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diff --git a/omnibus/files/rubygems-customization/windows/operating_system.rb b/omnibus/files/rubygems-customization/windows/operating_system.rb
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+++ b/omnibus/files/rubygems-customization/windows/operating_system.rb
@@ -0,0 +1,73 @@
+## Rubygems Customization ##
+# Customize rubygems install behavior and locations to keep user gems isolated
+# from the stuff we bundle with omnibus and any other ruby installations on the
+# system.
+
+# Always install and update new gems in "user install mode"
+Gem::ConfigFile::OPERATING_SYSTEM_DEFAULTS["install"] = "--user"
+Gem::ConfigFile::OPERATING_SYSTEM_DEFAULTS["update"] = "--user"
+
+# We will inject our hacks in if the user will allow it.
+begin
+  if (ENV['CHEFDK_ENV_FIX'] || '0').to_i != 0
+    require 'chefdk_env_customization'
+  end
+rescue
+  nil
+end
+
+module Gem
+
+  ##
+  # Override user_dir to live inside of ~/.chefdk
+
+  def self.user_dir
+    chefdk_home_set = !([nil, ''].include? ENV['CHEFDK_HOME'])
+    # We call expand_path here because it converts \ -> /
+    # Rubygems seems to require that we not use \
+    default_home = File.join(File.expand_path(ENV['LOCALAPPDATA']), 'chefdk')
+
+    chefdk_home = if chefdk_home_set
+      ENV['CHEFDK_HOME']
+    else
+      old_home = File.join(Gem.user_home, '.chefdk')
+      if File.exists?(old_home)
+        Gem.ui.alert_warning <<-EOF
+
+        ChefDK now defaults to using #{default_home} instead of #{old_home}.
+        Since #{old_home} exists on your machine, ChefDK will continue
+        to make use of it. Please set the environment variable CHEFDK_HOME
+        to #{old_home} to remove this warning. This warning will be removed
+        in the next major version bump of ChefDK.
+        EOF
+        old_home
+      else
+        default_home
+      end
+    end
+
+    # Prevents multiple warnings
+    ENV['CHEFDK_HOME'] = chefdk_home
+
+    parts = [chefdk_home, 'gem', ruby_engine]
+    parts << RbConfig::CONFIG['ruby_version'] unless RbConfig::CONFIG['ruby_version'].empty?
+    File.join parts
+  end
+
+end
+
+# :DK-BEG: override 'gem install' to enable RubyInstaller DevKit usage
+Gem.pre_install do |gem_installer|
+  unless gem_installer.spec.extensions.empty?
+    unless ENV['PATH'].include?('C:\\opscode\\chefdk\\embedded\\mingw\\bin') then
+      Gem.ui.say 'Temporarily enhancing PATH to include DevKit...' if Gem.configuration.verbose
+      ENV['PATH'] = 'C:\\opscode\\chefdk\\embedded\\bin;C:\\opscode\\chefdk\\embedded\\mingw\\bin;' + ENV['PATH']
+    end
+    ENV['RI_DEVKIT'] = 'C:\\opscode\\chefdk\\embedded'
+    ENV['CC'] = 'gcc'
+    ENV['CXX'] = 'g++'
+    ENV['CPP'] = 'cpp'
+  end
+end
+# :DK-END:
+