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Users getting prompted for credentials in Exchange Migration 2007 - 2010

Posted on 2013-12-20
Medium Priority
Last Modified: 2014-02-24
Hello experts,

We are in the process of moving over to exchange 2010 tomorrow actually.

Both servers are up, tomorrow we are making the changes in the DNS and in the firewall and then I will begin the moves of the mailboxes once I confirm connectivity.  

Here is my question:

In the last few days, users on laptops have been getting prompted for username/password in outlook and it won't take it no matter what they put in.  I'm not sure what it could be since we haven't made the switch yet but both servers are up and running.  I currently have owa disabled on the new server.

Any idea why all the sudden they are getting prompted?  Our users are leaving for holiday after today and I want to make sure I may not be overlooking something that will get fixed with the change over tomorrow.

Thank you,

Question by:klsphotos
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LVL 17

Expert Comment

ID: 39732474
First why is OWA disabled?
If our users do not have OWA listed in their Connections and Basic they are always prompted for passwords.
Are both servers in the sa,e domain?  May be a trust issue if not.
LVL 53

Expert Comment

by:Will Szymkowski
ID: 39732481
Are all users experiencing this issue? When the user gets prompted if you hold crtl+right click Outlook icon in the system tray and select "Connection Status" what servers are your clients authenticating to?

I would also check the Authentication settings on your users Outlook client to ensure that you are using NTLM+basic authentication.

I would also make sure that no Authentication settings on the virtual directories have been modified either. Check to make sure that authenitcation on the virtual directories is correct to remove that possibility from the equation.


Author Comment

ID: 39732504
Pjam, sorry I should have specified, I have owa disabled on the new server because I had to define the external name and didn't know since I didn't make the full switch yet if that would cause issues.

Both servers are on the same domain.

This seems to only be happening on the users who have tablets and are set in cached mode, does not seem to be happening to any of the desktops.  I will double check the virtual settings on both servers.  I haven't adjusted anything....but have a feeling it's coming from the new server?
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LVL 17

Expert Comment

ID: 39732517
Make sure they do not have saved passwords.
LVL 53

Accepted Solution

Will Szymkowski earned 2000 total points
ID: 39732522
If you use Outlook "Connection Status" you will be able to see what servers your clients are authenticating to. Make sure that it is not the old server. If you have installed the new Exchange server in the environment but have not switched over the virtual directories then your clients should continue to authenticate from the CAS/HUB server for Exchange 2007.


Author Comment

ID: 39732547
That is what I thought but the behavior offsite is doing something different and prompting in the last few days.

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