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Outlook asking for password every session

Posted on 2011-05-09
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Last Modified: 2012-11-21
I've had a quick look through the knowledge base but none of the suggestions I could find help with this particular case.

We have Exchange 2003 and 50+ users.  There is just one user who's Outlook is asking for a password everytime the program is started.
It does it with Office 2k3, Office 2k7 and Office 2010.  Yes I've tried it with all!
The client setup is exactly the same procedure as all other accounts, yet it seems to ask for a password for this account only.

Anyone got any ideas on how to fix this?
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Question by:Reece Dodds
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LVL 39

Expert Comment

by:Aaron Tomosky
ID: 35725374
Sounds like a corrupted userprofile. You can try deleting the outlook profile but you probably need to delete the entire user and recreate.
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Author Comment

by:Reece Dodds
ID: 35725396
that's the thing... This is a fairly recent exchange 2003 build and it was doing the same problem on the old server.  (I did use exmerge to retrieve mailboxes though).
I will try that suggestion if needed but before I do is there any other account related setting in Exchange that could cause this?
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LVL 31

Expert Comment

by:MegaNuk3
ID: 35726501
Try outlook /rpcdiag and see if you can see what servername outlook is connecting to when the prompt occurs. Also confirm that when you do authenticate that outlook connects over TCP and not HTTP
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Expert Comment

by:djpazza
ID: 35726694
Have you doubled check the outlook settings with another working machine?

Encrypt exchange connection ticked ?
Authentication type?
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Author Comment

by:Reece Dodds
ID: 35734505
identical to my machine... which works fine.

encrypt exchange ticked.
always prompt unticked.
logon network security set to Negotiate Authentication.
set to use LAN and not HTTP
Cached mode on

out of curiosity i changed the always prompt option and when ticked the password prompt is different from when it is unticked.
when unticked it says:  Welcome back to mail.mydomain.com.au... and the username is "COMPUTERNAME\username" rather than just "username"
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Author Comment

by:Reece Dodds
ID: 35734535
ok weird...
I came across another PC that is in our office (the real problem one is not physically in our office) and I put a tick in the Always Prompt option, restarted outlook, logged in, unticked that option, restarted again and logged in.
Now whenever outlook is exited and reopened or the computer restarted, it does not ask for a password anymore.  Hooray!!!!
I will try this same fluke with the other problem PC and see what happens.
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Expert Comment

by:MegaNuk3
ID: 35735351
Fingers crossed. I'd reboot that computer at your office with the password prompt issue to make sure the problem is truely gone on that machine.
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LVL 7

Author Comment

by:Reece Dodds
ID: 35876262
OK, i've had more time to try and troubleshoot this one...
I've exported all data from the troublesome account and then completely deleted the account from Exchange AD and the client PC.
Starting fresh with Outlook on the client PC, I created a new profile with a newly created exchange account... If I load outlook, it does not ask for a password (even after a restart).
So I then created a new exchange account using the same domain as the troublesome account, when I load outlook, it does not ask for a password (even after a restart).
So I create a new exchange account with exactly the same settings as the above (working) account for the troublesome email address... when i load outlook it asks for a password once, then not again until the PC is restarted.
I'm lost...
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LVL 31

Expert Comment

by:MegaNuk3
ID: 35876826
Can you confirm that if you do
Start-->Run
Outlook /rpcdiag
That it is not connecting over HTTP?
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Author Comment

by:Reece Dodds
ID: 35876986
How do you tell?

The screenshot I've attached is for the new account i've just created that is configured with the same domain and settings as the problematic email yet works fine...

 working ok!
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Expert Comment

by:MegaNuk3
ID: 35877236
In the 'Conn' column. It shows HTTP when connecting over HTTP.
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Author Comment

by:Reece Dodds
ID: 35883558
OK.  

In deleting the problem mailbox, i did not wait for it to be "purged" before recreating it.  Should I have waited or manually done the "purge"?

It's odd that a brand new email account (the same as the problem one but with one letter different) has absolutely no issues at all...
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Author Comment

by:Reece Dodds
ID: 35884189
To answer my above question, I deleted (yesterday) the problem account again and waited till today (the mail store dismount, backup and remount overnight) and the mailbox had the little red cross on it and the ability to purge it.
I did this.
I then ran the mailbox cleanup wizard, which seemed to do nothing.
I gave it a few hours and tried emailing the problem address and was getting bounce backs saying the address does not exist at this domain etc...

So I just now created the account (by copying the brand new account i mentioned in my previous post) using the original name and email address.
I logged on to the client PC, went into Mail, created the profile (typing the login and password and ticking the remember box) and closed when finished.
I opened outlook, it connected ok (without asking for login) and I sent two emails (one internal, one external).  Received and replied from the two accounts.  Did a send and receive on this computer and my replies came in no probs.
Exited outlook, restarted the computer.
Opened outlook and it is asking for login details... again!
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Author Comment

by:Reece Dodds
ID: 35884487
Out of curiosity, I changed the password that the problem account uses (this hadn't been done yet) in the off chance that the issue was something to do with the credential recording.
After it was updated in Outlook (and remembered) the computer was restarted.
The issue still exists.
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LVL 31

Expert Comment

by:MegaNuk3
ID: 35886787
Set your Outlook authentication to NTLM instead of KEreberos and see if that makes a difference.
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Author Comment

by:Reece Dodds
ID: 35899803
just tried that... no dice!
i'm so baffled
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LVL 31

Expert Comment

by:MegaNuk3
ID: 35920956
Do Start-->Run-->keymgr.dll
and see if it shows any stored usernames, if so, delete them, then restart the PC and see if Outlook still prompts
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Author Comment

by:Reece Dodds
ID: 35928068
call me a novice, but if i do that and say... open with notepad, all i see is a bunch of characters.  If I do a find and look for the password, it finds nothing.
Is this what you mean?
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LVL 31

Expert Comment

by:MegaNuk3
ID: 35928871
I'll have to look at my instructions again. What version of Windows is the problem PC?

You should be able to go into control panel --> user accounts and there should be a 'stored passwords' option...
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LVL 7

Author Comment

by:Reece Dodds
ID: 35928903
Win7 Pro (64) currently using Outlook 2010 (it used to also run 2003 and i've tried 2007 - problem still existed).
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Accepted Solution

by:
MegaNuk3 earned 2000 total points
ID: 35937023
Try control panel --> credentials manager

See if that is storing any credentials
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LVL 7

Author Comment

by:Reece Dodds
ID: 35971271
it has to have something to do with exchange or the account (server side) surely.
 
This computer is a new custom built win7 pc with Office 2010.   It had exactly the same problem with the old computer (a 2003 build with WinXP home and Office 2003).
Not to mention that a different exchange account on this computer saves all details and works fine (see my 31 May post).
The computer is not in the same office as the server, it's 15km's away.  It has a 1500/256 ADSL connection with a brand new Netgear Modem/Router.  
Other computers in the house that have their own exchange account to the same server do not have problems, it seems to be ONLY this account.  
The only thing I haven't tried is setting up the troublesome account on one of the other PC's in the house (but i'm pretty sure that it will still have the problem).

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LVL 31

Assisted Solution

by:MegaNuk3
MegaNuk3 earned 2000 total points
ID: 35972114
Try the account on a PC in the house, that shouldn't take long to test.
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LVL 7

Author Closing Comment

by:Reece Dodds
ID: 35979963
OMFG!  it works fine on a different PC in the house.
I've gone back to MegaNuk3's suggestion and had a look... I removed everything out that was obselete or not needed and create a new Windows Credential using the domain name, username and password and then opened outlook.  No prompt.
A restart, no prompt.
Import all data from the export i did a few weeks back, restart.
No prompt.

A modem/router restart, a computer restart and...  no prompt!

Thanks soooooo much, this was a very frustrating problem and I have no idea how the credential manager was storing the wrong (or corrupt) information, but it's fixed.

Thanks again.
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LVL 31

Expert Comment

by:MegaNuk3
ID: 35980111
Glad you finally have a solution. Thanks for the points.
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