Ruby on Rails on Azure App Service (Web Sites) with Linux (and Ubuntu on Windows 10)

Running Ruby on Rails on Windows has historically sucked. Most of the Ruby/Rails folks are Mac and Linux users and haven't focused on getting Rails to be usable for daily development on Windows. There have been some heroic efforts by a number of volunteers to get Rails working with projects like RailsInstaller, but native modules and dependencies almost always cause problems. Even more, when you go to deploy your Rails app you're likely using a Linux host so you may run into differences between operating systems.