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Intermittent Outlook/Exchange Issue- Asking for password

Posted on 2008-09-30
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Last Modified: 2012-05-05
I posted on this before and thought I had it licked. Very intermittently outlook prompts for your username and password, over and over again, you can enter it as many times as you like but it is never happy. If you click cancel and then click on "need pasword" in the lower right it will be happy. We just re-did everything and are running Exchange 2007 on Server 2008. Also I used the "trick" for a single cert for all of the Exchange functions, and my external machine name is different then my internal name, so exchange.xxxx.com and exchange.xxxxxx.local. Please help.
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Question by:nkrueger84
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Expert Comment

by:guydemarco
ID: 22609487
Check to see if there is a communication problem with the AD, or if the AD is having issues with 100% CPU usage. Look at the AD logs in event viewer, while you're at it.

Check the NIC settings to make sure they're not going into power-down mode.
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by:abdulzis
ID: 22609699
Also verifiy none of the virtuals directories in IIS 7 are set to anonymous incl OAB, EWS, Autodiscover and UM.
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Author Comment

by:nkrueger84
ID: 22609782
No anonymous on anything....so far I do not see any issues on the exchange server or either DC..

Also, in case it matters, everything is now virtualized including Exchange and both DCs...
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by:abdulzis
ID: 22609804
Does this happen for Outlook 2003 and 2007 clients?
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by:nkrueger84
ID: 22609845
We only have 2007 clients
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by:abdulzis
ID: 22609860
plz paste the output of

get-webservicesvirtualdirectory | fl *url*
get-oabvirtualdirectory | fl *url*
get-clientaccessserver | fl *url*
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Author Comment

by:nkrueger84
ID: 22609966
[PS] C:\Windows\System32>get-webservicesvirtualdirectory | fl *url*


InternalNLBBypassUrl : https://exchange.xxxx.local/ews/exchange.asmx
InternalUrl          : https://exchange.xxxxx.com/ews/exchange.asmx
ExternalUrl          : https://exchange.xxxxxx.com/ews/exchange.asmx


[PS] C:\Windows\System32>get-oabvirtualdirectory | fl *url*


InternalUrl : https://exchange.xxxxxx.com/OAB
ExternalUrl : https://exchange.xxxxxxx.com/OAB

[PS] C:\Windows\System32>get-clientaccessserver | fl *url*

produced nothing...


Also, FYI, this is a single box installation of Exchange.


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Expert Comment

by:abdulzis
ID: 22609994
If you ping exchange.xxxxxxx.com from the workstation, does it resolve to the internal IP or external IP of the CAS? Also do you have any proxy server specified in Internet Explorer options?
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Author Comment

by:nkrueger84
ID: 22610025
I have it resolving the internal address of the CAS. No proxy server is specified.
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Author Comment

by:nkrueger84
ID: 22627709
I still haven't found anything that looks out of the ordinary to me....
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Accepted Solution

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nkrueger84 earned 0 total points
ID: 22651428
In theory I have found the answer over at this blog: http://blog.aaronmarks.com/?p=65 (Thank You Aaron!)

The issue is with changes in IIS7/Server 2008 on which I am running Exchange 2007. Apparently IIS 7 uses kernel mode authentication by default and you need to turn that OFF using the command below:

%systemroot%\system32\inetsrv\appcmd.exe set config /section:system.webserver/security/authentication/windowsauthentication /usekernelmode:false

I just issued the command will post again in a day or day when verified that this takes care of it.
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