Exchange 2007 to 2013 migration - Outlook keeps prompting for password

Did an Exchange 2007 to 2013 migration and everything seems fine on the mail flow side of things, but all of the clients are getting a password prompt when starting Outlook. I have a feeling it is something to do with Outlook Anywhere.

There is a DNS entry for (same as external FQDN) and it resolves fine. The Microsoft connectivity analyzer passes.

Where can I begin with this?
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Will SzymkowskiSenior Solution ArchitectCommented:
For a user that is getting prompted like this do the following...
- open Outlook
- Hold CTRL + Right click the Outlook icon in the System Tray
- Select Test Email Auto Configuration

make sure that the clients are pointing to the correct URL's for Exchange.

Also have you migrated your public folders? I have seen issues where users are authenticating to public folders that are still on Exchange 2007.


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mvalpredaAuthor Commented:
Checking public folders now. Why would it ask for a password if the public folders are still there? The 2007 machine is still online and all services started....just all mailboxes moved.
Will SzymkowskiSenior Solution ArchitectCommented:
I remember doing a migration from 2007 to 2013 and Public Folders was the cause of the password prompting. Also what are you using for your virtual directoires on Exchange 2007 and 2013?

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mvalpredaAuthor Commented:
Which virtual directories? Everything is pointed to and points to the IP of the 2013 server. We have a commercial SSL certificate.
Simon Butler (Sembee)ConsultantCommented:
Have you configured both servers with the same URL?
That can cause these problems because it is looping back on itself.
If Outlook Anywhere is enabled on the Exchange 2007 server then ensure it is using a unique URL. If users have been moved off that server, then disable Outlook Anywhere completely.

mvalpredaAuthor Commented:
Going to turn off OA on the 2007 machine.
mvalpredaAuthor Commented:
Now I am getting this:

Cannot open your default e-mail folders.  You must connect to Microsoft Exchange with the current profile before you can synchronize your folders with your Outlook data file (.ost)."

New users are fine. Tried restarting the Microsoft Exchange Client RPC Access service with the same results.
mvalpredaAuthor Commented:
I take that back, new users are not fine. Outlook says it cannot open default email folders. Microsoft Exchange server is not available.

I look at the profile, and the Exchange server shows
Will SzymkowskiSenior Solution ArchitectCommented:
Did you try checking the auto discover settings in my first post for your Outlook clients?

mvalpredaAuthor Commented:
Of all the crazy things on this.....someone had locked down the RPC over HTTP vdir in IIS on the 2007 machine. Once that was fixed everything fell right into place.
Will SzymkowskiSenior Solution ArchitectCommented:
Glad, you got this sorted out.

mvalpredaAuthor Commented:
Not really a solution, but thanks for the help. :)
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