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JScho10
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Some Outlook 2007 Clients ask to login after upgrade to new Exchange 2010 server.

I upgraded to a new Exchange 2010 server on a new machine.  Had an old Exhange 2007 server running which is DC.  Transfered all the mailboxes etc. to new Exch 2010.  Everything worked fine on new server until I uninstalled Exch 2007 on the old server.  Followed the technets for "Completely Removing Exchange 2007 from a Server".  Now some (not all) Outlook 2007 clients ask to login.  After login everything works. The old exhange 2007 continues to be the DC.  

Where should I start for fixing this?
ExchangeOutlook

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JScho10

8/22/2022 - Mon
Manpreet SIngh Khatra

You can try to create new Outlook profile as that should solve the issue .... hope no Host files or Cached credentials causing the issue

- Rancy
JScho10

ASKER
Created new Outlook profile.  New profile still asks for login everytime I re-start Outlook.  Host files? Cashed credentials?
Manpreet SIngh Khatra

On the client machine it shouldnt be pointing to some IP in the host files and hope no cached credentials .... what is the client OS ?

- Rancy
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JScho10

ASKER
Windows 7 Pro 64 bit.
Manpreet SIngh Khatra

http://itknowledgeexchange.techtarget.com/network-administrator/how-to-clear-cached-credentials-on-a-windows/

Please be cautious if user has some cached credentials for some App that he doesnt remembers
JScho10

ASKER
The only cached credentials were (3) TRMSVR/<server name>.  The new Exchange 2010 server was not listed.  I deleted all.  No joy.
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Manpreet SIngh Khatra

Ohk lets get advanced ...

Create a new machine profile for this user and try with Outlook profile in there .... also few things are all affected users on same Database or something common ?

- Rancy
JScho10

ASKER
It's down to two clients now. One W7 and one XP.  On another W7 a new Outlook profile apparently worked.  There is only one exchange database.  We have two sites though and it seems that the clients with problems are at this site where the orginal Exch 2007 server was which has been the DC (secondary), DNS, and DHCP.

I am in the process of promoting a new server (not the new Exch 2010 on this site) to DC (secondary), DNS, and DHCP on this site.  Then take down the old Exch 2007 server.

I'm going to the the new machine profile then if I still have the problem.

I will let you know how it goes.  Thanks for your help so far!
Exchange_Geek

If it prompts for the password - for just one mailbox, here are simple steps for you.

Create the OL profile of this user on another machine which has never complained.
If the issue is seen on the other machine too - then the problem is with the mailbox
If the issue isn't seen on the other machine - then the problem was with the earlier machine.

Ways and means are many to fix OL issues, personally I'd simply flatten the box and get it up and running with brand new O/S and stuff in max 2hrs and quit checking millions of places and rather spend time on production-hampering issues. But that's just me :)

Regards,
Exchange_Geek
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JScho10

ASKER
One was fixed by installing a new computer, and (2) were fixed by deleting and recreating a new OL profile.

Now its down to one I just started having problems in the last 2 days.  I've tried deleting the OL profile and reinstalling.  But keeps intemittantly asking for login which it won't accept.  After a few restarts it may work.  BTW also when it does finally connect it warns that the 3rd party SSL cert is incorrect.

My thought is to create a new XP Pro profile on this machine.  My questions are:
Should I create a new machine ID?
Should I create a new mailbox?  If so what is the best way to transfer the contents of the old mailbox to the new mailbox?

Thanks.
Manpreet SIngh Khatra

Should I create a new machine ID? - You mean new Machine profile for the user ... if so yes please

Should I create a new mailbox?  If so what is the best way to transfer the contents of the old mailbox to the new mailbox? - Export data to PST create new Mailbox in Exchange and then check if its working firstly

- Rancy
SOLUTION
Exchange_Geek

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JScho10

ASKER
On this last computer that I have been having problems with, I took your advice and installed a brand new computer with W7 Pro.  I even created a new user and new mail box, and had no problems until I imported the .pst backup.  After importing, the same problem came back.  Asking me to login which it won't accept the password.  I did notice that it was showing my external mail server FQDN, mail.<domainname>.com which it should not be be asking for.

After digging around the profile I noticed that in the Outlook Microsoft Exchange settings of the workstation, in the connections tab, the Outlook Anywhere "Connect to Microsoft Exchange using HTTP" button was checked.  In the exchange proxy setting of that it showed my external mail server FQDN  mail.<domainname>.com.

I unchecked the "Connect to Exchange using HTTP" and restarted Outlook and the workstation immediately connected.  However, when I closed Outlook and tried to connect again I got the login again.  I went to the profile and the Outlook Anywhere "Connect ... HTTP" button was mysteriously checked again.

I tried deleting the profile and restarting but the Outlook Anywhere button keeps getting checked.

What should I do?  I don't use "connect using HTTP" on my local clients, only than Web OWA for external internet users.
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JScho10

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Had to contact Microsoft for the solution.