diff --git a/plugins/communicators/winrm/command_filters/mkdir.rb b/plugins/communicators/winrm/command_filters/mkdir.rb
index 9d399c2f3..d14ccbc23 100644
--- a/plugins/communicators/winrm/command_filters/mkdir.rb
+++ b/plugins/communicators/winrm/command_filters/mkdir.rb
@@ -1,3 +1,5 @@
+require "shellwords"
+
 module VagrantPlugins
   module CommunicatorWinRM
     module CommandFilters
@@ -6,14 +8,14 @@ module VagrantPlugins
         def filter(command)
           # mkdir -p /some/dir
           # mkdir /some/dir
-          cmd_parts = command.strip.split(/\s+/)
+          cmd_parts = Shellwords.split(command.strip)
           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"
+          return "mkdir \"#{dir}\" -force"
         end
 
         def accept?(command)
diff --git a/plugins/communicators/winrm/command_filters/rm.rb b/plugins/communicators/winrm/command_filters/rm.rb
index 8ef79f148..9133febf6 100644
--- a/plugins/communicators/winrm/command_filters/rm.rb
+++ b/plugins/communicators/winrm/command_filters/rm.rb
@@ -1,3 +1,5 @@
+require "shellwords"
+
 module VagrantPlugins
   module CommunicatorWinRM
     module CommandFilters
@@ -9,7 +11,7 @@ module VagrantPlugins
           # rm -R -f /some/dir
           # rm -f /some/dir
           # rm /some/dir
-          cmd_parts = command.strip.split(/\s+/)
+          cmd_parts = Shellwords.split(command.strip)
 
           # Figure out if we need to do this recursively
           recurse = false
@@ -29,9 +31,9 @@ module VagrantPlugins
 
           ret_cmd = ''
           if recurse
-            ret_cmd = "rm #{dir} -recurse -force"
+            ret_cmd = "rm \"#{dir}\" -recurse -force"
           else
-            ret_cmd = "rm #{dir} -force"
+            ret_cmd = "rm \"#{dir}\" -force"
           end
           return ret_cmd
         end
diff --git a/plugins/communicators/winrm/command_filters/test.rb b/plugins/communicators/winrm/command_filters/test.rb
index bee71505d..58b7fbf0d 100644
--- a/plugins/communicators/winrm/command_filters/test.rb
+++ b/plugins/communicators/winrm/command_filters/test.rb
@@ -1,3 +1,5 @@
+require "shellwords"
+
 module VagrantPlugins
   module CommunicatorWinRM
     module CommandFilters
@@ -9,7 +11,7 @@ module VagrantPlugins
           # test -L /somelink
           # test -x /tmp/some.exe
 
-          cmd_parts = command.strip.split(/\s+/)
+          cmd_parts = Shellwords.split(command.strip)
           flag = cmd_parts[1]
           path = cmd_parts[2]
 
diff --git a/plugins/communicators/winrm/command_filters/which.rb b/plugins/communicators/winrm/command_filters/which.rb
index 2cc23a993..1d7a12bdc 100644
--- a/plugins/communicators/winrm/command_filters/which.rb
+++ b/plugins/communicators/winrm/command_filters/which.rb
@@ -1,12 +1,14 @@
+require "shellwords"
+
 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]
+          executable = Shellwords.split(command.strip)[1]
           return <<-EOH
-            $command = [Array](Get-Command #{executable} -errorAction SilentlyContinue)
+            $command = [Array](Get-Command "#{executable}" -errorAction SilentlyContinue)
             if ($null -eq $command) { exit 1 }
             write-host $command[0].Definition
             exit 0
diff --git a/test/unit/plugins/communicators/winrm/command_filter_test.rb b/test/unit/plugins/communicators/winrm/command_filter_test.rb
index 251defc7b..0bd6e7ba8 100644
--- a/test/unit/plugins/communicators/winrm/command_filter_test.rb
+++ b/test/unit/plugins/communicators/winrm/command_filter_test.rb
@@ -21,7 +21,7 @@ describe VagrantPlugins::CommunicatorWinRM::CommandFilter, unit: true do
 
     it 'filters out which commands' do
       expect(subject.filter('which ruby')).to include(
-        '[Array](Get-Command ruby -errorAction SilentlyContinue)')
+        '[Array](Get-Command "ruby" -errorAction SilentlyContinue)')
     end
 
     it 'filters out test -d commands' do
@@ -54,25 +54,31 @@ describe VagrantPlugins::CommunicatorWinRM::CommandFilter, unit: true 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")
+        "rm \"/some/dir\" -recurse -force")
       expect(subject.filter('rm -r /some/dir')).to eq(
-        "rm /some/dir -recurse -force")
+        "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")
+        "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")
+        "mkdir \"/some/dir\" -force")
       expect(subject.filter('mkdir -p /some/dir')).to eq(
-        "mkdir /some/dir -force")
+        "mkdir \"/some/dir\" -force")
+      expect(subject.filter('mkdir "/some/dir"')).to eq(
+        "mkdir \"/some/dir\" -force")
     end
 
     it 'filters out chown commands' do