Question : Outlook 2007/2010 Prompts for Autodiscover Password

Hi,
I recently upgraded our SBS 2008 Server to SP2 and, soon afterwards, we've been having issues with Outlook repeatedly prompting for the Autodiscover credentials even after valid ones have been entered. After a while, it stopped and everything seemed to be working, but now it's back to doing it. It happens when connected both internally and externally. Also, when I try to access the https://remote.website.com/autodiscover/autodiscover.xml, it does the same thing of repeatedly prompting and rejecting valid credentials. Any suggestions would be greatly appreciated!

Answer : Outlook 2007/2010 Prompts for Autodiscover Password

There have been numerous posts where Outlook 2007, with SBS 2008, keeps prompting for passwords. The following link suggests the problem is due to server updates, and installing Exchange rollup 9 resolves the issue. Perhaps your situation is similar. Details on the posters issue can be found on the previous page of the thread.
http://www.petri.co.il/forums/showthread.php?t=42566&page=2