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We migrated some test users from Exchange 2007 to Exchange 2013. After Migration when we open that user from Outlook 2013 Client - it Shows Outlook Disconnected.

Now to Resolve this issue -

We go to File > Account Setting > Repair > Server Setting.

Then Manually Enter the URL of witness server of Exchange 2013. Then put username and click Check name and guess what it works.

Now my Question is why it's not picking Automatically ?

2nd when we try to open that migrated user from the browser then it never allowed us to log in. just redirected to the same URL : https://webmail.lyncsahni.com/owa

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My instinct is that you haven't got your URLs configured correctly. If both servers have been configured with the same URLs then that is your problem. Exchange 2013 cannot proxy OWA to Exchange 2007, only redirect.

Thus both servers need to have their own URLs, and if being accessed externally a unique IP address to use SSL.

Similarly, Outlook Anywhere - that will proxy between the two locations, but the host name will need to resolve to the new server.

Look at the DNS and URL configuration to begin with.

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