diff --git a/Gemfile b/Gemfile
index 4c721ffa..84394d93 100644
--- a/Gemfile
+++ b/Gemfile
@@ -17,11 +17,11 @@ gem 'slim', require: false
 gem 'liquid', require: false
 gem 'less', '~> 2.3.0', require: false
 gem 'stylus', require: false
+gem 'redcarpet', '~> 3.1', require: false
 gem 'asciidoctor', require: false
 
 platforms :ruby do
   gem 'therubyracer'
-  gem 'redcarpet', '~> 3.1'
   gem 'pry', require: false, group: :development
 end
 
diff --git a/gem_rake_helper.rb b/gem_rake_helper.rb
index 284cf5dc..5f95c90e 100644
--- a/gem_rake_helper.rb
+++ b/gem_rake_helper.rb
@@ -19,6 +19,7 @@ Cucumber::Rake::Task.new do |t|
   exempt_tags = ['--tags ~@wip']
   exempt_tags << '--tags ~@nojava' if RUBY_PLATFORM == 'java'
   exempt_tags << '--tags ~@encoding' unless Object.const_defined?(:Encoding)
+  exempt_tags << '--tags ~@nowindows' if Gem.win_platform?
   exempt_tags << '--tags ~@travishatesme' if ENV['TRAVIS'] == 'true'
   t.cucumber_opts = "--color #{exempt_tags.join(' ')} --strict --format #{ENV['CUCUMBER_FORMAT'] || 'Fivemat'}"
 end
@@ -27,6 +28,7 @@ Cucumber::Rake::Task.new(:cucumber_wip) do |t|
   exempt_tags = ['--tags @wip']
   exempt_tags << '--tags ~@nojava' if RUBY_PLATFORM == 'java'
   exempt_tags << '--tags ~@encoding' unless Object.const_defined?(:Encoding)
+  exempt_tags << '--tags ~@nowindows' if Gem.win_platform?
   t.cucumber_opts = "--color #{exempt_tags.join(' ')} --strict --format #{ENV['CUCUMBER_FORMAT'] || 'Fivemat'}"
 end
 
@@ -34,7 +36,7 @@ require 'rspec/core/rake_task'
 desc 'Run RSpec'
 RSpec::Core::RakeTask.new do |spec|
   spec.pattern = 'spec/**/*_spec.rb'
-  spec.rspec_opts = ['--color', '--format nested']
+  spec.rspec_opts = ['--color', '--format documentation']
 end
 
 desc 'Run tests, both RSpec and Cucumber'
diff --git a/middleman-core/features/gzip.feature b/middleman-core/features/gzip.feature
index 5a5a4265..93955a49 100644
--- a/middleman-core/features/gzip.feature
+++ b/middleman-core/features/gzip.feature
@@ -1,3 +1,4 @@
+@nowindows
 Feature: GZIP assets during build
 
   Scenario: Built assets should be gzipped
diff --git a/middleman-core/features/more-implied_extensions.feature b/middleman-core/features/more-implied_extensions.feature
index 31567443..10ee5b20 100644
--- a/middleman-core/features/more-implied_extensions.feature
+++ b/middleman-core/features/more-implied_extensions.feature
@@ -19,10 +19,7 @@ Feature: More default extensions
     When I go to "/stylesheets/style2.css"
     Then I should see "section"
     Then I should not see "I am in the layout"
-    When I go to "/stylesheets/style3.css"
-    Then I should see "color"
-    Then I should not see "I am in the layout"
-  
+
   Scenario: Default extensions build
     Given a fixture app "more-implied-extensions-app"
     And a successfully built app at "more-implied-extensions-app"
@@ -35,7 +32,6 @@ Feature: More default extensions
       | javascripts/app.js     |
       | stylesheets/style.css  |
       | stylesheets/style2.css |
-      | stylesheets/style3.css |
     And the file "test.html" should contain "Hello"
     And the file "test2.html" should contain "World"
     And the file "test3.html" should contain "Howdy"
@@ -46,5 +42,3 @@ Feature: More default extensions
     And the file "stylesheets/style.css" should not contain "I am in the layout"
     And the file "stylesheets/style2.css" should contain "section"
     And the file "stylesheets/style2.css" should not contain "I am in the layout"
-    And the file "stylesheets/style3.css" should contain "color"
-    And the file "stylesheets/style3.css" should not contain "I am in the layout"
\ No newline at end of file
diff --git a/middleman-core/features/twitter-bootstrap-compile.feature b/middleman-core/features/twitter-bootstrap-compile.feature
index 994cf11c..04ffc0ce 100644
--- a/middleman-core/features/twitter-bootstrap-compile.feature
+++ b/middleman-core/features/twitter-bootstrap-compile.feature
@@ -1,6 +1,6 @@
-@nojava
-Feature: Compile a complicated Twitter bootstrap app 
+@nojava @nowindows
+Feature: Compile a complicated Twitter bootstrap app
 
   Scenario: User drops Twitter Bootstrap source into an app
-  
-    Given a successfully built app at "twitter-bootstrap-app"
\ No newline at end of file
+
+    Given a successfully built app at "twitter-bootstrap-app"
diff --git a/middleman-core/fixtures/more-implied-extensions-app/source/stylesheets/style3.less b/middleman-core/fixtures/more-implied-extensions-app/source/stylesheets/style3.less
deleted file mode 100644
index 420d50d4..00000000
--- a/middleman-core/fixtures/more-implied-extensions-app/source/stylesheets/style3.less
+++ /dev/null
@@ -1,4 +0,0 @@
-@base: #f938ab;
-.box { 
-  color: @base;
-}
\ No newline at end of file
diff --git a/middleman-core/lib/middleman-core/step_definitions.rb b/middleman-core/lib/middleman-core/step_definitions.rb
index 4c14b091..95245f14 100644
--- a/middleman-core/lib/middleman-core/step_definitions.rb
+++ b/middleman-core/lib/middleman-core/step_definitions.rb
@@ -1,13 +1,21 @@
-MIDDLEMAN_ROOT_PATH = File.dirname(File.dirname(File.dirname(__FILE__)))
-MIDDLEMAN_BIN_PATH  = File.join(MIDDLEMAN_ROOT_PATH, 'bin')
-ENV['PATH'] = "#{MIDDLEMAN_BIN_PATH}#{File::PATH_SEPARATOR}#{ENV['PATH']}"
-
 require 'aruba/cucumber'
 require 'aruba/jruby'
 require 'middleman-core/step_definitions/middleman_steps'
 require 'middleman-core/step_definitions/builder_steps'
 require 'middleman-core/step_definitions/server_steps'
 
+# Monkeypatch for windows support
+module ArubaMonkeypatch
+  def detect_ruby(cmd)
+    if cmd.start_with?('middleman ') && Gem.win_platform?
+      "#{current_ruby} #{Dir.pwd}/bin/#{cmd}"
+    else
+      cmd.sub(/^ruby(?= )/, current_ruby)
+    end
+  end
+end
+World(ArubaMonkeypatch)
+
 Before do
   @aruba_timeout_seconds = RUBY_PLATFORM == 'java' ? 120 : 60
 end
diff --git a/middleman-core/spec/middleman-core/binary_spec.rb b/middleman-core/spec/middleman-core/binary_spec.rb
index 79944331..4f8d11d2 100644
--- a/middleman-core/spec/middleman-core/binary_spec.rb
+++ b/middleman-core/spec/middleman-core/binary_spec.rb
@@ -3,13 +3,13 @@ require 'middleman-core/util'
 describe "Middleman::Util#binary?" do
   %w(plain.txt unicode.txt unicode).each do |file|
     it "recognizes #{file} as not binary" do
-      expect(Middleman::Util.binary?(File.join(File.dirname(__FILE__), "binary_spec/#{file}"))).to be_false
+      expect(Middleman::Util.binary?(File.join(File.dirname(__FILE__), "binary_spec/#{file}"))).to be false
     end
   end
 
   %w(middleman.png middleman stars.svgz).each do |file|
     it "recognizes #{file} as binary" do
-      expect(Middleman::Util.binary?(File.join(File.dirname(__FILE__), "binary_spec/#{file}"))).to be_true
+      expect(Middleman::Util.binary?(File.join(File.dirname(__FILE__), "binary_spec/#{file}"))).to be true
     end
   end
 end