Autodiscover/Outlook anywhere fails when using a wildcard certificate
A very common issue faced with people who buy a wildcard certificates is that Autodiscover and Outlook Anywhere will not work because the Certificate Principal Name *.domain.comdoesn’t match the name returned by the autodiscover service server.domain.com
This issue is a pretty easy fix it is enough to run from Exchange Management Shell to match the Certificate Principal Name with the setting returned by the autodiscover service.
Set-OutlookProvider -Identity EXPR -CertPrincipalName msstd:*.domain.com
You can verify the changes you have done by running