Well, tldr; I rdp'd into the server and I get no errors and it shows up under hosting server.
BUT, on my local machine:
When I go to Portal > Organization > Edit Settings, I see a 403 on:
https://maps/arcgis/sharing/proxy?https://maps:6443/arcgis/admin/data/findItems?managed=true&f=json&token=<token>
When I remove https://maps/arcgis/sharing/proxy? the findItems request works (from my desktop) and I get a response with the data store info, etc.
Portal log: "Invalid SSL certificate found. PKIX path building failed: sun.security.provider.certpath.SunCertPathBuilderException: unable to find valid certification path to requested target"
Under :7443/arcgis/portaladmin/security/sslCertificates:
I see the cert I uploaded under "Import Existing Server Cert" (which is the one I see under /sslCertificates/update)
And I see the cert I uploaded under "Import Root or Intermediate", how can I tell if it is actually using it?
Also, there are the default certs portal and samlcert.
Or is it a token issue?