diff --git a/lib/chef/knife/bootstrap_windows_base.rb b/lib/chef/knife/bootstrap_windows_base.rb
index c793f335..215f20b8 100644
--- a/lib/chef/knife/bootstrap_windows_base.rb
+++ b/lib/chef/knife/bootstrap_windows_base.rb
@@ -217,9 +217,6 @@ def bootstrap(proto=nil)
         STDOUT.sync = STDERR.sync = true
 
         if (Chef::Config[:validation_key] && !File.exist?(File.expand_path(Chef::Config[:validation_key])))
-          # require 'pry'
-          # binding.pry
-
           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
diff --git a/lib/chef/knife/bootstrap_windows_winrm.rb b/lib/chef/knife/bootstrap_windows_winrm.rb
index 44418178..3227cb38 100644
--- a/lib/chef/knife/bootstrap_windows_winrm.rb
+++ b/lib/chef/knife/bootstrap_windows_winrm.rb
@@ -30,7 +30,6 @@ class BootstrapWindowsWinrm < Bootstrap
       include Chef::Knife::WinrmBase
       include Chef::Knife::WinrmCommandSharedFunctions
 
-
       deps do
         require 'chef/knife/core/windows_bootstrap_context'
         require 'chef/json_compat'
@@ -42,20 +41,14 @@ class BootstrapWindowsWinrm < Bootstrap
 
       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 only supported with negotiate authentication protocol and ssl/plaintext transport")
-            exit 1
-          elsif !(Chef::Platform.windows?) && negotiate_auth?
-            ui.error("Negotiate protocol with plaintext transport is only supported when this tool is invoked from windows based system")
+            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 ]
diff --git a/spec/functional/bootstrap_download_spec.rb b/spec/functional/bootstrap_download_spec.rb
index 3cade82e..e56c9094 100644
--- a/spec/functional/bootstrap_download_spec.rb
+++ b/spec/functional/bootstrap_download_spec.rb
@@ -100,7 +100,6 @@
         run_download_scenario
       end
     end
-
   end
 
   def download_succeeded?
@@ -118,13 +117,10 @@ 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)
-      allow(winrm_bootstrapper.client_builder).to receive(:run)
-      allow(winrm_bootstrapper.client_builder).to receive(:client_path)
-    end
-
-    if chef_11?
+    elsif chef_11?
       allow(File).to receive(:exist?).with(File.expand_path(Chef::Config[:validation_key])).and_return(true)
     end
 
diff --git a/spec/spec_helper.rb b/spec/spec_helper.rb
index 773b4234..0230ba3d 100644
--- a/spec/spec_helper.rb
+++ b/spec/spec_helper.rb
@@ -65,5 +65,7 @@ def chef_12?
 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_windows_winrm_spec.rb b/spec/unit/knife/bootstrap_windows_winrm_spec.rb
index 73c9c777..3e42470e 100644
--- a/spec/unit/knife/bootstrap_windows_winrm_spec.rb
+++ b/spec/unit/knife/bootstrap_windows_winrm_spec.rb
@@ -41,7 +41,7 @@
 
   let(:initial_fail_count) { 4 }
 
-   it 'should retry if a 401 is received from WinRM' do
+  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)
     allow(bootstrap).to receive(:run_command).and_return(*call_result_sequence)
@@ -114,7 +114,18 @@
   end
 
   context "when validation_key is not present" do
-    if chef_12?
+    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)
@@ -135,16 +146,5 @@
         expect { bootstrap.bootstrap }.to raise_error(SystemExit)
       end
     end
-
-    if chef_11?
-      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
   end
-end
\ No newline at end of file
+end