diff --git a/image_creator/os_type/windows.py b/image_creator/os_type/windows.py
index f8e30f6621a229d748b02d58f816332b048b7e7b..a7f8e07fe14fc340771b3f0e74ff3d334a555f32 100644
--- a/image_creator/os_type/windows.py
+++ b/image_creator/os_type/windows.py
@@ -249,10 +249,9 @@ class Windows(OSBase):
             if not self._wait_on_file(monitor, token):
                 raise FatalError("Windows booting timed out.")
             else:
+                time.sleep(10)  # Just to be sure everything is up
                 self.out.success('done')
 
-            time.sleep(5)  # Just to be sure everything is up
-
             self.out.output("Disabling automatic logon ...", False)
             self._disable_autologon()
             self.out.success('done')
@@ -627,6 +626,8 @@ class Windows(OSBase):
 
         if rc != 0 and fatal:
             reason = stderr if len(stderr) else stdout
+            self.out.output("Command: `%s' failed. Reason: %s" %
+                            (command, reason))
             raise FatalError("Command: `%s' failed. Reason: %s" %
                              (command, reason))