Outlook 2013 and SBS 2011 - Changing cert on server

Posted on 2016-10-30
Last Modified: 2016-11-08
I have a customer that has a SBS 2011 Server (using Exchange) and Outlook 2013 on the Workstations. Essentially they decided to change the SSL Certificate on the server. At that point when they open Outlook on the workstations they get an error about the SSL certificate not matching (it is looking for the old certificate).

It seems like it only happens once when they first open Outlook and then the error goes away. I have even tried rebooting a workstation and the error does not appear to come back. I understand why the error occurred but can't figure out why it went away.  

Where does Outlook store the certificates and did the error truly go away or is it going to pop up again?
Question by:LockDown32
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Expert Comment

ID: 41866213
HI LockDown32.

What message is the SSL warning reporting.  Its should say if its a name mismatch, or expired or........

Also did they use the SSL Certificate wizard in SBS to create the cert req, and install the new cert.
LVL 15

Author Comment

ID: 41866220
It is a name mismatch which is expected. They changed the name on the cert. Generated the CSR in the SBS Console, submitted the CSR to GoDaddy and downloaded and installed in via the SBS Console.

Expert Comment

ID: 41866225
Have they changed the Internet Domain Name ?

If yes, did they use the Domain Name Wizard to reset the internet domain name in SBS
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Author Comment

ID: 41866239
Yes. All of this was done with the SBS console. First they changed the Internet Domain Name then they chaned the certificate to match the new Internet domain name.

Expert Comment

ID: 41866240
Have you tried the following
  1. Create a new user with a mailbox, and log onto a PC as that user to see if the error is coming from the config in the exchange profile.
  2. Connect to OWA and see if it is reporting the same error
  3. If there are sufficient workstations, pick a user who hasn't logged onto a workstation and have them log on and see if the msg appears
  4. Run fix my network and see

I don't have many SBS clients (half dozen or so) and I have the same exercise coming to rename their internet domain and was told by MS support to use the wizard and all will be fine, but it appears you may prove that advice to be incorrect
LVL 15

Accepted Solution

LockDown32 earned 0 total points
ID: 41872688
The solution was to delete the Outlook Profile and re-create it with the new cert name/email address
LVL 15

Author Closing Comment

ID: 41878477
This is the solution that worked

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