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Exchange 2010 Mailbox Disconnecting From Server

Hello,
We have a problem with one of our users here.

We recently upgraded from Exchange 2003 to 2010. We now have 2 exchange servers running in a DAG configuration with the exchange 2003 running as a legacy server.

We have about 400 users that we have migrated from the old exchange 2003 server to the 2010 servers using the move mailbox tool in exchange 2010.

We have a user whose mailbox is having a few issues. This user’s mailbox was migrated from the old to the new exchange successfully. The user’s mailbox started showing as disconnected in outlook 2007 constantly. We move the user to another mailbox store but the same issue occurred.  I ended up backing up his PST and deleting his mailbox.
I was having a few issues trying to create a new mailbox for him on the 2010 servers so I created his mailbox on the 2003 exchange server. Once created, I moved it to the 2010 exchange server(s).  Once there I merged the contents from his PST into his new mailbox. After using his mailbox for a half day it started prompting for username and password to access the exchange 2010 server. When we enter it, the mailbox starts to receive mail.  Another issue has popped up now where his status in Outlook is “Trying to connect to exchange”. The only way I have been able to fix this is to reboot the laptop. We have tried moving his mailbox to another store but no result.

Has anyone ever seen something like this or have a solution.

Any advice is appreciated.

Thanks
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post_university
Asked:
post_university
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1 Solution
 
akhalighiCommented:
I'd delete and re-create his outlook profile. have you tried that ?
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post_universityAuthor Commented:
Yes we have tried a different profile within outlook and in Windows.

When I say windows I mean I logged him out, changed his profile name to username.old and had him log back in. This created a new Windows profile for him. But still no result.

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5g6tdcv4Commented:
1.      in the systray (notification area near clock) locate the outlook icon
2.      Press the CTRL key, and then right-click this icon.
3.      Click Connection Status.
4.     What is the status of the GC and exchange server?
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post_universityAuthor Commented:
It shows 3 connections, all connected to our cas server, 2 mail and 1 directory connection
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akhalighiCommented:
No .. I am not talking about windows profile , I am talking about outlook profile under his control panle > mail.
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post_universityAuthor Commented:
Yes that has been done as well
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akhalighiCommented:
So .. now his mail box is no more disconnected but he gets an extra prompt , is that right ?

does he have outlook auto login program installed ? some times old outlook password gets cached somewhere . I had the same issue on a windows 7 machine and once I removed all cached credentials , outlook stoped prompting for password.
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5g6tdcv4Commented:
If this is only happening to one user after your migration it has to be a network issue
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