Hello everyone,
At the response to my reddit post I am also submitting my issue here.
I have inherited an ArcGIS enterprise system. Currently on 11.0 and as of March 1st, everything was working fine.
Our SSL certificate gave notice that it was going to expire, and I then learned about the lack of a direct IT department to assist with obtaining a new wildcard certificate.
I did as much research as I could, and followed numerous tutorials along with side by side installs with an esri analyst. There was some great success.
However, I can now only access my portal, server, web apps, ANYTHING related to this system on my virtual machine.