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Outlook Anywhere SBS 2008

Posted on 2009-05-09
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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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7 Comments
 
LVL 11

Expert Comment

by:Quetzal
ID: 24346742
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
ID: 24346746
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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LVL 39

Accepted Solution

by:
Philip Elder earned 2000 total points
ID: 24346769
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
ID: 31579858
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
ID: 24346782
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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LVL 39

Expert Comment

by:Philip Elder
ID: 24346793
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
ID: 24346796
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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