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)