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New Exchange server 2013 not allowing Outlook to connect

Luuker asked
Last Modified: 2017-12-07
I have been in this business now for 15 years. I have admin'd multiple Exchange servers over the years but I have never set one up for production from scratch. This makes me a semi-noob. I have been fighting an issue for 2 weeks now and need help!

A new Exchange 2013 installation on a dedicated Microsoft Server 2012. I have purchased and attached a registered SSL cert for the mail server. Exchange itself is running fine. I have created multiple email boxes for users and email works perfectly. Each user can log in to OWA and the mail works as it should. They can all send and receive with no problems or delays. This holds true from inside OR outside the office.  

I am not able to connect Outlook to any mailbox though.

When using Microsoft Remote Connectivity Analyzer, I get mixed results each time I run the various parts.

When I run Exchange Activesync Autodiscover, I get Connectivity Test Successful with Warnings.

When I run Exchange Activesync, I get Connectivity Test Successful with Warnings.

When I run Outlook Autodiscover, I get Connectivity Test Successful with Warnings.

When I run Outlook Connectivity, I get

"Certificate name validation failed.
      Additional Details
Host name mail1.domain.com doesn't match any name found on the server certificate CN=mail.domain.com, OU=PositiveSSL Multi-Domain, OU=Domain Control Validated.
Elapsed Time: 0 ms."

I have a multi domain cert and 3 domains listed so far: domain.com, mail.domain.com, and autodiscover.domain.com. I am not sure if this really is a cert issue, or if there is something I missed in the install.

If I ignore all of this, and try to configure Outlook, after putting in the information asked during setup, Outlook appears to take 3 steps:
1. Establish network connection
2. Searching for "mailbox" settings
3. Logging on to the mail server.

The first two steps work fine and I get the green checkmark. The third step fails however and throws the error "The action cannot be completed. The connection to Microsoft Exchange is unavailable. Outlook must be online to connected to complete this action."

I get the same error no matter in the office or out.

Can anyone help? My head hurts from pounding it against the desk!
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