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Outlook Anywhere connection

By sbelcher ·
I have been troubleshooting this issue for quite a while and my resolve is beginning to flicker in the wind.
I applied MS updates about two months ago that broke my iis in exchange 07... ( somehow that doesn't seem unfamiliar i'm sure. )
Any ways, after restarting and backing backup to a saved copy of IIS, it was backup and running with the exception of autodiscover. I narrowed it down to creating and issuing a UC Cert from our Domain CA, otherwise known as a SAN certificate. This fixed the issue of autodiscovery, but for some reason the outlook anywhere doesn't like this and continues to pester me by connecting and disconnecting from outside my network. Now, if I'm in the network domain, and select use http on fast tcp/ip networks, it works beautifully. I have no problems. But, outside is another story. It constantly connects and reconnects. When I run the autoconfiguration test in outlook this is what I get.
I replaced the server name with "netbios" and the domain name with " domain"

<?xml version="1.0" encoding="utf-8"?>
<Autodiscover xmlns="">
<Response xmlns="">
<LegacyDN>/o=domain/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Recipients/cn=user</LegacyDN>
<ServerDN>/o=domain/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=netbios</ServerDN>
<MdbDN>/o=domain/ou=Exchange Administrative Group (FYDIBOHF23SPDLT)/cn=Configuration/cn=Servers/cn=netbios/cn=Microsoft Private MDB</MdbDN>
<OWAUrl AuthenticationMethod="Fba"></OWAUrl>
<OWAUrl AuthenticationMethod="Basic, Fba"></OWAUrl>

When I go to my OWA site, I have the cert installed and do not get a cert error.
Everything else works great, OWA, OOF, AutoSync.

Any ideas?

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