diff --git a/infection_monkey/config.py b/infection_monkey/config.py
index 633534b84..0ee609cac 100644
--- a/infection_monkey/config.py
+++ b/infection_monkey/config.py
@@ -116,10 +116,14 @@ class Configuration(object):
     dropper_date_reference_path_windows = r"%windir%\system32\kernel32.dll"
     dropper_date_reference_path_linux = '/bin/sh'
     dropper_target_path = r"C:\Windows\monkey.exe"
-    # TODO: move and rename
-    dropper_upgrade_win_64_temp_path = r"C:\Windows\monkey64.exe"
     dropper_target_path_linux = '/tmp/monkey'
 
+    ###########################
+    # Windows upgrader config
+    ###########################
+
+    windows_upgrader_temp_path = r"C:\Windows\monkey64.exe"
+
     ###########################
     # Kill file
     ###########################
diff --git a/infection_monkey/example.conf b/infection_monkey/example.conf
index 3ebe3f122..8acf8729f 100644
--- a/infection_monkey/example.conf
+++ b/infection_monkey/example.conf
@@ -23,7 +23,7 @@
     "dropper_log_path_linux": "/tmp/user-1562",
     "dropper_set_date": true,
     "dropper_target_path": "C:\\Windows\\monkey.exe",
-    "dropper_upgrade_win_64_temp_path": "C:\\Windows\\monkey64.exe",
+    "windows_upgrader_temp_path": "C:\\Windows\\monkey64.exe",
     "dropper_target_path_linux": "/tmp/monkey",
 
 
diff --git a/infection_monkey/monkey.py b/infection_monkey/monkey.py
index 6e0932ff2..0ca85b6b8 100644
--- a/infection_monkey/monkey.py
+++ b/infection_monkey/monkey.py
@@ -75,6 +75,7 @@ class InfectionMonkey(object):
         ControlClient.find_server(default_tunnel=self._default_tunnel)
 
         if WindowsUpgrader.should_upgrade():
+            LOG.info("32bit monkey running on 64bit Windows. Upgrading.")
             WindowsUpgrader.upgrade(self._opts)
             return
 
diff --git a/infection_monkey/windows_upgrader.py b/infection_monkey/windows_upgrader.py
index d2c5aee31..994a17f96 100644
--- a/infection_monkey/windows_upgrader.py
+++ b/infection_monkey/windows_upgrader.py
@@ -1,8 +1,11 @@
+import logging
 import os
 import struct
 import subprocess
 import sys
 
+import time
+
 import monkeyfs
 from config import WormConfiguration
 from control import ControlClient
@@ -11,6 +14,8 @@ from model import DROPPER_CMDLINE_WINDOWS
 
 __author__ = 'itay.mizeretz'
 
+LOG = logging.getLogger(__name__)
+
 if "win32" == sys.platform:
     from win32process import DETACHED_PROCESS
 else:
@@ -40,7 +45,7 @@ class WindowsUpgrader(object):
         monkey_64_path = ControlClient.download_monkey_exe_by_os(True, False)
         with monkeyfs.open(monkey_64_path, "rb") as downloaded_monkey_file:
             monkey_bin = downloaded_monkey_file.read()
-        with open(WormConfiguration.dropper_upgrade_win_64_temp_path, 'wb') as written_monkey_file:
+        with open(WormConfiguration.windows_upgrader_temp_path, 'wb') as written_monkey_file:
             written_monkey_file.write(monkey_bin)
 
         depth = int(opts.depth) if opts.depth is not None else None
@@ -48,9 +53,15 @@ class WindowsUpgrader(object):
             opts.parent, opts.tunnel, opts.server, depth, WormConfiguration.dropper_target_path)
 
         monkey_cmdline = DROPPER_CMDLINE_WINDOWS % {
-            'dropper_path': WormConfiguration.dropper_upgrade_win_64_temp_path} + monkey_options
+            'dropper_path': WormConfiguration.windows_upgrader_temp_path} + monkey_options
 
-        print monkey_cmdline
         monkey_process = subprocess.Popen(monkey_cmdline, shell=True,
                                           stdin=None, stdout=None, stderr=None,
                                           close_fds=True, creationflags=DETACHED_PROCESS)
+
+        LOG.info("Executed 64bit monkey process (PID=%d) with command line: %s",
+                 monkey_process.pid, monkey_cmdline)
+
+        time.sleep(3)
+        if monkey_process.poll() is not None:
+            LOG.warn("Seems like monkey died too soon")
diff --git a/monkey_island/cc/services/config.py b/monkey_island/cc/services/config.py
index f558eb8dc..981319db4 100644
--- a/monkey_island/cc/services/config.py
+++ b/monkey_island/cc/services/config.py
@@ -350,7 +350,14 @@ SCHEMA = {
                             "type": "integer",
                             "default": 60,
                             "description": "Time to keep tunnel open before going down after last exploit (in seconds)"
-                        }
+                        },
+                        "windows_upgrader_temp_path": {
+                            "title": "Temporary upgrade path for 64bit monkey on Windows",
+                            "type": "string",
+                            "default": "C:\\Windows\\monkey64.exe",
+                            "description": "Determines where should the dropper place the 64 bit monkey while"
+                                           " upgrading on a Windows machine"
+                        },
                     }
                 },
                 "classes": {
@@ -446,13 +453,6 @@ SCHEMA = {
                             "default": "C:\\Windows\\monkey.exe",
                             "description": "Determines where should the dropper place the monkey on a Windows machine"
                         },
-                        "dropper_upgrade_win_64_temp_path": {
-                            "title": "Temporary upgrade path for 64bit monkey on Windows",
-                            "type": "string",
-                            "default": "C:\\Windows\\monkey64.exe",
-                            "description": "Determines where should the dropper place the 64 bit monkey while"
-                                           " upgrading on a Windows machine"
-                        },
                         "dropper_try_move_first": {
                             "title": "Try to move first",
                             "type": "boolean",