Exchange 2010 and Outlook prompting for password

Some Outlook clients are alerting for “need password”.  Even after the password is entered, a box pops up requesting the password for the user again, thus creating a never-ending cycle.  Sometimes, a computer reboot will help or choosing “Work Offline” followed by clicking it again works sometimes.  However, the issue eventually resumes, and some of the time these don’t fix it at all.  I had luck once with restarting the Exchange Server, but event that doesn’t seem to help.  As a last resort, I have had to remove the Outlook profile from a computer and then add it back to fix the problem.  Once again, this only fixes it until it happens again, and isn’t a permanent fix.

It doesn’t happen for all users, but I have seen it occur on 2003, 2007, and 2010(beta) versions of the Outlook client.  When it does happen, it seems to occur to the same users multiple times (this could be that not all users report it everytime).  

I have checked my certificatenames i.e. autodiscover etc and they appear correct and it resolves correctly. Any ideas?
x09projectAsked:
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Carol ChisholmCommented:
Exchange 2010 requires a secure connection between the client and the server.
http://www.howexchangeworks.com/2009/09/cant-connect-outlook-2003-to-exchange.html
If you're using the rpc over http check the authentication method matches with IIS on the server : basic to basic for example.
x09projectAuthor Commented:
Thanks for the posting - the article was informative. But everyone is able to access their mailboxes - it is just from time to time this "need password" keeps popping up and sometimes a reboot may make things work for awhile etc -
Carol ChisholmCommented:
Interesting, I had just that happen to me this morning for the first time. I had left my workstation on overnight, usually it is turned off. I will now investigate.
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Carol ChisholmCommented:
My Exchange server restarted at 3 am due to an update (it's a lab anvironment), as did the Domain Controller.
Outlook, still connected lost it's credentials and needed then re-entering. Any help?
x09projectAuthor Commented:
Not sure that is addressing my situation - some 2003 and 2007 clients get this password prompt a lot, other dont get it. Is it Autodiscover? Is it encryption settings? Im at a lost to understand exactly what is happening -
Carol ChisholmCommented:
It's often the basic or NTLM negotiaiton in the HTTP proxy settings. Outlook seems to reset them from time to time.

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x09projectAuthor Commented:
Addressed part of the problem but helped me complete the solutoin
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