Outlook 2007 keeps asking for password from SBS 2008 Exchange Server

Is your autodiscover working fine?

Possibilities:
1) Check the authentication on the Autodiscover virtual directory and it should be basic and integrated.
2)Check the authentication on the EWS and OAB and it should be only integrated.
3)When you run testemailautoconfiguration on the outlook check whether the OAB is giving the URL or it is pointing to the public folders.
4)Check for the kernel mode authentication and disable it if it is enabled.
5)You can check for addins on the outlook which requires username and password oftern. You never know.
6) Atlast try to disable IPv6 by following this artilce:
    http://support.microsoft.com/kb/929852
7)It might be autodiscover virtual directory corruption. You can delete and recreate the autodiscover virtual directory.

You may try these things and keep me posted.

           

Hi Eddie, thanks so much for your detailed response.

Did disable IPv6 on the clients and it appeared to fix it, so I was about to celebrate, but then it is happening again, albeit not as frequently.

The weirdest thing is, is that we don't actually have to enter the password, just click 'cancel' and it works!?

When you referred to disabling IPv6, did you mean on the server as well?  As, tried that, but then got the known issue, of 'Applying Computer Settings' taking an age, when rebooting ( http://tinyurl.com/8gpgrk )  Simply re-enabled it and got around that.

From your reading of it, do you think that the following registry fix:

http://tinyurl.com/yebb2hq

will work in SBS 2008 ?

Please see below for screenshots of the Outlook errors as well is details of the DNS forward lookup zones, where following your thoughts on the Autodiscover virtual directory been corrupt, we have looked there.

It's just that I am a bit cautious on playing around with the DNS, is there an idiots guide, to delete and recreate the autodiscover virtual directory ?

Thanks so much in advance!

Cheers - Troy

files attached !
Outlook-Error.jpg
Outlook-Error---2.jpg
Outlook-Error---3.jpg

I have a client with this very same issue.  Researching, I came across this link which claims to remedy the situation:

http://www.howtogeek.com/howto/windows-vista/fix-for-outlook-2007-constantly-asking-for-password-on-vista/
Hope it helps both of us!  I'll let you know my experience later this week...

MY office came down with this exact same problem and it is driving me CRAZY! After restarting the sbs2008 Friday Dec 11 the problem seemed to surface. The problem is simply annoying while everything seems to be functioning fine. But I am being bombarded with questions from all the employees.
Have you found the fix yet?

done some more digging around what updates got installed last Friday 11th December and found the following :

Microsoft Security Advisory (973811)

In here, it does say that there were 3 non-security updates relating to Windows HTTP Services, HTTP Protocol Stack, and Internet Information Services, which is obviously what is being affected with this error.

However, reading the following:

Microsoft Security Advisory: Extended protection for authentication

It doesn't appear to address Windows 7 clients, which we all have !

and from the following :

Extended Protection for Authentication

It doesn't look like there is a Windows 7 registry fix for this yet - crazy!

Has anyone had any joy in fixing this?

( flyinace2 - can you confirm that you are also run running SBS 2008 and OL 2007 on Win 7 machines ? )

We have SBS2008 OL 2007 but all our machines are XP...

okay, then it looks like it isn't something that we have mucked up, must be something to do with the Extended Protection for Authentication updates that came through.

Funnily enough, when I am actually on Outlook and using it, it doesn't come up as much ( probably once every 2 hours or so ), but when the machine has been left alone for a few hours and then people come back to it, then the support calls start coming in :-(

Would appreciate anyone's help to get around this!

Same here... I actually asked this same question and it has a different solution that I am currently trying to work through. I'm not exactly a sbs2008 expert.
https://www.experts-exchange.com/questions/24977847/Exchange-2007-asking-for-username-and-password.html

Actually IT is just my secondary job here.

one of our IT guys found the following :

Extended Protection for Authentication

Have enabled the Windows Authentication as per the IIS instructions and will let you know how it does !

Cheers - Troy

ok, cheers, let us know how you go; have to head out for a few hours, so will let you know how it has gone !

( anyone else loaded these updates and having similar issues ? )

Thanks RobWill that worked for us!!!!

Thanks as well Robwill; it worked for us as well!

Glad to hear.
Thanks troy_g.
Cheers!
--Rob

hi just to let you know I had this exact problem . i had no server.domain.local A record is DNS . Added the record and the problem resolved immediately. Good luck to all.
Kath

A record one is interesting.