diff --git a/README.md b/README.md
index a79d4840..79f74ce7 100644
--- a/README.md
+++ b/README.md
@@ -29,6 +29,10 @@ consider the [vagrant-wrapper][vagrant_wrapper] gem which helps manage both
 styles of Vagrant installations
 ([background details][vagrant_wrapper_background]).
 
+If you are creating Windows VMs over a WinRM Transport, then the
+[vagrant-winrm][vagrant_winrm] Vagrant plugin must be installed. As a
+consequence, the minimum version of Vagrant required is 1.6 or higher.
+
 ### <a name="dependencies-virtualization"></a> Virtualbox and/or VMware Fusion/Workstation
 
 Currently this driver supports VirtualBox and VMware Fusion/Workstation.
@@ -442,6 +446,7 @@ Apache 2.0 (see [LICENSE][license])
 [vagrant_config_vmware]:    http://docs.vagrantup.com/v2/vmware/configuration.html
 [vagrant_providers]:        http://docs.vagrantup.com/v2/providers/index.html
 [vagrant_versioning]:       https://docs.vagrantup.com/v2/boxes/versioning.html
+[vagrant_winrm]:            https://github.com/criteo/vagrant-winrm
 [vagrant_wrapper]:          https://github.com/org-binbab/gem-vagrant-wrapper
 [vagrant_wrapper_background]: https://github.com/org-binbab/gem-vagrant-wrapper#background---aka-the-vagrant-gem-enigma
 [vmware_plugin]:            http://www.vagrantup.com/vmware
diff --git a/lib/kitchen/driver/vagrant.rb b/lib/kitchen/driver/vagrant.rb
index aa4fc727..6966930d 100644
--- a/lib/kitchen/driver/vagrant.rb
+++ b/lib/kitchen/driver/vagrant.rb
@@ -48,10 +48,6 @@ class Vagrant < Kitchen::Driver::Base
 
       default_config :network, []
 
-      default_config :password do |driver|
-        "vagrant" if driver.winrm_transport?
-      end
-
       default_config :pre_create_command, nil
 
       default_config :provision, false
@@ -64,10 +60,6 @@ class Vagrant < Kitchen::Driver::Base
 
       default_config :synced_folders, []
 
-      default_config :username do |driver|
-        "vagrant" if driver.winrm_transport?
-      end
-
       default_config :vagrantfile_erb,
         File.join(File.dirname(__FILE__), "../../../templates/Vagrantfile.erb")
       expand_path_for :vagrantfile_erb
@@ -176,6 +168,18 @@ def winrm_transport?
       WEBSITE = "http://www.vagrantup.com/downloads.html".freeze
       MIN_VER = "1.1.0".freeze
 
+      class << self
+
+        # @return [true,false] whether or not the vagrant-winrm plugin is
+        #   installed
+        # @api private
+        attr_accessor :winrm_plugin_passed
+
+        # @return [String] the version of Vagrant installed on the workstation
+        # @api private
+        attr_accessor :vagrant_version
+      end
+
       # Retuns a list of Vagrant base boxes produced by the Bento project
       # (https://github.com/chef/bento).
       #
@@ -254,6 +258,19 @@ def finalize_vm_hostname!
         end
       end
 
+      # Loads any required third party Ruby libraries or runs any shell out
+      # commands to prepare the plugin. This method will be called in the
+      # context of the main thread of execution and so does not necessarily
+      # have to be thread safe.
+      #
+      # @raise [ClientError] if any library loading fails or any of the
+      #   dependency requirements cannot be satisfied
+      # @api private
+      def load_needed_dependencies!
+        super
+        verify_winrm_plugin if winrm_transport?
+      end
+
       # Renders the Vagrantfile ERb template.
       #
       # @return [String] the contents for a Vagrantfile
@@ -332,19 +349,14 @@ def run_vagrant_up
       # @param state [Hash] mutable instance state
       # @api private
       def update_state(state)
-        hash = vagrant_ssh_config
+        hash = winrm_transport? ? vagrant_config(:winrm) : vagrant_config(:ssh)
 
         state[:hostname] = hash["HostName"]
-
-        if winrm_transport?
-          state[:username] = config[:username]
-          state[:password] = config[:password]
-        else
-          state[:username] = hash["User"]
-          state[:ssh_key] = hash["IdentityFile"]
-          state[:port] = hash["Port"]
-          state[:proxy_command] = hash["ProxyCommand"] if hash["ProxyCommand"]
-        end
+        state[:port] = hash["Port"]
+        state[:username] = hash["User"]
+        state[:password] = hash["Password"] if hash["Password"]
+        state[:ssh_key] = hash["IdentityFile"] if hash["IdentityFile"]
+        state[:proxy_command] = hash["ProxyCommand"] if hash["ProxyCommand"]
       end
 
       # @return [String] full local path to the directory containing the
@@ -357,11 +369,13 @@ def vagrant_root
         )
       end
 
+      # @param type [Symbol] either `:ssh` or `:winrm`
       # @return [Hash] key/value pairs resulting from parsing a
-      #   `vagrant ssh-config` local command invocation
+      #   `vagrant ssh-config` or `vagrant winrm-config` local command
+      #   invocation
       # @api private
-      def vagrant_ssh_config
-        lines = run_silently("vagrant ssh-config").split("\n").map do |line|
+      def vagrant_config(type)
+        lines = run_silently("vagrant #{type}-config").split("\n").map do |line|
           tokens = line.strip.partition(" ")
           [tokens.first, tokens.last.gsub(/"/, "")]
         end
@@ -372,12 +386,43 @@ def vagrant_ssh_config
       # @raise [UserError] if the `vagrant` command can not be found locally
       # @api private
       def vagrant_version
-        @version ||= run_silently("vagrant --version", :cwd => Dir.pwd).
-          chomp.split(" ").last
+        self.class.vagrant_version ||= run_silently(
+          "vagrant --version", :cwd => Dir.pwd).chomp.split(" ").last
       rescue Errno::ENOENT
         raise UserError, "Vagrant #{MIN_VER} or higher is not installed." \
           " Please download a package from #{WEBSITE}."
       end
+
+      # Verify that the vagrant-winrm plugin is installed and a suitable
+      #   version of Vagrant is installed
+      #
+      # @api private
+      def verify_winrm_plugin
+        if Gem::Version.new(vagrant_version) < Gem::Version.new("1.6")
+          raise UserError, "Detected an old version of Vagrant " \
+            "(#{vagrant_version}) that cannot support the vagrant-winrm " \
+            "Vagrant plugin." \
+            " Please upgrade to version 1.6 or higher from #{WEBSITE}."
+        end
+
+        if !winrm_plugin_installed?
+          raise UserError, "WinRM Transport requires the vagrant-winrm " \
+            "Vagrant plugin to properly communicate with this Vagrant VM. " \
+            "Please install this plugin with: " \
+            "`vagrant plugin install vagrant-winrm' and try again."
+        end
+      end
+
+      # @return [true,false] whether or not the vagrant-winrm plugin is
+      #   installed
+      # @api private
+      def winrm_plugin_installed?
+        return true if self.class.winrm_plugin_passed
+
+        self.class.winrm_plugin_passed = run_silently(
+          "vagrant plugin list", :cwd => Dir.pwd).
+          split("\n").find { |line| line =~ /^vagrant-winrm\s+/ }
+      end
     end
   end
 end
diff --git a/spec/kitchen/driver/vagrant_spec.rb b/spec/kitchen/driver/vagrant_spec.rb
index dd03c9fc..9f24bc13 100644
--- a/spec/kitchen/driver/vagrant_spec.rb
+++ b/spec/kitchen/driver/vagrant_spec.rb
@@ -63,6 +63,11 @@
 
   before { stub_const("ENV", env) }
 
+  after do
+    driver_object.class.send(:winrm_plugin_passed=, nil)
+    driver_object.class.send(:vagrant_version=, nil)
+  end
+
   describe "configuration" do
 
     context "for known bento platform names" do
@@ -328,32 +333,6 @@
         expect(driver[:vm_hostname]).to eq("this-is-a--k")
       end
     end
-
-    context "for non-WinRM-based transports" do
-
-      before { allow(transport).to receive(:name).and_return("Coolness") }
-
-      it "sets :username to nil by default" do
-        expect(driver[:username]).to eq(nil)
-      end
-
-      it "sets :password to nil by default" do
-        expect(driver[:password]).to eq(nil)
-      end
-    end
-
-    context "for WinRM-based transports" do
-
-      before { allow(transport).to receive(:name).and_return("WinRM") }
-
-      it "sets :username to vagrant by default" do
-        expect(driver[:username]).to eq("vagrant")
-      end
-
-      it "sets :password to vagrant by default" do
-        expect(driver[:password]).to eq("vagrant")
-      end
-    end
   end
 
   describe "#verify_dependencies" do
@@ -373,7 +352,7 @@
     end
 
     it "raises a UserError for a missing Vagrant command" do
-      allow(driver).to receive(:run_command).
+      allow(driver_object).to receive(:run_command).
         with("vagrant --version", any_args).and_raise(Errno::ENOENT)
 
       expect { driver.verify_dependencies }.to raise_error(
@@ -382,6 +361,69 @@
     end
   end
 
+  describe "#load_needed_dependencies!" do
+
+    describe "with winrm transport" do
+
+      before { allow(transport).to receive(:name).and_return("WinRM") }
+
+      it "old version of Vagrant raises UserError" do
+        with_vagrant("1.5.0")
+
+        expect { instance }.to raise_error(
+          Kitchen::Error, /Please upgrade to version 1.6 or higher/
+        )
+      end
+
+      it "modern vagrant without plugin installed raises UserError" do
+        with_modern_vagrant
+        allow(driver_object).to receive(:run_command).
+          with("vagrant plugin list", any_args).and_return("nope (1.2.3)")
+
+        expect { instance }.to raise_error(
+          Kitchen::Error, /vagrant plugin install vagrant-winrm/
+        )
+      end
+
+      it "modern vagrant with plugin installed succeeds" do
+        with_modern_vagrant
+        allow(driver_object).to receive(:run_command).
+          with("vagrant plugin list", any_args).
+          and_return("vagrant-winrm (1.2.3)")
+
+        instance
+      end
+    end
+
+    describe "without winrm transport" do
+
+      before { allow(transport).to receive(:name).and_return("Anything") }
+
+      it "old version of Vagrant succeeds" do
+        with_vagrant("1.5.0")
+
+        instance
+      end
+
+      it "modern vagrant without plugin installed succeeds" do
+        with_modern_vagrant
+        allow(driver_object).to receive(:run_command).
+          with("vagrant plugin list", any_args).and_return("nope (1.2.3)")
+
+        instance
+      end
+
+      it "modern vagrant with plugin installed succeeds" do
+        with_modern_vagrant
+        allow(driver_object).to receive(:run_command).
+          with("vagrant plugin list", any_args).
+          and_return("vagrant-winrm (1.2.3)")
+
+        instance
+      end
+    end
+  end
+
   describe "#create" do
 
     let(:cmd) { driver.create(state) }
@@ -480,35 +522,40 @@
 
     describe "for state" do
 
-      let(:output) do
-        <<-OUTPUT.gsub(/^ {10}/, "")
-          Host hehe
-            HostName 192.168.32.64
-            User vagrant
-            Port 2022
-            UserKnownHostsFile /dev/null
-            StrictHostKeyChecking no
-            PasswordAuthentication no
-            IdentityFile /path/to/private_key
-            IdentitiesOnly yes
-            LogLevel FATAL
-        OUTPUT
-      end
+      context "for non-WinRM-based transports" do
 
-      before do
-        allow(driver).to receive(:run_command).
-          with("vagrant ssh-config", any_args).and_return(output)
-      end
+        let(:output) do
+          <<-OUTPUT.gsub(/^ {10}/, "")
+            Host hehe
+              HostName 192.168.32.64
+              User vagrant
+              Port 2022
+              UserKnownHostsFile /dev/null
+              StrictHostKeyChecking no
+              PasswordAuthentication no
+              IdentityFile /path/to/private_key
+              IdentitiesOnly yes
+              LogLevel FATAL
+          OUTPUT
+        end
 
-      it "sets :hostname from ssh-config" do
-        cmd
+        before do
+          allow(transport).to receive(:name).and_return("Coolness")
+          allow(driver).to receive(:run_command).
+            with("vagrant ssh-config", any_args).and_return(output)
+        end
 
-        expect(state).to include(:hostname => "192.168.32.64")
-      end
+        it "sets :hostname from ssh-config" do
+          cmd
 
-      context "for non-WinRM-based transports" do
+          expect(state).to include(:hostname => "192.168.32.64")
+        end
+
+        it "sets :port from ssh-config" do
+          cmd
 
-        before { allow(transport).to receive(:name).and_return("Coolness") }
+          expect(state).to include(:port => "2022")
+        end
 
         it "sets :username from ssh-config" do
           cmd
@@ -516,16 +563,23 @@
           expect(state).to include(:username => "vagrant")
         end
 
-        it "sets :ssh_key from ssh-config" do
+        it "does not set :password by default" do
           cmd
 
-          expect(state).to include(:ssh_key => "/path/to/private_key")
+          expect(state.keys).to_not include(:password)
         end
 
-        it "sets :port from ssh-config" do
+        it "sets :password if Password is in ssh-config" do
+          output.concat("  Password yep\n")
           cmd
 
-          expect(state).to include(:port => "2022")
+          expect(state).to include(:password => "yep")
+        end
+
+        it "sets :ssh_key from ssh-config" do
+          cmd
+
+          expect(state).to include(:ssh_key => "/path/to/private_key")
         end
 
         it "does not set :proxy_command by default" do
@@ -544,20 +598,44 @@
 
       context "for WinRM-based transports" do
 
-        before { allow(transport).to receive(:name).and_return("WinRM") }
+        let(:output) do
+          <<-OUTPUT.gsub(/^ {10}/, "")
+            Host hehe
+              HostName 192.168.32.64
+              User vagrant
+              Password yep
+              Port 9999
+          OUTPUT
+        end
 
-        it "sets :username from config" do
-          config[:username] = "winuser"
+        before do
+          allow(transport).to receive(:name).and_return("WinRM")
+          allow(driver).to receive(:run_command).
+            with("vagrant winrm-config", any_args).and_return(output)
+        end
+
+        it "sets :hostname from winrm-config" do
           cmd
 
-          expect(state).to include(:username => "winuser")
+          expect(state).to include(:hostname => "192.168.32.64")
         end
 
-        it "sets :password from config" do
-          config[:password] = "mysecret"
+        it "sets :port from winrm-config" do
           cmd
 
-          expect(state).to include(:password => "mysecret")
+          expect(state).to include(:port => "9999")
+        end
+
+        it "sets :username from winrm-config" do
+          cmd
+
+          expect(state).to include(:username => "vagrant")
+        end
+
+        it "sets :password from winrm-config" do
+          cmd
+
+          expect(state).to include(:password => "yep")
         end
       end
     end
@@ -1226,13 +1304,16 @@ def debug_lines
   end
 
   def with_modern_vagrant
-    allow(driver).to receive(:run_command).
-      with("vagrant --version", any_args).and_return("Vagrant 1.7.2")
+    with_vagrant("1.7.2")
   end
 
   def with_unsupported_vagrant
-    allow(driver).to receive(:run_command).
-      with("vagrant --version", any_args).and_return("Vagrant 1.0.5")
+    with_vagrant("1.0.5")
+  end
+
+  def with_vagrant(version)
+    allow(driver_object).to receive(:run_command).
+      with("vagrant --version", any_args).and_return("Vagrant #{version}")
   end
 
   def regexify(str, line = :whole_line)