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Cannot connect outlook 2016 to Exchange 2016

Posted on 2016-10-13
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Last Modified: 2016-10-17
I'm setting up a new domain with windows server 2012 R2 and exchange 2016.  I've created a self-signed certificate with all my domain/sub-domain names on it and DNS records for the system name, autoconnect, and mail cname.

OWA works and using that I can send email to and from a gmail account and internally to two test users I created.

I'm trying to connect with outlook 2016 and receive the error "log onto exchange activesync mail server (EAS): Could not locate the specified server.  Username and/or password are not valid.  Please verify the information is correct."

I've verified the information and tried changing passwords.  To be sure I entered the wrong password and received a different message altogether so I'm assuming this is not a username / password problem.

I used the Microsoft Remote Connectivity Analyzer website and it passes all of the tests except the outlook connectivity test which doesn't like my certificate, test attached.

Is this still a certificate issue?  I've gone through a ton of articles online none of which have helped.
Microsoft-outlook-connectivity-test.html
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Question by:paulc
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Ivan earned 500 total points
ID: 41842509
Hi,

how did you configure that Outlook? You cannot set it up manually.
When you run it, you have to enter your name, email address and password. You cannot choose option "manual setup or additional server settings".

So, when you type in those info, what error do you get?
Did you import self signed cert to your client machine? Can you try to use this guide for it: https://www.orbitsit.co.uk/2014/08/deploy-self-signed-exchange-certificate-pcs-avoid-outlook-security-alerts/

PS: You don't have internal CA deployed, this is just self signed cert on exchange?

Regards,
Ivan.
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by:paulc
ID: 41846686
I came back to it this morning and everything is working.  I didn't touch it since Thursday so I have no explanation why it is working now.  It makes me a little nervous to deploy but I'm moving on.  Thanks for the help.
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Expert Comment

by:Ivan
ID: 41846750
One of those strange things :)
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