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Exchange 2013 with Exchange 2010 - outlook 2010 not setting up

I've installed Exchange 2013 with Exchange 2010.  

The install worked great, the 2013 server is up, and OWA is working great.

But Outlook 2010 will not auto connect to it.  Either when I setup a new profile, or after I move a mailbox on an existing profile.

If I go in an manually setup the HTTP settings, outlook will connect.

Any ideas on why outlook will not connect?
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1 Solution
Does your autodiscover record in DNS point to the 2013 CAS?
erikwhitewayAuthor Commented:
Autodiscover Cname to the 2013 host name for internal DNS.

Both servers have an external name of Mail.company.com - so I just changed the internal DNS to point mail. at the new server.
erikwhitewayAuthor Commented:
Moving mail. to the new 2013 server seemed to make outlook connect.  But it's putting up a login prompt to users.
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Simon Butler (Sembee)ConsultantCommented:
Autodiscover doesn't work in the same way internally.
What do you get from this command?

get-clientaccessserver | select identity, AutodiscoverServiceInternalURI

If you are migrating to Exchange 2013 then I would probably have the same URL on both servers, pointing to the Exchange 2013 URL, or a host name that resolves there which is also on the SSL certificate.

Authentication prompts can be an indication of an SSL certificate issue. Do you have a trusted SSL certificate on the Exchange 2013 server?

erikwhitewayAuthor Commented:
Each server has it's self as the autodiscover (internal full dns name).

Another issue:


On the old server - only shows the old server - does not list the new one.

Same with the autodiscover list.
erikwhitewayAuthor Commented:
Also have issue that the test moved mailboxes can't send mail to boxes on the old server:

Diagnostic information for administrators:
Generating server: MAIL1.c.com
Receiving server: MAIL.c.com (
Remote Server at MAIL.c.com ( returned '400 4.4.7 Message delayed'
9/13/2013 12:09:01 AM - Remote Server at MAIL.cosmospecialtyfibers.com ( returned '451 4.4.0 Primary target IP address responded with: "451 5.7.3 Cannot achieve Exchange Server authentication." Attempted failover to alternate host, but that did not succeed. Either there are no alternate hosts, or delivery failed to all alternate hosts. The last endpoint attempted was'
erikwhitewayAuthor Commented:
I've found the command to reset Autodiscover to autodiscover..com  And in DNS that points to the new 2013 server.

I also made a receive connector in 2010 just for the 2013 server.

Things seem to be working better now.
erikwhitewayAuthor Commented:
needed setup on both servers
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