diff --git a/plugins/communicators/winrm/shell.rb b/plugins/communicators/winrm/shell.rb
index f55c8fb75..0ea9e3cbb 100644
--- a/plugins/communicators/winrm/shell.rb
+++ b/plugins/communicators/winrm/shell.rb
@@ -56,11 +56,15 @@ module VagrantPlugins
       def powershell(command, &block)
         # Ensure an exit code
         command += "\r\nif ($?) { exit 0 } else { if($LASTEXITCODE) { exit $LASTEXITCODE } else { exit 1 } }"
-        execute_with_rescue(executor.method("run_powershell_script"), command, &block)
+        session.create_executor do |executor|
+          execute_with_rescue(executor.method("run_powershell_script"), command, &block)
+        end
       end
 
       def cmd(command, &block)
-        execute_with_rescue(executor.method("run_cmd"), command, &block)
+        session.create_executor do |executor|
+          execute_with_rescue(executor.method("run_cmd"), command, &block)
+        end
       end
 
       def wql(query, &block)
@@ -172,10 +176,6 @@ module VagrantPlugins
         @session ||= new_session
       end
 
-      def executor
-        @executor ||= session.create_executor
-      end
-
       def endpoint
         case @config.transport.to_sym
         when :ssl
diff --git a/test/unit/plugins/communicators/winrm/shell_test.rb b/test/unit/plugins/communicators/winrm/shell_test.rb
index 5cf1f6810..0c77290c8 100644
--- a/test/unit/plugins/communicators/winrm/shell_test.rb
+++ b/test/unit/plugins/communicators/winrm/shell_test.rb
@@ -6,7 +6,7 @@ require Vagrant.source_root.join("plugins/communicators/winrm/config")
 describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
   include_context "unit"
 
-  let(:session) { double("winrm_session", create_executor: executor) }
+  let(:session) { double("winrm_session") }
   let(:executor) { double("command_executor") }
   let(:port) { config.transport == :ssl ? 5986 : 5985 }
   let(:config)  {
@@ -22,6 +22,8 @@ describe VagrantPlugins::CommunicatorWinRM::WinRMShell do
     end
   }
 
+  before { allow(session).to receive(:create_executor).and_yield(executor) }
+
   subject do
     described_class.new('localhost', port, config).tap do |comm|
       allow(comm).to receive(:new_session).and_return(session)