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Certificate Issue on Exchange 2016

Posted on 2016-08-21
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Last Modified: 2016-09-22
Single server Exchange 2016 installation.

Server is using a self-issued cert.

The cert is installed on all the workstations in the Trusted Root Certification Store, but all Outlook users are prompted at start to accept the cert with the 3rd option in the security Alert dialog redX’d “The name on the security certificate is invalid or does not match the name of the site”.

The name on the cert is the same as the host name of their MX record.

If an external user, without the cert, attempts to access OWA using IE, they get the expected certificate waring, but if they install the cert, then OWA logs in without the warning, so I believe the cert works OK.

If Outlook users OK through the Security Alert dialog, they connect OK and are not prompted again for the remainder of the Outlook session.

Any ideas to fix this?

I’ve looked at bindings in IIS, and they all use that cert.

If I do get-ExchangeCertificate in EMS, services I,P,W & S are bound to the cert in question, which is consistent with other Exchange Servers I’ve checked on.

Any ideas?
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Question by:snooflehammer
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Accepted Solution

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Todd Nelson earned 500 total points
ID: 41764622
You will need to create a certificate request from the Exchange server and purchase a UCC/SAN certificate from a public certificate authority (CA) like Digicert or GoDaddy.

https://www.digicert.com/unified-communications-ssl-tls.htm
https://www.godaddy.com/web-security/ssl-certificate

https://oddytee.wordpress.com/2014/09/09/exchange-2013-certificate-commands/
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Author Comment

by:snooflehammer
ID: 41764624
I plan to do that next time I've got some down time, but I just need to keep this working for a week or more. I can't risk bringing Exchange down at the moment.

Looking for a workaround to stop the cert pop-up message.
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Expert Comment

by:Sushil Sonawane
ID: 41764894
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Author Comment

by:snooflehammer
ID: 41771024
Thanks guys!
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Expert Comment

by:Todd Nelson
ID: 41790519
Snooflehammer,

Do you have an update for us?
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Author Comment

by:snooflehammer
ID: 41790530
Got a Godaddy cert
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LVL 15

Expert Comment

by:Todd Nelson
ID: 41811771
Hopefully the publicly trusted CA cert is working out for you. Please award points appropriately to close your resolved question.
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