I recently upgraded from Exchange 2010 to 2016. I am having a weird issue. I have configured a dozen 2016 servers for other environments without issue, so I am almost certain the server side is correct. That being said, all Outlook 2013 clients will only connect via cached mode. When I create a new profile without cached mode, Outlook will only open the initial time. After that, I get this error every time:
Cannot start MS Outlook. Cannot open the Outlook Window. The set of folders cannot be opened. The information store could not be opened.
I am also getting a certificate error:
The name on the security certificate is invalid or does not match the name of the site.
I ran the internal certificate test however, and the server side is correct.