diff --git a/ennstatus/api/functions.py b/ennstatus/api/functions.py
--- a/ennstatus/api/functions.py
+++ b/ennstatus/api/functions.py
@@ -6,6 +6,8 @@ from datetime import datetime
 
 import pygeoip
 
+from flask import current_app
+
 from ennstatus.status.functions import _send_mail
 
 
@@ -74,6 +76,7 @@ def check_json_format(server):
 
 def _send_offline_mail(server_name, last_updated):
 
+    current_app.logger.info('Sending tor status offline mail!')
     subject = '[Ennstatus] %s Tor status went offline'
     _send_mail(server_name, last_updated, subject)
     mail_cache[server_name] = datetime.utcnow()
@@ -107,17 +110,24 @@ def update_server(server, ip):
     if server['tor_status'] == 'Offline':
 
         if server_name in mail_cache:
+
+            current_app.logger.debug('Mail cache is %s' % str(mail_cache))
+
             send_date = mail_cache[server_name]
             now = datetime.utcnow()
             delta = now - send_date
 
             if delta.seconds <= 7200:
+                current_app.logger.debug('Server is in mail cache but not old enough to resend mail')
                 return server
             else:
+                current_app.logger.debug('Server tor status is offline for more than 7200 seconds')
                 _send_offline_mail(server_name, server['last_updated'])
         else:
+            current_app.logger.debug('Server is not in mail cache')
             _send_offline_mail(server_name, server['last_updated'])
     elif server_name in mail_cache:
+        current_app.logger.debug('Removing server from mail cache')
         del mail_cache[server_name]
 
     return server
diff --git a/ennstatus/log.py b/ennstatus/log.py
--- a/ennstatus/log.py
+++ b/ennstatus/log.py
@@ -24,7 +24,7 @@ def init_logging(app):
     rotating_file_handler.setLevel(logging.INFO)
     rotating_file_handler.setFormatter(logging_formatter)
 
-    if app.debug:
+    if app.debug or app.config['ENABLE_DEBUG_LOG']:
         second_rotating_file_handler = logging.handlers.RotatingFileHandler(
             'log/ennstatus_debug.log',
             maxBytes=1300000,