As we saw above, there is quite a bit of ceremony involved in getting SSL just right and running WinRM over HTTPS. Lets be clear: its the right thing to do especially in production. However, you can avoid the ceremony but that just means there is other ceremonial sacrifices to be made. At this point, if you are connecting over HTTPS, authentication is pretty straight forward. If not, there are often additional steps to take. However these additional steps tend to be less friction laden, but more security heinous, than the SSL setup.