What port is being used for the "Check for ArcGIS Enterprise Updates" utility? We opened 443 in our firewall on a usually disconnected server, and can hit www.arcgis.com:443 in Internet Explorer. But the tool returns an error:
Your computer appears to be offline. Check your Internet connection and try again.
Network connection error.
I am currently experiencing this same issue on newly installed portal systems, version 10.9.1.