Thanks for the screen captures.
1. Make sure your Numerical Cloud "Activation Code" has been properly activated - so far nothing has been done.
2. Have you searched and selected EasyGerb from it's installation folder (default: C:\Numerical Innovations\EasyGerb7\). AutoCAD won't load EasyGerb automatically unless you place it in the "startup suite". https://support.numericalinnovations.com/a/forums/topics/14000011756
3. Try a different version of AutoCAD (if possible). We've been supporting EasyGerb since AutoCAD 2000, so over the years some releases are more friendly/compatible than others - specifically newer versions which have increased security protocols preventing access for ARX binaries.
4. Since you have Numerical Cloud - both FAB 3000 and ACE 3000 can convert any AutoCAD DXF/DWG to Gerber. Here's examples showing how to generate Gerber files (from AutoCAD) with all Numerical products, https://www.numericalinnovations.com/pages/dxf-dwg-conversion-secrets-for-gerber-gds-ii-odb-etc
Still not sure what error I have. I've installed without issue. There's just nothing showing up like it should.