I've generally had good luck with Rails just working as expected on Windows, as long as you install the Ruby DevKit. JRuby works well too, as long as you're not

I've generally had good luck with Rails just working as expected on Windows, as long as you install the Ruby DevKit. JRuby works well too, as long as you're not using any gems with C extensions. As an alternative, I've run Rails apps using Docker, which also worked well. If you haven't tried Cmder as a shell, I'd recommend it. You can run cmd, Powershell, and bash tabs in the same window and if you get the full Cmder install it comes with most of the Unix command line utilities you're used to.