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exchange 2007 keeps asking for a password

Posted on 2011-03-01
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Last Modified: 2012-05-11
Hi, I manage a small server running SBS 2008 with exchange 2007.
It has been running with out faults for months til one client connected opened outlook and was prompted for an exchange password. Now all of the clients are having the same issue.

In the lower left hand corner of the screen of outlook it says "exchange needs a password. Click here to type a password" Once clicked it instantly changes to "connected to exchange"

but it will only be a matter of minute to hours and it will prompt again.

I have update the server and rolled out rollup 10 for the exchange to SP1

Any ideas
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Question by:jaramart
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Expert Comment

by:Glen Knight
ID: 35006491
there are a number of reasons why this can happen, see my guide here for help on resolving them: http://www.experts-exchange.com/Software/Server_Software/Email_Servers/Exchange/A_2300-Outlook-continually-prompting-for-username-and-password.html

My guide says Service Pack 2 for Exchange, you should really now be using service Pack 3
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Expert Comment

by:Tonypeswani
ID: 35006608
Yes that correct service pack needs to be applied.

Thank you.
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Expert Comment

by:PraveenBalan
ID: 35006644
Yes, SP1 is quite older now, please upgrade.

If you plan to upgrade to SP3, ensure that you also apply the roll-up, because MS identified a OWA/SMIME version mismatch post the release of SP3.

http://msexchangeteam.com/archive/2010/09/09/456198.aspx

-Praveen
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Author Comment

by:jaramart
ID: 35006862
I treied to update using the Server tool for updating exchange to service pack two and it fails saying "the update could not complete, server needs to be restarted to complete a previous update" I have restarted the server and still no good
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Expert Comment

by:Glen Knight
ID: 35006887
go straight for service pack 3.  The tool is not required for this.
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by:Glen Knight
ID: 35006892
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Author Comment

by:jaramart
ID: 35007237
tried that too but same message "A reboot is required for pending update please restart and rerun"

But i have restarted and it doesnt seem to install any update??
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Expert Comment

by:Glen Knight
ID: 35007273
Open the registry on the server and navigate to HKEY_LOCAL_MACHINE\SYSTEM\CurrentControlSet\Control\Session Manager

Look for a key called PendingFileRenameOperations and rename it.  Then try the install again.
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Author Comment

by:jaramart
ID: 35035154
Ok updated to service Pack 3 but the problem is stil there. They are not (well at least i think there not) Auth. by SSL. I have not create the Cert. I dont know much about exchange at all. But i noticed the other day that when outlook asks for the username and password the dialog box says connecting to "remote.XXXX.org.au (the XXXX is the name of the Outlook anywhere site built into sbs2008) is this normal?
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Expert Comment

by:Glen Knight
ID: 35035172
yes, this is normal, what happens when you ping remote.xxxx.org.au
What IP address do you get back? Is it internal or external?
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Author Comment

by:jaramart
ID: 35035232
pinged the site and its internal and i get a reply
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Author Comment

by:jaramart
ID: 35035348
This is really wierd. I have been openning and closing outlook to test it. I open it and it says "welcome back to remote.XXXX.org.au. Enter username and password."

Then i closed it and tried again this time it said "welcome Back to server1.mydomain.local please eneter etc etc

so i closed it and tried again and the box popped up with the first messge remote.XXXX.org.au i clicked cancel and it said connected then i hit send a receive and all is good then a few minute later it pops up again and says welcomce to server1.mydomain.local.

?????????
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Expert Comment

by:Glen Knight
ID: 35035403
interesting, did you try the kernel mode fix in my article?
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Author Comment

by:jaramart
ID: 35035411
Yes i tried that. still no help
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Expert Comment

by:Glen Knight
ID: 35035420
Can you try running the Fix my Network Wizard, sound like you are having a few problems.
http://blogs.technet.com/b/sbs/archive/2008/11/26/introduction-to-the-fix-my-network-wizard-fncw.aspx
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Author Comment

by:jaramart
ID: 35035500
Run it and it fix a few issues with DNS Records but has not solved my issue
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Expert Comment

by:Glen Knight
ID: 35035504
what records did it fix?

Run IPCONFIG /FLUSHDNS on the client and try again?
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Author Comment

by:jaramart
ID: 35035564
it said it fix the A record on the dns. I ran the IPCONFIG but go still
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Expert Comment

by:Glen Knight
ID: 35035569
does your server have 2 network cards?
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Author Comment

by:jaramart
ID: 35035579
no just one card but two ports.
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Expert Comment

by:Glen Knight
ID: 35035594
still is the same, make sure that only one is in use and the other is disabled.
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Author Comment

by:jaramart
ID: 35035605
yeah no the other port is disabled
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Author Comment

by:jaramart
ID: 35042963
Just a thought... there are two servers in the forest. one is sbs 2008 and the other is server 2003 std, SBS 2008 is set for the domain UAC and exchange while the other is back up server running only as a secondry DNS in the event of failure of the first. Could Outlook be promting the exchange for auth. and getting availd respone but then promt the second server for an exchange auth but fails because there is no exchange on the second?
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Assisted Solution

by:Glen Knight
Glen Knight earned 500 total points
ID: 35042979
Check DNS on both servers and make sure the records match? Try changing the client so it only uses the SBS server for DNs and see if you get the same results
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Accepted Solution

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jaramart earned 0 total points
ID: 35045833
Checked and the client is getting the correct DNS through nslookup.
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Expert Comment

by:PCFix1011
ID: 35168947
I am having this EXACT same problem......
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Assisted Solution

by:jaramart
jaramart earned 0 total points
ID: 35177122
Ok problem solved!.

It is to do with the Autodiscover service in outlook, and the default Outlook anywhere website that is part of sbs 2008 ie.  remote.myserver.com

I check the dns records and found that all the A records where there as they should be. However no DNS record existed for remote.myserver.com, what was happening was outlook would look to the DNS for auth. get it, then look to DNS remote.myserver.com for auth. for the autodiscover service. and it would fail! thus the reason why it would connect and disconnect but still send and recieve.

To fix this create a DNS A record for remote.myserver.com and point it to the IP address of exchange. and Well its been good for two weeks now.
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Author Closing Comment

by:jaramart
ID: 35213329
After being prompted to check the DNS records i thought i would do some research on the DNS A records required for exchange.
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