diff --git a/Diagnostic/Utils/misc_helpers.py b/Diagnostic/Utils/misc_helpers.py
index d082b9c72..2d2723627 100644
--- a/Diagnostic/Utils/misc_helpers.py
+++ b/Diagnostic/Utils/misc_helpers.py
@@ -150,14 +150,12 @@ def log_and_report_failed_config_generation(self, ext_event_type, config_invalid
                     secrets in the protected settings. This is for logging to Geneva for diagnostic purposes.
         :return: None
         """
-        config_invalid_log = "Invalid config settings given: " + config_invalid_reason + \
-                             ". Can't proceed, although this install/enable operation is reported as successful so " \
-                             "the VM can complete successful startup."
-        self._logger_log(config_invalid_log)
-        self._status_reporter(ext_event_type, 'success', '0', config_invalid_log)
+        config_invalid_log = "Invalid config settings given: {0}".format(config_invalid_reason)
+        self._logger_error(config_invalid_log)
+        self._status_reporter(ext_event_type, 'error', '2', config_invalid_log)
         self._waagent_event_adder(name=self._ext_name,
                                   op=ext_event_type,
-                                  isSuccess=True,  # Note this is True, because it is a user error.
+                                  isSuccess=False,
                                   version=self._ext_ver,
                                   message="Invalid handler settings encountered: {0}".format(redacted_handler_settings))
 
@@ -169,14 +167,12 @@ def log_and_report_invalid_mdsd_cfg(self, ext_event_type, config_validate_cmd_ms
         :param mdsd_cfg_xml: Content of xmlCfg.xml to be sent to Geneva
         :return: None
         """
-        message = "Problem(s) detected in generated mdsd configuration. Can't enable, although this install/enable " \
-                  "operation is reported as successful so the VM can complete successful startup. Linux Diagnostic " \
-                  "Extension will exit. Config validation message: {0}".format(config_validate_cmd_msg)
-        self._logger_log(message)
-        self._status_reporter(ext_event_type, 'success', '0', message)
+        message = "Problem(s) detected in generated mdsd configuration. Config validation message: {0}".format(config_validate_cmd_msg)
+        self._logger_error(message)
+        self._status_reporter(ext_event_type, 'error', '2', message)
         self._waagent_event_adder(name=self._ext_name,
                       op=ext_event_type,
-                      isSuccess=True,  # Note this is True, because it is a user error.
+                      isSuccess=False,
                       version=self._ext_ver,
                       message="Problem(s) detected in generated mdsd configuration: {0}".format(mdsd_cfg_xml))
 
diff --git a/Diagnostic/diagnostic.py b/Diagnostic/diagnostic.py
index e674e261c..2debf49a1 100755
--- a/Diagnostic/diagnostic.py
+++ b/Diagnostic/diagnostic.py
@@ -261,13 +261,12 @@ def check_for_supported_waagent_and_distro_version():
             return False
 
     if g_dist_config is None:
-        msg = ("LAD does not support distro/version ({0}); not installed. This extension install/enable operation is "
-               "still considered a success as it's an external error.").format(str(platform.dist()))
+        msg = ("LAD does not support distro/version ({0}); not installed.").format(str(platform.dist()))
         hutil.log(msg)
-        hutil.do_status_report(g_ext_op_type, "success", '0', msg)
+        hutil.do_status_report(g_ext_op_type, 'error', '2', msg)
         waagent.AddExtensionEvent(name=hutil.get_name(),
                                   op=g_ext_op_type,
-                                  isSuccess=True,
+                                  isSuccess=False,
                                   version=hutil.get_extension_version(),
                                   message="Can't be installed on this OS " + str(platform.dist()))
         return False
@@ -496,7 +495,7 @@ def start_mdsd(configurator):
                                                        g_mdsd_bin_path, xml_file, g_ext_dir)
     config_validate_cmd_status, config_validate_cmd_msg = RunGetOutput(config_validate_cmd)
     if config_validate_cmd_status is not 0:
-        # Invalid config. Log error and report success.
+        # Invalid config, report error.
         g_lad_log_helper.log_and_report_invalid_mdsd_cfg(g_ext_op_type,
                                                          config_validate_cmd_msg, read_file_to_string(xml_file))
         return