diff --git a/lib/chef/knife/bootstrap/windows-chef-client-msi.erb b/lib/chef/knife/bootstrap/windows-chef-client-msi.erb
index 224fd7c9..5bcf1ce8 100644
--- a/lib/chef/knife/bootstrap/windows-chef-client-msi.erb
+++ b/lib/chef/knife/bootstrap/windows-chef-client-msi.erb
@@ -188,11 +188,20 @@ goto install
 @endlocal
 
 @echo off
+
+<% if client_pem -%>
+> <%= bootstrap_directory %>\client.pem (
+ <%= escape_and_echo(::File.read(::File.expand_path(client_pem))) %>
+)
+<% end -%>
+
 echo Writing validation key...
 
+<% if validation_key -%>
 > <%= bootstrap_directory %>\validation.pem (
- <%= validation_key %>
+ <%= escape_and_echo(validation_key) %>
 )
+<% end -%>
 
 echo Validation key written.
 @echo on
diff --git a/lib/chef/knife/bootstrap_windows_base.rb b/lib/chef/knife/bootstrap_windows_base.rb
index 416beba9..215f20b8 100644
--- a/lib/chef/knife/bootstrap_windows_base.rb
+++ b/lib/chef/knife/bootstrap_windows_base.rb
@@ -190,12 +190,15 @@ def load_template(template=nil)
         IO.read(template).chomp
       end
 
+      def bootstrap_context
+        @bootstrap_context ||= Knife::Core::WindowsBootstrapContext.new(config, config[:run_list], Chef::Config)
+      end
+
       def render_template(template=nil)
         if config[:secret_file]
           config[:secret] = Chef::EncryptedDataBagItem.load_secret(config[:secret_file])
         end
-        context = Knife::Core::WindowsBootstrapContext.new(config, config[:run_list], Chef::Config)
-        Erubis::Eruby.new(template).evaluate(context)
+        Erubis::Eruby.new(template).evaluate(bootstrap_context)
       end
 
       def bootstrap(proto=nil)
@@ -207,13 +210,31 @@ def bootstrap(proto=nil)
 
         validate_name_args!
 
-
         @node_name = Array(@name_args).first
         # back compat--templates may use this setting:
         config[:server_name] = @node_name
 
         STDOUT.sync = STDERR.sync = true
 
+        if (Chef::Config[:validation_key] && !File.exist?(File.expand_path(Chef::Config[:validation_key])))
+          if Chef::VERSION.split('.').first.to_i == 11
+            ui.error("Unable to find validation key. Please verify your configuration file for validation_key config value.")
+            exit 1
+          end
+
+          unless locate_config_value(:chef_node_name)
+            ui.error("You must pass a node name with -N when bootstrapping with user credentials")
+            exit 1
+          end
+
+          client_builder.run
+          bootstrap_context.client_pem = client_builder.client_path
+        else
+          ui.info("Doing old-style registration with the validation key at #{Chef::Config[:validation_key]}...")
+          ui.info("Delete your validation key in order to use your user credentials instead")
+          ui.info("")
+        end
+
         wait_for_remote_response( config[:auth_timeout].to_i )
         ui.info("Bootstrapping Chef on #{ui.color(@node_name, :bold)}")
         # create a bootstrap.bat file on the node
@@ -231,6 +252,7 @@ def bootstrap(proto=nil)
         # execute the bootstrap.bat file
         bootstrap_command_result = run_command(bootstrap_command)
         ui.error("Bootstrap command returned #{bootstrap_command_result}") if bootstrap_command_result != 0
+
         bootstrap_command_result
       end
 
diff --git a/lib/chef/knife/bootstrap_windows_winrm.rb b/lib/chef/knife/bootstrap_windows_winrm.rb
index 333755e5..3227cb38 100644
--- a/lib/chef/knife/bootstrap_windows_winrm.rb
+++ b/lib/chef/knife/bootstrap_windows_winrm.rb
@@ -19,6 +19,8 @@
 require 'chef/knife/bootstrap_windows_base'
 require 'chef/knife/winrm'
 require 'chef/knife/winrm_base'
+require 'chef/knife/winrm_knife_base'
+
 
 class Chef
   class Knife
@@ -26,6 +28,7 @@ class BootstrapWindowsWinrm < Bootstrap
 
       include Chef::Knife::BootstrapWindowsBase
       include Chef::Knife::WinrmBase
+      include Chef::Knife::WinrmCommandSharedFunctions
 
       deps do
         require 'chef/knife/core/windows_bootstrap_context'
@@ -37,10 +40,15 @@ class BootstrapWindowsWinrm < Bootstrap
       banner "knife bootstrap windows winrm FQDN (options)"
 
       def run
+        if (Chef::Config[:validation_key] && !File.exist?(File.expand_path(Chef::Config[:validation_key])))
+          if !negotiate_auth? && !(locate_config_value(:winrm_transport) == 'ssl')
+            ui.error("Validatorless bootstrap over unsecure winrm channels could expose your key to network sniffing")
+            exit 1
+          end
+        end
         bootstrap
       end
 
-
       def run_command(command = '')
         winrm = Chef::Knife::Winrm.new
         winrm.name_args = [ server_name, command ]
@@ -99,4 +107,3 @@ def elapsed_time_in_minutes(start_time)
     end
   end
 end
-
diff --git a/lib/chef/knife/core/windows_bootstrap_context.rb b/lib/chef/knife/core/windows_bootstrap_context.rb
index 5819dd9b..9d0c52f3 100644
--- a/lib/chef/knife/core/windows_bootstrap_context.rb
+++ b/lib/chef/knife/core/windows_bootstrap_context.rb
@@ -22,6 +22,7 @@
 require 'knife-windows/path_helper'
 # require 'chef/util/path_helper'
 
+
 class Chef
   class Knife
     module Core
@@ -34,10 +35,13 @@ module Core
       class WindowsBootstrapContext < BootstrapContext
         PathHelper = ::Knife::Windows::PathHelper
 
+        attr_accessor :client_pem
+
         def initialize(config, run_list, chef_config, secret=nil)
           @config       = config
           @run_list     = run_list
           @chef_config  = chef_config
+          @secret       = secret
           # Compatibility with Chef 12 and Chef 11 versions
           begin
             # Pass along the secret parameter for Chef 12
@@ -49,7 +53,11 @@ def initialize(config, run_list, chef_config, secret=nil)
         end
 
         def validation_key
-          escape_and_echo(super)
+          if File.exist?(File.expand_path(@chef_config[:validation_key]))
+            IO.read(File.expand_path(@chef_config[:validation_key]))
+          else
+            false
+          end
         end
 
         def secret
@@ -67,8 +75,6 @@ def config_content
 
 chef_server_url  "#{@chef_config[:chef_server_url]}"
 validation_client_name "#{@chef_config[:validation_client_name]}"
-client_key        "c:/chef/client.pem"
-validation_key    "c:/chef/validation.pem"
 
 file_cache_path   "c:/chef/cache"
 file_backup_path  "c:/chef/backup"
diff --git a/spec/functional/bootstrap_download_spec.rb b/spec/functional/bootstrap_download_spec.rb
index 51a72b4b..e56c9094 100644
--- a/spec/functional/bootstrap_download_spec.rb
+++ b/spec/functional/bootstrap_download_spec.rb
@@ -86,11 +86,13 @@
       allow(Chef::Knife::Winrm).to receive(:new).and_return(mock_winrm)
 
       allow(Chef::Knife::Core::WindowsBootstrapContext).to receive(:new).and_return(mock_bootstrap_context)
+      Chef::Config[:knife] = {:winrm_transport => 'plaintext', :chef_node_name => 'foo.example.com', :winrm_authentication_protocol => 'negotiate'}
     end
 
     it "downloads the chef-client MSI from the default location during winrm bootstrap" do
       run_download_scenario
     end
+
     context "when provided a custom msi_url to fetch from" do
       let(:mock_bootstrap_context) { Chef::Knife::Core::WindowsBootstrapContext.new(
         { :msi_url => "file:///C:/Windows/System32/xcopy.exe" }, nil, { :knife => {} }) }
@@ -115,6 +117,13 @@ def run_download_scenario
     clean_test_case
 
     winrm_bootstrapper = Chef::Knife::BootstrapWindowsWinrm.new([ "127.0.0.1" ])
+
+    if chef_12?
+      winrm_bootstrapper.client_builder = instance_double("Chef::Knife::Bootstrap::ClientBuilder", :run => nil, :client_path => nil)
+    elsif chef_11?
+      allow(File).to receive(:exist?).with(File.expand_path(Chef::Config[:validation_key])).and_return(true)
+    end
+
     allow(winrm_bootstrapper).to receive(:wait_for_remote_response)
     winrm_bootstrapper.config[:template_file] = @template_file_path
 
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 08e9988c..0230ba3d 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -54,9 +54,18 @@ def windows2012?
   is_win2k12
 end
 
+def chef_11?
+  Chef::VERSION.split('.').first.to_i == 11
+end
+
+def chef_12?
+  Chef::VERSION.split('.').first.to_i == 12
+end
 
 RSpec.configure do |config|
   config.filter_run_excluding :windows_only => true unless windows?
   config.filter_run_excluding :windows_2012_only => true unless windows2012?
+  config.filter_run_excluding :chef_11_only unless chef_11?
+  config.filter_run_excluding :chef_12_only unless chef_12?
 end
 
diff --git a/spec/unit/knife/bootstrap_template_spec.rb b/spec/unit/knife/bootstrap_template_spec.rb
index 9af918fa..fc586e19 100644
--- a/spec/unit/knife/bootstrap_template_spec.rb
+++ b/spec/unit/knife/bootstrap_template_spec.rb
@@ -28,10 +28,9 @@
     knife.parse_options(options)
     # Avoid referencing a validation keyfile we won't find during #render_template
     template = IO.read(template_file).chomp
-    template_string = template.gsub(/^.*[Vv]alidation_key.*$/, '')
-    knife.render_template(template_string)
+    knife.render_template(template)
   end
-  
+
   before(:all) do
     @original_config = Chef::Config.hash_dup
     @original_knife_config = Chef::Config[:knife].dup
@@ -78,7 +77,7 @@
     subject(:knife) { described_class.new }
 
     context "with explicitly provided msi_url" do
-      let(:options) { ["--msi_url", "file:///something.msi"] } 
+      let(:options) { ["--msi_url", "file:///something.msi"] }
 
       it "bootstrap batch file must fetch from provided url" do
         expect(rendered_template).to match(%r{.*REMOTE_SOURCE_MSI_URL=file:///something\.msi.*})
diff --git a/spec/unit/knife/bootstrap_windows_winrm_spec.rb b/spec/unit/knife/bootstrap_windows_winrm_spec.rb
index 6b46ddcb..3e42470e 100644
--- a/spec/unit/knife/bootstrap_windows_winrm_spec.rb
+++ b/spec/unit/knife/bootstrap_windows_winrm_spec.rb
@@ -28,6 +28,7 @@
   before do
     #    Kernel.stub(:sleep).and_return 10
     allow(bootstrap).to receive(:sleep).and_return(10)
+    allow(File).to receive(:exist?).with(File.expand_path(Chef::Config[:validation_key])).and_return(true)
   end
 
   after do
@@ -39,6 +40,7 @@
   let(:session) { Chef::Knife::Winrm::WinrmSession.new({ :host => 'winrm.cloudapp.net', :port => '5986', :transport => :ssl }) }
 
   let(:initial_fail_count) { 4 }
+
   it 'should retry if a 401 is received from WinRM' do
     call_result_sequence = Array.new(initial_fail_count) {lambda {raise WinRM::WinRMHTTPTransportError.new('', '401')}}
     call_result_sequence.push(0)
@@ -61,16 +63,6 @@
     bootstrap.send(:wait_for_remote_response, 2)
   end
 
-  it 'should have a wait timeout of 2 minutes by default' do
-    allow(bootstrap).to receive(:run_command).and_raise(WinRM::WinRMHTTPTransportError.new('','500'))
-    allow(bootstrap).to receive(:create_bootstrap_bat_command).and_raise(SystemExit)
-    expect(bootstrap).to receive(:wait_for_remote_response).with(2)
-    allow(bootstrap).to receive(:validate_name_args!).and_return(nil)
-    allow(bootstrap.ui).to receive(:info)
-    bootstrap.config[:auth_timeout] = bootstrap.options[:auth_timeout][:default]
-    expect { bootstrap.bootstrap }.to raise_error(SystemExit)
-  end
-
   it 'should keep retrying at 10s intervals if the timeout in minutes has not elapsed' do
     call_result_sequence = Array.new(initial_fail_count) {lambda {raise WinRM::WinRMHTTPTransportError.new('', '500')}}
     call_result_sequence.push(0)
@@ -82,12 +74,22 @@
     bootstrap.send(:wait_for_remote_response, 2)
   end
 
+  it 'should have a wait timeout of 2 minutes by default' do
+    allow(bootstrap).to receive(:run_command).and_raise(WinRM::WinRMHTTPTransportError.new('','500'))
+    allow(bootstrap).to receive(:create_bootstrap_bat_command).and_raise(SystemExit)
+    expect(bootstrap).to receive(:wait_for_remote_response).with(2)
+    allow(bootstrap).to receive(:validate_name_args!).and_return(nil)
+    allow(bootstrap.ui).to receive(:info)
+    bootstrap.config[:auth_timeout] = bootstrap.options[:auth_timeout][:default]
+    expect { bootstrap.bootstrap }.to raise_error(SystemExit)
+  end
+
   it "should exit bootstrap with non-zero status if the bootstrap fails" do
     command_status = 1
 
     #Stub out calls to create the session and just get the exit codes back
     winrm_mock = Chef::Knife::Winrm.new
-    allow(Chef::Knife::Winrm).to receive(:new).and_return(winrm_mock)    
+    allow(Chef::Knife::Winrm).to receive(:new).and_return(winrm_mock)
     allow(winrm_mock).to receive(:run).and_raise(SystemExit.new(command_status))
     #Skip over templating stuff and checking with the remote end
     allow(bootstrap).to receive(:create_bootstrap_bat_command)
@@ -97,7 +99,6 @@
     expect { bootstrap.run_with_pretty_exceptions }.to raise_error(SystemExit) { |e| expect(e.status).to eq(command_status) }
   end
 
-
   it 'should stop retrying if more than 2 minutes has elapsed' do
     times = [ Time.new(2014, 4, 1, 22, 25), Time.new(2014, 4, 1, 22, 51), Time.new(2014, 4, 1, 22, 28) ]
     allow(Time).to receive(:now).and_return(*times)
@@ -111,4 +112,39 @@
     bootstrap.config[:auth_timeout] = bootstrap.options[:auth_timeout][:default]
     expect { bootstrap.bootstrap }.to raise_error RuntimeError
   end
-end
\ No newline at end of file
+
+  context "when validation_key is not present" do
+    context "using chef 11", :chef_11_only do
+      before do
+        allow(File).to receive(:exist?).with(File.expand_path(Chef::Config[:validation_key])).and_return(false)
+      end
+
+      it 'raises an exception if validation_key is not present in chef 11' do
+        expect(bootstrap.ui).to receive(:error)
+        expect { bootstrap.bootstrap }.to raise_error(SystemExit)
+      end
+    end
+
+    context "using chef 12", :chef_12_only do
+      before do
+        allow(File).to receive(:exist?).with(File.expand_path(Chef::Config[:validation_key])).and_return(false)
+        bootstrap.client_builder = instance_double("Chef::Knife::Bootstrap::ClientBuilder", :run => nil, :client_path => nil)
+        Chef::Config[:knife] = {:chef_node_name => 'foo.example.com'}
+      end
+
+      it 'raises an exception if winrm_authentication_protocol is basic and transport is plaintext' do
+        Chef::Config[:knife] = {:winrm_authentication_protocol => 'basic', :winrm_transport => 'plaintext', :chef_node_name => 'foo.example.com'}
+        expect(bootstrap.ui).to receive(:error)
+        expect { bootstrap.run }.to raise_error(SystemExit)
+      end
+
+      it 'raises an exception if chef_node_name is not present ' do
+        Chef::Config[:knife] = {:chef_node_name => nil}
+        expect(bootstrap.client_builder).not_to receive(:run)
+        expect(bootstrap.client_builder).not_to receive(:client_path)
+        expect(bootstrap.ui).to receive(:error)
+        expect { bootstrap.bootstrap }.to raise_error(SystemExit)
+      end
+    end
+  end
+end