I've been doing Ruby on Rails since the early 2.x days. (I dabbled with 1.x, but gave up to let it "age" a little.) For the first 5 years, I was on Linux full t

I've been doing Ruby on Rails since the early 2.x days. (I dabbled with 1.x, but gave up to let it "age" a little.) For the first 5 years, I was on Linux full time, and it was great. Then I moved to Mac, and it was almost as great. (The terminal situation and general integration of the command line is still more cohesive in Linux.) For about the past 10 years, I've been at a standard Fortune 250 Windows-is-the-entire-world kind of place. I've been able to do my work on my personal Mac, but I've always made sure that I can do all of my Rails work on my corporate Windows laptop. There are times my code needs to access file locations and other applications inside the corporate firewall. Obviously, people are correct that Ruby is not a "first-class" citizen on Windows, but RubyInstaller (https://rubyinstaller.org https://rubyinstaller.org) has been a lifesaver. Not only does it "just work," and compile all the gems I've used, but it also includes a neat little script that addresses the common "corporate" practice of having to install custom SSL certificates so that IT can decode all traffic going through their firewall. (They install these certs directly into the Windows networking stack, but bundler doesn't use the stack.) The SSL bundle their script creates is also useful for use with Postgres database connections. You just need RubyInstaller, NodeJS, and a better terminal application (or maybe RubyMine), and you're GTG on Windows. I've tried to use WSL, both version 1 and 2. If you need to support many Rails apps, and switch Ruby versions (with RVM or rbenv), that might be the way to go, but for just one (big) project, I prefer to stay inside the native environment. And even if I were tempted to use WSL, I'd rather just use an actual VM software like VMWare or OpenBox, and control the details of the virtualization myself. YMMV.