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Outlook 2007 users cannot connect to Outlook Anywhere (Exchange 2010)

Posted on 2013-12-13
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Last Modified: 2014-01-07
I think I've read every article on the web, and I can't find an answer to this.  Running a single Exchange 2010 R2 server for a company of about 50 users.  Internal email works just fine, OWA works great, and the server passes all the tests on Microsofts online exchange connectivity testing site.  It seems that users running Outlook 2010 have no issue going offsite, opening Outlook and using Outlook Anywhere to send/receive email.  I've tested it with my own account and it works great.  Same user, same account on an XP machine running Outlook 2007 works fine inside, but as soon as they're off our network and on an external internet connection, they are immediately prompted for credentials over and over and their network credentials do not work and they don't connect.  I've tried creating new profiles, I've tried every different security setting in Outlook, I've tried checking/unchecking every single box in the Advance connection settings, etc.... The ONLY thing I can think of, is this started happening a few days ago when I updated our Comodo UCC certificate, but nothing changed on the new cert, it has the same names that it did before....I've made sure that the new cert works in OWA, and it does.....


WHAT AM I MISSING?!?!?  Thanks.
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Question by:tenover
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by:tenover
ID: 39718003
Well, I guess it's not an Outlook 2007 issue, but maybe an XP issue....???  I just got home and opened Outlook 2007 on my Windows 7 desktop machine and Outlook Anywhere configured the account using Autodiscover with no issues whatsoever....No prompts, nothing, it worked perfectly.
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tenover earned 0 total points
ID: 39762188
Turned out to be an issue with how the alternate domains were listed on the UCC.  Apaprently Windows XP cannot/does not accept anything besides the common name(CN) entry. I got online and modified my UCC and all is good now.
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Author Closing Comment

by:tenover
ID: 39762191
Figured out myself.
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