troubleshooting Question

Exchange 2010 and Outlook Connectivity

Avatar of Christopher Most
Christopher MostFlag for United States of America asked on
11 Comments1 Solution185 ViewsLast Modified:
Trying to connect Outlook to an existing Exchange 2010 server.  This system was setup by somebody else and the company had to move the servers.  Not only that but they had no control over DNS.  I pulled as much from the DNS as I could.  Ok, now to make matters worse, the owner decided he wanted his mail to work right away so he signed up for Godaddy hosted email and had Godaddy setup DNS for him.  Now I am trying to get things back to the way it was with the new IP address.

So this is what I have:
Exchange Server running on Windows Server 2008 R2  (Server name is Server2)
DC running on Windows Server 2012
A SSL cert with only the server name of

This was setup to go through Mail Assure from SolarWinds.  So all the old MX records pointed to their system.  By the way I moved over the old firewall and just changed the WAN IP on it.  It should be setup correctly.  I am no longer using Mail Assure.

I can connect to the OWA fine.  However I cannot get Outlook to connect.  To test I created his domain in my DNS server for testing so he can continue to work with GoDaddy until I can get this connected.  I created an autodiscover but it gets a security error since autodiscover is not in the cert name only the server name mail is in it.  (the autodiscover is a cname pointing to

I have tried to change the client properties - Outlook Anywhere from basic authentication to NTLM but that does not work.  Authentication is set to domain\user name so when Outlook asks for the password I enter it in as thedomain\user then the password that works in OWA.  I get the following error:
Logon to Exchange ActiveSync mail server (EAS): Could not locate the specified server.  User name and/or password are not valid.  Please verify the information is correct.

By the way the user domain login is first initial last name and his email is just his first name.  I am using thedomain\firstinitiallastname to try and login.  (This is what I use for OWA)

How do I get Outlook to attach to this Exchange server from the outside of this domain?  It has been a long time since I played with Exchange since most of my customers use a hosted solution now.
Edward van Biljon
(Office Apps & Services MVP | Windows Insider MVP | MCT | Author)
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