I recently migrated our 2007 Exchange Server to 2013.  This is a single server setup.  Everything seemed to go fairly well.  I've been through many Exchange migrations in the past, but this is the first one that has been 2007 to 2013.  This environment has also been migrated from 2003 to 2007 in the past (not me) and the Exchange 2003 server was never decommissioned properly.  So...  I've removed the 'first administrative group' from ADSI Edit which enabled me to install Exchange 2013 without it thinking there was a legacy 2003 server installed.

Once I got everything setup I moved all mailboxes have been moved to the new 2013 server, set all URLs to the respective domain names, installed the new cert.  Pretty much followed a guide i found online for an Exchange 2007 to 2013 migration.  Everything with 2013 seems to be functioning correctly.  I have mailflow between 2007 and 2013, i have mailflow to external addresses, mailflow in from external.  OWA functions properly, ActiveSync for all of my mobile devices seems to be working just fine.

Here's my one (major) issue:

My Outlook Clients are now asking for credentials upon launch and then about every 10 mins or so thereafter.  At first i was testing with my account and Outlook Client (2013).  Then decided to test with Outlook 2010.  Same issue on both clients.  After a lot of searching on this particular issue, I found a possible cause of the issue, but cannot for the life of me seem to fix it...

I've found multiple posts stating that this issue is related to the OAB connection.  This was confirmed by noticing Outlook was trying to download the OAB everytime the authentication box would pop up under the Local Mailbox tab on the Connection Status option using the ctrl+rightclicking the outlook icon in the notification area.

Also, i've noticed if i hit 'cancel' to the authentication request, Outlook functions just fine.  All folders are updated, however the request does come back.  It also shows 'need password' in the bottom right of Outlook.  It also doesn't matter how many times i enter the correct user and password it doesn't take it.  (yes, password is correct and yes, i've entered user name as domain\username, just username and username@domain).

So, I started investigating the OAB issue.

The first thing i did was verify i have an OAB.. I did... There was the default one with 2007 and there was a new one for 2013.  I did try and do a move-offlineaddressbook request during the migration process and it failed stating I couldn't move an old OAB to Exchange 2013 i had to create a new one.  So i removed the (already new) exchange 2013 OAB, and created my own and made it default.  Still no change in behavior.  I verified the internal and external URLs for the virtual directory they are correct (https://mail.domain.com/oab) and the virtual directory is linked to the OAB. 

One thing i did notice that was odd was when i do a get-offlineaddressbook | fl, on my new OAB i notice that there is a property called OriginatingServer and it was pointed to my old 2007 server FQDN, not the new 2013 one.  I found that odd that it wouldn't originate from 2013 especially when I created the OAB from the 2013 server....

My next step was to just kill all services to the 2007 box...  Essentially shutting down the old 2007 exchange server.  Everything was moved so i should be able to use it solely off 2013.  Once i did this, my Outlook 2010 clients seemed to function just fine, no long requiring username and password.  Score!  I then i tried Outlook 2013 thinking the issue would be remedied once i uninstall and decommission 2007....  WRONG.  Outlook 2013 is now broken.. I get the following error when starting Outlook 2013:

Cannot Start Microsoft Outlook.  Cannot open the Outlook window.  The set of folders cannot be opened.  The attempt to login to Microsoft Exchange has failed.

I started all 2007 services up again and Outlook 2013 is still jacked up.  Outlook 2010 is back to asking for credentials.  My worry is this:  SOMETHING is still tied to Exchange 2007.  I'm guessing it's with OAB, but no clue if that's it.

Oh  I also looked for the arbitration mailboxes for OAB, they are on the new server and i have none on the old 2007 server.  I'm at such a loss at this point.  Can anyone help me??

Thanks!

Also looked at logs on the 2013 server in the following location:  %exchangeinstalllocation%\logging\httpproxy\oab

Opening up any of those logs reveals that any connecting IP that is related to an Outlook Client is showing 401 for httpstatus.  Not sure what that means, but there are blank lines for each of these lines all the way across... basically it's telling me it's not connecting.

Test-outlookwebservices shows successful for everything.

I've checked into about everything, but if someone needs more info, just ask.  Everything seems to check out for me, with the exception of that 'OriginatingServer' property under the get-offlineaddressbook | fl is showing the old 2007 server by default when a new OAB gets created.

Did you move the Public Folders?

I tried... it didn't work... but we don't use them anyway, so it's not a huge problem if we don't have them...  but i would like get them if i could, just in case....  You think that's what is causing the issue?

I think the problem is with the Public folders.  I shut down that old server and I noticed that Outlook doesn't prompt for the password anymore, but there is still a connection active to try and connect to my old 2007 server.

does anyone have a good way to migrate PFs to 2013 from 2007?  The instructions i followed didn't work.. it included downloading some scripts from Microsoft and exporting some csv files from 2007 then using those to do the migration on 2013...  Mine ended with a 'Failed' status in the shell, but i had no way of knowing exactly WHY...

i'd post the links i've all used, but cannot do that for some reason.. something about my account not being verified, which I thought it was.,.,

Exactly.

Your Public Folders are still on Exchange 2007 and your clients are trying to connect to them.

Here is an article that would help you to do PF migration

http://social.technet.microsoft.com/Forums/exchange/en-US/99a73f6a-f5b6-44d2-aa43-1bc1f4b0651a/users-connecting-to-legacy-exchange-server-for-public-folders?forum=exchangesvrgeneral

Hi,

Have you replicated all the system folders in the Public Folder to the Exchange 2013 server, especially for the EFORMS REGISTRY folder since the Outlook will try to access this folder when loading and Organization Forms templates.

Happy New Year!

Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Subscriber Support, contact tnsfl@microsoft.com

Hi,

Is there any update on this thread?

Regards,

Please remember to mark the replies as answers if they help and unmark them if they provide no help. If you have feedback for TechNet Subscriber Support, contact tnsfl@microsoft.com

I don't know if this will get to you, but I have the exact same issue.  I have not done the migration yet, but I am guessing that you followed a similar guide as I am planning to do. I have performed all of the prerequisites.  Somewhere along the line, it tells you to make the new server the OAB generation server.  I did this.  One of the next steps is to migrate the Public folders.  The guide I had had a bunch of PowerShell scripts and such, and I couldn't make heads or tails of it. The only exception is that I am doing a two-tier migration.  The first step is to get the mail and CAS, HT roles off of the old server, which is physical, and already had a RAID fail.  I am moving it to an existing 2007 server that is virtual.  The plan is to migrate then to the new server that is 2013 (not built yet).  All the mailboxes are moved from the old server to the virtual 2007 server.  I am in the process of moving the mail flow.  I created a Public folder to synch with the old one, and set up replication.  Evidently it is not working correctly.  Half the people get prompted for credentials.

How did you solve your issue?