I ran into this glass door earlier this week while trying to get the vagrant-windows plugin working: $ vagrant plugin install vagrant-windows Installing the 'vagrant-windows' plugin. This can take a few minutes... /Applications/Vagrant/embedded/lib/ruby/2.0.0/rubygems/ext/builder.rb:62:in `run': ERROR: Failed to build gem native extension. (Gem::Installer::ExtensionBuildError) /Applications/Vagran
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