diff --git a/plugins/communicators/winssh/communicator.rb b/plugins/communicators/winssh/communicator.rb
index 3ea012f6185..21cad5863a9 100644
--- a/plugins/communicators/winssh/communicator.rb
+++ b/plugins/communicators/winssh/communicator.rb
@@ -44,7 +44,7 @@ def shell_execute(connection, command, **opts)
           stderr_data_buffer = ''
 
           @logger.debug("Base SSH exec command: #{command}")
-          command = "$ProgressPreference = 'SilentlyContinue';Write-Output #{CMD_GARBAGE_MARKER};[Console]::Error.WriteLine('#{CMD_GARBAGE_MARKER}');#{command}"
+          command = "$ProgressPreference = 'SilentlyContinue';Write-Output #{CMD_GARBAGE_MARKER};[Console]::Error.WriteLine('#{CMD_GARBAGE_MARKER}');#{command};$?"
 
           ch.exec(command) do |ch2, _|
             # Setup the channel callbacks so we can get data and exit status
@@ -96,6 +96,9 @@ def shell_execute(connection, command, **opts)
               # probably done. This fixes up issues with hanging.
               ch.close
             end
+            
+            # Send eof to let server know we're done
+            ch2.eof!
 
           end
         end