Plugin Installed, but not visible?

I’m having a tough time installing my first external plugin in kicad

I install it and it is listed in my external plugins menu.

If I restart kicad, and use it, it works.

Then if I close kicad and reopen it, the plugin icon is gone, and it is not listed in my external plugins menu anymore.

Does anyone know what might be happening?

I should have mentioned it is kicad 8 and freeroute plugin.

These statements contradict each other. Do you mean it only works once?
What is your OS?