diff --git a/plugins/communicators/winrm/command_filter.rb b/plugins/communicators/winrm/command_filter.rb
new file mode 100644
index 000000000..4b5e2ab5c
--- /dev/null
+++ b/plugins/communicators/winrm/command_filter.rb
@@ -0,0 +1,48 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+   
+    # Handles loading and applying all available WinRM command filters
+    class CommandFilter
+
+      @@cmd_filters = [
+        "cat",
+        "chmod",
+        "chown",
+        "grep",
+        "rm",
+        "test",
+        "uname",
+        "which"
+      ]
+
+      # Filter the given Vagrant command to ensure compatibility with Windows
+      #
+      # @param [String] The Vagrant shell command
+      # @returns [String] Windows runnable command or empty string
+      def filter(command)
+        command_filters.each { |c| command = c.filter(command) if c.accept?(command) }
+        command
+      end
+
+      # All the available Linux command filters
+      #
+      # @returns [Array] All Linux command filter instances
+      def command_filters
+        @command_filters ||= create_command_filters()
+      end
+
+      private
+
+      def create_command_filters
+        [].tap do |filters|
+          @@cmd_filters.each do |cmd|
+            require_relative "command_filters/#{cmd}"
+            class_name = "VagrantPlugins::CommunicatorWinRM::CommandFilters::#{cmd.capitalize}"
+            filters << Module.const_get(class_name).new
+          end
+        end
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/cat.rb b/plugins/communicators/winrm/command_filters/cat.rb
new file mode 100644
index 000000000..5d9cf8e01
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/cat.rb
@@ -0,0 +1,27 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Handles the special case of determining the guest OS using cat
+      class Cat
+
+        def filter(command)
+          # cat /etc/release | grep -i OmniOS
+          # cat /etc/redhat-release
+          # cat /etc/issue | grep 'Core Linux'
+          # cat /etc/release | grep -i SmartOS
+          ''
+        end
+
+        def accept?(command)
+          # cat works in PowerShell, however we don't want to run Guest
+          # OS detection as this will fail on Windows because the lack of the
+          # grep command
+          command.start_with?('cat /etc/')
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/chmod.rb b/plugins/communicators/winrm/command_filters/chmod.rb
new file mode 100644
index 000000000..a336f5dd4
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/chmod.rb
@@ -0,0 +1,21 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'chmod' command to a PowerShell equivalent
+      class Chmod
+
+        def filter(command)
+          # Not support on Windows, the communicator will skip this command
+          ''
+        end
+
+        def accept?(command)
+          command.start_with?('chmod ')
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/chown.rb b/plugins/communicators/winrm/command_filters/chown.rb
new file mode 100644
index 000000000..127731ff6
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/chown.rb
@@ -0,0 +1,21 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'chown' command to a PowerShell equivalent
+      class Chown
+
+        def filter(command)
+          # Not support on Windows, the communicator will skip this command
+          ''
+        end
+
+        def accept?(command)
+          command.start_with?('chown ')
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/grep.rb b/plugins/communicators/winrm/command_filters/grep.rb
new file mode 100644
index 000000000..96ce32ca6
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/grep.rb
@@ -0,0 +1,26 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'grep' command to a PowerShell equivalent
+      class Grep
+
+        def filter(command)
+          # grep 'Fedora release [12][67890]' /etc/redhat-release
+          # grep Funtoo /etc/gentoo-release
+          # grep Gentoo /etc/gentoo-release
+
+          # grep is often used to detect the guest type in Vagrant, so don't bother running
+          # to speed up OS detection
+          ''
+        end
+
+        def accept?(command)
+          command.start_with?('grep ')
+        end
+
+      end
+
+    end
+  end
+end
\ No newline at end of file
diff --git a/plugins/communicators/winrm/command_filters/rm.rb b/plugins/communicators/winrm/command_filters/rm.rb
new file mode 100644
index 000000000..a0078c83d
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/rm.rb
@@ -0,0 +1,28 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'rm' command to a PowerShell equivalent
+      class Rm
+
+        def filter(command)
+          # rm -Rf /some/dir
+          # rm /some/dir
+          cmd_parts = command.strip.split(/\s+/)
+          dir = cmd_parts[1]
+          if dir == '-Rf'
+            dir = cmd_parts[2]
+            return "rm '#{dir}' -recurse -force"
+          end
+          return "rm '#{dir}' -force"
+        end
+
+        def accept?(command)
+          command.start_with?('rm ')
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/test.rb b/plugins/communicators/winrm/command_filters/test.rb
new file mode 100644
index 000000000..23fddc8bf
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/test.rb
@@ -0,0 +1,68 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'test' command to a PowerShell equivalent
+      class Test
+
+        def filter(command)
+          # test -d /tmp/dir
+          # test -f /tmp/afile
+          # test -L /somelink
+          # test -x /tmp/some.exe
+          
+          cmd_parts = command.strip.split(/\s+/)
+          flag = cmd_parts[1]
+          path = cmd_parts[2]
+
+          if flag == '-d'
+            check_for_directory(path)
+          elsif flag == '-f' || flag == '-x'
+            check_for_file(path)
+          else
+            check_exists(path)
+          end
+        end
+
+        def accept?(command)
+          command.start_with?("test ")
+        end
+
+
+        private
+
+        def check_for_directory(path)
+          <<-EOH
+            $p = "#{path}"
+            if ((Test-Path $p) -and (get-item $p).PSIsContainer) {
+              exit 0
+            }
+            exit 1
+          EOH
+        end
+
+        def check_for_file(path)
+          <<-EOH
+            $p = "#{path}"
+            if ((Test-Path $p) -and (!(get-item $p).PSIsContainer)) {
+              exit 0
+            }
+            exit 1
+          EOH
+        end
+
+        def check_exists(path)
+          <<-EOH
+            $p = "#{path}"
+            if (Test-Path $p) {
+              exit 0
+            }
+            exit 1
+          EOH
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/uname.rb b/plugins/communicators/winrm/command_filters/uname.rb
new file mode 100644
index 000000000..4a8b0836d
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/uname.rb
@@ -0,0 +1,31 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'uname' command to a PowerShell equivalent
+      class Uname
+
+        def filter(command)
+          # uname -s | grep 'Darwin'
+          # uname -s | grep VMkernel
+          # uname -s | grep 'FreeBSD'
+          # uname -s | grep 'Linux'
+          # uname -s | grep NetBSD
+          # uname -s | grep 'OpenBSD'
+          # uname -sr | grep SunOS | grep -v 5.11
+          # uname -sr | grep 'SunOS 5.11'
+
+          # uname is used to detect the guest type in Vagrant, so don't bother running
+          # to speed up OS detection
+          ''
+        end
+
+        def accept?(command)
+          command.start_with?('uname ')
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/which.rb b/plugins/communicators/winrm/command_filters/which.rb
new file mode 100644
index 000000000..cf046ca19
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/which.rb
@@ -0,0 +1,26 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+
+      # Converts a *nix 'which' command to a PowerShell equivalent
+      class Which
+
+        def filter(command)
+          executable = command.strip.split(/\s+/)[1]
+          return <<-EOH
+            $command = [Array](Get-Command #{executable} -errorAction SilentlyContinue)
+            if ($null -eq $command) { exit 1 }
+            write-host $command[0].Definition
+            exit 0
+          EOH
+        end
+
+        def accept?(command)
+          command.start_with?('which ')
+        end
+
+      end
+
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/communicator.rb b/plugins/communicators/winrm/communicator.rb
index 850b0eba7..fe1d66f92 100644
--- a/plugins/communicators/winrm/communicator.rb
+++ b/plugins/communicators/winrm/communicator.rb
@@ -4,6 +4,7 @@ require "log4r"
 
 require_relative "helper"
 require_relative "shell"
+require_relative "command_filter"
 
 module VagrantPlugins
   module CommunicatorWinRM
@@ -16,9 +17,10 @@ module VagrantPlugins
       end
 
       def initialize(machine)
-        @machine = machine
-        @logger  = Log4r::Logger.new("vagrant::communication::winrm")
-        @shell   = nil
+        @machine    = machine
+        @shell      = nil
+        @logger     = Log4r::Logger.new("vagrant::communication::winrm")
+        @cmd_filter = CommandFilter.new()
 
         @logger.info("Initializing WinRMCommunicator")
       end
@@ -50,6 +52,10 @@ module VagrantPlugins
       end
 
       def execute(command, opts={}, &block)
+        # If this is a *nix command with no Windows equivilant, don't run it
+        command = @cmd_filter.filter(command)
+        return 0 if command.empty?
+
         opts = {
           :error_check => true,
           :error_class => Errors::ExecutionError,
@@ -58,26 +64,15 @@ module VagrantPlugins
           :shell       => :powershell
         }.merge(opts || {})
 
-        if opts[:shell] == :powershell
-          script  = File.expand_path("../scripts/command_alias.ps1", __FILE__)
-          script  = File.read(script)
-          command = script << "\r\n" << command << "\r\nexit $LASTEXITCODE"
-        end
-
         output = shell.send(opts[:shell], command, &block)
-
-        return output if opts[:shell] == :wql
-        exitcode = output[:exitcode]
-        raise_execution_error(opts, exitcode) if opts[:error_check] && exitcode != 0
-        exitcode
+        execution_output(output, opts)
       end
       alias_method :sudo, :execute
 
       def test(command, opts=nil)
-        @logger.info("Testing: #{command}")
-
-        # HACK: to speed up Vagrant 1.2 OS detection, skip checking for *nix OS
-        return false unless (command =~ /^uname|^cat \/etc|^cat \/proc|grep 'Fedora/).nil?
+        # If this is a *nix command with no Windows equivilant, assume failure
+        command = @cmd_filter.filter(command)
+        return false if command.empty?
 
         opts = { :error_check => false }.merge(opts || {})
         execute(command, opts) == 0
@@ -111,10 +106,21 @@ module VagrantPlugins
         )
       end
 
-      def raise_execution_error(opts, exit_code)
+      # Handles the raw WinRM shell result and converts it to a
+      # standard Vagrant communicator result
+      def execution_output(output, opts)
+        if opts[:shell] == :wql
+          return output
+        elsif opts[:error_check] && output[:exitcode] != 0
+          raise_execution_error(output, opts)
+        end
+        output[:exitcode]
+      end
+
+      def raise_execution_error(output, opts)
         # The error classes expect the translation key to be _key, but that makes for an ugly
         # configuration parameter, so we set it here from `error_key`
-        msg = "Command execution failed with an exit code of #{exit_code}"
+        msg = "Command execution failed with an exit code of #{output[:exitcode]}"
         error_opts = opts.merge(:_key => opts[:error_key], :message => msg)
         raise opts[:error_class], error_opts
       end
diff --git a/plugins/communicators/winrm/scripts/command_alias.ps1 b/plugins/communicators/winrm/scripts/command_alias.ps1
deleted file mode 100644
index 0955db6d8..000000000
--- a/plugins/communicators/winrm/scripts/command_alias.ps1
+++ /dev/null
@@ -1,35 +0,0 @@
-function which {
-    $command = [Array](Get-Command $args[0] -errorAction SilentlyContinue)
-    if($null -eq $command)
-    {
-      exit 1
-    }
-    write-host $command[0].Definition
-    exit 0
-}
-
-function test ([Switch] $d, [String] $path) {
-  if(Test-Path $path)
-  {
-    exit 0
-  }
-  exit 1
-}
-
-function chmod {
-  exit 0
-}
-
-function chown {
-  exit 0
-}
-
-function mkdir ([Switch] $p, [String] $path)
-{
-  if(Test-Path $path)
-  {
-    exit 0
-  } else {
-    New-Item $path -Type Directory -Force | Out-Null
-  }
-}
diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index 772c8944d..131c79141 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -52,6 +52,9 @@ module VagrantPlugins
       end
 
       def powershell(command, &block)
+        # ensure an exit code
+        command << "\r\n"
+        command << "if ($LASTEXITCODE) { exit $LASTEXITCODE } else { exit 0 }"
         execute_shell(command, :powershell, &block)
       end
 
diff --git a/test/unit/plugins/communicators/winrm/command_filter_test.rb b/test/unit/plugins/communicators/winrm/command_filter_test.rb
new file mode 100644
index 000000000..e56d1cd10
--- /dev/null
+++ b/test/unit/plugins/communicators/winrm/command_filter_test.rb
@@ -0,0 +1,82 @@
+require File.expand_path("../../../../base", __FILE__)
+
+require Vagrant.source_root.join("plugins/communicators/winrm/command_filter")
+
+describe VagrantPlugins::CommunicatorWinRM::CommandFilter, :unit => true do
+
+  describe '.command_filters' do
+    it 'initializes all command filters in command filters directory' do
+      expect(subject.command_filters()).not_to be_empty
+    end
+  end
+
+  describe '.filter' do
+    it 'filters out uname commands' do
+      expect(subject.filter('uname -s stuff')).to eq('')
+    end
+
+    it 'filters out grep commands' do
+      expect(subject.filter("grep 'Fedora release [12][67890]' /etc/redhat-release")).to eq("")
+    end
+
+    it 'filters out which commands' do
+      expect(subject.filter('which ruby')).to include(
+        '[Array](Get-Command ruby -errorAction SilentlyContinue)')
+    end
+
+    it 'filters out test -d commands' do
+      expect(subject.filter('test -d /tmp/dir')).to include(
+        "$p = \"/tmp/dir\"")
+      expect(subject.filter('test -d /tmp/dir')).to include(
+        "if ((Test-Path $p) -and (get-item $p).PSIsContainer) {")
+    end
+
+    it 'filters out test -f commands' do
+      expect(subject.filter('test -f /tmp/file.txt')).to include(
+        "$p = \"/tmp/file.txt\"")
+      expect(subject.filter('test -f /tmp/file.txt')).to include(
+        "if ((Test-Path $p) -and (!(get-item $p).PSIsContainer)) {")
+    end
+
+    it 'filters out test -x commands' do
+      expect(subject.filter('test -x /tmp/file.txt')).to include(
+        "$p = \"/tmp/file.txt\"")
+      expect(subject.filter('test -x /tmp/file.txt')).to include(
+        "if ((Test-Path $p) -and (!(get-item $p).PSIsContainer)) {")
+    end
+
+    it 'filters out other test commands' do
+      expect(subject.filter('test -L /tmp/file.txt')).to include(
+        "$p = \"/tmp/file.txt\"")
+      expect(subject.filter('test -L /tmp/file.txt')).to include(
+        "if (Test-Path $p) {")
+    end
+
+    it 'filters out rm -Rf commands' do
+      expect(subject.filter('rm -Rf /some/dir')).to eq(
+        "rm '/some/dir' -recurse -force")
+    end
+
+    it 'filters out rm commands' do
+      expect(subject.filter('rm /some/dir')).to eq(
+        "rm '/some/dir' -force")
+    end
+
+    it 'filters out chown commands' do
+      expect(subject.filter("chown -R root '/tmp/dir'")).to eq('')
+    end
+
+    it 'filters out chmod commands' do
+      expect(subject.filter("chmod 0600 ~/.ssh/authorized_keys")).to eq('')
+    end
+
+    it 'filters out certain cat commands' do
+      expect(subject.filter("cat /etc/release | grep -i OmniOS")).to eq('')
+    end
+
+    it 'should not filter out other cat commands' do
+      expect(subject.filter("cat /tmp/somefile")).to eq('cat /tmp/somefile')
+    end
+  end
+
+end
diff --git a/test/unit/plugins/communicators/winrm/shell_test.rb b/test/unit/plugins/communicators/winrm/shell_test.rb
index 79d6970d8..477108b97 100644
--- a/test/unit/plugins/communicators/winrm/shell_test.rb
+++ b/test/unit/plugins/communicators/winrm/shell_test.rb
@@ -15,19 +15,19 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
 
   describe ".powershell" do
     it "should call winrm powershell" do
-      expect(session).to receive(:powershell).with("dir").and_return({ exitcode: 0 })
+      expect(session).to receive(:powershell).with(/^dir.+/).and_return({ exitcode: 0 })
       expect(subject.powershell("dir")[:exitcode]).to eq(0)
     end
 
     it "should raise auth error when exception message contains 401" do
-      expect(session).to receive(:powershell).with("dir").and_raise(
+      expect(session).to receive(:powershell).with(/^dir.+/).and_raise(
         StandardError.new("Oh no! a 401 SOAP error!"))
       expect { subject.powershell("dir") }.to raise_error(
         VagrantPlugins::CommunicatorWinRM::Errors::AuthError)
     end
 
     it "should raise an execution error when an exception occurs" do
-      expect(session).to receive(:powershell).with("dir").and_raise(
+      expect(session).to receive(:powershell).with(/^dir.+/).and_raise(
         StandardError.new("Oh no! a 500 SOAP error!"))
       expect { subject.powershell("dir") }.to raise_error(
         VagrantPlugins::CommunicatorWinRM::Errors::ExecutionError)