diff --git a/plugins/communicators/winrm/command_filters/rm.rb b/plugins/communicators/winrm/command_filters/rm.rb
index efc533197..755a48896 100644
--- a/plugins/communicators/winrm/command_filters/rm.rb
+++ b/plugins/communicators/winrm/command_filters/rm.rb
@@ -31,9 +31,9 @@ module VagrantPlugins
 
           ret_cmd = ''
           if recurse
-            ret_cmd = "rm \"#{dir}\" -recurse -force"
+            ret_cmd = "if (Test-Path \"#{dir}\") {Remove-Item \"#{dir}\" -force -recurse}"
           else
-            ret_cmd = "if (Test-Path #{dir}) {Remove-Item #{dir} -force}"
+            ret_cmd = "if (Test-Path \"#{dir}\") {Remove-Item \"#{dir}\" -force}"
           end
           return ret_cmd
         end
diff --git a/plugins/provisioners/docker/client.rb b/plugins/provisioners/docker/client.rb
index fa13f9744..4293dffed 100644
--- a/plugins/provisioners/docker/client.rb
+++ b/plugins/provisioners/docker/client.rb
@@ -127,10 +127,8 @@ module VagrantPlugins
       def create_container(config)
         args = container_run_args(config)
 
-        @machine.communicate.sudo %[rm -f #{config[:cidfile]}
-                                  ]
-        @machine.communicate.sudo %[docker run #{args}
-                                  ]
+        @machine.communicate.sudo %[rm -f "#{config[:cidfile]}"]
+        @machine.communicate.sudo %[docker run #{args}]
 
         sha  = Digest::SHA1.hexdigest(args)
         container_data_path(config).open("w+") do |f|
diff --git a/test/unit/plugins/communicators/winrm/command_filter_test.rb b/test/unit/plugins/communicators/winrm/command_filter_test.rb
index 79b8808f8..151227b35 100644
--- a/test/unit/plugins/communicators/winrm/command_filter_test.rb
+++ b/test/unit/plugins/communicators/winrm/command_filter_test.rb
@@ -54,20 +54,22 @@ 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")
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force -recurse}")
       expect(subject.filter('rm -fr /some/dir')).to eq(
-        "rm \"/some/dir\" -recurse -force")
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force -recurse}")
       expect(subject.filter('rm -r /some/dir')).to eq(
-        "rm \"/some/dir\" -recurse -force")
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force -recurse}")
       expect(subject.filter('rm -r "/some/dir"')).to eq(
-        "rm \"/some/dir\" -recurse -force")
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force -recurse}")
     end
 
     it 'filters out rm commands' do
       expect(subject.filter('rm /some/dir')).to eq(
-                                                  "if (Test-Path /some/dir) {Remove-Item /some/dir -force}")
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force}")
       expect(subject.filter('rm -f /some/dir')).to eq(
-                                                     "if (Test-Path /some/dir) {Remove-Item /some/dir -force}")
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force}")
+      expect(subject.filter('rm -f "/some/dir"')).to eq(
+        "if (Test-Path \"/some/dir\") {Remove-Item \"/some/dir\" -force}")
     end
 
     it 'filters out mkdir commands' do