diff --git a/Gemfile b/Gemfile
index 84394d93..230b683f 100644
--- a/Gemfile
+++ b/Gemfile
@@ -1,39 +1,37 @@
 source 'https://rubygems.org'
 
 # Build and doc tools
-gem 'rake',     '~> 10.0.3', require: false
-gem 'yard',     '~> 0.8.0', require: false
+gem 'rake', '~> 10.3', require: false
+gem 'yard', '~> 0.8', require: false
 
 # Test tools
-gem 'cucumber', '~> 1.3.1'
-gem 'fivemat',  '~> 1.2.1'
-gem 'aruba',    '~> 0.5.1'
-gem 'rspec',    '~> 2.12'
-gem 'simplecov'
+gem 'pry', '~> 0.10', group: :development
+gem 'aruba', '~> 0.6'
+gem 'rspec', '~> 3.0'
+gem 'fivemat', '~> 1.3'
+gem 'cucumber', '~> 1.3'
 
 # Optional middleman dependencies, included for tests
-gem 'sinatra', require: false
-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
+gem 'less', '2.3.0', require: false
+gem 'slim', '~> 2.0', require: false
+gem 'liquid', '~> 2.6', require: false
+gem 'stylus', '~> 1.0', require: false
+gem 'sinatra','~> 1.4', require: false
+gem 'asciidoctor', '~> 0.1', require: false
 
-platforms :ruby do
-  gem 'therubyracer'
-  gem 'pry', require: false, group: :development
-end
+# For less, since it doesn't use ExecJS (which also means less wont work on windows)
+gem 'therubyracer', platforms: :ruby
+gem 'therubyrhino', platforms: :jruby
 
-platforms :jruby do
-  gem 'therubyrhino'
-end
+# Redcarpet doesn't work on JRuby
+gem 'redcarpet', '~> 3.1', require: false unless RUBY_ENGINE == 'jruby'
 
 # Code Quality
-gem 'coveralls', require: false
-gem 'rubocop', require: false
+gem 'rubocop', '~> 0.24', require: false
+gem 'simplecov', '0.7.1', require: false
+gem 'coveralls', '~> 0.7', require: false
 
 # Middleman itself
+gem 'middleman', path: 'middleman'
 gem 'middleman-core', path: 'middleman-core'
 gem 'middleman-sprockets', github: 'middleman/middleman-sprockets'
-gem 'middleman', path: 'middleman'
diff --git a/middleman-core/lib/middleman-core/step_definitions/server_steps.rb b/middleman-core/lib/middleman-core/step_definitions/server_steps.rb
index 0dda0772..30098760 100644
--- a/middleman-core/lib/middleman-core/step_definitions/server_steps.rb
+++ b/middleman-core/lib/middleman-core/step_definitions/server_steps.rb
@@ -68,29 +68,29 @@ When /^I go to "([^\"]*)"$/ do |url|
 end
 
 Then /^going to "([^\"]*)" should not raise an exception$/ do |url|
-  lambda { @browser.get(URI.escape(url)) }.should_not raise_exception
+  expect(lambda { @browser.get(URI.escape(url)) }).to_not raise_exception
 end
 
 Then /^the content type should be "([^\"]*)"$/ do |expected|
-  @browser.last_response.content_type.should start_with(expected)
+  expect(@browser.last_response.content_type).to start_with(expected)
 end
 
 Then /^I should see "([^\"]*)"$/ do |expected|
-  @browser.last_response.body.should include(expected)
+  expect(@browser.last_response.body).to include(expected)
 end
 
 Then /^I should see '([^\']*)'$/ do |expected|
-  @browser.last_response.body.should include(expected)
+  expect(@browser.last_response.body).to include(expected)
 end
 
 Then /^I should see:$/ do |expected|
-  @browser.last_response.body.should include(expected)
+  expect(@browser.last_response.body).to include(expected)
 end
 
 Then /^I should not see "([^\"]*)"$/ do |expected|
-  @browser.last_response.body.should_not include(expected)
+  expect(@browser.last_response.body).to_not include(expected)
 end
 
 Then /^I should see "([^\"]*)" lines$/ do |lines|
-  @browser.last_response.body.chomp.split($/).length.should == lines.to_i
+  expect(@browser.last_response.body.chomp.split($/).length).to eq(lines.to_i)
 end