diff --git a/plugins/communicators/winrm/command_filter.rb b/plugins/communicators/winrm/command_filter.rb
index f3ade202d..66a8b1d47 100644
--- a/plugins/communicators/winrm/command_filter.rb
+++ b/plugins/communicators/winrm/command_filter.rb
@@ -11,6 +11,7 @@ module VagrantPlugins
         "test",
         "uname",
         "which",
+        "mkdir",
       ]
 
       # Filter the given Vagrant command to ensure compatibility with Windows
diff --git a/plugins/communicators/winrm/command_filters/mkdir.rb b/plugins/communicators/winrm/command_filters/mkdir.rb
new file mode 100755
index 000000000..9d399c2f3
--- /dev/null
+++ b/plugins/communicators/winrm/command_filters/mkdir.rb
@@ -0,0 +1,25 @@
+module VagrantPlugins
+  module CommunicatorWinRM
+    module CommandFilters
+      # Converts a *nix 'mkdir' command to a PowerShell equivalent
+      class Mkdir
+        def filter(command)
+          # mkdir -p /some/dir
+          # mkdir /some/dir
+          cmd_parts = command.strip.split(/\s+/)
+          dir = cmd_parts.pop
+          while !dir.nil? && dir.start_with?('-')
+            dir = cmd_parts.pop
+          end
+          # This will ignore any -p switches, which are redundant in PowerShell,
+          # and ambiguous in PowerShell 4+
+          return "mkdir #{dir} -force"
+        end
+
+        def accept?(command)
+          command.start_with?('mkdir ')
+        end
+      end
+    end
+  end
+end
diff --git a/plugins/communicators/winrm/command_filters/rm.rb b/plugins/communicators/winrm/command_filters/rm.rb
index 5c0dd4c2b..251e26076 100644
--- a/plugins/communicators/winrm/command_filters/rm.rb
+++ b/plugins/communicators/winrm/command_filters/rm.rb
@@ -5,14 +5,35 @@ module VagrantPlugins
       class Rm
         def filter(command)
           # rm -Rf /some/dir
+          # rm -R /some/dir
+          # rm -R -f /some/dir
+          # rm -f /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"
+
+          # Figure out if we need to do this recursively
+          recurse = false
+          cmd_parts.each do |k|
+            argument = k.downcase
+            if argument == '-r' || argument == '-rf' || argument == '-fr'
+              recurse = true
+              break
+            end
           end
-          return "rm '#{dir}' -force"
+          
+          # Figure out which argument is the path
+          dir = cmd_parts.pop
+          while !dir.nil? && dir.start_with?('-')
+            dir = cmd_parts.pop
+          end
+
+          ret_cmd = ''
+          if recurse
+            ret_cmd = "rm #{dir} -recurse -force"
+          else
+            ret_cmd = "rm #{dir} -force"
+          end
+          return ret_cmd
         end
 
         def accept?(command)
diff --git a/test/unit/plugins/communicators/winrm/command_filter_test.rb b/test/unit/plugins/communicators/winrm/command_filter_test.rb
index f7ed9eb54..251defc7b 100644
--- a/test/unit/plugins/communicators/winrm/command_filter_test.rb
+++ b/test/unit/plugins/communicators/winrm/command_filter_test.rb
@@ -52,14 +52,27 @@ describe VagrantPlugins::CommunicatorWinRM::CommandFilter, unit: true do
         "if (Test-Path $p) {")
     end
 
-    it 'filters out rm -Rf commands' do
+    it 'filters out rm recurse commands' do
       expect(subject.filter('rm -Rf /some/dir')).to eq(
-        "rm '/some/dir' -recurse -force")
+        "rm /some/dir -recurse -force")
+      expect(subject.filter('rm -fr /some/dir')).to eq(
+        "rm /some/dir -recurse -force")
+      expect(subject.filter('rm -r /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")
+        "rm /some/dir -force")
+      expect(subject.filter('rm -f /some/dir')).to eq(
+        "rm /some/dir -force")
+    end
+
+    it 'filters out mkdir commands' do
+      expect(subject.filter('mkdir /some/dir')).to eq(
+        "mkdir /some/dir -force")
+      expect(subject.filter('mkdir -p /some/dir')).to eq(
+        "mkdir /some/dir -force")
     end
 
     it 'filters out chown commands' do