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Outlook 2007 prompting for username/password when opened

Hello,

We have an environment that exists of the following:

SBS2008
Clients: Win 7 w/ Outlook 2007

When clients open Outlook 2007, they are prompted for a username and password. The title bar in the prompt says: Connect to mail.contoso.com (the external URL for the mailserver) Then Welcome to mail.contoso.com. Entering the domain credentials of domain\username and password works fine, however, the prompt will come back periodically and is obviously not ideal.

I have (to my knowledge) exhausted suggestions with Autodiscover and have upgraded to Exchange SP2 using the SBS Exchange SP2 installation tool. This hasn't made any difference. This is what I get when testing outlook autoconfiguration:

Protocol: Exchange RPC
SERVER: sbserver.domain.local
Login Name: User
Availability Service URL: https://mail.contoso.com/ews/exchange.asmx
OOF URL: https://mail.contoso.com/ews.exchange.asmx
OAB URL: https://mail.contoso.com/oab/a531fcb0-e0c9-4b10-9424-31b4b2e03ba7/
Unified Message Service URL: https://mail.contoso.com/unifiedmessaging/service.asmx
Auth package: Unspecified

Protocol Exchange HTTP
Server: different.contoso.com (This is an external address but appears to be the default one, IE: remote.domain.com, for some reason)
Login Name: User
SSL: Yes
Mutual Authentication: Yes
Availability Service URL: https://different.contoso.com/EWS/Exchange.asmx
OOF URL: https://different.contoso.com/EWS/Exchange.asmx
OAB: URL: https://mail.contso.com/OAB/a531fcb0-e0c9-4b10-9424-31b4b2e03ba7/ (note this one is the correct external FQDN)
Unified Messaging Service: https://different.contso.com/UnifiedMessaging/Service.asmx
Auth Package: Basic
Certificate Principal Name: msstd:different.contoso.com
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zippybungle2003
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Do you run a proxy server for the clients? are the addresses above exlcluded in the proxy settings in IE
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ASKER

Hello
Thank you for taking the time to reply
There is no proxy set up.

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I remember I had this issue on sbs2008 and Win7/Outlook 2010 clients. There is a known bug there which already should be fixed (MS released an update for this).
Make sure you install all updates to the server via Windows Update and also update your clients (including Office) so it contains all latest service packs and updates.
Under server manager, roles, IIS, do you have a tick in windows authentication aswell as basic authentication?
Hello,

I can confirm that the server/clients are up to date.

zippy, to which app pool/web site are you referring for the authentication? I believe I have been through this as per suggestions seen elsewhere and modified the authentication methods accordingly.
Hi,

I've followed that, all seems in order. Outlook still prompts for a username and password.

Does the autoconfiguration output that I posted originally seem okay then?
SOLUTION
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Abbas Haidar
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The problem is now solved.

I deleted the associated certificates and ran the fix my network task. Then re-added the certificate and rebooted the server.

Incidentally, the server was not rebooted after the installation of SP2 (no prompt requesting it) So it's most likely to do with that.

Thanks for all your help