Issue with Outlook 2010 - connecting to exchange on SBS 2008 - always ask's for users password

Posted on 2010-09-21
Medium Priority
Last Modified: 2012-05-10
We've just setup a fresh SBS server 2008, and several windows 7 workstations all woth Outlook 2010 installed. When we initially set each PC up they worked fine discovering exchange autofilling the username in and connected as you would expect. the following day each machine was asking for a password upon opening Outlook and upon sending and recieving, we also had the same issue with outlook on the server itself.

They were on a dynamic WAN IP address which has now been set to Static and we've reissued the self certificate and it seems to have fixed the issue with Outlook on the server... however the machines are still the same.

I have also tried disconnecting a machine from the network and reconnectin/resetting up Outlook but still have the same result.

Please Help
Question by:mendmycomputer
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Expert Comment

ID: 33723520
Can you confirm the authentication method used in Outlook profile ?

Are users loggin on machines with the same account which is associated with mailbox ?

Expert Comment

ID: 33723890
You need to add your Windows 7 workstations to your SBS server 2008 "domain". One way of doing this is to right-click on "My Computer" and choose "Properties".
Click on "Change Settings" and then click "Change" button. That is where you can click "Domain" radio button and enter the name of your SBS server 2008  domain.
LVL 31

Accepted Solution

MegaNuk3 earned 2000 total points
ID: 33723906
Have you installed SP2 or SP3 for Exchange 2007 on there? SP2 fixes a lot of password prompt issues.
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Expert Comment

ID: 33724003
Good point MegaNuk3,
In my experience, it was sufficient to run Windows Updates on SBS server 2008.

Author Comment

ID: 33724281
Hi There, In answer to questions as presented, the users are logging on to the domain with the same details as Outlook was automatically configured to use.

And no we hadn't installed any service packs for Exchange 2007 which is currently build 08.01.0240.006 which i believe is SP1, we had done windows updates which of course doesn't check this :/

I will download the service pack(s) and update on the outcome.

Author Comment

ID: 33724301
Not 100% clear on MS download site but can i go straight from SP1 to SP3 without downloading and installing SP2  first?
LVL 31

Expert Comment

ID: 33724740
Go straight to SP3:
SP3 on SBS2008 no longer requires an install tool:

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