diff --git a/infection_monkey/windows_upgrader.py b/infection_monkey/windows_upgrader.py
index cbd879c15..4ee0462c5 100644
--- a/infection_monkey/windows_upgrader.py
+++ b/infection_monkey/windows_upgrader.py
@@ -32,10 +32,14 @@ class WindowsUpgrader(object):
 
     @staticmethod
     def upgrade(opts):
-        monkey_64_path = ControlClient.download_monkey_exe_by_os(True, False)
-        with monkeyfs.open(monkey_64_path, "rb") as downloaded_monkey_file:
-            with open(WormConfiguration.dropper_target_path_win_64, 'wb') as written_monkey_file:
-                shutil.copyfileobj(downloaded_monkey_file, written_monkey_file)
+        try:
+            monkey_64_path = ControlClient.download_monkey_exe_by_os(True, False)
+            with monkeyfs.open(monkey_64_path, "rb") as downloaded_monkey_file:
+                with open(WormConfiguration.dropper_target_path_win_64, 'wb') as written_monkey_file:
+                    shutil.copyfileobj(downloaded_monkey_file, written_monkey_file)
+        except (IOError, AttributeError):
+            LOG.error("Failed to download the Monkey to the target path.")
+            return
 
         monkey_options = build_monkey_commandline_explicitly(opts.parent, opts.tunnel, opts.server, opts.depth)