diff --git a/Rakefile b/Rakefile
index 0541e9fd..8fda9765 100644
--- a/Rakefile
+++ b/Rakefile
@@ -33,9 +33,10 @@ namespace :test do
     sh('sh', '-c', "cd #{path} && config=test-runner.yaml ruby -I ../../lib docker_test.rb tests/*")
   end
 
-  task :winrm do
-    path = File.join(File.dirname(__FILE__), 'test', 'winrm')
-    sh('sh', '-c', "cd #{path} && ruby windows.rb")
+  task :windows do
+    Dir.glob('test/windows/*_test.rb').all? do |file|
+      sh(Gem.ruby, '-w', '-Ilib:test', file)
+    end or fail 'Failures'
   end
 
   task :vm do
diff --git a/appveyor.yml b/appveyor.yml
index fde495f7..00c66d6d 100644
--- a/appveyor.yml
+++ b/appveyor.yml
@@ -42,4 +42,4 @@ build_script:
 
 test_script:
   - SET SPEC_OPTS=--format progress
-  - bundle exec rake test:winrm
+  - bundle exec rake test:windows
diff --git a/test/windows/local_test.rb b/test/windows/local_test.rb
new file mode 100644
index 00000000..b176da55
--- /dev/null
+++ b/test/windows/local_test.rb
@@ -0,0 +1,34 @@
+# encoding: utf-8
+# author: Christoph Hartmann
+# author: Dominik Richter
+
+require 'minitest/autorun'
+require 'minitest/spec'
+require 'mocha/setup'
+require 'train'
+
+describe 'windows local command' do
+  let(:conn) {
+    # get final config
+    target_config = Train.target_config({})
+    # initialize train
+    backend = Train.create('local', target_config)
+
+    # start or reuse a connection
+    conn = backend.connection
+    conn
+  }
+
+  it 'verify os' do
+    os = conn.os
+    os[:name].must_equal nil
+    os[:family].must_equal "windows"
+    os[:release].must_equal "Server 2012 R2"
+    os[:arch].must_equal nil
+  end
+
+  after do
+    # close the connection
+    conn.close
+  end
+end
diff --git a/test/windows/winrm_test.rb b/test/windows/winrm_test.rb
new file mode 100644
index 00000000..94084fe0
--- /dev/null
+++ b/test/windows/winrm_test.rb
@@ -0,0 +1,40 @@
+# encoding: utf-8
+# author: Christoph Hartmann
+# author: Dominik Richter
+
+require 'minitest/autorun'
+require 'minitest/spec'
+require 'mocha/setup'
+require 'train'
+
+describe 'windows local command' do
+  let(:conn) {
+    # get final config
+    target_config = Train.target_config({
+      target: ENV['train_target'],
+      password: ENV['winrm_pass'],
+      ssl: ENV['train_ssl'],
+      self_signed: true,
+    })
+
+    # initialize train
+    backend = Train.create('winrm', target_config)
+
+    # start or reuse a connection
+    conn = backend.connection
+    conn
+  }
+
+  it 'verify os' do
+    os = conn.os
+    os[:name].must_equal nil
+    os[:family].must_equal "windows"
+    os[:release].must_equal "Server 2012 R2"
+    os[:arch].must_equal nil
+  end
+
+  after do
+    # close the connection
+    conn.close
+  end
+end
diff --git a/test/winrm/windows.rb b/test/winrm/windows.rb
deleted file mode 100644
index 6e3555e7..00000000
--- a/test/winrm/windows.rb
+++ /dev/null
@@ -1,62 +0,0 @@
-#!/usr/bin/env ruby
-# encoding: utf-8
-#
-# Author:: Christoph Hartmann (<chris@lollyrock.com>)
-
-require 'train'
-require 'json'
-
-# expects the following env variables
-# export winrm_user=test_user
-# export winrm_pass=Pass@word1
-# export train_target='winrm://test_user@localhost:5985'
-# export train_ssl='true'
-
-def get_os(backend, opts = {})
-  # resolve configuration
-  target_config = Train.target_config(opts)
-  puts "Use the following config: #{target_config}"
-
-  # initialize train
-  train = Train.create(backend, target_config)
-
-  # start or reuse a connection
-  conn = train.connection
-  os = conn.os
-
-  # get OS info
-  conf = {
-    name:    os[:name],
-    family:  os[:family],
-    release: os[:release],
-    arch:    os[:arch],
-  }
-
-  # close the connection
-  conn.close
-  conf
-end
-
-def compare_hash(value, cmp)
-  value == cmp
-end
-
-# check local
-local = get_os('local')
-puts "Detected the following OS (local): #{local}"
-
-# winrm over http
-winrm = get_os('winrm', {
-  target: ENV['train_target'],
-  password: ENV['winrm_pass'],
-  ssl: ENV['train_ssl'],
-  self_signed: true,
-})
-puts "Detected the following OS (remote): #{winrm}"
-
-# compare values
-cmp = {:name=>nil, :family=>"windows", :release=>"Server 2012 R2", :arch=>nil}
-if !compare_hash(local, cmp) || !compare_hash(winrm, cmp)
-  puts "Expected OS: #{cmp}"
-  exit 1
-end