diff --git a/plugins/communicators/winssh/communicator.rb b/plugins/communicators/winssh/communicator.rb
index fb82a4a80..208ec0f90 100644
--- a/plugins/communicators/winssh/communicator.rb
+++ b/plugins/communicators/winssh/communicator.rb
@@ -48,28 +48,27 @@ module VagrantPlugins
             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')
 Remove-Item #{remote_name}
 Write-Host #{CMD_GARBAGE_MARKER}
 [Console]::Error.WriteLine("#{CMD_GARBAGE_MARKER}")
 #{command}
 SCRIPT
+              base_cmd = "powershell -file #{remote_name}"
             else
-              base_cmd = remote_name
               tfile.puts <<-SCRIPT.force_encoding('ASCII-8BIT')
+DEL #{remote_name}
 ECHO OFF
 ECHO #{CMD_GARBAGE_MARKER}
 ECHO #{CMD_GARBAGE_MARKER} 1>&2
 #{command}
 SCRIPT
+              base_cmd = "cmd /q /c #{remote_name}"
             end
 
             tfile.close
             upload(tfile.path, remote_name)
             tfile.delete
-
-            base_cmd = shell_cmd(opts.merge(shell: base_cmd))
           end
 
           @logger.debug("Base SSH exec command: #{base_cmd}")
diff --git a/plugins/provisioners/shell/provisioner.rb b/plugins/provisioners/shell/provisioner.rb
index a86a43a42..34bc49448 100644
--- a/plugins/provisioners/shell/provisioner.rb
+++ b/plugins/provisioners/shell/provisioner.rb
@@ -194,19 +194,20 @@ module VagrantPlugins
           @machine.communicate.tap do |comm|
             # Make sure that the upload path has an extension, since
             # having an extension is critical for Windows execution
-            if File.extname(upload_path) == ""
-              upload_path += File.extname(path.to_s)
+            winrm_upload_path = upload_path
+            if File.extname(winrm_upload_path) == ""
+              winrm_upload_path += File.extname(path.to_s)
             end
 
             # Upload it
-            comm.upload(path.to_s, upload_path)
+            comm.upload(path.to_s, winrm_upload_path)
 
             # Build the environment
             env = config.env.map { |k,v| "$env:#{k} = #{quote_and_escape(v.to_s)}" }
             env = env.join("; ")
 
             # Calculate the path that we'll be executing
-            exec_path = upload_path
+            exec_path = winrm_upload_path
             exec_path.gsub!('/', '\\')
             exec_path = "c:#{exec_path}" if exec_path.start_with?("\\")
 
diff --git a/test/unit/plugins/provisioners/shell/provisioner_test.rb b/test/unit/plugins/provisioners/shell/provisioner_test.rb
index c3b566df3..dd83c42e4 100644
--- a/test/unit/plugins/provisioners/shell/provisioner_test.rb
+++ b/test/unit/plugins/provisioners/shell/provisioner_test.rb
@@ -416,4 +416,52 @@ describe "Vagrant::Shell::Provisioner" do
       end
     end
   end
+
+  describe "#provision_winrm" do
+    let(:config) {
+      double(
+        :config,
+        :args                            => "doesn't matter",
+        :env                             => {},
+        :upload_path                     => "arbitrary",
+        :remote?                         => false,
+        :path                            => "script/info.ps1",
+        :binary                          => false,
+        :md5                             => nil,
+        :sha1                            => 'EXPECTED_VALUE',
+        :sha256                          => nil,
+        :sha384                          => nil,
+        :sha512                          => nil,
+        :reset                           => false,
+        :reboot                          => false,
+        :powershell_args                 => "",
+        :name                            => nil,
+        :privileged                      => false,
+        :powershell_elevated_interactive => false
+      )
+    }
+
+    let(:vsp) {
+      VagrantPlugins::Shell::Provisioner.new(machine, config)
+    }
+
+    let(:communicator) { double("communicator") }
+    let(:guest) { double("guest") }
+    let(:ui) { double("ui") }
+
+    before {
+      allow(guest).to receive(:capability?).with(:wait_for_reboot).and_return(false)
+      allow(ui).to receive(:detail)
+      allow(communicator).to receive(:sudo)
+      allow(machine).to receive(:communicate).and_return(communicator)
+      allow(machine).to receive(:guest).and_return(guest)
+      allow(machine).to receive(:ui).and_return(ui)
+      allow(vsp).to receive(:with_script_file).and_yield(config.path)
+    }
+
+    it "ensures that files are uploaded with an extension" do
+      expect(communicator).to receive(:upload).with(config.path, /arbitrary.ps1$/)
+      vsp.send(:provision_winrm, "")
+    end
+  end
 end
diff --git a/test/unit/vagrant/util/platform_test.rb b/test/unit/vagrant/util/platform_test.rb
index 6b71329e9..9e0506614 100644
--- a/test/unit/vagrant/util/platform_test.rb
+++ b/test/unit/vagrant/util/platform_test.rb
@@ -533,11 +533,11 @@ EOF
         expect(subject.wsl_drvfs_path?("/home/vagrant/some/path")).to be_falsey
       end
     end
+  end
 
-    describe ".unix_windows_path" do
-      it "takes a windows path and returns a unixy path" do
-        expect(subject.unix_windows_path("C:\\Temp\\Windows")).to eq("C:/Temp/Windows")
-      end
+  describe ".unix_windows_path" do
+    it "takes a windows path and returns a POSIX-like path" do
+      expect(subject.unix_windows_path("C:\\Temp\\Windows")).to eq("C:/Temp/Windows")
     end
   end
 end