the same as my external URL for Outlook Anywhere. Any other suggestions before I do that?

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