diff --git a/plugins/communicators/ssh/communicator.rb b/plugins/communicators/ssh/communicator.rb
index 9389e83b2..05d93f7ac 100644
--- a/plugins/communicators/ssh/communicator.rb
+++ b/plugins/communicators/ssh/communicator.rb
@@ -227,6 +227,7 @@ module VagrantPlugins
           command:     command,
           shell:       nil,
           sudo:        false,
+          force_raw:   false
         }.merge(opts || {})
 
         opts[:good_exit] = Array(opts[:good_exit])
@@ -238,6 +239,7 @@ module VagrantPlugins
           shell_opts = {
             sudo: opts[:sudo],
             shell: opts[:shell],
+            force_raw: opts[:force_raw]
           }
 
           shell_execute(connection, command, **shell_opts) do |type, data|
diff --git a/plugins/communicators/winssh/communicator.rb b/plugins/communicators/winssh/communicator.rb
index 00726c2d3..d2d0de60a 100644
--- a/plugins/communicators/winssh/communicator.rb
+++ b/plugins/communicators/winssh/communicator.rb
@@ -15,11 +15,13 @@ module VagrantPlugins
       def shell_execute(connection, command, **opts)
         opts = {
           sudo: false,
-          shell: nil
+          shell: nil,
+          force_raw: false
         }.merge(opts)
 
-        sudo  = opts[:sudo]
-        shell = (opts[:shell] || machine_config_ssh.shell).to_s
+        sudo      = opts[:sudo]
+        shell     = (opts[:shell] || machine_config_ssh.shell).to_s
+        force_raw = opts[:force_raw]
 
         @logger.info("Execute: #{command} (sudo=#{sudo.inspect})")
         exit_status = nil
@@ -31,33 +33,38 @@ module VagrantPlugins
           stderr_marker_found = false
           stderr_data_buffer = ''
 
-          tfile = Tempfile.new('vagrant-ssh')
-          remote_ext = shell == "powershell" ? "ps1" : "bat"
-          remote_name = "#{machine_config_ssh.upload_directory}\\#{File.basename(tfile.path)}.#{remote_ext}"
+          if force_raw
+            base_cmd = "cmd /Q /C #{command}"
+          else
+            tfile = Tempfile.new('vagrant-ssh')
+            remote_ext = shell == "powershell" ? "ps1" : "bat"
+            remote_name = "#{machine_config_ssh.upload_directory}\\#{File.basename(tfile.path)}.#{remote_ext}"
 
-          if shell == "powershell"
-            base_cmd = "powershell -File #{remote_name}"
-            tfile.puts <<-SCRIPT.force_encoding('ASCII-8BIT')
+            if shell == "powershell"
+              base_cmd = "powershell -File #{remote_name}"
+              tfile.puts <<-SCRIPT.force_encoding('ASCII-8BIT')
 Remove-Item #{remote_name}
 Write-Host #{CMD_GARBAGE_MARKER}
 [Console]::Error.WriteLine("#{CMD_GARBAGE_MARKER}")
 #{command}
 SCRIPT
-          else
-            base_cmd = remote_name
-            tfile.puts <<-SCRIPT.force_encoding('ASCII-8BIT')
+            else
+              base_cmd = remote_name
+              tfile.puts <<-SCRIPT.force_encoding('ASCII-8BIT')
 ECHO OFF
 ECHO #{CMD_GARBAGE_MARKER}
 ECHO #{CMD_GARBAGE_MARKER} 1>&2
 #{command}
 SCRIPT
+            end
+
+            tfile.close
+            upload(tfile.path, remote_name)
+            tfile.delete
+
+            base_cmd = shell_cmd(opts.merge(shell: base_cmd))
           end
 
-          tfile.close
-          upload(tfile.path, remote_name, mkdir: false)
-          tfile.delete
-
-          base_cmd = shell_cmd(opts.merge(shell: base_cmd))
           @logger.debug("Base SSH exec command: #{base_cmd}")
 
           ch.exec(base_cmd) do |ch2, _|
@@ -156,13 +163,7 @@ SCRIPT
         @machine.config.winssh
       end
 
-      def upload(from, to, **opts)
-        opts = {
-          mkdir: true
-        }.merge(opts)
-
-        mkdir = opts[:mkdir]
-
+      def upload(from, to)
         to = Vagrant::Util::Platform.unix_windows_path(to)
         @logger.debug("Uploading: #{from} to #{to}")
 
@@ -183,7 +184,7 @@ SCRIPT
                 next if entry == "." || entry == ".."
                 full_path = File.join(path, entry)
                 dest = File.join(to, path.sub(/^#{Regexp.escape(from)}/, ""))
-                create_remote_directory(dest) if mkdir
+                create_remote_directory(dest)
                 uploader.call(full_path, dest)
               end
             else
@@ -196,7 +197,7 @@ SCRIPT
                 end
               end
               @logger.debug("Ensuring remote directory exists for destination upload")
-              create_remote_directory(File.dirname(dest)) if mkdir
+              create_remote_directory(File.dirname(dest))
               @logger.debug("Uploading file #{path} to remote #{dest}")
               upload_file = File.open(path, "rb")
               begin
@@ -221,8 +222,8 @@ SCRIPT
           to: to.to_s
       end
 
-      def create_remote_directory(dir)
-        execute("dir \"#{dir}\"\n if errorlevel 1 (mkdir \"#{dir}\")", shell: "cmd")
+      def create_remote_directory(dir, force_raw=false)
+        execute("dir \"#{dir}\"\n if errorlevel 1 (mkdir \"#{dir}\")", shell: "cmd", force_raw: force_raw)
       end
     end
   end
diff --git a/test/unit/plugins/communicators/winssh/communicator_test.rb b/test/unit/plugins/communicators/winssh/communicator_test.rb
index 931d51db3..8370e93db 100644
--- a/test/unit/plugins/communicators/winssh/communicator_test.rb
+++ b/test/unit/plugins/communicators/winssh/communicator_test.rb
@@ -203,6 +203,23 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
         expect(stderr).to eq("Dir1\nDir2\n")
       end
     end
+
+    context "with force_raw set to true" do
+      it "does not write to a temp file" do
+        expect(ssh_cmd_file).to_not receive(:puts)
+        communicator.execute("dir", force_raw: true)
+      end
+
+      it "does not upload a wrapper script" do
+        expect(communicator).to_not receive(:upload)
+        communicator.execute("dir", force_raw: true)
+      end
+
+      it "executes the base command" do
+        expect(channel).to receive(:exec).with(/dir/)
+        expect(communicator.execute("dir", force_raw: true)).to eq(0)
+      end
+    end
   end
 
   describe ".test" do
@@ -527,12 +544,4 @@ describe VagrantPlugins::CommunicatorWinSSH::Communicator do
       end
     end
   end
-
-  describe "#shell_execute" do
-    before(&connection_setup)
-    it "should not create a directory for the command wrapper script" do
-      expect(communicator).to receive(:upload).with(anything, anything, hash_including(mkdir: false))
-      communicator.shell_execute(connection, "dir")
-    end
-  end
 end