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exchange outlook clients unable to connect to server SBS 2008 with Exchange 2007 server

Posted on 2010-09-19
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Last Modified: 2012-06-21
I have a new installation of SBS 2008.
The external domain name is for example "mycompany.com"
The internal domain is "mc.local"
OWA I can logon with user id and password but
Outlook 2007 keeps asking for user id and password. Tried many combinations but nothing seems to authenticate.
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Question by:Terrymac_Computer_Guy
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15 Comments
 
LVL 4

Expert Comment

by:kenycl
ID: 33713208
username and password should either be domain/username
or username@domain

server should be mc.local on your outlook
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LVL 2

Expert Comment

by:Robert Holmes
ID: 33713222
To clarify your question is the computer accessing the exchange server with Outlook 2007 is on the internal network or externally?
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LVL 2

Assisted Solution

by:Robert Holmes
Robert Holmes earned 50 total points
ID: 33713227
One solution to test is to install the latest service packs for Exchange Server 2007 as I have seen this problem be fixed by a service pack update.
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Author Comment

by:Terrymac_Computer_Guy
ID: 33713236
both these don't work
Usually Outlook 2007 is fine with automatically setting correctly
The only difference with this SBS 2008 install from others I've done is the external and internal domain are named differently (usually it mycompany.comand mycompany.local)  
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Author Comment

by:Terrymac_Computer_Guy
ID: 33713251
On the internal network. I'm having the same problem with all the workstations internally.
Latest service packs are applied for both SBS 2008 server and Exchange 2007
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LVL 12

Expert Comment

by:FDiskWizard
ID: 33713554
Are the Exchange server event logs showing anything? App and Security...
Maybe time to whip out some diagnostics. I can only think of DSDiag off the top of my head
http://smtp25.blogspot.com/2007/10/dcdiag-verify-domain-controller-health.html

I think there is an SMTPDiag for Exchange testing.
Oh, the other 2 I was trying to think of DCDiag and Netdiag.

Try those.
Also, Is Outlook doing RPC over HTTP? Try it if not.
Are all the normal services running on the server? Can you browse to a share on the server?
If you recreate a mail profile on the PC, does it resolve the user's name correctly?

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Author Comment

by:Terrymac_Computer_Guy
ID: 33713648
Browsing share works fine
it looks like rpc over http is setup by default could it be the firewall preventing this? Even though I'm locally on the domain does it authenticate over the internet to get to the exchange server?
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LVL 2

Expert Comment

by:Robert Holmes
ID: 33713651
It wouldn't hurt checking the firewall.
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Author Comment

by:Terrymac_Computer_Guy
ID: 33713652
Also looking at the send receive progress it shows sending successfull and receiving not succesful
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LVL 4

Expert Comment

by:kenycl
ID: 33713675
try testing it from here and see what results you get

https://www.testexchangeconnectivity.com
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LVL 56

Accepted Solution

by:
Cliff Galiher earned 450 total points
ID: 33718598
MU does not install Exchange service packs. You *must* actually go, download, and install them. This is known conflict between a security patch and older versions of Ex2007. Add Exchange SP3 to resolve the issue.
-Cliff
 
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Author Comment

by:Terrymac_Computer_Guy
ID: 33718898
Cliff,

Can you explain what SP3 does to correct this so I can understand better what is broken.

I also just did a test on a workstation with Outlook 2007 and let it automatically set outlook up and up came the user id and password prompt. I then backed out a couple of steps and checked setup Outlook 2007 manually and it worked.

I looked at the outlook exchange more settings and this time the only thing it didn't fill in setup is the outlook anywhere on the connection tab. So I'm gueesing it has a problem with this.

Also any advice for installing Exchange SP3?
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LVL 56

Expert Comment

by:Cliff Galiher
ID: 33719072
The short answer is that a security update (KB973917) enabled windows authentication on a global level where it was previously disabled.
This causes an issue with how Exchange is set up on SBS by default, where it uses user-level authentication instead of kernel-level authentication, and that conflict causes repeating prompts.
Exchange SP1 UR8 (and by proxy SP2 and SP3) disabled kernel-level authentication, thus preserving the windows authentication that KB973917 enables, but in a way that no longer conflicts with the RPC authentication needs of Exchange for autodiscovery/RPC/MAPI.
-Cliff
 
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Author Comment

by:Terrymac_Computer_Guy
ID: 33720678
Thanks cliff,

We will try this and see. I've had a look at this link here for instructions installing to SBS 2008.

http://support.microsoft.com/kb/982423

We didn't install Forefront so won't have to disable it.

Will let you know how we made out.
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Author Closing Comment

by:Terrymac_Computer_Guy
ID: 33766753
Thanks Cliff this cleared up the error. Since you explained in more detail to help me understand I'll award you more of the points.
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