--- Net/SMTP.php	2019-12-01 10:40:31.000000000 +1100
+++ Net/SMTP.php	2020-02-08 14:36:53.758318869 +1100
@@ -376,7 +376,9 @@
             return true;
         }
 
-        return PEAR::raiseError('Invalid response code received from server', $this->code);
+        // CRM-8744
+        $errorMessage = 'Invalid response code received from SMTP server while sending email.  This is often caused by a misconfiguration in Outbound Email settings. Please verify the settings at Administer CiviCRM >> Global Settings >> Outbound Email (SMTP).';
+        return PEAR::raiseError($errorMessage, $this->code, PEAR_ERROR_RETURN);
     }
 
     /**