You can use the embedable release of python (which is signed) to run arbitrary unsigned code on windows. If you don't believe me, try it. Code signing on window

You can use the embedable release of python (which is signed) to run arbitrary unsigned code on windows. If you don't believe me, try it. Code signing on windows is a security theater at best and is next to useless. I agree that let's encrypt should just issue them. If Microsoft refuses to support it, someone should write a windows kernel module to add (or patch in) support.