Exchange 2013 to Exchange 2010 Outlook redirect

Hi Experts,

I have a slightly annoying issue that I can't resolve.

I'm in the process of migrating from Exchange 2010 to Exchange 2013.  I have 2 environments (dev & live).

I have successfully built my dev environment and tested every possible scenario successfully, including the issue I am having with my Live environment.

My issue is that all connections are now pointing to my Exchange 2013 Multirole server.

When starting up Outlook with my test user in the Live environment, Outlook can't connect and asks for the server name and user, but if I login into the test user account via OWA, I am redirected to the users account on Exchange 2010 (which is what I expect) but I don't get the same behavior with Outlook.

The only difference between my dev and live is the DNS.  In Live I have split DNS ( &  The servers live in and the autodiscover/owa etc DNS Records live in, but as we are keeping the same URL's all I have done is change the IP address & all configuration has been done following the Exchange Deployment Assistant.

Can anyone shed any light on what i'm doing wrong?  If you need more information please let me know.
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Simon Butler (Sembee)ConsultantCommented:
Do you have different URLs for the two versions of Exchange?
If not, then that is probably some of the problems. Not everything will proxy, some will redirect.

The internal Autodiscover URL can be the same on both servers (usually pointing to the later version). However Outlook Anywhere should either have no external URL configured on Exchange 2010, or a different URL.

The most common reason for connection failures is authentication mismatch between the two versions, SSL certificate issues or URL configuration incorrect.

What about Public Folders? Do you have Public Folders on Exchange 2010? Those can cause connection problems.

novatekitsolutionsAuthor Commented:
Hi Simon,

I do have different URLs for the 2 versions, mail for Exchange 2013 and legacy for Exchange 2010.

Thanks for the insight, i'll double check my URLs for mismatches, and also the authentication methods.  My External Outlook Anywhere URL for Exchange is different on Exchange 2010.

As for Public Folders, Yes I do have Public Folders on the Exchange 2010 server, i'll look into these a little more as well.

I'll report back once i've checked everything over again.


novatekitsolutionsAuthor Commented:
Hi Simon,

I configured a different URL for Outlook Anywhere and confirmed all the URLs are correct as well as confirming all the Authentication methods are the same on all URL's and Outlook Anywhere, but I still get the same issue.

I've followed the Exchange 2013 Deployment Assistant again and confirmed that all is correct, but I still get the same issue  with Outlook connections.
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Simon Butler (Sembee)ConsultantCommented:
What about public folders?
Have you checked what the public folder database configuration is on the new server?
Eliminating public folders completely makes a migration much easier though.

novatekitsolutionsAuthor Commented:
Hi Simon,

I have no Public Folders configured on the new server.

My plan is to leave that on the old server until I have got the redirect working.
Simon Butler (Sembee)ConsultantCommented:
I didn't mean public folders on the new server.
On the properties of the database on the new server you need to set a public folder database IF you have public folders on the old server.

novatekitsolutionsAuthor Commented:
I've now rebuilt the Exchange 2013 server and all is working as expected.

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novatekitsolutionsAuthor Commented:
I wasn't getting to the root of the issue, therefore I uninstalled Exchange 2013 and rebuilt the server and now working as expected.
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