Outlook 2013 Clients certificate has expired warning or not yet valid

Hello,
We had been through a migration from exchange 2010 to 2013 in the last year but have had an ongoing issue with
some Outlook clients getting a certificate warning after they launch the client. Not all Outlook clients experience this. We've just recently uninstalled exchange from our 2010 servers and shut them
down. What we have left are two 2013 servers in a DAG. The certificate these Outlook clients are complaining about had expired in 2012. Here is the warning they are getting:
"Certificate has expired warning or not yet valid"
I've been through numerous threads/sites regarding this error but it always ends up that there was an expired cert hanging out somewhere. I cannot seem to find an expired cert anywhere...
I've ran the 'Get-ExchangeCertificate | fl' cmdlet and I see 7 certs listed, none of which match the thumbprint on the Cert Warning on Outlook.
When I check the registry of the Exchange servers here: HKLM>Software>Microsoft>SystemCertificates>My>Certificates
I can see 7 certificate entries listed there and the thumbprint matches those of the cmdlet ran from
EMS.
OWA shows the correct cert expiring in 2015 and Outlook clients are pointed to the 2013 servers. We do have a load balancer that AutoDiscover, OWA, SMTP are going through.
It seems like some of these Outlook clients are still looking at the decommissioned 2010 Exchange servers' old certificate. Any ideas on how I can get outlook to point to the new certificate/server?
Thanks.
Rory
Rory Schmitz

Hi Rory,
If possible, could you please post the Get-ExchangeCertificate | FL results about the certificate which is assigned with IIS service here?
If the issue only happens for some users instead of all users, please create a new Outlook profile for the problematic user to check whether the issue persists. Please make sure the certificate name which is reported as expired or not valid is included
in the IIS service certificate in your Exchange 2013.
In Exchange server side, please restart IIS service by running IISReset /noforce from a command prompt window to have a try.
Regards,
Winnie Liang
TechNet Community Support

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