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Outlook Anywhere SBS 2008

Posted on 2009-05-09
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Last Modified: 2012-05-06
Alright here goes. I have a brand new SBS 2008 server that I am setting up for a new client.  No migration, brand new setup.  Everything is working great except for Outlook Anywhere.  I have been reading for the better part of 5 hours and still can't get this to work right.

here is the issue:
My personal laptop is running vista with Outlook 2007 it will immediately connect to the new server remotely using Outlook Anywhere with my test account.  I can also connect using my Vista computer to any mailbox on the system that I want using Outlook Anywhere.

Any other computer running Windows XP and Outlook 2007 or 2003 just get the password prompt over and over and over.  

I have a third party wild card certificate installed on the server and using the default.. remote.  prefix that has been recommended for SBS.  (From what I read SBS and Exchange 07 work a little different then if you use full server and exchange editions).  All of the server settings have the appropriate FQDN setup, the cert works using the https://servername/rpc  I have disabled and re-enable Outlook Anywhere, reset the certs, and I just continue to get repeated password prompts.  From what I have found originally, most people had the reverse problem with Vista not connecting.  Also SBS server is pretty much configured out of the box from what I have read, add the cert, turn on Outlook Anywhere, I did edit the bindings to use the correct cert in IIS 7 and its supposed to work.  Of course the firewall rules are in place or my machine wouldn't connect right.  RPC proxy etc were already installed and configured out of the box.

I originally thought that it was problems with the other computers but I have been unsuccessful on any other pc except for mine.

I assume since my computer works fine that there and the only difference is Vista that there is something missing or needs added to XP machines to get it to work right.  I am in the process of trying to track down another VIsta machine to see if I can get it to connect as well and test my theory.

Anyone else seen this before?  

Let me explain that I am new to the Server 08 exchange 07 scene. I have been admin engineer for years and can do all of this on 03 software, but this has been my first opportunity with clients actually wanting  to use the new stuff and spend the money, so I actually feel pretty lucky and this is the only issue I have had so far (and the final thing to be solved before I can wrap this project).
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Question by:jbmos2333
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by:Quetzal
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Just to be clear, you are configuring RPC over HTTPs for Outlook, right?
Check to see that you are using basic authentication.
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Author Comment

by:jbmos2333
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Yes RPC over HTTPS.  It is basic authentication.  I checked and rechecked all of the basic settings.  Exchange 07 refers to this as Outlook Anywhere now not RPC over HTTP
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Philip Elder earned 500 total points
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Make sure the Principal Name setting in the Outlook Anywhere settings is *.domain.com.

See about half way down where Outlook configuration is explained:
http://blog.mpecsinc.ca/2008/08/sbs-2k3-premium-configuring-ssl.html

Philip
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Author Closing Comment

by:jbmos2333
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You are the man. That never occurred to me.  My xp outlook 2003 machine now connected immediately.

Just curious, why would my Vista, Outlook 07 machine connect without that setting.  I have it set as remote.domain.com in that machine?
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Author Comment

by:jbmos2333
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I also never once got the proxy server certificate error.  And I had this setup on at least 6 different computers.
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by:Philip Elder
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Vista with Outlook 2007 is a lot more aware of the settings needed to connect. The server settings for Outlook Anywhere should have been set up during your initial profile fire up. This does not happen with XP/Outlook 2003 or even 2007.

Philip
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Author Comment

by:jbmos2333
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Thanks again. Yeah it would find the server on the auto setup for Outlook 2007 and then just fail.  Works great now.  Appreciate the help.
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