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Badger3k
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join:2001-09-27
Franklin, OH

Badger3k

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Outlook 2007 & Exchange 2010 prompting for username/password

Just recently migrated a client to Exchange 2010 and 1 user with Outlook 2007 gets prompted for his username/password every time Outlook opens and then randomly through out the day while he is working. Sending & receiving email is fine, so its not keeping him from his work, but it's really annoying.

The address that is prompting is the OAB/Outlook Anywhere/OWA address so its hard to find out what specifically it wants to do, but I'm guessing it has to do with the OAB. Putting in his password and checking remember doesn't work, the next time he opens Outlook it just prompts again. Tried to create a new profile, Autodiscover picked up who he was and everything without any prompts, but as soon as it started downloading his mailbox he was prompted.

I've read some posts that the authentication can be screwed up on the Exchange server in IIS, but I'm hesitant to start changing anything there since this is only happening to 1 user out of 25 or so. I do see the failed logon attempts (he just keeps hitting cancel) in the Security log on the exchange server. What else can I try? Does it sound like an Outlook issue or something on the server?
lorennerol
Premium Member
join:2003-10-29
Seattle, WA

lorennerol

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Sounds like an incorrect saved password to me, or a DNS/AD issue.

Clear any saved passwords on the PC, reboot, and see if the problem persists. Also ask if he has his mailbox setup anywhere else (another PC with an Outlook profile, a mobile device, etc).

DC DSL
There's a reason I'm Command.
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join:2000-07-30
Washington, DC
Actiontec GT784WN

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Sounds like OAB is looking for the old server. Make sure anything local to Outlook is backed-up, create a local Outlook file, drop Exchange from the profile (pointing the inbox to the local file). Restart Outlook, re-add Exchange and point the inbox back to it. That *should* cure it.

Badger3k
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He does have a Windows Mobile phone, however that is not having any issues.

I'll try these and post back with the results. Thanks!

jfgnet
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join:2001-02-14
Limbo

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Make sure this is not checked

Badger3k
We Don't Need No Stinkin Badgers
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join:2001-09-27
Franklin, OH

Badger3k

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I've tried unchecking that and it didn't seem to make any difference.

jfgnet
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join:2001-02-14
Limbo

jfgnet

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Have him logon to the prompt once with DOMAIN\USERNAME and his domain password and make sure as my previous post shows that http section is unchecked
lorennerol
Premium Member
join:2003-10-29
Seattle, WA

lorennerol

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If the computer is domain-joined and the Outlook mailbox matches the logged in user, there shouldn't be a login prompt when Outlook opens, unless it is using RPC over HTTP to connect.
tomdlgns
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join:2003-03-21

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i would try not using auto discovery and enter in the settings manually.
Anon00
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join:2001-09-25
USA

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said by lorennerol:

If the computer is domain-joined and the Outlook mailbox matches the logged in user, there shouldn't be a login prompt when Outlook opens, unless it is using RPC over HTTP to connect.
Which you can verify with outlook /rpcdiag

Does it only happen when they have a particular e-mail in view (or replying/forwarding/etc)? I seem to recall an issue I've seen once or twice where an embedded image is referencing another internal person's e-mail account (OWA address). I can't recall the exact scenario, I think someone from the outside embedded an image then the internal recipient, from OWA, forwarded to someone else that was internal and then that person would get the prompt.

jester121
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join:2003-08-09
Lake Zurich, IL

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Also check and see what authentication is being used for the OAB in Exchange. There are some very particular steps that are easy to miss in the 2010 setup and I ran into this on one of our test boxes. I think changing the authentication fixed it (let me know if you need more info).
joshg409
join:2005-05-03
Ottumwa, IA

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Look in the sync issues folder in the outlook client. There will be an error code in the messages. Look that up, it has something to do with an incorrectly formatted OAB location in active directory if i remember correctly.

fcisler
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join:2004-06-14
Riverhead, NY

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your autodiscovery settings are botched, or your mailbox server is incorrectly set, or you've messed with permissions on IIS.

Those are top 3 reasons you'll be getting those errors.

First thing? Exchange command shell

Get-ClientAccessServer | fl

examine for any errors

After that look through the Client Access Cmdlets:

»technet.microsoft.com/en ··· 157.aspx

Change only ONE thing at a time, and write down what you changed.

Also - if you have done ANYTHING with IIS undo it or reset it before trying any of these commands.

EDIT: Upon reading your post further; you've f*cked with IIS. Undo whatever you did. I'd hedge a bet on the host header for IIS or permissions. When you run the Get-ClientAccessServer it should return a URL in one of the paramaters - make sure you can access it from the exchange server AND the client PC. If you cannot - there's step 1 troubleshooting.